The Generation Hustle Podcast: Recent Episodes

Generation H

Sharing the journeys of amazing hustlers making an impact in their industries.

In this podcast episode, we sit down with Brendon Redlinger VP of Marketing at Chili Piper.

Brendan shares insights from his early career, moving from sales to marketing, and delves into the nuances of being a fractional leader. We cover the importance of understanding one's path to tech, embracing growth hacking, and the value of fractional leadership in organizational strategy and filling gaps.

Brendan highlights his approach to marketing and growth in startups, emphasizing data-driven decision-making, strategic leadership, and the significance of brand and customer satisfaction. We also discuss the future of marketing in the context of AI and changing consumer behaviors.

02:42 The Shift to Fractional Leadership Roles

06:13 The Value of Diverse Experiences in Career Development

10:46 Defining Marketing vs. Growth in Startups

14:35 Leadership Qualities and Strategies in Startups

21:46 Insights on Metrics and Resource Allocation in Marketing

27:48 Exploring Marketing Metrics and Strategies

34:58 The Future of Marketing in the AI Era

43:09 Personal Insights and Philosophical Musings

48:19 Lightning Round: Quick-fire Questions

Have you ever considered what keeps customers coming back for more? Megan Yen, VP of Customer Success and Activation at Ramp, joins us to unravel the secrets behind building a thriving customer success department.

With her extensive background transitioning from management consulting to the tech world, Megan brings a unique perspective on fostering early customer activation and combating churn in consumption-based business models.

This episode peels back the layers of what makes for a successful customer journey, from the initial onboarding experience to the nuanced dance of keeping clients engaged over time. Whether you're a CS professional or curious about the inner workings of tech company growth, Megan's insights are invaluable in understanding the compelling world of Customer Success.

01:58 The Evolution of Megan's Career

04:09 The Importance of Customer Success in Business

05:37 Ramp's Culture and Success Factors

06:44 Evolving Role of Customer Success in Tech

08:49 Hiring for Customer Success: Skills and Qualities

11:54 Revenue Responsibility in Customer Success

13:18 Onboarding and Activation: Key to Customer Retention

15:56 Predictive Analytics and Leading Indicators

18:59 Cross-Functional Collaboration and the Pod Model

24:45 Early Day Struggles and Scaling Onboarding at Ramp

30:41 Addressing Churn: Strategies and Customer Understanding

33:54 The Importance of Credibility and Brand in Customer Retention

35:56 Embracing Innovation and AI in Customer Success

46:32 Lightning Round: Quickfire Questions

In this episode, our guest is Christina from NewView Capital, where she shares her journey into the world of tech and venture capital, moving from investment banking to major roles at Google and Atomico before joining NewView.

Christina discusses her experiences living and working in various cities worldwide and offers insights into the cultural nuances in communication and business practices across different regions.

Christina also talks about building relationships in VC, selecting sectors for investment, and offers her unique perspective on work-life balance and success.
03:51 Navigating the Global Tech Landscape
06:44 Deep Dive into NewView Capital
15:02 The Art of Networking in Venture Capital
19:53 Capital Allocation: The Underrated Skill of Top CEOs
22:11 Mentorship and Learning from the Best
23:25 Reflecting on the Venture Ecosystem: OpenView's Dissolution
24:30 The Anatomy of VC Fund Failures
28:52 Exploring Promising and Challenging Industries
33:43 Personal Insights on Work-Life Balance
40:40 Reflections on Career Choices and Regrets
45:45 Lightning Round: Quickfire Questions

This episode features CJ Gustafson, the CFO of PartsTech and founder of the popular finance blog Mostly Metrics. He started his career in PE eventually wanting a bigger challenge, helping him land a role at a startup. Now as CFO, he describes the day to day and what it means to be the right hand person to the CEO.

In this episode, we cover topics such as:

The role of a CFO
Common financial mistakes made by startups
Forecasting in a hypergrowth company
The world of vanity metrics

00:03:00 Path to tech00:07:52 The CFO role has evolved significantly.00:10:49 Managing expectations in unpredictable startups.00:16:37 Choose companies with growth potential.00:20:02 Transparency and trust drive success.00:24:06 Personalize and forecast for success.00:30:20 Importance of cash flow forecasting00:36:08 Metrics should be understandable, comparative, and be behavior-changing.00:41:59 Avoid relying on vanity metrics.00:46:02 Hiring within finance00:51:32 Control of time equals happiness.00:55:41 Stack your talents for success.

Casey Woo is a seasoned multi-stage operator and 7x CFO with over two decades of experience in business operations and finance from investment banking on Wall Street to Silicon Valley tech start-ups.

Casey now leads 700+ CFOs, COOs, and Biz Ops company builders as the co-founder of Operators Guild, a community for professionals in strategic finance and operations roles. He strongly believes that community makes a difference for start-ups and professionals. When he’s not working, Casey spends time in California’s Bay Area with his wife and three children.

00:02:30 Casey's path to tech

00:09:13 Career exploration leads to growth.

00:12:55 Trust your gut, not timelines.

00:19:23 Building a supportive community for operators.

00:23:25 Building a successful community requires authenticity, engagement, and generosity.

00:31:37 Syndicates enable angel investing opportunities.

00:38:09 Empowerment and accountability in leadership.

00:40:22 Let go and trust talented individuals.

00:49:48 Nurture meaningful relationships through community.

00:51:06 Invest time in meaningful relationships.

This podcast features an interview with Charlie, Head of Marketing at Finch.

Charlie shares his background growing up in the Bay area and being exposed to technology from a young age. He reflects on the challenges of entering the tech industry in 2010 and compares it to the current landscape.

In this episode, we discuss how the marketing leader has evolved to be more focused on revenue. He highlights the importance of setting a clear strategy that aligns with company direction and working closely with other teams. We also go into depth on hiring practices and pathway to CMO.

00:03:24 Marketing leaders drive revenue growth.

00:08:47 Pathway to becoming CMO: Gain diverse marketing experience.

00:11:27 Adapting to new roles is important.

00:19:58 AI is changing marketing roles.

00:21:43 Allocating marketing budgets requires strategic decision-making.

00:31:18. Metrics should be connected to revenue.

00:32:38 Connecting marketing to revenue is crucial.

00:41:16 Brand is important for talent.

00:44:49 Embrace adversity for personal growth.

00:49:02 Open to helping and connecting.

We sat down with Grace Ge, Principal at Menlo Ventures. Growing up in a small town in Texas, she was inspired by her father's involvement in robotics and tech, eventually catapulting her into a career in VC.

In this episode, she shares her thoughts on the flaws of the current partnership model in VC firms and how VC remains largely a solo sport.

Grace also emphasizes the importance of proactive sourcing and hustling to find the best companies, rather than relying solely on network and brand.

We also deep dive into Ilan Frank's (VP Product at Airtable) framework on how to become enterprise-ready, as many companies tend to struggle with scale!00:10:34 Career path: VC requires experience.00:13:20 Partnerships in VC need improvement.00:16:24 VC role has evolved, hyper-specialization.00:22:01 Proactive sourcing and all-in partnership.00:32:29 Enterprise readiness criteria: scale, security, compliance, administration, usability.00:33:06 Importance of scalability in software.00:41:54 Risks of AI concentration.00:47:11 Importance of diversity in tech.00:50:07 Importance of diversity in tech.00:54:00 Lightning Round

In this episode, we dive into the fascinating journey of Pratyush Buddiga, a former professional poker player turned senior associate at SUSA Ventures.

Pratyush shares his experiences of being ranked second in the world in professional poker, the highs and lows of his career, and how he transitioned into the world of tech and venture capital.

We also explore the importance of intuition in decision-making, the value of faith in overcoming challenges, and the mentorship and learning opportunities at SUSA Ventures. Join us for an insightful conversation on competition, risk, and personal growth in the world of startups and investing.

[00:04:47] Professional poker career

[00:07:39] Competition and mamba mentality.

[00:11:26] Understanding players' strategies in poker.

[00:12:01] People's core being expressed.

[00:16:02] Power of intuition in decisions.

[00:19:06] EV in real life decision-making.

[00:21:35] Overcoming financial and personal challenges.

[00:27:41] Faith and community in career.

[00:31:15] Creating the kingdom of heaven.

[00:35:07] Web3 and its future.

[00:37:14] Control in decentralized finance.

[00:40:35] Regional banks and startup ecosystem.

[00:44:09] Humans are meant to create.

Zain, a principal at Ridge Ventures, talks about his journey into the tech industry and his transition to becoming a venture capitalist. He discusses the opportunities and challenges in the industry, including the impact of big tech companies.

We delve into the crucial skills required for successful investors in venture capital, emphasizing the significance of building strong personal relationships and having empathy. Zain shares his thoughts on how being a venture capitalist goes beyond mere transactions and involves forming deep connections with founders.

Overall, the episode underscores the significance of building strong personal relationships and possessing empathy as essential skills for successful investors in venture capital. These skills enable investors to truly understand individuals, aid in their growth, and make well-informed investment decisions based on genuine relationships and trust.

00:03:44 Transition from law to tech 00:07:48 Propensity for action and curiosity. 00:13:15 VC trend: Solo GPs emerging. 00:14:48 Venture trends shifting with COVID. 00:22:53 Importance of curiosity in venture. 00:24:06 Learning from mistakes is essential. 00:28:50 Founder qualities for success: special skills, unique storytelling, understanding their motivations. 00:33:37 Importance of building relationships 00:40:11 Secondary sales can benefit founders. 00:43:28 Twitter's evolution and impact 00:49:51 Potential risks of social platforms. 00:53:30 Being empathetic and connecting deeply. 00:58:00 Finding your voice and vulnerabilities.

On the 100th episode of the Generation Hustle podcast, Andrew shares his perspective on the pressures and misconceptions surrounding entrepreneurship. He warns against the obsession with big numbers and external validation, which can lead to a skewed perception of what it takes to succeed in business. Andrew also reflects on his own upbringing and how his early fascination with business ultimately led him to founding Acquire.

We also talk about strategies needed to get your business acquired, how to scale as a bootstrapped founder and common mistakes founders make at an early stage

00:02:00 - Entrepreneurship is not about extremes. 00:08:18 - Building in public builds fans. 00:11:10 - Building trust through personal branding. 00:20:45 - Bootstrap success: distribution & payback. 00:21:50 - Bootstrap businesses need quick profitability. 00:28:04 - Brand as David, not Goliath. 00:35:26 - Make acquisitions more efficient. 00:39:28 - Celebrate small exit successes. 00:43:48 - Starting small is perfectly fine. 00:49:10 - The rise of startup marketplaces.

In this fascinating episode, I had the pleasure of talking with Carla Matheson, a true trailblazer in the world of finance and a visionary leader. Carla shares her journey from working as a nanny for an entrepreneurial family to becoming the CFO of Tiny Capital and the impact of technology on the finance function. We discuss how her early experiences shaped her career and how she transitioned from the corporate world to the tech startup scene.

Carla and I explore the challenges faced by Canadian tech companies, the skills and responsibilities of a startup CFO, and the importance of effective incentives for startups. We also discuss the evolving role of the CFO in the age of artificial intelligence and the complexities of navigating VC and PE investments for early-stage companies.

Finally, we delve into the world of board member communication and the importance of objectivity and critical thinking during times of disagreement. We share our personal definitions of happiness and how it can be applied to our work and lives. Don't miss this insightful conversation with Carla Matheson as we uncover the secrets to success in finance and tech.

(0:01:30) - Finance Journey

(0:08:41) - Startup CFO Qualities & Responsibilities

(0:16:26) - Effective Incentives for Startups

(0:20:10) - Sales and AI in Finance

(0:33:40) - Navigating VC and PE Investments

(0:37:13) - Investing Challenges for Early-Stage Companies

(0:48:27) - Board Member Communication and Disagreements

How did Geoff Charles, VP of Product at Ramp, go from a background in consulting and finance to revolutionizing the world of product management in tech? In this fascinating conversation, we discuss the evolution of product roles, the importance of collaboration, and prioritizing value creation.

We dive deep into Geoff's role at Ramp, the critical aspects of product management in tech startups, and his approach to making decisions that drive the company forward. Geoff also shares insights on building a successful company, including understanding the Total Addressable Market, tailoring the product playbook to the specific business, and designing a product that leverages top engineering talent.

Finally, we explore the world of AI in product management, the importance of data privacy, and how technology can be used as a tool to empower people.

Timestamps:

Geoff Charles' Background and Transition to Product Management [00:02:45]

The Role of Product Management [00:13:36]

Prioritizing Relationships with Engineers [00:15:25]

Challenging TAM [00:21:08]

User Experience at Ramp [00:28:29]

Ramp's Target Market and Differentiation [00:34:02]

Biggest Mistake at Ramp [00:40:30]

Fear Mongering and AI [00:46:42]

Cultivating Happiness [00:49:37]

Lightning Round [00:51:34]

Lucy Guo shares her personal journey from a young hustler to co-founding Scale AI and Passes, emphasizing the importance of confidence and persistence in entrepreneurship. The episode also delves into co-founder dynamics, pivots, customer acquisition, and AI's impact on the economy.

We also deep dive into Lucy's personal thoughts on how success impacts personal image, her biggest regret and sharing her thoughts on folks who come from privilege.

If you are a creator check Passes out - https://www.passes.com/

Timestamps

Lucy's journey in the startup space [00:02:35]

Minimum Viable Product [00:07:28]

Confidence in Success [00:10:10]

How Scale AI started [00:13:35]

Landing the first customer [00:17:29]

Building Passes [00:22:23]

Qualities and skills for early-stage startup hiring [00:26:44]

AI's impact on innovation and the economy [00:30:54]

Authenticity and Polarizing Personality [00:36:13]

Emotions in Business Decisions [00:38:57]

Success and Guilt [00:45:36]

Success at a young age [00:47:51]

Lightning round [00:50:24-00:52:39]

Episode 96 is with Kyle Harrison, General Partner at Contrary!

In this episode, you will learn Contrary's investment approach, how storytelling drives the world, how to achieve investor-founder fit, and a particular trend amongst tech unicorns that Kyle refers to as “Thinning the Herd”. He also details the downstream impact of the current tech layoffs as well as his experiences on Harry Stebbings' podcast - 20VC.

Kyle is one of the most prominent writers in the venture space today, sharing his thoughts at his blog, Investing 101 2.0. Before joining Contrary, Kyle worked in some of the best names in VC, from TCV to Coatue to Index. Through all of these experiences, Kyle has led or participated in investments including Ramp, Pave, Anduril, Gitlab, Databricks and Snowflake to name a few.

Contraryhttps://contrary.com/

Timestamps
2:12 - Intro to Kyle
7:13 - Storytelling drives the World
9:18 - What makes a good investor?
13:45 - Achieving "Investor-Founder Fit"
17:57 - Contrary's Investment Approach
21:47 - What is one contrarian opinion?
25:30 - “Thinning the Herd”
31:50 - Advice for Managing a Down Round
36:15 - Downstream Impact of Tech Layoffs
48:10 - 20VC with Harry Stebbings
51:35 - Proudest Moment & Biggest Regret
54:45 - Lightning Round

Episode 95 is with Brian Hollins, Founder & Managing Partner at Collide Capital!

In this episode, you will learn best practises on building meaningful relationships while networking, the importance of representation, the highs and lows of raising funds, and how to set yourself up for success out of school. Brian also touches on generational differences, with a term he refers to as Men Z Minded Consumer Software. More on that later.

Prior to Collide Capital, Brian spent six years working at Goldman Sachs across investment management, investment banking, and merchant banking. He is also a founding board member of BLCK VC, the largest black investor community in the US.

Born and raised in DC, Brian received his undergrad from Stanford U and his MBA from Harvard Business School.

Collide Capital
https://www.collidecap.com/

Timestamps
2:00 - Path to VC
5:54 - Investment Banking @ Goldman Sachs
10:00 - Transactional Relationships
12:30 - Sibling Relationships
17:35 - Collide Capital
22:30 - Choosing Your Business Partner
25:30 - Importance of Representation
31:14 - Audience Question - Highs and Lows of Fundraising
40:53 - Advice for Emerging Managers/GPs
43:45 - Venture vs. Building
50:30 - Gen Z Minded Consumer Software
54:10 - Pride & Regret
57:20 - Lightning Round

Episode 94 is with Earnest Sweat!

