Seeking Scale: Recent Episodes
Andy Baldacci and Craig Hewitt
Craig and Andy begin by talking about the weather and what’s been happening during the past week. Craig says he’s finally feeling recovered from traveling, and Andy discusses the illnesses his 4-year-old has been dealing with for the past few weeks. He says that this has helped him focus on only what’s most important for ... Read more
Craig and Andy discuss a Twitter interaction that they had. Craig tweeted about wanting a tool that shows trials month-to-date and how it compares to the previous month. Andy wonders what he would do with that information. Andy thinks that it’s too much noise and that this might not be the best comparison to make, ... Read more
Andy says he’s feeling a little manic and running on a lot of caffeine. Craig says that things are looking better from where he is. Trials are up in the last few months, and sales are up as well. This is due to some changes that are starting to pay off. Craig and Andy discuss ... Read more
Craig says he’s been writing more, including starting a newsletter and working on his personal website. He’s interested in the intrinsic benefits of writing. Craig also wants to invest more in himself. Andy wonders if Craig writes much in general. He explains that he doesn’t journal, but when brainstorming, his default is to write it ... Read more
Andy talks about the good traction they’ve had recently that’s starting to show now. They just shipped a big update and received a great reaction to it. It came together faster than similar things have in the past. Craig explains that Castos launched a free set of tools that’s starting to get traction now. Andy ... Read more
Today Craig and Andy discuss how to think about options. Andy talks about making sure everything is ready for a large influx of new trials. They’re already up 140% over last month, and he says people are more likely to buy in mid-season. He talks about taking on too much and learning about prioritization as ... Read more
Craig and Andy discuss the importance of prioritization and the importance of capital efficiency. Craig explains that Warren Buffet cites Apple as an example of a capital-efficient company and wonders about whether his company is a capital-efficient company. Andy says that often, people spend much of their time doing things that have no meaningful impact ... Read more
Andy and Craig talk about social media strategies for their respective brands—SaberSim and Castos—related to the HubSpot State of Inbound Marketing Trends 2022 Report. Should they be doing more on social media? If yes, what and how? Is it worth it? People do not follow brands but individuals and influencers on social media. Craig stresses ... Read more
Andy and Craig talk about product-led growth being the most dangerous movement in SaaS startups. To convert, a product needs to be built that is relevant to the intent of SEO for growth-led products that deliver on what’s promised. Andy rants about a tweet on product-led growth companies building products that sell themselves. However, Andy ... Read more
Andy and Craig talk about focusing on delegation, prioritization, and productivity. Based on feedback, a lot of stuff that people do is not really effective. What tools, books, and other resources do they recommend? Andy’s been busy leading up to and since the birth of his baby. He just can’t do everything at work and ... Read more
Does your marketing have a defined purpose, structure, or place in the funnel? If not, then you should not be doing it because it’s ineffective, creates noise and uncertainty for prospective customers. Craig and Andy revisit cohesive marketing. There are stages that people go through to become a buyer. Andy has brainstormed and thought about ... Read more
Craig and Andy talk about learning to just say, ‘No.’ What is meaningful, matters most and what does not? Most likely, 20-50% of what you are doing are things that you should not be doing. Craig shares how his company retreat went really well. They dedicated time to talk about and reflect on objectives and ... Read more
Craig and Andy talk about finances. But first, founders need to give themselves permission to do what they want to feel better and guarantee a great start to the workday because too often the afternoon falls apart. Craig wants to declare that he does not start work until 9 a.m. to drop his kids off ... Read more
Craig and Andy talk about pre-planning versus figuring things out as they go. What’s driving what and how do you get there together to grow? After a weekend getaway to unwind, Andy is back to prep and quarterly planning before paternity leave. Focusing on the right things makes a big difference because it’s so easy ... Read more
Craig and Andy talk about the shift in mindset when it comes to taking time off from your business and getting others up to speed or being more productive and strategic as a founder to enable others to reach goals and be successful. Andy’s stress level steadily increases as the due date nears for the ... Read more
Craig and Andy talk about building for now versus for the future when it comes to their roles and responsibilities as founders. Both are looking to take themselves out of the critical aspects of their businesses. Andy is focused on significantly shifting what he is working on and hiring an executive assistant and copywriter before ... Read more
