Alongside sharing interesting real estate themes and stories in my letters, I’m going to start fleshing out what I think is the biggest opportunity I’ve seen in my real estate career:

This letter breaks down why it’s happening.

TL;DR

• Real estate GPs - the people & organizations who find and raise money for real estate investments - have historically focused on big institutions as their LP investors because they can write big checks ($20mm-$1bn+)

• These pensions, endowments, sovereign wealth funds, etc. are tax-exempt and don’t care about all the tax advantages of real estate investments, i.e., what taxable investors care about

• Thanks to this tax-exempt customer focus, most real estate investment vehicles today are not designed for the taxable investor

• But that’s changing… (1) institutions are consolidating to the largest real estate investment managers, while (2) the growth of the taxable investor class is exploding via wealth transfer and wealth creation

• So, many of the real estate GPs that used to build investment products for pension funds are starting to build products for high-net-worth families

Thus, the thesis: over the next 5 years, we will see a wave of new real estate products for taxable investors — built specifically for individual outcomes with better transparency and education around the product offering.

Start with who the customer was

When a pension fund, a university endowment or a sovereign wealth fund buys a building, it pays no income tax on what that building earns. That’s the bargain Congress made: retirement savings and charitable endowments compound untaxed.

But nearly every feature that makes real estate attractive to a person is a tax feature.

Depreciation lets you report a loss on paper while cash is landing in your account. A 1031 exchange lets you sell a building, buy another, and owe nothing that year. Hold the thing until you die and your children inherit it with the gain wiped clean.

To a pension fund, that entire list is worth zero. You cannot take a deduction against income you don’t have.

So the industry did the rational thing and built products optimized for everything except taxes.

• Funds with a fixed ten-year life, because a fixed life produces a clean return number a consultant can benchmark

• Quarterly valuations, because allocators have to report something every quarter

• Corporate wrappers sitting between the investor and the building, because borrowed money creates a tax bill even for a tax-exempt buyer, and real estate runs on borrowed money.

All of that works. And none of it was designed against individuals.

It simply wasn’t designed for them.

Three reasons the benefits don’t come along

1/ Some of what a taxpayer can do is worthless to an institution.

• Reducing a tax bill through depreciation

• Deferring one through a 1031 exchange

• Erasing it through a step-up at death

All meaningless to a pension fund.

2/ One thing is forbidden to institutions.

Using the real estate for personal use… the pension trustee has a legal duty to act solely for the financial benefit of the people whose money it is. So a trustee cannot pay an extra dollar because the ski resort comes with member privileges, or because it’s a building on the main street of his hometown and he’s proud to own it. He is not permitted to want those things.

3/ And one thing is impossible.

Institutional money runs on clocks. Funds have end dates. Allocation policies force selling when the stock market falls and real estate suddenly looks too big a share of the portfolio.

Taxable investors have no clock and no policy, so you can hold forever and sell when it suits you.

Worthless, forbidden, impossible. That’s the complete list of what a taxable investor owns and a tax-exempt one doesn’t, and it compresses to five words: reduce, defer, erase, control, use.

Why it’s turning now

Three things are happening at once.

1/ Institutional capital is consolidating hard. The twenty largest real estate investment managers (think Ares, Blackstone, Carlyle, etc.) now take roughly half of all closed-end real estate fundraising, up about five points in a decade, and 17% of institutions say they intend to shrink the list of managers they work with. So if you’re not top twenty, that channel is closing.

2/ Wall Street’s answer for individuals hasn’t worked. Non-traded REITs, the packaged retail product, raised $5.7 billion in 2025, down more than 80% from the 2021 peak. That isn’t a demand problem. Individuals want this asset class. It’s a product problem: those vehicles charge for daily liquidity that most individual buyers will never use, and deliver none of the five verbs - reduce, defer, erase, control, use.

3/ And the money is changing hands. Cerulli estimates $124 trillion moves between generations through 2048. Estimates vary wildly and I wouldn’t defend that specific figure, but the direction isn’t in dispute.

So we’re living at an intersection with: (a) strong operators who need new capital + (b) a growing cohort of taxable investors - families, founders, operators’ own money - who need the tax advantages of the asset class.

If you’re the one investing

Two questions...

How many layers sit between me and the building?

Five things can be in there: an advisor’s platform, a fund, a corporate wrapper, a sponsor, an operating team.

Each takes a fee, or a right, or both. The ones that take rights are the dangerous ones, because they don’t show up as a fee in year one. They show up three decades later as a tax bill for your children.

What’s the after-tax return?

Not the IRR. The after-tax number, for someone in your bracket, in your state, with the depreciation schedule attached.

A sponsor who built the product for individuals will have it ready and be pleased you asked. One who didn’t will send back a pre-tax return measured against an index you have no stake in, and you’ll have learned more from the dodge than you would have from the answer.

If you’re the one raising

If you’ve spent a career raising from institutions, the opportunity here is not to market harder to individuals. It’s to build a different product.

Concretely: no wrapper where none is needed.

• A cost segregation study run and modeled

• An after-tax return in the deck

• A hold period that isn’t governed by a fund clock

• Use rights where the asset supports them

Almost nobody does this today, because existing tax-exempt LPs never needed it.

The trust problem also changes shape.

Something like 99% of private real estate capital has always moved through personal introduction, and there’s a legal reason for that: until 2013, publicly soliciting investors for a private deal was effectively off limits. It no longer is.

Trust can be built in public now, through teaching rather than through a shared dinner table, and the operators who start building an audience this year are the ones who will be able to raise from it in three.

The rule of thumb

Count the layers, then ask for the after-tax number.

If a sponsor answers both without flinching, they built it for you.

If they can’t, they built it for someone else.

Buy Box is written for taxable capital: families, founders, family offices, and operators investing their own money. Nothing here is tax or legal advice, and every situation turns on facts this letter doesn’t know about yours.

Sources: US CRE investable universe and institutional-quality share, Clarion Partners (H1 2025). Manager concentration and non-traded REIT fundraising, McKinsey Global Private Markets Report 2026. Generational wealth transfer estimate, Cerulli Associates.

It’s not often you see a gas station post a help wanted ad for a Barista Associate. Or offer a $9 gourmet hot dog. Unless you’re walking down Washington Street in Yountville, CA, the Disneyland of Napa Valley.

On one end of the fairytale street sits Thomas Keller’s three-Michelin-star French Laundry, flanked by a supporting cast of Bouchon Bakery, Bouchon Bistro, Ad Hoc, and Bistro Jeanty. A half mile of tasting menus in a town of 3,000 people.

Now walk to the opposite end, to the last building on Washington Street before the sidewalk ends.

It’s a gas station. And of everything on this street, it’s the parcel I’d most want to own.

Why gas station real estate

Whether in Yountville, Dallas or a random suburb of New Jersey, gas stations usually sit on a hard corner with curb cuts, traffic count, and visibility from both directions. Most towns would never entitle these parcels again at any price. And if they weren’t gas stations, it would be the most expensive dirt on the block.

But nobody wants it.

More than 500,000 underground storage tank releases have been confirmed in this country, and roughly 60,000 contaminated sites are still waiting on cleanup. Remediation on a single station can run past a million dollars. But the cost isn’t really the problem. The problem is that nobody knows the cost until they dig. Lenders won’t lend against an unbounded number and funds won’t underwrite one.

And because the dirt is priced as a liability, owners don’t bothers much with what sits on top of it. So most gas station convenience stores dispense salt, sugar, calorie-filled bags of junk food, shitty coffee, and domestic tall boys.

Which is the arbitrage opportunity.

The best corners in America are available at a discount, with the lowest bar in retail sitting on them.

As long as you stop looking at them like gas stations.

The Honor Market Story

Honor Market opened on Washington Street in Yountville in 2011 as Kelly’s Fuel & Provisions and took its current name in early 2023. It’s owned and run by Hillstone Restaurant Group (Houston’s, R+D Kitchen, Palm Beach Grill, White House Tavern, etc.).

When they bought the property, they were not shopping for a gas station.

Hillstone bought Washington Square, a two-acre parcel at Washington and Madison, with a shuttered Exxon attached to it. The gas pumps were considered an ugly blemish and a liability, and the reason two acres on this tony street were available.

Then the creative geniuses at Hillstone turned one dead Exxon station into a four-concept campus, that included Honor Market, on Yountville’s main street—which was never going to allow more commercial square footage.

No one at Hillstone cared if they made money on fuel. They were selling organic wines, flat whites and $9 gourmet hot dogs on poppyseed brioche buns with homemade relish and on a prime retail corner.

Keeping a gas pump was the political lever the town needed to say ‘yes’ to the rest of the prime corner development.

Napa is not the only place this is happening

Twenty minutes north, Joel Gott runs Station St. Helena on the same idea—brioche doughnuts in the morning, pizza at night—except Gott owns the retail and Napa Valley Petroleum owns the filling station. You can split the stack if you don’t want the tanks.

In 2027, Beverly Hills will get Maggie’s Refuel. Maggie’s just raised $2M in pre-seed funding from Matchstick Ventures, Mucker Capital, and Everywhere Ventures to build a luxury, hospitality-driven gas station and convenience concept.

Meanwhile, Buc-ee’s has been running the highway version of this for years.

Here is why it works, in round numbers

Option 1: Buy the corner for $2 million and keep it a gas station. You’ll clear about $200,000 a year after setting aside money for the tanks—a 10% yield, which sounds excellent. Then try to sell it. It’s a gas station business, it trades at eight times earnings, and it’s worth about the $2 million you paid. And your buyer pool is three guys.

Option 2: Buy the same corner for $2 million and stop treating it like a gas station. Spend $600,000 cleaning it on a fixed-price contract and a million on the shell—hood, grease trap, power, restrooms, etc. You’re in at $3.6 million. Lease it to a food operator for $350,000 triple-net and you’re at a 9.7% yield, which is the same yield you had before, except now somebody else runs it.

Then sell it. It’s not a gas station anymore. It’s a leased fee at a 6.5% cap. $5.4 million.

Now widen it out

There are roughly 450,000 brownfields in the United States and nearly half are petroleum sites, most of them former or current gas stations. Most of those sites are, by definition, on the best corners of town… signalized intersections, curb cuts, traffic counts, and visibility from both directions… parcels that in most jurisdictions could not be entitled today at any price.

Every one of them is priced with a tank discount.

Which means the gas station is not really an asset class. It is the cheapest available way to buy an irreplaceable corner. And once you own the corner, it does not have to stay a gas station. It can become a market, a restaurant, four concepts, or the anchor of a two-acre campus.

The arbitrage was never between a bad gas station + convenience store and a good one. It’s between the price of a gas station vs. the price of the corner underneath it.

Everyone loves the Richard Branson - Necker Island story. “Cowboy entrepreneur buys luxurious private island for pennies.”

In reality, it wasn’t some genius land grab.

Yes, Richard Branson bought Necker Island in 1979 for $180,000 against an asking price of $6 million, having first offered $100,000 because “that was all he had.” It has become a negotiation parable for business self-help books: lowball everything, and sometimes the seller will say yes.

But he wasn’t actually buying an island cheaply. He was buying an option to build a resort. And the land purchase was 1.8% of the first phase of development.

The condition

The seller was John Lyttelton, the 11th Viscount Cobham, and he refused the $100,000 outright. Then, a year later, he took $180,000, which tells you about how many other buyers were in the room for 74 acres of scrub in the British Virgin Islands with no fresh water, power or docks, and a population of feral goats that had eaten most of the vegetation.

In the sale, the government required the island to be developed within four years, or it reverted to the state.

So Branson, 29 and running an early-stage record label, committed to building a resort in a place with no infrastructure, on a deadline, in a jurisdiction where he nearly failed to get an Aliens Land Holding License because the governor considered the music business disreputable.