In this episode, you will learn how to provide value when building relationships, the three main problems faced by every industry, and the current economic outlook from the lens of a VC and that of a Founder.

Previously as a venture partner at GreatPoint Ventures, Earnest focused on investments particularly within three areas: Commerce Infrastructure, the Built Environment, and IT & Data Infrastructures. Prior to GreatPoint, Earnest was a founding member at Prologis Ventures, the venture arm of the world’s largest industrial real estate owner. Earnest is an alum of Columbia University and earned his MBA from Northwestern’s Kellogg School of Management.

Timestamps
2:05 - Intro & Background
12:22 - Breaking into VC
28:40 - Investment Thesis
29:45 - Three Main Problems of Every Industry
36:20 - Unpopular Investment Belief
44:00 - Economic Outlook from the POV of VC
49:40 - Economic Outlook from the POV of Founders
57:00 - Building Relationships & Providing Value
1:00:20 - Lightning Round

Episode 93 is with Jason Shuman, General Partner at Primary Venture Partners!

In this episode, you will learn how to calculate your business’ TAM, the difference between Portfolio impact and platform, how to pitch to an LP, and hire the best candidates. Jason also explains his outlook on the macro environment and how best to fundraise right now.

At Primary, Jason leads new consumer investments including consumer healthcare, fintech, and marketplaces. The Boston native and University of Miami alum has jumped between sides of the table over the last eight years but started his career as the Founder of a D2C footwear company.

Forbes featured him on the 30 Under 30 in Venture Capital list; Venture Capital Journal named him one of Venture Capital's 40 rising stars.

Primary Venture Partners
https://www.primary.vc/

Timestamps
2:05 - Intro to Jason
4:00 - DTC Sneaker Business
6:35 - Foray into Venture Capital
8:15 - Primary Venture Partners
9:46 - Portfolio Impact vs. Platform
12:09 - Calculating TAM
18:39 - Best Advice for Fundraising
21:04 - Biggest Fundraising Mistakes
24:50 - Hot Take - “Hire Based on Childhood, not Investment Thesis”
28:10 - Defining a Good Investor
30:35 - Macro-Economic Outlook
35:35 - How to Pitch to an LP
45:20 - Company Valuations
51:57 - Lightning Round

Episode 92 is with Jordan Segall, Principal at Redpoint Ventures!

In this episode, you will learn the differences between early and late stage investing, what makes a good market opportunity, the balancing act of the Investor-Founder relationship, and how Open AI and ChatGPT is going to change the future of work. Jordan also details his thoughts on the macro environment and hype trains in the AI industry.

At Redpoint, Jordan has made investments into Cyberhaven, Heartex, Dagger, and Railway. Prior to that, he brings a wealth of experience ranging from McKinsey & Co., Palantir Technologies, SalesforceIQ, C3, and Unusual Ventures. Jordan attended Stanford University from where he holds an MS in Management Science & Engineering.

Redpoint Ventureshttps://www.redpoint.com/

Timestamps
1:40 - Intro
6:35 - Redpoint Ventures
8:46 - Early Stage vs. Later Stage Investing
10:28 - What Makes a Good Market Opportunity?
11:48 - Investment Case Study - Railway.app
14:14 - Biggest Challenge as a VC
17:15 - The Investor-Founder Relationship
20:00 - Providing Candid Feedback to Founders
25:24 - Macro-economic Environment - Fundraising advice
31:58 - Open AI & ChatGPT
34:32 - Hypetrains in A.I.
37:40 - Lightning Round

Episode 91 and the Season 3 opener is with Alessio Fanelli, Partner at Decibel VC!

In this episode, you will learn about Decibel’s investment strategy, how they help early stage startups, and the future of data tools. Alessio also details his journey to Venture Capital, building tools for technical founders, dealing with imposter syndrome, and how gaming helps him be a better VC.

Before Decibel, Alessio was a Principal at 645 Ventures, where he helped lead investments in dev tools, security, and enterprise SaaS. His investments included Cube Dev, Panther Labs, Launchable, Oort, and Bigeye, amongst others. He works with founders on everything from product design to helping with recruiting technical talent.

Earlier in his career, Alessio was the founder of Smart Torvy, an open source & hardware home automation platform, and was a lead engineer at early-stage startups such as Welcome Tech. He’s still active in the open-source community as well.

Decibel Partners
https://www.decibel.vc/

Timestamps
1:45 - Intro
5:07 - Becoming a VC
10:07 - VC Focus - Aggregators vs Specialists
13:45 - Evaluating Early Stage investments
18:20 - Most Difficult Part of Being a VC
21:29 - Imposter Syndrome in VC
25:29 - Future of Data Tools - Provide Value
29:19 - Data Security
33:03 - Data Security Companies to Watch
34:55 - Macro-Economic Outlook
41:20 - How to Communicate Lay-offs
45:00 - Transferrable Skills from Gaming
47:35 - Most Memorable Moment
55:15 - Lightning Round

Episode 90 is with Amanda Robson, Partner at Cowboy Ventures!

Originally from Ancaster, Ontario, Amanda, better known as Robby, invests in B2B seed & pre-seed founders and focuses on innovations in developer tooling, data management, security, applied AI, and supply chain.

In November 2020, she led a US$3.2-million investment round in a securities-software company called Drata, now worth US$1 billion.

When she’s not crushing it as a newly minted and youngest partner at Cowboy Ventures, she’s running her organization, Modern Angels, which seeks to democratize funding for women and non-binary people. She also co-hosts her own podcast, The Open Source Startup Podcast.

Cowboy Ventures is a seed-stage focused fund investing in digital startups that seeks to back exceptional founders who are building products that re-imagine work and personal life in large and growing markets.

We sit down to speak with Robby about her career journey from Ontario to Silicon Valley. She details the tech landscape across North America, the importance of DEI, why she’s big on Open Source, the art of cold outreach, and much more.

Cowboy Ventures

https://www.cowboy.vc/index

Timestamps

2:45 - Intro

5:24 - Importance of Cold Outreach

9:57 - Tech Industry - Canada vs. USA

12:32 - Amanda “Robby” Robson

15:59 - Joining Cowboy Ventures

18:25 - Cowboy Ventures Investment Thesis

25:17 - What Makes a Successful Founder

28:00 - Common Hiring Mistakes Founders Make

29:40 - Importance of Diverse Teams

32:50 - What is Open Source? Why is it important?

41:50 - The Open Source Podcast

47:20 - Modern Angels

51:24 - Time Management

55:40 - Lightning Round

This episode is sponsored by · Anchor: The easiest way to make a podcast. https://anchor.fm/app

Episode 89 is with Rachel Star, Principal at Unusual Ventures!

Unusual Ventures is an early-stage firm that invests in both enterprise and consumer startups. They lead pre-seed to Series A investments in software startups, supporting founders from idea to IPO, enabling startups with hands on support and expertise during their early journey.

Rachel is Principal at Unusual helping to build and support the firm’s consumer investments. With a passion for products and people, she started her career as a consultant with McKinsey & Company with a focus on consumer brands, retailers, supply chain, and manufacturing.

Most recently, Rachel was an early-stage investor on the consumer team at Shasta Ventures. She has been a speaker at TED events, for the Aspen Institute, and at Autodesk University.

We chat with Rachel about her career journey from Consulting to VC. She details key learnings and transferrable skills, what makes a great mentor in this space, how to manage the stress of the job, and ultimately, how to become a VC. This was an insightful conversation that we hope you enjoy!

Unusual Ventures

https://www.unusual.vc/

Timestamps

2:30 - Intro to Rachel

4:55 - Transferrable Skills

7:28 - What Makes a Great Mentor

12:30 - Managing Pressure on the Job

14:27 - Key Learnings

18:18 - Should You Become a VC?

21:11 - Unusual Ventures

25:37 - Investment Criteria

31:57 - Understanding Your Business Needs

33:28 - Working @ Unusual Ventures

35:24 - Hiring @ Early Stage StartUps

45:55 - What Makes a Visionary?

49:35 - How to Become a VC

51:45 - Lightning Round

Episode 88 is with Chris McCann, Co-Founder & Partner at Race Capital!

Race Capital is an early stage venture capital fund that lead pre-seed and seed stage technology startups, interested in the enterprise/B2B space, especially anything within the infrastructure layers of the stack. The company prefers the seed stage because it allows for the greatest impact, using a founders’ first, investor second, approach.

Chris is the seed investor in Solana, FTX, Lightning Labs, Zeet, Notifi Network, and many other companies across Web3 and Web2.

Prior to Race Capital, Chris founded and led the community program at Greylock Partners and prior to that, he was the Co-Founder and CEO of Startup Digest – one of the earliest technology focused email newsletters – which he grew to +1M subscribers before being acquired by Techstars.

We talk to Chris about his journey in tech and venture capital. He explains the creation of Startup Digest, how he stumbled into VC, the importance of community, his early investments into bitcoin, Web 3.0 and much more.

Race Capital

https://race.capital/

Timestamps

2:55 - Intro to Chris

6:11 - Chris’ Award-Winning Photography

13:00 - Creation of ‘Startup Digest’

19:50 - Working at Greylock (VC)

25:12 - What is “Community”?

33:32 - Learnings from Greylock

36:50 - Investing as an Angel vs. Investing as a VC

40:32 - Bitcoin and Ethereum

47:05 - Race Capital

51:30 - Securing an Equitable Deal

59:50 - Web 3.0

1:07:30 - Lightning Round

Episode 87 is with Hamzah Nassif, Parnter at Real Ventures!

Real Ventures is an early-stage venture firm focused on serving daring entrepreneurs with the ambition to create successful, global companies. Since 2007, Real Ventures has dedicated itself to building the Canadian startup ecosystem on the belief that people, not money, build game-changing companies. Real Ventures manages $325 million across five funds and its active portfolio of 100+ companies is currently valued at $10 billion.

An engineer first and investor second, Hamzah began his career working on Qualcomm’s first-generation multiprocessor chipsets in Boulder, Colorado. After 9 years of engineering study and work in the US, he moved halfway across the world to work with startups in the frontier and emerging markets of the Middle East.

We talk to Hamzah about his career journey thus far, from engineer to Partner. He details the Investment thesis of Real ventures, the day to day of a partner and board member, the importance and role of the board, and much more.

Real Ventures

https://realventures.com/

Timestamps

2:20 - Intro

12:50 - Defining Product-Market Fit

14:50 - It’s Ok To Be Wrong

17:30 - Convertible Notes & SAFEs - Pros & Cons

25:25 - Advice for Founders to Protect Themselves Financially

26:50 - How to Run a Tight Fundraising Process

28:00 - Why Do Boards Members Exist?

33:38 - Providing Feedback as a Board Member

35:50 - Guidelines for Board Members

38:10 - Day to Day of a Partner at Real Ventures

42:00 - Real Ventures

48:00 - Future Trends of A.I.

53:00 - Risks of Consolidated Power in Tech Companies

57:00 - Lightning Round

Episode 86 is with Claire Rafson, Investor at Eniac Ventures!

Based out of Eniac’s New York office, Claire is passionate about democratizing access to capital, making essential services like FinTech and health care more accessible, and embedding ESG (environmental, social, and governance) principles into companies.

Eniac Ventures leads seed rounds in bold founders who use code to create transformational companies. Armed with over 80 years of combined experience building their own companies, Eniac does more than just provide capital. They provide a platform through an expansive network with a strong belief in community at the heart of their investment approach.

We talk to Claire about her journey into VC. She details her day to day as an investor, what Eniac looks for in transformational founders, and how they’re pushing the bar on democratizing access to capital.

Eniac Ventures

https://eniac.vc/

Timestamps

2:22 - Intro to Claire

8:00 - Mentorship & Representation

10:33 - Managing Mental Health

13:28 - Interviewing for Venture Opportunities

19:05 - Eniac Ventures

21:05 - Claire’s Day to Day

25:50 - What VC’s Look for in Founder Meetings

32:00 - Creating Strong Deal Flow

36:15 - Quantity vs. Quality

38:03 - “Lost Deals”

41:45 - Introverts vs. Extroverts in VC

43:45 - Democratizing Access to Capital

56:16 - Lightning Round

Episode 85 is with Sai Senthilkumar, Principal at Redpoint Ventures!

Redpoint Ventures partners with visionary founders to create new markets or redefine existing ones. The firm invests in startups across the seed, early and growth phases. Since 1999, Redpoint has backed over 465 companies with 140 IPOs and M&As, including Netflix, Twilio, and Zendesk. Currently, the firm manages $4 billion across multiple funds.

Sai is a Stanford University graduate and former Investment Banker turned VC focussed on growth investing. Pivoting his career from engineering and banking to VC, Sai looks for emerging companies and markets to support within infrastructure software.

We speak with Sai about his career thus far. He details the transferrable knowledge and networking skills he used to transition from IB to VC. He describes what makes an interesting market or company for investment, visionary founders and how to identify them, and the metrics and factors that go into a successful investment.

Redpoint Ventures

https://www.redpoint.com/

Timestamps

2:30 - Intro to Sai

4:18 - Transferring Skills from IB to VC

5:20 - What Makes a Great Mentor?

7:45 - RedPoint Ventures

12:19 - Sai’s Day to Day

16:00 - What Makes a Market Interesting to Invest In?

17:17 - How to Invest in Developing Markets

20:55 - Investment Case Study - Monte Carlo

25:25 - Due Diligence Process at RedPoint

29:00 - Growth at All Costs Model

31:00 - Key Metrics for VC’s

33:20 - What makes a Visionary?

35:20 - How to Become a VC

37:25 - Lightning Round

Episode 84 is with Prateek Sanjay, Founder of Foundraisr!

Prateek helps FinTech and SaaS startups to source angel investors through cold emailing, with his company, Foundraisr.

His ability to create demand, build relationships and ultimately secure funding rounds for startups through cold outreaches have solidified his reputation as an expert in investor outreach.

We sit down with Prateek to talk learn how he created his six-figure business with no initial investment. He details his career journey, the Do's and Don’t's of email outreaches, and how he built his brand on LinkedIn that now consistently reaches millions every single day.

Foundraisr

https://www.foundraisr.com/

Timestamps

2:00 - Intro to Prateek

7:33 - Inbound vs Outbound Email Strategies for Growth

14:55 - Brand Building on LinkedIn

30:25 - How to Qualify Customers

34:00 - What NOT to do in Cold Emails

42:00 - How Prateek Helps Founders

47:30 - Thoughts on current VC/Startup Environment

Episode 83 is with Neal Soni, Co-Founder of Prepared!

Prepared is a start-up building technology to better connect citizens to the US emergency calling system. Currently, 911 call centres are technologically antiquated and unable to accept anything besides calls. Prepared’s services allow 911 dispatchers to send callers a text that connects them to a web app, where they can upload images, videos, GPS location, and even message back and forth.

Born out of personal experience - as Neal was a student in Westport schools during the 2012 Sandy Hook massacre - today over 30 cities have signed up for Prepared’s services to help keep schools and citizens safer.

We sit down with Neal to discuss the journey to building Prepared. He details the personal life experiences that led him and his co-founders to building on the idea, how Prepared is actively saving lives, issues with the emergency services infrastructure, and much more.

Prepared

https://www.prepared911.com/

Neal Soni

https://www.nealsoni.com/

Timestamps

1:55 - Intro to Neil

3:50 - Idea behind 'Prepared'

6:40 - Issues with the Emergency Infrastructure

8:50 - How 'Prepared' Works

11:50 - Building out the Founding Team

16:55 - Conflict Resolution in Teams

21:50 - Determining the Company Culture

23:05 - Hiring Engineers in Tech

31:49 - Buy vs. Build

34:29 - Work-Life-Balance

39:45 - Wealth Creation

43:53 - Lightning Round

Episode 82 is with Elizabeth Yin, Co-Founder & General Partner at Hustle Fund!

Hustle Fund makes pre-seed investments into the fastest-growing start-ups. With a team of former founders, Hustle Fund understands how amazing AND terrible startup life is and brings that authentic element to the table.

Elizabeth Yin was a former partner at 500 Startups where she invested in seed stage companies and ran the Mountain View accelerator. In a prior life, Elizabeth co-founded and ran an ad-tech company called LaunchBit (acq. 2014). Since then, she has reviewed over 20,000 startup pitches from around the world in the last few years and has helped numerous portfolio founders raise hundreds of millions of dollars.

She details her transition to venture capital from being a founder, what Hustle Fund stands for and looks for in founders and their companies, indicators of a good VC, dealing with investment regret, and much more!

