Podcast
Practical Founders Podcast
Hosted by Greg Head · EN
Tune into the Practical Founders Podcast with host Greg Head for weekly in-depth interviews with founders who have built valuable software companies--without big funding.
45episodes
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#178: Approaching $20 Million ARR with 99% Annual Retention - Dan MacDonald
Jan 901:08:21Tap to summarizeDan MacDonald is the founder and CEO of BIS Safety Software, based in Edmonton, Canada. He didn't start in safety or software—he came from retail and leadership training before an unexpected pivot led him into online safety systems. That shift eventually became a long-term bet on a "un-sexy" problem that companies can't ignore. Today, BIS Safety serves more than 2.5 million users across high-risk industries like construction, mining, transportation, and energy. The company generates roughly $25M CAD in annual revenue, employs about 200 people globally, and runs one of the stickiest SaaS platforms you'll find—with less than 1% annual logo churn. After nearly 20 years of bootstrapped growth, Dan is beginning a staged exit, starting with a minority secondary sale and planning a control transaction in a few years. Along the way, he shares hard-earned lessons about product obsession, compounding customer retention, and why steady execution beats hype. Key Takeaways Extreme Retention Matters — Less than 1% annual churn created compounding growth without aggressive sales spending. Product Over Sales — BIS focused on usability and depth first, letting word-of-mouth drive most early growth. Customer-Funded Start — Early customers paid to build the first LMS, avoiding dilution and premature fundraising. Long Bootstrap Reality — The first decade involved no salary, deep personal risk, and constant financial pressure. Enterprise Power, End User Simplicity — Power users get depth, while users see an interface designed to feel effortless. Quote from Dan MacDonald, Founder and CEO of BIS Safety Software "So at that time when I started the business, there was an awakening kind of moment of realization. It hit me big. I'm reading hundreds of business books and reading about Bill Hewlett, Dave Packard, Sam Walton, and many others. "I'm listening to the things they're saying, the ways they're thinking, And all I'm thinking is, my God, they think like me, they're just like me, they're normal people, they're just like me. And that was kind of the first awakening realization to say, they're not superhuman! That gave me the confidence to build the business and believe in the future. I never thought there's a pot of gold at the end of the rainbow it was never about the money. It was just some burning thing inside me that just I need to do this.I was just driven to do to do this. I felt like it was just this is what I'm meant to do." Links Dan MacDonald on LinkedIn BIS Safety Software on LinkedIn BIS Safety Software website Podcast Sponsor – Lighter Capital This podcast is sponsored by Lighter Capital. In the last 15 years, Lighter Capital has helped over 600 software and SaaS founders secure simple, non-dilutive financing to grow a little faster—without giving up any precious equity or board seats to investors. Simple debt funding from Lighter Capital can range from $50K to $10 million, with straightforward terms, no personal guarantees or covenants, and up to a 4-year payback period. Go to LighterCapital.com to apply and get a quick pre-qualification. Then talk with their experienced team to create a practical funding plan to achieve your goals. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com. Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Transcribe →#177: Building Multi-product Vertical SaaS With a Tiny Team - Robin Eissler
Jan 201:10:50Tap to summarizeRobin Eissler is the founder and CEO of BoosterHub, a vertical SaaS platform built for high school booster clubs. After selling her prior business as a private jet broker, Robin volunteered to run a local booster club and discovered a messy problem run with spreadsheets, emails, and manual accounting. She decided to build a single system that could actually handle it. BoosterHub now serves nearly 600 booster programs, representing over 100,000 users. With just two full-time employees and a small dev team, the company processes more than $40M in transactions across payments, fundraising, merchandise sales, and accounting. Annual contract value typically runs $1,500–$2,000 per customer, with strong retention and expanding usage. Still independently-owned and bootstrapped, BoosterHub is approaching $1M ARR and profitability. Robin shares lessons on building complex software with a tiny team, selling to volunteer buyers, surviving seasonal revenue swings, and why slow, compounding growth can create durable SaaS businesses without venture capital. Key Takeaways Tiny Teams Work - Two employees plus contractors can build serious SaaS with focus, systems, and modern tooling. Sticky Beats Big - Hundreds of small customers compound more reliably than a handful of enterprise deals. Seasonality Is Real Education-adjacent - SaaS must survive cash spikes and winter slowdowns without panic. Founder-Led Marketing - Consistent content from the founder still drives inbound growth in niche markets. All-In-One Wins in Verticals - Being the system of record makes churn low and customer value expand naturally over time. Quote from Robin Eissler, Founder and CEO of BoosterHub "The numbers are much better than what we projected. so we're starting to see that compounding effect is really what's happening is there's just enough users and enough people in the system that they're using more of the add-on products and we're processing more volume. "So it's starting to have that compounding effect. And so I really just admitted to myself this month, like, I think we're seeing it. "I think we're finally seeing it. I feel like, OK, maybe for me, it's almost that I can exhale. I've been holding my breath for four years, so maybe I can breathe." Links Robin Eissler on LinkedIn BoosterHub on LinkedIn BoosterHub website Podcast Sponsor – Full Scale This podcast is sponsored by Full Scale, one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at fullscale.io. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com. Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Transcribe →#149: How Partner-Led Sales Built A $7M Bootstrap SaaS Business - Sameer Narkar