So the thing acquired for $180,000 was not an asset. It was an obligation with a clock on it, which is why it was available at 3% of ask.

What had to be built

Everything.

Fresh water on a dry Caribbean island means desalination, which means power, which in 1979 meant generators and fuel delivered by boat.

Then a dock for access, housing for staff, and buildings capable of standing up in a hurricane belt, constructed from materials that arrive by barge at multiples of mainland cost.

The Great House opened around 1982, inside the deadline, at about $10 million in period dollars.

What that capital produced is not a vacation home.

Necker today runs roughly 100 staff for a maximum of a few dozen guests, and rents for something on the order of $102,500 a night.

He built a hospitality operating business with a very high fixed cost base and a single location, which happens to look like a beautiful home.

The other thing the capital produced was a rebuild schedule. On August 22, 2011, lightning from Tropical Storm Irene burned the Great House to the ground with about twenty people inside, Kate Winslet among them, all of whom got out.

Most of it was rebuilt by April 2018. Twice in under forty years, the improvements were destroyed.

Then, in April 2020, with Virgin Atlantic and Virgin Australia facing collapse, Branson offered to mortgage Necker Island to raise money for the airlines.

Forty-one years of development had turned a $180,000 obligation into something a bank would lend against. The island’s final function was collateral.

The actual private island playbook?

I haven't bought one, but this seems to be the general rule of thumb if you want to take a look at the several hundred islands on the market worldwide, going from anywhere between $74,000 for a quarter-acre in a Nicaraguan lake and $120 million for an atoll in the Maldives.

Price the build, not the buy. The purchase price of an undeveloped island is close to noise. Assume the acquisition is a rounding error against infrastructure, and underwrite the second number first. Islands advertised at $405 an acre are not cheap; they are unpriced.

The discount lives in the obligation. Branson did not get 97% off because he negotiated well. He got it because the island came with a four-year development requirement and a reversion clause. In illiquid markets the price break is compensation for a condition, and the investment thesis is deciding whether the condition is survivable.

Underwrite water and power before anything else. No fresh water means desalination, desalination means continuous power, and continuous power on a remote island means fuel logistics forever. An island without a water answer is not a development site at any price.

Assume no financing at acquisition. Banks do not lend against undeveloped islands. They will lend against a functioning operating business on one, which is a different asset entirely and takes decades to become.

Budget the rebuild into the model. Two total losses in forty years is not bad luck in that geography, it is the base rate. Insurance in the hurricane belt is expensive where it exists at all, and the honest model self-insures.

The island is the cost, but the operation is the asset. A hundred staff for a few dozen guests is the actual business, and the land is the least interesting part of it.

None of which is an argument against buying an island.

It’s an argument for understanding that Branson did not buy an island for $180,000. He bought a four-year deadline, and then spent the next four decades meeting it.

QROF 2.0 is not the name of Elon Musk’s next kid.

But it should be, if he wants to start naming them after really smart tax strategies that will protect his K-1 income (admittedly he probably has negative K-1 income given capex & ops losses from startups).

Either way, QROF stands for Qualified Rural Opportunity Funds.

Which sounds incredibly esoteric - and it kind of is - but also might be the single best tax sheltering strategy for anyone selling a business (or stock, or crypto) in the next couple of years, starting next year.

The new versions will go live in January 2027 thanks to the recent One Big Beautiful Bill Act.

Here’s how it works, using a (hopefully) easy to follow fictional case study.

1/ Tom’s bill

Tom is 65.

He spent 30 years building an HVAC and plumbing contractor outside Charlotte. Thirty trucks, twenty employees, and a private equity-backed rollup that just bought it for $3 million.

His basis is roughly nothing (he built it with his own money) but now he has to pay ~$864K in taxes on the $3 million gain

• Federal long-term capital gains at 20%: $600,000

• Net investment income tax at 3.8%: $114,000

• State income tax, call it 5%: $150,000

Tom nets $2.14 million on a $3 million sale, and he writes the check next April.

Tom talks to his CPA about how to avoid paying the IRS in full:

“How about 1031?” he asks. It doesn’t apply — he sold stock, not buildings.

She offers “a charitable remainder trust?” Tom doesn’t want an annuity, he wants to own something.

“How about an installment sale?” she asks. Can’t. The buyer wants a clean exit.

2/ Enter Rural Opportunity Zone Funds

Opportunity Zones were made permanent, with a new map effective January 1, 2027 and running through 2036.

Opportunity Zones are neighborhoods where the US & State governments agree need real estate investment.

For individuals and funds that invest in these areas, they get to:

• Shelter a percentage of K-1 / 1231 gains; AND

• Not pay taxes on future capital gains from the investment (if they invest $1 and get back $3 in the end, they keep all of it); IF

• They keep their money in for 10 years

There’s some other nuance but let’s keep moving.

But this statute carves out a separate, even better-treated sub-category: the Rural Opportunity Zone Fund - which invests in rural areas.

Three things happen when Tom rolls his $3 million into one.

First, he defers the whole bill.

Not forever — deferral now runs five years from the investment. But $864,000 that stays invested for five years instead of leaving in April is real money.

Thirty percent of the gain is forgiven outright.

The standard urban step-up is 10%. Rural is 30%. On a $3 million gain that’s $900,000 of gain permanently excluded, worth about $259,000 of tax.

Tom’s bill drops from $864,000 to roughly $605,000 — and he pays it in 2031, not 2027.

Hold ten years and the appreciation is untaxed.

Including — and this is the part people usually miss — the depreciation recapture. Every dollar of cost segregation Tom claims along the way gets forgiven at exit rather than clawed back.

A 1031 doesn’t do that. A 1031 drags the recapture behind you forever.

And one more thing, which is a big reason this is interesting: in a rural tract, the substantial improvement test drops from 100% of basis to 50%.

So if you buy a $4 million property, instead of having to spend another $4 million to qualify, you spend $2 million.

And two million on a four-million-dollar property isn’t a heroic renovation. It’s a normal one.

(NOTE: In traditional OZ deals, the developer usually needs to invest at least 2X into the asset for it to qualify for the OZ tax treatment)

That change moves Rural QOFs from “ground-up development only” (traditional OZ) to “buy the tired asset and fix it,” which is where most of the risk-adjusted return in this business actually lives.

3/ The town

Tom’s fund goes to Spartanburg County, South Carolina.

Spartanburg is not a distressed market. It’s the opposite. Industrial vacancy across Greenville-Spartanburg fell to 5.3% in Q2 2026, down from 7.4% a year earlier, with BMW alone taking 918,000 square feet. County population grew 3% in a single year to 380,857. South Carolina put $9.12 billion into business recruitment in 2025 — its third-biggest year ever — and the Upstate captured a large share of it.

The jobs are arriving. But the housing is not. The county planning commission spent its January meeting on the “missing middle” gap created by workforce growth at BMW and Milliken. Local leaders are openly worried that growth becomes a net negative for middle- and lower-income residents.

Now look at the Treasury eligibility file. Spartanburg County has ten rural tracts that qualify for the new map. Their median family income is $39,350 against an area median of $78,303 — half. Median poverty rate: 41%.

So Spartanburg is a great example of the thesis. Sub-5% industrial vacancy nine miles away, and a mill village at 41% poverty with no capital in it.

4/ What Tom builds, and what he makes

The fund Tom invests into buys a 96-unit 1970s garden apartment complex for $4 million — about $42,000 a door — and puts $2 million into it.

Rents go from $675 to $1,050. Still under 80% of area median. Still the cheapest renovated product within twenty minutes of the plants.

Upside case, ten years out: NOI grows from roughly $290,000 to $700,000.

At a 6.5% cap that’s $10.7 million. Debt amortized to $2.4 million. Tom’s equity: $8.3 million.

His gain is $5.3 million. He also claimed about $1.4 million of accelerated depreciation along the way, which sheltered his distributions.

His tax on all of it: zero.

Run the same deal outside a QOZ and Tom pays $864,000 up front, invests $2.14 million instead of $3 million, and hands back roughly $1.4 million at exit between capital gains and recapture. The spread is somewhere north of $2 million on a $3 million check.

Meanwhile 96 families in a 41%-poverty census tract live in renovated units instead of failing ones, and Spartanburg County gets a little closer to housing the workforce it just recruited.

5/ What would have to go right

All of it, is the honest answer.

The tract has to actually get designated — states nominate this fall, and there are more eligible rural tracts nationally than there are total designation slots in the entire country.

Rents have to hold.

The renovation has to come in on budget.

And Tom has to not need his money for ten years, which is the constraint that disqualifies most of the Toms I meet.

But notice what the tax code is doing here. It isn’t paying Tom to build a luxury tower in a gentrifying tract. It’s paying him 30% up front and 100% at exit to fix ninety-six units in a mill village next to a BMW plant.

For once, the incentive points at the right building.

Not tax advice. Rural QOF treatment turns on final Treasury guidance that hasn’t landed yet. Talk to your CPA before you wire anything.

In college, a handful of my friends didn’t live in the dorms or a slummy rental house like the rest of us. Their parents had bought them a townhouse near campus. At the time I filed it under rich-parent flexing, the same bucket as the new Range Rover and the spring break in Aspen.

But I was wrong. It was not a flex. It was a strategy, and a good one.

The parents who did this weren’t spending money on their kid’s housing. They were moving money out of an expense and into an asset, financing it on terms a normal investor can’t get, letting other people’s children pay the mortgage, writing off a chunk of it, and pocketing four years of appreciation on the way to a tax-free exit.

Here is how the play works, in plain terms.

Start with the housing stipend

Every parent of a college kid is going to pay for housing. Four years of dorms and a meal plan runs $60,000 to $90,000 at a lot of schools, and at the end of it you own nothing. The kiddie condo is the decision to route that same spending through an asset you own.

The unlock is the financing, not the house

If you, the parent, buy a condo for your kid to live in, the bank calls it an investment property. That means 20% to 25% down and a higher interest rate. Not great.

But if your kid is the one who lives there, it’s an owner-occupied home, and you can co-sign.

This is the FHA “kiddie condo” loan:

• The student is the occupying borrower,

• The parent is a non-occupant co-borrower,

• The down payment drops to 3.5%.

Same house, and same family, but radically different terms.

On a $500,000 townhouse that’s the difference between putting down $17,500 and putting down $125,000.

You are buying the exact same building the investor down the street is buying, and getting in for a fraction of the cash at a better rate, purely because your teenager sleeps there.

Make the roommates pay the mortgage

Maximize the number of bedrooms.

Your kid takes one room rent-free; then you rent the others to their friends at the going rate, which in a college town is rarely soft.

A four-bedroom townhouse with three spare rooms at $900 a month generates $2,700 a month from other people’s kids. In a lot of markets that covers most or all of the mortgage. Your child lives for close to free, and the tenants are effectively paying down your loan every month.

Then write part of it off

Of a $500,000 townhouse, say $100,000 is land, which you can’t depreciate, and $400,000 is the building. Your kid takes one of four bedrooms, so about three-quarters of the house is a rental. That leaves roughly $300,000 you can write down.

Normally that comes off slowly, about $11,000 a year over 27.5 years. Two moves front-load it into year one:

• Furnish it and deduct the furniture now. Beds, desks, couches, and appliances for the rented rooms are short-life property, and under the Big Beautiful Bill’s 100% bonus depreciation you write the whole thing off the first year. Call it $15,000.

• Run a cost-segregation study. A cost seg carves out the parts of a building that wear out fast, the flooring, cabinets, fixtures, driveway, and landscaping, and 100% bonus lets you deduct them immediately instead of over decades. On a $300,000 rental basis that’s often $40,000 to $50,000 in year one.

So year one can throw off close to $65,000 to $70,000 of depreciation against about $32,000 of rent.

And you can deduct the furnishing, repairs, mileage, insurance, and property taxes on the rented share on top of it. You can even write off flights and meals related to “managing the property.”

Note: depreciation is a paper loss, which means the building can be going up in value and paying you rent while showing a loss on your return. The rent comes in completely tax-free, and the leftover loss banks for later.

Buy a townhouse, not a condo

A high-rise condo is basically air rights with a monthly fee.

A townhouse sits on actual dirt, and dirt is what appreciates. Townhouses also come with more bedrooms, which means more rent-paying roommates, and students would rather live in one than in a tower with an elevator and a $700 HOA.

More land and more rent, with less overhead. Which is the same reason those parents twenty years ago kept buying townhomes and not studios.

The exit is where it gets really good

Four years in, the roommates have paid down your principal and the place has (usually) appreciated.

Two paths:

Option 1

Put the title in your kid’s name and have them live there as a primary residence for at least two years, and when they sell, the first $250,000 of gain is tax-free under the Section 121 exclusion.

A 22-year-old walking out of college with a six-figure, tax-free check and a credit history is a hell of a graduation gift.

Option 2

Keep it in your name. Tier 1 college-town demand doesn’t slow down; there’s a fresh crop of freshmen every fall and a line of parents behind them who don’t flinch at the rent.

Hold it as a rental, refinance to pull your cash back out tax-free, or 1031 the gain into the next one and never pay tax at all.

The math, with real numbers

Start with a $500,000 townhouse, 3.5% down.

• In the door: $17,500 down, about $12,500 in closing costs, and $18,000 to furnish it. Call it $48,000 to start.

• Three roommates at $900 per month. That $2,700 covers most of the note.

• Your net carry runs around $1,700 a month (roughly what you’d have paid to house your kid anyway).

• Four years of 4% appreciation takes the house fto about $585,000, and the roommates have chipped the loan down by roughly $24,000.

At graduation, you sell. After selling costs and paying off the loan, you walk away with about $90,000.

Now line them up:

• Dorm: spend about $70,000 over four years, own nothing.

• Kiddie condo: spend roughly the same to carry it, collect four years of tax-free rent, and hand your kid a $90,000 check on the way out (tax-free, if it’s in their name under the Section 121 exclusion).

None of this is exotic. It’s the most ordinary asset in America, bought on the best terms available, paid for by other people, and sold into a purpose-built tax exclusion.

(The usual caveat: this is how the mechanics work, not personal tax advice. Financing terms, occupancy rules, and the Section 121 clock have real requirements, so run your specific situation past a CPA and a lender before you buy anything.)

One rule above all others

Do this with a daughter.

The entire thesis rests on the assumption that the person living in your appreciating asset respects drywall. A daughter, statistically, keeps the security deposit intact. A son turns your carefully modeled capex reserve into a line item called “replace everything” and introduces your insurance company to words like “the fire started in the kitchen but.”

I sat across from a buddy in February at one of his two luxury resorts in Cabo.

He barely touched his food - he just watched the room. A server took too long reaching a table on the terrace and he clocked it. He knew the name of the couple by the pool who had come back for their ninth year. He knew that the west-facing suites sell out first in October and why, that the busiest bar shift is not the one you would guess, and that the entire vibe hinges on a doorman who has worked the entrance since the resort opened.

He never once mentioned a cap rate.

He runs a hotel, and in two hours he taught me more about how a building makes money than most owners learn in a career.

Sitting with a great hotel operator is nothing like sitting with an owner or a lender. The financier sees a stack of cash flows, a debt schedule, an exit. The operator sees the hundred small decisions that decide whether those modeled cash flows become reality.

That gap — between seeing a building and running one — has fascinated me for years. And I think it’s now the most important gap in the industry.

The financier’s era is over

For most of two decades, real estate was a financier’s game. Cheap debt and falling cap rates did the heavy lifting; buy well, hold, refinance, and the market handed you a return. Institutional multifamily cap rates compressed from the high 6s after the financial crisis to the low 4s by 2021, and that move alone, with no operational improvement whatsoever, roughly doubled the equity on plenty of deals. Then the lever broke. Rates reset, spreads widened, and the free money that made financial engineering look like genius evaporated.

NOI growth now has to be earned, one operated dollar at a time, instead of manufactured on a spreadsheet.

Which raises an uncomfortable question: who actually knows how to earn it? The one discipline that never had the financial-engineering crutch, where every point of margin had to be operated into existence, is hospitality. Hotel operators have run the hard version of this business for a century.

The rest of real estate is about to join them.

What great operators do that financiers can’t

A handful of traits separate a great hotel operator from someone who merely owns a hotel. Most real estate never forced anyone to develop them. Five stand out.

They are obsessed with the guest, not the spreadsheet.

Isadore Sharp built Four Seasons on a single conviction: that service, not marble, is the product. Ritz-Carlton famously lets any employee spend up to $2,000 to fix a guest’s problem on the spot, no manager required, because a ruined stay costs far more than $2,000 in lifetime value.

A great operator sweats the details a financier will never see on a rent roll, because in hospitality those details are the revenue. The lender underwrites the building; while the operator underwrites the experience of being inside it.

They build brands, not boxes

An Aman commands nightly rates a comparably luxurious box cannot touch, because the guest is buying an identity, not a room.

Ian Schrager turned the hotel lobby from dead circulation space into the most valuable social real estate in the building, and priced the rooms accordingly. A financier sells a commodity and competes on basis; an operator manufactures a reason to choose this place over the identical one across the street, then charges a premium for having done so.

Brand is the pricing power — not marketing gloss on top of the asset.

They run a topline engine

Revenue management was born in hospitality and aviation, not in real estate.

A good hotel reprices its inventory hundreds of times a year against demand, weather, events, and the calendar, while the average landlord reprices once a year at renewal.

Then layer on everything beyond the room: food and beverage, the spa, events, parking, the rooftop bar that turns a sleepy Tuesday into a profit center.

Operators grow the top line every single day rather than waiting for the market to reprice the asset for them. That is a fundamentally different metabolism than “collect rent, control expenses, wait for the exit.”

They win on people and culture

Hospitality runs on teams, and the experience is ultimately delivered by a housekeeper, a line cook, and a night manager handling a complaint at 2am.

Danny Meyer built an empire on what he calls enlightened hospitality: hire for emotional skill, take care of the staff first, and let that flow through to the guest. Great operators recruit, train, and retain people who deliver the same standard on the worst night of the year as the best.

A financier can model turnover as a line item. While an operator knows it is the lynchpin of the business, because the real asset walks out the door every night and has to choose to come back.

They merchandise and adapt

The best operators treat a building as a living business to be merchandised, not a static asset to be held. They read demand and reprice into it. And reposition a tired property under a new flag, reprogram the ground floor, chase the season, and kill what isn’t working before it drags.

Where the financier’s instinct is to protect the pro forma, the operator’s instinct is to keep changing the offer until the market pays more for it.

Every asset class is becoming a hotel

None of this stays contained in hospitality.

Every corner of real estate is drifting toward the hotel model: shorter duration, a service layer, a brand, dynamic pricing.

• Multifamily is sliding toward branded and serviced living, with amenity programming and short-stay inventory that looks a lot like a front desk.

• Retail survives only by selling experience

• Office is being dragged toward hospitality-grade amenities and flexible terms because the tenant now expects to be hosted, not just housed.

The hotel operator has been living in that future for a hundred years. Everyone else is arriving late.

Commoditized money earns a commoditized return, and the premium is accruing to whoever actually runs the thing. The best operators will increasingly set terms rather than take them.

The future of real estate looks a great deal like the hotel business, and it will not be inherited by the allocators. The operator eats the financier.

A few years ago a work trip took me to Melbourne and Sydney, and I tacked on a solo long weekend down the coast in Lorne. I came back obsessed.

Melbourne is greener and more lush than any American city, and the commercial buildings are genuinely beautiful, better designed and better maintained than anything in a comparable US downtown. The restaurants pull from everywhere on earth, which isn’t unusual for a global city, but what was unique was the harmony of the people. The diversity wasn’t just tolerated, it was embraced, and everyone seemed genuinely proud about it (juxtapose to the inherent racial tensions in literally every US metro).

Then I drove the Great Ocean Road to Lorne, which embarrassed every beach town I’ve ever loved in the US. Waterfalls, wildlife, surf, world-class restaurants, old school ice cream shops, and none of the douchebaggery that comes with your top American beach towns.

I flew home with an obvious question for any real estate entrepreneur: if this place is this good, why isn’t more American capital here?

The answer isn’t that the opportunity is missing. It’s that the playbook is only now arriving.

The playbook

For the last 20 years, some of the best risk-adjusted money in US real estate came from a single, repeatable move.

• Find a boring asset class still owned by mom-and-pops: self-storage, manufactured housing, car washes, RV parks, vet clinics

• Roll up the scattered pieces, professionalize the operations, create synergies, market better, etc.

• Then sell the assembled portfolio to a big institution at a lower cap rate than you paid for the parts.

You made money twice. Once on the operational lift, and again on the cap-rate compression that shows up the moment a large buyer wants scale.

Everyone in the US knows this now. The assets are priced for it, and the easy returns are mostly gone.

Australia is where that game is just starting. Same fragmentation, same mom-and-pop ownership, and, most importantly, the institutional buyers are already lining up to take finished portfolios off your hands. The ending is proven, but the middle is wide open.

Why it works here

Three things make Australia the right place to run this play, and none of them require a spreadsheet to understand.

It’s a safe place American money forgot. Australia is one of only about ten countries in the world rated AAA by all three major agencies, and it went roughly 34 years without a recession. For a decade, US investors chased yield into Europe and riskier emerging markets and skipped the most stable economy in the Pacific. It’s under-owned by American capital, which is why there’s still room to move before prices reflect it.

The country is still growing. While the US and Europe flatten out or shrink, Australia’s population keeps climbing, headed toward about 31.5 million by the mid-2030s, mostly through immigration. More people every year means more demand for the buildings underneath these businesses. You’re investing with the tide, not against it.

There’s a deep-pocketed buyer waiting at the finish line. Australia requires workers to save for retirement, and that rule has built a A$4.4 trillion pension pool, on its way to A$8 trillion. That money has to be put to work at home, and it buys these kinds of stabilized, income-producing portfolios. So when you’ve done the hard aggregation work, there’s a natural, well-funded buyer ready to purchase it. The hardest part of any roll-up, the exit, is already solved.

Put simply: a safe country, a growing one, and a guaranteed buyer at the end.

Where to point it

The play only works if you aim it at the right asset classes: fragmented today, institutional tomorrow. A few are lining up.

Self-storage is still about half-owned by independent operators, and the big exits are already printing. Brookfield and GIC just took National Storage private for roughly A$4 billion. The window to aggregate is open right now.

Land-lease communities, essentially professionally run manufactured-housing neighborhoods for retirees, are moving from a sleepy caravan-park world into a real institutional class. Aveo sold for A$3.85 billion, and GemLife went public at around A$750 million. An aging population does the rest.

Childcare property trades on long, government-backed leases where the tenant covers most costs. A record A$1.44 billion changed hands in 2025, and it’s still mostly private ownership consolidating toward institutions.

Then there’s medical office, the one still earliest in its cycle, and the one I find most interesting. Roughly 92% of it sits outside dedicated fund managers. Owners are capital-constrained and selling piecemeal, often off-market, and buildings are trading below what it would cost to rebuild them. It’s the textbook version of the setup that made fortunes in US storage 15 years ago.

None of this is exotic. It’s the most familiar strategy in American real estate, but pointed at a market that hasn’t been picked over yet. And it’s itching for that fast-growing bucket of US private wealth money.

Tomorrow, we’re breaking down this big-box evolution—and the related mispriced retail real estate opportunities—with Brixton at 3pm ET. Register here.

Growing up a Yankees fan, every break in the game came with the same advertisement jingle: “Gotta go to Mo’s.”

Modell’s Sporting Goods ran ads on MSG (later, YES Network) so relentlessly that by the time I actually walked into one, sometime around age ten, I thought I had arrived at the center of the known universe—it had walls of jerseys, racks of cleats, and a whole aisle of just baseballs. It was, genuinely, heaven.

Modell’s was was part of a generation of big-box retailers that created 90’s retail destinations. Barnes & Noble, where a kid could sit on the floor reading for two hours without bother. Dick’s Sporting Goods, with the batting cages and the putting green. Circuit City, where families went on Saturday afternoons to stand in front of wall-mounted TVs they couldn’t yet afford.

Then, Amazon killed them.

Circuit City was gone by 2009; then Borders in 2011. Pier 1, Toys “R” Us, Bed Bath & Beyond, Sports Authority, Tuesday Morning: the list kept growing for a decade. And the lesson the real estate market took from them was: “big-box retail is a melting ice cube; avoid them as anchor tenants.” Buy small-box strips tenanted by restaurants and salons and urgent cares, i.e., the categories Amazon cannot replicate.

That lesson was half right.

The retailers that died were the weakest operators in categories where e-commerce had the clearest advantage. But the retailers that survived did something the market has not fully re-underwritten—they stopped being stores.

The Big Box Evolution

Kroger

They are really a last-mile fulfillment hub that happens to sell groceries. Seventy percent of online grocery orders fulfill from the store, not a warehouse, with billions invested in back-of-house staging, racking, sortation, and curbside infrastructure.

But the margin story is the real story. Retail media, a concept pioneered by Amazon and Walmart over the past five years (retailers selling ad space across their digital and physical properties to consumer brands), generated approximately $1.5 billion of Kroger’s roughly $5 billion in earnings last year. Private label sales hit a record $282.8 billion nationally in 2025, now 23.5 percent of total grocery volume, redirecting margin from national brands to the retailers themselves.

A Kroger in 2026 is a fulfillment center, an advertising platform, and a private-label brand house operating behind a grocery entrance.

Target

Target fulfills 97 percent of its digital orders from stores—the same buildings where customers push red carts past end caps. Product arrives through the loading dock and, increasingly, never touches a shelf. Store-based fulfillment across major retailers grew 35 percent or more annually from 2020 to 2025.

A retailer cannot close a store that fulfills half its digital volume without dismantling its own logistics network. The switching cost is not a lease penalty. It is the destruction of a supply chain node.

Best Buy

Best Buy is an omni-channel revenue generator. They run Geek Squad installations, Best Buy Health for seniors, in-home tech support, and store-within-a-store partnerships with IKEA for kitchens and laundry.

Walk into a Best Buy in 2026 and the sales floor is one layer of a business that now includes services, healthcare, and logistics. The relocation friction on a box running a Geek Squad bay, an IKEA display, and a healthcare division is categorically different from the relocation friction on the Circuit City it replaced.

The Same-Day Arms Race

Amazon forced the entire retail industry into a same-day delivery arms race, and the only way to compete without Amazon’s distribution network was to turn stores into warehouses.

The buildings now function as logistics infrastructure:

• Proximity to the end consumer,

• Loading dock access,

• Backroom fulfillment capacity

These are the same attributes that made industrial real estate a generational trade over the past decade, and now describe the operating profile of a grocery-anchored strip center.

But the real estate market has not caught up. Anchored strip centers are trading at 7 percent cap rates in markets where apartments trade at 5 percent. The cap rate spread between anchored retail and comparable asset classes is wider than the fundamentals justify, priced on a version of these tenants that no longer exists. The “retail is dead” crowd is measuring foot traffic, while the operators making money are measuring dock throughput.

Blackstone is on the offensive. In February 2025, it paid $4 billion to take ROIC private, 93 grocery-anchored centers on the West Coast at a 34 percent premium to market. The rest of institutional capital is still catching up, and the window to buy anchored retail at current cap rates is narrowing.

Tomorrow, July 24 at 3pm ET, Thesis Driven sits down with Rob Taylor and Grant Brutten of Brixton Capital to break down the evolution of the big-box tenant, the fulfillment infrastructure layer that locks these tenants to their physical locations, and why the most avoided asset class in retail real estate may be the most mispriced. Register here.

The wait time for a new Bombardier Global 8000 is 2029.

And the global billionaire population just hit 3,110, with 89 new people per day entering “UHNWI” status (+$30mm in net investable assets).

Combine those two facts, and you can come to a pretty simple conclusion: there is a fast-growing (and frustrated) waitlist for private jets.

But the second-order effect is less obvious: all those jets need hangars, fuel, terminals, and tarmac… private jet infrastructure is extremely constrained.

These supply-demand dynamics are powering a niche corner of real estate that's rarely discussed, but will be a major play over the next decade as the K-shaped economy grows.

Some relevant news & facts frame up the sector

KKR bought Atlantic Aviation in 2021 for $4.475 billion. They merged it with Ross Aviation, grew the platform to over 100 locations, and are now selling it to Apollo and Singapore’s GIC for roughly $10 billion. That’s approximately a 15x return on equity in five years.

Yes, this sounds more like a tech multiple than a real estate return, and that’s because private aviation real estate sits at a strange and lucrative intersection:

• the physical infrastructure is essential, but

• the supply is permanently constrained, and

• the demand curve is a function of global wealth creation.

There are 3.4 million business aviation operations in North America annually, up 33% from pre-COVID levels. NetJets alone operates 845 jets. The fractional market has grown 75% since 2019. And the industry calls the gap between aircraft growth and facility capacity “the $10 billion hangar problem.”

The good news for investors: entire ecosystem is investable.

Here’s how the investable ecosystem breaks down

Note: for the aspirational jet owner, I hope, if nothing else, this helps with your private jet IQ in cocktail conversations.

FBOs: The anchor asset

A Fixed Base Operator is the private aviation equivalent of an airline terminal: fuel, hangars, VIP lounges, ground handling, maintenance, concierge. Fuel alone is 50-70% of revenue. There are roughly 3,000 FBOs left in the U.S., down from 5,000 in the 1990s, and the top five chains now control 44% of the market. Mature FBOs run 20-30% operating margins.

Signature Aviation, the largest at 200-plus locations, was taken private in 2021 by Blackstone, Global Infrastructure Partners, and Bill Gates’s Cascade Investment for $4.73 billion.

The consolidation thesis is the same one that repriced self-storage and car washes: fragmented, operationally intensive, capital-constrained independents being rolled up by institutional platforms that can extract margin through scale. Except the supply can never grow. You can’t build a new airport.

Private hangars: A $10 billion bottleneck

In plain English, a personal home/garage for your jet (whereas FBOs are more like hotels.. a place to park your jet while you’re in town).

There is a massive need for these as 71% of U.S. general aviation airports maintain waitlists for hangar space. Teterboro, Van Nuys, and Miami Opa-Locka have three-year waits. Most existing hangars were built in the 1970s and ‘80s for smaller aircraft and can’t fit today’s Gulfstream G700s or Global 7500s. New hangars cost $60 to $200 per square foot to build depending on spec, and lease for $4,000 to $7,000 a month for larger jet spaces.

Sky Harbour Group, an aviation infrastructure company publicly traded on the NYSE (SKYH), operates roughly 1 million rentable square feet of hangar space with revenues growing +50% YoY and a development pipeline targeting 50-plus campuses and over 10 million square feet.

Hangar condos: The niche within the niche

High-net-worth pilots and charter operators are increasingly buying individual hangars on deeded or condominium ownership at airports. Pricing ranges from $300,000 for a basic box hangar to $1.5 million at Addison Airport in Dallas at roughly $460 per square foot.

Developer returns on hangar condo projects run 13-16% unlevered IRR. Some hangar locations have appreciated 400% over the past decade.

Fly-in communities: Residential meets runway

There are over 400 residential airparks in the United States where homeowners store aircraft in attached hangars and taxi to the runway from their driveway.

Spruce Creek in Florida is the largest: 1,300 homes, 5,000 residents, 700-plus hangars, and a 4,000-foot runway. Family homes run $400,000 to $2 million. At the high end, Alpine Airpark in Wyoming, 35 miles from Jackson Hole, sells lots for $479,000 to $2.25 million and finished homes for $3 to $5 million on a 5,850-foot runway. Pecan Plantation in Texas sold 174 lots in under three years, with transaction volume up 80% in 2025. Aviation homes sell at 20-30% premiums over comparable non-aviation properties.

MRO facilities: Aviation’s industrial play

Maintenance, Repair, and Overhaul facilities are the large-format industrial side of the ecosystem. The global MRO market is roughly $100 billion and growing at 5% annually. In 2023 alone, $8.5 billion was invested in new MRO facilities globally, with 14 new facilities in North America adding over 7 million square feet. ST Engineering is spending $210 million on an expansion in Pensacola. Construction costs run $120 to $220 per square foot, higher than standard industrial due to cranes, foam suppression systems, and specialty power requirements.

Luxury terminals: The new amenity race within FBOs

The latest wave of FBO investment is pushing the product toward hospitality.

Clay Lacy Aviation is spending over $100 million on a 14-acre, 145,000-square-foot complex at John Wayne Airport in Orange County.

Atlantic Aviation’s new Boca Raton terminal is a $40 million, four-story facility with hotel-inspired lounges.

Flexjet is building six new FBOs including a $36 million Scottsdale facility. SFO is developing a luxury private terminal where entry costs $895 to $5,000 per visit, driven in part by AI-sector wealth.

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Every corner of this ecosystem shares the same opportunity: the supply of airport land is fixed, the demand for private aviation is accelerating, and the infrastructure was built for a smaller era.

The operators and investors who control the tarmac over the next decade will set the terms for a very lucrative ecosystem.

I’ve always been romantically attached to the idea of being a farmer - working outside all day, no cell phone, living off the land, driving a tractor at 4 miles per hour and calling it “my commute”, etc.

Then I remember that actual farming involves no money, no vacations, no air conditioning, and a 4 AM alarm clock 365 days a year.

But my friend Darin Turner might have found the Goldilocks scenario: paulownia tree farming. Paulownia is a fast-growing (like almost invasive, 20-feet-in-the-first-year fast growing) species of hardwood that is light but strong and used in everything from boats to window frames to violins to surf boards.

Each tree generates roughly $860 in profit over an 8-10 year harvest cycle (vs. oak, maple, etc. that take 40) and regrow multiple times.

And the company Darin (who is the former CIO of Invesco) is building an institutional platform around, World Tree, has 8,000 acres of them planted across 375 farms in five countries.

I’m talking to Darin about it today at 3 PM ET (link here if you want to join live).

If you can’t make it, here’s the skinny

Timber has been one of the best-performing real asset classes for three decades. The NCREIF Timberland Index has delivered annualized returns above 8% with almost no correlation to equities or bonds. On paper, it’s the perfect portfolio diversifier: a physical asset that grows in value literally by growing, that doesn’t care about interest rates or earnings calls or what the Fed chair said on Tuesday.

And almost no private investors own it.

The reason is simple: most trees take forever to grow.

Traditional hardwood rotations for oak, maple, and walnut run 25 to 40 years. A family office that plants red oak today won’t see a harvest until the 2050s.

Meanwhile the institutional timber market is dominated by TIMOs and public REITs like Hancock and Weyerhaeuser that operate at that pace, with investment minimums in the tens of millions. The asset class has been structurally closed to private capital since it started outperforming.

Paulownia is a completely different animal.

The species grows 10 to 20 feet in its first year. It reaches harvestable size in 8 to 12 years. And after you cut it down, the root system regenerates and produces another harvestable tree, repeating for five to seven additional cycles without replanting. One planting produces decades of harvests. The hold period drops from “your grandchildren will thank you” to something that actually fits inside a fund life.

And it’s not a novelty wood. Paulownia is a genuine specialty hardwood, lighter than balsa but stronger than most softwoods, used in furniture, exterior siding, musical instruments, marine applications, and surfboards. It’s been a premium timber species in Japan for centuries.

The reason it hasn’t scaled commercially in the West is that nobody built the genetics program or the supply chain to do it until now.

World Tree has spent the last decade solving that problem.

They’ve developed proprietary genetics across 25 to 30 site-specific varieties, optimized for different climates and soil conditions. Their farms span Central America, the U.S., and Europe. First commercial lumber shipped in December 2025. The company is past the “is this real?” phase and into the “how do we scale this?” phase.

Which is why Darin is stepping in.

He spent nearly two decades at Invesco as CIO of Listed Real Assets - so he doesn’t usually gets excited about a tree unless the tree has a compelling risk-adjusted return profile.

His firm, Signal Line, is building the institutional-grade structuring and capital markets infrastructure to make paulownia timber investable at family office and private wealth scale for the first time. The goal is to take an asset class that has outperformed for 30 years and remove the two barriers that kept private capital out: the hold period and the access point.

The pitch, stripped down:

• an 8 to 12 year hold on a physical asset that literally grows,

• regenerates after harvest,

• produces a specialty product with established global demand,

• has three decades of index returns above 8 percent, and

• has zero correlation to the things keeping your LPs up at night.

And the downside is protected by the dirt and the timber on it. The upside is a function of biology.

I don’t know how many asset classes can make that claim.

Listen in today at 3 PM ET.

Mike Meldman, founder of Discovery Land, figured out the model thirty years ago with projects like Yellowstone Club, Baker’s Bay and Silo Ridge.

• Build a private residential community around a signature amenity, like golf courses or skiing

• Sell the homes

• Retain the club operations

• Collect initiation fees, annual dues, and management fees in perpetuity

Discovery Land now operates 35-plus communities worldwide, sells homes between $3 million and $50 million, charges $300,000 initiations and $40,000 in annual dues, and generates north of $2 billion in annual sales. Tom Brady and Reese Witherspoon are residents. And George Clooney co-founded a tequila brand with Meldman that sold to Diageo for a billion dollars.

Meldman proved that a branded residential community is not a real estate project — it’s a platform made up of real estate + brand + management.

Now a new generation of developers is importing his playbook into markets and price points Discovery Land couldn’t touch. The model is the same but the entry point is different; and for investors, the economics might actually be better.

The models are all a bit different, but generally work like this:

• A developer builds a branded community of 15 to 40 homes around a specific lifestyle: golf, outdoor adventure, desert weekends, ski access

• They sell a portion of the homes to lower their cost basis and recoup development capital

• The remaining homes stay in the portfolio as professionally managed short-term or mid-term rentals, generating cash flow at rates well above conventional residential

• The developer earns management fees on the entire community, both the homes they own and the homes they sold, covering everything from housekeeping and concierge to rental operations and maintenance.

For the homebuyer, the value proposition is equally clean: a beautiful home with resort-grade amenities in a rising market, professionally managed and cash-flowed as a rental when they’re not there, ideally covering the mortgage.

Three groups are executing versions of this right now, and each one takes a slightly different angle.

Teton Outing Club

Cardinal Lands is developing 30 luxury townhomes averaging 2,600 square feet on Ski Hill Road in Driggs, minutes from Grand Targhee and a short drive from Jackson Hole. Homes are priced 70% percent below comparable Jackson Hole properties.

The club is built around outdoor adventure: gear storage, a trip-planning library, recovery spaces, and a tradition of organized group outings punctuated by celebratory dinners.

Birdie Houses

Birdie Houses is building a portfolio of premium vacation rental homes in iconic golf destinations, each outfitted with amenities you’d find at a tour player’s private compound.

The flagship property in Pinehurst has a 6,000-square-foot short-game facility built by Celebrity Greens (the same team that built greens for Jon Rahm and Max Homa), an indoor simulator with Foresight launch monitors and PuttView augmented reality putting, Callaway wedges and Odyssey putters in every room, a sauna, cold plunge, humidor, and outdoor bar.

Polo Villas

Build to Stay — led by Jerry Coleman, the cofounder of Invitation Homes — is applying the institutional BTR playbook to vacation rentals.

Polo Villas is their first project: 18 custom luxury homes on half-acre lots adjacent to the Coachella festival grounds, each with five to seven bedrooms, pools, pickleball courts, putting greens, and outdoor kitchens. Villas rent for $1,450 to $1,650 per night on standard dates, with Coachella and Stagecoach weekends commanding significantly more.

Discovery Land proved it at the $10 million price point. These groups are proving it works at $500,000 to $2 million, in markets where the underlying real estate fundamentals are already accelerating.

When I was a kid in the ‘90s, my grandfather used to tell a story about three beachfront lots in Loveladies on Long Beach Island.

“It was the 1950s, right after a hurricane… a guy at the bar offered him all three lots for $10,000 each… he passed… those lots are worth millions today.”

I remember thinking he squandered the best real estate deal of all time. And then blamed him that we weren’t rich.

We all have those stories: the friend or uncle who almost bought in Montauk in the ‘80s, looked at Park City before the Olympics, Aspen when it was a mining town, yada yada.

The pattern is always the same: a place that was underbuilt, underknown, or had just been through something terrible. A catalyst arrived, and the window closed.

Here are six places where that window is still open.

Driggs, Idaho

The place. A ranch town in Teton Valley on the west side of the Tetons, ten miles from Grand Targhee Resort, which gets 500-plus inches of snow a year.

What makes it great. Fly fishing on the Teton River. Mountain biking. Yellowstone next door. A growing food and brewery scene. Targhee’s powder is consistently ranked among the best in the country.

What’s happening. Grand Targhee Resort is expanding: 50 new cabins, new lift infrastructure, new terrain. The average single-family home in Jackson Hole hit $10.7 million in 2024. Driggs median is $525,000 to $795,000. That’s one-sixth of Jackson. Teton County added 35% more jobs between 2017 and 2023, population up 14% in five years.

Sandpoint, Idaho

The place. A lakefront town on the shores of Lake Pend Oreille in northern Idaho, home to Schweitzer Mountain, the state’s largest ski resort at 2,900 acres.

What makes it great. Lake and mountain in the same town. Schweitzer has a 2,400-foot vertical drop. Downtown punches well above its weight in restaurants and breweries. Year-round recreation from skiing to wakeboarding.

What’s happening. Alterra acquired Schweitzer in 2023 and added it to the Ikon Pass. Every resort that joins Ikon sees a visitation spike. New chairlift already installed. Population up 29% since 2020. Median home around $450,000 to $589,000, correcting from pandemic highs. Sun Valley is $1M-plus.

Taos, New Mexico

The place. A high-desert arts town in the Sangre de Cristo Mountains, 70 miles north of Santa Fe, with a world-class ski area that averages 305 inches of snow.

What makes it great. One of the best art scenes in the American West. UNESCO World Heritage Taos Pueblo. New Mexican food people fly across the country for. Expert ski terrain with $300 million in renovations over the past decade.

What’s happening. A $5.4 million airport terminal is opening this month. JSX already flies direct to Dallas and Denver. The bottleneck in Taos has always been accessibility, not desirability, and that bottleneck is being removed. Median home around $599,000 versus Santa Fe at $750,000 to $900,000. Buyer’s market with 7.6 months of supply.

Gunnison, Colorado

The place. A university town 28 miles south of Crested Butte, sitting at the confluence of the Gunnison River and Blue Mesa Reservoir, Colorado’s largest body of water.

What makes it great. World-class fly fishing, backcountry skiing, mountain biking. Western State gives it year-round energy. Less precious than Crested Butte. More the kind of place where people actually live.

What’s happening. Crested Butte prices are roughly three times Gunnison’s. Condo and townhome prices in Gunnison have surged 73% as buyers shift south. The Driggs-to-Jackson dynamic, playing out in real time, 28 miles apart.

Gulf Shores, Alabama

The place. Thirty-two miles of white-sand Gulf Coast beach between Mobile Bay and the Florida Panhandle, anchored by Gulf Shores and Orange Beach.

What makes it great. The beaches are legitimately beautiful. Gulf State Park covers 6,150 acres. Deep-sea fishing charters leave daily. The seafood is better than most of the Panhandle. One of the few Gulf beaches where you can still buy for under $500,000.

Also home to my favorite bar in the world - Florabama.

What’s happening. Visitor spending hit $4.7 billion. Nearly 8 million visitors a year. A thousand new lodging units added in the last 18 months, another thousand coming. Median home is $458,000 to $515,000 versus 30A at $800,000 to $2 million. Vacation rentals average $43,700 a year.

Mexico Beach, Florida

The place. A small Gulf Coast town in the Florida Panhandle, halfway between Panama City Beach and Apalachicola.

What makes it great. Hurricane Michael leveled it in 2018 as a Category 5. The town has been rebuilt almost entirely from scratch: modern, elevated, storm-resilient homes on a stretch of Panhandle beach that feels like old Florida. No high-rises. No strip malls.

What’s happening. The housing stock is brand new. The prices reflect disaster recovery, not the quality of what’s been built. Median is $350,000 to $525,000 versus 30A at $800,000 to $2 million. That window closes once the last lot develops and the narrative shifts from “recovery” to “destination.” Insurance is a Panhandle-wide headwind, but this construction was built to current code.

I took a meeting last month with a member at Kith Ivy, Ronnie Fieg’s members-only padel and wellness club in the West Village. The initiation fee is $36,000, and then annual dues run another $7,000. The rooftop has three enclosed padel courts designed by Wilson with New York’s first Erewhon outpost on the ground floor. The spa is a partnership with Giorgio Armani, Café Mogador runs the restaurant, and then there’s a Kith retail shop, a gym, cold plunge pools, a hammam, and IV therapy rooms.

It was, objectively, a great place to take a meeting. And that sentence is the entire thesis of this letter.

The private members club market in the United States hit $5.39 billion in 2025, and club applications have increased 42 percent since 2021. New York has added more members clubs in the past three years than in the prior two decades.

But most of these clubs (Zero Bond, Aman, San Vicente, Casa Cipriani) are built primarily around food, beverage, and social programming. And F&B-driven members clubs are a brutal business with thin margins and tough to sustain differentiation. Once the opening buzz dies down, a club that offers dinner, drinks, and a nice room needs to give members a reason to come back three times a week, not three times a year. And most can’t.

Racquet sports solve that problem. And the participation numbers are no longer a niche trend.

• Tennis reached 27.3 million U.S. players in 2025, up 54 percent since 2019

• Pickleball hit 24.3 million, up 171 percent in three years, with the average player age dropping from 41 to 35

• Padel surpassed one million U.S. players in 2026 (up 250 percent since 2022), and more than 70 percent of new sports facilities built in 2024 included padel courts

And that’s just the mainstream layer. Squash, platform tennis, and the esoteric end of the spectrum (court tennis, rackets) round out a category where a single club can offer five or six sports under one roof.

None of this is new, of course.

The DNA of the American private club was athletic first and social second. The New York Athletic Club was founded in 1868. The Racquet and Tennis Club, purpose-built around court tennis and rackets, has occupied its McKim, Mead & White building on Park Avenue since 1918. The University Club, the Union League, the Harvard Club: racquet sports were the center of the club experience for a century.

Somewhere in the mid-twentieth century, the model shifted. The dining room became more important than the court. Soho House, Zero Bond, and the 2010s wave of social clubs were built almost entirely around F&B and curation, with fitness as an afterthought.

The racquet club renaissance is a return to the original model, updated for a generation that wants activity, wellness, and social connection in one membership.