Craig and Andy talk about current events in tech, including Paddle’s acquisition of ProfitWell and what else is going on in the bootstrapped versus enterprise world, economy, and ecosystem. Andy views the acquisition/merger as the ProfitWell brand and team continuing to do what it has been doing, but what will happen to the leadership (i.e., ... Read more
Craig and Andy talk about managing technical debt. Is more data needed? Do you need to be driven by metrics? What is possible versus realistic? Who do you need to make happy—your customers or your team members? Andy shares how a big release has been in quality assurance (QA) for about a month, which shows ... Read more
Craig and Andy talk about refining the hiring process and lessons learned. Get prepared and things ready, but it’s still not going to be what you expect it to be. Andy and his wife are expecting a child. So, he is wondering how he’ll handle being a father and founder. He needs clearly defined processes ... Read more
Craig and Andy talk about product feedback loops. What and who’s needed to get feedback sooner than later to be productive and build a product or add features/functionality? Craig announced that he decided to leave Bench and switch to GrowthLab Financial for bookkeeping services. Also, he has hired a new developer who will be starting ... Read more
Craig and Andy talk about finding a life-work balance. How do you separate the two, especially for those who work remotely? Working from home does not work for everyone. Sometimes, you want to work and be productive. Other times, you want to spend time with your family and friends doing something fun in the sun. ... Read more
Craig and Andy attended MicroConf and provide a recap. Both left the conference feeling energized, full of ideas, and with a purpose to grow and scale. Whether it’s selling, buying, or making an impact through ClickFunnels, community, HubSpot, or Freshdesk, they want to be more effective, productive, and successful. Craig enjoyed being around like-minded people ... Read more
Craig and Andy talk about quarterly goal setting, shifting objectives and key results (OKRs), and attending conferences to learn some stuff, be inspired, and reconnect with friends/colleagues. Andy is preparing for MicroConf (April 3-5). Even though it corresponds to the opening day of baseball season, he is not needed as much at SaberSim. By following ... Read more
Craig and Andy talk about cohesive marketing as a challenge to rank higher and convert customers. What can go wrong, right, and areas of improvement? Be opinionated, helpful, logical, and think about the purpose of each piece of content by being intentional and targeting the ideal customer. Craig’s company has optimized SEO and content marketing ... Read more
Founders often feel the pressure to be a CEO by offloading tasks to focus their time on higher-value or higher-leverage items. Craig and Andy talk about considerations of founders’ time value. Craig has realized that being a founder should mean that he optimizes for what he wants to do. because founders should do exactly what ... Read more
Craig and Andy talk about not having time to focus on or dive deep into anything, such as content marketing and business development to generate revenue, cash flow, and reach goals/results. Slow down, chill out, and don’t try to do everything because time is the best thing for growth and company maturity. Craig mentioned how ... Read more
Craig and Andy talk with candor and constructive criticism about prioritizing, promoting, and positioning accounting, taxes, bookkeeping, and other financial services, software, and products. Andy rants about how Craig lied about recommending Bench to anybody starting out in business and handling bookkeeping. Finding inherent flaws have impeded progress and become the bane of his existence. ... Read more
Craig and Andy talk about reducing uncertainty by implementing and integrating objectives and key results (OKRs), key performance indicators (KPIs), and entrepreneurial operating systems (EOS) for businesses. A healthy work/life balance is a goal that makes for happy employees. Andy is making steps toward better organization, process, and possibly following the EOS methodology. Performance goals ... Read more
Craig and Andy talk about increasing certainty by checking the objectives and key results (OKRs) process. There should never be any surprises, exceptions, or clarifications. A single source of truth makes a business run smoothly, like a well-oiled machine. Andy discusses how processes need to be put in place to handle pain points as a ... Read more
Craig and Andy talk about base hits and grand slams of product strategy decisions. How can improvements be made to priorities and productivity to make an impact and get results? Craig is trying to be a more vocal and present founder by making daily posts about fundraising, bookkeeping, cash runway, and sales information via Castos ... Read more
Craig and Andy continue their discussion about administrative roles, responsibilities, tasks, and software as a service (SaaS) tools to make better product processes, priorities, and decisions. Craig thanks listeners who helped with compliance and state filings. He onboarded with MainStreet to get tax credits. Also, Craig is outgrowing Bench Accounting. His accountant’s recommendation—go from cash-based ... Read more