Hustle Fund

https://www.hustlefund.vc/

Elizabeth Yin

https://elizabethyin.com/

Timestamps

2:10 - A Day in the Life

3:55 - Elizabeth’s Transition to Venture Capital

8:40 - Indicators of a Good VC

13:20 - The Best Way to Become a VC

15:30 - The Changing VC Landscape

18:27 - The VC Model - Fundamentals

21:00 - What does Hustle Fund look for?

26:10 - Dealing with Investment Regret/FOMO

27:13 - Lightning Round

Episode 81 is with Pablo Srugo, Partner at Mistral Venture Partners!

Mistral is a seed to early stage venture capital firm that focuses on getting start-ups to Product-Market Fit. They look for investments that leverage the power of the internet to make businesses smarter.

Pablo is a two-time founder, having first launched MyTutor.ca, a tutoring marketplace for university students that was acquired in 2014. He later founded GymTrack, a VC backed startup in fit-tech that helped monitor equipment usage in gyms.

We talk to Pablo about his unique journey to venture capital. He highlights what they look for in founders and VC partners at Mistral, how they evaluate startups for investments, his thoughts on the growth of the Canadian VC space, and much more!

Mistral Venture Partners

https://mistral.vc/

Timestamps

2:20 - Background - Founder Turned VC

13:00 - Transitioning from Founder to VC

16:10 - Advice for Founders working with VCs

22:33 - VC Deal Red-Flags

24:00 - What to look for in Founders

25:19 - “You want to have a pretty weak close rate.”

29:50 - Evaluating Passion

38:40 - Are we consolidating talent in Big Tech?

40:12 - Mistral Ventures

43:40 - VC Market - Canada vs. USA

50:38 - Building Relationships in VC

53:00 - How to Deal with FOMO

56:24 - Lightning Round

Episode 80 is with Maëlle Gavet, CEO of Techstars!

In June 2022, we attended the Collision Tech Conference in Toronto, Ontario, during which we had the opportunity to sit down with Maëlle for a personal chat.

Maëlle Gavet is a French businesswoman, author, and entrepreneur who has been a leading tech executive for over 15 years. She has been named to Fortune’s 40 Under 40 and Time’s Top 25 Female Techpreneurs’ among many other recognitions.

Her career has spanned across the globe from Principal at the Boston Consulting Group, CEO of OZON, Vice President of Operations at the Priceline Group, and now Techstars.

Techstars is a worldwide network helping entrepreneurs, founded on 3 simple ideas - entrepreneurs create the future, collaboration drives innovation, and great ideas can come from anywhere.

Since 2006, Techstars has invested in more than 3,000 companies and today has a market cap of $75 Billion.

We sit down with Maëlle to discuss her career journey thus far, and what made her choose her current role at Techstars. She highlights the differences in the tech landscape between North America and Europe, provides advice for early stage founders, and gives her perspective on the state of the industry and what needs to change.

Despite some background noise from the conference, this was a fun and informative conversation that we hope you enjoy!

Maëlle Gavet

https://www.maellegavet.com/

Techstars

https://www.techstars.com/

Timestamps

2:32 - Ikigai - Why Maëlle chose Techstars

4:45 - TechStars - a Universal Investor

7:40 - Advice for Early Stage Founders

12:54 - Current State of Diversity in Tech

15:24 - Trampled by Unicorns: Big Tech's Empathy Problem & How to Fix It

22:50 - “How do you want to be remembered?”

Episode 79 is with Chris Neumann, General Partner at Panache Ventures.

Panache Ventures is Canada's most active seed stage venture capital fund. The fund has a founders-first philosophy, a commitment to diversity and strategically co-invests with smart angel investors and seed stage funds.

Chris has 18 years of experience in Silicon Valley as an engineer, early startup employee, founder and investor. He helped build the world’s first 100 TB data warehouse, has invested in companies in more than 20 countries, and has mentored startups across 6 continents.

In this episode, Aman speaks to Chris about his journey from tech to VC. He details his fundraising experiences as a founder, his advisory methods now as a VC, and how Panache is pushing the Canadian tech ecosystem ahead.

Panache Ventures

https://www.panache.vc/

Chris Neumann

https://chrisneumann.com/

Timestamps

2:24 - Chris’ Background

13:43 - Tech Industry from 2000s to 2020s

17:20 - Chris’ Lumberjack Profile Pic

20:00 - Fundraising for a Data Start-Up

24:30 - Advisor vs Investor

25:50 - Challenges of Being a Founder

27:54 - Chris Critiques His Own Pitch Deck

33:44 - Best Advice for Founders

37:20 - Risk Tolerance is Relative

42:00 - Why Silicone Valley is so Unique

52:10 - How Panache Helps Companies & Founders

57:35 - Best Advice for Getting into VC

Episode 78 is with Muhammad Lila, Founder & CEO of Goodable!

Muhammad is an award-winning journalist, media founder, and strategist who leads multi-platform teams and creates content across all platforms. He specializes in taking complex subject matter and distilling it into easy-to-understand content that is designed to create impact. Muhammad holds a vast wealth of experience ranging from CNN, ABC, CBC, and now Goodable.

Goodable is one of the fastest growing news networks today. Using proprietary AI technology to search through thousands of news sources, the company identifies the best stories designed to make you happier and informed, all while avoiding negativity and the fear mongering we are accustomed to in news headlines.

Their tagline: "Give us Five Minutes, we’ll give you a whole new world!"

We sit down to speak with Muhammad about his career in journalism. He details his experiences in war zones, being targeted by ISIS and the Taliban with suicide bombers, how the newsroom and information landscape has changed over generations, and how Goodable is helping solve some of these problems we see today.

This was an incredibly profound conversation that touched on so many current and significant events that we hope you enjoy!

Goodable

https://goodable.co/

Timestamps

3:08 - Deciding the News is Innately Difficult

5:50 - Muhammad’s Background

6:45 - Seeing Diverse Names in Journalism

8:25 - “CBC Took a Risk on Me”

10:10 - How Toronto Culture helped Muhammad

15:19 - Meaning Behind Muhammad’s Name

18:12 - Full Circle Moments

19:45 - “Russians, Egyptians, ISIS & the Taliban all tried to kill me.”

21:17 - Muhammad’s Experience in Afghanistan

28:09 - Fear in Journalism

31:33 - Managing Emotions on the Job

34:24 - How the Ad-Revenue Model Destroyed News Media

39:53 - How Do We Fix Journalism?

43:14 - Who Decides the News?

48:05 - What is Goodable? How are they helping Journalism?

58:00 - The War on Freedom of Speech

01:08:06 - Why Donald Trump won the 2016 Election

01:10:31 - Social Media, Censorship & Human Behaviour

01:17:37 - Managing Mental Health

01:24:15 - Lightning Round

Episode 77 is with Markell Baldwin, Partner at Drive Capital!

Markell is a former Staff Electronic Design Engineer at Tesla with demonstrated experience in product development, sensor technology from a microcontroller level to the system level, and systems integration. At Drive Capital, he focuses on finding market defining companies in mobility, supply chain, and space.

We chat with Markell about his journey into tech, how minorities can break into tech, and important frameworks for continued growth and success in the industry. He also details his experience at Tesla and the future of Venture Capital. This was a really insightful convo that we hope you enjoy!

Drive Capitalhttps://drivecapital.com/

Timestamps

2:42 - Life-Changing Moments

9:03 - Working at Tesla

10:50 - Bradley Beal on competition

14:10 - Framework - Exposure, Possibility, Attainability

22:55 - Breaking into Venture Capital

26:22 - Drive Capital

27:50 - First Principles

32:33 - Highlights & Lowlights of VC

37:40 - Future of Electrification

45:30 - What makes Elon Musk so successful?

52:30 - Impact of Diversity in VC

59:00 - Lightning Round

Episode 76 is with Ashley Francisco, Head of Startup Developer Ecosystems for Google Canada!

In her role, Ashley manages Google Canada's Accelerator programs, scaled startup ecosystem events, and Canadian partner engagement. Her goal is to bring the best of Google's people, programs, products and technology to startup teams across the country. Ashley is a professional marketer by trade with a diverse background in local and global brand building at Google, Visa, Mondelez and Kraft Foods.

We sit down to talk with Ashley about her path to tech and ultimately Google. She details how Google’s Accelerator Programs are preparing founders of today to be the leaders of tomorrow. She also describes how you can land a job at Google, women empowerment in the tech environment, and the future impact of the tech industry.

Google for Startups Accelerator

https://startup.google.com/accelerator/

Google: Founder Fridays

https://rsvp.withgoogle.com/events/founder-fridays

Google for Startups Accelerator: Women Founders

https://startup.google.com/accelerator/women-founders/

Google for Startups Accelerator: Black Founders

https://startup.google.com/accelerator/black-founders/

Timestamps

2:00 - Ashley’s Role at Google Canada

3:05 - Landing a job at Google

8:05 - Skills Required to Work at Google

15:40 - Overcoming Imposter Syndrome

19:50 - Google’s Startup Accelerator Program

27:14 - Startup Story - Paper Stack

31:52 - Building a powerful community

34:37 - The Future of Google’s Accelerator Program

36:14 - Women Empowerment in Tech

38:50 - Future Impact of the Tech industry

41:45 - Thought Leaders to Follow in the Tech Space

43:55 - Making Connections in the Tech Space

47:34 - Managing Mental Health

51:23 - Defining Success

Episode 75 is with Jesse Abrams, Co-Founder & CEO of Homewise!

Recently distinguished by NEXT Canada as “The W. Galen Weston Top Entrepreneur”, by the American Marketing Association Hall of Legends as one of Canada's top 5 "Marketers on the Rise" and by Marketing Magazine as a "Top 30 Under 30" Marketer in Canada, Jesse is an accomplished business leader, Digital Marketer and Advertiser. He has a passion for growing businesses and never settling for the status quo.

Homewise provides Canadians with a better mortgage process with a simple online application that uses human language, helpful content and access to tech-powered professionals at every step to get a great mortgage. Their goal is to get the best deal and save their customers the most money possible.

We talk to Jesse about his journey into entrepreneurship, how Homewise is disrupting the mortgage industry, the current state of the Canadian real estate market, and much more. This was a great conversation that we hope you enjoy!

Homewise

https://thinkhomewise.com/

Timestamps

2:40 - Road to Entrepreneurship

8:15 - Can Entrepreneurship be taught/learned?

15:55 - Jesse’s Career Transition

24:30 - Advice for new Entrepreneurs

29:00 - The story of HomeWise and Early Growth

34:45 - How HomeWise Simplifies the Mortgage Process

42:29 - Building a Successful Team

49:10 - Current State of the Canadian Real Estate Market

56:16 - Should we stop blind bidding?

59:09 - Advice for Entering the Housing Market

1:07:17 - Importance of Charity Initiatives

1:14:00 - Lightning Round

Episode 74 is with Nicole DeTommaso, Senior Associate at Harlem Capital!

As a Senior Associate at Harlem Capital, Nicole focuses on deal sourcing, due diligence, and platform development. Prior to Harlem Capital, Nicole worked at RBC Capital Markets within the Investment Banking division, focused primarily on Mergers & Acquisitions and Initial Public Offerings within the technology and digital media sectors.

Harlem Capital is a venture capital firm on a mission to change the face of entrepreneurship by investing in 1,000 diverse founders over the next 20 years. They invest post product, or what they call 'Early Seed', with a commitment to reserving specific capital for investments in minority and women founders.

We talk to Nicole about her journey into Venture Capital. She details the day in the life of a senior associate at Harlem Capital, the criteria and due diligence for investing into good companies, the future of the internet, how VC’s are preparing for future economic downturns, and much more.

If you're looking to get into the VC space, this conversation is a great start!

Harlem Capital

https://harlem.capital/

Timestamps

2:07 - Intro to Nicole

4:49 - Lived Experience of Being a Minority in VC

8:45 - Importance of Mentorship along the way

10:53 - Working in Toronto

12:48 - Transitioning into Venture Capital

15:54 - Using Twitter to get into VC

18:03 - Nicole’s Pitch Deck when applying to Harlem Capital

24:15 - Working at Harlem Capital

27:10 - Why Web 3.0 is important

33:08 - A Day in the life of a Senior Associate at Harlem Capital

37:20 - How VC’s are Preparing for a Recession

44:18 - The Lack of Diversity in VC

51:12 - Advice for Maintaining Mental Health

54:23 - Lightning Round

Episode 73 is with Jess Chan, Founder & CEO at Longplay Brands!

Longplay Brands is a marketing agency working with B2C e-commerce brands in the health, wellness, and lifestyle spaces. The company M.O. is to work with businesses who are in it for the longplay - brands who are looking to create a legacy, build a lasting brand, and impact real lives. In other words, they build relationships at scale.

Prior to Longplay, Jess was the Chief Marketing Officer of BestSelf Co., a 7-figure e-commerce brand. Since founding Longplay, she has scaled it to over $1M in just 18 months working with DTC e-commerce brands from startup to 250M+ in revenue, and has grown to a fully distributed team of 20+ people.

We talk to Jess about her journey to entrepreneurship, how she scaled her company, why email marketing is still so important, and her advice on starting your own agency. She details what makes a good email campaign, how she deals with imposter syndrome in her day to day life, and her experiences with psychedelics. We hope you enjoy!

Longplay Brands

https://www.longplaybrands.com/

Timestamps

2:49 - Introduction to Jess

5:33 - Navigating Imposter Syndrome

7:29 - Shift from Corporate to Entrepreneurship

10:56 - Rejection, Failures, & Building Confidence

15:11 - The idea behind Longplay

16:54 - How Longplay helps businesses

18:38 - Why is Email so important?

21:14 - Do’s & Don’ts of a Good Email Marketing Campaign

24:07 - The Evolution of Email Marketing

30:31 - Key Drivers & Struggles of Scaling

38:35 - How to Make the right Hire

43:14 - Advice for building a Consultancy/Agency

46:13 - Happiness, Personal Development, & Self Reflection

52:55 - Networking & Establishing a Support System

55:50 - Psychedelic experiences

01:01:32 - Lightning Round

Episode 72 is with Leigh Marie Braswell, Principal at Founders Fund!

Before joining Founders Fund, Leigh Marie was an early engineer & the first product manager at Scale AI, where she originally built & later led product development for the LiDAR/3D annotation products, used by many autonomous vehicles, robots, and AR/VR companies. She also has done software development at Blend, machine learning at Google, and quantitative trading at Jane Street. Leigh Marie is originally from Alabama, graduated from MIT, and loves to play poker, run long distances, and scuba dive.

Founders Fund is a San Francisco-based venture capital firm that invests across all stages and sectors, with a portfolio that includes Airbnb, Lyft, Spotify, Stripe, and Oscar Health. Founders Fund was the first institutional investor in SpaceX and Palantir Technologies, and one of the earliest investors in Facebook. Founded in 2005 by Peter Thiel, the fund currently manages over $11B in aggregate capital.

We sit down to talk to Leigh Marie about her journey through to tech. She details what makes a company and its founder investment-worthy, the future of data and machine learning, and provides advice for early startups looking to grow. She also touches on the future of work, Elon Musk, Universal Basic Income, and much more. This was such an insightful conversation that we hope you enjoy!

Founders Fund

https://foundersfund.com/

Timestamps

2:43 - Leigh Marie’s Background

12:22 - Core Skills to be a VC

17:29 - What does it mean to “hustle”?

20:15 - The story of Founders Fund

23:11 - Advice for Building a Personal Brand

25:39 - Generalists vs. Specialists

27:15 - The Future of Data, A.I., & ML

32:28 - What Makes a Company Investment-Worthy

39:42 - Working with Peter Thiel

41:34 - Evaluating Start-Ups & Founders

46:39 - Learning from Failed Investments

49:44 - Missed Opportunities - Investment Regret

51:33 - Imposter Syndrome

53:10 - Elon Musk, A.I., & Universal Basic Income

55:29 - Advice for Protecting Future Job Security

58:13 - Lightning Round

Episode 71 is with Peter Zhou, Co-Founder & CEO of Rutter!

Rutter is building a universal API for e-commerce platforms. The e-commerce market is split across hundreds of platforms, such as Shopify, Squarespace, Amazon, and others. Each of these platforms has its own app store or its equivalent. Rutter is an integration layer letting any e-commerce tool build one integration to access any storefront or marketplace.

