Expedition Equity

Expedition Equity Private market investing for disciplined, long-term investors. Education, access, and thoughtful capital allocation.

Ask most people what share of American businesses ever clear $10 million in revenue, and the guesses land around 10 or 2...
09/28/2026

Ask most people what share of American businesses ever clear $10 million in revenue, and the guesses land around 10 or 20 percent.

The real number is about 0.4 percent.

Out of more than 33 million businesses in this country, fewer than 150,000 ever cross $10 million in sales. The step before that one is almost as steep. Fewer than 1 in 20 ever reach even a single million.

Sit with that for a second. The large majority never clear one million, and eight figures is rare air.

We use the words "small business" like they describe something ordinary. They do not. Getting a company into that top fraction is brutally hard, and holding it there through downturns, key-person risk, and real competition is harder still.

Every company our operator looks to buy is a statistical outlier. A founder who made it through the stretch where most do not, built cash flow that lasts, kept customers for a decade or more, and did it in a plain industry most people walk right past.

There is always a worst-case scenario here. These are real operating businesses carrying real risk. The person who built it can leave. A cycle can turn. A competitor can press. None of that is theoretical, and I will not pretend it away.

But when a founder spends 15 or 20 years getting a business into the rare 0.4 percent and is finally ready to step back, what happens next matters. To the founder, to the people who work there, to the town that leans on it.

That is the work. Buy the survivors. Protect what made them work. Steward them for the long haul.

If you want to chat through this fund or any other offerings at Expedition Equity, DM to set up a meeting.

We keep tearing down the most affordable housing in America. Then we act surprised it costs more.Mobile home parks are t...
09/25/2026

We keep tearing down the most affordable housing in America. Then we act surprised it costs more.

Mobile home parks are the largest source of unsubsidized affordable housing in the country. Millions of families live in them. And the supply shrinks every year.

Old parks get bought, closed, and paved over for something that pays the developer more. Almost no new parks get built, because towns will not zone for them. Demand climbs. Supply falls. That gap does not close on its own.

That is the whole thesis. Not a projection. A supply-and-demand fact you can watch happening.

Here is the part I have to name. This is not a liquid asset. Your capital is committed for years. Parks need real management, real repairs, and an operator who knows the work. There is always a worst-case scenario, and a badly run park is a slow, expensive problem.

Run well, though, the demand underneath it does not depend on people feeling wealthy. It gets stronger when affordability disappears.

I hold this in the portfolio for that reason. Not because it is exciting. Because it is durable, and durability is what carries a portfolio through the years the exciting assets struggle.

Curious how others weigh durability against liquidity. Drop your comments below.

There's a generation of business owners heading for retirement with nobody to hand the keys to. That gap is a quiet prob...
09/24/2026

There's a generation of business owners heading for retirement with nobody to hand the keys to. That gap is a quiet problem for them and one of the more durable opportunities in private markets.

Here's the setup. A huge number of solid, cash-flowing small businesses are owned by people in their sixties and seventies. Sign companies, electrical contractors, well drillers, equipment servicers. The unglamorous, essential outfits that keep the physical world running. Many have no kid who wants the business and no obvious buyer. The owner is ready to slow down, and the business needs a next chapter.

That's where acquisition comes in. You buy the business at a sensible price, keep what works, professionalize the parts the founder ran off memory, and let it keep doing the essential thing it already does well. The best deals share a trait. The seller rolls some of their own money into the new ownership and stays on for a while to train their replacement. When the person who built it keeps skin in the game, it tells you something.

The worst case, and it's real. These are operating businesses, not coupons. A key person can leave, a big customer can walk, integration can go sideways. The operator running the acquisition is everything. A great business bought by the wrong team is still a bad investment.

But buying durable, essential businesses from a retiring generation, at fair prices, with the founder still invested, is a strategy with a long runway ahead of it.

If the essential-business side of private markets interests you, reach out and I'll walk through how these get underwritten.

People ask me which of these is the best investment. Energy, apartments, medical buildings, private credit, small busine...
09/23/2026

People ask me which of these is the best investment. Energy, apartments, medical buildings, private credit, small business. It's the wrong question, and it's the one almost everybody leads with.

None of them is the best. They each do a different job. Private credit and medical real estate pay you steadily and hold the floor. Small business and growth real estate build the wealth over time. Energy does a tax job almost nothing else can, at a risk you keep small. Apartments are a timing play that looks more honest now than it has in years. Mobile home parks quietly keep paying while nobody's watching.

The right questions are the ones I use. Which job does my portfolio still need filled. Which of these fits my situation and the money I can afford to tie up. And is the timing on my side or against me. Get those right and the specific asset almost picks itself.

On timing, one honest read. After a few hard years, a lot of these look more reasonable to build into now than they did at the top of the last cycle. Prices reset, supply pipelines thinned, and the euphoria that made people careless is gone. That's usually a better environment to start than a boom is, though none of it is a sure thing and all of it rewards patience and discipline.

The best investment isn't a thing. It's the right job, filled at a fair price, with money you can leave alone.

If you want a second opinion on which job your portfolio still needs filled, send me a message. I'll tell you straight, even if the answer is 'not yet.'

A dental practice will re-sign a lease for another decade rather than fight over a rent bump it might win. That reluctan...
09/22/2026

A dental practice will re-sign a lease for another decade rather than fight over a rent bump it might win. That reluctance to move is the entire investment behind medical real estate.

Think about what's inside a medical or dental office. Plumbing run for specific equipment. Imaging machines bolted in. Custom buildouts that cost six figures, and a patient base that knows the address. Moving all of that is a nightmare. So these tenants stay, and stay. On a triple net lease, they also pay the taxes, the insurance, and the upkeep, while you collect the rent.

Now layer in who the tenant is. Healthcare demand doesn't flinch with the economy. People see the dentist when a tooth hurts and the doctor when they're sick, in a boom or a recession. And the country is aging, which means more demand for care every year, not less. You're betting on people needing healthcare, which is about the safest demand bet there is.

There's an exit story too. Institutions and healthcare REITs like owning stabilized medical buildings for exactly these reasons, which gives a patient owner a natural buyer down the road.

The worst case, plainly. You're leaning on the tenant. If a practice fails, a specialized medical space takes time and money to re-lease, and a long lease to a weak practice is worse than a shorter one to a strong practice. Tenant quality is the deal.

Sticky tenants, recession-proof demand, an aging country, and a real buyer at the end. That's why I think of this as ballast.

If steady, boring medical income is a piece you're missing, reach out and I'll walk you through it.

Picture your dentist’s office. Same building for 15 years, probably 20.That stickiness is the entire investment. Our Med...
09/02/2026

Picture your dentist’s office. Same building for 15 years, probably 20.
That stickiness is the entire investment. Our Medical Real Estate Fund invests in medical and dental buildings held on triple net leases.

The tenant pays taxes, insurance, and upkeep. Healthcare demand doesn’t move with the stock market, and a practice that spent six figures on its buildout doesn’t relocate over a rent bump.

The pace tells you the machine works. In one week this summer, two portfolios closed, 10 buildings and $13.8M deployed. The fund has 86 buildings as of this week.

Let me lay it out for you. Targeted 7 to 8% distributions with a projected 2 to 3x multiple over the hold. I’d underwrite the low end of both. The worst case is concentration in healthcare tenants. If a practice fails, a medical buildout takes time and money to re-lease.

The operating team comes out of dental and medical operations, which is exactly who you want solving that problem.

The 2026 plan is properties purchased and operating before year end. That timing matters if depreciation is part of your tax plan this year.
Accredited investors only. Book a call.

P.S. Tax planning season is now. If you’re a high income earner selling a property or selling a business, now is the time to plan for the tax bill. Send me a message with the word TAX and I’ll send you our tax mitigation calculator.

08/31/2026

Everyone I talk to wants to invest in AI. I keep writing checks to sign companies and well drillers.

Our Expedition Blue Line Small Business Fund invests in a portfolio of six small businesses. Gas station signage. Industrial electrical. Residential well drilling. Steel canopy construction. Medical imaging equipment and service.

Every one an essential service, bought at 4 to 5x EBITDA with conservative leverage. The portfolio has paid investors 21.82% over the past seven quarters, about 3% a quarter, all from operating cash flow.

Past payouts don't promise the next ones. But seven straight quarters across six companies tells you something about the underwriting.

Here's why the timing matters.

The fund holds its final close in Q4 and then shuts to new investors permanently.

Coming in now means you're not underwriting a blind pool. The six companies are bought, integrated, and distributing. The sourcing and entry risk earlier investors carried is largely behind you. Targeted 3 to 5x multiple over the fund's life with an 8% preferred return.

Accredited investors only. If you want to walk through all six companies, book a call.

𝘗.𝘚. 𝘛𝘢𝘹 𝘱𝘭𝘢𝘯𝘯𝘪𝘯𝘨 𝘴𝘦𝘢𝘴𝘰𝘯 𝘪𝘴 𝘯𝘰𝘸. 𝘐𝘧 𝘺𝘰𝘶'𝘳𝘦 𝘢 𝘩𝘪𝘨𝘩 𝘪𝘯𝘤𝘰𝘮𝘦 𝘦𝘢𝘳𝘯𝘦𝘳 𝘴𝘦𝘭𝘭𝘪𝘯𝘨 𝘢 𝘱𝘳𝘰𝘱𝘦𝘳𝘵𝘺 𝘰𝘳 𝘴𝘦𝘭𝘭𝘪𝘯𝘨 𝘢 𝘣𝘶𝘴𝘪𝘯𝘦𝘴𝘴, 𝘯𝘰𝘸 𝘪𝘴 𝘵𝘩𝘦 𝘵𝘪𝘮𝘦 𝘵𝘰 𝘱𝘭𝘢𝘯 𝘧𝘰𝘳 𝘵𝘩𝘦 𝘵𝘢𝘹 𝘣𝘪𝘭𝘭. 𝘔𝘦𝘴𝘴𝘢𝘨𝘦 𝘛𝘈𝘟 𝘢𝘯𝘥 𝘐'𝘭𝘭 𝘴𝘦𝘯𝘥 𝘺𝘰𝘶 𝘰𝘶𝘳 𝘵𝘢𝘹 𝘮𝘪𝘵𝘪𝘨𝘢𝘵𝘪𝘰𝘯 𝘤𝘢𝘭𝘤𝘶𝘭𝘢𝘵𝘰𝘳.