Craig and Andy talk about admin things – from bookkeeping to payroll and tax compliance. These business operations and functions may be boring to some but necessary for all. Andy sometimes got stuck because he did not know what or how to perform specific admin tasks. He started with Gusto but switched Mosey to Justworks ... Read more
When things go wrong in their business, how do Craig and Andy respond? For what it’s worth, they need to know what to worry about and how to communicate to offer guidance and protect customers’ time, money, and data. After rolling out objectives and key results (OKRs) at Castos, Craig shares how job functions, responsibilities, ... Read more
Craig and Andy reflect on the holidays and taking vacation time away from their businesses. Did you miss them? What happened? Did work still get done and was progress made? Craig wonders what is the point of him in his business? He is finally giving himself permission to do what he wants to do in ... Read more
Craig and Andy reflect on their professional and personal achievements in 2021 and prepare for more progress and growth in 2022. Craig talks about amazing 2021 accomplishments at Castos and gives an update on objectives and key results (OKRs) for the first quarter of next year. Things have to get done and/or delegated to measure ... Read more
Craig and Andy talk about prioritization in marketing and evaluating growth strategies. Where do opportunities exist—more website visits, customers, or trials? Craig plans to focus on getting more customers by increasing the trial-to-paid conversion ratio to be more effective and valuable. Increasing prices is not the best option for upside potential. Also, Craig’s company has ... Read more
Craig and Andy talk about unplugging during vacations and putting objectives and key results (OKRs) on the rocks to manage goals. Their businesses are left in capable hands and they plan to hire even more help. Andy has returned to the office following his honeymoon. He unplugged for the most part and rarely checked Slack ... Read more
Craig and Andy talk about lessons they have learned in sales. Andy has minimal sales experience, while Craig has a ton of experience and continues to learn from others. Craig shares how 90 days have passed since his new account executives were onboarded. The salespeople learned foundational things since they came in to break things ... Read more
Craig and Andy talk about preparing to take time off as founders of growing businesses. When getting ready for a vacation or holiday, they need to wrap up, hand off, and document responsibilities at work. Andy knows he needs to get a lot of little things done before Thanksgiving and going on his honeymoon. Some ... Read more
Craig and Andy talk about building real, scalable companies that are not dependent on them as founders. Considering what they do with their time on a day-to-day basis is critical to grow. Craig discusses how Castos had a really strong last month for sales. Now, he understands why forecasting and pipelines are really important. Craig ... Read more
Craig and Andy talk about executive assistants (EA), virtual assistants (VA), chief of staff (COS), and much more to get things delegated and done, oh my! Andy enjoyed gambling for work and taking a legitimate business expense for SaberSim at DraftKings – not all for not while living the dream. Also, Andy is working with ... Read more
Craig thinks everyone spends too much time, money, and effort on their products. Even extremely bad products can be incredibly successful. So, should focus be put on hiring more salespeople, marketers, or developers? Craig recommends reading, Radical Focus. Craig updates listeners on how the two new AEs at Castos are two months in and doing ... Read more
Craig and Andy talk about whether they are ready to take the next step and control their own destiny by going from being individual contributors to leaders to build a bigger company faster. The problems are different, but don’t get easier as a company grows. For founders and CEOs, changing responsibilities involves enabling, empowering, and ... Read more
How can a company double or triple its growth rate? Craig and Andy talk about ways to be more deliberate when it comes to scaling content marketing. Craig is ready to accelerate growth at Castos. His options include content and SEO as well as paid acquisition – all of which Castos does already and both ... Read more
Craig and Andy revisit the quality assurance (QA) process, as well as talk about sales and marketing hires to add bandwidth and balance priorities. Craig provides an update on hiring an internal QA person or external agency. The best way to QA is in the development process with unit and integration tests. Instead of hiring ... Read more
Craig and Andy talk about the need for an in-house or external quality assurance (QA) agency to grow a business and team that plans for unexpected consequences and interactions. Currently, Craig is in the midst of a team retreat and identifying the need for a QA solution. There is no plan, documentation, or accountability for ... Read more
Andy and Craig talk about being busy and a lot going on like always. But some of the parts of the business seemed slow, especially for Andy. It took a lot of focus, discipline, and the right team to get something done right. Andy reports on the refactor/redesign rollout and pricing updates of SimSaber’s Daily ... Read more
