Why I Quit: Recent Episodes
Dave Phelan - Founders Approach
Real stories of real people quitting their 9-5s in search of something different. Listen to inspiring conversations where we dive deep into the stories of why people quit their jobs, what were the hardest parts, where they are now, and any advice for people considering the same path.
We are so excited to introduce Elena Agaragimova as this week’s guest on “Why I Quit.” Listen as Elena discusses her journey of quitting her corporate job, starting a business, and then eventually going back into the corporate world. Learn how she developed the self awareness to understand what type of work she is most interested in and passionate about. Get inspired hearing about how she has continued to build her personal brand through podcasting and freelancing while still working a full-time job.
Learn More About Elena:
LinkedIn - https://www.linkedin.com/in/elenaagaragimova/
Website - https://elenaagar.com/
Podcast - https://www.bessern.co/shift-podcast
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We are so excited to introduce Lia James as this week’s guest on “Why I Quit.” Listen to Lia share her journey of quitting corporate jobs multiple times to start different companies over the years. Learn how she drove around the country in a van with a dinner table to bring together strangers and engage in meaningful conversation. Get inspired hearing about how she is currently turning her home into a space for people to gather, reset, and connect in more meaningful ways.
Learn More About Lia:
LinkedIn - https://www.linkedin.com/in/liajames/
Website - https://www.andhuman.space/
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We are so excited to introduce Gino Cordone as this week’s guest on “Why I Quit.” Listen as Gino discusses his journey of leaving his corporate career in mechanical engineering. Learn how he went from a side hustle to starting his full time business called Pleasant Podcasts. Get inspired how he has continued to learn and pivot to grow and scale his business by helping others create their own podcasts.
Learn More About Gino:
LinkedIn - https://www.linkedin.com/in/gino-cordone-4171ab60/
Website - https://pleasantpodcasts.com/
Podcasts - https://pleasantpodcasts.com/my-podcasts
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We are so excited to introduce Kay Ready as this week’s guest on “Why I Quit.” Listen as Kay discusses her journey of dropping out of high school and becoming a teen mom. Learn how she used this experience to propel herself into the sales industry where she has now had over 25 years of experience. Get inspired hearing how she has been able to create multiple six-figure income streams from home and educate others to do the same.
Learn More About Kay:
LinkedIn - https://www.linkedin.com/in/kayreadyrealtor/
Website - https://www.kayreadyempowers.com/
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We are so excited to introduce Barb Otis as this week’s guest on “Why I Quit.” Listen as Barb discusses her career in organizational development to help make the workplace a better place for employees. Learn how she discusses her personal experiences learning why her coworkers quit and going through the process of quitting herself. Get inspired hearing about how she wrote a book to help both employees and managers called “101 Ways to Lose A Great Employee.”
Learn More About Chris:
LinkedIn - https://www.linkedin.com/in/barb-o-a703775/
Book Website - https://iquit.net/
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We are so excited to introduce Chris Zaccaria as this week’s guest on “Why I Quit.” Listen as Chris discussing his journey of working in 8 different jobs over the course of a decade to figure out his career goals. Learn how being laid off gave him the opportunity to start his own recruiting firm. Get inspired hearing how he has gained control over his schedule and finances as he has scaled his company, CZ Consulting, over the years.
Learn More About Chris:
LinkedIn - https://www.linkedin.com/in/chris-zaccaria/
Website - https://www.czrecruit.com/
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We are so excited to introduce Paul Baron as this week’s guest on “Why I Quit.” Listen as Paul discusses his journey of quitting his job as a math teacher to start a business in the tennis industry. Learn how he started and owned a series of high-technology software, communications hardware, and consumer packaged goods companies. Get inspired hearing how at age 70, he is scaling he latest business venture which provides vertical printing solutions called The Wall Printer.
Learn More About Paul:
LinkedIn - https://www.linkedin.com/in/pbbaron/
Website - https://thewallprinter.com/en/
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We are so excited to introduce Ryan Beach as this week’s guest on “Why I Quit.” Listen as Ryan discusses his journey of hitting his career goals very early on. Learn how he decided to take a leave of absence and travel around South America for 3 months. Get inspired hearing how this gave him the time and space to figure out what he wanted and led to a promotion and new role at his company.
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We are so excited to introduce Ellen Matis as this week’s guest on “Why I Quit.” Listen to Ellen discuss her story of deciding on New Year’s eve that she would quit her full-time job and how she handed in her notice two weeks later. Learn how she started a social media marketing agency called Hello Social Co. Get inspired hearing how she has hired full time employees, implemented a 4 day work week, and scaled the business over the past 5 years.
Learn More About Ellen:
LinkedIn - https://www.linkedin.com/in/ellenmatis/
Website - https://hellosocialco.com/
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We are so excited to introduce Matt Howitt as this week’s guest on “Why I Quit.” Listen as Matt discusses his journey of layoffs, freelancing, quitting, and eventually starting his own business.
Learn how he and business partner Alex Wasner started a software development agency called twothirtysix labs where they help brands launch websites, digital collectibles and other web3 projects. Get inspired how they quit their full-time jobs to go all in and have scaled the business to (9) full-time employees.
Learn More About Alex:
LinkedIn - https://www.linkedin.com/in/matt-howitt-456559b4/
Website - https://www.twothirtysix.com/
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We are so excited to introduce Alex Politsch as this week’s guest on “Why I Quit.” Listen as Alex discusses his journey of quitting his job as a financial advisor to buy a food truck. Learn how while attending Oktoberfest in Germany, he and his best friend, Steven Banks, came up with the idea of starting a doner kebab food truck called Döner Brös. Get inspired how they scaled the business, survived, COVID, and now have two brick and mortar locations in Baltimore.
