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
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