The deal that left millions behind

Founders often approach exit prep like a sprint to the finish. But in reality, it’s a long game of strategic positioning, clarity, and clean structure.

The real blockers aren’t just operations; they’re how you present and protect your value before a buyer ever steps into the room.

On one of the early episodes of Two Commas, I had a great conversation with Tom Price - a founder who exited at just 27 with a $12M deal. On paper, it was an incredible outcome. But beneath the surface, there was an even bigger story.

Tom was running two businesses: his service company, EES, and a promising software product, HVAC Hero. When the acquisition offer came through, both were bundled into a single deal.

HVAC Hero wasn’t properly structured or valued as part of the negotiation.

The deal was effectively priced on the service business multiple (undisclosed, but ‘average’) and the software product got swept in without commanding its own premium. Not long after, the acquirer flipped the combined entity at a 10x multiple.

Tom got paid fairly for one business.

The buyer walked away with two and a huge win.

What to do instead:

• Separating assets early
  If it has its own IP, brand, or commercial model it deserves its own legal and financial wrapper.

• Reducing technical debt
  HBR calls it the silent killer of growth. If your ops rely on bespoke code or founder-held knowledge, buyers will either back away or discount hard.

• Buying over building
  Deloitte found that companies who “buy over build” for non-core systems scale 2.4x faster.

• Creating exit-ready ops
  Bain & Co says cleanly structured businesses with defined systems and roles command up to 30% higher valuations.

You don’t have to sell next quarter.

But building with exit in mind gives you leverage, optionality AND a far better outcome when the time comes.

Want to explore how your structure stacks up?

Book a strategy call with me here.

Cheers,

Josh

P.S. If you’ve got a product or IP hiding inside your main business, now’s the time to structure it properly. The Two Commas episode with Tom Price is a cautionary tale worth hearing.

P.P.S. I’m about to launch a new workshop designed to help founders understand exits at a practical and strategic level. It’s loaded with insight and has received excellent feedback to an early audience. If you want first access when the invitation drops, let me know by replying to this email.

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