RS361: Lessons Learned Selling A Business

Selling a business isn't just about timing the market. It's about knowing yourself.

In this episode of Rogue Startups, Craig Hewitt sits down with Colin Gray, founder of Alitu and The Podcast Host, to discuss what it's really like to sell a SaaS company after 15 years. Colin shares why he decided to exit, how founders should think about timing a sale, the emotional side of letting go of a business, and why "stair-stepping" through multiple businesses may be a smarter path than chasing a single life-changing exit. They also explore how AI is reshaping SaaS, content marketing, and YouTube, as well as what comes next after selling a company you've spent years building.

Whether you're thinking about selling a business someday or simply trying to build one that lasts, this conversation is packed with honest advice from two experienced bootstrapped founders.

Highlights from Craig and Colin’s conversation:

• How to know when it's time to sell your business
• The stair-step approach to building wealth
• Founder burnout and losing passion for your company
• The realities of SaaS valuations today
• Why building an audience before software matters
• AI's impact on SaaS and content marketing
• Why YouTube is still one of the best marketing platforms
• Life after selling a startup
• Bootstrapping vs. venture-backed growth
• Lessons from two experienced SaaS founders

Resources and Links from This Episode

• The Podcast Host: https://www.thepodcasthost.com/ 
• Colin on LinkedIn: linkedin.com/in/colinmcgray?originalSubdomain=uk 
• Castos Free Tools: castos.com/tools
• Email me: podcast@roguestartups.com
• Find me on Twitter: @TheCraigHewitt 
• Twitter: @TheCraigHewitt 
• LinkedIn: Craig Hewitt 
• Email: podcast@roguestartups.com

Chapters

• (00:00:00) - How to Get Out of Debt in Retirement
• (00:01:33) - A Chat With Colin on Rogue Startups
• (00:02:54) - When Should You Sell Your Business?
• (00:09:18) - Ideas for Buying or Selling Our Company
• (00:14:57) - Allevi On Falling Out Of Love With the Business
• (00:16:56) - How to Balance Working and Living
• (00:21:12) - Getting a Job in the Age of AI
• (00:23:01) - Ex-CEO on His Exit
• (00:27:08) - Podcasting: The SaaS Jobs Apocalypse
• (00:29:23) - SaaS and Content: The Future of Both
• (00:36:43) - How to Keep Your YouTube Channel Updated
• (00:39:47) - Under Threat: Podcasts and Video
• (00:41:21) - Alitu Expands Into Paid Acquisitions
• (00:43:26) - Exclusives: Colin's Exit
• (00:44:29) - Co-Hosting: Solo or Team?