Learn More About Alex:
LinkedIn - https://www.linkedin.com/in/thejasonbrowne/
Website - https://thejasonbrowne.com/
AW Rebels - https://www.facebook.com/gaming/awrebels
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We are so excited to introduce Jason Browne as this week’s guest on “Why I Quit.” Listen to Jason share his amazing journey from quitting his full-time job at Penn State University to test and validate different business ideas. Learn how he thinks about the type of ventures he wants to do based on a personal SWOT analysis he conducts for himself every 3-6 months. Get inspired hearing about his successes as a Public speaker, award-winning radio host, Facebook Gaming partner, consultant & Rotarian.
Learn More About James:
LinkedIn - https://www.linkedin.com/in/thejasonbrowne/
Website - https://thejasonbrowne.com/
AW Rebels - https://www.facebook.com/gaming/awrebels
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We are so excited to introduce James Tierney as this week’s guest on “Why I Quit.” Listen as James discusses his story of turning his passion for education into starting his own tutoring business right out of grad school. Learn how his love of improv during college turned that into launching his own group called Happy Valley Improv. Get inspired hearing how James practices what he preaches to his entrepreneurship students. This enabled him to quit his full-time job as a professor to scale his multiple businesses.
Learn More About James:
LinkedIn - https://www.linkedin.com/in/jamesetierney/
Happy Valley Improv Website - https://www.happyvalleyimprov.com/
Blue Brick Theater Website - https://www.bluebricktheatre.com/
Private Tutoring and Coaching Website - https://www.tierneyeducation.com/
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We are so excited to introduce Robert Bentley as this week’s guest on “Why I Quit.” Listen as Robert discusses his journey from starting a mobile development business in the early days of iOS 4. Learn how he waited tables to pay the bills while trying to build the business. Get inspired hearing how he has scaled the Jed Mahonis Group over the past 10 years helping founders and businesses bring their ideas to life.
Learn More About Robert:
LinkedIn - https://www.linkedin.com/in/robert-bentley-47804b29/
Company Website - https://jedmahonisgroup.com/
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We are so excited to introduce Matt Wolff as this week’s guest on “Why I Quit.” Listen to Matt discuss how he came up with his business idea while attending a no hitter at a MLB game. Learn how he started building this business in addition to working a full-time job for 2 years. Get inspired hearing how he quit his job and has a grown Ticket Time Machine to work with some of the larger brands in sports.
Learn More About Matt:
LinkedIn - https://www.linkedin.com/in/mattwolff3/
Company Website - https://tickettimemachine.com/
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We are so excited to introduce Joanna Pease as this week’s guest on “Why I Quit.” Listen as she discusses how the 2008 housing crisis changed the trajectory of her career plans. Learn how she became passionate about indoor cycling while traveling across the country in her sales role. Get inspired how she took that passion and quit her job to start a rhythm based indoor cycling studio called Jibe. Check out one of their three locations in Charleston (SC) or Portland and Yarmouth (Maine).
Learn More About Joanna:
LinkedIn - https://www.linkedin.com/in/joanna-pease-a360106/
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We are so excited to introduce Eric Sauter as this week’s guest on “Why I Quit.” Listen as Eric discusses his story of quitting his job to become the first employee at a startup called Fixt. Learn how he discusses the process of getting acquired and transitioning back into working in a corporate environment with the company that acquired them. Get inspired how he quit again to take a step back and figure out what his next steps are.
Learn More About Eric:
LinkedIn - https://www.linkedin.com/in/emsauter/
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We are so excited to introduce John Balkam as this week’s guest on “Why I Quit.” Listen as John discusses his journey of quitting his job multiple times to start different businesses.
Learn how the process of writing a book inspired him to quit his job to start an agency that combined sports, entertainment, and cause marketing called the Third Win Group. Get inspired listening to how he tied the growth of his business to the growth of his impact on the world.
Learn More About Phil:
LinkedIn - https://www.linkedin.com/in/johnbalkam/
Website - https://thirdwin.com/
Book - https://thirdwin.com/book/
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We are so excited to introduce Phil DiMuro as this week’s guest on “Why I Quit.” Learn as Phil discusses his journey of quitting his full-time job to launch a mobile app. Listen how he describes the reality and sacrifices of becoming an entrepreneur. Get inspired hearing how he used his previous experiences and failures to launch a software development agency called Founders Approach, where he helps startups and small businesses launch their own mobile apps or websites.
Full disclosure, Phil and I have been best friends since college and business partners for over 7 years. However, I still learned new things during this interview. This is part of the reason we love sharing and telling new stories on “Why I Quit.”
Learn More About Phil:
LinkedIn - https://www.linkedin.com/in/philip-dimuro-5246b230/
Website - https://foundersapproach.com/
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We are so excited to introduce Chris Rickard as this week’s guest on Why I Quit. Listen as Chris discusses his journey of going from a full-time developer to scaling his own software development agency. Learn how he sold his business and has been traveling around Australia in a RV for the last 10 months. Get inspired hearing how he now focuses on helping other developers start their own agencies.
Learn More About Chris:
LinkedIn - https://www.linkedin.com/in/chrickard/
Website - https://devtoagency.com/
Twitter - https://mobile.twitter.com/chrisrickard
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I am so excited to introduce Jae Jin as this week’s guest on “Why I Quit.” I first saw Jae Jin perform at Sofar Sounds in Baltimore and was absolutely blown away. As a person, musician, and storyteller, he is one of the most inspiring people I have met. Not going to lie, this was one of my favorite episodes and I hope you all check it out!
Listen as Jae tells his story of how being a two time cancer survivor led him down the path of quitting his job and turning down med school. Learn how he sold all his possessions, packed two suitcases, and bought a one way bus ticket to NYC to pursue music full-time. Get inspired hearing how he refused to sign with a label, but has built a successful career on his own as a singer, song writer, actor, and public speaker.
Learn More About Jae:
LinkedIn - https://www.linkedin.com/in/jaejin/
Website - http://www.jaejinmusic.com/
Music - https://jaejinmusic.bandcamp.com/
Concert Dates - http://www.jaejinmusic.com/tour
Patreon - https://www.patreon.com/jaejinmusic
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We are so excited to introduce Austin Benoit as this week’s guest on “Why I Quit.” Listen as Austin discusses his journey of taking an SEO course and quitting his full-time mechanical engineering job one year later to start Search Prestige. Learn how experimenting with dropshipping, MBA classes, and freelancing led him down the path to where he is today. Get inspired hearing Austin think about building a business that optimizes his time and happiness.
