Shiver Showcase - The Quiet Exit King

Jeffrey Redmon | Sep 15 2025 17:00

You’ve probably never heard of Dave H. — and that’s exactly how he prefers it.

No headlines.
No LinkedIn swagger.
No bestseller book tour.

Just a quiet track record of building real businesses, scaling smart, and exiting well — three times and counting.

A Pattern of Purposeful Wins

  • IT Services Startup — Started in his basement, bootstrapped, and sold at 7x EBITDA to a regional MSP after locking in recurring contracts and tight margins.
  • SaaS for Field Contractors — Solved a scheduling pain point in the trades. Grew to $10M ARR in 4 years. Sold to a strategic acquirer expanding market reach.
  • Specialty Equipment Rentals — Bought distressed assets during COVID, turned it into a cash-flow machine, and rolled it into a PE-backed platform last year.

 

What We Can Learn from Dave H.

  • Build to Exit — even if you never sell. Systems, clean books, and culture matter.
  • Solve Real Pain — he never led with a product, only a bleeding problem.
  • Stay in the Shadows — his focus was solutions, not spotlight.
  • Know Your Number — he always knew when enough was enough.

“Build it like someone’s watching — because eventually, they will.”

Shark Sense Reflection

In a world obsessed with the loudest voice in the room, it’s worth remembering:

The shark that bites hardest is often the one you never see coming.

Dave H. is imaginary — but there are thousands of “quiet exit kings” out there: building steadily, leading humbly, exiting strategically.

Question: Are you building a business someone would want to buy — even if you’re not selling?