Andy and Craig talk about what if you wake up every morning, ready to do your job? Once you cross the finish line and get big things done, do you need to do retrospectives and post-mortems of projects to be successful? Craig’s teams do them after every sprint and they consist of discussing what do ... Read more
Andy and Craig talk about taking time off to unplug from the business, delegating tasks and responsibilities, and holding team retreats. Andy knows he doesn’t have to delegate everything or worry when he goes away for a few days or on a business trip. He knows someone will notify him if something goes seriously wrong. ... Read more
Andy and Craig provide updates on refactoring, redesigning, rebranding, and releasing new versions of their websites and web apps. Andy has been working on a big redesign at SaberSim and plans to publicly release the new version of the app soon. It has taken a lot of time, tweaks, and improvements to get it right. ... Read more
Risks and Efforts vs. Results: Andy and Craig talk about sales onboarding tools and delegating task-level work. According to Andy, it’s a forcing function to focus as football season starts and build winning lineups with SaberSim. When deadlines loom, he figures out and delegates what doesn’t matter or needs to get done right now. What ... Read more
Andy and Craig talk swag for team members, customers, and partners. What’s the purpose of it? Where and on whom should startups spend money to be successful? Craig shares how Castos created swag with a simple slogan in the form of T-shirts and hoodies for team members in the past using Printful. Also, he plans ... Read more
Craig and Andy talk about how the concept of deep versus wide can apply to every aspect of your life and business. Do you do a bunch of things? Does your app have lots of features and serve different types of people, or is it the best at one specific thing? Andy and Craig share ... Read more
Craig and Andy talk about the peaks and valleys of seasons from a business perspective. They discuss the importance of being intentional and deliberate to make progress and remain profitable. After taking time to recharge, it’s time to get back to work. During the summer, Craig has been working less. Being intentional and taking microsteps ... Read more
Craig and Andy talk about taking time off, finding ways to recharge, and balancing their well-being by hiring resources to grow and move their businesses forward. Craig had a difficult time finding and hiring a front-end developer. But he did make an offer to a female developer in Chile that was accepted. She will start ... Read more
Craig and Andy talk about how and when they do strategic planning to grow their businesses. Craig tries to strike a balance between planning to strategically get work done. Although he tends to spend time planning and working, Craig needs to consistently relay and communicate strategic plans to make leaders and team members aware of ... Read more
Craig and Andy talk about creating alternative content to communicate with customers and community as the silver bullet to success. Make it meaningful and valuable. Andy embraces the MVP mentality to engage customers and offer support via office hours, FAQs, videos, documentation, and other content. Also, strategy sessions offer a deeper dive into specific subjects ... Read more
In this episode, Andy and Craig talk about the recent fundraising round that Craig closed at Castos. There are lots of lessons learned in the fundraising process, and now that the round is closed Andy and Craig explore how Castos will put these new financial resources to work. In this episode Andy and Craig talk ... Read more
Craig and Andy talk about hiring for sales, support, and other roles. Dealing with what they don’t know involves hiring great people with the right strengths and skills. Andy shares how business travel has made him fall behind on day-to-day work, but he is still able to oversee high-level progress. He is going to take ... Read more
Craig and Andy talk about meetings and team dynamics. When there’s so much going on, it’s difficult to gain clarity and be productive and effective. Andy discusses how finding a rhythm for meetings helps to structure the company. It’s still a work in progress. Andy has brief stand-up to longer sit-down and detailed meetings with ... Read more
Out of office – what will break if or when you are away? Nobody wants to be a micromanager or be told what to do. Craig and Andy talk about how and what they plan to do to be better managers and lead their teams. You know you’re getting older when you want to leave ... Read more
Craig and Andy talk about making progress by providing onboarding updates for new employees and customers. Craig discusses improving the onboarding process and sequence for employees, which includes Sam, the new Head of Growth. He will start on Monday and brings senior-level experience generating revenue. As for onboarding customers, Craig has had challenges. Once some ... Read more
Craig and Andy talk about ways to build a community and drive engagement. Are their self-limiting beliefs holding back their businesses and resources from being successful and producing solid results? Things need to change to continue growing. What needs to change? Strategizing sales and marketing or products and services? Andy’s business has reached a revenue ... Read more
