Aaron Steffey is the co-founder and co-CEO of Propeller, an online platform that enables insurance agents and brokers to issue surety bonds instantly — without the lengthy paperwork or back-and-forth typically involved in ...
Practical Founders Podcast with Greg Head
Every week, host Greg Head interviews a successful software founder who started, grew, and sometimes sold a valuable software company—without big funding.
Over $9 billion in founder equity value has been created by over 100 SaaS founders interviewed on this podcast so far. That’s an average of $75 million of founder equity value created by each company.
Some Outside Funding
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 ...
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 ...
Paul Van Metre was the co-founder of a successful machine shop that manufactured custom parts for the aerospace and medical device industries. Over 15 years, they created and improved software to run their entire business, which created huge ...
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 ...
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 ...
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 ...
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 ...
Robin Alex worked in a digital marketing agency in Dallas when he discovered their small business clients struggled to nurture and follow up with their website leads. In 2018, Robin and two developers prototyped a marketing automation and CRM ...
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 ...
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 ...
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 ...
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 ...
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 ...
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.
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 ...
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 ...
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 ...
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