Helping Changemakers Build Wealth Like They Build Solutions: With Purpose | Ex-Apple Engineer

I'm the real estate sponsor who's actually built a building. A lot of them. 

So I don't outsource my due diligence. I am the due diligence.

For 20 years my engineering ensured buildings didn't fail, they thrived.

And 9 of those years I was Apple's most trusted building engineer leading the design of their global retail store portfolio. 300+ stores. 20+ countries. Award-winning buildings that millions of people visit daily. Before Apple, New York City skyscrapers and large scale renewable energy. In all, $10B+ in projects where failure wasn't an option.

Then I burned out building someone else's empire.

In 2023, I walked away from Apple stock options I could've retired on to build a future I controlled for people that trust me, not people who own me.

Type 1 diabetic for 30+ years. Father of 2 young kids. I know what it means when every day counts—and I build for people who want their time back—not another job disguised as passive income.

You won't hear me pitch forced appreciation through rent increases you can't control. That's not engineering. That's gambling.

I obsess over operations and building systems. That's where buildings make and lose money—and after 20 years of engineering for companies that refused to accept failure, I know where to look.

With global economic uncertainty, my thesis is double edged. I keep my capital close with private lending—short duration, high yield, high velocity. Capital ready to move for when the next downturn hits. Because cashflow pays the bills and capital is power.

But wealth isn't built short term. Real assets with long horizons should be the foundation you build to last generations. And resilience isn't "green," it's the only smart business that will protect your investment.

I invest for what matters: people. If you care about where your money goes and not just how much it makes then follow along.

Ready to build your real estate wealth? 
DM me "BUILD" and let's engineer your real estate portfolio together.

Weekly insights: dropsofchange.substack.com

Jon Weiskopf, P.E.

My dad died when I was 13.
I've counted time ever since.

He was 51.
Type 1 diabetic.
Same disease I've managed since age 11.

Watching him go taught me something
no business school ever could:

Time isn't renewable.

You don't get days back.
You don't get hours back.
You don't get moments with your kids back.

That's why I left Apple.

Not because the money was bad.
The money was great.
The stock options were life-changing.

But I was trading time for money.
And time was the thing I couldn't replace.

Now I build differently.

Private lending for cash flow—money that works without me.
Real assets for legacy—wealth that outlasts me.

Cashflow pays the bills.
Appreciation builds what I leave behind.

I need both.
Because I'm not just building a portfolio.
I'm building a life I actually get to live.

>> What would you build if you knew your time was limited?

========
I'm Jon — Engineer. Builder. Now investor. I know where risk hides.

DM me "BUILD" and let's engineer your real estate portfolio.

Build wealth before doubt builds nothing.

From the outside, Apple looks flawless.
Inside?

Apple wrestles with the same trade-offs every large operator does.

Reactive maintenance looks cheaper.
Until you measure the real cost.

Apple Retail had a policy to minimize capex.
Instead of proactively replacing HVAC systems,
The directive was to run equipment until failure.

That policy wasn’t driven by Facilities.
It was governed by Finance.

On a spreadsheet, it made sense.
Deferred spend looks like savings.

But here’s what never made the calculation:
The cost of avoidance.

When HVAC failed, stores closed.
Customer experience suffered.
Revenue disappeared — quietly and instantly.

Those costs never showed up in the capex model.

I see the exact same mistake in multifamily.

Owners say,
“I’ll just wait until it breaks.”

But when systems fail:
Maintenance tickets pile up.

Residents get frustrated.

Move-outs increase.

(And maintenance is the #1 reason residents leave.)

Yes, proactive upgrades cost money.
But reactive maintenance costs trust, stability, and NOI.

The real lesson:
If Finance optimizes in isolation, operations pay the price.

Great operators don’t just ask:
“What does this cost today?”

They ask:
“What does avoiding this cost us tomorrow?”

Because in real estate —
The most expensive problems are the ones you pretend don’t exist.

>> Are you modeling maintenance as an expense… or as a risk multiplier?

========
I’m Jon — Engineering passive income for you like I engineered Apple’s global retail store portfolio.

Find my Featured section to connect.

Short-duration debt + GP shares = aligned incentives.


We closed a loan and a multifamily acquisition at the same time.

That’s not an accident.
That’s structure.

The deal was a 152-unit Class C property in Kansas City — one of my favorite markets.
Off-market.
Strong value-add.
Targeting a ~40% valuation lift after capex.
Projected 10% cash-on-cash with a 3-year hold.

Here’s how we structured it:

We provided an EMD loan to an up-and-coming operator.
Short duration.
Clear execution plan.
And because alignment matters, we didn’t stop at the loan.

We received GP shares in the deal.

Why?
Because when capital participates on both sides of the stack, incentives change.

To further de-risk the loan, we also helped raise equity —
giving our investors exposure to both:
The acquisition upside, and
The ownership economics.

The results:
- Loan duration: 2.5 months
- Loan return: ~30% ARR
- Equity position: long-term upside through ownership

That’s how we support emerging operators and protect investor capital.

