🗞️ News & Moves 🏠

A self-storage REIT arrived at Wall Street with a big ask. (Bloomberg) 

SmartStop Self Storage is trying to squeeze $972M out of Wall Street.

The L.A.-based REIT wants to unload 27M shares at $28–$36 apiece in an NYSE debut, giving it a $1.8B valuation if it hits the top.

Timing is bold, too—IPOs have been sleepwalking this year.

But with 208 locations across the U.S. and Canada, SmartStop’s betting that America still loves to hoard.

Investors expect the shares to trade on the New York Stock Exchange under the symbol “SMA.””

Let’s see if Wall Street has got room for another storage play.

Office-to-resi was hot—now it’s burning some developers alive. (Real Deal For You)

Turning offices into homes seemed like the next big trend.

But some developers face tough reality and rising rates.

Brandon Chasen bet big on Baltimore’s office-to-resi gold rush.

Now he’s drowning in lawsuits, and creditors are chasing his Gulfstream.

His showpiece project?

One Calvert Plaza.

Busted.

Over budget.

Unrealistic pro forma.

He’s not alone.

Developers in San Francisco, DC, Chicago, and NYC are also defaulting.

They’re handing back keys or facing foreclosure.

Turns out, converting ghost offices into apartments ain’t plug-and-play.

Rising rates, stubborn tenants, and blocked views are turning a smart investment into a money pit.

Lesson?

Just because an office is empty doesn’t mean it’s easy to convert.

🚨 The Fed Pulse 🚨

Uncertainty is high—but so is resilience.

As April 2 approaches and new auto tariffs loom, the headlines feel chaotic.

But beneath the noise, the U.S. economy is still pushing forward.

BMW decided to absorb most of the 25% tariff, raising prices by 4%.

Economic and trade policy uncertainty indexes are rising.

We haven't seen levels like this since 2008 and early COVID.

Despite the noise, capital goods orders remain steady.

Leading indicators suggest growth for 2025.

The Fed held rates steady in March and still sees two cuts ahead.

Inflation expectations increased to 2.7% as a result of tariffs.

Sunday morning perception bender for ya!

Five years ago, I met Shay Yakobovich (Facebook).

Sharp.

Thoughtful, high-integrity commercial real estate investor.

We connected well and ended up doing a small deal together that we still own.

He was living in Miami at the time and actively building his portfolio.

Fast forward to today—I get a WhatsApp message from him.

It’s a photo.

Infinity pool.

Laptop open.

A jungle in the background, ocean peeking out in the distance.

“This was my office today,” he texts.

He’s in Thailand.

And no, he’s not on vacation.

This is his life.

Shay is what happens when someone says enough—and means it.

Enough investor updates.

Enough capital raising.

Enough chasing a bigger number on a spreadsheet.

He lives in Thailand now.

Wakes up with no plan.

CrossFit in the morning.

Beach by afternoon.

Massage.

Dinner with friends.

Maybe work four hours a week, max.

And yes, he's still buying and selling real estate.

But he’s doing it his way.

Shay's latest story

He didn’t plan to stay in Thailand.

He flew in last November, thinking he’d be back in Miami by January.

But something clicked.

The island life got to him—no shirt, no shoes, no stress.

He bought a house (well, leased it for 30 years—more on that later).

And the deeper he went into this new rhythm, the more his old goals started to look… off.

Shay doesn’t want a $50M sq. ft. portfolio anymore.

He doesn’t want to be the guy doing 10 deals a year, managing 100 investors, waking up to urgent calls about construction delays or quarterly reports.

“Everything comes with a price,” he told me, “you gotta ask—do I want to pay that price?”

The answer, for him, was no.

He’s optimized for freedom, not bragging rights.

Which brings us to the Pensacola deal.

The Not-So-Sexy Strip That'll Net $2M

2400 W. Michigan Ave, Pensacola, FL.

Built in 1986. 28 units. ~29,000 square feet of retail.

The kind of place you drive by and don’t notice.

And that's exactly what Shay wanted.

He’d known the broker for years and built the relationship.

When the deal hit the market, Shay made an offer, but it didn’t win.

Someone else came in with full ask, all-cash.

Then?

The buyer ghosted.

Turns out he was dealing with mental health issues and couldn’t close.

The broker remembered Shay.

Knew he could perform.

Knew he wouldn’t retrade.

A few days later, he got the deal—for $1.55M, about $50/SF.

Classic.

When he closed, occupancy was 75%.

But within weeks it dipped to 50% as some mom-and-pop tenants walked.

Shay started upgrades to the property (about $300K in capex) and started pushing rents—up from the $6–7/SF gross legacy leases to $13–14/SF NNN.

Market’s at $17/SF, so he’s still leaving meat on the bone for the next buyer.

By the time he’s done, NOI should be $360K.

At an 8% cap, that’s a $4.5M valuation.

All-in for under $2M.

Expected net: $2M+.

No rezoning issues.

No ground-up development headaches.

Just a clean, easy lift, done right.

Why He’ll Sell It—Even Though It Cash Flows

You might be asking, why not hold it?

$175K+ annual cash flow isn't bad once finished?

But for Shay, the answer’s simple: it’s not worth the mental overhead.

He doesn’t want to manage 27 mom-and-pop tenants.

He doesn’t want to hold long-term in a market where the median income is ~$60K and tenant quality is hit or miss.

And most importantly, he doesn’t need to hold.

He’d rather exit, take the cash, and invest in something lighter and less management-intensive even if it cash flows less.

Maybe a single-tenant deal.

Maybe nothing at all.

He’s not chasing more.

He’s focusing to want less.

The Mentor

At the center of Shay’s shift is a story he told me about a mentor he met in Thailand.

A former cybersecurity tycoon who once owned 100+ companies.

He was roiling in the big leagues and chasing more.

Then, a decade ago, the guy walked away.

Sold everything.

Gave the money away.

Became a monk.

Today, the guy lives in a tiny apartment, owns three shirts, and spends his time helping others.

No flexes.

No agenda.

Just presence.

Simplicity.

The monk shared a simple idea with Shay: once your basic needs are met, wanting more will actually bring stress, not happiness.

If you already eat three good meals a day, adding five more won’t help.

If you have a home and a car, getting five more won’t make you feel better.

Instead of always chasing more, try put more energy in wanting less.

That’s where freedom starts.

And when you do that, you can feel truly grateful and excited about the life you already have.

That story stuck with Shay.

And it resonates with me too.

We’re always told to go bigger—more units, more deals, more square footage, more territory.

But no one tells us what that “more” really costs.

Sometimes the win isn’t in scaling up.

It’s in stepping back.

Takeaways

So what do you learn flipping a small strip center while living on an island with no Starbucks?

1️⃣ Relationships is GOLD in this business – Shay didn’t get this deal by being the highest bidder. He got it because he was known, trusted, and real. “Take your broker to coffee. Stay in their face. Be top of mind,” he says. Especially in smaller markets.

2️⃣ Focus on Easy Lifts – This wasn’t a sexy deal. But it will be a banger in terms of value added with not too much headache.

3️⃣ Build Your Team and Stick With It – Shay's been working with the same GC, same broker, same team for over a decade. Why? Because trust, loyalty, and shared values matter more than saving a few bucks by micromanaging new people.

4️⃣ Your PFS Isn’t Your Scorecard – Shay doesn’t chase status anymore. “My goal is to want less,” he told me. “Not to have more.”

Happy Sunday.

Be Well,

This is where I ask you to reply, and you think “he probably doesn’t mean me.”

I DO!

Hit reply.

Tell me what you think.