Learn More About Austin:
LinkedIn - https://www.linkedin.com/in/austin-benoit-solutions/
Company Site - https://www.searchprestige.com/
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I am so excited to introduce Brian Gaudio as this week’s guest on “Why I Quit.”
Listen as Brian discusses how he fell in love with architecture from a young age but never wanted to work for a corporate firm. Learn as he discusses how filming a documentary in South America and completing a Fulbright Fellowship in Dominican Republic inspired him to start his own company called Module based in Pittsburgh, PA. Get inspired hearing about his mission to tackle big issues by using design to create new jobs and more affordable housing in cities across the country.
Learn More About Brian:
LinkedIn - https://www.linkedin.com/in/briangaudio
Module - https://www.modulehousing.com/
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I am so excited to introduce Lucas James as this week’s guest on “Why I Quit.” Listen as he discusses never having a corporate job and starting a digital marketing agency while still in college. Learn how he shifted his priorities from filmmaking to business so he could make a bigger impact on the world. Get inspired hearing how he has scaled his business in addition to starting another venture where he helps other agency owners scale their businesses together.
Learn More About Lucas:
LinkedIn - https://www.linkedin.com/in/lucascapestany/
Twiz (Digital Marketing Agency) - https://twiz.io/
AgencyGo (Community of Agency Owners) - https://agencygo.io/members53119953
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I am so excited to introduce Cody Benedetto as this week’s guest on “Why I Quit.” Listen as Cody discusses his experiences working with big tech corporations during the beginning of his career. Learn how he started investing in real estate and building a startup on the side while working a full-time job. Get inspired listening to how he quit his job two months ago to start his own software development agency called Modern Launch to focus more on controlling his schedule and spending more time with his family.
Learn More About Cody:
LinkedIn - https://www.linkedin.com/in/cody-benedetto/
Modern Launch (Software Development Agency) - https://modernlaunch.co/
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I am so excited to introduce Amanda Mottola as this week’s guest on “Why I Quit.” Listen to Amanda discuss her adoption and the impact of finding her birth family in Paraguay. Learn how this led to her quitting her job, getting into politics, and eventually starting her own business. Get inspired listening to her speak about finding her passion and leaving a legacy for her children.
Learn More About Amanda:
LinkedIn - https://www.linkedin.com/in/amanda-mottola-0543441b/
Marketing Agency - https://www.otraway.com/
Author of “Learning as a Lifelong Journey” - https://amandamottola.square.site/
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I am so excited to introduce Rob Kyne as this week’s guest on “Why I Quit.” Listen as he discusses his decision to take a sabbatical and drive across the west coast with his family in an RV. Learn how this helped Rob decide to walk away from his business he had been running for 20 years. Get inspired hearing how Rob has been able to spend more time with family, live in the moment, and find new ventures he is passionate about.
Learn More About Rob:
https://www.linkedin.com/in/rob-kyne-6a46228/
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I am so excited to introduce Lisa Keitges as this week’s guest on “Why I Quit.” Listen as she discusses how starting her own business allowed her to work with non-profit organizations that align with her values. Learn how she decided to go fully remote by moving from an apartment in New York City to a farmhouse in the Catskill mountains during COVID. Get inspired hearing how quitting her job allowed her to re-evaluate her relationship between work and life.
Learn More About Lisa:
https://www.linkedin.com/in/lisakeitges/
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I am so excited to introduce Steve Krakower as this week’s guest on “Why I Quit.” Listen as Steve discusses how he took everything he learned from his first full-time job to quit and start his own digital marketing agency. Learn about his struggles during the first year and how not having a plan b forced him to push him through the tough times. Get inspired hearing about how Steve scaled Harbor Marketing Agency by finding the right employees and narrowing the focus of their services over the past 5 years.
Learn More About Steve:
https://www.linkedin.com/in/steve-krakower/
https://www.harbormarketingagency.com/
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I am so excited to introduce Brian Chupek as this week’s guest on “Why I Quit.” Listen as he discusses quitting his full-time job at Morgan Stanley with no plan as to what was next. Learn how Brian chose starting a real estate business to have more control over his schedule and prioritize the relationships in his life. Get inspired by listening to how he is diversifying his revenue streams by continually exploring new business opportunities.
Learn More About Brian:
brianchupek@kw.com
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I am so excited to introduce Gerson Martinez as this week’s guest on “Why I Quit.” Listen to Gerson discuss his experiences of being raised in rural Maryland by his parents who emigrated from El Salvador. Learn how he achieved his lifelong dreams of getting a job on Wall Street, but why he quit to find his purpose. Get inspired hearing about his journey to help create a more financially inclusive and equitable society.
Learn More About Brian:
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I am so excited to introduce Cole Barger as this week’s guest on "Why I Quit." Full disclosure Cole is a member of the Founders Approach team with Phil and I, but I couldn’t think of a better guest to share their story. Listen to Cole discuss rising the corporate ladder at Stanley Black and Decker. Learn how he quit his full-time job to focus more on his personal relationships and start a business where he felt he could make a more direct impact. Get inspired listening to how he pivoted from two startups ventures in the motorcycle space to now helping founders bring their own ideas to life.
Learn More About Cole:
Website
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Guest Intro:
I am so excited to introduce Brian Taylor as this week’s guest on “Why I Quit.” Listen as he discusses how he never had a 9-5 and he dove straight into starting his own digital marketing agency, Goldiata Creative. Learn as he speaks about how he taught himself about different service offerings that he could sell to potential clients and how he was learning on the fly of how to run a business. Get inspired hearing how he has been able to scale his agency to 4 employees, exceed his own expectations, and begin to focus on his personal goals as well.