We don’t just wire money.
We help close deals.
We help structure wins.

Because the best capital isn’t passive.
It’s partnered.

>>> Are your investments structured for alignment — or just yield?

========
I’m Jon — Engineering passive income for you like I engineered Apple’s global retail store portfolio.

Find my Featured section to connect.

Apple demanded details no one sees.
That obsession stayed.

In Cupertino,
we would debate the radius of a corner.
The exact hue of an employee t-shirt.
The gap between wall panels measured in millimeters (3mm to be exact)

Details that 99% of customers never notice.

But Apple believed something:

Excellence isn't what people see.
It's about what you know is there.

That obsession 

Cost time.
It cost money.
It frustrated vendors who wanted "good enough."

But it built something:

Stores that feel different—
even if you can't explain why.

I brought that to real estate.

I notice the deferred caulking around windows.
The drainage slope that's 1% instead of 2%.
The HVAC duct that's undersized.

Details most sponsors never see.
Details that become expensive problems later.

Is it worth it?

Only if you believe the details compound.
I do.

Most investors underwrite the spreadsheet.
I underwrite the building—down to the millimeter.

>> What details are hiding in your investments?

========
I'm Jon — Engineer. Builder. Now investor. I know where risk hides.

DM me "BUILD" and let's engineer your real estate portfolio.

Two loans funded and returned in under 2 weeks each.
Velocity by design.

When we launched the private debt fund,
I had one question:

How fast can capital cycle
Without sacrificing discipline?

The answer came quickly.

Loan 2: Closed in 2 days.
Loan 3: Closed in 13 days.

Not because we rushed.
Because we systematized.

Here's what made it possible:

→ Pre-defined underwriting criteria
→ Legal docs templated and ready
→ Borrower requirements non-negotiable
→ Decision authority clear

Most funds take 30-60 days to close.
We take 7-14.

That's not recklessness.
That's engineering applied to capital deployment.

Every day a loan sits in underwriting,
returns erode.
Every week of delay,
velocity dies.

Cashflow buys time.
Velocity multiplies it.

4 loans initiated in 60 days.
2 already repaid and recycled.

The system works.

>> How much return are you losing to slow deployment?

========
I'm Jon — Engineer. Builder. Now investor. I know where risk hides.

DM me "BUILD" and let's engineer your real estate portfolio.

My average loan lasts 4.3 months.
The average RE deal lasts 5 years. Which do you prefer?

Most investors still think wealth is built in years, not quarters.

That belief comes from traditional real estate thinking.
Buy.
Hold.
Wait.

Private credit works on a different clock.

Short duration reduces exposure.
Faster repayment increases control.
Capital velocity quietly compounds.

When capital returns in months instead of years, risk becomes measurable instead of theoretical.

You don’t need to predict markets.
You need to manage timelines.

This is why we obsess over structure.
Clear exits.
Defined milestones.
Borrowers with something to lose.

Quarterly cycles don’t feel exciting.
But they outperform quietly.

>>> Is your capital waiting—or working right now?

========
I’m Jon — Engineering passive income for you like I engineered Apple’s global retail store portfolio.

Find my Featured section to connect.

Recession fears are rising.
Is your portfolio stress-tested?

Headlines are getting louder:
"Economic uncertainty ahead."
"Prepare for downturn."
"Markets brace for impact."

Most investors read these headlines
and freeze.

Analysis paralysis sets in.
Capital sits on the sidelines.
Opportunities pass.

I take a different approach.

I stress-test.

→ What happens if vacancy hits 15%?
→ What happens if rates stay elevated?
→ What happens if rent growth goes flat?
→ Can this building survive 24 months of pressure?

If the answer is no,
I don't invest.

If the answer is yes,
I move—while others wait.

Recessions expose weakness.
They don't create it.

The weakness was always there.
Hidden by strong markets.
Masked by easy money.

Resilience isn't green.
It's risk management.

And risk management starts before you write the check—
not after the downturn hits.

>> Have you stress-tested your portfolio for what's coming?

========
I'm Jon — Engineer. Builder. Now investor. I know where risk hides.

DM me "BUILD" and let's engineer your real estate portfolio.

Zero investor losses on private loans.
Engineering, not luck.

14 loans.
$3.1M deployed.
0 losses.

Some people would call that lucky.

I call it engineered.

Here's what we do that most lenders don't:

→ LTV caps at 65-70% (room for error)
→ Borrower exit strategy verified (not assumed)
→ Collateral personally inspected (not outsourced)
→ Loan duration kept short (reduced exposure)

Luck is hoping the deal works.
Engineering is structuring so it doesn't have to be perfect.

Every loan assumes something will go wrong.
Then we build protection for it.

The borrower struggles? Collateral covers us.
The market softens? Short duration limits exposure.
The property has issues? We found them before funding.

Most investors underwrite the spreadsheet.
I underwrite the downside.

Because zero losses isn't about avoiding risk.
It's about pricing it correctly.

