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 one. He and his childhood friend Rock Felder started working on their product and startup idea while they still had full-time jobs, with Zach as the CEO and CTO. Now Squadcast is one of the leading podcast recording studio platforms used by tens of thousands...
Oct 21, 2022•52 min•Season 1Ep. 18
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. After several years of experiments and hard startup lessons learned, Echosec finally shifted from being an inexpensive news/insights tool to a comprehensive threat intelligence platform ...
Oct 14, 2022•50 min•Season 1Ep. 17
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. Brad's deep experience with e-commerce advertising data and conversation tracking analytics helped him find a problem to solve. He and his cofou...
Oct 07, 2022•50 min•Season 1Ep. 16
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 new car online. He grew the company for 5 years—without VC funding—and sold it to a giant Fortune 500 company in 2020. Daniel quit his job in 2015 to build Carvoy's first product using developers in Ukraine. It allowed consumers to choose a new car online and ...
Sep 30, 2022•50 min•Season 1Ep. 15
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 in her next startup and what was really "non-negotiable" in her life. Now she's a nomadic world traveler and the founder of a growing software business. Melissa started Spacio to provide a technology solution to high-end residential real estate agents to capture visitor names electronically at open houses. It took y...
Sep 23, 2022•52 min•Season 1Ep. 14
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 technology. Seth was the founder and CEO of Crescendo, an interactive music trainer that provides real-time performance assessment feedback using acoustic pitch detection and machine learning as a mobile app. With a little angel funding, Crescendo grew to over 1M use...
Sep 16, 2022•1 hr 1 min•Season 1Ep. 13
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 which often doesn't work out well for founders in the end. Dougal's family had been investing in software companies for over 20 years through their Houston-based family office. Now Golden Section includes a founders studio for venture development, a worl...
Sep 09, 2022•55 min•Season 1Ep. 12
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 GPS-tracking fleet management software. Sean was a co-founder and COO of M2M in Motion, a self-funded software company based in the Chicago area. Sean wasn't the trucking industry expert, the crazy entrepreneur, or the visionary salesperson. He provided th...
Sep 02, 2022•51 min•Season 1Ep. 11
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 New Orleans, Louisiana before quitting his job to start one of the first insurance claims management software companies called ClickClaims. It grew slowly and profitably as a very small company for over 10 years before Thomas sought help from advisors to see ...
Aug 26, 2022•55 min•Season 1Ep. 10
Nick Santora bootstrapped Curricula for 4 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 education courses and a single-purpose learning platform for cybersecurity security awareness training. Nick had found a big hole in the cybersecurity market while working as a cybersecurity trainer in the electric utility industry. Curricula features fun and engagin...
Aug 19, 2022•1 hr 5 min•Season 1Ep. 9
Jeremy Clarke created, grew, and sold his software company in a most unusual and successful way: He grew WebMerge to $4M revenue by just himself in 6 years before hiring his first and only employee, a strategic sales rep. It's an incredible "bootstrapped unicorn" success story that ultimately was worth $100M when he sold WebMerge in 2019. WebMerge was an online service that automates document creation to automatically fill in any documents with merged data from any source. WebMerge automatically...
Aug 12, 2022•55 min•Season 1Ep. 8
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 from his first big customers—to build a new software product called Conteneo. Conteneo was enterprise collaboration software that enabled the biggest companies to engage their leaders in new ways to make much better decisions about product portfolio investme...
Aug 05, 2022•56 min•Season 1Ep. 7
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, improving, and then selling CPA accounting services firms in the Eastern U.S. Then he grew his first VC-funded tech startup, Xendoo, to innovate in the small business accounting services space. He exited Xendoo and worked with a partner to fund and create a new s...
Jul 29, 2022•45 min•Season 1Ep. 6
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 has a new startup to keep him busy. Axosoft was popular project management and bug-tracking software for developers that he bootstrapped to launch in 2002. It grew profitably for years until it met stiff competition despite active efforts to grow. Dozens o...
Jul 22, 2022•1 hr 3 min•Season 1Ep. 5
Dan Jaffe is the founder and CEO of LawLytics, a popular 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 in 2012. LawLytics was acquired by the Australia-based Smokeball-LEAP-InfoTrack Group in 2021. Dan is still growing LawLytics as its leader of the acquired company. LawLytics is a website platform for small law firms who want a successful website but don’t wa...
Jul 15, 2022•1 hr•Ep. 4
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 and was a pioneer in shipping technology for small businesses. ShipRush is now a comprehensive shipping platform for small ecommerce providers so they can easily process shipment orders and carrier labels for USPS, Fedex, and UPS. ShipRush integrates with...
Jul 08, 2022•1 hr 3 min•Ep. 3
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 story of the bootstrap founding of Kajabi through getting $550M in venture capital funding in 2021. Kajabi is a leading "knowledge commerce" platform for experts and entrepreneurs to market and sell their expertise as online content. Started in 2010 to help ...
Jun 26, 2022•1 hr 6 min•Ep. 2
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 2006 to create a scrappy software business that made inexpensive photo-presenting and sharing tools for photographers. The Showit company was created when Todd took one of their two products and half the small team in 2010 to spin off Showit as an independent business. The sm...
Jun 19, 2022•1 hr•Ep. 1
