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


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 ...


Dan MacDonald is the founder and CEO of BIS Safety Software, based in Edmonton, Canada. He didn’t start in safety or software—he came from retail and leadership training before an unexpected pivot led him into online ...


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 ...


Vince Mayfield is cofounder and CEO of TalkingParents, a co-parenting app for communication and coordination used by divorced parents raising children. Cofounder Stephen Nixon was a lawyer with family cases who recognized the need ...


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 ...

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 ...
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 2007 to create a ...
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 ...
Morgan Katz is the founder and CEO of Ticketnology. Morgan was an enthusiastic athlete with a degree in sports management who started her career in ticket sales for sports teams and front-line venue management. Morgan saw how companies with ...
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 ...
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 ...
