Every week, host Greg Head interviews a successful software founder who started, grew, and sometimes sold a valuable software company—without VC funding.


Dinakara Nagalla built EmpowerMX over more than a decade to digitize aircraft maintenance for major airlines like American, Southwest, and United. Starting from deep domain experience inside aviation IT, he tackled ...


Jordon Comstock is founder and CEO of BoomCloud, a vertical SaaS company serving dental practices with patient membership software. He started the company scrappy and bootstrapped, with no outside funding, after years in ...


Josh Ho is the Founder and CEO of Referral Rock, a bootstrapped referral marketing platform serving SMBs that rely on multi-step, relationship-driven sales. Starting in 2015 as a solo developer consulting on the side, Josh ...


Raju Patel founded eShow over 25 years ago after building a speaker portal for a magazine company and realizing he had a repeatable software product. What began as a one-man shop in suburban Chicago evolved into a robust ...


Dharshan Rangegowda, founder of ScaleGrid, left a decade-long engineering career at Microsoft to solve a painful database operations problem he had lived firsthand. After early missteps selling to enterprises, he shifted to ...


Darryl Pahl is the co-founder of DFnet, a Seattle-based company providing clinical trial data management software and services. Along with his wife and co-founder, Lisa Ondrejcek, Darryl started the company more than 20 years ...


Vince Mayfield is cofounder and CEO of TalkingParents, a co-parenting app for communication and coordination used by divorced parents raising children. Cofounder Stephen Nixon was a lawyer with family cases who recognized the need ...


Henry Valentino is the founder and CEO of EConnect, a leading provider of facial recognition software for casinos and stadiums, ensuring venue security and compliance. He founded EConnect in 2009 and pivoted several times before ...

Josh Turley is the CEO of RTA Fleet Management, a fleet management software company that his grandfather founded in the 1980s and operated as a small family business for decades. Then Josh’s father ran the business until 2015, never ...


Sameer 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 ...


Roy van den Broek is the founder and CEO of Rentman, a rental business management software platform for event and media production companies. Roy built software for his event equipment rental business in the Netherlands. He ...


Gopal Krishnamurthy is the founder and CEO of Lumel, which has a suite of products focused on enterprise performance management (EPM). Their apps allow users to plan, report, and analyze data using modern native app frameworks ...
Shalin Jain is the founder and CEO of HappyFox, a successful bootstrapped company that provides modern help desk management software for customer service, support, and IT management organizations. Shalin and his small team in India built many ...
Richard Change is co-founder and CEO of PFA Solutions, the provider of FirmView software. FirmView® is the leading carry and compensation management platform for private equity investors to manage their internal compensation from fees and ...
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 ...
Last year I interviewed three-time software founder Matt Watson on this podcast about his successful practical founder journeys. Matt leveraged offshore software development talent in his last two SaaS companies to staff up quickly and grow ...
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 a friend in 2007 to create a ...
Subramanyam Kasibhat has created dozens of products in many different industries. He and his wife were contracted by a friend to build a software solution for a manufacturing plant for a German company. Seven years after they started with their ...
Mike Roberts is the founder and CEO of SpyFu, a leading competitive research tool for marketers and entrepreneurs with over 15,000 paid customers and hundreds of thousands of free users. SpyFu was launched in 2006 and has been a profitable and ...
Praveen Ghanta graduated from MIT with degrees in computer science and economics and worked for various financial services companies after trying his hand at a software startup. Working in his spare time, he built a product and recruited a ...
Wissam Tabbara is a serial entrepreneur who has created multiple software startups in Seattle since 2009 when he left Microsoft where he was a software development manager. He led multiple startup technology teams and now is an experienced CEO ...
Gregory Shepard is a serial entrepreneur who has created and sold 12 companies, including marketing software and ad technology companies. In 2016, he sold two of his bootstrapped software companies, AffiliateTraction and AdAssured to eBay for ...
Gopal Krishnamurthy was an early BI and data analytics expert working for a large company when he left to start a BI consulting company called Visual BI in 2010. Visual BI grew to over 300 employees serving enterprise customers as an evangelist ...
Matt Watson was a two-time software company with two successful exits before he was 40 years old. He started his first company, VinSolutions, in his basement in Kansas City in 2006. VinSolutions started by helping auto dealers upload photos of ...
Vivek Bhaskaran was a computer science student in college who worked on an online survey project for a professor in the marketing department. After university, he built a new survey tool with a fellow software developer while they still held ...
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 to create ...
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 strategic sales rep. It's an incredible ...
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 is an active investor and ...
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 sales leader who shares the ...
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 a friend in 2007 to create a ...
