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: 

• Essential Diligence Questions: I ask business owners these three questions for every single deal. Helps me build conviction and more importantly, save time

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

• What’s Happening in the Markets? Winter Heating Bills on the Rise, New Pope Speaks on CEO Pay, Spirit Airlines Job Cuts and NVIDIA’s Intel Investment

• Deal Review We found a cash flowing Biohazard Cleanup & Restoration business in Georgia ($275K 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

3 Questions to Ask When Buying a Business…

Most first-time buyers obsess over financials — SDE, EBITDA, multiples.
But in private equity, the best operators know the real insights come from the questions you ask the seller directly.

Here are three questions that separate pros from amateurs when evaluating a deal:

1. What’s your true value proposition — and why do customers pick you over competitors?

This gets at the company’s moat. Are customers loyal because of pricing, service, proprietary know-how, or simply because they’ve “always used you”?

Why it matters:
If the business is competing on price alone, margins are at risk. If it’s competing on service, brand, or relationships, those are stickier and harder for competitors to replicate.

Investor Takeaway: The strongest businesses aren’t just profitable — they’re defensible.

2. Where have you wanted to invest, but haven’t had the time or resources?

This reveals the “hidden upside.” Owners often leave growth opportunities untouched — new geographies, product lines, digital marketing, hiring a sales team — because they’ve been focused on day-to-day survival.

Why it matters: