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.

Diamond Sharp Capital

Diamond Sharp Capital is a Veteran owned Commercial Real Estate firm with a mission to Impact Communities, Foster wealth generation and Transform lives through strategic and responsible investments.

Managing Partner / Owner

Wild Mountain Capital

At Wild Mountain Capital we change lives. We change people’s lives by transforming the most neglected and distressed "affordable housing" into healthy, well-governed communities that are affordable, safe, and a place people are happy to call home. We firmly believe that opportunity lies where responsibility has been abdicated either by property owners or by investment capital. To us, this is a health initiative that operates in a capitalistic paradigm.

Director of Investor Relations

United States Air Force

First Sergeant

Allegiant Giving

I am transitioning from the military and utilizing Allegiant Giving’s Skillbridge Program to assist me in this endeavor.

Digital Marketing Student

As a retired U.S. Air Force First Sergeant and Aircraft Maintenance Technician, I spent 20 years leading, mentoring, and managing operations in high-pressure environments. From maintaining mission-critical aircraft to guiding the welfare and performance of over 1,000 enlisted and civilian personnel, I developed deep expertise in leadership, strategic planning, and operational efficiency.

While still in uniform, I began investing in residential real estate, which sparked a long-term passion for entrepreneurship and private investing. After transitioning from active duty, I completed multiple commercial real estate and private equity education programs and pivoted into business and real estate acquisitions full time.

In my early work within private real estate investment firms, I led investor relations, managed capital contributions, and supported acquisitions and asset management. That experience deepened my understanding of syndications, capital strategy, and investor communications—skills I continue to apply today.

Now, as co-founder of Diamond Sharp Capital, I focus on acquiring and operating small businesses and value-add commercial properties using private equity and SBA-backed strategies. My goal is to deliver strong, risk-adjusted returns for investors while building long-term, community-driven value.

I’m committed to building lasting relationships, creating transparent investment opportunities, and executing with the discipline and mission-focus that defined my military career.

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