Craig and Andy talk about the big picture of a content strategy for support and success. There’s a fine line between constantly creating content and making it simple for customers to find. It involves analytics, access, and ease of use. Andy’s business is going well. There are ups and downs as always, but progress is ... Read more
Craig and Andy talk about getting out of the day-to-day business a little bit more to take an actual vacation, not a workation where they are stuck in a hotel room working while their family is having fun on the beach. Craig and Andy know they have to build up a team to take on ... Read more
Craig and Andy talk about experimenting with product marketing tools/apps to onboard and guide new hires and customers. It’s worthwhile, but takes time and money to try new ways to keep people engaged and enthusiastic. Craig is feeling like a few more key people will round out things nicely at Castos, but the roles are ... Read more
Andy and Craig talk about investing in growth by bringing on new hires because communication issues can get people stuck on something that doesn’t matter. Give them and yourself permission to make progress. Andy is thinking about a new season of stress as the boys of summer return to play baseball. At the same time, ... Read more
What are ways to work on the right things? Andy and Craig talk about whether to avoid distractions and daydreaming to regain focus and productivity. Andy feels like he is scattered, losing focus, and not making much progress. For him, managerial duties feel like busy work. What should he do right now and in the ... Read more
Andy and Craig talk about the challenging aspects of company culture and hiring people, internally or not, for specific roles to set them up for success. Currently, Craig is looking to hire in the areas of development, support, and sales. He describes Castos’ company culture as the actions that you take around your values. COVID ... Read more
Use it or lose it?! Everyone has expectations of work/life balance and needs a break once in a while to recharge, even though most of them don’t feel like they can totally unplug from the business. Craig and Andy talk about company culture related to its impact on the intersection of dev and product. Andy ... Read more
Craig and Andy talk about the winds of change to grow their companies–counts, churn, communication, coaching, and culture. Craig attributes Castos having its greatest growth month ever to an increasing trial count and churn. It also takes delivering and managing better service, expectations, and communication. The Castos Academy has proven to be a successful and ... Read more
Craig and Andy talk about building out their teams to grow, rate, and scale their businesses. To scale a business, there are a lot of unknowns. Now, Andy knows what’s possible when the right people are hired. He finalized terms of investment and got new investors. So, there’s money in the bank. Craig has made ... Read more
Framework for Hiring: What did you do? What was the best/worst part? What did you learn? Why did you quit? Do your homework, think quickly, talk clearly, and be autonomous. Craig and Andy talk about the hiring and recruiting process to add resources to their businesses. They value their time and your time. Stress never ... Read more
Craig and Andy talk about not falling into the trap of thinking only about fundraising, but about building and growing a business. Craig discusses different options to adding resources, including revenue-based financing, traditional loan, and equity. There isn’t a single best right or wrong, but easiest or hardest way. Growing the company is all that ... Read more
Craig and Andy talk about moving from the maker to the manager. How do their priorities and responsibilities change? What are the things they want to keep doing, even if it’s not the best use of their time or skill set? How do they find and hire the best people? The three jobs of a ... Read more
Andy and Craig are optimistic about making marketing messaging worthwhile in 2021. Do fewer things that are effective to develop authority and make a positive impact. Andy talks about projects in the pipeline that are starting to come together and move forward. However, he is still unsure of how to navigate the power of product ... Read more
Craig and Andy strategize, seek clarity, and set goals for 2021: Hire, refocus priorities, and pivot toward specific areas and positions. Craig continues to discuss fundraising, loans, and other financial options to accelerate growth and put resources toward the Castos business. Pretend you are big, before you are to scale. Andy talks about how difficult ... Read more
Sea of blue busyness—Craig and Andy talk about trying to get things done before the end of 2020 and the new year begins. Help wanted! Craig is hiring a full-time executive assistant via Support Shepherd, an agency that finds top virtual assistants in the Philippines. Why? He needs to delegate to prioritize activities that he ... Read more
Craig talks about receiving an email pitch from a venture capital firm interested in raising money. Always ask yourself: Do you want to be in a situation where you have a partner whose goal is for you to exit the company with as much money as possible, so they can get their return? Craig’s personal ... Read more