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.
Seth Hassell and Clint Ethington are the co-founders of Genius Monkey, a programmatic ad tech platform with proven targeting, tracking, and attribution for optimized results. Seth and Clint were childhood friends who worked on many ...
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 ...
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 ...
Bryan Forrester is CEO of Boostlingo, a leading on-demand platform for live language interpretation services that is growing quickly and can become a very large company.
Boostlingo now has 160 employees and over 17,000 language interpreters ...
Russ Perry is the CEO and founder of Design Pickle, the largest subscription-based business for creative design services. It's a SaaS-like tech-enabled services business that employs over 700 professional designers worldwide who can ...
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 ...
Raj Bhaskar is a successful two-time practical software founder with one exit. In 2000, he started his first software company, VisualHOMES, to provide comprehensive financial management software to public housing agencies. With no outside ...
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 ...
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 ...
Guy Rubin is the co-founder and CEO of Ebsta, a revenue intelligence platform that works with Salesforce and Hubspot to automatically analyze existing data to improve sales performance. Started in London in 2012, Ebsta found success in the ...
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 ...
Landon Taylor created two successful digital marketing services businesses before embarking on a product-powered business with recurring revenues. His first agency drove traffic to its customers, which led to his second business, Best Company, ...
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 ...
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 ...
Charlie Alsmiller is the founder and CEO of APIWORX, a powerful integration platform for mid-sized ecommerce companies. Charlie is an experienced, practical founder who has created and grown several software companies. His first venture was ...
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 ...
Jeromy Wilson spent over ten years in the software business as a product management leader working for PE-owned and VC-funded software companies. When he decided to start his own software company, he focused on serving public libraries, like ...
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 ...
Justin Hewett started in the software business as a territory sales manager for an education software company in Utah. The company grew and Justin eventually led the sales team as the senior executive. When the company was acquired by PE ...
Morgan Katz is the founder and CEO of Ticketnology. Morgan was an enthusiastic athlete with a degree in sports management who started her career in ticket sales for sports teams and front-line venue management. Morgan saw how companies with ...
Stephanie Betters was a practicing Nurse Practitioner in heart surgery and an active real estate investor when her frustration with disparate real estate CRM and marketing solutions hit a boiling point. Salesforce and a development partner ...
Shameem Hameed created several companies, including a medical billing services company, before starting ZH Healthcare in 2008 to provide billing and EHR software to innovative healthcare providers. Their BlueBriX software grew into a ...
Hamed Mazrouei owned a security monitoring business and other businesses for many years before he started his first software and services business called Vivant Corporation. Vivant provides a complete turnkey connectivity and managed network ...
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 ...
Miles Schwartz a cofounder of Zūm Rails, a fast-growing fintech based in Canada with a growing worldwide presence. In just 3.5 years and without any outside funding, Zūm Rails has grown from a focused startup to a credible open banking and ...
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 ...
Raution Jaiswal grew up in India and then worked in management roles at large companies in the US before he discovered a problem experienced by small insurance agencies. He validated the problem, built an early solution, and didn't quit his ...
Kelly Mann was a CPA and auditor for 15 years before leaving her employer to start her own CPA firm focused on 401K benefits audits. She discovered a need to automate this process, validated the market with other CPAs, and created the first ...
Bryan Clayton is the co-founder and CEO of GreenPal, a leading on-demand marketplace of lawn care services for homeowners across the US. With a team of 25 remote employees, they help 300,000 homeowners connect with 35,000 landscape service ...
Ryan Goodman joined the startup in the early days of the business intelligence and analytics market in 2003 as a specialist helping large customers adopt this new technology. This startup was acquired by the successful BI company Business ...
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 ...
Jordan Fleming grew up in Toronto and New York, then lived in Edinburgh, Scotland for 15 years where he created a successful consultancy helping larger businesses automate and improve their processes. His experience developing workflow apps ...
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 ...
Beth Sanders was selling computer software and equipment for a regional computer retailer in Ohio when she recorded her grandmother's life stories on a tape recorder. It was so powerful she decided to create a website in 2001 that allowed ...
Josh Haynam grew up in the Central Valley of California just 100 miles from the tech center of Silicon Valley without any awareness of tech jobs or tech businesses when he lived there. He was a successful high school entrepreneur who supported ...
Esben Friis-Jensen was a technology professional in Copenhagen, Denmark before he and three Danish friends moved to San Francisco in 2013 to start a new startup called Cobalt. Cobalt.io grew steadily and raised several rounds of VC funding to ...
Massimo Arrigoni grew up in Milan, Italy, and moved to California 27 years ago to create software products and start a family, eventually moving to the San Francisco area in Silicon Valley. While leading product at the software company MailUp, ...
Windermere Real Estate is a large and well-known residential real estate broker in the Seattle area. In the late 1990s, they invested to build an internal software system to power their own business and differentiate their services. After using ...
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 ...
Deb Muller was an experienced HR executive at a large global company who left her job to start a consultancy specializing in managing important employee incident investigations. Surprisingly, her customers asked her for a software solution that ...
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 ...
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 features and customer ...
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 project helped her find a problem ...
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 goals, making short-term plans, and ...
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, he discovered a huge need for ...
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 ...
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 ...
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, onboard, and ...
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.
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 company is growing steadily with 45 remote employees. And Brad is learning fast to be a capable CEO of a larger SaaS software company.
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 ...
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 smaller trucking fleets with simple ...
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 1990s in ...
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 ...
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, ...
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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