>> Is your portfolio built on luck—or on engineering?

========
I'm Jon — Engineer. Builder. Now investor. I know where risk hides.

DM me "BUILD" and let's engineer your real estate portfolio.

3 loans in 60 days.
2 closed. $0 losses.

Here’s how…

That's not luck.
That's velocity by design.

Most private lenders take 30, 60 even 90 days to close a loan.
They screen for months.
Deploy for years.

We engineered a different system.

→ Strict underwriting criteria (before we ever see a deal)
→ Collateral requirements that protect downside

→ 48-hour decision timeline

The result?

Capital that moves.
Risk that's contained.

Returns that compound.

3 loans in our first 60 days of Our Debt Fund operating.
Not because we lowered standards.
Because we systematized them.

When your criteria are clear,
decisions get fast.
When decisions are fast,
capital works harder.

Most investors underwrite the spreadsheet.
I underwrite the building—and the borrower's exit.

That's why we can move quickly
without moving recklessly.

>> Are your returns built on hope—or on engineered velocity?

========
I'm Jon — Engineer. Builder. Now investor. I know where risk hides.

DM me "BUILD" and let's engineer your real estate portfolio.

20 countries. 20 ways to build.
Same physics.

Tokyo contractors frame differently than London crews.
Dubai specifications look nothing like São Paulo standards.
Every culture has its own construction DNA.

But here's what I learned in 9 years engineering Apple's global retail:

The building doesn't care about culture.
It cares about water management.
It cares about thermal movement.
It cares about load paths.

Physics is the great equalizer.

I've watched brilliant teams in Munich, Chongqing, and Kyoto
solve the same problems
with completely different approaches.

Both worked.
Because both respected the fundamentals.

That's what I bring to real estate investing now.

Not opinions about markets.
Not theories about appreciation.

Just 20 years of understanding
what makes buildings stand—
and what makes them fail.

Different markets. Different deals.
Same engineering discipline.

>> What would change if you could see what the building sees?

========
I'm Jon — Engineer. Builder. Now investor. I know where risk hides.

DM me "BUILD" and let's engineer your real estate portfolio.

The dollar is weakening. Beware.
But land doesn't disappear.

Stock prices swing.

Currency fluctuates.
Bond yields shift with every Fed meeting.

But the units in my portfolio?
Still standing.
Still housing residents.
Still generating rent.

Real assets have a quality
that paper assets don't:

They exist.

When inflation erodes purchasing power,
real estate adjusts.
Rents move with the market.
Replacement costs rise.
The asset becomes worth more in nominal terms.

That's not speculation.
That's physics meeting economics.

I'm not predicting a recession.
I'm not betting on dollar collapse.

I'm positioning for resilience.

Private lending for short-term velocity.
Real assets for long-term wealth preservation.

Because when uncertainty rises,
I want to own things—
not promises about things.

Resilience isn't green.
It's risk management.

>> If the dollar drops 20% tomorrow, what happens to your portfolio?

========
I'm Jon — Engineer. Builder. Now investor. I know where risk hides.

DM me "BUILD" and let's engineer your real estate portfolio.

An investor asked why no promises.
I showed track record.

"What returns can you guarantee?"

I get this question a lot.
And I understand why.

People want certainty.
They want someone to tell them it's going to be okay.
They want promises.

I don't make promises.
I show data.

→ 11 private loans
→ $2.3M deployed
→ 0 losses
→ 50.3% average annualized return

That's not a guarantee.
That's a track record.

Guarantees are marketing.
Track records are evidence.

Any sponsor can promise you 15% returns.
Few can show you 15 deals with 0 losses.

I'd rather under-promise and over-deliver
than make commitments I can't control.

Because real estate has variables.
Markets shift.
Tenants leave.
Things break.

What I can control:
→ How I underwrite
→ How I manage risk
→ How I communicate

Most investors underwrite the spreadsheet.
I underwrite the building—and my own track record.

>> Would you rather have promises or proof?

========
I'm Jon — Engineer. Builder. Now investor. I know where risk hides.

DM me "BUILD" and let's engineer your real estate portfolio.

We initiated 4 loans before most funds close one.


Traditional private lending works like this:

→ Source a deal (2-4 weeks)
→ Underwrite (4-6 weeks)
→ Legal review (1-2 weeks)
→ Close (1 week)

8-10 weeks for a single loan.
Then start over.

We built a different system:

→ Pre-qualified borrower network
→ Standardized underwriting criteria
→ Templated legal documents
→ 48-hour decision authority

The result?

4 loans initiated in 60 days.
While other funds were still closing their first.

This isn't about cutting corners.
It's about eliminating friction.

Every day of delay is return erosion.
Every week of process is velocity lost.

Cashflow buys time.
Velocity multiplies it.

When capital moves faster,
it works harder.
When it works harder,
returns compound.

Most investors are patient.
I'm impatient—by design.

>> How fast does your capital actually move?

========
I'm Jon — Engineer. Builder. Now investor. I know where risk hides.