Learn More About Brian:
Website If you enjoyed this episode, please either:
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Today, we are joined by Joanna Winkler, who first got interested in farming when working for The Food Project in high school. They brought kids together from Boston to work on an urban farm and to build a more sustainable food system. While she fell in love with farming, she did not believe it could be a viable career opportunity.
While Joanna was studying government policy in college, she worked at Red Fire Farm in Western Massachusetts during the summer. She got her first experience with a CSA, which is community supported agriculture (a group of people purchase share’s of a farm’s harvest). After graduation, she moved to Baltimore, Maryland as part of the AmeriCorps VISTA program. She got her first office experience working with the Baltimore Food Policy Initiative.
Even though Joanna loved the work she was doing, she felt trapped working full-time in an office. She moved on to her next full-time role, but she was going out into the field hosting educational events at farms. This gave her the experience to see the inner working of smaller farms. For the first time, she started thinking that she could run her own farm.
Joanna started getting heavily involved in the urban farming movement in Baltimore. She worked at Cherry Hill Urban Garden, volunteered at the Farm Alliance of Baltimore, and completed a farmer training program (where you work one day a week at farm). Around this same, Joanna met her now husband, Brian Alexander. He was also heavily involved in the farming community and had similar goals to her.
Joanna, Brian, and one their friends start planning what it would look like to run their own farm and started looking at properties at the end of 2015. They found the spot in the county a half an hour north of Baltimore and moved into the property. They spent 18 months still working full-time jobs in addition to starting Good Dog Farm. Eventually they were able to feel comfortable enough with the proceeds from the farm to make the leap to quit their jobs and run the farm full-time.
Fast forward to today, Joanna and Brian now own 25 acres of land and are growing their operation. They have staff and grow crops all year round. The offer a modern take on a CSA, where every and every other week, people can mix and match what fruits and vegetables are available based on the season. They started in Baltimore and this year and expanding to Washington D.C. for the first time this coming year.
Full disclosure, I am a customer of their CSA and could not recommend it enough for anyone in the Baltimore or DC area. If interested, look into signing up here!
Check out the conversation as we dive into the following:
- How working on a farm in high school planted a seed that eventually led to her running her own farm
- Why she felt trapped in an office job
- How she was able to work a full-time job in addition to starting and running a farm
- Why it was so important to “quit gradually”
- What the day in the life of a farmer looks like
Listen to Joanna share her story and get inspired with her amazing advice to people thinking about following a similar path.
Today, we are joined by Lauren Elsasser Smith, who started her entrepreneurial journey by starting a food truck business while taking classes in college. After graduating, she landed her first full-time role with Birchbox and managed to keep running her food truck business on nights weekends, and vacation days.
Lauren ended up quitting Birchbox to focus full-time on her business. Around the same time, her husband, Jared, was starting his residency in Lynchburg, Virginia. So Lauren moved, sold the business, and invested the proceeds and starting her next venture in wedding photography. She was able to scale that business and eventually got recruited by Burger King Corporate to take another full-time role. She worked her way up the ranks to become the marketing manager of Burger King Northeast US.
Lauren began traveling for work and was struggling to find work life balance. She became pregnant, which shifted her priorities. She and her husband sat down to put together a detailed 6 month plan on how long they could survive without her salary. Lauren eventually worked up the courage to tell her boss she was quitting without a plan of what was next.
They cut down on their expenses and gave Lauren the space to figure out what was next. Around 6 months later, Lauren was offered the opportunity to follow her passion of teaching and is currently the Visiting Assistant Professor of Management and Marketing at her alma mater, Susquehanna University. While Lauren’s resume speaks for itself, you can tell when speaking with her how her family, relationships, and work-life balance matter above all else.
Fast forward to today and Lauren has found an incredible balance of spending time with her family and having a career she is passionate about. As most of you would guess, she is already onto the next idea of rehabbing an A-frame cabin to eventually turn into a micro wedding/Airbnb venture.
Check out the conversation as we dive into the following:
- How she was able to run side businesses in addition to a full-time job
- Why it was so hard to leave your coworkers when quitting
- How she mapped out a 6 month plan to be able to quit
- How she prioritized her family and relationships over her career
- How the extra time and space from quitting led to her buying an A-frame Cabin to start an Airbnb and wedding venue
Listen to Lauren share her story and get inspired with her amazing advice to people thinking about following a similar path.
Today, we are joined by Nic China, who comes from a family of entrepreneurs. His grandfather immigrated from Italy and started a company in Baltimore, which was passed down to Nic’s father. Nic always knew from a young age that he wanted to start his own business, but he wanted it to a different path from the family business.
After graduating from Wake Forest University with an art degree, Nic went on one interview where he quickly realized it was not for him. He went to work for the family business, which allowed him to learn the ropes of running a business. At the same time, he was constantly trying different side hustles on nights and weekends.
While at a best friend’s wedding in Chicago, Nic had hist first experience with an open air photo booth. He had never seen anything like it and was spit balling ideas with friends about starting their own. He gets introduced to his now business partner, Patrick Rife. Next thing you know, they are building a prototype with a DSLR camera inside a box with a stand and monitor. They take it to a bar for a friend’s birthday party and the demand is off the charts. They create a time lapse video after the event and it gets shared all over social media. At this moment, they knew they were onto something and began double down building the Pixilated.
At this point, Nic is still working a full-time job and running the photo booth company on nights and weekends. They hit $40k in sales in year one and increased to $250k in year 2. Nic and Patrick are now ready to quit their full-time jobs and going all in on Pixilated.
Nic wanted to build Pixilated to reflect his personality. He wanted to build a culture that focused on consistency and hard work, but with a laid back atmosphere built on trust. Pixilated saw huge growth year after year as they continued to iterate on their product to focus on producing the highest quality of images for events.
Fast forward to COVID and everything changed. Their events business stopped overnight. They had to cut staff and had no idea what they were going to do. They were able to pivot to built a web offering to have online photo booths for virtual events by launching PixiWeb. Even when events came back, they now had offerings to service hybrid in-person and virtual events. Today, they continue to evolve to Pixilated 3.0, which shifted their business to e-commerce. They ship out photo booths to events was easy to use instructions. They no longer need events staff and have expanded their company footprint to across the United States.