Peter attended Yale University before interning at Facebook as a Software Engineer prior to his entrepreneurial endeavours. We sit down to talk to Peter about his journey to founding Rutter, the mindset of a startup CEO, his tools to a successful fundraise and opportunities for wealth creation. This was an incredibly informative episode that we hope you enjoy!

Rutter

https://www.rutterapi.com/

Timestamps

1:25 - Peter’s Background

4:39 - The Need to Make an Impact

6:20 - Cultural Influences

11:05 - How to Embrace Entrepreneurship

13:50 - Mindset of a CEO

16:10 - Importance of Receiving Feedback

18:30 - Biggest Challenge of Becoming a CEO

21:20 - Peter’s Journey

24:40 - Key Learnings of B2B Entrepreneurship

28:07 - Sell Before You Build

30:40 - TL;DR of Rutter

35:45 - Rutter’s Approach to Fundraising

39:35 - Common Errors Made During Fundraising

41:35 - Prioritizing Mental Health as a Founder

46:50 - Wealth Creation Opportunities of the Future

50:10 - Thoughts on the Wealth Gap Issue

51:24 - Lightning Round

Episode 70 is with Adit Gupta, Co-Founder & CEO of Lula!

Lula is an institutionally backed delivery tech company, that helps stores by providing an all-encompassing platform that connects the world to them. Today, we're giving stores (convenience, liquor, pet, and more) the specialized technology, data, and customer success these merchants need to serve customers. This united network of stores powered by Lula enables independents and small chains to compete with major corporations as the nation's largest retail delivery marketplace.Adit is a Ph.D. student at Drexel University, with research interests in Computer Vision, Artificial Intelligence, and Human Computer Interaction.

We sit down to talk to Adit about the idea behind Lula, how he founded the company in a pandemic and successfully raised a $5.5M seed round. Adit also speaks on what students today should be prioritizing for their development. This was such an insightful conversation that we hope you enjoy!

Lula

https://www.luladelivery.com/

Timestamps1:36 - Adit’s Background & Experiences with Hack-a-thons

5:17 - Cultural & Family Influences

9:48 - What should students today invest in?

12:24 - The Story of Lula Delivery

16:40 - How does Lula help business owners?

20:58 - How to Raise a $5.5M Seed Round

30:30 - Prioritizing your investment needs

34:50 - Adit’s pursuit of a PhD

38:40 - Importance of Mental Health in Work & Life

43:53 - “Hustle Culture”

46:00 - Lightning Round

Episode 69 is with Robbie Crabtree, Founder of Performative Speaking!

Robbie is a retired trial lawyer turned Startup Founder Coach turning founders into powerful storytellers. Having started his career in the legal sector, Robbie helped victims get justice for violent felonies, murders, & child abuse cases as a successful trial lawyer. After eight years of competitive storytelling in a courtroom with 102 jury trials, Robbie realized that his storytelling abilities can be used for much more.

Since shifting his focus to helping founders in Seed to Series C levels as a strategic advisor & coach, Robbie has helped clients raise over $135M in venture funding, build companies worth billions, and make their vision a reality.

We talk to Robbie about his career pivot from lawyer to startup coach. He explains the makings of a great story-teller, how to pickup on cues when people are lying, and the mistakes that founders make with pitch decks. He also details his steps to scaling his influence and how to balance authenticity with growth.

This was a great conversation with so many learnings throughout that we hope you enjoy!

Robbie Crabtree

https://www.robbiecrabtree.com/

Timestamps

1:18 - Background & Career

7:11 - How to Pivot Careers With Your Skills

10:40 - What Makes a Good Story/Story-teller?

13:50 - Social Media “Guru’s”

17:50 - Jeff Bezos’ Story-Telling in front of Congress

19:21 - How to Tell If Someone is Lying

24:00 - Biggest Mistake Founders Make with Pitch-decks

31:00 - Resources to Become a Better Story-teller

33:39 - Robbie’s Approach to Clients

38:27 - How To Scale Your Influence

42:38 - Validation Through Status

45:36 - Authenticity & Growth

48:24 - Failure & Triumph

50:18 - Lightning Round

Episode 68 is with Dennis Xu, Co-Founder of Mem Labs!

Mem is the world's first self-organizing workspace that leverages artificial intelligence to equip knowledge workers in the world with the information they need to do their best work. The free app is an early access platform dedicated to pushing users to quickly jot down their thoughts without focusing too heavily on the underlying organization of them.

We talk to Dennis about his journey to founding Mem and the inspiration behind it. He details the difference in tech landscapes between Canada and the USA, his experience at Stanford University, and how they secured a $5.6M seed round from Andreessen Horowitz. Dennis also explains important skills for builders in tech as well as what a day in the life of a cofounder looks like.

This was a really insightful conversation that we hope you enjoy!

Mem

https://get.mem.ai/

Timestamps

1:18 - Dennis’ background

4:44 - Tech in Canada vs. Tech in USA

11:35 - Shift to remote work

16:40 - Experience at Stanford

21:14 - Must have skills to be a builder

25:38 - Hard Skills vs. Intangibles

27:30 - Three types of workers

32:06 - Navigating terminations

37:11 - What is Mem.ai?

51:04 - Day to Day Life of a Co-Founder

54:10 - Securing a Seed Round from Andreessen Horowitz

1:01:07 - Biggest Influences

1:04:02 - Philosophy on Wealth Creation

1:08:39 - Lightning Round

Episode 67 is with Raad Ahmed, Founder & CEO of LawTrades!

LawTrades is pioneering a new work model that economically empowers independent legal professionals to monetize their skills, while helping companies build distributed legal teams. General Counsels have access to a highly selective talent network of attorneys, paralegals, compliance, and legal ops, to complement their own legal department and company culture.

We talk with Raad about his early music passions and influences to entrepreneurship. He details his journey from first discovering the internet to making 6-figures in online ad revenue while in law school. Raad also details his mission to achieve a utopian work-life balance through LawTrades, and how they successfully raised $6M at an $80M valuation using just a link and without pitching to VCs. This was a great conversation that weaves through career, life, and philosophy that we hope you enjoy!

LawTrades

https://www.lawtrades.com/

Timestamps

3:05 - Passions & Influences

10:02 - “Passionately curious, but compulsively minimalist.”

18:34 - Challenges of Raising Capital

22:05 - How Justin Khan almost ruined LegalTrades

27:00 - How LegalTrades raised a $6M Series A with their customers

36:11 - VC Funding vs. RUV Funding

43:43 - What is LawTrades & What problem are they solving?

51:34 - Pros & Cons of Legal-Tech Industry

58:34 - Defining & Measuring Success

1:06:00 - Impact of the Founding Team

1:12:38 - Wealth Creation

1:20:36 - How Schooling Needs to Change

1:32:00 - Lightning Round

Episode 66 is with Maika Isogawa, Co-Founder and CEO at Webacy!

Webacy helps protect your digital legacy by allowing you to decide what you want to do with your digital life after you die. This includes your social media accounts blockchain-based assets, cryptocurrencies and other assets. Some of this involves deletion or memorialization of accounts, posting final, sequenced content, and transferring crypto or business accounts to your inner circle.

Maika is a former professional acrobat and performer for the Cirque Du Soleil brand of shows. She is also a Stanford '20 alumnus with a special concentration in Symbolic Systems, a program which combines the study of Human Computer Interaction, Software Engineering, Linguistics, Philosophy, and more. Maika was most recently a Cybersecurity Engineer for Microsoft, while Maika and Webacy have been recently recognized as a member of the Forbes 30 Under 30 list.

We sit down with Maika to discuss her early days with the Cirque du Soleil and how she became an entrepreneur. She details how she battles imposter syndrome, cultural influences in her life, including Anime, and how Webacy is securing digital assets for the world of tomorrow. This was a fun chat that we hope you enjoy!

Webacyhttps://www.webacy.com/

Timestamps

2:30 - Circus Acrobatics at Cirque du Soleil

8:00 - Overcoming Fear & Imposter Syndrome

10:25 - Importance of Hobbies & Side Hustles

13:10 - Influence of Culture

17:00 - Anime Culture

19:50 - Goal Setting for Success

24:40 - Pressure to Succeed

28:18 - Happiness & Success

31:00 - The story behind Webacy

33:14 - Crypto scam that stole from Maika

35:30 - Challenges of Crypto-adoption

38:50 - Defining Company Culture

42:37 - Webacy’s Founding Team

45:37 - Managing Differing Opinions

49:04 - Advice for new entrepreneurs

50:05 - Lightning Round

Episode 65 is with Harsehaj Dhami and Samantha Ouyang, two International Baccalaureate high school students based in Toronto.

Harsehaj is an impact driven student working to bridge the healthcare access gap to low income families and those struggling with their mental health. She is currently helping build a health startup based out of San Francisco that has just raised their seed-round. In her personal projects, she’s working on modelling CNN (convolutional neural networks) that uses brain EEG scans to diagnose depression.

Samantha is a goal oriented student, passionate about using STEM, design, engineering and innovation to create lasting change in the world. Having started off in competitive programming at an early age, her experiences led her to founding, Superposition Toronto, a non-profit that helps to bridge the gender gap in STEM.

Samantha and Harsehaj have both crossed paths in The Knowledge Society - where cohorts of students are encouraged to solve the world’s biggest problems using emerging technologies. They have both previously worked together on a project focussed on removing chemical pollutants from drinking water.

We talk to Harsehaj and Samantha about their respective journeys in the tech space, the various differences in education and culture between generations, the influence of asian households, and much more. This was such an insightful conversation that brought to light the various evolutions of education, life, culture, and tech through the years. We hope you enjoy!

Timestamps

2:45 - Harsehaj Intro & background

6:45 - Samantha Intro & background

11:25 - Early Lessons from their experiences

18:58 - Cultural Influences of an Asian household

27:14 - How can schools encourage more innovation?

30:30 - Challenges of Women in Tech

37:30 - Social Pressures on Millennials & Gen Z

44:42 - Pros/Cons of Social Media for Gen Z

53:19 - Increasing Cost & Competition in Schooling

1:00:12 - What is the current tech focus for Gen Z?

1:03:39 - Lightning Round

Episode 64 is with Alexandra Nuth, Co-Founder and COO at Control HQ!

Control HQ is a financial management tool for freelancers and flexible workers. The freedom and flexibility of self employment is coveted, but not the antiquated process of managing your money, from irregular pay to income taxes.

Alexandra built her way up in corporate strategy before teaming up with two colleagues on this venture to become the financial management company for independents.

We talk to Alex about her move from corporate to entrepreneurship, the future of flexible work and why ControlHQ is so important in this space, the importance of mentorship, and so much more.

This was such an insightful conversation that we hope you enjoy!

Control HQhttps://www.controlhq.com/

Timestamps

1:43 - Intro & Background

4:56 - Transitioning from Corporate to Entrepreneurship

8:50 - Important Core Values

10:57 - Building Company Culture

15:06 - Importance of Mentorship

21:40 - What is Control HQ?

24:29 - What makes Control HQ different?

28:30 - Importance of Diversity & Inclusion

38:40 - Lightning Round

Episode 63 is with Lloyed Lobo, Co-Founder and President of Boast A.I.

Boast A.I helps companies access the billions of dollars available in R&D tax credits and funding to improve insights and grow faster. Their software integrates financial, engineering, and project data to increase the speed, accuracy, and size of eligible tax incentives. In other words, Boast helps you maximize claims and innovate faster while you run your business.

Lloyed is an entrepreneur through and through, with a never ending desire to keep moving, building, and hustling. We talk to Lloyed about his journey in tech, how being a refugee of the Gulf War in Kuwait shaped his mentality on life, and the plethora of lessons he’s gathered through his experiences thus far.

This was an insightful and candid conversation that you hope you enjoy!

Timestamps2:01 - Background

9:00 - Engineering Uncertainty (for Success)

16:25 - Managing Mental Health

26:43 - Importance of your Network

30:14 - The CAMPER Framework

33:00 - What is Boast A.I?

35:08 - How Boast A.I helps businesses with R&D Credits

38:04 - The Future of Boast A.I

39:51 - Raising $100M from Investors

51:51 - Advice to Founders

53:02 - Lightning Round

Episode 62 is with Brice Scheschuk, Co-Founder of WIND Mobile (now known as Freedom Mobile) and currently the Managing Partner at Globalive Capital.

The telecom space is one of the most regulated and red-tape ruled industries to work within, making Wind Mobile’s story an incredible achievement.

Brice led the Finance, HR, Procurement and Supply Chain functions of one of the largest new entrant pure play wireless services providers and helped raised approximately $2B in capital to acquire spectrum and operate the WIND network.

Now, he manages a $100M investment firm in Globalive focusing on representative private equity, real estate, and venture investments.

We talk to Brice about his journey breaking into the Canadian telecom space, the evolution of entrepreneurship through different eras, and impactful skills necessary for anyone looking to achieve success. He also explains the importance of mentorship and how he’s helping the next generation through MindFrame Connect.

This was an incredible informative episode that we hope you enjoy!

Timestamps

2:20 - Background and Education

5:30 - The Entrepreneurship Journey & Mindset

11:30 - Transferrable Skills through Generations

15:55 - Founding WIND Mobile

23:00 - Advice on Seeking Investors

30:52 - Assessing & Managing Risk in Life

38:25 - What is Anti-Fragility?

47:30 - Decision Making & Regret

56:55 - MindFrame Connect

01:02:50 - Lightning Round

Episode 61 is with Ben Share, Co-Founder and CEO at Dime!

Dime helps turn your content into genuine digital collectibles for your followers to buy, sell, trade and collect. While NFTs have the potential to transform the way we create art and use the internet, we still need a system in place that's powerful enough and clear enough for everyone to use.

Dime is the first NFT marketplace to not require a crypto wallet, the first to transact purely in $USD, and most importantly, the first marketplace that ordinary people will want to use.

We talk to Ben about the utility of NFTs, the Blockchain and Web 3.0. We discuss the future of these technologies and how creators will be significantly impacted by advancements in this space. He details his journey founding Dime and what the internet of tomorrow will look like as the foundations are laid today.

If you’re looking to stay ahead of the next big shift on the internet, this episode is a must!

Timestamps2:15 - Intro to Ben

4:54 - What is Web 3.0?

6:28 - Significance of Blockchain

8:11 - What is an NFT? Why are they important?

15:47 - Importance of Community

19:05 - What is a Rug Pull?

22:10 - NFT Investing: How To

26:44 - What is Dime?

28:37 - How Dime helps purchase NFTs

31:22 - How NFTs and Web 3.0 will help creators

35:12 - Challenges in & Advice for the Web 3.0 and NFT space

39:38 - The Y Combinator Experience

45:54 - Lightning Round

Episode 60 is with Kris Bennatti, Co-Founder, CEO and Lead Developer at Bedrock AI!

Bedrock AI are experts and innovators in the adaptation of language models to financial text that facilitate a unique, quantamental approach to reading and understanding SEC filings.

In other words, they use underused, unstructured data sources to understand and predict earnings management, accounting problems and outright fraud.

We talk to Kris about her journey from accounting as a CPA to founding Bedrock AI. She details the importance of machine learning in the financial markets and how investors and companies alike can benefit from its use. This was an incredibly insightful conversation that we hope you enjoy!

Timestamps

2:50 - Career Journey from CPA to Coding

7:40 - Advice to newcomers to Data Science

10:04 - Machine Learning vs. Artificial Intelligence

13:16 - Deep Learning Based Language Models

17:45 - "AI is inherently biased."

22:00 - The Concept of Singularity

24:17 - What is Bedrock AI?

28:59 - Example of how Bedrock AI helps investors

35:28 - The future of Bedrock AI

39:16 - Finding the right Business Partners

41:36 - Challenges of being a Founder

45:20 - Lightning Round

We're back & starting off 2022 with a great guest from the world of HR!

Episode 59 is with Evan Hallward, Co-Founder and Co-CEO at Aboard!

Aboard enables growing startups & small businesses to find, implement, and automate their People Programs. From onboarding to offboarding, and everything in between, Aboard ensures that employees will be better prepared to succeed.

We talk to Evan about his motivation behind founding this platform. He details how his experiences in recruitment and HR led him to building a people-focussed company of his own. This was a great conversation with so many learnings. We’ve all had our fair share of bad interview and employment experiences. If you’re looking to revamp your recruitment and employee engagement, this episode is sure to help!

