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.

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

Here's an unpopular opinion: I hate retirement accounts. Here's why I cashed out my entire 401k last year, despite the 10% penalty. 

Before you tell me I’m crazy, here’s the logic.

For high earners, retirement accounts are the default move:
	•	reduce taxable income today
	•	invest in markets for decades
	•	defer taxes until later

Sounds clean.

But there’s one variable almost nobody explicitly prices in:

𝗧𝗵𝗲 𝘁𝗶𝗺𝗲 𝘃𝗮𝗹𝘂𝗲 𝗼𝗳 𝗺𝗼𝗻𝗲𝘆. 

$100 today isn't worth the same as $100 when you're 60. All else being equal, you'd always want that $100 earlier vs later.

Different people have different discount rates. Most people would be totally fine giving up an extra $5k today for an extra $15k in their 401k when they're 60.

My personal discount rate is very high.

I’m not optimizing for “retire comfortably at 60.” I’m optimizing for:
	•	flexibility
	•	compounding faster today
	•	deploying capital into opportunities I control

To me, an extra $15k at 60 is worth close to $0.

This, combined with the fact that you can get tax free returns with real estate without locking up your capital until you're 60, makes retirement accounts even less appealing to me personally.

𝗧𝗼 𝗯𝗲 𝗰𝗹𝗲𝗮𝗿: 𝗳𝗼𝗿 𝗺𝗼𝘀𝘁 𝗽𝗲𝗼𝗽𝗹𝗲, 𝗿𝗲𝘁𝗶𝗿𝗲𝗺𝗲𝗻𝘁 𝗮𝗰𝗰𝗼𝘂𝗻𝘁𝘀 𝗺𝗮𝗸𝗲 𝘀𝗲𝗻𝘀𝗲, so don't go and cash out your accounts immediately. 

In fact, they're particularly useful if you get employer match (which is why I had a 401k in the first place).

But if you’re entrepreneurial, capital-constrained, or you just have a high discount rate like me, it’s worth asking:

Is the retirement account optimizing your wealth, or restricting your options?

Principal of a $69M Debt Fund Distributing ~20% Annualized | Investor Loans on 1-20 unit Residential Properties | Ex SWE @ Meta

Here's what it actually means to lose 90% in a private investment—and why you should respect Warren Buffett's first rule of investing.

For the uninitiated, Buffett's first two rules of investing are:

1. Never lose money.
2. Never forget Rule No. 1. 

It's not just a cute saying, though. There's a very straightforward way to think through this mathematically that makes this the obvious primary consideration when you're investing.

When most people think about investment loss, most people have experience with it in the context of stocks, and more specifically their 401ks, which are mainly invested in indices.

If your stocks go down 3% one year, it doesn't really matter since they can easily rise 5% or more the next year and more than make up for it.

However, the thing about losses is that they're 𝗲𝘅𝗽𝗼𝗻𝗲𝗻𝘁𝗶𝗮𝗹𝗹𝘆 𝗵𝗮𝗿𝗱𝗲𝗿 to recover from the greater they are. 

If you lose 3%, you only need to make 3.1% to break even.
If you lose 10%, you need to make 11%.
If you lose 25%, you need to make 33%.
And if you lose 𝟵𝟬%, 𝘆𝗼𝘂 𝗻𝗲𝗲𝗱 𝘁𝗼 𝟭𝟬𝘅 𝘆𝗼𝘂𝗿 𝗺𝗼𝗻𝗲𝘆 𝘁𝗼 𝗯𝗿𝗲𝗮𝗸 𝗲𝘃𝗲𝗻.

If you're used to index investing in stocks, you 𝘵𝘺𝘱𝘪𝘤𝘢𝘭𝘭𝘺 don't need to worry about losses greater than 10%.

But when you're investing in an illiquid, leveraged alternative investment like multifamily? It's a real consideration.

Based on the things I've read on LinkedIn over the past few years, some multifamily LPs have already been burned (whether they know it yet or not), and will likely be turned off from investing in multifamily for the next few years.

Ironically, if the practice of widespread extending and pretending by lenders ends in 2026, the later part of this year might be one of the best times to buy multifamily.

If protecting your downside isn't your first consideration when investing in alternatives, you might want to rethink your approach.