Last month, Nic and Patrick celebrated their 10 year anniversary with Pixilated. They have consistently focused on building a company they want to work for and pivoted to adapt to whatever situation is thrown at them.
Check out the conversation as we dive into the following:
- How working for the family business when he was a teenager led to his entrepreneurial dreams
- How he was forcing to different ideas to start a business, but a photo booth company fell into his lap at a wedding
- How he worked nights and weekends for 2 years before feeling stable enough to quit his full-time job
- How finding and retaining customers is the hardest part of any business
- How he and his co-founder were forced to pivot several times to stay in business
Listen to Nic share his story and get inspired with his amazing advice to people thinking about following a similar path.
Today, we are joined by Scott Skrivan, who followed an incredible journey from the Navy to full-time systems engineer at Lockheed Martin to quitting in order to become a tattoo artist.
As he was in his final year at school, Scott was trying to figure out next steps. He ended up enlisting in the Navy for a 4 year tour. He followed a path into the intelligence sector as a cryptologic technician that focused on collections.
Towards the end of his tour, Scott was ready for a change. He was struggling with his work schedule where sometimes he was working nights and others he was working weekends. He felt the role was affecting his quality of life, his personal health, and his relationships. As his enlistment ended, he had the opportunity to interview for the same exact role with Lockheed Martin, but he would only need to work 9-5 style Monday through Friday. Also, he was able to start traveling for work and ended up heading to places like Japan and Thailand.
During these travels, Scott became fascinated by the meaning and history behind tattoos. He started getting more tattoos on each trip. The more he spoke with tattoo artists, the more he learned about the industry as a whole. Throughout Scott’s life, he had always found peace in drawing. He would spend hours on end with pencil and paper. Eventually this translated into Scott designing his own tattoos. Then he started putting together his own drawing portfolio to hopefully receive a tattoo apprenticeship.
When the opportunity arose, he would work his full-time job from 6am-2pm and would head to the tattoo shop from 3-7pm. He was learning as much as he could. He even completed his first tattoo on himself as training. He started recruiting buddies by offering free tattoos to help him practice.
Scott had serious discussions with his wife about what this meant and how feasible this was for their lifestyle. They sat down with their financial planner to come up with a plan. They set benchmarks to make sure they could achieve their short term, medium term, and long term goals. He spent 8 months until he got to the point he would enough clients to make the leap to becoming a full-time tattoo artist.
If you are interested in getting a tattoo or want to see his amazing work, check out his Instagram. Stop by and visit him at Spell Craft Tattoos in Baltimore!
Check out the conversation as we dive into the following:
- How drawing was always his safe space throughout his life
- How he learned the ins and outs of the tattoo industry by talking to the artists while getting his own tattoos
- How quality of life became a higher priority when considering next career opportunities
- How he learned to tattoo by first tattooing himself
- How he came up with a feasible plan to make sure tattooing was a long term viable career
Listen to Scott share his story and get inspired with his amazing advice to people thinking about following a similar path. Check out the full conversation on YouTube or Spotify by clicking the links below.
Today, we are joined by Connor Lewis, who quickly realized during an internship that his career path to be an accountant was not for him. He fell in love with film making while producing content on social issues with Northeastern University Television. He was able to secure his first job with this skill set getting hired by the Predictive Index to make marketing videos. He proved the value of content to his company and was able to work his way up to lead the department.
During COVID, his role changed. They were no longer going into the office and he spent his days working from home and editing zoom videos. He no longer felt passionate about his work and was looking for a change. He began considering different options of quitting, going into social work, or going back to grad school. Connor worked up the courage to speak honestly with his manager about how he was feeling and his manager listened. They offered him the opportunity to shift his role into making documentaries. He started with a 3 minute documentary on “being understood at work” and hit the ground running from there.
Fast forward to present day and Connor became fascinated hearing about more and more colleagues trying quitting their jobs. He began reading articles about the data behind more people transitioning jobs than ever before. He pitched his company on getting on the forefront of this issue. Over the course of a month, Connor traveled to 10 different states and interviewed industry experts, people changing careers, and companies changing their company culture in the current environment.
These conversations led to the documentary “Work on Trial” where Connor focuses on rethinking not only where, but also why and how people work. With the relationship changing between work and life, it becomes increasingly difficult to separate the two. Connor is on a mission to give people a language to talk about what they want from work. It truly is an amazing documentary and everything should check it out here!
Check out the conversation as we dive into the following:
- How his search for purpose in the workplace led him to film making
- How his friends and colleagues quitting their jobs inspired him to make a documentary
- How jobs are like a relationship with a friend, it is not going to work if it is not beneficial for both sides
- How during his interviews the concept of “being listened to” was the number one factor that would lead to a person staying at their job
- Why it is up to both the individual and the corporation to build community in the workplace
Listen to Connor share his story and get inspired with his amazing advice to people thinking about following a similar path.
Today, we are joined by Ian Sharman, who has literally ran around the world. He started his career as an economist for Deloitte in London. While living in the city, Ian was getting tired of the nightlife scene and looking for a healthier lifestyle. After seeing a commercial for a marathon in the Sahara desert, he started training. Soon after, he completed his first half marathon and never stopped running.
Fast forward a few years and Ian became the youngest person to complete 100 marathons. Most weekends he would travel to new cities around the world, complete a marathon, and head back to work on Monday morning. He combined his love of travel and desire to keep getting better at running.
Around this time, Ian moved to the United States while still working for Deloitte. He switched roles and was not enjoying his new position. He had just won a big race and received his first sponsorship. He decided now was the time to quit his full-time job to build a career in the Ultra Marathon industry. He focused on building a business that allowed him to run and travel around the world, while having a stable long term viable career.
Ian was able to develop multiple revenue streams, such as sponsorship, coaching, podcasting and race directing. He built a team of world class runners underneath him and has a full fledged coaching business to help train clients to achieve their goals in the Ultra Marathon space. If you are looking for a coach or looking to get into Ultra Marathoning, feel free to reach out to Ian here.
