Jason 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.”

• Jason Fried on LinkedIn
• Jason Fried on Twitter
• 37Signals on LinkedIn
• 37Signals website
• Basecamp website 
• HEY website
• Ruby on Rails website

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.

Quote 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.”

• Russ Perry on LinkedIn
• Design Pickle on LinkedIn
• Design Pickle website
• Colorado River Partners

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.

Sunando Bhattacharya spent 13 years as a business leader in managed IT services companies in India before starting his own cloud tech services business. This company grew slowly and an opportunity arose to create a software product for one of their clients. Two years later, in 2019, they had a few more Apiculus product customers and focused more on the product.

Apiculus is a complete "cloud-as-a-service" software platform for data centers to offer, sell, deploy, and manage cloud data services for their own customers. They focused on smaller data centers in emerging markets, including Nepal, Oman, Rwanda, and others in the Middle East and Africa.

The Apiculus business grew as it turned into a product-first company. They overcame many challenges during COVD and with customers and partners that didn't work out.  In 2024, the company was acquired by Yotta, and Indian cloud technology company, in a strategic acquisition. 

Quote from Sunando Bhattacharya, founder of Apiculus

"Somebody asked me what one thing you want for your company. I said I wanted my company featured on Great Places to Work. It's very important that the team that works with me finds this a great place to work.

"The only secret ingredient for tech companies is people. It's people who make the technology. And if you take care of your team, you take care of your people, you will always do well.

"This isn't just for services companies. Talent and ability are important. But for somebody to bring their best every day to work and deliver something world-class, which is world-beating, it needs a very different level of passion. And that passion will only come from your team if you take care for them."

•  Sunando Bhattacharya on LinkedIn
• Apiculus on LinkedIn
• Apiculus website
• Yotta Data Services website

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.

Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.

Steve Wolfe and Nate Grossman are co-founders at Growth Street Partners, a growth equity firm focused on investing in early-stage B2B SaaS companies between $2M-$6M in ARR. They discuss how growth equity funding works for SaaS founders and how it allows entrepreneurs to maintain control while still benefiting from investment and liquidity.

In this expert episode, Steve and Nate get specific and share real examples of how SaaS founders use growth equity to win bigger, when it can be a good fit for founders, and how founders scale their businesses and win with multiple exits. They also describe:

• Why Growth Street Partners focuses on practical founders with growth equity.
• How growth equity is different from traditional private equity and venture capital.
• Why successful founders are “learn-it-alls” with a growth mindset.
• How founders can achieve multiple exits through strategic partnerships.
• Why building a strong team is essential for scale-up success.

Quote from Steve Wolfe, co-founder of Growth Street Partners

“We know that when entrepreneurs have fun, their companies do much better.  When founders continue to feel real ownership in their business and in the success of their company, they do a lot better, too. 

“So we set up our whole firm to enable that. We are investing to own just 20% to 50% of a business, so the founder still controls the company. We go to them with execution ideas and proven frameworks and approaches, but we are really just giving them the tools to make better decisions themselves.

“They know they make the decisions in the end, so they will make sure that it’s successful. There’s something beautiful about that relationship and about helping that founder get to where they want to go while still feeling like they did it.”

• Steve Wolfe on LinkedIn
• Nate Grossman on LinkedIn
• Growth Street Partners on LinkedIn
• Growth Street Partners website

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.

Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.

Raj Bhaskar is a successful two-time practical software founder with one exit. In 2000, he started his first software company, VisualHOMES, to provide a comprehensive financial management software to public housing agencies. With no outside funding, the business grew to serve 65 regional providers serving 2 million residents before Yardi Systems acquired the company in 2010. 

After he left Yardi two years later, Raj and his brother launched Hurdlr to reach the wider small business market with a simpler accounting and tax management software than Quickbooks. They started selling their online accounting software to small businesses, but eventually they returned to their original vision to build embedded (white label) accounting that works inside other software. 

Hurdlr has grown steadily and has served over 1.3 million small businesses in its 13-year history. Raj invested his own money for many years and a little outside investment. The company is now “lifetime profitable” and growing quickly with 25 employees. Raj loves his work and has no intention of selling the business anytime soon.

Quote from Raj Bhaskar, cofounder and CEO of Hurdlr

“I ran my previous software business for 10 years before I sold it. And Hurdlr is now over 10 years old. These days, I’m talking about the next 10 years and the next 10 years after that. The next decade and two decades from now, because it’s relevant and because I think we’re just getting started.

