In November 2023, I burned the boats.

I quit my job, sold my house, and drove 3,000 miles across the country to Idyllwild, California.

No job. Rising interest rates. STR competition heating up. Market skepticism everywhere.
But we saw an opportunity to build something people crave most today: connection, wellbeing, and extraordinary experiences.

After buying, renovating, operating, and selling 20+ vacation rentals, my partner Isaac J. Silverman and I saw some clear truths:

People love to travel in groups but hate sharing bathrooms.

People want experiences over things.

People want to leave a vacation recharged, not drained.

And yes, design matters.

So we doubled down.

We bought The Fern Valley Inn for $1.5M from an older couple who had been running it as a retirement hobby. With the support of 13 trusted friends and family investors, we reimagined it as The PineTree Hotel.

Here’s what happened in our first year:
• 3X property value: $1.5M → $4.5M+ in under two years
• $666K+ revenue (up from $108K in 2022)
• $257K in weddings, retreats, and full buyouts
• 25K social followers + 4.3K guest emails
• 1,406 reservations | 4.9⭐ on Google
• 21%+ cash-on-cash returns | Over 2X investor equity

Sometimes opportunity doesn’t show up in a spreadsheet. Sometimes it takes vision, belief, and relentless execution to see what others miss.

For a while, I thought I needed to “own more hotels” before sharing my story. But the truth is: The PineTree Hotel is proof of concept. People are hungry for experiences that recharge them, not just places to sleep.

And we’re just getting started.

We are already under contract on three more boutique hotels set to close in the next 90 days.

We’ve done it. We’re doing it. And now, we’re scaling it.

Ways we can work together:

👉 Invest in boutique hotels that you’d want to stay in
👉 Partner with us to acquire and grow properties
👉 Sell us a property with untapped potential

Drop me a follow or let’s connect, because what we’re building is only getting more fun.

Tim Ensmann

Supply is constrained.
Demand has shifted.
Pricing power in live experiences is real.

The 2026 Experiential Hospitality Report breaks down the data and unit economics behind it.

If you’re looking at how to balance AI with real assets, this is worth a read.

(Report in comments)

Sales Guy → Boutique Hotel Guy | Helping you build an intentional life through boutique hotel investing

Why Experiential Hospitality Is Quietly Outperforming The opportunity isn’t complicated. It’s supply and demand. When you zoom out and look at hospita

Open article: Supply < Demand by Tim Ensmann • 3 min read

I never expected to be laid off from a big tech company—but when it happened, I learned firsthand how fragile W-2 income and stock-heavy wealth can be without reliable cash flow.

At the time, my ~$3M residential rental portfolio was covering my living expenses. That income stability allowed me to stay calm, avoid forced decisions, and focus on building what came next without needing to dip into my savings or prematurely sell any of my RSUs to stay afloat.

Today, I help high-income tech professionals build layoff-resilient cash flow by investing in short-duration fix-and-flip residential real estate loans—designed to generate consistent income without relying on small dividends from stocks and bonds or drawing down principal by selling equities during market downturns.

Before real estate, I was a software engineer at Meta. I approach investing the same way I approached engineering: data-driven underwriting, risk decomposition, and repeatable systems.

At Bozeman Capital Partners, we manage ~$69M AUM in private debt focused primarily on 1–4 unit residential properties nationwide; this is intentionally different from most credit funds that concentrate on large multifamily. Our strategy centers on investor-purpose bridge loans secured by real assets, with an emphasis on capital preservation, diversification, and predictable income.

If you’re a high-income tech professional looking to diversify beyond stocks and build reliable income, learn more about our investment opportunities at:
https://www.bozemanpartners.com/

If you’re an active real estate investor looking for fix-and-flip, DSCR, construction, or bank statement financing, request a quote at:
https://www.bcpfinancing.com/

Kunaal Kumar

Contrary to what you might read on LinkedIn, you shouldn't "invest like the wealthy" if you only have $50k.

Every so often I see posts encouraging people to copy how ultra-wealthy investors allocate their portfolios. The argument usually goes something like this:

"High net worth investors allocate heavily to alternatives (private equity, real estate, private credit, energy, etc.), so if you want to build wealth, you should too."

That's not something I ever bought, and hopefully by the end of this post, you'll agree with me.

