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

2 years ago, I made a bet.

Quit my job. Sold my house. Moved 3k miles across the country to buy a hotel.

(Pro tip: don’t do a cross-country road trip in a Tesla.)

At the time, interest rates were climbing.
Headlines were ugly.
Short-term rentals were getting crowded.

But one thing felt obvious.

People weren’t just craving nicer rooms.
They were craving connection, wellbeing, and real experiences.

After buying, renovating, operating, and selling 20+ vacation rentals, a few truths kept repeating:

• People wanted experiences > things
• People want to leave a trip recharged, not exhausted
• Groups want to travel together, but still want privacy
• And yes… people notice when you actually invest in design and cool amenities

So we doubled down.

We bought The Fern Valley Inn for $1.5M.
It was being run more like a hobby from a retiring couple.

The pool was used as a rainwater cistern.
There was a life-size gorilla statue.
The vibe was 2001 Odyssey…literally.

It was quirky.
And it needed love.

We saw the opportunity.
But not without it's challenges.

We almost lost the deal more than once.
Insurance. Financing. Capital. Timing.
Every obstacle showed up.

But here’s what happened at The PineTree Hotel in 2025:
• 3X’d property value: $1.5M → $4.5M+ in under two years
• $725k+ total 2025 revenue, up from $108K in 2022 (Almost 7x increase)
• $280k+ in full property buyouts, weddings, retreats, group getaways
• 37k+ social followers and 5K+ guest emails
• 1,726 reservations
• 4.9⭐ on Google
• 1:1 depreciable losses: $100k investment got $100k loss
• Over 2X'd investor equity, 40% return of capital, and 20%+ cash on cash 

My lender laughed when I told him last years numbers.
The bank said we’d be lucky to hit $300K stabilized.
This deal never "made sense" in a spreadsheet.

Because the opportunity wasn’t just a hotel conversion.
It was a shift.

As AI and tech accelerate, people want the opposite:
Real places.
Real connection.
Real experiences.

That’s what we’re building with THE PINETREE HOTEL, The Ellijay, and Willow Falls.

Places where you:
 • Bring your whole family & crew
 • Disconnect in nature
 • Reset your body and mind

Looking back, the only mistake was not making the bet sooner.

This isn’t a trend.
It’s an economic shift.
Experience is becoming the standard.

If you want to:
👉 Invest in real estate you’d actually want to stay
👉 Partner to build more of these
👉 Or sell a property with untapped potential

Drop a follow.
And join the newsletter in the comments 👇
It’s just starting to get fun.

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Q1 - Top performing SDR
33 qualified meetings (138% of quota) 

Top performing SDR 2017 

Registered Pharmacy Technician

Played for University of Tampa's men's soccer team.

Majored in Chemistry while completing the prerequisites necessary to pursue a Pharm D.



Helping you build an intentional life through boutique hotel investing

My first short-term rental was born out of my love for travel and spending time with family and friends. It helped that my first Airbnb booking covered half the year’s mortgage. I was hooked.

In that moment, I saw the opportunity to curate exceptional experiences that not only create lasting memories but also drive real value.

Since then, I’ve been on a mission to create stays that embody adventure, wellness, and community. We acquire and operate properties we’d want to bring our own family and friends to—places that feel both inspiring and familiar.

After personally acquiring 11 short-term rentals, I co-founded Second Home Stays with my lifelong friend and business partner. Through our own portfolio and partnerships with other property owners, we deliver first-class “home away from home” experiences for travelers.

I also founded the Ensmann Short Term Rental Fund to help busy professionals invest in top-tier short-term rentals and experiential hospitality. And now, with our boutique hotel fund, we’re redefining how groups travel by acquiring properties like The PineTree Hotel and incorporating local design, wellness, and sense of community into every stay.

My focus is on acquisitions, investor relations, and optimizing hospitality operations to create unforgettable guest experiences and strong investor returns. I believe every trip should be more than just a place to stay—it should be an experience that leaves a lasting impression.

Today, Second Home Stays has managed over 30 short-term rental properties and a boutique hotel, with assets valued at over $10 million. Through the Ensmann STR Fund, we’ve invested in more than 75 short-term rental properties across the U.S., totaling over $37 million in value.

I currently live in Tampa, Florida, and remain committed to shaping the future of boutique hospitality and short-term rentals—helping others create spaces that guests love and investors trust.

