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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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, … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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. … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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, … Listen to this episode
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 … Listen to this episode
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 … 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 … 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 … 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." … 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 … 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. … 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 … 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 … 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 … 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 … 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, … 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 … 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 … 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 … 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 … 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 … 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 … 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 … 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 … Listen to this episode
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