DM me "BUILD" and let's engineer your real estate portfolio.

The horror of underestimated rehab costs…


Early in my days,
I budgeted my house rehab based on the contractor's estimate.

$157,000 rehab budget.
Seemed reasonable.
Numbers worked.

90 days in, we were at $196,000.
And not done.

Final cost: $213,000.

36% over budget.
Stress, anger.
Lesson learned.

Here's what I missed:

→ I underestimated hidden conditions
→ I assumed the contractor's timeline was realistic

Now every deal includes:

→ 20% contingency minimum
→ Timeline buffers that seem crazy

Mistakes are tuition.
But only if you change the system.

That deal taught me more about risk
than any spreadsheet ever could.

Because risk isn't in the numbers.
It's in the assumptions behind them.

>> What's the most expensive lesson you've learned in real estate?

========
I'm Jon — Engineer. Builder. Now investor. I know where risk hides.

DM me "BUILD" and let's engineer your real estate portfolio.

I don't buy inspection reports. 
I write them.

Most investors get a 40-page inspection report.
Skim the summary.
Check the "major concerns" section.
Move on.

They miss everything that matters.

Because inspection reports are written for liability—
not for investment decisions.

Here's what I do differently:

I walk the roof myself.
I check the HVAC units myself.
I look for water staining patterns myself.
I calculate remaining useful life myself.

Not because I don't trust inspectors.
Because I know what they're trained to see—
and what they're not.

20 years of engineering taught me:

The building speaks.
Most people just don't know the language.

A hairline crack in a foundation wall?
Could be settlement (normal).
Could be structural movement (expensive).

The difference is in the pattern.
And patterns take experience to read.

Most investors underwrite the spreadsheet.
I underwrite the building.

>> Who's reading the buildings in your portfolio?

========
I'm Jon — Engineer. Builder. Now investor. I know where risk hides.

DM me "BUILD" and let's engineer your real estate portfolio.

Recessions expose deferred maintenance.
Here's how to spot it.

When markets are strong,
buildings hide their problems.

High occupancy masks deferred repairs.
Strong rent rolls cover up capital needs.
Cash flow papers over cracks—literally.

Then the downturn hits.

Suddenly that "stable" asset
Needs a new roof you didn't budget for.

The HVAC that was "fine" fails in July.
The foundation issue becomes a foundation crisis.

Here's what I look for before I invest $1:

→ Roof age and condition (the actual membrane)
→ Water intrusion patterns (staining tells stories)
→ Repeated repairs to the same unit (can kicked down the road)

→ HVAC remaining useful life (and replacement cost at today's prices)

Most investors read the pro forma.
I read the building.

Because the building tells you
what the spreadsheet is hiding.

20 years of engineering taught me:
Deferred maintenance doesn't disappear.
It compounds.

And recessions collect the bill.

>> Before your next investment, ask: What is this building hiding?

========
I'm Jon — Engineer. Builder. Now investor. I know where risk hides.

DM me "BUILD" and let's engineer your real estate portfolio.

Before I invest $1, I walk the roof.
Not everyone does.

Here's what most investors do:

Read the inspection report.
Check the "roof" section.
See "5-7 years remaining useful life."
Move on.

Here's what I do:

I go up there.

And I look for what the report doesn't say:

→ Ponding water patterns (drainage issues)
→ Soft spots reveal water beneath (future leak sources)
→ Flashing details at walls and curbs (water entry points)
→ HVAC unit placement and condition (roof loading and leaks)

→ Thermal imaging camera shows the hidden water damage below.

A roof replacement is $8-15/sq ft.
On a 50,000 sq ft building, that's $400,000-$750,000.

One missed assessment.
Returns destroyed.

20 years of engineering taught me:

The roof is the building's first defense.
And it's the first thing most investors ignore.

Most investors underwrite the spreadsheet.
I underwrite the building—starting from the top.

>> When's the last time you actually walked a roof before investing?

========
I'm Jon — Engineer. Builder. Now investor. I know where risk hides.

DM me "BUILD" and let's engineer your real estate portfolio.

Raised $30 MM in capital for real estate through LinkedIn and Guest Podcasting | Posts about Real Estate, Writing, and Audience Building

99% of Real Estate LinkedIn is Chat GPT posts and noise.

There's a better way to stand out online ⤵️

If this sounds like you:

❌ Lack of capital
❌ Feeling tired and burned out
❌ Not growing your presence online

Now, imagine this:

✅ Securing more deals
✅ Successfully raising $5 million in capital
✅ Having a loyal following that knows, likes, and trusts you

If you're a 6-figure real estate entrepreneur who's serious about raising more capital and closing more deals, join my free newsletter, Digital Leverage. 

You'll be in good company with over 300+ entrepreneurs who are making their mark online. 

(See featured section above ⤴️)

Matthew Baltzell 🌴

Matt Damon said Netflix has to repeat the plot 3–4 times because people are on their phones (Now apply that to investors.)



If you think...