Ways I Can Help:

1️⃣ Hands-Off Hosting: Let Second Home Stays manage your short-term rental for a top-class, stress-free experience.

2️⃣ Buy a Boutique Hotel: Access my free course to learn how to purchase and operate your own boutique hotel.

3️⃣ Invest with Us: Explore exclusive investment opportunities through our Boutique Hotel Fund.

THE PINETREE HOTEL

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

Bought this spot in South Bend for $126K.
Sold it 22 months later for $387K.
Here’s the story 👇

A close buddy of mine, Luke, called one day and said:
“Tim, I’ve been watching what you’re doing with short-term rentals. I think I found a deal for you.”

Some important context:

• I had never been to Indiana, where he lived
• I knew nothing about South Bend other than University of Notre Dame
• I’m based in Tampa, where $126K barely buys a parking spot

But I trusted Luke.

The property was a 3 bed, 2 bath with a pool, solid land, and real upside.
It also needed work.
A lot of work.

We ran the numbers and studied short-term rental comps around Notre Dame.

What stood out wasn’t how well the listings were performing.
It was how boring they all were.

So we leaned into what actually wins:

• Hometown character
• Thoughtful design
• Differentiated amenities
• A stay where people could build a tradition

Then the fun stuff hit.

Plumbing issues.
Septic issues.
Roof and siding issues.
Basically every issue you can imagine.
$40k added budget

We gutted the house and renovated it top to bottom.

Year one results:

• $100K+ in revenue
• 3X'd the home’s value
• Cash flow and a refinance paid us back roughly 2x

We sold the property 22 months later with ~$50K already on the books for the next owner and exited at $387K.

The honest takeaways:

1. Residential real estate doesn’t always fully reward performance.
Even with strong income, you’re still capped by residential valuations when there’s nothing truly comparable.

2. If you get the chance to do something fun with people you trust that fuels both personal and professional growth, do it.
The $150K was great.
But a #1 listing, tailgates, Shane Gillis, and Zach Bryan concerts were forever.

If a property or venture lights you up, you’ll find a way to make it work. Creativity shows up when success is the only option.

That experience is a big reason we’re now all-in on boutique hotels, where cash flow, experience, and brand directly drive value through commercial valuation.

If stays, stories, and returns like this interest you,
follow Tim Ensmann or join my newsletter in the comments.

Credit to → Luke Harris + Isaac J Silverman

SDR → Multi-Hotel Owner
What I learned along the way

In 2016, I got my first sales job as an SDR at a small tech company in Tampa.

Zero business background.
Zero sales experience.
Coming straight from pre-med prereqs and soccer.

Owning three hotels less than ten years later definitely wasn’t on my bingo card. But looking back, a lot of what sales taught me shows up every single day as a hotel operator.

1️⃣ Lesson 1: Failure is feedback

Sales teaches you this fast. Rejection isn’t personal.
Someone hanging up on you doesn’t mean they hate you.
They don’t know you.
They don’t have time.
They’ve got their own stuff going on.

Your job is to stop taking it personally and figure out what actually happened.
That mindset translates directly into ownership.

I’ve lost a lot of time, money, and effort on deals, diligence costs, and bad hires. But I’ve made 10x that by staying in the game. If you can’t handle some losses, you’ll never get the wins.

The only things you truly control are mindset and effort.

2️⃣ Lesson 2: Time is money

Your top 20% of customers, accounts, and investors will drive 80% of your success.

Sales teaches you not to waste time on things that won’t pan out and to double down on the highest upside activities.

Not every lead is worth chasing.
Not every deal deserves your energy.

As an operator, where you spend your time, attention, and focus sets the ceiling of the business.

3️⃣ Lesson 3: Relationships compound

The real edge isn’t the transaction. It’s the relationship behind it.

Champions, customers, colleagues, bosses, investors, and partners compound when you invest in them the right way.

You become the average of the people you surround yourself with. They shape how you think, what you normalize, and what you believe is possible.

Sales taught me to play long-term games with long-term people. That mindset carries directly into ownership.

4️⃣ Lesson 4: Leadership scales everything

Eventually, you have to outgrow being an individual contributor if you want to build something big.

It stops being about what you can do.

Your people matter more than your individual performance. If a team is full of C players with a couple A players holding it together, that’s not bad luck. That’s a leadership failure.

As an operator, recruiting, upskilling, and building systems becomes the real work. You have to hire people who are better than you or who will be soon.

Sales didn’t just teach me how to sell.

