Tomorrow’s Fortune

Welcome to the action-packed newsletter designed to help you navigate the world of business and investing. If you missed last week’s post, check it out here. 😎 

Today’s Digest: 

• Why is everything on Pen and Paper? This is a real question I asked a elevator maintenance business. So.. I submitted an offer… but hear my reason why

• Groundswell Law: My go-to legal partner for all of my deals. Details below

• What’s Happening in the Markets? Chinese Tech Stocks Make a Comeback, Starbucks Job Cuts, CarMax’s Earnings Fumble and NVIDIA’s $100B deal

• Deal Review We found a cash flowing Low Voltage Cable Installation business in Washington ($352K of Cash Flow). Click HERE for the listing

• 🚨NEW COMMUNITY🚨: We are launching “The Deal Team” a private community for business buyers and owners. Will include monthly calls, deal reviews, and all the resources you need to find, grow and buy businesses. Respond to this email with “interested” if you’d like to apply to join (if you haven’t expressed interest already). There’s already a ton of you lined up and we’re excited to kick off in a few weeks - STAY TUNED!

TOP STORY

Embrace the Messy…

Most buyers run from “messy” businesses.

And honestly — 90% of the time, that’s the right call.
If a company is drowning in disorganization, running off pen-and-paper systems, missing financials, or bleeding cash, it’s usually a headache with no upside.

But here’s the nuance: that last 10% of “messy” deals is where fortunes are made.

Why Messy Can Mean Money

When a business looks chaotic, sellers often price it at a steep discount. Multiples compress when buyers see risk. That creates the gap:

• Clean, organized business: Sells for 4–6× EBITDA.

• Messy, disorganized business: Can often be acquired for 2–3×, sometimes less.

That delta is your return. You’re not just buying cash flow — you’re buying the opportunity to professionalize and re-rate the multiple.

The Tactical Playbook