I owned my practice real estate for many years. The buildings turned out to be some of the quietest, best money in healt...
08/28/2026

I owned my practice real estate for many years. The buildings turned out to be some of the quietest, best money in healthcare.

That’s the thesis behind our Medical Real Estate Fund. The fund invests in medical and dental buildings held on triple net leases. The practice inside pays the taxes, the insurance, and the maintenance. The landlord collects rent from a tenant who almost never leaves, because relocating a dental office means moving plumbing, imaging equipment, and patients.

The portfolio behind the strategy stands at 84 buildings. The current series is adding 21 more, with nine already closed.

Here’s the number my CPA cares about. Roughly 65 to 70% of the investment is projected to be deductible in 2026 through depreciation, passing through on your K-1. The plan is properties purchased and operating before year end, which is what makes the 2026 deduction work.
Targeted distributions are 7 to 8%. The IRR targets run higher, and I’d talk you off those numbers until you’ve walked the underwriting yourself.
Accredited investors only. If the depreciation math fits your 2026 picture, book a call.

P.S. Tax planning season is now. If you’re a high income earner selling a property or selling a business, now is the time to plan for the tax bill. Send me a message with the word TAX and I’ll send you our tax mitigation calculator.

Everyone I talk to wants to invest in AI. I keep writing checks to sign companies and well drillers.Our Expedition Blue ...
08/27/2026

Everyone I talk to wants to invest in AI. I keep writing checks to sign companies and well drillers.

Our Expedition Blue Line Small Business Fund invests in a portfolio of six small businesses. Gas station signage. Industrial electrical. Residential well drilling. Steel canopy construction. Medical imaging equipment and service. Every one an essential service, bought at 4 to 5x EBITDA with conservative leverage.

The portfolio has paid investors 21.82% over the past seven quarters, about 3% a quarter, all from operating cash flow. Past payouts don’t promise the next ones. But seven straight quarters across six companies tells you something about the underwriting.

Here’s why the timing matters. The fund holds its final close in Q4 and then shuts to new investors permanently. Coming in now means you’re not underwriting a blind pool. The six companies are bought, integrated, and distributing. The sourcing and entry risk earlier investors carried is largely behind you.
Targeted 3 to 5x multiple over the fund’s life with an 8% preferred return.
Accredited investors only. If you want to walk through all six companies, book a call.

P.S. Tax planning season is now. If you’re a high income earner selling a property or selling a business, now is the time to plan for the tax bill. Message TAX and I’ll send you our tax mitigation calculator.

"Recession-resistant" is the most abused phrase in real estate.Let me tell you what it actually means.Every sponsor on L...
06/03/2026

"Recession-resistant" is the most abused phrase in real estate.

Let me tell you what it actually means.

Every sponsor on LinkedIn claims their asset is recession-resistant.
Multifamily. Self-storage. Industrial. Hotels. (Yes, hotels.)

If everything is recession-resistant, nothing is.

Here's the real test. Ask one question:
"When household budgets get squeezed, does demand for this asset go up, down, or stay flat?"

That's it. That's the whole framework.

A few honest answers:

🏢 Class A apartments: demand drops. People trade down.
🏬 Class B/C apartments: demand often holds. People trade in.
🏠 Mobile home parks: demand often increases. It's the most affordable form of homeownership in the country, and supply is shrinking because no one builds new ones.
🅿️ Parking near dense employment: demand holds, sometimes grows as transit ridership shifts.
🏥 Medical office on long-term triple-net leases: demand is essentially decoupled from the cycle. People don't skip dialysis in a recession.
🏨 Hotels: demand collapses. (See: 2008, 2020.)

Notice the pattern. Recession resistance is about non-discretionary demand and supply constraint. Not vibes.

When you hear a sponsor say "recession-resistant," ask them which of those two levers their asset actually pulls.

If they can't answer in one sentence, they're using the phrase as marketing.

The boring, ugly, unsexy asset classes are usually the ones that hold up.

Because they solve a need that doesn't go away when times get tight.

What's your personal litmus test for a "recession-resistant" deal?

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