Jun 20, 2025Tap to summarizeSameer Narkar is the founder and CEO of Konnect Insights, a global SaaS company based in Mumbai that provides an omnichannel customer experience platform to consumer brands in 100 countries. Sameer created Konnect Insights in 2015 to help customer service teams respond to customers who mention their brands on social media. The product and company have expanded from a slow start working through marketing agencies in India to now distributing through ISV partners in all major global regions. The Konnect Insights product includes social listening, ticketing, reputation monitoring, and social media analytics. They have grown to 140 employees, hundreds of customers, and $7 million ARR--without any outside funding. In this episode, Sameer talks about: Selling through agency and ISV partners to grow efficiently Competing with large, well-funded software companies How he thinks about how AI can help them compete Why he hasn't sold the company or raised outside funding Quote from Sameer Narkar, founder and CEO of Konnect Insights "When you start a software company, you have all odds against you. You don't have enough money. There's no reason why customers would trust you against the established products. There is a 99% chance that you'll fail. "But if you're really passionate about what you're building, then don't look too far ahead. Try to achieve your smaller goals or get from zero to one. So just build something and get some early customers. We figured out a way for agencies to be interested in selling our solution to bring it to market. "Then meet directly with your end customers. It's very easy for tech founders to sit in the office and build a product the way they think. That doesn't work. Many founders think that if they take a half-baked product, they won't get another chance. But that's not the case. You need to build relationships to help you improve and grow.." Links Sameer Narkar on LinkedIn Konnect Insights on LinkedIn Konnect Insights website The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Transcribe →#132: No-Code SaaS Platform Bootstrapped to 75,000 Customers – Rachit Khator
Feb 14, 202501:03:43Tap to summarizeRachit Khator is the founder and CEO of Stackby, a no-code spreadsheet and database app builder that allows business users to create powerful spreadsheet-like applications with data links, automations, and workflows. Rachit and his team of 34 employees live in Surat, India, north of Mumbai. Stackby started when Rachit was working for a corporate venture firm in Michigan, doing repetitive manual data imports and analysis in Excel. He hired a developer to build a better tool and started to sell Stackby to early customers. They followed customer feedback to build an inexpensive and easy-to-use app that competes well with VC-funded competitors like AirTable for specific use cases. This bootstrapped company has grown in 4 years to serve 75,000 free and paid business customers. Now they are profitable and growing at 15% per month, upselling free business users to paid plans. Rachit has big ambitions for Stackby to serve millions of customers–and be an example success story in the Surat software community. Links Rachit Khator on LinkedIn Stackby on LinkedIn Stackby website Podcast Sponsor – Full Scale This podcast is sponsored by Full Scale, one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at fullscale.io. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.
Transcribe →#130: Profitable Product-Led Growth to $30 Million Before Big Exit – Joe Hyrkin
Feb 7, 202501:07:58Tap to summarizeJoe Hyrkin is the former CEO of Issuu, a content publishing platform for interactive marketing content. Issuu allows you to easily publish printable and PDF materials in various formats to websites and social media. It’s a global product-led success story with millions of customers and a successful and sustainable business. Issuu was started by four Danish founders before the company was moved to Silicon Valley in 2013 when Joe was hired as the CEO. Joe ran the company for almost 12 years, growing it profitably most years to almost $30 million in revenue before it was sold in mid-2024 to Bending Spoons, an Italian holding company that is an active acquirer of software companies. Joe talks about working with their early venture capital investors with a practical and patient approach. In 2021, Issuu raised $20 million in debt to invest in marketing and address technology issues, which helped them grow faster before being acquired. Quote from Joe Hyrkin, former CEO of Issuu “From 2016 to 2020, we ran Issuu profitably, with what I like to call a ‘pro-grow’ approach—profitable and growing. Then, we raised debt to grow faster to about $30 million in revenue. The final year before we sold, we got back to profitability. So we got to profitability twice. “By being profitable, you’re committing to your customers that you’re going to be around and that they will not have to go find some other solution. You’re communicating to your team that this company can be counted on. In 2024 and 2025, everybody wants profitability, unless you’re an AI company. “Not having a profitability plan actually creates a lot of risk. I’m not saying you always have to be profitable, but you always have to have a foundation to know how we get to profitability. It’s a different way of thinking.” Links Joe Hyrkin on LinkedIn Issuu on LinkedIn Issuu website Bending Spoons website Podcast Sponsor – Cypress Growth Capital This week’s podcast is sponsored by my friends at Cypress Growth Capital. For 15 years, Cypress has provided non-dilutive growth funding to bootstrapped SaaS founders, including many successful founders I’ve interviewed here on this podcast. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.
