Most accredited investors I work with want three things:
1️⃣ Lower tax drag
2️⃣ Less concentration risk (not everything tied to one business, career, or public markets)
3️⃣ More optionality later (so work becomes a choice, not an obligation)


The problem is:
→ There’s no written, realistic plan for turning active income into durable passive income
→ You’re seeing LP deals, but there’s no consistent filter for what belongs in your portfolio
→ And you don’t feel 100% confident wiring 50–250k into a private deal without a second set of eyes


Who I am
I’m Pascal Wagner.
→ I’ve personally invested over $3.3M across 20+ private equity deals since 2019 – in funds and syndications across private credit, self‑storage, oil & gas, multifamily, and strategies like development, value‑add, and lending.
→ I’ve built a portfolio that now pays multiple six figures a year in passive income for my family.
→ Before Grow Your Cashflow, I was a fund manager for Techstars, where I helped deploy over $150M into early‑stage tech companies.

I work with accredited investors from “I’ve never done a private deal” to 20–30+ LP deals who still don’t have a repeatable system.

The common thread is moving from “a lot of money and information but no clear plan” to “I know exactly what I own, why I own it, and what it should pay me.”


How I help
I do three things:
1️⃣ LP Starter Kit (free)
A short guide, first‑pass vetting checklist, and a curated sample of 506(c) deals I’m watching. It helps you start thinking more clearly about LP deals and how to evaluate them.

2️⃣ Deployment Gameplan Call (1:1)
A 45–60 minute working session where we clarify what you’re solving for, unpack your biggest investing challenges, review what you’ve already tried, and decide together whether it makes sense to work more closely.

3️⃣ Cashflow Academy (core program)
For investors who want a thinking partner and a clear process to:
→ Build or refine a plan for deploying capital over the next few years
→ Review real deals, operators, and structures before you wire money
→ Use frameworks, checklists, and live deal reviews to make better, faster decisions

I’m not a financial advisor and I’m not tied to any single operator or fund. My job is to help you make smarter decisions with the money you’ve already earned.


Where to start
If you’re an accredited investor and this resonates:
→ Step 1: Grab the free LP Starter Kit (link in Featured)
→ Step 2: If you already know you want to talk 1:1, book a Deployment Gameplan Call and we’ll walk through your situation together

Pascal Wagner

If you’re struggling to find great real estate deals right now, your approach matters.

Here’s what I changed to put a $160K deal under contract last week that should generate ~20% cash-on-cash this year.

For context, I operate a portfolio of 94 single-family units rented by the room in Atlanta—this is how I earn my living.

Early on, real estate felt easier.
I could buy clean, on-market homes, layer in a better operating model, and make thin deals pencil.

That stopped working.

Prices climbed.
On-market inventory got picked over.
Cash flow got squeezed.

So I changed one thing:

I stopped looking for “nice” properties and started looking for ignored ones.

The $160K deal wasn’t turnkey.
It needed a full gut renovation.
It had been listed, passed on, and effectively forgotten.

That wasn’t a bug—it was the feature.

Buying well below after-rehab value gives me room to:
→ Absorb execution risk
→ Rebuild the asset around my cash-flow model
→ Make the deal work even if things aren’t perfect

I’m no longer trying to force my strategy onto whatever the market offers.
I look for assets I can rebuild with intention—and buy them where most people see friction.

That’s usually here:

→ Stale listings
→ Delisted properties
→ Sellers who lost momentum and just want resolution

The real lesson isn’t the purchase price.

As markets get more efficient, returns move away from “finding cheap listings” and toward creativity in sourcing and operating the asset.

If you’re refreshing the MLS hoping for 2019 numbers, this market will feel brutal.

If you start asking, “Where are the assets everyone else already gave up on?”
that’s where the edge shows up.

I help accredited investors build predictable passive income with private deals | LP investor ($3.3M in 20+ deals) | Ex-VC @Techstars (Deployed $150M) | Get My Free Starter Kit👇

When I was 17, I told my dad I could beat him in the stock market.

I had no idea what I was doing… but I was sure I could do it better. 🤣

So I opened a virtual trading account, made a bunch of pretend‑money trades, and convinced myself I had an edge.

Then I put real money on the line.  

Very quickly, I learned I didn’t.

---

My first “real” investment was under my dad’s supervision.

I put money into Jamba Juice because I loved going there.  

That was my entire thesis:

- “I like the smoothies. My friends like the smoothies. This will go up.”

It didn’t.  

I lost around 20%.

Painful? Yes.  
Useful? Also yes.

