Every week, host Greg Head interviews a successful software founder who started, grew, and sometimes sold a valuable software company—without big funding.
Scott McCausland was an experienced software sales leader who decided to go out on his own in 2008 to build a new software business. His technical cofounder built the first version of their new software … Listen to this episode
Oliver Palmer helped start a mobile app development agency in Sydney, Australia that built simple apps for early mobile phones. When the iPhone launched, Tigerspike grew very fast by creating branded mobile apps for large … Listen to this episode
Sandeep Kumar quit his job working for an Indian consulting company to start a software company in 2005, when product-focused startups were not common in India. For the next 10 years, they experimented with product … Listen to this episode
Sarah Hum studied graphic design in university before she discovered she loved to help software startups create new products. She moved to Silicon Valley to work at Facebook as a product designer, but a side … Listen to this episode
Mark Abbott was an active investor and board member for 20 years when he realized that most of the 100+ companies he helped were not good a their "business fundamentals." The fundamentals of setting long-term … Listen to this episode
Craig Letton quit his corporate sales job in 2011 to take over his parents' small printing business in Scotland. It was his first time running a business and he learned hard business lessons quickly. Eventually, … Listen to this episode
Jeff Matlow is a serial entrepreneur and a crazy triathlete and long-distance runner who found a way to put those passions together in a crazy software startup. He saw an opportunity to create a better … Listen to this episode
Howard Gottlieb created and sold several businesses before starting a school fundraising website in 2003 called Easy Fundraising Ideas. It grew into the most popular Internet website for school fundraisers. He experimented with many business … Listen to this episode
Scott Pickard didn't know he was embarking on a 15-year software entrepreneurial journey when he signed on to manage a horse veterinary practice in Calgary, Canada. But they had built some internal software to help … Listen to this episode
Josh Cameron and three university friends started a scrappy software company in Brisbane Australia just after graduating. They had run the popular college bar where they discovered there was no simple software solution to track, … Listen to this episode
Joe Griffin recently left his job of 8 years as co-CEO of ClearVoice, a company that he and co-founder Jay Swanson started in 2014 out of their digital marketing agency business in Phoenix, Arizona. ClearVoice … Listen to this episode
John Francis is a general partner at Stout Street Capital, a venture capital fund based in Denver, Colorado. Stout Street has made 70 small seed and pre-seed investments in software startups outside the big tech … Listen to this episode
Zach Moreno was a full-stack developer and coding instructor in Northern California in 2015 when he discovered audio podcasts. There wasn't a remote podcast software for recording high-quality audio over the Internet, so he decided … Listen to this episode
Karl Swannie was a geographer working in the scenic city of Victoria, British Columbia, Canada, when he started analyzing social media data based on location. He quickly saw there was valuable real-time information that was … Listen to this episode
Brad Redding calls his first startup a “successful failure.” It didn’t end well, but he learned several very important lessons that helped him be more successful with his second startup, Elevar. Now the bootstrapped SaaS … Listen to this episode
Daniel Yuabov was a 22-year-old IT manager in New York who wanted to buy a new car. He was so frustrated with the buying experience that he started a software company called Carvoy to make … Listen to this episode
Melissa Kwan created her first software company in 2014 and then sold it in 2019. It was extremely difficult to start and even harder to grow, but it’s how she learned what not to do … Listen to this episode
Seth Radman created, grew, and sold two music app startups in his twenties. A saxophone player in his college marching band, Seth was passionate about helping musicians and school band directors to improve how they … Listen to this episode
Dougal Cameron created Golden Section to provide support and practical funding to SaaS founders with deep experience in select vertical markets. Their founder-first approach is different than the traditional VC or private equity investment model … Listen to this episode
Sean Meister was a sales professional and leader with a successful career selling hospital and medical supplies before he left to join his long-time friend who had a vision for a new software company serving … Listen to this episode
Thomas Brown creatively bootstrapped his software company and ran it as a very small "lifestyle" business before committing to growing his SaaS business with a larger team.
Thomas was an independent insurance claims adjuster in the … Listen to this episode
Nick Santora bootstrapped Curricula for five years with his co-founders before raising $3M in practical funding and then getting acquired in 2022 for $22 million.
Nick and his co-founders quit their jobs to build innovative story-based … Listen to this episode
Jeremy Clarke created, grew, and sold his software company in a most unusual and successful way:
He grew WebMerge to $5M revenue by just himself for 6 years before hiring his first and only employee, a … Listen to this episode
Luke Hohmann was an engineering and product management leader at Silicon Valley startups before he became an acclaimed author and speaker in the enterprise software development world. He used funding from his consulting business—plus revenue … Listen to this episode
Steve Gelley created two successful businesses and learned important lessons before he and a cofounder self-funded a third startup that was acquired in only 18 months for a big prize.
Steve started his entrepreneurial journey by … Listen to this episode
Hamid Shojaee is a technical founder and serial entrepreneur who created several software companies and dozens of products in the last 25 years. He sold his two software companies in 2021—Axosoft and Pure Chat—and now … Listen to this episode
Dan Jaffe is the founder and CEO of LawLytics, a practical website marketing platform for small law firms. Dan was a practicing lawyer before he became an internet entrepreneur with his first venture, which he … Listen to this episode
Rafael Zimberoff was CEO of ShipRush, a software company he founded in 2001, then grew and eventually sold in 2017 to Descartes Systems Group for $17 million. Rafael started ShipRush as an add-on product for … Listen to this episode
Jonathan Cronstedt, also known as JCron, was the president of Kajabi software from 2016 through 2021 as he helped the company grow past the early startup years. JCron is a savvy entrepreneur, digital marketer, and … Listen to this episode
Todd Watson is the owner and CEO of Showit, a popular no-code website builder and platform for designers and photographers. Todd is a native of Phoenix, Arizona where he started as a videographer before joining … Listen to this episode