Timestamps2:15 - Evan’s Entrepreneurial Journey

6:14 - What does a successful interview process look like?

10:35 - War for Talent vs. Brand

11:40 - How to Optimize your Hiring Process

13:22 - How Start-Ups Fail at Hiring Talent

17:35 - Debunking the Negative Perception On Employment Length

19:51 - Defining “Employee Engagement”

24:45 - How to Retain Talent at your Company

30:19 - Transitioning from a “Task Role” to a “Manager Role”

31:45 - What is Aboard? How are they helping employers & employees?

36:50 - Lightning Round

Episode 58 is with Mark MacLeod!

Mark is a semi-active angel investor with a portfolio of 14 investments, 2 highly positive exits and counting. He was most notably General Partner at Real Ventures, Canada’s largest and most active seed stage fund. With a background in finance, he also served as CFO for software companies including, but not limited to, Shopify and Freshbooks.

We talk to Mark about his journey from finance to venture capital. He details his move from C-suite to investor, and the critical skills that are needed to help a start-up succeed. Mark also dives into the critical skills needed to become a leader in the industry.

This was a fun conversation with plenty of gems throughout, so we hope you enjoy!

Timestamps1:31 - Mark's Career Journey

7:00 - They Key to Learning Fast

8:30 - Importance of Product-Market Fit

9:50 - Managing Stress in Decision Making

12:25 - Critical Skills Young Professionals Need to Learn

15:30 - Don’t Chase Titles. Do this instead.

19:04 - What makes a great leader?

22:45 - How to Develop Trust amongst Your Team

24:42 - How to Successfully Fundraise with VCs

27:10 - What Makes a Start-Up Investment Worthy?

31:40 - How Mark got into DJ-ing and Fitness

34:40 - Lightning Round

Episode 57 is with Alexander Jivov, Co-Founder & CEO at Hopeful Inc.!

Hopeful Inc. is the first Social Fund-tech platform that enables nonprofits and charities to monetize their social media followers specifically for fundraising, while giving them visibility on why donors are engaging through a proprietary Storytelling A.I. dashboard.

Alex is a Salesperson, Digital Marketer, Full-Stack Web Developer, Chef, and published author - a true jack of all trades with an interesting career path to say the least!

We talk to Alex about his career journey and how he pivoted through so many different avenues. He describes the process of building a start-up in the non-profit industry, building out a successful founding team, and how to figure out the right career for yourself. Alex also details the importance of mentorship through accelerators and incubators from his experience with the Ryerson DMZ and UC Berkeley SkyDeck.

This was an incredibly informative episode that’s sure to have a bit of everything for everyone, so we hope you enjoy!

Timestamps

1:53 - Alex’s Unorthodox Career Path

4:32 - How to effectively experiment early on in your career

6:16 - Building a Client Acquisition Strategy

8:31 - How to Become a Better Salesperson

10:19 - What is Hopeful Inc & How are they helping non-profits?

16:31 - Challenges Faced by Hopeful Inc.

18:30 - Hopeful Inc.’s Acquisition

24:02 - Defining Success For Your Company & Employees

27:10 - The Future of Hopeful Inc.

29:00 - Advice for Entering the Non-Profit industry

32:04 - Lightning Round

Episode 56 is with Taran Singh Kainth, Co-Founder & CEO at Flahmingo!

After witnessing the financial crisis of '07/'08, Taran pursued his curiosity in finance and investing to understand the markets. His ambitions increased in complexity, from managing his family RRSP at the age of 16 to democratizing investing for students and young investors with the founding of Flahmingo.

Flahmingo is a native mobile application that allows you to begin investing with as little as $1! Their proprietary technology enables users to grow and maintain a diversified portfolio through the purchase and sale of fractional shares. These fractional shares allow Flahmingo users to own as little as $1 in companies like Tesla, Alphabet, Amazon and even Berkshire Hathaway.

We speak to Taran about his entrepreneurial journey, meeting and gathering knowledge from Tim Draper at Draper University, and the importance of financial literacy at a younger age.

This was a great conversation with an ambitious leader to keep an eye on for the future, so we hope enjoy!

Timestamps

2:25 - Financial Literacy and Building Wealth

6:50 - Early Finance Mistakes & Lessons

11:10 - How to build your financial knowledge

15:45 - Taran’s Investment Strategy

20:45 - Inspiration behind Flahmingo

24:00 - What is Flahmingo & How can it help you?

32:22 - What’s next for Flahmingo?

35:47 - Importance of Community

38:14 - Challenges of Building a Start-up

Episode 55 is with Tiago Teixeira, Co-Founder and CEO of xix3D and Founder of Sekanskin!

xix3D runs a 3D car configurator that helps visualize the artistic work through hyper-realistic renderings and custom graphics in seconds. Sekanskin has established the industry benchmark with meticulously dedicated vinyl artists that have a reputation for perfection.

After graduating with a degree in Psychology, Tiago decided to pursue his passion for cars, launching into the automotive space first with wrapping cars, to now innovating the way the entire business works.

We talk to Tiago about his drive and how he found his calling in the car industry. He explains his journey from masterminding the viral sensation Purrari - a baby blue Ferrari wrapped for none other than Deadmau5, to now leading a tech company taking the industry by storm. Tiago also details the impact of mentoring through the Ryerson DMZ, to expressing self-confidence to achieve your goals.

This was an incredibly motivational conversation, that we hope you can learn from and enjoy!

Timestamps

1:45 - The entrepreneurial journey

8:30 - Working with Deadmau5

9:50 - How to Acquire Clients for Your Business

13:00 - Origin of XIX3D

19:10 - Building a Tech Company without a Tech Background

24:55 - Networking and the Working with the DMZ

35:40 - Lightning Round

Episode 54 is with Phillip Gales, CEO and Founder of inate.ai!

Holding a Masters degree in Engineering from the University of Cambridge and an MBA from Harvard, Phillip is a serial entrepreneur focussed on applying machine learning algorithms to financial portfolio optimization.

Inate.ai automates the analysis of growth stage start-ups, using artificial intelligence to facilitate venture capital due diligence. It plugs into the common tools that startups use, seamlessly merges that data, applies AI algorithms that have been trained by subject matter experts and provides clear, actionable insights, warnings and suggestions.

We talk to Phillip about his journey from the oil and gas industry to tech start-ups. He details the importance of incubators such as Y-Combinator and the DMZ, growing companies with data-driven insights, and the current state of Venture Capital.

This was an incredibly loaded conversation with so many insightful learnings, that we hope you enjoy!

Timestamps

4:00 - Journey from Engineering to Tech Start-Ups

10:30 - How to Use Data for Useful Insights

14:55 - The Business Model of a VC

21:47 - What is Product-Market Fit?

26:40 - How to Connect with Potential Investors/VC’s

35:50 - Accurately Evaluating Start-Ups

36:54 - How Is inate.ai Helping Founders & Start-Ups

44:00 - Lightning Round

Episode 53 is about money in sports - more specifically, everyone’s favourite word, taxes!

When we look at the business of sports, it’s easy to get fixated on the glamorous life of athletes, player contracts, sponsorships, and lifestyles of these individuals. However, when we take a step back, the owners behind many of these teams tend to be the big fish that remain hidden.

This episode will uncover some of the secrets employed by these owners, and will use details from the analysis performed by a Propublica article titled: The Billionaire Playbook - How Sports Owners Use Their Teams to Avoid Millions in Taxes.

We hope you enjoy!

Episode 52 is with Professor Karl Moore!

Professor Moore is an award-winning teacher, researcher, and an internationally recognized leader in the study of Introvert/Ambivert/Extroverted Leaders. He has interviewed thousands of CEOs, Premiers, Cabinet Ministers, and even Prime Ministers.

He holds an MBA from USC, a Masters from Oxford University, and a PhD from Schulich School of Business. He is currently an Associate Professor at McGill University, a Columnist for Forbes Magazine and the Globe and Mail, and Host of the CEO Series on Bell Media.

We speak to Professor Moore about his research on Introverted, Extroverted and Ambivert leaders, and how different generations have adopted these skills. He explains the consequences of generational mixing in the workplace and how boomers, millennials and Gen z can successfully co-exist. He also details his work on Indigenous communities and how we can use current events and education to foster these relationships.

This was such an insightful and inspirational conversation that we hope you enjoy!

Timestamps2:23 - Background, Education & Research

3:30 - What is an Ambivert?

7:57 - Are you born an Introvert/Extrovert/Ambivert?

11:00 - Modern vs. Post-Modern World View

13:58 - Remote Work - Boomers Vs. Millennials

19:28 - Rise of an Anti-Social Society

24:30 - Strategic Frameworks & Porter’s 5 Forces

30:51 - Strategy Advice for Future Leaders

33:30 - Boomers, Millennials, Gen Z & Organizational Culture

37:20 - Importance of Networking

41:30 - Indigenous Relations in Canada

46:30 - Closing Remarks

Episode 51 is on Identity Politics!

In recent years the weaponization of identity politics has wreaked havoc on Western societies and is becoming more prevalent.

Aman and Sheriston break down the ideology, how it has been utilized by the powers that be to the detriment of citizens, and what we can do to break the trend. The boys also dive into the recent revelation of condo developers buying up swaths of single family homes to repurpose as rentals. They detail how rise of remote work is influencing geopolitics while exacerbating the housing crisis.

This is a passionate analysis of current events that's sure to step on some toes, so you've been warned!

We hope you enjoy!

Timestamps

0:38 - Core Developer controversy

5:00 - Morality of the Housing Crisis

10:40 - Identity Politics

19:30 - How remote work is influencing Geopolitics

Episode 50 is with Abdullah Snobar!

Abdullah is the Executive Director of the DMZ and the Chief Executive Officer of DMZ Ventures.

Ranked as one of the top university-based tech incubators in the world, the DMZ provides a launchpad for founders to build and scale fast. To date, the DMZ has helped more than 400 startups raise over $1B in capital and created 4,000+ jobs.

We talk to Abdullah about his non-traditional journey into tech. He details his journey from a Palestinian immigrant, to serving in the Canadian Armed Forces, to founding a non-profit in Kenya, to today becoming recognized as one of Canada’s Top 40 under 40.

This was an incredibly inspirational conversation that intertwines so many facets of culture and society. We hope you find it as enlightening and informative as we did!

Timestamps

2:50 - Immigrating & Adapting to Canada

7:12 - Attraction to the Hospitality Industry

10:53 - Canadian Military Experience at 16 years old

13:12 - Overcoming Fear

14:45 - The Supa Maasai Foundation in Kenya

25:12 - The DMZ at Ryerson University

31:37 - DMZ’s $1 Billion Milestone

36:25 - Why you should choose The DMZ

38:55 - Growing the Canadian Tech Ecosystem

43:45 - Common Qualities of Successful Founders

47:40 - Lightning Round

Episode 49 is with Davina Kaonohi, Co-Founder & CEO of Element Apothec!

Element Apothec is an innovative and purpose-driven consumer brand focused on CBD wellness & body care products. It was established with one goal in mind: to create a line of natural and organic, CBD-infused skincare and wellness products which combine the healing powers of nature with the ingenuity of innovation.

The journey began a decade ago, when one co-founder — afflicted with eight auto-immune disorders — started creating custom body care blends that eased her pain, nourished her skin and helped her feel better. Today, Element has expanded to more than 40 products, including lotions, body butters, roll-ons, tinctures and supplements.

We speak with Davina about her journey in the Cannabis and CPG space, how CBD has changed her life and that of her customers’, and how she successfully built her brand and online presence. We hope you enjoy!

Timestamps3:00 - Which is better - Retail or D2C?

5:25 - How to pitch your business to retail partners

8:10 - Challenges of Retail vs. D2C

11:24 - The Founding story of Element Apothec

17:14 - The Benefits of CBD

20:26 - The CBD Industry Is Just Starting

27:42 - What Makes a Great Brand Strategy?

35:18 - Importance of Feedback and Networking

39:37 - Lightning Round

Episode 48 is with Brennan McEachran!

Brennan is the Co-Founder & CEO of Soapbox, the app built for managers.

Managers are the most unsupported and under resourced individuals in corporate organizations and the consequences of this are dire. Bad leadership trickles down into teams, company culture, and eventually the overall performance.

Soapbox is the first software platform designed to help managers prioritize their people and performance while coaching good management habits. It manages meetings, tasks, and goals, all while providing constructive feedback and relevant engagement tools to give employees a voice.

We sit down with Brennan to discuss his founding journey, the traits and habits of a good manager, and how you can become a better leader in any situation, not just work. This was a really insightful conversation that we hope you enjoy!

Timestamps

2:23 - What is Soapbox?

12:47 - How Soapbox helps managers & teams

21:44 - How to Share Your Vision With and Lead a Team

28:05 - The Lettuce Pact

32:11 - What Makes a Good Leader

40:16 - Giving/Receiving Feedback as a Manager

50:35 - The Future of Work & Soapbox

58:25 - Lightning Round

Episode 47 is all about pre-nuptial agreements and marriage!

Numbers don't lie - almost half of all marriages end in divorce. But what about the numbers that come up during the divorce?

Aman and Sheriston break down some strong, controversial opinions on divorce laws and pre-nups using some famous examples of the past and present. Given the topic, this conversation is wild from start to finish, so consider yourself warned!

We hope you enjoy!

Timestamps

0:46 - Intro from "Flagrant 2 Podcast"

3:03 - Britney Spears

5:00 - Benefits of a Pre-Nup

8:30 - Dr. Dre

Episode 46 focuses on the hottest thing in the economy right now - real estate.

The housing market has been on fire this past year, with supply shortages and pandemic activity driving prices to record levels, month after month with no signs of slowing down.

Aman and Sheriston break down how we found ourselves in this situation, what you should do with your finances in the interim, and what to expect in the post-pandemic housing market.

For an added bonus, the video version on YouTube will include a segment where we show examples of houses for sale across the country, so make sure to check that out as well!

Timestamps1:46 - Factors driving the housing market

7:21 - What to expect after the pandemic

8:32 - New Canadian Mortgage Rules

13:30 - Should you invest in real estate right now?

Episode 45 is with Dan Park.

Dan Park is the CEO of Clutch Inc., a tech company reinventing the way people buy cars through e-commerce. With a completely virtual showroom, you can browse, get prequalified for and order a vehicle that will be delivered right to your home, which you can return within 10 days. Before Clutch, Dan was the General Manager of UberEats Canada where he helped launch the food delivery platform in Canada. He also has an extensive background in venture capital as both a VC and entrepreneur.

We talk to Dan about he helped make UberEats the staple of fast food delivery in Canada and now how he’s reshaping consumer mindsets in car buying. He also details the experience of being on both sides of the VC table.

We had a blast with this one, so we hope you enjoy!

Timestamps

2:11 - UberEats Canada’s First General Manager

4:00 - How UberEats Works

9:05 - Creating Successful Business Partnerships

12:15 - How to Develop Out a Marketplace

14:25 - How Clutch is Solving the Traditional Car Buying Process

21:50 - Test driving is unnecessary, here’s why

25:45 - Inspiration from Tesla

27:35 - Being a VC vs. Pitching to a VC

34:55 - Most Common Mistake during VC Fundraising

38:20 - Success Factors of a Founding Team

47:00 - Lightning Round

Episode 44 is with Erica Rankin aka The Cookie Dough Girl.

Erica is the Founder and CEO of Bro Dough, Canada’s first 100% plant-based, protein-infused, edible cookie dough. Having launched her business in late 2019, Erica is the epitome of an entrepreneur, working out of a commercial kitchen rented by the hour, storing inventory in her living room, and even packing orders at her dining room table as they come in.

We sit down to chat with Erica about her story launching the brand, how she uses LinkedIn and TikTok to blow up her online presence practically for free, and the ins and outs of running a business. We hope you enjoy!

Timestamps

2:00 - What is Bro Dough?

4:00 - The Production Cycle

7:46 - Menu Creation - the weirdest flavour requests!

10:50 - Importance of Networking & Mentorship

13:36 - A Typical Day @ Bro Dough

15:25 - Managing Mental Health as an Entrepreneur

19:10 - Brand Strategy & Social Media Marketing

24:20 - Motivation for Entrepreneurship

28:25 - Lightning Round

Episode 43 is with Mohsen Omrani and Sarah Rennick.

