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.

undefined undefined

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

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

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.

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.

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.

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.

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

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

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.

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 👇

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

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.

Acquiring exceptional wealth-building real estate for my investors Helping them build more fulfilling lives through financial strength

📈I help people reach financial security
🦉I educate and demonstrate - how you benefit from investing in apartments, realistic expectations, how to analyze opportunities
💻I have helped people of all backgrounds but specialize in helping tech professionals who can't see a path to financial freedom
👨‍👩‍👧‍👦I bring investment opportunities to people who need strong returns, income, predictable outcomes, and shelter from taxes and market turbulence. 

I founded Cardinal Oak Investments to create opportunities for stable, long-term investments in the safest and most reliably secure types of real estate, multifamily apartments. Through general partnerships with other experienced managers, we create real estate syndications to invest in apartments in strategic growth markets in the U.S. 

My extensive experiences with software development, management of technology teams, and implementation of large software solutions at Fortune 500 companies were invaluable skills to help my success in real estate. 

Now I create opportunities for investors seeking stable, long-term income and wealth building through real estate, and limited and general partnerships investing in apartments. 

My company acquires properties in emerging markets where rental demand is strong, the community is growing, and smart renovations will drive rent growth. We modernize stable but outdated apartments and create clean, comfortable, and safe residential communities.

Sharing my experiences through speaking engagements, guesting on podcasts, and publishing a newsletter I’m constantly looking for opportunities to help others get to the next level in their real estate investing, wealth planning, and passive income opportunities.

John Todderud

Working across time zones actually helped me.

When I started looking outside my local market, something unexpected happened.

My schedule improved.

I was on the West Coast. Many of the markets I was working in were two or three hours ahead.

That created a natural advantage.

Early mornings became my most productive window.

The people I needed to reach were already working.
Brokers. Owners. Property managers.

Calls didn’t sit unanswered.
Conversations moved forward.

It also changed how I handled callbacks.

If I left a message early and someone returned it later, I stayed ready to answer. Even if the number was unfamiliar.

Progress often came from short conversations, not long meetings.

Here’s what that structure gave me:

• Clear separation between work and real estate
• Faster back-and-forth with decision makers
• Fewer stalled conversations
• Quiet time

None of this was planned.

It was practical.

Looking back, working across time zones created focus without adding hours.

That mattered more than I realized.

Where would real estate fit into your current schedule today?

No alternative text description for this image

“Turnkey” used to be a deal killer for me.

For most of my investing career, I passed on fully renovated properties.

If the work was already done,
I assumed the value was already captured.

No upside.
No room to improve.

That logic worked in a different market.

Today, it’s changing.

Some of the most interesting opportunities I see now look “finished” on the surface.

The major renovations are complete.
The property shows well from the street.
The interiors have already been upgraded.

But the numbers no longer work.

Usually because of:

• Debt that needs refinancing
• Timelines that no longer pencil
• Interest rates moving faster than expected

In these cases, the problem isn’t the asset.

It’s the balance sheet.

The value today isn’t created through construction.
It’s created through operations.

• Stabilizing occupancy
• Improving tenant quality
• Running the property with discipline
• Holding steady while others are forced to sell

That kind of value-add doesn’t look impressive in photos. But it’s the kind that survives a full cycle.

What criteria have you adjusted in the last year?

One of the first skills I had to learn was filtering brokers.

When I started looking at small apartment buildings, I didn’t have a primary broker.

I was finding properties myself.
Usually three to ten units.
Mostly local.

I’d reach out to the listing broker and ask for the financials. What came back was often messy.

Many of those brokers came from single-family.

Rent rolls weren’t familiar.
Income statements weren’t either.

They shared whatever the owner provided.

Not every broker is set up to sell multifamily.

Over time, I started paying attention to patterns.

Who understood income.
Who asked better questions.
Who actually worked in this space.

Filtering brokers became a real skill.

Here’s what I learned to look for:

• Comfort discussing rent rolls and expenses
• Experience selling income-producing property
• Clear answers instead of assumptions
• Responsiveness and follow-through

That skill saved me time.
And it reduced mistakes.

If you’re early in the process, this matters more than most people expect.

The right broker doesn’t just help you find a deal.
They help you understand it.

The hardest part of multifamily is not finding a deal.

Early on, I thought deal flow was the challenge.

→ Finding the market.
→ Getting access.
→ Winning bids.

That part gets easier with time.

What doesn’t get easier is what comes after.

Operations.

I’ve owned properties in good areas that should have performed better.

On paper, they looked fine.
In practice, small issues were piling up.

Here is what usually shows up first:

• Delinquencies starting to creep up
• Occupancy drifting instead of stabilizing
• Maintenance issues staying unresolved

None of this happens overnight.
That is exactly why it is dangerous.

By the time a problem looks obvious, it has usually been building for months. Changing property managers can help, but it is never a quick fix.

Bad tenants still have to be addressed.
Leases still need to be cleaned up.
Systems still need to be rebuilt.

That work is uncomfortable, but it matters.

Finding a deal is only the starting point.
Running it well is where value is created.

What’s been harder for you; buying or operating?

I’m not running properties day to day anymore.

That wasn’t accidental.

Early on, I was involved in almost everything.
Operations, decisions, follow-ups, details.

That’s normal when you’re building.

But as the portfolio grows, the job changes.

Today, I stay close to the properties.

I stay informed.
I stay involved when it matters.

I’m just not the one handling the daily work.