“I’ve seen inflection points in markets, and our market is finally ready. That’s the part we didn’t have any control over. So, in my view, there is no finish line. This is the starting line where we now have all these assets and need to let more people know we exist.

“It’s crazy to say after 10 years that this is just the beginning. So I could say probably 20 years from now, looking backward, OK, these are the phases, but I’m in new territory and I know this will be a sustainable and growing business for a long time.”

• Raj Bhaskar on LinkedIn
• Hurdlr on LinkedIn
• Hurdlr website

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.

Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.

Vince Hsieh is a two-time entrepreneur who has started, grown, and sold two industrial tech companies that included software and either an RFID or GPS device in the solutions. His second venture, Geoforce, raised a non-dilutive funding round to accelerate global growth before being successfully acquired by private equity investors LLR Partners in 2019.

Their royalty-based funding round allowed Geoforce to skip a VC funding round, preserving founder equity and fueling their growth. After their acquisition, Vince shares that the founders saved tens of millions of dollars in founder equity value with their non-dilutive funding from Cypress Growth Capital.

Vince eventually joined Cypress as a general partner, working with capital-efficient SaaS founders to help them build more enterprise value. Vince shares how royalty-based funding can be a very useful funding approach in specific situations.

Quote from Vince Hsieh, partner at Cypress Growth Capital

"Skipping a VC found by using non-dilutive funding made a huge difference to us at Geoforce, especially compared to my first startup where we did not have royalty-based funding in the middle from Cypress. We had just venture capital and then eventually sold to private equity.

"So the math of royalty-based funding is amazing because from the time of our funding from Cypress to the time we sold to private equity, our equity, our value more than 10x'd. But we didn't pay back Cyprus anything close to 10X.

"Had we raised several million dollars in VC funding with equity, there would have been easily tens of millions of dollars of difference between having done royalty-based funding and equity funding. And that tens of millions of dollars of difference went into our shareholders' pockets, including the founders and our friends and families who invested earlier."

• Vince Hsieh on LinkedIn
• Cypress Growth Capital on LinkedIn
• Cypress Growth Capital website
• Geoforce website

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.

Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.

Bill Spruill had a successful sales and executive career with two exits before he and his cofounder struck out on their own in the location verification market serving financial and e-commerce companies. Sales grew slowly for several years as they scraped by and kept going. Eventually, they pivoted the company to focus on identity verification and know-your-customer (KYC) with a new approach, and sales grew steadily every month. 

Global Data Consortium (GDC) partnered with data providers and fintech companies who became loyal customers, trusted partners, and potential acquirers. The company grew over 100% for several years, acquiring new partners and adding experienced leaders to their small team. In 2022, the London Stock Exchange Group (LSEG) acquired GDC for $300 million in an all-cash deal. 

Bill talks about the lessons he learned in their patient growth journey, the challenges of trying and failing to raise startup capital, their frugal focus, their incredible acquisition story, and what he is doing now as a successful former founder. 

Quote from Bill Spruill, founder of Global Data Consortium (GDC)

“There was a low point in the business where we were just struggling with, Why are we doing this? Are we going to make it? So we stepped back and said, We’re gonna do something very simple. We’re gonna focus on 10% growth every month, which wasn’t a big number then.

“We focused on moving the needle 10% every month with revenue. And then you get into the power of compounding. Every month we moved it 10% and we would celebrate. We kept moving that needle 10%, 10%, 10%.

“Eventually, that number got to be very sizable where we cracked through $5 million in revenue and we paid off all of our debt. And we became profitable and we kept growing fast. That unleashed the ability to accelerate our growth, growing 100% a year as we got bigger.”

• Bill Spruill on LinkedIn
• Global Data Consortium (GDC) on LinkedIn
• Global Data Consortium (GDC)  website, now called LSEG Risk Intelligence
• London Stock Exchange Group (LSEG) website

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.

Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.

Troy Munson has been a successful enterprise SaaS sales rep for several years, but he wanted more control over his life—and eventual financial independence. So he launched his own small startup on the side. He learned a lot and sold it before launching his second side gig software company, which he sold for a little bit more. 

He started his third side-gig startup, Dimmo, in 2023 to allow enterprise software buyers to watch product demos without talking to sales reps. With the help of co-founders, Dimmo is now live and revenues are growing fast. With a little angel funding, Troy was able to go full-time to make Dimmo successful quickly.