And the economics favor it. Courts are cheap to build relative to the revenue they generate; a padel court runs $75,000 to $150,000, a fraction of a high-end restaurant buildout. The infrastructure drives repeat visits: a member who plays twice a week visits 100 times a year, versus 12 for a member who comes to dinner once a month.

Each visit is an opportunity for F&B, retail, and wellness spend. Courts don’t take up much real estate (three padel courts fit on a rooftop; squash courts stack vertically), which makes the model work in urban footprints where square footage is expensive.

And racquet sports are inherently social. Every game requires at least two people. Padel requires four. Nobody needs a programmed “mixer” when they’re already playing doubles with a potential client three times a week.

Kith Ivy is the most visible expression of the new model. Fieg understood that the padel courts are not the amenity; they’re the anchor. Everything else (the Erewhon tonic bar, the Armani spa, the restaurant, the retail shop) monetizes the foot traffic the courts generate.

• The $36,000 initiation fee is the membership; then

• The F&B, wellness, and retail revenue is the margin.

A new racquet club in South Florida sold its first 100 memberships in weeks with zero marketing spend and nearly 1,000 people on the interest list before opening. Life Time, which operates 115 clubs with 40 more planned, is adding racquet courts to every new location.

The risk, of course, is oversupply. When participation numbers grow this fast and capital follows, every secondary market will get three padel clubs before it needs one. And courts alone are not a moat. Courts plus hospitality-grade food, wellness, and brand might be. The operators who build generic court facilities without the club experience will struggle to justify premium memberships; the ones who understand that the court is the anchor and hospitality is the margin will build something durable.

The Gilded Age clubs understood this. People want a reason to show up. A court gives them one—and everything else follows from that.

Two friends of mine recently raised $20 million for a multifamily development deal. In this market, which—if you’ve tried to raise for ground-up multifamily recently—you know is about as fun as a root canal with no anesthesia.

They didn’t use a placement agent or tap large institutional capital. And they certainly didn’t rely on mass email blasts to a thousand investors.

I asked them what worked, and the answer was so obvious it was almost embarrassing.

They went deeper on relationships they already had.

They went to dinners, remembered kids’ names, texted articles that had nothing to do with the deal, congratulated people on things that weren’t fundraises, showed up at events and didn’t pitch, and followed up when they didn’t need anything.

They did the actual work of building relationships that no one seems to prioritize anymore.

Probably because most GPs I talk to treat capital raising like a top-of-funnel problem…

• Build a bigger list,

• Blast it,

• If someone doesn’t commit in 60 days, mark them as dead and move on.

The entire capital raising process today is optimized for volume, which is a polite way of saying most capital raising strategies have just become email marketing with a higher minimum check size.

Meanwhile, there are probably 200 people sitting in your CRM right now who already know you, already trust you, and already understand your strategy. Half of them said “not right now” on your last deal — which you interpreted as “not interested.” It almost certainly meant “not right now.” People have a lot going on… their kid is applying to college; they’re closing on a house; they just started a new role; etc. Your $5 million capital call was not top of mind that particular Tuesday in March.

The problem is that maintaining 200 relationships at any real depth is a full-time job, and capital raising already sits on the most senior, most time-constrained person at the firm. So the quarterly update goes out, three people reply, and the rest slowly forget you exist. Not because the relationship soured, but because nobody watered it.

This is where AI gets interesting — and I don’t mean using it to write faster cold emails to bigger lists. That’s just spam with better grammar and a LinkedIn thought leader telling you it’s “scale.”

The real unlock is using AI to watch the people you already know and surface moments worth acting on.

Your investors are not just rows in a CRM. They’re people generating signals constantly across every public channel they touch — LinkedIn, Instagram, Facebook, their firm’s website, Google News, SEC filings.

• An investor’s firm just closed a new fund

• Someone you pitched last year just got promoted to head of real assets at a family office

• A contact just posted vacation photos from Nashville, where you happen to have a project under construction

👆 These are the opening lines of real conversations. And they produce outreach that actually deepens a relationship — not “just checking in” or “wanted to circle back,” which are both shorthand for “I have nothing specific to say but my CRM told me to email you.”

The relationship building workflows we’re building with a few groups right now looks like this.

1. You take your existing investor universe — everyone who’s ever taken a call — and build signal monitors across their public channels.

2. AI watches all of it, continuously, and surfaces relevant moments as signals.

3. AI drafts the follow-up — specific, short note tied to that signal, written in the GP’s voice and calibrated to the relationship.

4. The GP reviews it, tweaks it if needed, and hits send.

Thirty seconds instead of thirty minutes, which means it actually happens instead of aging on a to-do list.

The playbook looks more like what a great consumer brand does than what a traditional capital markets team does. The best DTC companies track customer behavior across every touchpoint and reach out at exactly the right moment with exactly the right message.

Investors are consumers too. They have social media accounts and life events and interests that extend well beyond their allocation mandate. The information is all public. Almost nobody in real estate is systematically using it.

The line between thoughtful and creepy is the senior person’s judgment (which is why the human stays in the loop). AI surfaces the signal; then the GP decides whether to act on it. That human filter is what keeps it personal instead of algorithmic, and it’s why this only works when the workflow is built around how a specific person actually operates, not jammed into some off-the-shelf sequence.

My friends who raised that $20 million didn’t use any of this technology. They did it the old-fashioned way — remembering details, checking in on people, showing up. It works because it’s genuine. What we’re building is the infrastructure to do that at scale without losing the part that made it work in the first place.

The biggest opportunity in capital raising right now isn’t finding new investors. It’s going deeper with the ones who already know your name.

I had coffee last month with a marina operator I’ll call “James”. He runs twelve marinas across the Northeast — roughly 4,000 slips, a fuel operation, a handful of dry storage facilities, and a boat service business he bolted on two years ago. Total AUM is somewhere around $180 million.

James doesn’t have a fund and has never raised institutional capital. His investor base is a patchwork of family offices, a few HNW individuals he met through a friend’s friend, and his own balance sheet. He operates every asset himself — dealing with the Army Corps of Engineers when a dock permit stalls, negotiating fuel margins with distributors, fielding a call at 6 AM when a storm rips a dock off its pilings in Fort Lauderdale.

He’s also generating a net yield his investors can’t find anywhere else.

His portfolio averages north of a 9% cash-on-cash return, in an asset class where Blackstone paid $5.65 billion for Safe Harbor Marinas and Bain Capital is rolling up slips on the East Coast at compressed cap rates. James beats them on yield because he

• Stays small,

• Operates with intensity, and

• Knows every slip in his portfolio by name.

He doesn’t need to hit a $5 billion fund target. He needs to find the next off-market marina on the Gulf Coast before a consolidator does.

James is an archetype. And he’s everywhere.

The operator nobody is writing about

There are hundreds of operators like James building portfolios in asset classes that didn’t have names ten years ago — outdoor hospitality, cold storage, small bay industrial, surf parks, branded residential, RV parks, industrial outdoor storage. They run somewhere between $50 million and $300 million in AUM. Small teams, five to twenty people. Operationally obsessive in a way that would be unrecognizable to someone managing a stabilized Class A multifamily portfolio.

What makes them different from the last generation of real estate entrepreneurs is how they got here. James didn’t start by raising a fund and then going looking for marinas. He started by operating one marina and learning the business from the inside. The portfolio grew because he got good at operations, not because he got good at pitching LPs.

Most institutional real estate businesses are built the other way around — the capital comes first, the operating capability gets figured out later.

And it’s the reason James can generate the returns he does. His returns aren’t good despite his small scale… they’re good because of it.

He sources off-market. He operates with a cost structure that a 200-marina platform can’t touch. He makes decisions in hours that a corporate operator routes through three committees over six weeks. The moment you institutionalize the portfolio — add the IR team, the fund admin, the quarterly reporting — you add cost, slow down decision-making, and compress the very returns that made the investment attractive in the first place.

And the operational complexity of his asset class is what protects all of this. Marinas aren’t apartments. You can’t underwrite them on a rent roll and a cap rate. There’s a fuel business, a service business, a slip rental business, a dry storage business, and a retail operation — all running simultaneously on the same waterfront property, all subject to weather, permitting, environmental regulation, and seasonal demand. That complexity keeps the passive capital out. It rewards the people who actually understand the business — and it punishes the ones who don’t.

James also isn’t just buying buildings. He’s built a marina operating company with proprietary vendor relationships, fuel purchasing agreements, dock maintenance protocols, and a reputation on the Gulf Coast that makes every new acquisition easier than the last one. The operating company has value that exists apart from the real estate.

The capital problem

The infrastructure of real estate capital markets was not built for someone like James.

Placement agents won’t touch a $30 million raise — the economics don’t work for them. They need $200 million-plus to justify the effort. The conference circuit is designed for institutional sponsors with glossy pitch decks and five-person IR teams. The LP databases filter by AUM, track record length, and fund size, and James gets screened out of all three.

The capital that would actually be a good fit — family offices, HNW individuals, small RIAs — can’t find him. There’s no directory of marina operators generating 9% cash yields. There’s no placement agent connecting a family office in Dallas with a twelve-marina portfolio in Naples, Florida. These matches happen, when they happen at all, through personal networks and luck.

So you end up with a market that’s broken in both directions. Operators with strong businesses and real yields can’t raise. Investors with the right appetite and time horizon are stuck choosing between institutional funds that are too big and too expensive, or direct deals they stumbled into with no infrastructure around them.

Private wealth and the $50M Operator

Family offices now put somewhere between 45% and 55% of their portfolios into alternatives, up from about 30% a decade ago. They’re making opportunistic bets on real estate while a lot of institutional capital sits on the sidelines. And they’re far more willing to explore asset classes that pension funds won’t look at — because the check sizes are too small, the sectors are too weird, or the operators are too early.

The $50M Operator is, in a lot of ways, exactly what this capital is looking for.

A family office can write a $2 million check into James’s next marina acquisition. That check is meaningful for him and irrelevant for a $500 million fund. Family office capital doesn’t need quarterly liquidity or a J-curve narrative for an investment committee. It can back an operator for a decade and compound alongside the business, which is what James actually needs — not a three-year hold with an IRR bogey.

And the yield spread is enormous. Institutional real estate in 2026 is generating mid-single digits. James is north of 9%, and operators in other niche asset classes are doing similar numbers. That spread exists specifically because these operators haven’t scaled past the point where their operational edge gets diluted by corporate overhead. The premium is the boutique.

A family office that backs five or six of these operators across marinas, outdoor hospitality, cold storage, and small bay industrial has built a portfolio of high-yielding, uncorrelated real estate exposure that no institutional fund in the market can replicate.

I think this is where private wealth real estate investing is heading. Not blind pool funds. Not REITs. Curated exposure to the operators generating real alpha in the most operationally complex corners of the market.

What could go wrong

When you invest with a $50M Operator, you’re betting on a person. If James gets hit by a bus, the portfolio has a problem that a Blackstone-owned platform would not. That key-person risk is real, and institutional investors have spent decades engineering it out of their portfolios for a reason.

There’s also the growth trap. At some point, James needs a real back office — a CFO, a head of IR, a fund administrator. Those hires cost money and add complexity, and they start to erode the characteristics that made the business attractive. The operators who navigate this well will be the ones who professionalize their infrastructure without professionalizing their operations — who build the back office without losing the 6 AM phone call.

And then there’s the problem of actually finding these people. The $50M Operator is, almost by definition, invisible. No PR team. No PERE conference presence. No database listing. You find them through niche media, operator communities, word of mouth, and the kind of ground-level market intelligence that most investors don’t have and aren’t set up to get.

The investable middle

I wrote a few months ago about the K-shaped economy hollowing out the middle of real estate — the $300 hotel room, the Class B office, the aspirational-luxury condo. The middle is dying in those categories because it lost its reason to exist.