Transcribe →#129: On Freedom and Ownership With Software Entrepreneur Brian Hamilton
Jan 31, 202501:06:34Tap to summarizeBrian Hamilton is one of America’s most successful entrepreneurs and a leading expert on entrepreneurship. Today, Hamilton serves as chairman of software company LiveSwitch. He is known for his pioneering work in fintech, his advocacy for small businesses, and his commitment to criminal justice reform. As the founder of Sageworks (now Abrigo), America’s first fintech company, Hamilton developed technology that translates complex financial data, empowering millions of small business owners. Sageworks struggled and grew slowly for 10 years before pivoting to serve local banks and credit unions with financial tools to assess the creditworthiness of their small business loans. The practical SaaS company grew steadily and very profitably to more than 400 employees when it was sold in 2018. Through Inmates to Entrepreneurs and the Brian Hamilton Foundation, he encourages entrepreneurship as a means to economic opportunity. Hamilton’s work has been showcased by major media outlets like CNBC and Good Morning America, and he starred in ABC’s Free Enterprise TV series, an award-winning show based on Inmates to Entrepreneurs. Quote from Brian Hamilton, founder and former CEO of Sageworks "Being the founder of a tech company is like this: You're in a tunnel, it's dark, you're on your hands and knees, you're going through that tunnel, you're groping your way through, keep moving forward. "I know it sounds like such a BS, but we've all been there. I'm telling you, that is the picture: you're in this huge sewer tunnel, it's dark. You just gotta keep moving. Just keep chipping away. You do that, and you will get momentum somehow. "It's like compound interest. You start with a dollar and how does it turn into $10? You build momentum a little at a time. I've got to listen every day. I'm knocking off making the product better. You develop the physical property of compound interest and things will get better." Links LiveSwitch website Brian Hamilton Foundation Podcast Sponsor - Cypress Growth Capital This week’s podcast is sponsored by my friends at Cypress Growth Capital. For 15 years, Cypress has provided non-dilutive growth funding to bootstrapped SaaS founders, including many successful founders I’ve interviewed here on this podcast. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.
Transcribe →#128: Solving a Challenging SaaS Growth Puzzle - Scott Desgrosseilliers
Jan 24, 202501:04:33Tap to summarizeScott Desgrosseilliers is the founder and CEO of Wicked Reports, a leading multi-touch marketing attribution software for SMBs who use paid online advertising. Scott is a data and analytics expert who saw the costly limitations of simple performance reports from popular ad platforms. Wicked Reports was started as a bootstrapped software company in 2016 to serve smaller companies that spend millions on digital ads and other marketing, including email, SEO, and digital events. Determining which marketing activities drive incremental revenue is a tricky puzzle to unravel, but the payback of those insights is huge. Scott raised a little angel funding and a little SaaS debt and is still going strong with 28 employees and is figuring out their growth and retention puzzle to accelerate growth. Quote from Scott Desgrosseilliers, founder and CEO of Wicked Reports "We had offers, and we could have raised VC funding early on, but then the growth rate we would have had to hit was too high, which didn't make sense for our business. "A competitor of ours took $20 million from a similar VC, and then they had to cut a third of their team. I'm not saying anything against them. They have a nice product and they seem like good guys. They hired a ton of people and didn't hit the growth number, so they had to whack a bunch of them. "Money isn't always the answer. I'm sure there are cases where it solved all sorts of problems, but most VCs want to invest when you already have growth and net revenue retention at 120% when the efficient growth problem's already solved!" Links Scott Desgrosseilliers on LinkedIn Wicked Reports on LinkedIn Wicked Reports website Podcast Sponsor - Full Scale This week’s podcast is sponsored by Full Scale, one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at fullscale.io. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.
