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


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 ...


Sharon Nouh built ProSpend, a spend management SaaS platform for mid-market companies, after seeing firsthand how broken expense processes were in corporate travel. Starting with an expense tool, focused on her home ...


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 ...


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 ...


Raju Patel founded eShow over 25 years ago after building a speaker portal for a magazine company and realizing he had a repeatable software product. What began as a one-man shop in suburban Chicago evolved into a robust ...


Darryl Pahl is the co-founder of DFnet, a Seattle-based company providing clinical trial data management software and services. Along with his wife and co-founder, Lisa Ondrejcek, Darryl started the company more than 20 years ...


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 ...


Brian Forbis is the CEO and President of Blood Bank Computer Systems, Inc. (BBCS), a business his mother created in the 1980s to serve the non-profit blood bank industry in the U.S. Brian started in sales, then transitioned to run ...


Henry Valentino is the founder and CEO of EConnect, a leading provider of facial recognition software for casinos and stadiums, ensuring venue security and compliance. He founded EConnect in 2009 and pivoted several times before ...

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 ...


Chris Erler was co-founder and COO of ComX, a sales pipeline generation for mid-market B2B companies in Germany and Europe. Chris and two other founders started the company in 2018 to conduct turnkey modern digital marketing and ...


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 ...


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 ...
Richard Change is co-founder and CEO of PFA Solutions, the provider of FirmView software. FirmView® is the leading carry and compensation management platform for private equity investors to manage their internal compensation from fees and ...

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 ...
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, ...
Mike Trasatti spent 10 years in the automotive dealer software business before he found an auto dealer in Iowa who had built is own complete software system. They partnered up in 2008, and Mike became the first CEO of the spinout software ...
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 ...
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 ...
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 ...
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 ...
Harry Hopkins is co-founder and CIO of Viewgol, a medical billing technology software and services company based in Dallas, Texas. Viewgol was started in 2017 by three founders who got the product and revenues going before hiring additional ...
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 ...
Subramanyam Kasibhat has created dozens of products in many different industries. He and his wife were contracted by a friend to build a software solution for a manufacturing plant for a German company. Seven years after they started with their ...
Miles Schwartz a cofounder of ZÅ«m Rails, a fast-growing fintech based in Canada with a growing worldwide presence. In just 3.5 years and without any outside funding, ZÅ«m 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 ...
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 ...
Praveen Ghanta graduated from MIT with degrees in computer science and economics and worked for various financial services companies after trying his hand at a software startup. Working in his spare time, he built a product and recruited a ...
Oliver Low worked for Microsoft and then MySpace in London before creating a successful digital agency in 2010 with two friends. Their agency grew fast and was profitable, so they invested in building software apps to solve problems that they ...
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 ...
Gregory Shepard is a serial entrepreneur who has created and sold 12 companies, including marketing software and ad technology companies. In 2016, he sold two of his bootstrapped software companies, AffiliateTraction and AdAssured to eBay for ...
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 ...
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 ...
"My B2B SaaS startup needs just more warm leads. But we have struggled when we hire junior salespeople to call on and email cold prospects to generate qualified leads that the CEO or salespeople can close."
This is a common frustration for ...
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 ...
Gopal Krishnamurthy was an early BI and data analytics expert working for a large company when he left to start a BI consulting company called Visual BI in 2010. Visual BI grew to over 300 employees serving enterprise customers as an evangelist ...
Matt Watson was a two-time software company with two successful exits before he was 40 years old. He started his first company, VinSolutions, in his basement in Kansas City in 2006. VinSolutions started by helping auto dealers upload photos of ...
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 ...
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 ...
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 ...
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 ...
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.

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 ...
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 ...