But there’s another middle in real estate that’s doing the opposite. The $50M Operator occupies a middle between institutional platforms and individual deal sponsors, and that middle is thriving precisely because it’s hard. The operational complexity, the small scale, the niche asset classes — these aren’t bugs. They’re the reason the returns are there.

For most of these operators, staying between $50 million and $300 million in AUM isn’t a phase. It’s the strategy. The boutique is the alpha. The yield premium disappears the moment you try to scale past the operator’s edge.

The operators are already here, building real businesses in asset classes the rest of the market is still trying to name. The capital is looking for them. The infrastructure to connect the two is what’s missing — and what’s being built right now, one marina at a time.

Four years ago, I launched a real estate investment banking boutique. The thesis was simple: there are hundreds of innovative real estate operating companies building in niche asset classes—data centers, outdoor hospitality, senior living, cold storage—and most of them are too small or too unconventional for the big banks to care about. Someone should help them raise capital.

The business model was the same one every capital raiser runs:

• Get a client;

• Use their deal as bait to get meetings with investors;

• Learn what those investors want;

• Use that knowledge to get the next client;

• Repeat.

The product, really, was a Rolodex—and the only way to build it was through a steady stream of dinners, conferences, and cold emails.

It worked, slowly.

And five years in, I can look back at a series of assumptions I held on day one that turned out to be wrong — or at least incomplete. Each time I updated one of those assumptions, we ended up building something new.

What started as a traditional advisory business has become something I didn’t plan for and am still figuring out: a platform that combines media, data, AI, and live events to connect real estate operators with capital.

I want to walk through what I got wrong, what we built as a result, and where it’s going.

“Capital raising is a relationship business.”

This is the thing everyone says. And it’s true—but it’s an incomplete truth that leads to a bad strategy.

Yes, an investor is more likely to take a call from someone they know and trust. But the traditional version of “relationship-driven capital raising” means a senior person manually working a network of a few hundred contacts, built over decades, maintained through dinners and conferences. The knowledge about what those investors want lives in that person’s head. When they leave, the Rolodex leaves with them.

I spent my first two years doing exactly this: flying to conferences; hosting dinners; and getting introduced to one LP at a time. And it struck me that the bottleneck wasn’t the quality of our deals or the caliber of the operators we worked with. The bottleneck was that I could only build relationships at the speed of one human being’s calendar.

The assumption I should have started with: capital raising is a trust business, and relationships are just one way to build trust. Content is another.

That realization led us to start using Thesis Driven—a media company my partner Brad Hargreaves had already built into one of the most-read real estate publications in the country—as a capital markets tool.

We started writing about the asset classes and themes our operators were building in.

We published deep dives on niche sectors, interviewed operators on camera.

We hosted virtual events where investors could hear directly from founders.

The investors came to us. Not because we pitched them, but because they’d been reading us for months and already trusted the perspective. Media turned out to be the best investor acquisition channel in real estate—and almost nobody is using it that way.

“Data is a back-office function.”

When we started taking investor meetings—dozens, then hundreds—I kept a spreadsheet:

• what asset classes each investor liked…

• check sizes…

• preferred structures…

• geographic focus…

• notes from every call.

It was useful but messy. And I realized pretty quickly that the intelligence we were collecting was more valuable than I’d understood. Every investor conversation was a data point: what’s getting allocated to, what’s out of favor, where the capital is flowing. Individually, each call is just a call. In aggregate, it’s a live map of private real estate capital markets.

So we built a platform to capture and structure all of it. Every investor conversation gets logged. Mandates, preferences, deal history, and relationship maps are all tracked. We now have structured intelligence on thousands of institutional investors, family offices, and RIAs — not scraped from the internet, but gathered from real conversations over years.

What I got wrong was thinking of this as an internal tool. The data layer turned out to be the connective tissue of the entire business—the thing that makes every other piece work better. It powers our advisory engagements, informs our media coverage, and increasingly, it’s a product in its own right for operators who want to understand the investor landscape before they start raising in CapitalStack.

“AI will just make outreach faster.”

When AI tools started getting good enough to draft real prose, the obvious application was email. Build a list, generate personalized outreach, send at scale. And that’s what most people in capital raising are doing with AI right now — producing faster, more efficient spam.

I almost made this mistake.

The instinct is to take the most tedious part of the job (writing 200 investor emails) and automate it. But automating a bad process just produces bad output faster.

The real unlock wasn’t speed; it was matching.

We’ve now brought in a machine learning engineer to build workflows that sit on top of our investor dataset. The system doesn’t just draft emails—it starts upstream.

• Which investors in our universe have a mandate that fits this deal?

• Which ones have done something similar in the last 18 months?

• Who in our network has a warm path to the decision-maker?

• How should the pitch be framed differently for a pension fund allocator versus a family office principal?

By the time a message gets written, the AI has already done the work that used to take a senior person days: prospect research, relationship mapping, pitch calibration.

The senior leader stays in control of the message and the relationship, but the grunt work (the thing that made in-house investor outreach impractical for most operators) disappears.

Done right, AI doesn’t make outreach faster. It makes outreach smarter—and keeps the senior leader in the driver’s seat. Done wrong, it’s just a more efficient way to erode the trust you spent years building. The difference is whether you start with data and judgment or start with a template and a send button.

“You can do all of this from behind a screen.”

This is the one I keep relearning.

Media scales… data compounds… AI workflows collapse manual labor…. but, none of it replaces what happens when you put an operator and an investor in the same room.

So we’re building out a live events program—starting with a Capital Markets Summit this summer—designed to do exactly that. Not a generic industry conference with 2,000 people and a trade show floor, but a curated room where the operators we work with meet the investors we’ve identified as genuine fits, with enough shared context that the conversations skip the preamble and get to substance.

The events are the part of the business that doesn’t scale. But they’re where trust gets built in a way that no email, article, or dataset can replicate. And they’re the reason the rest of the stack exists — everything else is designed to make that room as productive as possible.

The stack

When I zoom out, what we’ve built is four layers that feed each other:

Media creates the top of the funnel—operators and investors find us through the writing, the events, and the research. It builds trust at scale in a way that cold outreach never will.

Data captures the intelligence from every conversation and structures it into a living map of who’s investing in what, at what size, and through what structures.

AI workflows sit on top of the data and collapse the manual work of investor discovery, matching, and outreach.

Live events bring it all together in a room, with context, where real relationships start.

Each layer makes the others more valuable.

• The media drives the conversations that feed the data →

• The data powers the AI workflows →

• The AI workflows make the events more targeted →

• The events generate the relationships that become the next round of intelligence.

I certainly didn’t plan this. Five years ago, I thought I was building an advisory business with a Rolodex.

What we’re actually building is an ecosystem designed to connect the operators innovating across the built world with the capital to do it—using tools that didn’t exist when we started.

What’s next

We’re still early. The AI workflows are in pilot; the events program is just getting started; and the data platform is good but not where it needs to be. I share all of this not because we’ve figured it out, but because I think the model is right—and I want to build it in the open.

If you’re an operator raising capital in a niche or innovative corner of real estate, or an investor trying to find them, this is what we’re working on.

We’re grateful to everyone who’s been part of the journey so far—the operators who trusted us early, the investors who took our calls, and the readers who’ve been following along. You’ve shaped every part of this more than you know.

More to come,

I just got back from a surf trip to Nicaragua. The trip starts the way most of these trips start: landing somewhere that doesn’t feel like a vacation destination (in this case, Managua Airport); navigating what feels like an illegal rental car experience; and driving through farms where dogs and cows wander onto the highway. I sat stalled for thirty minutes behind a funeral, a casket in the bed of a pickup truck, with a village walking behind it.

By the time the coast appears, the airport feels like another country. There are no resorts, just beaches and cliffs, locals surfing the same breaks they’ve surfed for generations, beachfront bars with dollar beers, and bonfires at night. Each morning I took a boat in the dark to a break nobody’s named on a map, with a few people nobody knew the day before, and surfed for five hours. Came back, ate lunch, surfed again. In bed by 8 PM with a tuna burger, four Toña beers, and the deep, animal exhaustion of a body that did something all day.

The next morning, it happens again.

These trips - whether hunting, fishing, surfing, backcountry skiing - share a set of ingredients that no luxury hotel can replicate:

• Shared physical pursuit that’s adventurous and sometimes (slightly) dangerous,

• Remote location that takes real effort to reach,

• Forced disconnection by geography rather than virtue,

• Immersion in a local economy that is set in nature, and

• A small, self-selected group of people who become close (because the format forces it).

They also share something else. They’re almost impossible to find online. The best spots have minimal internet presence with sparse lodging and a local service infrastructure - where nothing is branded. Most of them get booked through a friend who heard about them from someone they met on a previous trip.

They cost a fraction of what most “luxury” travel costs. And the wealthier my friends get, the more they prefer them to anything a Four Seasons could offer.

The Missing Brand

A few operators have tried to institutionalize this.

• Eleven Experience, founded by former Blackstone real estate executive Chad Pike, runs roughly a dozen properties globally focused on heli-skiing, surfing, fishing, and other adventure pursuits, with week-long programs north of $10K per night

• Venator is positioning itself as a high-end branded experience for affluent hunters

• Explora pioneered the luxury adventure lodge model in Patagonia more than two decades ago

• Singita built one of the most respected luxury brands in the world by mastering the African safari

Each is a niche within a niche, and the aggregate market remains fragmented. The dominant adventure travel brand, the “Aman” or “Six Senses” of extreme outdoor experiences, doesn’t exist.

It should, in theory.

The adventure travel industry is worth over $700 billion globally. HNW and UHNW populations are growing faster than at any point in modern history. And the most thoughtful wealthy travelers are quietly bored of the conventional luxury product; the six-star resort has become a commodity. The Maldives overwater bungalow is fungible across thirty different brands. A truly memorable experience requires something more than a butler and a tasting menu.

The demand is there, and so is the capital. What’s missing is the brand.

What the Right Brand Might Look Like

A small portfolio of owned or partner properties in the world’s best spots for specific sports:

• Experiences built around the experience infrastructure: surf breaks in Indonesia, Nicaragua, and the Mentawais; heli-ski terrain in British Columbia, Alaska, and Japan; fishing in Argentina, Iceland, and Kamchatka

• A guide network hired locally and paid well, because the people who make these trips great are local operators, not corporate transplants

• A community model rather than a hotel model, built around repeat guests and a shared culture of seriousness about the sport

• Lodging that’s elevated but not sterile: a beautifully built hunting lodge or surf camp, not a Four Seasons dropped onto a remote coastline

• A digital experience that’s intentionally minimal, because the value of the brand is what happens once the phone goes away.

The economics could work: ultra-low-volume, high-margin, deeply differentiated. The brand becomes a status object… not because it’s expensive but because it’s hard to access and the experience is genuine.

The Counterargument

But there’s a real argument that this whole thesis is wrong.

The thing that makes these trips great is precisely the absence of brand: the lack of polish, the local guide who isn’t on a corporate org chart, the dollar beer at the unmarked bar, the fact that nobody is monetizing the experience beyond a fair price for honest labor. The moment a luxury brand wraps itself around all of this, something essential gets lost. The community of serious surfers gets replaced by people who heard the brand was cool, the local guides get squeezed out, and the bonfire becomes a “fireside experience” for Instagram.

Maybe these trips are great precisely because they refuse to scale. The scarcity, the cheapness, and the lack of monetization are core the amenity. They keep the people who don’t really want to be there from showing up and preserve the culture that makes the trip worth taking.

If someone does build the great adventure travel brand, the hardest part won’t be raising capital or finding properties. It will be designing a business that grows just enough to sustain itself, and then refuses to grow any more.

That’s probably not a venture-backable business. But it might be the only version of this category worth building.