Here's a statistic so insane that I literally didn't believe it at first: 𝟰𝟬% of people earning > 𝗵𝗮𝗹𝗳 𝗮 𝗺𝗶𝗹𝗹𝗶𝗼𝗻 𝗱𝗼𝗹𝗹𝗮𝗿𝘀 live 𝗽𝗮𝘆𝗰𝗵𝗲𝗰𝗸 𝘁𝗼 𝗽𝗮𝘆𝗰𝗵𝗲𝗰𝗸.

And the even crazier part is that this is higher than the $200k-$300k income band...according to the chart below, only 16% of those earners live paycheck to paycheck.

There are a lot of surface-level explanations for this: 
- higher taxes
- different expenses (like private school for the kids)
- illiquidity
- and more

But here's another very important component that doesn't really get talked about, along with an important lesson that we can take away from it.

Most people tend to spend most of their time with people in a similar socioeconomic situation as them. 

If you're an upper middle class tech worker, most of your friends and coworkers are also upper middle class tech workers.

If you're a retail worker at a department store, most of your peers are likely working similar jobs and making roughly the same amount as you.

However, if you're making more than $500k/year, this breaks down. 

Let's consider an imaginary hedge fund: 
- A junior quant might earn $600k.
- Their portfolio manager might earn $4M.
- The founder might earn $30M+ in a good year.
- And that founder is raising from LPs with more than a $2B net worth.

If you think upper middle class lifestyle creep is bad, imagine how much worse it would be if your peers made 10x what you do. 

Lifestyle creep is deadly because it converts a 𝘩𝘪𝘨𝘩 𝘪𝘯𝘤𝘰𝘮𝘦 into 𝘩𝘪𝘨𝘩 𝘧𝘪𝘹𝘦𝘥 𝘤𝘰𝘴𝘵𝘴.

I think an easy strategy to make sure this doesn't happen to you is to build up cash flow from investments and constrain your non-essential spending to your investment income, not your earned income.

Of course, that's way easier said than done, but if it was easy everyone would be doing it.

Any other ideas on how to mitigate lifestyle creep?

Retiring on stocks sounds insane to me. What am I missing?

To be clear: I’m not anti-stocks. I think stocks are a great way to build wealth, and they obviously belong in most portfolios.

I’m talking about the default retirement playbook:
1. Build a stock/bond portfolio with some predetermined split
2. Retire
3. Sell off principal every year to cover expenses

If you follow personal finance content, you’ve definitely heard of the 4% rule—the idea that you can withdraw ~4% of your portfolio annually and be “fine.”

This rule is touted by personal finance gurus like it's a law of physics when it's really just a historical backtest with some assumptions (that don't always hold):

𝗧𝗶𝗺𝗲𝗹𝗶𝗻𝗲
The Trinity Study (where the 4% rule comes from) assumes a ~30 year retirement. 

People are living longer, and many want the option to retire earlier. The longer the time horizon, the higher the probability of a bad outcome.

𝗘𝘅𝗽𝗲𝗻𝘀𝗲 𝗜𝗻𝗳𝗹𝗮𝘁𝗶𝗼𝗻
The Trinity Study assumes your expenses rise with CPI. In the real world, expenses aren’t that clean. As you get older, healthcare costs will almost certainly grow faster than inflation.

𝗦𝗲𝗾𝘂𝗲𝗻𝗰𝗲 𝗼𝗳 𝗥𝗲𝘁𝘂𝗿𝗻 𝗥𝗶𝘀𝗸
If the market rips upward right after you retire, this strategy works beautifully. But if you retire into a crash, you can end up selling meaningful chunks of your portfolio at the bottom—which can permanently reduce what your portfolio is capable of sustaining, even if markets eventually recover.

So here’s my genuine question:

Why is the default retirement advice still so centered on “sell principal from stocks + bonds”…
when there are other asset classes that can generate cash flow without systematically liquidating principal?

As another disclaimer, this isn’t a “stocks are bad and you should invest in real estate instead” post.

I’m genuinely trying to understand why mainstream personal finance rarely discusses retirement models based on cash-flowing assets (real estate, private credit, energy, etc.) instead of treating them like niche or optional.

If someone has another perspective on this I'd love to hear it.

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