Take a look at the chart below from Tiger 21's quarterly member asset allocation report.

If you’re not familiar with Tiger 21, it’s a peer network of ultra-high-net-worth entrepreneurs and investors with a 𝗺𝗶𝗻𝗶𝗺𝘂𝗺 𝗶𝗻𝘃𝗲𝘀𝘁𝗮𝗯𝗹𝗲 𝗻𝗲𝘁 𝘄𝗼𝗿𝘁𝗵 𝗼𝗳 $𝟮𝟬𝗠.

Ultra-high-net-worth investors are playing a completely different game. Their primary goal is 𝘄𝗲𝗮𝗹𝘁𝗵 𝗽𝗿𝗲𝘀𝗲𝗿𝘃𝗮𝘁𝗶𝗼𝗻, not 𝘄𝗲𝗮𝗹𝘁𝗵 𝗰𝗿𝗲𝗮𝘁𝗶𝗼𝗻. Once you’ve already accumulated tens of millions of dollars, broad diversification across asset classes makes a lot of sense.

Early in your investing career, however, the objective is very different.

Here's my philosophy: when you're in hyper-growth mode, I think spreading your capital across a bunch of different asset classes is a suboptimal approach.

Instead, it usually makes more sense to focus on one area where you can build real expertise and develop an edge.

Too much diversification early on can dilute your ability to scale quickly.

That’s exactly the approach I took.

For years, I rolled almost all of my discretionary income back into my own fund. The reason wasn’t blind conviction—it was familiarity. I understood the underwriting, the collateral, and the risk profile of the loans we were originating. Concentrating capital in something I deeply understood allowed me to scale faster.

The same principle applies in other areas.

If you have a genuine edge in public equities, focus there.
If you understand a niche real estate market extremely well, lean into that.
If you build expertise in a particular strategy, double down on it.

Trying to spread a $100k portfolio across six different asset classes just because "that’s what wealthy investors do" usually doesn’t make much sense.

Diversification becomes powerful once you actually have something worth diversifying.

And that’s exactly when alternatives start to become interesting.

If you already have a more mature portfolio and are exploring ways to diversify into high-yielding real-estate-backed private credit, feel free to reach out.

Helping High-Income Tech Pros Build Layoff-Resilient Cash Flow via Private Residential Real Estate Loans | $69M AUM | Ex-Meta

I advised an investor against investing in our fund.

I was on a call with a prospective investor last week when I realized that our fund didn't line up with what the investor was looking for.

During our conversation, he mentioned two potential strategies that he was considering: 
 • Deploying capital through an SDIRA while avoiding UBIT
 • Allocating capital to generate depreciation to offset other taxable income

Our fund structure isn’t optimized for either objective.

Because we utilize a warehouse line, SDIRA investors could face UBIT exposure. And as a debt vehicle, we don’t generate any depreciation.

Fundraising is a long term game for me; convincing someone to invest just so I can get more capital through the door even if it's not the best idea for them just doesn't seem like a good way to build a business.

If I get the sense that an investor isn't a good fit, I don't want to commit to a 6 month (the length of our lockup period) relationship. 

This goes both ways: in addition to trying to figure out if our fund is a good fit for our prospective investor's needs, I also want to make sure that the investor is someone I want to work with.

Since I started building Bozeman Capital, I've turned away more than $1M in capital from people who I believed were misaligned with my long term goals.

Saying no to more capital is hard, but dealing with fundamental misalignment months (or years) later is much harder.

If you're unsure whether or not our real estate debt strategy is a good fit for you, feel free to reach out.

“I’m hoarding cash because that’s what Warren Buffett is doing.”

I’ve heard this a lot lately, but It never really felt quite right to me.

Berkshire Hathaway is currently sitting on ~$382 billion in cash. That sounds enormous (it's bigger than a lot of countries' GDPs)— until you compare it to the size of the overall portfolio.

Cash is roughly 30% of Berkshire’s assets...which means ~70% is still invested.

Also, to be clear, it's not literally cash: most of the money is in treasuries. 

Funnily enough, even while “stacking cash,” Buffett’s allocation is actually more aggressive than a traditional 60/40 stock-bond portfolio.

To be clear, this isn't an endorsement to start investing super aggressively; there’s real stress in the system. 

