Hard Lessons in Early Sales: How Collin Stewart Found Real Product-Market Fit (Ep182)

Oct 28, 2025 | Sales Talk for CEOs Podcast

From hockey stick growth to flat on your face, it hurts and Collin Stewart, CEO of Predictable Revenue, can tell you firsthand. He had one customer before he left his full-time job, the problem was he still had one customer 18 months later. In his first endeavor this entrepreneur built what he thought everyone needed and kept showing them and expecting them to say how great it was, but they didn’t. “I was building my idea. I wasn’t building what the customer’s wanted.”

The lesson, it’s all about the customer, what they need and want.

Collin tried and failed more than once realizing he wasn’t going fast enough in one of his businesses even though he grew from zero to 1 million in 3 months. The business plateaued and in the end just closed it down.

This led to a pivot that Collin calls the “one of his dumbest.”

In retrospect for the SDR business, he realizes that they were trying to run off a 15 year old playbook that Aaron Ross, his former partner made work at Salesforce in the early 2000s. 

We all make mistakes but listen to find out how Collin recovered and what he is doing now. 

Key Takeaways for CEOs and Founders

  • Listen to your customers.
  • Build it fast.
  • Update  your playbook.
  • Don’t do it if you don’t love it.

Watch below or on our YouTube channel

 

Rapid-Fire Mentions

  • Book: Good Strategy, Bad Strategy by Richard Rumell
  • Podcast: Acquired FM
  • Advice to CEOs:  Lead with relationships and real value. Outbound still works, but only if your product-market fit is strong. If you’re early-stage, skip the pitch and focus on helping first.

 

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