It taught me how to think, how to lead, and how to build something that lasts.

Curious what lessons have carried over for you as your career has evolved?

#sales #Leadership #CareerGrowth #RealEstateInvesting #Hospitality #BusinessOwnership

No alternative text description for this image

I felt like the guy from The Big Short when I saw this...


A hotel in one of the most beautiful locations in California.
Thousands of past guests.

And a broken website.

Half-baked site.
No socials.
The owners still answered the phone.

Incredible setting.
Real demand.
Digitally invisible.

That moment stuck with me.

Because on paper, hospitality looks saturated.
Headlines say: “Demand softening!”
“Competition increasing!”

But on the ground, there’s a mismatch.

The extremes are crowded.
Flagged hotels are optimized machines.
Economy lodging competes on price.

The middle is different.

People don’t want a room anymore.
They want a memory.
An atmosphere.
Something they can’t replicate at home.

Demand moved faster than supply.

So you get incredible properties
with real demand
still operating like it’s 2005.

I used to think opportunity meant seeing something no one else saw.

Now I think it’s noticing what everyone sees
but hasn’t fully processed yet.

The world moves.
Assumptions lag behind.

Join our newsletter where we reimagine these type of places to serve modern travelers.

👉 https://bit.ly/49eumZv

Our first group booking covered our monthly debt service.
In 4 days.

Here’s how it happened 👇

When we bought THE PINETREE HOTEL, we had a hunch.

Not about nightly rates.
Not about occupancy.

But about groups.

People didn’t want just a place to sleep.
They wanted a place to gather.

Retreats.
Celebrations.
Small weddings.
Moments that actually mattered.

At the time, we had nothing polished to show.

No finished amenities.
No event space.
No professional photos.

Just Instagram stories.
Wide shots of the land.
Construction updates.
A rough vision.

Still, interest started to trickle in.
A birthday request here.
A small wedding request there.

Nothing truly game-changing.
Or so we thought…

In our underwriting, we assumed one group booking per month.
A nice bonus.
Not a core driver.

But we decided to test the idea early.

Before the space even existed.

We invested in three renderings:

• A wellness area (pretty close to what exists today)
• A year-round heated pool in the mountains
• A full site layout showing how the property came together

Then we recorded “our story” video.

Who we were.
What we were building.
Why it mattered.

We dropped it onto our website.
Which, to be honest, still needed work.

Two weeks later, it happened.

Our first group booking came through.

One long weekend.
Enough revenue to cover the entire month’s debt service.

That was the moment everything clicked.

We weren’t selling nights.
We were hosting events.

From there, we put our enterprise sales hats on and focused on building a predictable pipeline of group travel.

In year one:
• Group bookings covered 60%+ of our debt service 
• From just 8% of rentable nights

Fast forward to now.

One month into 2026,
we’re already at 67% of our total group bookings from all of 2025.

That changed how we see hospitality.

Forever.

If you want to learn more about how we're doing this,
follow Tim Ensmann and join the newsletter in the comments.

Ari from Entourage is making a billion-dollar anti-AI bet 👇


He’s betting on live events.

His belief is, as AI gets better:
• Work gets faster
• Productivity explodes
• The work week shrinks
• Content becomes infinite and basically free

So what actually becomes more valuable?

Real life...

Live sports.
Concerts.
Nature.
Retreats.
Real moments with real people.

Elon Musk even said "you can’t recreate live".

In a world drowning in screens, presence becomes the luxury in high demand.

The question isn’t whether AI changes everything.
It’s whether we’re underestimating how much it increases demand for real human experiences.

Do you think this is a good bet for 2026? 

https://lnkd.in/eRrjkzR3

youtube.com

Ari Emanuel’s "Anti-AI" Bet on Live Entertainment

Hotel occupancy fell for the 9th straight month.

The middle was exposed. A few stood out.

2025 didn’t widen the gap between great and average.
It clarified it.

Most hotels didn’t fail.
They stayed open.
They survived.

But the undifferentiated middle started eroding quietly.

Here’s what 2025 revealed and why it matters heading into 2026:

1) Distribution decides durability
OTAs still matter.
They’re just not neutral.

They tax margin.
They own the guest.

The operators who performed built direct relationships through content, email, and social.
Not to save commission.
To gain control.

No real distribution strategy = fragile business.

2) Volume stopped protecting margin
For years, filling nights was the goal.
It stopped working.

When demand softened, predictability mattered more than exposure.