The last time Berkshire built a cash position of this size was ahead of the GFC. Preparing for volatility makes sense.

But I don't think it makes sense to use "Buffett stacking cash" as an excuse to not do anything.

Buffett isn’t all-in on risk.
He’s not all-out either.

He’s positioned.

You can invest offensively or defensively, but the worst thing you can do is opt out entirely.

My first rental deal was probably the best deal I'll ever do.

Here's why I desperately want to sell it regardless.

But first, here's why the deal was so good:

Purchase price: a bit over $600k
Cash down: ~$6k (was able to use down payment assistance to get a lower than normal down payment)
Renovations: ~$60k

All-in: ~$70k.

I lived in one bedroom and rented out the others. Net cash flow was about $1.5k/month — roughly $18k/year.

That’s ~25% cash-on-cash, before appreciation.

Fast forward to today:

• Loan paydown + appreciation put my equity around ~$300k
• Net cash flow has dropped to $500/month ($6k/year)
• Return on equity: ~2%
It was an incredible entry deal. It changed my life.

But here’s the problem:

1. Operational drag
Even with a property manager, coliving is operationally heavy. My PM handles most of the day to day, but something that requires my attention comes up at least monthly. Managing the asset isn't a good use of my time.

2. Market shift
Room rental supply in Seattle has expanded significantly since I bought this deal in 2021. I’ve never raised rents on this property, and if I ever changed the rents between leases, it was downwards, not upwards.

3. Capital inefficiency
Most people would see my returns above and see a bit less than 10% cash on cash. That's still higher than many multifamily deals to day. However, the big issue is my return on equity:

What started as a 25% cash-on-cash deal is now a 2% return on $300k of trapped equity.

Every investment I look at—including my own properties—gets compared to our fund strategies at Bozeman Capital. If we’re targeting 12–14% annualized net returns in a debt position, it’s difficult for me to justify accepting ~2% ROE from an equity position that sits in first-loss, carries personal guarantees, and requires operational oversight.

It’s not about selling to invest in my own fund.

It’s about opportunity cost. Capital should migrate to its highest risk-adjusted use.

This property was a great start, but it no longer aligns with my investing needs.

What's the lowest return on equity you would accept before you start questioning whether capital is better deployed elsewhere?

If you've ever thought “who is verifying the numbers?” when investing in a private deal, you're not alone.

In public markets, that function is largely handled by brokers, custodians, and exchanges. But in private funds, the manager is responsible for producing capital account statements, processing subscriptions, calculating distributions, and maintaining investor records.

There's a solution that blends the returns and deal structure of private investments with the transparency of public investments: third party fund administration.

A fund admin is an independent firm that sits between the fund manager and investors that handles key operational functions like:

• Maintaining the fund’s books and records
• Calculating investor capital accounts and allocations
• Processing subscriptions and redemptions
• Producing investor statements and reports
• Supporting a fund audit and tax reporting

For investors, the main benefit is independent verification.

Instead of relying solely on numbers prepared internally by the fund manager, a third party is responsible for maintaining the official records of the fund and reconciling activity each month.

This is very rare for smaller funds (since the fixed costs erode the returns), but is standard for institutional ones.

As Bozeman Capital has scaled and reached more institutional capital, onboarding a 3rd party fund admin is something that we're actively working on.

Our goal is simple: continue improving the operational infrastructure behind the fund as our investor base grows.

For investors allocating to private funds, it’s worth asking a simple question:

Does the fund use a third-party administrator?

If not, it’s worth understanding how the manager handles accounting, reporting, and investor record-keeping internally.

Operational infrastructure matters just as much as investment strategy in alternatives.

taplio

The Battle

Tim Ensmann

Kunaal Kumar

Followers

Posts

Engagements

Likes

Performance ScoreTim Ensmann's LinkedIn Performance

Performance ScoreKunaal Kumar's LinkedIn Performance

Ready to grow your LinkedIn presence?

taplio

The Battle

Tim Ensmann

Kunaal Kumar

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Tim Ensmann's LinkedIn Performance

Performance ScoreKunaal Kumar's LinkedIn Performance

Ready to grow your LinkedIn presence?

Performance ScoreTim Ensmann's LinkedIn Performance