- “I already explained the deal”

- “They saw the deck”

- “We covered this on the last call”

You’re overestimating attention.

Investors are scanning, not studying.

They’re comparing you to 5 other deals this week.

They remember patterns, not paragraphs.

That’s why the best sponsors:

- Repeat the thesis

- Reinforce the why now

- Re anchor the risk story

- Re state the downside protection

Same message.
Different format.
Every touchpoint.

Call.
 Deck.
  Email.
  Podcast.
   Follow-up.

If Netflix needs repetition to keep viewers…
...You need it to move capital.

If your deal feels “obvious” to you,

it’s probably still unclear to them.

Matthew Baltzell

$20M+ Raised | LP Pipeline Systems for $20M–$100M Real Estate & PE Sponsors | Build Trust, Fill Rounds, Raise Without Resetting

Everyone’s mad about housing...but no one wants to admit it’s a zero sum game...

Young people want cheaper homes.

Boomers want prices to keep going up forever.

Then Donald Trump said the quiet part out loud:

You can’t make housing affordable without nuking existing wealth.

And suddenly everyone clutched their pearls.

But here’s the truth no one wants to sit with:

The system is working exactly as designed.
It protects asset holders.
Not hopeful buyers.

So if you’re under 40 and your plan is:

- “Wait for prices to fall”

- “Vote harder”

- “Complain on X”

Good luck. For real.

Because nobody is coming to make things cheaper and keep everyone rich.

That math doesn’t math.

The real move?
Bet on yourself.

Not vibes.
Not manifesting.
Not outrage.

Skills that compound.
Income that scales.
Ownership early even if it’s uncomfortable.

Because the fastest way out isn’t fixing the system.

It’s becoming antifragile inside it.

Harsh? Maybe.
True? 1,000%

Agree or disagree?

$7,000 staging job replaced by a $12 AI render. 

Here’s what happens next...

Look again.

Left → AI staging.
Right → a $3,000/month vacant liability pretending it’s “almost ready.”

Buyers decide in 8 seconds.

Physical staging costs you:

Trucks
Movers
Insurance
Two days of chaos
Thousands in cash

AI staging costs you:

$12
12 seconds
A mouse click

That’s it!

Virtual staging isn’t some “future trend.”

It already won.
It’s cheaper.
It’s faster.
 
And it converts better than your perfectly fluffed couch ever will.

The investors who pivot now?

They won’t just win more deals.

They’ll take them—quietly—while everyone else is still waiting on the movers.

Agree or disagree?

$20M+ Raised | LP Pipeline Systems for Real Estate & PE Firms | Build Trust, Fill Deals, Raise Faster

At a certain level, capital raising stops being about persuasion...


It becomes about positioning.

I’ve noticed a common ceiling among capable sponsors around $30–$50MM AUM.

They’re competent.
They have a track record.
They can raise capital.

But their conversations still subtly frame LPs as the senior party.

That framing breaks the raise.

Sophisticated capital doesn’t want to be chased.
And it doesn’t want to be sold.

It wants to be invited into something credible.

The dynamic shifts when capital is treated as an allocation decision between peers - not a favor.

The strongest raises don’t feel like asks.

They sound like...

- Here’s what we’re building.
- Here’s who it fits.
- Decide if this belongs in your portfolio.

Make sense?

Equal footing.
Clear standards.
No urgency theater.

At scale, capital raising is less about convincing
and more about filtering.

The moment a sponsor stops signaling need
and starts signaling inevitability,
the quality of capital changes.

Same deals. Different posture. Very different outcomes.

I just changed my LinkedIn followers to 100,000. Watch how.


Six seconds later… 100k followers.

Here’s what didn’t change:

• No new capital commitments
• No wires hitting the account
• No new investors

Because nothing about their visibility actually changed.

• Same fund.
• Same credibility.
• Same bank balance.

Same Same but NOT different. 

That’s the problem with how most people think about capital raising.

LPs don’t invest because your follower count looks impressive.

They invest because:

They trust you
They understand the deal
They’ve seen consistency over time

I’ve watched sponsors chase vanity metrics…
…and then struggle to fill a $5M raise.

Followers are a signal.
Trust is the currency.

If your capital raising strategy depends on optics instead of relationships,
you’re building noise not conviction.

Real capital is raised through:

• Repeated exposure
• Clear communication
• Direct conversations
• Long term credibility

Not a number that can be edited in the source code.

If you’re a sponsor raising (or planning to raise) capital and this resonated, happy to share what actually converts attention into committed LPs.

Markets aren’t “up.”
The measuring stick is broken.


Ray Dalio said the quiet part out loud:

“If you depreciate the money, it makes everything look like it’s going up.”

The problem…

Most people measure success in nominal numbers.

Revenue up.
Portfolio up.
Valuation up.

Looks like progress.

Think about it.

Same house.
Double the price?

Get out of here.

Inflation is a savage disguise.

It makes weak businesses look strong.
It rewards leverage over discipline.
It convinces people they’re winning… while their purchasing power shrinks.

