#125: Created the World’s Largest Subscription Service for Creative Design – Russ Perry

by shawn | Jan 2, 2025

 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 deliver design projects in...

#119: Growing His Third Side Gig SaaS Venture After Selling His First Two – Troy Munson

by shawn | Nov 21, 2024

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 launching his second side...

#117: Bootstrapped to 9 Figure Exit in Online Education for Real Estate – Michael McAllister

by shawn | Nov 7, 2024

 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 training materials from a...

#116: The Do’s and Don’ts of Succeeding with Offshore Software Development – Matt Watson

by shawn | Oct 31, 2024

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 efficiently. His top...

#111: Bootstrapped Then Raised VC Funding Before Selling to Salesforce for $250 Million

by shawn | Sep 20, 2024

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 with their customer...