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


Wayne Cartmel is the founder and CEO of MyNewTerm, a specialized hiring marketplace and applicant tracking system that connects schools across England directly with job seekers. It allows educational employers to post vacancies ...


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 ...


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 ...


Blakely Graham co-founded TaskRay, a project management and customer onboarding platform built inside the Salesforce ecosystem. After years working with Salesforce implementations and operations teams, she and ...


Andy Alsop didn’t start The Receptionist—he bought a small iPad-based visitor management app in 2013 for $250K and turned it into a real SaaS business. What began as a simple front-desk check-in tool evolved into a ...


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 ...


Chad Ingram is the founder of Distro, an AI recruiting software company that helps mid-market and enterprise companies automate candidate screening, vetting, ranking, and scheduling. He previously built Jump, a ...


Vivek Bhaskaran is the founder and CEO of QuestionPro, a bootstrapped survey and customer-experience research software platform that they have been building for more than 25 years. Based in the Bay Area, Vivek has grown ...


Keith Shields is co-founder and CEO of Designli, a custom software development company that's helped non-technical founders build over 200 digital products in 13 years. After struggling to build apps through unreliable ...


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 ...


Jordon Comstock is founder and CEO of BoomCloud, a vertical SaaS company serving dental practices with patient membership software. He started the company scrappy and bootstrapped, with no outside funding, after years in ...


Robin Eissler is the founder and CEO of BoosterHub, a vertical SaaS platform built for high school booster clubs. After selling her prior business as a private jet broker, Robin volunteered to run a local booster club ...


Josh Ho is the Founder and CEO of Referral Rock, a bootstrapped referral marketing platform serving SMBs that rely on multi-step, relationship-driven sales. Starting in 2015 as a solo developer consulting on the side, Josh ...


Shailesh Hegde is the CEO of Hubilo, a Bangalore-based webinar software company that initially started during COVID as virtual events tech and raised $150M in VC funding before the market shifted. Originally joining as head ...


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 ...


Yuval Selik is co-founder and CEO of Promomash, a software platform and managed service for Consumer Packaged Goods (CPG) brands to manage their trade promotions and field marketing activities. Yuval is a former CPG founder who ...


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 ...


Jesse Burrell is the CEO and co-founder of BatchService, now known as BatchData, a real-time data and API platform designed for prop-tech startups and enterprises requiring massive and current housing data. Jesse was a real estate ...


Chris Brisson is the CEO and co-founder of Salesmsg, a conversational two-way texting platform that enables businesses to engage with their customers through opt-in SMS. When his first software company stalled, he shut it down and ...

Tracy Larson is President and CEO of WeSuite, a vertical sales automation platform designed for larger integrators who sell complete security systems for commercial and residential real estate. Tracy and the cofounders were in the ...


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 ...


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 ...


Seth Hassell and Clint Ethington are the co-founders of Genius Monkey, a programmatic ad tech platform with proven targeting, tracking, and attribution for optimized results. Seth and Clint were childhood friends who worked on many ...


Brian Dosal was the founder and CEO of BrightGauge, a software company he bootstrapped and grew to almost $10M ARR with his brother before successfully selling the company in 2019. BrightGauge was a business analytics and dashboard ...
Howard Gottlieb started Read-A-Thon in 2012 as a reading-based fundraising platform that helped students raise money while boosting education. Their easy platform and simple fundraising approach created amazing results. The Read-a-Thon business ...
Scott Desgrosseilliers is the founder and CEO of Wicked Reports, a leading multi-touch marketing attribution software for SMBs who use paid online advertising. Scott is a data and analytics expert who saw the costly limitations of simple ...
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 ...
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 ...

Michael McAllister is the founder and former CEO of The CE Shop, the leading provider of pre-licensing and continuing education for real estate professionals in the U.S. Michael started The CE Shop in 2005 by distributing existing ...
Last year I interviewed three-time software founder Matt Watson on this podcast about his successful practical founder journeys. Matt leveraged offshore software development talent in his last two SaaS companies to staff up quickly and grow ...
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 ...
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, ...
Erin Fletter had a long career in the restaurant business before starting an after-school enrichment program to teach kids how to cook at her daughters' school in 2011. Her cooking program became popular, and she improved and expanded it to ...
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 business and wondered why it took $10,000 and nearly a month to ...
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 companies. His first venture was ...
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 ...
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 an online marketplace.
Nathan ...
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, enabling them to connect with content ...
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 London that raised funding from big VCs and Amazon. It grew ...
Raj Khera is an experienced practical SaaS founder who has used search engine optimization (SEO) to grow businesses very efficiently. Now he coaches entrepreneurs at MoreBusiness on how to use organic SEO as a core part of their marketing ...
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 point. Salesforce and a development partner ...
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 ...
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 access new contracts up for bid by the US government. Their ...
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 help 300,000 homeowners connect with 35,000 landscape service ...
Wissam Tabbara is a serial entrepreneur who has created multiple software startups in Seattle since 2009 when he left Microsoft where he was a software development manager. He led multiple startup technology teams and now is an experienced CEO ...
Lloyed Lobo is the co-founder and former president of Boast.ai, a leading platform to help software companies in the US and Canada redeem available government tax credits. Technology-powered Boast.ai was launched in 2017 after starting a ...
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 was acquired by the successful BI company Business ...
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 processes. His experience developing workflow apps ...
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 ...
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 monthly fees while they ran their services business ...
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 ...
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 ...
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 ...
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. He experimented with many business ...
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 simple software solution to track, onboard, and ...
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 ...
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, ...
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 ...
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 ...
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 ...