There are people who are more available than I am.
More immersed in the day-to-day.
And frankly, better at it.

My time now is spent reviewing information.

• Reviewing property financials
• Watching early indicator metrics
• Asking questions when something doesn’t look right.

That’s how I can stay proactive instead of reactive.

Stepping back from daily operations didn’t reduce responsibility. It changed where my attention goes.

And that shift is necessary if you want to grow without creating risk.

How has your role changed as things have grown?

I built my early real estate experience around a W2 job.

I didn’t quit my job to get started. I worked full time and fit real estate into the margins of my schedule.

Most of the early work happened outside normal hours.

• Evenings reviewing listings and financials
• Weekends driving properties and meeting brokers
• Early mornings when that worked better

During the day, I took calls when I could and kept it discreet. I wasn’t announcing broker calls to coworkers or making a show of it.

Early on, I focused on small apartment properties, usually three to ten units. Nothing complicated.

I didn’t have a broker bringing me deals. I found listings myself, reached out to listing brokers, and asked for the numbers.

A lot of what came back wasn’t great.

• Brokers unfamiliar with income properties
• Rent rolls that lacked clarity
• Incomplete or messy financials

Reviewing that information still mattered. That’s how I learned what to question and what to look for.

The biggest adjustment wasn’t finding time. It was being responsive.

• Returning calls promptly
• Following up consistently
• Not letting conversations stall

You don’t need full-time availability to get started. You need to be reliable in the time you do have.

That’s how it worked for me early on.

90–92% occupancy can still be a red flag.

I’ve owned a property that sat at 90% for months.

On paper, everything looked acceptable.
In reality, something wasn’t working as it should.

The market was solid.
The location supported higher demand.
Yet occupancy never moved meaningfully higher.

That’s when we realized occupancy wasn’t the issue.
It was what sat underneath those numbers.

Here’s what showed up first:

• Late maintenance responses
• Delinquencies starting to quietly increase
• Renewals happening without enough scrutiny

None of this shows up overnight.
It builds slowly, then becomes hard to unwind.

We eventually changed property managers.
That helped, but it wasn’t a clean reset.

A new manager inherits real problems:

• Old leases
• Deferred maintenance
• Tough tenant decisions that were delayed

That work takes time to correct properly.

Once we addressed those issues, performance improved. Occupancy moved higher. Rents followed.

The lesson wasn’t to push harder for occupancy.
It was to pay attention sooner.

When your metrics are set correctly, you don’t get surprised. You see the issues coming.

What do you look at before occupancy changes?

I ignored northern markets for a long time.

For years, I stayed focused in the same direction.

Not because I hadn’t looked at them.
But because I thought I already had the answer.

I followed the same narrative most investors do:

• Population moving south
• Companies relocating
• Jobs following

It wasn’t limited to Texas, Florida, or Arizona. It extended across much of the southern tier, including parts of the Midwest.

It worked, and consistency made it easier to stay focused.

But recently, I started seeing strong investors succeed in places I had mostly ignored.

Not fringe markets.
Not short-term spikes.

Cities with:
• Real job growth
• Stable populations
• Business-friendly rules
• Rent growth that continued after COVID

That forced a pause.

The original belief wasn’t wrong.
It just wasn’t complete.

Sometimes the right move isn’t changing direction.
It’s checking whether your assumptions still hold.

What belief has changed for you over time?

3 beliefs I held for years that I’m rethinking in 2026

Even beliefs shaped by experience can change. The market, opportunities, and timing force a fresh look.

Here are 3 I’m rethinking this year 👇

1️⃣ The best opportunities are in southern markets
2️⃣ Value-add requires heavy renovations
3️⃣ More work means more upside

You don’t need to ignore your past beliefs.
You just need to adjust where it makes sense.

Which belief are you rethinking right now?

Beliefs I Held for Years That I’m Rethinking in 2026

Underwriting isn’t an 8-minute task for me.

There are quick ways to pass on a deal.

If I see a clear red flag early, like no upside in rents, the condition being worse than expected, or something simply not lining up, I’ll move on.

That part doesn’t take long, and it saves time. But if a deal gets past those initial filters, I don’t rush it.

Underwriting, for me, means bringing several pieces together so I can understand what I’m looking at:

• Physical condition and deferred maintenance items
• Profit and loss statements over multiple periods
• Comparable rents and broader market context
• Rent roll details and trends inside the property
• What information is missing and why it matters

At that point, I’m not trying to move fast.

I’m trying to decide what the next step should be.

• Do I ask the broker for more information?
• Do I spend more time digging into the numbers?
• Or do I decide it’s not the right deal and move on?

That takes real, uninterrupted time. I’ve spent an hour or more on properties that didn’t feel right at first.

Only later did it become clear there was an opportunity worth pursuing.

If I had stopped too early, I would have missed it.

Fast underwriting helps you say no quickly. Thoughtful underwriting helps you make better decisions.

What usually makes you pause on a deal?

taplio

The Battle

Tim Ensmann

John Todderud

Followers

Posts

Engagements

Likes

Performance ScoreTim Ensmann's LinkedIn Performance

Performance ScoreJohn Todderud's LinkedIn Performance

Ready to grow your LinkedIn presence?

taplio

The Battle

Tim Ensmann

John Todderud

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 ScoreJohn Todderud's LinkedIn Performance

Ready to grow your LinkedIn presence?

Performance ScoreTim Ensmann's LinkedIn Performance