Elon Musk wants to put a million data centers in space.

Three months ago, SpaceX filed with the FCC for permission to launch up to one million satellites into orbit. Not for internet access (Starlink handles that)—for computing. These are solar-powered orbital data centers that process AI workloads in space, where energy is unlimited and cooling is free.

Around the same time, Musk proposed merging SpaceX with xAI in a deal valuing the combined entity at roughly $1.25 trillion. Then he outlined plans to build a a factory on the Moon to manufacture AI satellites and launch them into orbit using an electromagnetic catapult, leveraging the Moon’s one-sixth gravity and zero atmosphere to fling hardware into space at a fraction of the cost of a rocket.

He calls the vision a “sentient sun.”

I read all of this and realized I didn’t actually understand data centers well enough to know whether it was genius or insane. So I went down the rabbit hole.

What a data center actually is

Every text you send, show you stream, and question you ask Claude happens inside a building somewhere. A data center is essentially a warehouse full of servers that store, process, and transmit data. It’s to the internet what a power plant is to your light switch.

There are more than 10,000 data centers in the United States, ranging from edge facilities the size of a shipping container to hyperscale campuses covering millions of square feet at $1B+ per build. The tenants: Microsoft, Google, Amazon, Meta, Apple, Oracle, plus enterprise customers like banks, hospitals, and AI startups that lease smaller blocks from colocation providers.

The real estate model

At their core, data centers are a real estate business. Developers acquire land, build a facility, and lease to tenants on 10-to-20 year triple-net contracts. The economics look more like industrial net lease than office or retail.

The critical variable is power, not necessarily location. A hyperscale facility needs 100 to 300 MW, enough to run a small city. Securing that power from the local utility, often years in advance, is the single most important step. This is why data centers cluster in Northern Virginia (the data center capital of the world), Dallas, Phoenix, and Chicago, and increasingly in smaller markets where cheap power remains available.

The cocktail party insight: training vs. inference

AI models need to be trained, feeding trillions of data points into GPU clusters in a massively energy-intensive process. That’s what the current buildout is primarily serving.

Then there’s inference—every time you or I actually use the model. Every AI response, image generated, and voice assistant answer uses less power per query, but the volume is astronomical and growing exponentially.

Training is building the factory, and inference is running it 24/7. Some believe advances in model efficiency and chip design will dramatically reduce inference energy costs over time—which would reshape the infrastructure buildout. Others argue the sheer volume of queries will outpace any efficiency gains. Either way, the long-term investment thesis is focused on inference because that’s where the recurring, always-on demand lives.

How to invest

Four access points:

• Public REITs: Equinix and Digital Realty are the dominant publicly traded data center REITs. Equinix operates 260+ facilities across 70+ metros globally. The challenge: they’ve already priced in a lot of the AI tailwind.

• Private infrastructure funds: Brookfield, KKR, and Blackstone have raised massive funds to build and acquire data centers. Institutional scale, long time horizons, large minimums.

• Niche operators: This is where it gets interesting for the Buy Box audience. Companies like Karis — featured at our recent Niche Industrial Pitch Night — acquire powered land and data center sites with 500+ MW of committed capacity across 2,800 entitled acres. The play: source the land and the power before the hyperscalers arrive.

• Adjacencies: Power generation (especially renewables), cooling technology, fiber networks, and the construction firms building these facilities.

Why does Musk want to put data centers in orbit? Two words: power and cooling.

On Earth, data centers are hitting a hard wall; they consume more electricity than many countries, utilities can’t keep up with demand, and new power generation takes a decade to permit and build. Water for cooling is increasingly scarce. Every new hyperscale facility is a fight with local utilities, regulators, and communities.

In space, the sun never stops shining, solar panels generate energy 24 hours a day with no weather interruptions and the vacuum of space provides natural cooling without water or chillers.

Is it feasible? SpaceX itself warned investors last week that the plan “may never become commercially viable.” The technical hurdles — latency, maintenance, data transmission, and the physics of putting a million objects in orbit — are enormous.

But here’s what I take away as an investor: even if orbital data centers are a decade away or never arrive, the fact that the most ambitious company on the planet is trying to solve this problem from space tells you everything about how severe the terrestrial constraints have become.

I get 10+ emails a week from college students asking for an internship. They all start with a paragraph about how much they admire our company (a company they clearly know nothing about, see above), followed by a PDF resume with a polite request to “learn from the best.”

Every one was written by ChatGPT (I can tell because they all use “moreover”)

As far as I can tell, the goal is to get an internship that pads a resume that gets them a soul-sucking real estate IB analyst seat that they’ll leave in two years. It’s the most expensive, least efficient path to a real estate career I can imagine. And I know, because I basically did a version of it.

Here’s how I got into real estate.

I was dating someone in college whose dad was a developer. I watched him build things and get paid a lot of money for it. That was the spark.

So what did I do with that spark? Absolutely nothing strategic.

I didn’t study real estate or learn to model. I didn’t read a zoning code. I basically just told people “I want to work in real estate” and waited for nepotism to run its course.

My friend’s dad got me a summer internship in brokerage and I got a full-time job off the back of it. I hated it. So I went to law school. I hated that too. Then I finally realized what I should have figured out on day one: I just needed to start putting small deals together myself.

It took me seven years and about $200k in law school debt to arrive at a conclusion I could have reached at 20 with a laptop and some initiative.

If I were 20 years old today—with access to Claude, the internet, and social media—here’s what I’d do instead of blasting cold emails or relying on nepotism.

Step 1: Build a curriculum with AI

Open Claude and design an independent study covering four things:

1. which real estate asset classes are most likely to be impacted by AI over the next decade;

2. the core development skills (financial modeling, zoning analysis, lease structuring, construction budgeting) and how to learn each one using AI-enabled tools;

3. how real estate capital markets actually work—who the LPs are, how funds are structured, how deals get financed; and

4. hands-on case studies where I underwrite real local projects, build business plans, and pressure-test assumptions.

I wouldn’t wait for a professor to assign this. I’d build it myself, then walk it into the office of the most entrepreneurial professor in my business school and say: “I built this. Will you sponsor it as an independent study and help me find a local developer to apprentice with?”

Step 2: Find a 4-plex

While doing the independent study, I’d find a small multifamily property… probably a 4-plex, a duplex, something achievable… and underwrite it. Then run the model, walk the property, talk to the city about zoning, get a broker’s opinion of value, and build a real business plan—not a classroom exercise.

The goal wouldn’t be to “get an A”… but actually do the deal.

Step 3: Document everything on social media

From day one, I’d post about what I’m learning… not necessarily polished thought leadership… just honest, raw documentation of a 20-year-old trying to figure out real estate in real time. Every week I’d share what I read, modeled, got wrong and what surprised me.

This would do two things.

First, it would build an audience of people who are rooting for me—from other students to real estate executives (I’d watch this all day long) to investors who find my curiosity and transparency compelling.

Second, it would create a founder-led brand before I’d even done my first deal. By the time I’m ready to buy that 4-plex, people already know me.

Step 4: Crowdfund the 4-plex

(This is the part that would have been impossible in 2007 and is entirely possible in 2026) I’d have spent months building an audience; documenting my learning publicly; and have built a real business plan on a real property. Now I would go to that audience and raise the few hundred thousand dollars to close the deal.

Step 5: Decide what’s next

By the end of 24 months, I’d have something that almost no 22-year-old in real estate has: a real deal, a real track record (even if it’s small), a public body of work that demonstrates how I think, and an audience that’s been following my journey from the beginning.

I could join an existing platform with credibility, or keep doing small deals and build my own portfolio.

Personally, I’d probably go try to take down a mobile home park.

There’s a simple test for whether a real estate investment will make you money: try describing it at a dinner party. If people’s eyes glaze over, you’re probably onto something. If they lean in and ask follow-up questions, you’re probably overpaying.

If I were building a real estate portfolio from scratch today, I’d have one goal: maximum risk-adjusted return with minimum downside. The result would be the most boring portfolio you’ve ever seen. Not a single trophy tower, luxury condo, or boutique hotel—just five unglamorous asset classes that everybody should own.

Here’s the ranking, from 5 to 1.

#5: Express Car Washes

Nobody has ever walked into a cocktail party and said “let me tell you about my car wash portfolio,” which is why the economics are so good.

Express car washes run on a subscription model—$25–$40/month for unlimited washes—creating recurring revenue that looks more like SaaS than real estate. Labor is minimal, throughput is high (150+ cars per hour), and gross margins regularly exceed 80%.

Private equity has been consolidating this sector aggressively (Mister Car Wash, Driven Brands, Whistle Express), while the fragmented independent landscape is enormous.

Best markets are Sun Belt suburbs with high car ownership and weather that doesn’t shut you down five months a year.

#4: RV Parks & Campgrounds

The budget end of outdoor hospitality (not glamping) has the economics of self-storage with the demand tailwinds of the experiential economy, and almost nobody is underwriting it.

There are roughly 27,000 campgrounds in the U.S., and the vast majority are family-owned and operationally unsophisticated. That’s exactly what self-storage looked like before Public Storage and Extra Space rolled up the market.

You own the land, tenants bring their own assets, capex is minimal, and occupancy in well-located parks runs 85–95%. Mom-and-pop parks trade at 7-9 caps and can be repositioned to 5-6 caps through professional management.

Outdoor recreation demand is structural, supply is constrained (try permitting a new RV park near a national park), and the consolidation runway is massive.

#3: Manufactured Housing Communities

Say “trailer park” among your friends and watch the room recoil. Say “manufactured housing community” to an institutional investor and watch them write a check.

That disconnect = opportunity.

You own the land, residents own their homes. Capex for the landlord is nearly zero. Residents pay $300-$700/month in lot rent and almost never leave because relocating a manufactured home costs $5,000 to $10,000.

Turnover is under 5% annually, compared to 50%+ in conventional apartments.

Manufactured housing is the largest source of unsubsidized affordable housing in America, serving a growing demographic that has nowhere else to go. And supply is permanently constrained: most municipalities have made it effectively impossible to permit a new community.

Sam Zell figured this out decades ago. The private market is still catching up.

#2: Small-Bay Industrial / Flex

This is the asset class I’m most excited about right now.

Small-bay industrial is the 1,500-5,000 square foot flex/warehouse unit leased to contractors, tradespeople, and small businesses: The HVAC company that needs a bay for trucks and parts, or the electrician who needs a shop with a roll-up door.

These tenants are the backbone of every local economy, and nobody is building for them.

New industrial development has overwhelmingly focused on big-box logistics: 200,000+ SF distribution centers. Small-bay has been ignored, which means supply is frozen while demand grows.

Rents are climbing 8-12% annually with virtually no new competition. Vacancy in well-located facilities is often below 3%. And the operational complexity is a real moat: you’re managing 30-50 tenants instead of one, which keeps institutional capital out and prices low for operators who can handle it.

#1: Self-Storage

The king of boring.

Self-storage has quietly outperformed every major real estate asset class over the past 25 years, and the opportunity is still enormous.

Stabilized facilities run at 90%+ occupancy with 70-80% operating margins, minimal capex, and recession-resistant demand. Customers stay an average of 14 months despite intending to stay for three: once your stuff is in a unit, inertia takes over.

There are roughly 60,000 facilities in the U.S. and the top six operators control only about 20% of the market. The remaining 80% is independently owned, often by families running a facility without a website, dynamic pricing, or professional management.

This is the single largest consolidation opportunity in commercial real estate. The operators we work with are proving that niche positioning within self-storage generates outsized returns. Many deliver a +30% revenue increase in year one by simply professionalizing operations that hadn’t been touched in decades.

Self-storage is the best boring real estate investment and may also be the best risk-adjusted investment in all of real estate.

So if you’re looking at this list and thinking “none of these are exciting,” that’s the point.