That’s how you get:

• “Growing” companies with no margin expansion
• Record highs that feel worse at the grocery store
• Operators confusing price appreciation with value creation

This is where people blow up in the next cycle.

Change the scoreboard.

Real operators and serious investors optimize for:

• Free cash flow, not paper gains
• Pricing power, not cheap money
• Businesses that work when capital isn’t easy

A simple test:

Would this still work if money wasn’t cheap?

If the answer is no, it’s not a business.
It’s a trade riding monetary policy.

The next decade won’t reward hype.
It’ll reward what actually works.

Where do you see “fake growth” showing up right now?

I asked a LinkedIn connection for $100,000. 

His response exposed everything wrong with capital raising on LinkedIn.


Are your DMs full of strangers pitch-slapping you deals?

Same.

Most of them go straight to the “Other” folder.

Unread.
Unanswered.
Emotionally deleted.

Except this one time.

A guy I was connected with kept following up about his real estate deal.

Message after message.
Soft nudges.
Hard “just circling back.”

I never replied.

So I decided to play along.

I wrote back:

“Would you be open to investing $100,000?”

He replied instantly.

“Sorry...I don’t really know you.”

There it is.

The irony is undefeated.

You can’t cold DM strangers for capital…
...and then be surprised when they don’t trust you.

Deals don’t create trust.
Trust creates deals.

Capital doesn’t move because your pro forma is tight.
It moves because you are familiar, credible, and respected.

If you’re serious about raising money:

- Stop leading with the deal

- Start leading with trust

- And show up long before the ask

Because capital doesn’t flow through inboxes.

It flows through relationships.

If you’re a real estate investor who wants more investor visibility and plans to raise $3M+ on your next raise, DM me “real estate.”

𝗜’𝘃𝗲 𝗴𝗼𝘁 𝘀𝗼𝗺𝗲𝘁𝗵𝗶𝗻𝗴 𝗙𝗥𝗘𝗘 𝗳𝗼𝗿 𝘆𝗼𝘂.

I stress tested a great looking Offering Memorandum with ChatGPT and found this surprising...


I asked it one question:

“Why does this deal look better on paper than it will in real life?”

It flagged 4 things the OM made look harmless...but aren’t.

𝟭. “𝗖𝗼𝗻𝘀𝗲𝗿𝘃𝗮𝘁𝗶𝘃𝗲” 𝗿𝗲𝗻𝘁 𝗴𝗿𝗼𝘄𝘁𝗵 𝗱𝗼𝗶𝗻𝗴 𝗮𝗹𝗹 𝘁𝗵𝗲 𝘄𝗼𝗿𝗸

2–3% annual growth doesn’t sound aggressive.
Until you realize it’s the only reason the IRR works.

If leasing slows, the deal quietly breaks.

𝟮. 𝗔 𝗽𝗿𝗼 𝗳𝗼𝗿𝗺𝗮 𝗲𝘅𝗽𝗲𝗻𝘀𝗲 𝗿𝗮𝘁𝗶𝗼 𝘁𝗵𝗮𝘁’𝘀 𝗻𝗲𝘃𝗲𝗿 𝗲𝘅𝗶𝘀𝘁𝗲𝗱

The OM showed a cleaner expense line than the property has ever produced.

It wasn’t fraud.
It was optimism, dressed up as efficiency.

𝟯. 𝗗𝗲𝗯𝘁 𝗮𝘀𝘀𝘂𝗺𝗽𝘁𝗶𝗼𝗻𝘀 𝗳𝗿𝗼𝘇𝗲𝗻 𝗶𝗻 𝘁𝗶𝗺𝗲

The numbers only worked at yesterday’s rates.

No sensitivity.
No downside case.
Just vibes.

𝟰. 𝗔 𝘀𝗺𝗼𝗼𝘁𝗵 𝗲𝘅𝗶𝘁 𝗰𝗮𝗽 𝗱𝗼𝗶𝗻𝗴 𝗵𝗲𝗮𝘃𝘆 𝗹𝗶𝗳𝘁𝗶𝗻𝗴

Half the projected return came from the exit, not operations.

That’s not "value add."
That’s hoping the next buyer is more optimistic than you.

None of this was hidden.

It just wasn’t emphasized.

That’s the trick with great looking OMs...

They don’t lie. They distract.

If you only read the upside, you’re underwriting the broker NOT the asset.

Sometimes it takes a robot with no commission to slow you down (deep sigh)

I spoke with an operator who needed to raise $3M in six months…but the warning signs arrived faster than the pitch deck.


On paper?
Easy yes.

In reality?
I sprinted the other direction.

Here’s why 👇

𝗥𝗲𝗱 𝗳𝗹𝗮𝗴 #𝟭: 𝗧𝗵𝗲𝘆 𝗵𝗮𝗱𝗻’𝘁 𝗚𝗼𝗼𝗴𝗹𝗲𝗱 𝗺𝗲.

Not my business.
Not my background.
Not even a “Hey, I saw you do X.”