It’s hard to keep up with all of Ian’s accolades, but here is a snapshot of what he has accomplished so far. He has run over 200 ultras and marathons (PR: 2:21) in every type of weather and on all terrains. He's won over 50 multi-day races/road marathons/trail ultras or adventure races with experience of running in many mountain ranges, including the Himalayas, Andes, Rockies and European Alps. He also holds the fastest time in a trail 100-mile race by a Brit (12h44m), the record for the Grand Slam of Ultrarunning (69h49m), has won the USATF 100-mile trail championship twice and is a four-time Leadville Trail 100 Champion. Ultra Running Magazine has voted him as high as 2nd in its annual Ultra Runner of the Year rankings and 4th in Ultra Runner of the Decade.
Check out the conversation as we dive into the following:
- How he taught himself how to train for ultra marathons using trial and error
- How he is most proud of setting the record for the “Grand Slam of Ultra Running” which is four 100 miles races in one summer
- How he set his business up to be able to run and travel
- How he focused on making sure his business was a long term viable option even after his running prime is over
- Why artificial intelligence is not as good as human experience when it comes to coach
Today, we are joined by Kathleen Porter Kristiansen, who has a unique story that has taken her all across the world. She is an 8th generation “Mainer,” who grew up in Portland. While loving her hometown, Kathleen was always itching to travel aboard. When looking into law school, she found an education hack with the opportunity to go to law school for free in London. This allowed her to avoid over $200k of debt while gaining experience in the international law field.
Kathleen spent three years working for a law firm in London before switching to a new role that was stationed in Switzerland. While living full-time in a Marriott in Zurich, she got her first taste of travel points hacking. Even though she enjoyed her position, she was working over 100 hour weeks and knew that this life style was not sustainable.
Kathleen found a new role back in the UK in the field of legal technology, which she was extremely excited about. Over the next few years, she had two children and was able to take two years off for maternity leave. During this time, Kathleen kept thinking about what was next and started dabbling in different ventures. She purchased an apartment in Portland Maine to manage as an Airbnb and have a place to stay when visiting her hometown. With the first one being a success, she continued to purchase new properties to grow her Airbnb business.
Around the time, The Points Guy was looking to start a UK branch for his business. Kathleen sent multiple cold messages to the founder and was able to lock in a meeting as he was visiting the UK. This led to Kathleen being offered the opportunity to write content and she took the leap to quit her full-time job.
Fast forward, Kathleen manage three Airbnbs and has created an online brand called “Triple Passport” that focuses on travel, investing, and family content. She has been featured in several media outlets, such as CNN, CondeNaste, Vogue, etc. Also, Kathleen is a regular contributor to The Points Guy and The Points Guy UK.
If you are interested in learning more from Kathleen, feel free to follow her here.
Check out the conversation as we dive into the following:
- How she used education hacking to go to law school for free
- How she built an Airbnb business while still working a full-time job
- How social media opened the opportunity to cold connect with others and how this changed her life
- How content creation can be a roller coaster
- How she utilizes time blocking to manage time between her businesses and her family
Listen to Kathleen share her story and get inspired with her amazing advice to people thinking about following a similar path.
Today, we are joined by John Brickman, who moved to New York City when he was 18. While studying political science at college, the plan was always to go to law school. At this same time, John started dabbling in entrepreneurship. He began leasing apartments throughout the city and renting them for 30 days on Airbnb. He was able to grow this business as he kept adding properties.
Around this same time, John met his business partner Steve, who had an idea about a new potential industry. He wanted to train and use k-9s to detect bed bugs inside buildings. With graduation around the corner, John had a decision to make. Should he go to law school, take on debt, and spend his career in the legal space or should he start a new business based on an idea in an unproven industry?
John and Steve took the leap and started NYC Bed Bug Inspections in 2014. Both had different skillsets to bring to the table. John focused on building the website, growing the SEO, and driving traffic to the business. They purchased two k-9s that were trained to detect bed bugs within an 8 foot radius. While there were other bed bug companies, they were the only ones that used k-9s and only offered inspection specific services. They did not have the conflict of interest of also offering the extermination services. This allowed them to give their clients peace of mind and their k-9s allowed them to be more accurate than other services out there.
They have continually improved their digital presence to increase the number of leads. They have built up a strong client base of businesses that need their services ranging from hospitals to airports to apartment buildings. They also learned the methods to train and certify their own dogs. Over the past 7 years, John and Steve scaled the business and became a leader in this industry throughout New York City.
This success has inspired John to help other entrepreneurs start their own businesses. He took this and has started a new digital marketing agency where he helps businesses grow their web presence similar to how he did with NYC Bed Bug Inspections.
If you are interested in learning more from John, feel free to reach out to him here.
Check out the conversation as we dive into the following:
- How he came to the decision of whether to go to law school or start a new business
- How he started multiple businesses in industries he had no experience in
- How anyone can learn to build a website and grow SEO by watching Youtube
- Why you should have buffer and you should keep your 9-5 while getting started
- How the first year in business is the hardest
Listen to John share his story and get inspired with his amazing advice to people thinking about following a similar path.
Know someone who should be on Why I Quit? We’re looking for all types of stories and people to feature at the top of the show. To nominate yourself or someone else, email dave@foundersapproach.com and tell us your name, where you’re from and what you want to talk about.
Today, we are joined by Maria Traino, who has quit three different jobs in search of a career she was passionate about. She has always loved being creative and working in graphic design. This led her to securing different roles at a marketing agency, newspaper, and a non-profit. Growing up as the daughter of third-generation Italian restaurant owners, Maria was always inspired to have side hustles even while working full-time. She spent over a decade building up freelance clients part-time and eventually started to consider leaving her full-time job to build her own business.
She put together a plan thinking through what she would need to cover her expenses to make the leap. Three months later, she officially started Inspired Studios, which is a boutique brand design, and strategic marketing agency. She thought about what she could do if she gave her full time and attention to the business and set a goal of matching her corporate salary over the course of the first year. Not only did she achieve this goal she has continually grown her business over the past nine years. She focused on building relationships, increasing value, and partnering with experts to offer more services to help their clients grow their businesses.