Transcribe →#127: Scaling SaaS with Efficient Growth and Practical Funding - Bryan Forrester
Jan 17, 202501:11:52Tap to summarizeBryan Forrester is CEO of Boostlingo, a leading on-demand platform for language live interpretation services that is growing quickly and can become a very large company. Boostlingo now has 160 employees and over 17,000 language interpreters who use their software to manage jobs, coordinate schedules, deliver interpreting services, and get paid. Bryan raised some practical funds from angels to start the company in 2016. The company grew 50% or more every year since then. In 2021, Boostlingo raised a growth equity round of funding from Mainsail Partners to provide capital for efficient growth and buy out some early investors. Boostlingo has since made several small acquisitions. Quote from Bryan Forrester, CEO and co-founder of Boostlingo "Our customers love our software, and our NPS is very high. So when we have customers who love our software, we have high retention and low churn, and our customer costs are really good. When all of that is combined, why would you slow down the growth? "Why would you take your foot off the gas pedal and be very profitable? And we raised a growth equity investment from Mainsail and started spending more on efficient marketing. And it worked. It worked. "What would have happened if we didn't take that small investment with our growth equity partner? We could still have had a positive outcome. We may have already sold the business. But we wouldn't have grown as big as we have become in this very big market." Links Bryan Forrester on LinkedIn Boostlingo on LinkedIn Boostlingo website Mainsail Partners website Podcast Sponsor - Cypress Growth Capital This week’s podcast is sponsored by my friends at Cypress Growth Capital. For 15 years, Cypress has provided non-dilutive growth funding to bootstrapped SaaS founders, including many successful founders I’ve interviewed here on this podcast. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.
Transcribe →#126: Jason Fried on 20 Years Bootstrapping BaseCamp at 37signals
Jan 10, 202500:57:57Tap to summarizeJason Fried is the co-founder and CEO of 37signals, makers of the popular Basecamp project management software, which is still growing and very profitable after 20 years. He is going long and still having fun as an engaged CEO, building great products with great marketing that stands out. Jason has long advocated for software founders to avoid VC funding and build sustainable businesses that are great for customers and generate healthy profits for the owners. His best-selling book, Rework, shared his practical approach for entrepreneurs. In this wide-ranging interview, Jason discusses these important topics: How the core principles of Basecamp remain focused on simplicity and essential tools for project management after 20 years. Why Basecamp targets small businesses, avoiding the enterprise market that many competitors chase. Why software should fit the needs of the user, rather than forcing users to adapt to complex tools for big companies How profitability, not growth, provides the freedom to innovate and explore new ideas. Why competing against your costs is more important than competing against other companies. How small teams have the agility to win against big companies. Quote from Jason Fried, co-founder and CEO of 37signals “My sense of independence has always been important to me. That’s why I became an entrepreneur: to do things the way I wanted to do them. Otherwise, why be an entrepreneur? It’s true when you work, you’re working for your customers. That’s always going to be true. But you still have a sense of independence. You get to make your own decisions. “What people don’t realize is when you raise money, you don’t really work for yourself anymore. You really don’t. You work for someone else’s schedule, for someone else’s fulfillment, for someone else’s return. That never appealed to me. “I want our products to explain themselves. I want our success to explain ourselves. I don’t want to have to explain myself on a quarterly basis to somebody who’s trying to get a return out of me. I’m not interested. So for all those reasons, it just wasn’t right to raise big funding.” Links Jason Fried on LinkedIn Jason Fried on Twitter 37Signals on LinkedIn 37Signals website Basecamp website HEY website Ruby on Rails website Podcast Sponsor – Full Scale This week’s podcast is sponsored by Full Scale, one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at fullscale.io. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.
Transcribe →#125: Created the World’s Largest Subscription Service for Creative Design – Russ Perry
Jan 3, 202501:08:10Tap to summarizeQuote from Russ Perry, founder and CEO of Design Pickle “The game for practical SaaS founders really comes down to recognizing that there is a large market size for very boring niche companies. Finding that niche is the fastest path to success. Don’t be afraid to be boring and specific. “If I were to do Design Pickle all over again, I would have just picked a vertical niche, like we are the graphic design provider for feline mobile cutting trucks or something. There are easily 10,000 mobile pet grooming businesses in the United States, so probably just cat groomers. “We just went super broad when we started, and it’s been fine, but it would have been easier for us to have focused on a niche. When you have such limited resources and time and money and capital, having that narrow niche makes it easier to maximize all those dollars and investments.” Links Russ Perry on LinkedIn Design Pickle on LinkedIn Design Pickle website Colorado River Partners Podcast Sponsor – Full Scale This week’s podcast is sponsored by Full Scale, one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at fullscale.io. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.
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