Mohsen is the CEO & President of OPTT, a digital health start-up that provides behavioural health providers the tools to build an affordable, online mental health clinic powered with AI. Sarah is the Co-Founder and CEO of Alli Therapy, an online therapy portal for parents when they need it, in the way they need it.

The need for mental health professionals has been on the rise for decades, but has now skyrocketed due to the ongoing global pandemic. Credible, reliable online resources help tackle this issue while navigating the tech landscape to extend their reach. So, how did they do it?

We speak with Mohsen and Sarah about their respective journeys in the field of mental health. They detail what lead them to studying the brain, how their companies are solving the next crisis we’re currently faced with, and what you can do every day to address your mental health.

We hope you find this conversation insightful, informative, and most of all, helpful.

Timestamps3:05 - The Culture Shift around Mental Health stigma

6:34 - Why Employers should invest more into mental health support

10:35 - Mohsin’s journey into the mental health field

13:19 - Sarah’s journey into the mental health field

16:05 - Relationships, Parenthood, & Mental Health

21:50 - Machine Learning & Artificial Intelligence in Mental Health care

31:24 - Mental Health during the Global Pandemic

33:30 - The “Fourth Wave” of COVID-19 to come

36:50 - Baby Boomers, Millennials, & Gen Z

42:03 - Lessons from Ryerson University’s DMZ incubator

49:45 - Lightning Round

Episode 42 is with Ruben Harris, Co-Founder & CEO of Career Karma!

Career Karma is the easiest way to find a job training program online, matching people with the right coding bootcamp and supporting them throughout their careers. With over 150,000 members, 9,000 bootcamps and trade schools, Career Karma is on a mission to help 1 billion people.

Ruben is a Bay Area transplant from Atlanta, Georgia who switched from investment banking to tech after writing a viral blog post called Breaking Into Startups about how he moved to San Francisco without a job and landed a position 3 weeks later. Due to popular demand, he then co-founded the Breaking Into Startups Podcast to demystify the process and went on to build Career Karma with Artur and Timur Meyster.

We talk to Ruben about his journey through professional and personal development. He details the Y Combinator experience, how to build a community, and explains the importance of mastering your own psychology. This was an insight-packed conversation that we hope you enjoy!

Timestamps2:20 - Life-long learning & the future of education

7:50 - Limiting mindsets in minority/oppressed communities

11:05 - Importance of Mentorship

15:13 - Ruben’s career journey from school, to investment banking, to tech

21:00 - How to build a community: Blue zones, “Moai”, and positivity

28:17 - Parties in Atlanta & Celebrity Marketing

31:35 - The future of Career Karma

34:00 - The Y Combinator Experience

40:51 - Lessons from Y Combinator

46:38 - How to build a strategic vision

51:30 - Self-Confidence & Imposter Syndrome

57:10 - Lightning Round

This episode is sponsored by · Anchor: The easiest way to make a podcast. https://anchor.fm/app

Episode 41 is with Eliot 'The Fire' Marshall!

Eliot is a former UFC Light Heavy Weight, member of The Ultimate Fighter season 8, Head Coach at Elevation Fight Team, owner of multiple Easton Training Centre facilities, a motivational speaker, a TEDx Speaker, and an all-around good guy.

He has successfully transitioned his career from professional fighter to business owner, but if you ask him he says he’s just a product of luck and hard work. So we sit down with Eliot to discuss his journey. He details his bouts with anxiety in a dangerous career, the importance of knowing yourself, and how he was able to pivot away and succeed despite the odds.

This was an incredibly inspiring conversation, so let’s get right into it!

Timestamps3:00 - How Eliot got into Martial Arts

6:19 - How much of his career he attributes to luck

8:30 - The Egg Lottery

9:40 - There is no such thing as a self-made man

11:05 - Seeking acceptance

16:30 - Transitioning away from fighting

19:10 - Burt Watson, the Babysitter to the Stars

29:06 - Fear, Emotions, & Masculinity

35:08 - Never tie your dollars to your hours - make your money work

44:24 - Speak to one person at a time in everything you do

48:40 - What do you want to be remembered for?

50:30 - Lightning Round

Episode 40 is with Colin Chartier, Co-Founder and CEO of LayerCI!

LayerCI is the DevOps platform for distributed software teams. Their web application enables the highest performing software developers to preview full stack environments for every commit and have a centralized CI/CD stack.

Going against the typical path of graduates heading to big tech firms, Colin decided to build a business of his own with co-founder Lyn Chen in Toronto to help developers ship code faster. Last year, LayerCI raised a pre-seed round from Y Combinator, followed by over a million dollars in investment from multiple Silicon Valley firms.

We sit down with Colin to learn how LayerCI is helping businesses, in simple terms, no engineering knowledge needed. He breaks down how you can accelerate your capacity to learn, the process of being chosen by Y Combinator, and the skills that students and young entrepreneurs in this field should focus on.

This was a really insightful conversation that we hope you enjoy!

Timestamps2:00 - How to prioritize key tasks amongst a team

4:04 - Attracting talent & hiring strategies for start-ups

9:45 - How gaming taught Colin to program

14:24 - How to accelerate your learning

16:17 - Skills that students/young entrepreneurs should focus on today

19:52 - How LayerCI helps developers and businesses (simplified)

26:38 - Getting into Y Combinator and working with accelerators

35:21 - Lightning Round

Cannabis. Hemp. Weed. Marijuana. Mary Jane. Devil's lettuce. The Greens. The list goes on. But have you wondered why we have an endless list of names that we use for this plant just to get around the law? It's time to talk about the truth.

Legalization is slowly crawling its way through states while federal decriminalization is still outstanding. But, how did we even get here to begin with?

This week’s episode will explore the real reason cannabis was made illegal, the politicians and bureaucrats involved, and how that decision has shaped the country we know today and the industries that drive its economy.

Racial tension, political turmoil, corruption, lies, and media embellishment. All this just for a little puff-puff-pass?

Puff-puff-click play!

This episode is sponsored by · Anchor: The easiest way to make a podcast. https://anchor.fm/app

Episode 38 is with Josh Domingues, founder and CEO of Flashfood!

Flashfood is a mobile platform that connects surplus food from grocery partners directly to its users at reduced prices to alleviate food waste. Solving food inequality and food waste is a tall order but the company is well on its way to becoming a household name across North America, with partnerships with Loblaws, Farm Boy, and Meijer.

We sit down to speak with Josh about the journey behind the business. He explains the economic and environmental impacts of food waste, the challenges of food inequality, and how he built Flashfood to where it is today. He also breaks down the many ways through which we can reduce our own food consumption and waste every day.

This was an eye-opening conversation that really exposes many secrets of the food industry. If you’re looking to save money on your grocery bill, click play and consider downloading Flashfood from your app store!

Timestamps3:10 - The idea behind Flashfood

4:46 - Terrifying Food Standard & Food Waste Stats

8:35 - Best before dates are fake, here’s why…

12:40 - How to reduce your food waste right now

14:06 - What is Flashfood and how are they helping consumers

16:05 - The issue with the Canadian Grocery industry

21:00 - The future of Flashfood

26:47 - The importance of trusting the founding team

29:10 - “We don’t know who developed our app…”

40:20 - Company vision & celebrating small milestones

42:49 - The one thing that fuels start-up growth

48:15 - Lightning Round

Episode 37 is with Gethin Ellis, Founder of Gethin Ellis Coaching & Nutrition!

Gethin is a chef based in Wales who left the apron behind to pursue his passion as a Nutritionist and Personal Trainer. In a matter of years, he has completely transitioned his career to work with high profile athletes at the top of their game. With clients like Darren Till and Robert Duran Jr., Gethin is making a name for himself in the fitness space and is only getting bigger.

So we sit down for a chat to hear about his journey. He explains how he successfully pivoted his career into the fitness industry, the pros and cons of various diets in the news, and the dangers of the supplement industry. We also discuss the harmful effects of social media on body positivity and mental health.

This was a really informative episode, so much so that Gethin secures one of us as a client during the actual conversation! If you’re looking to understand how to become the best version of yourself, then click play.

Timestamps4:15 - Journey from Chef to Nutritionist to Personal Trainer

9:45 - Approaching and Securing a Client

13:00 - Weight Cutting in Sports

18:00 - Competition and negativity in the Fitness space

20:35 - Should Gyms stay closed or re-open?

27:30 - Coaches need coaches too

33:00 - Diets: Keto, Intermittent Fasting, and Vegans

38:16 - Dangers of the Supplement Industry

42:05 - Social Media & Body Positivity

55:00 - Lightning Round

Episode 36 is with Nick Saltarelli, one of three Co-Founders of Mid-Day Squares!

Mid-Day Squares started with Lezlie Karls, Nick’s wife, creating homemade fudge bars to solve their afternoon cravings while also keeping the junk away. What started as a home experiment became the seed for an incredible business idea. Today the company has sold over a million units and is available in grocery stores across the country!

We sit down for an unfiltered, uncensored, free-for-all chat with Nick to hear his take on the journey thus far. He talks about how they grew the business in one of the most saturated industries on the market, how they manage their work/family relationship, and how being your authentic self is the key to success.

This was a fun chat with so many gems throughout, so grab a snack and enjoy!

Timestamps2:37 - The story behind Mid-Day Squares

8:57 - Competition in the Food Industry

12:32 - The series of “Aha!” Moments

15:20 - The best lessons that led to Nick’s success

18:29 - How to successfully work with family members

21:58 - Importance of a Business Coach/Therapist

25:40 - Creative Direction by Lezlie Karls, Branding by Jake Karls

26:54 - The big difference between Marketing & Branding

33:10 - Building trust in your team

44:22 - Lightning Round

Episode 35 is with Marie Chevrier Schwartz, Founder & CEO of Sampler!

A proudly Canadian, venture-backed technology company, Sampler is the leader in digital product sampling. Their software helps hundreds of brands like Nestlé, L'Oréal and Kimberly-Clark make their product sampling strategies targeted and measurable. Their approach builds a personalized product sampling experience that gets samples straight to your doorstep and continues to provide better products as they get to know you more.

We sit down with Marie to understand how her early days of handling out samples led to the business idea. She explains her bouts with corporate burnout and how company culture can help keep employees happy and healthy. She also talks about the importance of networking and leveraging the power of people.

This was a great conversation with an innovative leader transforming the retail experience, so we hope you enjoy!

Timestamps

2:30 - The importance of company culture

7:35 - How leaders can help keep employees happy and healthy

11:30 - Marie’s story of dealing with corporate burn-out

16:19 - How to identify and address burn-out in the workplace

21:30 - How Sampler is connecting consumers and brands with samples

24:57 - The future of Sampler

28:25 - Retail TO and Toronto’s retail ecosystem

31:30 - Your network is the gift that keeps on giving

33:30 - Lightning Round

Episode 34 is with Hongwei Liu, Co-Founder & CEO of MappedIn!

Headquartered in Waterloo, Ontario, MappedIn is the leading platform for indoor spatial data management, digitizing venues, and building best-in-class indoor mapping experiences. They are at the forefront of the collision between tech and brick-and-mortar, having mapped over 500 million square feet of indoor space in over 30 countries.

MappedIn grew from a simple project between friends, to serve shopping malls around the world, theme parks such as Dreamworld, and even the Department of Homeland Security.

We chat with Hongwei about the idea behind MappedIn, the challenges of growing a startup as a young entrepreneur, developing leadership skills, and his philosophy of doing things that don’t scale. We hope you enjoy the show!

Timestamps

2:45 - Building a business while in school

11:20 - Why you should work at a start-up

20:17 - The idea behind MappedIn

30:35 - Leadership skills for young entrepreneurs

34:22 - Finding the right people for your business

40:33 - Do things that don’t scale

44:50 - Lightning Round

Episode 33 is with Alisha McFetridge, Co-Founder & CEO of RainStick Shower!

RainStick is a unique recirculating system that saves 80% water and 80% energy but feels like a high-pressure shower. By using robust filtration, RainStick provides a relaxing, safe and cleansing experience.

Water demand is projected to grow by 30% over the next 30 years as the world’s population is expected to grow by more than 2 billion people by 2050. That is an incredible amount of stress on freshwater resources and infrastructures in society. This is where RainStick Shower hopes to challenge the status quo. Their mission is to combat climate change and build a circular economy in Canada by transforming how we use water.

We sit down with Alisha as she explains how she co-invented RainStick, the engineering behind the shower, and the importance of addressing the global water supply.

Timestamps

3:06 - What is RainStick & How does it work?

9:30 - What if people pee in the shower…

10:29 - Technical Requirements

12:00 - Shower technology has not had innovation since 1810

16:14 - Sustainability sells the brand, but not the product

23:42 - The issue with water supply in North America

26:20 - Is water a private good or public good?

29:45 - The Canadian Tech scene

34:40 - RainStick’s launch this year

36:06 - Lightning Round

Episode 32 is with Dr. Sarah Saska!

Dr. Saska is the co-founder and CEO of Feminuity, a management consulting firm that helps companies build diverse teams, equitable processes, inclusive products, and cultures where people belong.

Before founding her company, she led pioneering doctoral research detailing the need for technology and innovation that is equitably and ethically designed. She has delivered TEDx and keynote talks around the globe and was named amongst WXN Canada’s Top 100 Most Powerful Women in 2015 and 2017.

We sit down with Dr. Saska as she details the importance of diversity and inclusion in today’s world. She highlights the issue of representation at the C-suite level, political correctness, and the need for an intersectional view of individuals.

This was an incredibly informative conversation that sets the bar for 2021, the year of accountability as she puts it. We hope you enjoy!

Timestamps

2:30 - The importance of Diversity & Inclusion (D&I)

13:20 - How is Feminuity addressing D&I in the workplace?

15:50 - How to approach sensitive topics with organizations/employers

23:07 - The lack of diversity at the C-Suite level

27:20 - Polarization of Gender Pronouns

33:27 - Dealing with Employees that reject D&I

40:17 - Lightning Round

Welcome to episode 31 of the Generation Hustle Podcast!

This week we're introducing a new segment where we cover important topics and hot button issues in the news.

We kick it off with the never ending student debt crisis. Joe Biden advocated for universal student debt relief on his campaign trail which is still to be approved. But is a blanket forgiveness a good idea?

Speaking of Presidential decisions, how about Donald Trump adding a section on UFOs in the latest COVID relief bill? (Yes, we fact checked that). And if that doesn’t have your conspiracy gears grinding, boxing fans have reignited a debate on time travel due to footage from a 1995 Mike Tyson fight that appears to show a man with the latest Android phone in the crowd.

This episode was a wild ride from start to finish, so be sure to listen to the method behind our madness!

Timestamps

1:25 - What is worth the value of 9 Elon Musks?

8:00 - The reason university/college become so expensive from the 1980s

16:00 - Joe Biden campaigned on student debt relief. Is this a good idea?

22:30 - Trump's COVID relief bill includes comments on UFOs...

34:00 - The Time Traveller from Mike Tyson's fight

Episode 30 is with Jyothee Murali!

Better known by her brand, JYXDI, Jyothee is a self-taught visual artist based out of Toronto. Against societal odds as well as traditional South Asian cultural norms, Jyothee dropped out of school and nurtured her passion for painting into a full-fledged career.

In a matter of years, she has grown her personal brand exponentially, collaborating with high-end clients such as 6LACK, OVO, XO, and COACH. Her art ranges from realism, portraits, landscapes and custom fan pieces, with an interest in anime.

We chat with Jyothee as she details her venture into art, her growth strategies, and the importance of prioritizing passion over profits. We hope you enjoy the show!

A former varsity basketball player, Randy Osei traded in his jersey for sports marketing and is the Founder & CEO of Rozaay Management, a creative marketing and talent management firm. He is also the Executive Director of the Athlete Technology Group, an events and media company that connects tech entrepreneurs and athletes.

Technology has transformed the way we market and brand ourselves. Talent agencies are constantly shifting to adapt to the world of today in order to connect athletes to their fans and business opportunities that will allow them to prosper past their sport.

Rozaay Management has evolved form a sports management agency to a prominent social enterprise having worked with high-profile clients like Anthony Bennett, Giannis Antetokounmpo, Andrew Wiggins, and more.

We sit down with Randy to explore the world of athlete management. He explains his strategy to building long lasting, organic relationships, breaking down the knowledge barriers that athletes are faced with, and how he’s leveraging tech to establish perpetual revenue streams for his clients. If you’re looking for creative branding techniques, this episode is a must listen!