Just showed up like,
“So… what do you do exactly?”

If you won’t do 5 minutes of homework on the person raising your capital.

I assume you underwrite deals the same way.

Vibes. Hope. Prayer.

𝗥𝗲𝗱 𝗳𝗹𝗮𝗴 #𝟮: 𝗖𝗼𝗺𝗺𝘂𝗻𝗶𝗰𝗮𝘁𝗶𝗼𝗻 𝗯𝘆 𝗰𝗮𝗿𝗿𝗶𝗲𝗿 𝗽𝗶𝗴𝗲𝗼𝗻.

Days between replies.
Same questions.
Same explanations.

Every message felt like the first date in 50 First Dates.

At some point I wondered:
Am I talking to the operator…
their VA…

or an AI trained exclusively on confusion?

Trust doesn’t survive lag, ambiguity, or “Sorry just circling back.”

𝗥𝗲𝗱 𝗳𝗹𝗮𝗴 #𝟯: 𝗧𝗵𝗲 𝗱𝗶𝘀𝗮𝗽𝗽𝗲𝗮𝗿𝗶𝗻𝗴 𝗱𝗲𝗮𝗹.

“I sent you the info.”

They didn’t.

If follow-through is optional before you touch investor money,
I already know what happens after the wire hits.

So yes...I turned down a deal that would’ve paid very well.

And no...I didn’t hesitate.

Because capital raising is just a magnifying glass.
It doesn’t fix dysfunction.
It puts it on a billboard.

Money is easy to replace.
Bad operators are not.

𝘞𝘩𝘢𝘵’𝘴 𝘵𝘩𝘦 𝘧𝘢𝘴𝘵𝘦𝘴𝘵 𝘳𝘦𝘥 𝘧𝘭𝘢𝘨 𝘵𝘩𝘢𝘵 𝘮𝘢𝘬𝘦𝘴 𝘺𝘰𝘶 𝘸𝘢𝘭𝘬 𝘯𝘰 𝘦𝘹𝘱𝘭𝘢𝘯𝘢𝘵𝘪𝘰𝘯 𝘯𝘦𝘦𝘥𝘦𝘥?

Waste Management might be one of the best AI businesses in America.


Most people miss it because they think it’s just a trash company.

Yes, they haul waste.

But the real advantage is what they already control...

• Irreplaceable landfill assets
• Long term municipal contracts
• Route density no startup can replicate

Now add AI.

AI doesn’t replace Waste Management.

It tightens the machine.

• Route optimization → lower fuel and labor costs
• Predictive maintenance → fewer breakdowns
• Automation → higher margins on the same assets

The assets don’t change.

The efficiency curve bends upward.

This is the part of the AI conversation that gets ignored.

AI doesn’t just create new software companies.

It widens the gap between asset owners and everyone else.

As an investor, I’m less interested in...

• AI wrappers
• Chatbots with churn
• Tools that can be cloned in a weekend

And more interested in...

• Asset-heavy businesses with data moats
• Physical infrastructure AI can optimize
• Boring 5% improvements that stack year after year

AI is leverage.
Assets are the base.

The winners aren’t choosing between tech or real assets.

They’re combining both.

Which “boring” businesses you think AI quietly supercharges.

I dropped a rent roll into ChatGPT and it flagged 3 issues the broker never mentioned.


Not because the broker was lying.

Because most people don’t actually read rent rolls.

They skim them.

Here’s what AI caught in under 60 seconds...

- A lease expiration cliff hiding behind “looks occupied.”
- Under market rents stacked in the same unit type (that’s pricing, not demand).
- A delinquency trend you only see when you stop staring at rows like a CPA.

None of this was obvious at first glance.

All of it mattered before an LOI...
...AI doesn’t replace underwriting.

It replaces lazy underwriting.

The winners won’t be the ones with the fanciest models.
 
They’ll be the ones who ask better questions, faster.

This isn’t “future tech.”
 
This is table stakes.

Bullish… or still doing this line by line in Excel like it’s 2014?

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62 miles, 1 Ultra Marathon, 2 lost toenails, 5 life lessons (My Story)




𝗗𝗲𝗰𝗲𝗺𝗯𝗲𝗿 𝟮𝟬𝟮𝟰:

My first ultra marathon...

26 hrs and 22 mins through the Thai Jungle Mountains. 

It kicked my ass, but I finished. 

Thank God. 

The course? 

1,000 times harder than I expected. 

Think: 

𝗧𝗵𝗲 𝗧𝗵𝗮𝗶 𝘃𝗲𝗿𝘀𝗶𝗼𝗻 𝗼𝗳 𝗠𝘁. 𝗘𝘃𝗲𝗿𝗲𝘀𝘁 (kidding but not kidding)

Picture this...

It’s 3 a.m. after 40 miles of running. 

You’re staring up at an 80% slope of mountain jungle and told, “Climb for the next 4 miles.” 

Sounds awful, right? It was. 

Bodies were dropping like flies - no joke. 

A train of 20 runners with headlamps crawled uphill. 

