Shoot the Moon with Revenue Rocket

Tell Tale Signs it is Time for an Exit

Episode Summary

Founders rarely get a flashing “SELL NOW” sign. In this conversation, Mike, Ryan, and Matt unpack the practical signals that it may be time to explore an exit or merger. From wearing too many hats and stalled scale to outside capital needs, shifting life priorities, and external market pressures (hello, AI), they show how to separate simple fatigue from being truly “done.” You’ll hear why timing the company’s health matters more than timing the market, and how to think about purpose—and a plan—on the other side of a deal.

Episode Notes

Episode 235: What we cover

• Personal vs. company readiness: passion, energy, and risk appetite
• Scale ceilings: when you need more talent, capital, or partners
• “Wearing every hat”: the founder role that’s become unsustainable
• Market timing vs. company health (multiples vs. demand)
• External shifts (e.g., AI) that change the calculus
• Tired vs. done: tests to gain clarity (distance, peers, spouse)
• Life after close: purpose > plan, and why that matters
• Age, seasons, and the cost of waiting too long

RELATED EPISODES:

Episode 234: Deal Urgency in Q4: How to Close (or not close) Before Year-End. Listen now >>

Seller Readiness: What To Do When a Buyer Comes Knocking. Listen now >>