Timestamps

2:15 - Transitioning from Athlete to Managing Anthony Bennett

7:30 - Social leverage and the power of connections

9:10 - Curating your brand

16:55 - Biggest mistake athletes make with media

24:34 - The Rich Paul Rule

30:30 - Why athletes struggle with money management

34:40 - Athletes and the Tech Industry

Cody and Cole Hock are co-founders of Up North Management Group.

The creator economy is booming, with creatives across various social platforms gaining popularity and business opportunities at scales we have never seen before. However, these individuals are not always equipped with the knowledge and expertise to navigate the technical landscape of monetizing a platform. This is where Up North thrives.

Up North Management Group is a leading talent management firm representing top gaming and esports creators and streamers, and professional athletes with a passion for the digital space. They have partnered with brands such as Samsung, Nesquik, LG and Oculus, while representing high profile clients like Nasher, Inkslasher, NoisyButters, among others.

We sit down with Cody and Cole to discuss their journey in talent management. They detail how they started their firm, how they help clients maximize their platforms, and common pitfalls of creators who are mismanaged. If you’re looking to learn how to take your talents to the next level, this episode is for you!

Timestamps

2:30 - Starting a Talent Management Agency

8:05 - Common pitfalls of creatives

10:25 - What makes a good Agency fit?

16:07 - How the industry can take advantage of creators

20:42 - Creating leverage as a creator

24:41 - Brand building & Partnering with Nasher

35:30 - Esports & Drake x Ninja

43:40 - Networking Skills to get your foot in the door

51:35 - Lightning Round

Kyra is a Canadian born footballer who started from Toronto and took her talents to Howard University in Washington to pursue athletics and health sciences. Though she had no intention of a pro career, she was quickly noticed by the Saint Kitts & Nevis Women’s National team and brought on as their goalkeeper and captain.

Today, Kyra serves as the CEO for healthcare consulting firm, Persimmon Group while continuing to train and educate young athletes as a mentor and coach.

We sit down with Kyra to discuss her journey through athletics and healthcare, the culture shock of playing abroad, and the mentality of athletes representing their country. We hope you enjoy!

Timestamps:

0:25 - Discovering the sport of soccer

3:30 - Getting noticed by the National Team

7:21 - Representing your country and pre-game nerves

11:20 - Mentorship and Leadership

17:00 - Game Day routine

18:57 - Diet and Nutrition

20:50 - Persimmon and Healthcare Consulting

23:30 - America vs Canada - Culture Shock

30:13 Lightning Round

Travis is the Co-Founder and CEO of Knowledgehook, an instructional guidance system designed to professionally develop teachers and students. Their proprietary technology can uncover learning insights from assessment data that helps bridge the gap between student needs and teacher capabilities.

Having recently raised over $20M, Travis and team are ready to scale the business to new heights. We talk with Travis about how he views growth, how to sell to government organizations, and where the future of online learning is headed. We hope you enjoy the first episode of the year!

Timestamps

2:00 - Intro, Midlife Crisis, “The Dip”, and personal development

19:00 - How Knowledgehook is helping students and teachers

28:00 - The Sales Cycle of selling to government

38:48 - How did Google and Facebook become ad giants?

53:00 - Understanding the Buyer - How to sell a power drill to someone who doesn’t know what a screwdriver is

1:02:30 - Future of the education business model

1:15:50 - Determining your competitive strategy

1:23:00 - Lightning Round

Buster Scher is the founder of HoopsNation. At a young age, Buster knew he wanted to be a broadcaster. Throughout his high school years, he experimented with various outlets before deciding that he wanted to carve out a niche for himself in fantasy sports - enter Hoops Nation.

Hoops Nation started as a fantasy basketball page when Buster was 15 years old. Within a couple years, Buster found himself surrounded by like-minded creatives and brands alike. Buster would go on to partner with Dunk, Atlantic, Overtime, and Vayner Media, run by everyone's favourite Gary Vaynerchuk.

Today, Hoops Nation has over a million followers, while Buster continues to build onto his brand with the Buster Show, his personal podcast with athletes and celebrities. We talk to Buster about scaling up your brand, how to strategize your digital presence, and his experience interning at Vayner Media. Click play to start building!

Timestamps:

2:00 - How HoopsNation started

6:00 - How to build a successful brand

13:17 - There are no such things as mistakes

14:25 - Working with Gary Vaynerchuk

16:30 - Try every platform to serve your niche

22:56 - HoopsNation, CardsNation, and The Buster Show

This episode is sponsored by · Anchor: The easiest way to make a podcast. https://anchor.fm/app

Josh Solomon is the Director of Enterprise Sales at Ada Inc. Ada is an AI-powered platform that enables businesses to drive an incredible customer experience through scalable automation. Josh has built his entire career in sales, a field so important that he suggests a good sales professional is able to transfer their sales skills into life skills.

We ask Josh about his journey through sales and dive into his philosophy around sales skills that are transferrable to life. He walks us through the important steps that sales professionals should understand, from nurturing a lead all the way to securing a customer. We also discuss how Ada’s platform helps businesses and dispel the negative connotation around “chatbots”.

Whether you want to become a better salesperson or want to learn must-have skills for your own personal development, this episode is for you! So sit back and listen to Josh sell us that pen.

Timestamps

2:00 - It all starts in your head

8:15 - How to build rapid progress

11:25 - Get yourself out of comparison mode

15:20 - The Sales Industry and Ada Inc.

20:30 - How to become a better salesperson

31:27 - Sales is a dirty word

34:52 - Advice to new salespeople

44:20 - How Ada is helping businesses

50:40 - Josh’s life-changing event

53:40 - Lightning Round

This episode is sponsored by · Anchor: The easiest way to make a podcast. https://anchor.fm/app

Andrew is the founder of Flourish Pancakes, whose protein pancake mix has taken the Canadian breakfast industry by storm.

Flourish aims to reimagine breakfast with the belief that eating healthy shouldn’t be a chore. Improving eating habits can be achieved by transforming indulgent foods to fit your lifestyle. No elaborate prep or complicated instructions - just pure, organic, natural ingredients tastefully brought together in a simple way.

Andrew takes the time to share his journey of building an alternative healthy food brand loved by consumers in an ever changing and hard to please industry. He leans in on his experience of working with Arlene Dickinson from Dragon’s Den and how her fund, District Ventures, has helped scale Flourish to the next level.

So sit back, relax, and enjoy the show - maybe over a fresh stack of pancakes?

Timestamps

1:40 - Andrew’s journey to founding Flourish

5:15 - What was the first company name?

7:23 - Flourish Pancakes’ pricing strategy

12:20 - How Andrew came up with the pancake recipe

22:03 - How to get consistent repeat customers

26:10 - Businesses should compete on employee satisfaction

28:50 - Health Tip: Stay away from Big Brands

35:45 - Working with Arlene Dickinson

43:20 - Lightning Round

This episode is sponsored by · Anchor: The easiest way to make a podcast. https://anchor.fm/app

Venture for Canada (V4C) is a not-for-profit organization with a mission to foster the entrepreneurial mindset and skills of young Canadians. The organization envisions a Canada where the youth can equitably realize their potential to build the most prosperous place in the world.

The organization achieves this through an internship program for post-secondary students and a fellowship program for graduates that help train the necessary skills and knowledge to succeed in the entrepreneurial ecosystem with likeminded peers.

In 7 years, VFC has grown from an idea to a national charity with 20 staff members, a multi million dollar budget and more than 5000 community members and alumni.

We talk to Scott about how he brought this idea to life, what the VFC programs have to offer, and how today’s education system fails to prepare young graduates for the business world.

If you’re looking to jumpstart your next big idea, have a listen and see if Venture for Canada can help you!

Timestamps

1:50 - How Scott came up with Venture for Canada

4:35 - The skills of a successful entrepreneur

7:10 - Not all feedback is good feedback

11:20 - V4C’s Fellowship Program

16:50 - Why graduates struggle with landing jobs

22:53 - How to run a non-profit organization

30:20 - Is Canada creating the next Silicon Valley?

36:45 - A fourth industrial revolution

39:15 - Lightning Round

Hush is a company on a simple mission - to help people around the world relax with ease and fall asleep faster whenever they wish.

Almost every scientific study nowadays indicate that insomnia, stress, and anxiety levels have been on the rise for years. Sleep and relaxation are really important to managing these stressors. Hush’s weighted blankets apply evenly distributed pressure that is proven to reduce anxiety and cortisol. This firm, deep pressure stimulation is known as Deep Touch Pressure Therapy that acts like a hug.

We talk to Aaron about how he started the company with co-founder Lior Ohayon. He explains their growth strategies, their amazing pitch experience on CBC's Dragon’s Den and the science of weighted blanket therapy. Aaron also leans in on his entrepreneurial spirit and what drives him to bet on himself and succeed.

So wrap yourself in your coziest blanket and click play to hear more about how Hush’s products can help you get better quality rest. And if that blanket isn’t cozy enough, maybe you want to check out Hush?

Timestamps

1:40 - How Hush blankets started

7:50 - How to succeed at anything

11:55 - Why you should use weighted blankets

16:00 - Hush’s new cold blanket

19:20 - Hush’s business strategy - don’t be attached to the business

27:50 - SMS Marketing & the need to build trust with customers

36:27 - Why supply chain and fulfillment is so complex

41:00 - Philanthropy in business - Hush’s give back program

48:25 - The legendary Dragon’s Den experience

53:35 - Lightning Round

This episode is sponsored by · Anchor: The easiest way to make a podcast. https://anchor.fm/app

Independently owned and operated, Great Lakes Brewery (GLB) is celebrating over 30 years in the craft beer business, making them one of the oldest craft breweries in Ontario! They specialize in producing flavourful beers that are sure to awaken your taste buds with each sip. From unique seasonal ales, bottle conditioned releases, year-round ales and premium lagers, GLB produces a variety of products to be enjoyed by everyone!

We talk to Troy Burtch, the Marketing and Communications manager, about his journey into the beer and spirits world. He details the importance of local breweries and how they compete in the ever popular craft beer space. Troy also explains the amazing pivot that GLB made at the start of the pandemic where they recalled their beer kegs and began producing hand sanitizers to support the community.

GLB is a true success story, starting out of a strip-mall in Brampton, Ontario to becoming one of Canada’s most beloved and recognized craft breweries. We hope you enjoy this fun conversation and highly recommend you crack open a cold one before you hit play!

Timestamps

2:20 - The story behind Great Lakes Brewery

11:58 - What is a craft beer/brewery?

17:00 - GLB’s Marketing strategy

26:32 - Why this generation loves and prefers craft beer

30:27 - Forming connections with customers

32:15 - GLB’s pivot from beer to hand sanitizers

43:10 - Lightning Round

This episode is sponsored by · Anchor: The easiest way to make a podcast. https://anchor.fm/app

Hayley Wickenheiser is a 6x Olympian, 4x Olympic Gold medalist, Canadian hockey legend, angel investor, and soon to be doctor in the later stages of her medical degree.

Hayley now serves as Managing Director at Pandemic Solutions, a medical consulting company that helps small, medium and large enterprises with organizational support in uncertain times. Dr. Shaw is the President and Director of Medicine at Pandemic Solutions.

We talk to Dr. Shaw and Hayley about viral transmission and the development of a vaccine for the current pandemic. They walk us through the services offered by Pandemic Solutions and how they’re helping businesses re-open safely during this uncertain climate. Hayley and Dr. Shaw also detail how their unique backgrounds have helped each other learn and grow along this journey. We hope you enjoy the show!

Timestamps

1:43 - Viruses transmission and effects on the body

3:35 - Update on the COVID-19 vaccine trials

6:10 - Pandemic Solutions - Who are we & what do we do?

14:00 - The future of contact tracing

19:10 - Hayley’s transition from hockey to medicine

25:39 - Lightning Round

This episode is sponsored by · Anchor: The easiest way to make a podcast. https://anchor.fm/app

Jeff is the Founder and President of Kimurawear, a leader in quality and innovative products in the martial arts community. Founded in 2006 from Brampton, Ontario, Kimurawear began creating training equipment for professional athletes of various disciplines. With their unique approach of forward thinking and attention to detail, the brand took over the MMA scene, featured on UFC stars such as Donald “Cowboy” Cerrone, Frankie Edgar, Thales Leites, and Jose Aldo.

Jeff has since diversified his business portfolio, expanding into the world of real estate with various cottage properties across Ontario as well as his own podcast called Jeff Knows Inc. We speak to Jeff about his journey into the combat sports world and what strategies he used to market his products to star athletes, especially before the days of social media. Jeff also explains how he pivoted from athletic wear to real estate, to his podcast. He also touches on the importance of balance in his life between work and family.

This was an inspirational conversation with a true go-getter in all sense of the word. If you’re looking for some energy to fire you up today, click play and listen to Jeff’s story.

Timestamps: 2:50 - How Kimurawear started 8:47 - Kimurawear's Growth Strategy 10:40 - Building relationships with your customers 13:15 - UFC Fighter Pay & Exclusive Deal with Reebok/Venum 20:50 - Why Jeff doesn't focus on his competitors 25:08 - The story of Jeff's son 29:26 - Transitioning to Real Estate 32:00 - Are you born an entrepreneur? 37:55 - Why you should never seek comfort 43:41 - Don't fall in love with your business 47:11 - Social Media, Perfection, & Road Trips 53:40 - Everyone has the opportunity to be great 58:50 - Lightning Round

This episode is sponsored by · Anchor: The easiest way to make a podcast. https://anchor.fm/app

Daniel Beach and Neetu Godara Rai are the CEO and CGO of SoCIAL Lite Vodka, the best vodka soda in Canada (in our opinion)! They are two of three co-founders, along with COO Kevin Folk, of the wildly popular brand.

Sounding something like a campfire tale, the idea for the company was born while mixing drinks in Kevin’s home kitchen. After spending countless summer nights mixing drinks with different fruits and flavours to accommodate the tastes of their friends, the trio realized that they were onto something special.

With 80 calories per can and simple ingredients, SoCIAL Lite drinks were the first pre-mixed vodka sodas in North America to contain no sugar! It was an instant hit!

We talk to Dan and Neetu about their motivations behind creating their own business, how a new product goes from an idea to the shelf, and their core strategies to scale the company.

This was a truly inspirational conversation with two genuine individuals. So crack open a cold can and enjoy the show! As a tip, we recommend the Pineapple Mango flavour and if you’re a fan of the podcast you understand why.

Timestamps: 2:30 - The story behind SoCIAL Lite Vodka 6:55 - How the name “SoCIAL Lite” was chosen 10:40 - How to take a product from idea to store shelves 16:45 - How the LCBO chooses its products 22:35 - Being a minority female founder in the alcohol industry 29:57 - Entrepreneurship is overly glorified 33:15 - Setbacks in the early days of the company 36:15 - Competition in the industry 39:57 - The future of hard seltzers 51:50 - Dan and Neetu on choosing the entrepreneurial path 1:00:20 - Lightning Round

This episode is sponsored by · Anchor: The easiest way to make a podcast. https://anchor.fm/app

Greg is the Founder & Head Coach at The 1440, an online, personal coaching fitness program. His journey began as a varsity football athlete at Wilfred Laurier University where he discovered his love for training.

From here, he transitioned from varsity athlete, to strength coach, to working full time at a tech startup, before branching out on his own with The 1440. The one habit that remained consistent throughout all these changes was training.

Greg preaches the importance of prioritizing fitness, showcased in the name which serves as a reminder that we all have the same 1440 minutes in a day. The onus is on us to use them wisely.

We talk to Greg about the science and psychology behind dieting and working out, and his experiences from the tech world that has helped him succeed with his fitness venture.

To quote Greg: “Your best is yet to come. Get what you came for.” So click play and get what you came for!

Timestamps

3:50 - The Story Behind “The 1440”

7:00 - How People Tend to Approach Fitness

14:45 - How To Be a Good Trainer

16:30 - Diet Trends & Why Most Diets Fail

29:00 - Working at a Tech Start-Up (Vidyard)

35:00 - What would you tell your younger self about quitting your job?

41:05 - Tech & the future of fitness

52:30 - Supplements & PEDs

1:02:00 - Transitioning away from being a varsity athlete

1:10:08 - Best story from the gridiron

1:13:00 - Lightning Round

This episode is sponsored by · Anchor: The easiest way to make a podcast. https://anchor.fm/app

Ben Feferman is the CEO of Amuka Esports, Canada’s leader in esports venues, online leagues, and tournaments. If you’re asking, “What are esports?” then this episode is for you!