During COVID, Maria felt a pull towards another mission. She became inspired to help other entrepreneurs as they work to design their business and life. She offers one on one coaching and you can find more information about it here!
Check out the conversation as we dive into the following:
- How being the daughter of third-generation Italian restaurant owners helped shaped her ideas about building a services business
- How she experimented to figure out what type of work she didn’t like to do
- How important it is to embrace being uncomfortable in business
- How work life balance is about integration and accepting that work is part of your life
- How she didn’t want to have to chose between being a parent versus a business owner. So she made it her mission to be great at both
Listen to Maria share her story and get inspired with her amazing advice to people thinking about following a similar path.
Today, we are joined by Pete Jones, who quit multiple jobs, started a blog, backpacked through Central and South America for 4 months, worked remote while driving an RV across the country, and has started 5 different businesses with his wife, Jordan. It is almost impossible to keep up with all of Pete’s ventures, but it is hard not not to get inspired following along with his journey.
After college, Pete’s main goal was getting to New York City. He started as a sales rep for Office Depot and eventually switched roles into pharmaceutical sales. While Pete had all the benefits and financial security he wanted, he felt like he wasn’t being challenged. Pete and his now wife were passionate about travel and started a blog called “Quarter For Your Crisis.” They started building a community behind people struggling to find their career path after college and looking for their purpose. They both quit their full-time jobs and ran this blog while backpacking through Central and South America.
They were hit by culture shock when returning and were trying to figure out what to do next. Both agreed they did not want to go back to the corporate world. Pete and Jordan combined their skills to start building websites and offering digital marketing services. They went door to door to build up their initial client base. They took these experiences to figure out what services they wanted to expand into. They pivoted into new fields, such as social media marketing and digital ads. Their successes led them to specialize in the wedding industry and later creating online course offerings for other businesses. Pete and Jordan kept learning what they were passionate about and how they could help the most people.
During this time, they struck a deal to be sponsored and we’re given an RV to travel and work remote full-time across the country. While their business was thriving, their heart wasn’t in it anymore. Pete and Jordan were starting a family and thinking about their purpose moving forward. This led them to give up the successful services business and starting Kairos Journal, which helps people grow their faith while being more present in their day to day lives. If you are interested, you can find their journals or other product offerings here!
Check out the conversation as we dive into the following:
- How backpacking abroad changed his perspective
- How he started a business to not go back to the corporate world
- How being willing to fail opens new opportunities
- How being authentic is the key to finding your purpose
- How you have 3-5 hours a productive work a day and finding that time frame helps achieve better work life balance
Listen to Pete share his story and get inspired with his amazing advice to people thinking about following a similar path.
Today, we are joined by Jeff Chenault, who quit his job over 15 years ago. While in college, Jeff was asked by one of his professors to work with her design company full-time. With only one year to go, Jeff decided he was learning more working, didn’t want more debt, and decided to dropout of school jumpstart his career. While working for her, Jeff knew he would eventually start his own design company.
However, since he was 15 years old, Jeff had dreamed of design album covers in the music industry. A job in this industry was extremely tough to crack, so he picked jobs, such as working at Hallmark Cards, to build up his skillset and resume. Then he began going to shows and going backstage to offer musicians his design services. After 7 years of effort, Jeff broke into the music industry.
Jeff became VP as he worked his way up the ladder. However, something was missing. He was now a manager and not doing any of the creative work which he was truly passionate about. When he turned 35, Jeff decided to make the leap and start his own design agency called ELEVEN07.
Fast forward 15 years and Jeff still runs his own company. He continues his belief of not taking a job for just money. He finds work that he finds interesting and is passionate about. If you are looking for design work, check out his website here!
Check out the conversation as we dive into the following:
- How he never finished his college degree and why it never mattered
- How he worked his way into the music industry by pitching musicians backstage at shows
- Why he wasn’t fulfilled as he was rising the corporate ladder
- How he built an company to focus on the creative work that inspires him
Listen to Jeff share his story and get inspired with his amazing advice to people thinking about following a similar path. Check out the full conversation on YouTube or Spotify by clicking the links below.
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Know someone who should be on Why I Quit? We’re looking for all types of stories and people to feature at the top of the show. To nominate yourself or someone else, email dave@foundersapproach.com and tell us your name, where you’re from and what you want to talk about.
Today, we are joined by Alex Bullington, who has not followed a traditional career path. After passing his CPA and joining an accounting firm, Alex quickly realized that accounting was not where he was meant to be. Alex and his friend, Greg DiNardo, decided to quit their full-time jobs to start a mobile app called Arbit. This application gave users the ability to post and interact with polls before Instagram, Snapchat, or Twitter had this feature.
After self funding the initial app, Arbit was getting traction. They were able to raise funding with some of their early investors being NBA players. They kept iterating the application and experimented with marketing strategies, which led to hitting over 100k users. While the user base was growing, Alex began focusing on revenue. This led to pivoting the company as a B2B service for interactive polling in the market research space.
While growing the company’s sales, Alex caught the attention of Ceros, which is a cloud-based interactive content creation platform for marketers and designers. Ceros acquired Arbit and hired Alex and Greg full-time to launch an internal Ceros product called Markup. They used their experience from Arbit to scale this new product to over 100k users.
With all of this success, Alex was thinking about next steps. He had spent the last 6 years in the startup world, felt burnt out, and was ready for a change. These experiences helped him to realize that he was passionate about product marketing and led him to his new role as a manager of Product Marketing at CB Insights. He started his new full-time role over 3 months ago and is so excited about his new opportunities.
Check out the conversation as we dive into the following:
- How he decided to quit his full-time job to start an app
- Why his friends and family all thought he was crazy, but how they supported him throughout the process
- How stressful it was going through an acquisition while launching a product for his new company
- How he has scaled two different products over 100k users
- How his entrepreneurial path led him to find what he is passionate about
- Why he is excited going back into a corporate full-time job
Listen to Alex share his story and get inspired with his amazing advice to people thinking about following a similar path. Check out the full conversation on YouTube or Spotify.