High-intent group bookings quietly stabilized P&Ls.
Buyouts. Retreats. Weddings.

Fewer nights.
More clarity.
Less chaos.

3) Experience beat “nice”
People didn’t stop spending.
They stopped tolerating average.

Generic rooms competed on price.
Distinct experiences competed on feeling.

Nature. Wellness. Gathering.
Contained experiences removed friction and decision fatigue.

4) AI became infrastructure
Not innovation.
Infrastructure.

Clear systems.
Fewer vendors.
Better handoffs.

Nothing flashy.
Just calmer operations and fewer dropped balls.

Small wins compounded.

5) The middle cracked
Not luxury.
Not budget.

The middle.

No headline collapses.
Just steady erosion.

What works heading into 2026:
• Owned audiences
• Revenue booked in advance
• Clear identity
• Fewer decisions, executed consistently

2025 wasn’t a downturn.
It was a filter.

And 2026 will reward the operators who noticed.

Pinetree Q4 Report
18% cash on cash | 41% capital returned | 1:1 depreciation
See the report 👇

This isn’t projected performance.

This is real cash flow.
Real distributions.
Real operating leverage.

Q4 highlights:

NOI reached $157,685
That’s 191% of target

Operating expenses dropped to 36%
Top percentile among hospitality operators

84% of bookings are direct
Not Airbnb. Not OTAs.

Group sales are now a predictable revenue engine
On track to cover 100% of annual debt service in year two
With surplus cash flow on top

That last point matters.

Most hospitality assets live and die by seasonality and transient demand.

Ours doesn’t.

In 2025:
Group bookings covered 60%+ of debt service
From just 8% of rentable nights

One month into 2026
We’ve already booked ~67% of last year’s total group volume

That’s what happens when brand, pricing power, and operations are aligned around predictability and a differentiated experience.

Investors just received another quarterly distribution.

Results to date (2 years):
• 18% cash on cash return
• 41% of invested capital returned
• Strong equity growth
• 6+ months of debt reserves
• Consistent quarter over quarter improvement

Based on operating data.
Not spreadsheet assumptions.

The opportunity here isn’t finding demand.

It’s allocating capital behind a system that’s already working
While inefficiencies still exist

We’re replicating this inside the Blue Ridge Hotel Collection
Stronger fundamentals
More scale
More room to build a moat

PineTree
Multiplied.

If you want the full Q4 report or want to learn more, join our newsletter in the comments.

A 2% fee can quietly cost you $140,000 over time
in accounts you may not fully understand.

If you’re unclear on:
• What your retirement accounts are actually invested in
• What fees and structures you’re paying for
• How to diversify retirement capital beyond public markets

This Thursday, we’ll cover:

• How to take back control of your retirement capital
• How everyday investors access strategies used by the ultra-wealthy
• How diversification actually works inside retirement accounts
• Where fees, structure, and control really matter
• How to ask better questions and avoid common blind spots

📅 Thursday, January 29
⏰ 12:30 PM (Live)

One of the biggest misconceptions about strategies used by ultra-wealthy investors is that they’re only available to people with massive net worth. Th

Open article: Invest Like the Ultra-Wealthy with your IRA by Tim Ensmann • 4 min read

Invest Like the Ultra-Wealthy with your IRA

This is the stuff I wish I had understood 10 years ago.

Most people can’t explain what their IRA or 401k is actually invested in.
I was one of them.

A Self-Directed IRA lets you invest beyond the stock market while still benefiting from tax-deferred or even tax-free growth. More importantly, it gives you back control over what you’re investing in and the fees you’re paying.

Once you understand how control, structure, and compounding really work, retirement stops feeling passive and starts feeling intentional.

In this webinar, you’ll walk away with:
 • Clarity on what your retirement money is actually invested in
 • A clear view of how fees quietly compound against you
 • Understanding of IRA structures and where control really matters
 • A long-term framework for smarter retirement decisions
 • Confidence to ask better questions and avoid costly blind spots

Join us with IRA Club next Thursday.

IRA Club

2025 clarified where value is being created.

Good held on. Unique compounded.

Here’s what that points to in 2026 👇

2025 was the year the gap between great and average didn’t just widen. It clarified. For the middle of the pack, it felt like watching a team barely m

2025 clarity. 2026 bets.

One pattern keeps showing up in wildly successful people
like Jerry Seinfeld, Bob Dylan, and MrBeast.

