Every week, host Greg Head interviews a successful software founder who started, grew, and sometimes sold a valuable software company—without big funding.
Over $8 billion of founder equity value has been created by just 130 SaaS founders interviewed on this podcast so far. That’s an average of $60 million founder of equity value created by each company.


Brian Kesselman is cofounder and now CRO of Skematic, a compliance management and workflow software for financial services firms. Brian was a lawyer for major financial services companies who helped manage internal compliance ...


Brian Dosal was the founder and CEO of BrightGauge, a software company he bootstrapped and grew to almost $10M ARR with his brother before successfully selling the company in 2019. BrightGauge was a business analytics and dashboard ...
Howard Gottlieb started Read-A-Thon in 2012 as a reading-based fundraising platform that helped students raise money while boosting education. Their easy platform and simple fundraising approach created amazing results. The Read-a-Thon business ...
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 ...

Joe 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 ...
Brian 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 ...

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 ...
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 ...

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 ...
Stuart Draper founded Stukent, an innovative ed-tech company that provides simulated internships for business students. Stukent started by focusing on high-quality digital marketing education for colleges and universities using up-to-date ...
John Stewart created and sold an engineering services business, then grew a Salesforce integration services company before building some early software products. One of their software experiments allowed Salesforce customers to see and interact ...
Kyle York was the Chief Revenue Officer of Dyn, a bootstrapped cloud infrastructure company that he helped grow and sell to Oracle for over $600 million. He then led product strategy and acquisitions in Oracle's cloud infrastructure group ...
Mike Kovarik is the founder and former CEO of Attribytes, a software company he started, grew, and successfully sold in just over five years. Mike was a data analytics leader at large food distributors, where he discovered a chronic challenge ...
Brothers David and Chris Sinkinson attended Queen's University in Ontario, Canada, when David learned of the problems maintaining the blue emergency phones on campus. He proposed a location-aware mobile safety app, so Chris built it himself, ...
Rob Farrow was an experienced marketing executive and his wife Christina Farrow was a successful professional wedding planner. They discovered there was no good software for wedding planner pros, so they decided to build software themselves. ...
Ian Manners was a successful consultant for pharmaceutical companies in the US when he discovered a major problem that needed a software solution. Big pharma companies provide financial assistance funding for patients who require their drugs ...
Mike Trasatti spent 10 years in the automotive dealer software business before he found an auto dealer in Iowa who had built is own complete software system. They partnered up in 2008, and Mike became the first CEO of the spinout software ...
Jeff Corn is the co-founder and former CEO of Virtuance, one of the US's leading real estate photography and marketing providers. In 2010, Jeff was in the real estate investment business and wondered why it took $10,000 and nearly a month to ...
Joe McMenemon and his college roommate, Brendan, knew they wanted to start a business together. They had run their college fraternity chapter and saw the problem of managing members and collecting payments. So they lived frugally and built ...
Rand Fishkin is the founder and former CEO of Moz, a leading SEO software for marketers created in 2007 that grew out of the active followers of Rand's popular SEOmoz blog. Moz grew quickly to over $30 million in revenue by 2013, having raised ...
Nathan Hirsch, co-founder of FreeUp, shares his journey of building and selling the company and his other business adventures. FreeUp provides clients with pre-vetted virtual assistants (VAs) and freelancers in an online marketplace.
Nathan ...
Ian Brodie, the co-founder and CEO of Levanta, shares his journey of building a successful SaaS company in the affiliate marketing space.
Levanta is an affiliate marketing platform for Amazon sellers, enabling them to connect with content ...
Gregg Scoresby founded CampusLogic in Phoenix in 2021 to provide software for colleges and universities in the US to make it easier for students to apply for college loans and grants online. Initially self-funded, CampusLogic raised investment ...
Esben Friis-Jensen and his cofounder, Sebastian Seilund, teamed up in 2021 to create Userflow, a no-code user onboarding product for SaaS companies. This week, it was announced that Userflow has been acquired by Beamer, a maker of product user ...
Antony Ceravolo is a successful two-time startup founder from Adelaide, South Australia. He started his career in investment banking but left in 2002 to start a DVD rental business in London that raised funding from big VCs and Amazon. It grew ...
Harry Hopkins is co-founder and CIO of Viewgol, a medical billing technology software and services company based in Dallas, Texas. Viewgol was started in 2017 by three founders who got the product and revenues going before hiring additional ...
Jafar Owainati was a mechanical engineer before he got an MBA in entrepreneurship and decided to start a software company with two friends. They looked at many ideas before building software to help sales engineers respond to Requests for ...
Bernardo Carvalho Wertheim is a worldly entrepreneur who grew up in Rio de Janeiro, Brazil, and then moved to the UK to go to school and start his career in advertising. He kept traveling and eventually settled in Santiago, Chile, where he ...
When Patrick Randolph discovered that doctors' offices lose 20% of appointments due to patient cancellations and no-shows, he set out to design and test a solution. QueueDr was created to fill those open slots with patients in the waitlist ...
Raj Khera has had three exits in his long career as a software entrepreneur and leader. His first company, GovCon, grew in the late 1990s to help government contractors easily access new contracts up for bid by the US government. Their ...
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 ...
Oliver Low worked for Microsoft and then MySpace in London before creating a successful digital agency in 2010 with two friends. Their agency grew fast and was profitable, so they invested in building software apps to solve problems that they ...
Lloyed Lobo is the co-founder and former president of Boast.ai, a leading platform to help software companies in the US and Canada redeem available government tax credits. Technology-powered Boast.ai was launched in 2017 after starting a ...
Patrick Fingles grew a successful roofing company with hundreds in the Baltimore-Washington DC area. In 2013, they created software to help new salespeople estimate, quote, and close new roofing sales. They started selling the software to other ...
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 ...
Sam Knight is the co-founder and former president of BOLT Software, a project management and scheduling software for the construction trades that build residential homes. Sam helped lead the BOLT team as it grew before the company was sold and ...
Joshua Strebel started a small SEO and website agency in the early 2000s after graduating from university. Joshua and his wife Sally experimented with website hosting using WordPress with low monthly fees while they ran their services business ...
Dave Savage was a top-producing mortgage loan officer in the early 1990s who used computers and software to help him sell more. He became a software entrepreneur by creating a new software solution for loan officers to help them educate their ...
Patrick Campbell wasn't expecting to be an entrepreneur when he grew up, but after his first few jobs, he struck out on his own in 2012 to create a software company to help SaaS businesses optimize their pricing. Price Intelligently quickly ...
Jon Nordmark founded eBags.com in 1998 as one of the first Internet e-commerce companies and grew it into the largest online retailer of luggage, bags, and travel accessories. Jon was previously a successful corporate executive who led ...
Perry Rosenbloom moved to Boulder, Colorado, in 2011 and started a small business offering digital marketing and custom website services. After building a website for his mother-in-law, an independent therapist, Perry created a scrappy ...
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 ...
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 and Scott started selling it. MVP Systems ...
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 companies with its ...
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 registration experience for endurance ...
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 them manage their large ...
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 was acquired by Fiverr in 2019 and ...
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 not being used, so he started Echosec Systems to find a practical use for those insights.

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 it easy for car buyers to find, buy, and finance a ...

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 learn music using ...
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 ...
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 ...
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 ...
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 buying, ...
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 ...
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 sold before he started LawLytics ...
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 popular CRM and accounting software ...
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