The pace? Slow AF. 

I'm talking the people who tracked me thought I gave up because my pace never updated on the tracking app slow. 

1 by 1, ppl stepped off the line, fading into the dark abyss of the jungle as the pack pushed on. 

By the time we reached the top, our group was half its size. 

My legs were screaming, and doubt flooded my mind. 

At .02 miles to the summit the steepest climb yet. I saw a young runner sitting lifelessly, staring into the jungle, broken. 

He’d given up, not knowing the next aid station was within reach. 

The mountain broke him. 

It nearly broke me too. 

Running 62 miles is insane. 

Running 62 miles in 80% humidity is even crazier. 

Running 62 miles in the Thai jungle with 14,000 feet of elevation? 

Mental. 

But I learned 5 unforgettable lessons: 


𝟭. 𝗚𝗿𝗶𝘁 > 𝗩𝗮𝗻𝗶𝘁𝘆

A 100k ultra isn’t a beauty contest. 

Forget makeup and Instagram poses. 

This is mud, sweat, blood, and grit. 

Nobody cares how you look out there. 

It’s you vs. you, mentally taxing and raw. 

𝟮. 𝗡𝘂𝘁𝗿𝗶𝘁𝗶𝗼𝗻 𝗜𝘀 𝗘𝘃𝗲𝗿𝘆𝘁𝗵𝗶𝗻𝗴

Ultra running = an eating competition with running in between. 

I downed: 

- 20 GU Gels 
- Lays chips 
- Diet Coke 
- Bananas 
- Ramen 
- Coconut water 
- Beef jerky (mistake). 

Anything to survive. 

At first, I felt over prepared. 

By mile 50, I realized I wasn’t. 

Being ready for the unexpected, cramps, fatigue, mental fog, is everything. 

𝟯. 𝗞𝗻𝗼𝘄 𝗬𝗼𝘂𝗿 𝗪𝗵𝘆

I met a Kiwi named Craig. 

He was 50, in a midlife crisis, and running his second ultra to see what he was made of. 

He asked me my "why." 

Here’s what I told him: 

To honor my dad, who passed in 2023
To lead by example for my boys
To end 2024 strong

“Sounds like you’ve got a solid why,” Craig said 

He was right

Without it, I’d have quit when things got dark

4. Please Lie to Me

My buddy Jimmy, part of my pit crew, promised me “flats and downhill” after B7 aid station

He lied

There were no flats

The downhill? 

Worse on the knees than climbing

But his lie kept me moving

Sometimes, a little hope...

Even if it’s false is what you need to push through

Final Thoughts:

Would I do it again? Absolutely

Hard choices make life easier. Easy choices make life harder

I pushed my limits and left me with lessons for life

9,000 Followers On LinkedIn, But Did You Know This About Me... 
 
 
Allow me to reintroduce myself. 
 
I'm Matthew... 
 
𝗧𝗵𝗲 𝗚𝗼𝗼𝗱: 
 
- Played football for a year (but no touchdowns!) 
- Got my degree from Colorado State University 
- Running a 100k on December 7th 2024
- Co-founded a landscaping business 
- Own a portfolio of over 400 units 
- Proud dad of 2 awesome boys 
- Started lawn mowing biz at 12 
- Grew up in Denver, Colorado 
- Passionate about real estate 
- Traveled to 23 countries 
- Brother's lives in the UK 
- Run an online business 
- Finished 7 marathons
- Have 4 best friends
- Spirit animal is wolf 
- Acted for 8 years 
- Mom's in Mexico 
- Big Michigan fan 
- Live in Thailand 
- Coffee is life 
- 39 yrs old 
- Bitcoiner 
- Married
- Loyal
- Chill
- Golf
- Ski
- 💪
 
 
And...
 

𝗧𝗵𝗲 𝗕𝗮𝗱: 

- I'm loud
- 💙 sugar
- Judge ppl
- Self Sabotage
- Held onto spite
- Lose small things
- Got arrested once
- Rocking a dad bod
- Have a kidney stone
- College GPA was 2.2
- Can get irritated easily
- Got scammed for $500
- My dad passed in 2023
- Worry about my grey hairs
- Acting didn't work out for me
- Struggled with debt in my 20s
- Sometimes I take on too much
- Tried and failed with HerbaLife
- Expat life feels lonely sometimes
- Feel I should be further in my career
- Didn't succeed in door-to-door sales
- Spent 2 years at N Colorado University
- My vid editing business didn't work out
- Started and stopped social media 17 times
- Struggle with thinking there's never enough
- Parents split for over 20 years (never divorced)
 
Do I have regrets? 
 
Nope. 
 
Everything in my life has brought me to where I am today and made me who I am. 
 
If you're reading this, know that I'm grateful for you and your support. 
 
Having ride or die friends family, and followers means the world. 
 
Let's keep spreading abundance in 2024 and succeed together. 
 
P.S. Where and how did we meet? Let me know in the comments.

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Matthew Baltzell 🌴

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