Great companies, comedians, and musicians weren’t built by chasing trends.
They were built by people who aligned real interest with their work.

Bill Gurley, one of Silicon Valley's most respected venture capitalists, frames it with a simple question:

What do you do in your free time?

Not what you say you care about.
Not what looks good on paper.

What you actually spend time on
when no one’s paying you
and no one’s watching.

He ends the podcast and his book with a line that stuck with me:

“It isn’t easy.”

And that’s the point.

If you’re choosing to spend your free time on something
and you’re willing to stick with it long enough,
the effort compounds.

Quietly at first.
Then all at once.

That question is usually the clue.

What do you do in your free time?

- Credit to Tim Ferriss (#840) and Bill Gurley

If you raise capital, vet deals, or buy real estate,
these are 5 GPTs you need 👇

One for each part of the decision stack:

Deal vetting.
Diligence.
Structuring.
Pitching.
Advisory perspective.

Vetti | Deal vetting
Cuts through numbers, PPMs, decks, and assumptions to surface real risk.
Doesn’t tell you what to do.
Shows you what you’re missing.

Dewey | Diligence
Catches second-order problems early.
Flags gaps and red flags that feel “fine” until they aren’t.
It eliminates surprises quickly.

Deal Structure Ninja | Structuring
Where most good deals actually die.
Not price. Not returns.
Structure.
Helps explore tradeoffs before lawyers and partners lock things in.

1 Line Investor Pitch | Pitching
This one is humbling.
If you can’t explain the deal in one sentence, you got work to do.
Forces clarity fast.

HyperIntelligent | Advisory perspective
Like having your own Shark Tank advisory board at your disposal.
Trained by decamillionaires to pressure test decisions across investor and operator perspectives.
Great when you’re too close to the problem.

Faster Feedback.
Fewer blind spots.
Better decisions.

Comment GPT and I’ll send you the links 👇

Retirement Mistakes that Cost 7+ figures

What percentage of millionaires received an inheritance?

(Will share stat next week)

What percentage of millionaires in the US received an inheritance? 

Join us to learn how to take control of your retirement beyond the stock market.

Jordan Graves, Ankur Pandita and 49 other attendees

View event: The IRA Decisions That Separate $1M From $4M

The IRA Decisions That Separate $1M From $4M

Only 21% of millionaires received ANY inheritance.
Just 3% received an inheritance of $1 million or more.

Yet 74% of Millennials believe most wealth comes from inheritance 
(And ~60% of my LinkedIn votes below)

That disconnect didn’t happen by accident.

Social media is powerful.
It’s a huge advantage when used well.

But when it becomes your primary source of economic education,
you start learning from viral takes instead of how things actually work.

And you begin absorbing ideas that sound good, but are simply untrue.

Like:

“Billionaires shouldn’t exist.”
Often said on a device built by a trillion-dollar company…

“Tax the rich more.”
The top 1% already pays roughly 40–45% of all federal income taxes.
Meanwhile, government spending runs into the trillions every year.

“Rent should be capped.”
Ask any group of serious economists and you’ll hear the same conclusion:
rent control lowers housing quality, reduces supply, and pushes prices higher elsewhere.
(One Harvard economist famously called it the quickest way to wreck a city without explosives.)

“The system is rigged.”
In reality, most American millionaires are first-generation wealth builders.
They didn’t start rich.

To be clear:
the economy isn’t perfect.

Inflation is painful.
Healthcare is a $h!t show.
Wages could absolutely be higher.

But real problems don’t get solved with made-up economics.

The idea that wealth is mostly inherited is simply wrong.
And it’s a convenient belief.

Because if the game is unfair,
you’re not responsible for the outcome.

While some people argue online, others focus on fundamentals:
discipline,
saving,
investing,
and long-term thinking.

The system has flaws.

But it’s far less broken than those who’ve never taken the time to understand it want you to believe.

Cobalt

Senior Business Development Representative - Enterprise

Business Development Representative

College Works Painting

-Delivered $101,000 in revenue in a six-month period, while a full-time student
-Estimated and managed painting projects up to $13,000
-Hired, trained, and managed a team of 6 employees
-Designed and implemented a marketing plan that sourced over 120 leads
-Presented professional proposals to clients, negotiated and closed deals, and built meaningful relationships 
-Oversaw all aspects of production management, customer relations, and quality control
-Lead conversion rate of 54%
-Booking percentage of 24%
-Average job size of $5,900

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Tim Ensmann

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The Battle

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