Subscribe now
Know someone who should be on Why I Quit? We’re looking for all types of stories and people to feature at the top of the show. To nominate yourself or someone else, email dave@foundersapproach.com and tell us your name, where you’re from and what you want to talk about.
Today, we are joined by Mike Malloy, who has followed an amazing professional journey with 13+ years of experience as a Deloitte management consultant, Waveborn sunglasses CEO, Halcyon Incubator program director, Georgetown adjunct professor, trusted advisor, mentor, sales consultant, and career coach.
Over this time, Mike has quit his job twice to follow entrepreneurial ventures. The first time Mike got inspired by a social mission sunglasses company that donated a portion of profits to fund life-changing cataract surgeries around the globe called Waveborn. While the company achieved some incredible growth and milestones over his 6 years, he dealt with shutting down the company and all of the financial implications of that decision. While Mike’s positivity is infectious, he is extremely open and vulnerable about the hardships and isolation that he went through during this period.
This led to him paying it forward with other entrepreneurs and helping them navigate the difficult waters of starting their own business. He turned this skill into a full-time job as the the Program Director of the Halcyon Incubator, which equips early-stage social entrepreneurs with the support they need to transform their ideas into scalable and sustainable ventures in order to change the world.
Over the past year, Mike quit his full-time job again to be able to continue working remote from the beach. Learning from his previous mistakes and experiences, he was much more thoughtful about the process the second time around. He founded Malloy Industries, where he focuses on helping growth-stage companies build systems and repeatable processes to scale from $500k to $5M revenue. He looks for clients with impactful work that he is passionate about, while prioritizing his own lifestyle design. If you are interested in connecting with Mike, you can check out his website here!
Check out the conversation as we dive into the following:
- How one cold email changed the trajectory of his entire life
- His rule of thumb of how much revenue to generate before quitting your job
- How entrepreneurship is a life sentence and the isolating side that does not get talked about
- How he was much more thoughtful quitting his job the second time
- How he values lifestyle design more than a reliable paycheck
- Why he believes entrepreneurship is a positive sum game and how we can all help each other
Listen to Mike share his story and get inspired with his amazing advice to people thinking about following a similar path. Check out the full conversation on YouTube or Spotify by clicking the links below.
Subscribe now
Know someone who should be on Why I Quit? We’re looking for all types of stories and people to feature at the top of the show. To nominate yourself or someone else, email dave@foundersapproach.com and tell us your name, where you’re from and what you want to talk about.
Today, we are joined by Katelyn Magnuson, who is on a mission to change the work week. With an accounting background, she job hopped to continually increase her salary and skillset with the ultimate goal of starting her own business.
Katelyn was always running her business, The Freelance CFO, part-time on the side to help startups and small businesses with their accounting needs. As COVID hit, Katelyn floated the idea of being laid off at her work. Once she was officially let go, she had the time and bandwidth to go all in scaling her business.
Over the past year, she has added 4 new employees and grown sales 3x. Most importantly, she focused on building a company that she wants to work at. Her company has a 30 hour work with an extremely competitive salary and generous benefits. They focus on efficiency versus total work hours. Most recently, Katelyn went viral on TikTok with a post getting over 1.7 million views discussing her company set-up!
Check out the conversation as we dive into the following:
- How she specifically picked jobs to build complimentary skillsets to eventually run her own business
- How her company met every one of her needs but she still felt suffocated
- How she ran her business part-time of the side until she was ready to go full-time running her own businesses
- How she built a company around a 30 hour work week
- Why she went viral on TikTok and how the work week is changing
Listen to Katelyn share her story and get inspired with her amazing advice to people thinking about following a similar path. Check out the full conversation on YouTube or Spotify by clicking the links below. If you are interested in her services, check out her website here!
Subscribe now
Know someone who should be on Why I Quit? We’re looking for all types of stories and people to feature at the top of the show. To nominate yourself or someone else, email dave@foundersapproach.com and tell us your name, where you’re from and what you want to talk about.
Today, we are joined by Cassie Collier, who is the first ever guest on “Why I Quit.” After graduating college, she joined the Peace Corps in Nicaragua. She became inspired teaching entrepreneurship classes to high schoolers, which was the start of her entrepreneurial bug.
When returning to the states, Cassie received her masters at Harvard University and ended up on Wall Street joining Deutsche Bank full-time. While working full-time, she couldn’t shake the idea of starting her own business. One day, Cassie and her sister, Jackie, invented a board game for their family, which was based on their memories and family traditions. This brought them so close, which sparked the idea of starting a company called Bundle to build custom board games for others.
As Bundle kept growing, Cassie was planning on leaving her full-time job. However, she was able to strike an agreement with her company to adjust her schedule to part time. Fast forward 3 years, Cassie and her sister and still running Bundle. For anyone looking to learn more about her company or purchase a board game, check out the site here!
Check out the conversation as we dive into the following:
- How the resilience of entrepreneurs in Nicaragua inspired her to start her own business
- How she felt she was losing creative entrepreneurial side at Deutsche Bank
- How she was looking out for her perfect co-founder for years, which turned out to be her sister, Jackie
- How she was able to keep health insurance and some financial stability by not quitting but going part-time
- How she founded a board game company based on a game they originally invented for their family
Listen to Cassie share her story and get inspired with her amazing advice to people thinking about following a similar path. Check out the full conversation on YouTube or Spotify by clicking the links below.
This is the first podcast we have ever recorded. Episode one and we already are making mistakes. We promise the sound quality will get better each episode. We will keep working to improve every week. If you have any feedback, please send in the good, the bad, and the ugly below!
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Know someone who should be on Why I Quit? We’re looking for all types of stories and people to feature at the top of the show. To nominate yourself or someone else, email dave@foundersapproach.com and tell us your name, where you’re from and what you want to talk about.