Online gaming has been around for awhile, however the industry of gaming has radically shifted in the last decade. With the rise of online gaming communities and competitive leagues, the esports industry boasts more active viewers than every major sports league in America besides the National Football League (NFL). In fact, it is estimated that by 2022, the industry will be worth an estimated $1.8B! And Ben intends to have Amuka at the forefront of this growth.

Featuring two arenas in Toronto and Windsor and having organized over 300 events in esports, Amuka is determined to build a billion dollar gaming empire.

We speak to Ben about how he transitioned his career from investment banking to online gaming, his journey in the industry, how to scale gaming communities, and the possibility of esports holding a spot on ESPN. Before you quit your job and start up the Playstation, have a listen to Ben’s story!

This episode is sponsored by · Anchor: The easiest way to make a podcast. https://anchor.fm/app

Akosua Asare is the founder and CEO of Essence Luxe Couture, a luxury wig brand powered by AI that uses ethically sourced hair to create meticulously handcrafted wigs. The company mission is to help those who suffer from hair loss, while breaking down the traditional barriers to entry for minorities in the beauty industry.

At the age of 21, Akosua developed alopecia, a condition where the immune system attacks hair follicles, leading to hair loss. Akosua immediately recognized the disconnect in the industry - custom wigs are expensive and limited to standard styles, colours, and head sizes, with no “trying on” process so to speak. So Akosua channeled her experience into an opportunity.

Today, Essence Luxe Couture creates custom wigs based on your specifications and is looking to expand this function with proprietary AI-technology. The end goal is to create an immersive experience in which you can virtually try on wigs of all shapes and colours, all from the comfort of your home.

We talk to Akosua about her journey building the company, her experience as a female, black founder in the tech space and the future capabilities of artificial intelligence in the beauty industry.

3:24 - Akosua’s story and the beginning of Essence Luxe Couture 12:39 - Disrupting the beauty industry with Artificial Intelligence 18:21 - Future opportunities for expansion 22:07 - Impact of the global pandemic 25:30 - Winning the Schulich People’s Choice Award 27:08 - Using E-Commerce Platforms (Etsy & Shopify) 32:00 - Online Growth Strategy 37:30 - Exposing Shopify gurus 44:38 - Entrepreneurship & Empowerment 48:15 - The Power of Regret 50:00 - Resources for Female Entrepreneurs 54:08 - Venture Funds vs. Black Founders 1:02:56 - Lightning Round

This episode is sponsored by · Anchor: The easiest way to make a podcast. https://anchor.fm/app

Andre is a partner at Fasken, a leading international law firm where he maintains a broad corporate law practice. Andre advises venture capital firms and emerging, high-growth companies all across Canada. As Co-Chair of the Emerging Companies Group at the firm, he is a recognized leader in Ontario’s tech ecosystem and a tireless advocate for his clients.

Andre acts as the go-to external counsel for all legal matters to companies and venture capital investors around the world, regularly speaking at legal tech conferences and events.

We ask Andre everything we need to know before taking a company public. He details the importance of intellectual property, common mistakes made by investors and founders, and how to set up your company for success.

We learned so much from this episode that we’re still expecting to receive an invoice of billable hours from the firm. Good thing you can listen to this for free!

2:30 - Intro to Technology & Law 9:50 - Common mistakes made by start-ups 17:40 - Critical factors to consider before fundraising (due diligence) 20:15 - Liquidation preference (Important!) 24:00 - Equity vs. Debt Financing 26:50 - Common mistakes made by Investors 30:38 - An interesting deal handled by Andre (litigation to M&A) 36:40 - Tech Conferences 38:58 - IPO vs. Staying Private 43:50 - Advice for future tech lawyers 46:34 - Lightning Round

This episode is sponsored by · Anchor: The easiest way to make a podcast. https://anchor.fm/app

As the Vice President of Institutional Sales at Horizons ETFs, Emerson Baker is responsible for communicating the various ways ETFs are shaping the global capital markets. He has dedicated his entire career to the ETF industry, having spent four years at BMO ETFs before joining Horizons.

Emerson understands the importance of wealth management and how to utilize the capital markets for these goals. Whether that’s investing into stocks and bonds, or ETFs and mutual funds, the investing strategy differs based on each individual, however the goal is the same - create wealth through sound investment decisions. However, not everyone has the financial literacy to take on such risks.

So we talk to Emerson about the capital markets, what we need to know before beginning to invest, and the steps we should be taking to become a successful investor. He also details the various traps along the way that we may fall into if we are not careful - such as crypto and forex pyramid schemes.

We hope you enjoy this informative conversation!

3:00 - Entering a career in capital markets 5:50 - What is the difference between an ETF and a stock? 8:30 - How to pick which ETFs to invest into 10:45 - What is the future market? 15:00 - Cryptocurrency and Forex "gurus" 19:55 - Building financial literacy 28:10 - How do each generation view the stock market? 31:20 - Why are stocks rallying during a pandemic when businesses are closed? 35:38 - Millennials and investing 46:25 - How to invest your first $1,000 54:15 - Lightning Round

This episode is sponsored by · Anchor: The easiest way to make a podcast. https://anchor.fm/app

Born and raised in Windsor, Ontario, Miah-Marie started playing basketball by chance. She picked up the sport so she wouldn’t be on the sidelines watching her siblings play and it slowly became more than that. Her mother’s philosophy: “Keep playing if the doors continued to open.” And the doors kept opening.

Miah-Marie led the Windsor Lancers to four consecutive CIS National Championships, winning the CIS Final Eight Tournament MVP and CIS All-Canadian Defensive Player of the Year honours three times. She then went onto to lead the Canadian National Women’s team to gold at the 2015 Pan American Games and the 2015 FIBA Americas World Championship, which qualified the team for the Olympics at Rio de Janeiro, Brazil.

Miah-Marie now plays in the Russian Women’s Basketball Premier League while spending her off time as a mentor and coach for the youth. We talk to Miah-Marie about her professional, what it takes to be an athlete, female empowerment and the importance of diversity and equality in sports.

We hope you enjoy this insightful conversation with such a genuine individual and true Canadian star!

2:00 - Intro to Basketball 11:39 - The grind of developing your game 16:20 - FIBA Americas Women's Championship 20:34 - Pan American Games & Winning Gold 23:14 - Female empowerment 27:25 - Equality in sports 37:18 - Mental toughness and preparation 43:55 - Diversity in sports 50:50 - Lightning Round

This episode is sponsored by · Anchor: The easiest way to make a podcast. https://anchor.fm/app

Adam is the Co-Founder and Chief Revenue Officer at Luminari, a professional community for CPAs. Their flagship product is LumiQ, a mobile podcast app where you can get verifiable professional development hours for listening to engaging conversations with business leaders on their experiences and areas of expertise. After gaining experience in the industry as a marketing professional, Adam realized that the growing podcast market could solve a common issue faced by industry professionals that hold designations - professional development hours. Earning these hours each year usually meant attending conferences or workshops that not everyone is keen on. So Adam decided, instead of going to workshops for these hours, why not bring the hours to ourselves through podcast listening that brings industry expertise to our fingertips? Just like that, the idea for Luminari was born! We talk to Adam about his journey of building a reputable professional development platforms, how his corporate experience helped him scale the company, and the ins and outs of working with a start-up. We hope you enjoy this conversation!

Show sponsored by Podcorn - visit podcorn.com today!

2:00 - Transition from the corporate world to the start-up world 4:10 - Negotiating a new position at the same workplace 8:20 - How to become more marketable 14:01 - The value of your network 24:09 - The story of Luminari 32:04 - Branding and the importance of trust 36:35 - Automation in the Finance/Accounting industry 41:49 - Advice to new graduates 47:35 - How to switch careers 50:48 - The story of John 58:12 - Lightning Round

This episode is sponsored by · Anchor: The easiest way to make a podcast. https://anchor.fm/app

Rishawn is an MD & MBA candidate at Tulane University. He is also the Founder & CEO of Memoryz, a company committed to redefining family-focused dementia care. They are developing an AI-powered chat bot that serves as almost a virtual person support worker that can keep tabs on patients in the absence of family or friends. The aim is to foster greater independence and reduce isolation for those living with dementia, while improving caregiver bandwidth.

The Canadian government estimates that by 2030, seniors aged 65 and older will make up 25% of the population while almost a quarter of the population aged 15 or older already serve as caregivers. Rishawn recognized the need for additional support as a caregiver for his grandfather, a senior living with dementia. He realized that the caregiver experience can be facilitated with technology and this sparked the idea for Memoryz.

We talk to Rishawn about the AI technology behind Memoryz, the future capabilities of his company, and how he manages a medical degree and MBA while working on his venture. We also explore the capabilities of the healthcare systems in North America as it pertains to this demographic.

We hope you enjoy this insightful conversation!

This episode is sponsored by · Anchor: The easiest way to make a podcast. https://anchor.fm/app

Swish is the CEO and Co-Founder of Trufan, a UN Youth Ambassador, 3x TEDx Speaker, LinkedIn Youth Editor, consultant to Fortune 500 brands and venture capitalists, and the list goes on. A true jack of all trades, he has built a multi-hyphenate career across the board with many roles with an emphasis on social capital. Trufan serves as a social intelligence platform that helps brands activate grassroots communities made up of super fans and micro-influencers. Their mission is to convert consumers from people who just buy to advocates who buy in. We talk to Swish about how he built his personal brand from the ground up, the power of networking and how it led him to meeting his idol (and many of ours) in Gary Vee. We also lean in on his experience as a serial entrepreneur to understand how brands can leverage social audience to grow and scale. We hope you enjoy this conversation! Get ready to get motivated!

This episode is sponsored by · Anchor: The easiest way to make a podcast. https://anchor.fm/app

Tobi is the CEO of The3Skills, a company founded on the mission to develop the most marketable people in the world by equipping them with the skills they need to understand and communicate their true value. He also works as Merchant Success Manager at Shopify.

At 15 years old, Tobi came to Canada to attend an international high school and quickly realized how big of a minefield unemployment is for this demographic of graduates. Driven by the struggles of his sister and friends to land jobs, he posted a simple message on LinkedIn:

“I want to help 5 people get jobs this year."

He received 50 messages. The idea for 3Skills was born. In one year, they helped 36 people land full time roles with a combined income of over $1.7M.

Today, the company has expanded to offer various courses, group coaching, and a referral program from a vast network of partners.

We talk to Tobi about his journey to Canada, building this company, how he landed his dream job in just 12 days, and becoming the best version of yourself.

Check the first comment below for links to this episode and we hope you enjoy his truly unique story!

This episode is sponsored by · Anchor: The easiest way to make a podcast. https://anchor.fm/app

Jimmy is the founder and CEO at Propel, Inc., a Brooklyn based company dedicated to helping low income Americans improve their financial health with technology. Their Fresh EBT app helps over 3 million households manage and budget food stamp benefits by providing an integrated platform to check their balance, view transaction history, and receive local deals. The app also provides savings tips and goals in order to improve the financial literacy of their users. The company is backed by the likes of Serena Williams, Kevin Durant, and Andreessen Horowitz. Poverty is not a particularly new issue; it is estimated that approximately 38 million people live under the poverty line in the USA as of 2019. The intersection of tech and poverty aims to foster technological innovation that will allow people and nations to lift themselves out of poverty. However, many companies do not invest into helping those less fortunate due to monetary motivations and the fact that most founders are not in a position to understand the fundamental drivers of poverty. We talk to Jimmy about how innovation in tech can continue to help those in need and how his own financial hardships led him to building Propel. Jimmy also explores the capitalist system today and how it can be leveraged to support companies that are aligned with your own personal values. We hope this conversation inspires you and teaches you more about a topic that tends to get overlooked.

This episode is sponsored by · Anchor: The easiest way to make a podcast. https://anchor.fm/app

Michael is Chief Legal Officer at YUM! Brands, the conglomerate that owns and operates the KFC, Taco Bell, and Pizza Hut banners. With almost ten years of industry experience and an executive position at one of the world's most recognized CPG-brands, it can be easily assumed that he made the right career decisions. However, this is not exactly the case.

Back in 2006, Michael completed a Bachelor of Life Sciences, expecting to enter the medical industry and suddenly realized that he did not want to go through medical school. So he consulted with family and friends on what he should do and shifted to business. He entered an MBA program and graduated in 2008... just as the market crashed. Instead of getting down, he pivoted again and applied for law school and graduated from the Osgoode School of Law. Third time seemed to be the charm! Fast forward ten years and multiple stints at various positions and he now serves as the chief legal officer at KFC Global and as legal counsel for Pizza Hut International.

Michael’s story is one of true determination and will that led to him being a Swiss Army knife of sorts in education. Instead of succumbing to social norms and accepting an unfulfilling position, or allowing external factors to decide his fate, he was able to adjust, pivot, and re-learn in order to succeed. So we talked to him about how he managed all the changes in his career direction, the stress that came with all these changes, and his insights on chasing passion for success. This conversation was insightful and eye-opening and will definitely resonate with any age group!

This episode is sponsored by · Anchor: The easiest way to make a podcast. https://anchor.fm/app

Since the tech boom, the use of smartphones and other gadgets have skyrocketed while the valuations of these companies have reached record highs. Technology has created some of our most valuable inventions and, arguably the most wealthiest individuals history has ever seen. However, many of us still do not understand how these companies operate.

Shruti is a seasoned journalist who has covered a wide range of topics from political culture, lobbying, telecom and technology, to the diplomatic community. Her roles have spanned from segment production for CTV News, reporter/editor at The Hill Times, to senior reporter at MobileSyrup. Currently, she spends her time in the tech and telecom sphere as a reporter for Yahoo Finance.

We talk to Shruti about the future of journalism, being a woman in the industry, and how millennials are shifting the use and distribution of content. With her unique perspective in tech and politics, Shruti explains how these two worlds collide and its diplomatic implications as we explore the controversy around 5G and China.

This was a truly riveting conversation that had us on the edge of our seats! We hope you enjoy!

This episode is sponsored by · Anchor: The easiest way to make a podcast. https://anchor.fm/app

Brendan Herjavec is an experienced business strategy and development professional with a background that spans seed funded startups to multinational corporations. Brendan has been a part of some of Canada’s fastest growing companies with a deep love for entrepreneurship. He had the opportunity to take his creativity around the globe ranging from working in a traditional Japanese Bonsai Nursery, to helping create business plans in England through the EY Young Entrepreneurship program, to assessing blockchain viability in Hong Kong for GeoSwift.

He is currently involved in the intersection of the tech and mental health space, all while completing his MBA at UBC. Brendan is a Client Manager for Inkblot Therapy, a company that helps match mental health practitioners to clients through multiple channels. He also serves as an Advisor for Memoryz, an AI based company that developed a chatbot to help dementia patients and their caregivers stay organized, connected and engaged.

We talk to Brandon about his experience growing up in an entrepreneurial family, the cross-cultural lessons he has learned from around the world, and what steps we can take to hack growth in B2B and B2C companies to help with scaling up. We hope you enjoy this conversation!

This episode is sponsored by · Anchor: The easiest way to make a podcast. https://anchor.fm/app

Brendan Rogers is the co-founder of Wag, the mobile dog walking app that disrupted the global pet service space, matching dog-walkers and dog-parents with a simple swipe. Wag raised over $360 million in venture capital, most recently $300 million from Softbank's Vision Fund.

He is currently the founder and managing partner of 2AM Talent and Ventures - a pre-seed, industry agnostic, micro fund investing in ambitious founders. Brendan is an active advisor and mentors many companies, accelerators and universities in Los Angeles, Silicon Valley and South Korea. Being a true people person, Brendan looks beyond the formalities and focusses on the individuals that he is investing into.

We talk to Brendan about his entrepreneurial journey and how he successfully scaled his businesses, his experience as a mentor and angel investor, and what makes individuals great leaders. He also expands on the importance of personal branding as it pertains to the digital era that we are in today. We hope you enjoy this truly insightful conversation!

This episode is sponsored by · Anchor: The easiest way to make a podcast. https://anchor.fm/app

Anthony Zhang is a serial entrepreneur, fellow at the prestigious Thiel foundation, and an active angel investor. He built his first business as a freshman at USC which he successfully pitched to the likes of Mark Cuban.

This episode is sponsored by · Anchor: The easiest way to make a podcast. https://anchor.fm/app