Troy is a fast-start SaaS founder, testing ideas and launching companies when traction starts. He and his cofounders don’t think about running this forever, but they do want to create a valuable company and achieve financial independence as successful practical founders.

Quote from Troy Munson, CEO of Dimmo

"I'm like this fast-starter person. I built Vocul and Refurl, my first two side gigs, from an immediate thought: This is annoying, this should be solved. Let me solve it, let me sell it. And then let me see if there's any interest.

"With Dimmo, I just wanted to create extra income on the side. The hope for Dimmo was to pay my mortgage with a side gig. I knew software buyers just wanted to watch software demos. So let's just make it like a YouTube for software demos and then we'll just take some sort of revenue.

"It blew up on LinkedIn when we launched and grew faster than expected. I had to go full-time and I'm so happy I did. It feels great. I hope I never go back to the side gig guy. I also hope I never go back to any sort of any sort of W-2 work. I'm buying my freedom."

• Troy Munson on LinkedIn
• Dimmo on LinkedIn
• Dimmo.ai website

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.

Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com. 

Wes Bush is CEO of ProductLed, a coaching and education company that has helped almost 500 serious SaaS founders to succeed with product-led growth strategies, tactics, and execution. These include freemium products and free trials, where the product itself creates the awareness, engagement, and enthusiasm to buy before any human intervention (aka “the required sales demo”).

Wes has written two successful books, Product-Led Growth and The Product-Led Playbook, describing key ideas, frameworks, approaches, and examples for SaaS founders. In this expert episode, Wes shares his expertise for SaaS founders, including these topics:

• Defining product-led growth
• Transitioning from sales-led to product-led
• Common mistakes in product-led growth
• Identifying challenges and solutions for user experience
• Pricing strategies in product-led growth
• The future of product-led growth in SaaS

Quote from Wes Bush, CEO of ProductLed

“The PLG model you choose doesn’t matter. Not a bit. Freemium, free trial, credit card up front, whatever. You can make any of those work. That’s not the question. What matters in PLG is the actual outcome that we hope somebody will get from our product-led experience?

“Does your free motion actually have a transformation in it where they can feel they will grow bigger, save time, and do cool stuff? Because if you don’t have that, it’s literally just, “Hey, look around, see for yourself, see what you can do in this product. That’s not real value.”

“What is your PLG outcome that creates that transformation for the user? There has to be tangible value for the user before they ever consider buying. That’s what customers want when they buy software now–Show me value first before I think about buying from you.”

• Wes Bush on LinkedIn
• ProductLed on LinkedIn
• ProductLed website
• Free Product-Led Growth book
• Free Product-Led Growth audio book
• The Product-Led Playbook book

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.

Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com. 

Michael McAllister is the founder and former CEO of The CE Shop, the leading provider of pre-licensing and continuing education for real estate professionals in the U.S. Michael started The CE Shop in 2005 by distributing existing training materials from a continuing education provider. They quickly created their own online education solution and proceeded to expand with specific content and compliance elements for each state. 

The CE Shop grew steadily without outside funding for 15 years by building a 5-star team, adding partner channels, expanding to new states, and providing more content for the pre-licensing of new real estate agents. The company grew to over 130 employees and expanded faster during COVID.

Michael successfully sold the company to private equity investors in 2020 for a “9-figure exit,” meaning more than $100 million, to Waud Capital. On this podcast, Michael shares the realities of their growth journey, including their special emphasis on culture, people, and practical expansion as a bootstrapped technology business. 

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.

Quote from Michael McAllister, Founder of the CE Shop

“When founders sell their companies, I'd suggest they need to do it when they hold all the cards. During our first experience with a serious potential buyer, we asked for a lot of information about their business. It was reverse due diligence since I’d be the biggest private investor in their company.

“We were two weeks before closing, and I called our banker and said, this is really frustrating that we’re asking for all this information and not getting it back. Unless we do, we may need to pull the plug on this deal. We held all the cards. We had a great business. We didn’t need to sell like we were completely in the driver’s seat. 

“It was really difficult but we decided to pull the plug on the deal. The biggest thing was that there was a real mismatch in core values. Our core values were foundational to who we were and who we are as a company. One of them was doing what we said we’d do. And it was a $100 million question. It was a big deal.“

• Michael McAllister on LinkedIn
• The CE Shop on LinkedIn
• The CE Shop website
• Waud Capital website (acquirer)

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.

Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.