Every week, host Greg Head interviews a successful software founder who started, grew, and sometimes sold a valuable software company—without VC funding.


Shawn Boyer is founder and CEO of goHappy, a frontline employee communication and engagement platform for companies with a thousand or more hourly workers in restaurants, logistics, manufacturing, and retail. Before that he ...


Steve Wolfe co-founded Growth Street Partners in San Francisco about ten years ago with his partner Nate Grossman, after a career in software-focused private equity. The firm's name is the point: they don't invest on Sand ...


Lynn Burghardt is a fifth-generation owner of Burghardt Sporting Goods — the oldest family-owned sporting goods store in the country, founded in 1881. Chipply grew out of that business: after years of hacking together their own ...


Jay Maharaj built TeamLinkt in Saskatoon, Saskatchewan, a place not known for software. He saw the problem while coaching his own kids: the hockey team had a budget for a team communication app, and the soccer team didn't, so ...


Ajay Gupta founded Stirista in San Antonio after helping with micro-targeting a presidential campaign. His first product identified people who spoke a second language for multicultural marketing — built from scanned baby-name ...


Vic Levitin is a serial founder who built companies in Israel for two decades before fleeing the war with his young family to the island of Koh Samui, Thailand. His first SaaS company, CrazyLister, grew out of his own ...


Steve Oriola isn't the founder of Unbounce — he's the CEO that Crest Rock Partners brought in to run and transform it. A sales-and-marketing software veteran who spent a decade at Constant Contact, and even ran Act! for a spell ...


Eran Galperin is a Brazilian jiu-jitsu black belt who had already had one VC-backed marketplace failure when he started Gymdesk. Originally called Martial Arts on Rails, it launched in 2016 as a naive version of what he thought a ...


Cliff Sentell co-founded Compass Professional Health Services in Dallas in 2005, where he and two partners each put in $20,000 and bought a single server. They started in healthcare price transparency, reverse-engineering the cost ...


Matthew Bullis grew up in a mud-brick hut with no running water on a small island off South Korea and was adopted to the US at 11, speaking no English. After going to college, he created a dot-com startup, then he took over his ...


Paul Hoeper founded InvoiceASAP after spotting a simple but painful problem in 2009: home service businesses couldn’t easily create invoices or collect payments from the field using mobile devices. He started in New Orleans, launched ...


Jerry Alderman is the co-founder and CEO of Valkre Solutions, a SaaS platform built specifically for key account managers (KAMs) who oversee the largest and most strategic customers in global B2B companies. After careers in ...


Rupert Mayer is the founder of IPfolio, a vertical SaaS platform built for corporate intellectual property teams to manage patents, trademarks, renewals, and innovation workflows. Originally from Austria, ...


Marc Sanderson is the founder and CEO of INNERGY, but he didn’t start as a software founder. After earning his MBA and searching for a company to buy, he and partner Walter Wilkie acquired a small architectural ...


Perry Rosenbloom, founder of LaunchBay, previously built and sold Brighter Vision before starting his second SaaS company focused on onboarding. After running hundreds of onboarding processes per month, he saw ...


Dinakara Nagalla built EmpowerMX over more than a decade to digitize aircraft maintenance for major airlines like American, Southwest, and United. Starting from deep domain experience inside aviation IT, he tackled ...


Joseph Lee is the co-founder and CEO of Supademo, a fast-growing SaaS company solving a common pain: quickly creating new product demos. In just two and a half years, they built a modern, AI-powered solution that ...


Simon Swords founded Fundipedia after starting in a backyard shed, building bespoke software. Originally a custom development shop, his firm built a data governance platform for major buy-side asset managers ...


Steve Reynolds didn’t start TripBam to disrupt the global hotel industry—he simply noticed that corporations weren’t getting the discounts they negotiated, and no one was checking. After 30 years in travel technology, ...


Will Caldwell started Snap after his first real estate software startup fizzled, pivoting from agent tools to regulated compliance data. He discovered lenders were required to buy hazard and flood certifications, and ...


Luigi Mallardo joined Woffu as an early angel investor and later became CRO, helping founder Miguel Fresneda shape a practical SaaS growth path. Based in Barcelona, Spain, Woffu has built a modern cloud-based time and ...


Natalie Barbu is the founder and CEO of Rella, a SaaS platform built to streamline collaboration and workflows for social media teams and agencies. She began as a YouTube creator, grew a following of over 300,000, and then ...


Alan Miegel is co-founder and CEO of BetterComp, a modern compensation management platform for larger companies to manage compensation datasets to set market-priced salary benchmarks. Alan and his cofounders started the company ...


Zvi Band is co-founder and former CEO of Contactually, which was CRM software for real estate and other relationship-oriented professionals. Contactually was founded in 2011 with initial funding and support from 500 Startups in ...

Josh Turley is the CEO of RTA Fleet Management, a fleet management software company that his grandfather founded in the 1980s and operated as a small family business for decades. Then Josh’s father ran the business until 2015, never ...


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 ...


Roy van den Broek is the founder and CEO of Rentman, a rental business management software platform for event and media production companies. Roy built software for his event equipment rental business in the Netherlands. He ...


Sean Hoban was co-founder and former CEO of Kimble Applications, a leading professional services automation (PSA) software for organizations to manage their professional services business's entire operational and financial ...
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 ...
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 ...
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 ...
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 ...
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 ...
