Every one of these was bought while I had a corporate job.
Booz Allen, Cisco, Lucent, VMware — and, on the side, a business each time. Most people make one bold move in a career. This is what five looks like.
You're in the window.
The hard part isn't leaving. It's the eighteen months before — knowing you need something different and not being able to say what.
- Director-level or above, fifteen-plus years in, most often in technology or a large corporate
- Something has moved — a restructure, a severance offer, a vesting date, a business someone put in front of you, or you've simply decided
- Capital you could put to work, and a household that needs the decision defended
- A business you're looking at right now, and a feeling you can't name about it
A decision, with the numbers behind it.
- Stay and renegotiate, buy, start, or wait — priced against each other, honestly
- What you can actually risk, what a business would actually pay you, and how to finance it with or without an SBA loan
- How to read a broker package, what the seller and the lender want you to miss, and when to walk
- A plan you can explain to your spouse and your banker in the same sentence
Two ways in. Both start with your numbers.
Decision Day $2,500
A half-day, one-to-one, on video or in Richmond. Your situation, your capital, your risk capacity, and the paths in front of you — priced against each other.
You leave with: a written decision architecture and your next 30 days. Credited in full toward the program if you enroll within 30 days.
Book a Decision DayOwnership Decision Program $7,000/mo · 3 months
Ninety days, weekly calls, direct access between them. Clarity on your numbers; three paths priced; the diligence war room — broker packages, seller and lender incentives, financing without betting the house; the decision, with your spouse in the room; then your 90-day search or launch plan.
You leave with: a decision, a one-page ownership thesis, and a deal-screening scorecard you'll use on every business you look at.
A free, live hour every month. Open questions on leaving corporate and buying a business. You don't have to say a word — you can just listen. Registering for the Checklist above gets you the invitation.
Twelve questions that make a bad deal show itself before you sign. Free. Take it to your own attorney and CPA — not the ones the seller recommends.
Someday May Never Come for leadership offsites and client events; $1.55M Tuition for career-transition and outplacement programs. Live, with the room involved. Ask about dates.
I've bought five small businesses — a deli, a party-rental company, a garage door company, a sandwich franchise, and a federal contractor — and I bought most of them while holding a full-time corporate job, rising to Director at VMware before Broadcom restructured the company.
One of those deals cost me $1.55 million. The seller, the banker, and the broker were friends; I was the mark. My house went into foreclosure. I rebuilt from there: a profitable exit, a 2x exit, and two companies I run today, both GSA-listed and SDVOSB-certified.
Now I work with corporate leaders who are deciding whether to leave — and whether to own something instead. Not whether you're crazy. Whether you're ready, what you can afford to risk, and how to buy without betting your house. I've made that decision five times, including once badly, and I'll tell you what the MBA didn't.
Navy veteran. Richmond, Virginia. Speaker for the Virginia SBDC, James Madison University, and APEX Accelerators.
Straight answers.
Is this coaching?
No. It's a decision, made with the numbers in front of you and someone who has made it five times. You'll do real work on real financials. If you want someone to help you find your purpose, there are good people for that; I'm not one of them.
I don't have a business in front of me yet. Is it too early?
It's the best time. The most expensive mistakes are made before the search starts — deciding what you can risk, what you need the business to pay you, and what you'll walk away from. A Decision Day before you look at a single listing saves months.
Do you take fees from brokers, lenders, or sellers?
No. Not on your deal, ever. My clients pay me, which is why what I tell you about a listing is worth anything. Where a client's search overlaps with a business I own or am acquiring, I say so in writing before we go further.
Can't I just do this with an SBA loan and a broker?
You can, and many people do it well. I did it with a bank loan and a broker in 2007 and lost $1.55 million. The point isn't that the tools are bad. It's that nobody in that transaction works for you.
I'm a veteran.
So am I — Navy. Ask me about the program; I keep room for veterans who are serious about ownership.