It taught me:

- Liking a product is not the same thing as understanding the business  
- “I enjoy this” is not a thesis  
- You need a real reason to believe the investment will perform

So the next time, I forced myself to build a better thesis:

- Electric cars are the future  
- Most incumbents are slow  
- If one company executes, it could be huge

A few years later, I sold a real estate deal and put $50K into Tesla.  

My dad matched it with another $50K.

For a long time, nothing magical happened:

- The stock was flat for years  
- There were scary drawdowns  
- People called it a joke more than once

Then, almost all at once, the price tore up.  

Over about 10 years, that $100K turned into roughly $1.5M.

The point isn’t “buy Tesla.”  

The point is what that whole journey burned into my brain:

1️⃣ You need a thesis before you invest  
2️⃣ You need enough conviction to sit through the boring and scary parts  
3️⃣ You need a repeatable way to do this, not one lucky shot

I don’t think wealthy investors need more “products.”  

I think they need:

- A clear thesis for each slice of their capital  
- A simple filter to decide which deals fit it  
- Enough confidence in their own process to sleep at night

If you don’t have that yet – or you want to see the kinds of private deals that can sit underneath a solid thesis (cash flow, tax, diversification) – that’s exactly why I built my free Passive Investing Starter Kit.

You’ll get:

- 25+ current private deals my family office is tracking  
- Weekly updates as new opportunities show up  
- A simple way to start matching vehicles to your own thesis

You can find the link to opt-in on my profile.

Sharing How I Built $250K+/Year Portfolio with 30+ Investments | Best Ever CRE Podcast Host (200K+ Monthly Listeners) | Ex-VC @Techstars, Deployed $150M in 3 Years | Join 1K+ Investors Using My Free Starter Kit👇

Multifamily didn’t “break.”

But a lot of investors learned—painfully—that who you invest with matters more than the deal itself.

In this episode of The Passive Income Playbook on the Best Ever CRE Show, I sit down with Michael Blank—Founder of Nighthawk Equity, multifamily operator with ~$300M AUM, ~1,850 units, and 7 deals gone full cycle—to unpack what actually happened in multifamily over the last cycle… and what’s changed.

Michael has been through multiple market environments, used both fixed and floating-rate debt, lived through the interest-rate-cap shock, and watched firsthand which operators survived—and which didn’t.

Rather than hype “the next opportunity,” this conversation focuses on how LPs should think about operator risk, leverage, underwriting discipline, and market timing heading into 2026 and beyond.

In this episode, we cover:
 ✅ What really caused multifamily distress (and why it wasn’t just “bad markets”)
 ✅ Why buying today looks fundamentally different than buying in 2021–2022
 ✅ How sophisticated investors think about risk-adjusted returns in this cycle
 ✅ The difference between fixed-rate vs floating-rate debt (and when each makes sense)
 ✅ What separates operators who survived the last 24 months from those who didn’t
 ✅ What LPs should ask for during diligence—and what it means if they don’t get it

If you’re a passive investor trying to understand how to avoid the wrong operator, evaluate risk beyond the pro forma, and invest with more confidence in the next phase of the cycle, this episode is for you.


Youtube Link in the comments 👇

I used to think $8K/month in retirement was “plenty.”

Then I went line‑by‑line through a real retiree’s books.

I’ve been helping an older family member with their finances.

I categorize every expense
I see every bank and credit card transaction
I close the books every month like a business

For the first time, I’m seeing what life actually costs when you’re not working:
→ Groceries creeping up
→ Rent or HOA inching higher
→ Healthcare and prescriptions getting more expensive
→ “Little” life stuff that never stops

Even “staying home and not doing much” is expensive.

We’ve structured things so there’s roughly $8,000/month coming in from a mix of cash‑flowing and equity investments.

On paper, that sounds like security.

In practice, a few things became very real:

1️⃣ There isn’t as much slack as you’d think

→ Inflation quietly hits everything:
→ Food, insurance, utilities, medical
→ Occasional travel to see family

It works, but there isn’t a big pile left over. You have to pay attention.

2️⃣ The shocks are what really hurt

It’s not just the recurring bills:
→ Dental work
→ Procedures insurance doesn’t fully cover
→ Home or car repairs

Those “surprise” months show how fragile a “fixed” income really is.

3️⃣ If it feels like this at ~$8K/month…

I keep thinking:
→ What does this feel like for people trying to live on $3K–$4K/month?
→ Or for people mostly relying on Social Security?

It drove home two things:
→ Inflation isn’t a headline. It’s a line item.
→ Most people underestimate the cost of their later years… until they’re in them.

Seeing this up close changed how I think about my own plan.

I don’t want to:
→ Build a big pile of assets and slowly sell them down
→ Hope markets are kind when I need to sell

I want to keep stacking boring, durable cash‑flowing assets and let them pay for life:

→ Use my working years to buy and build income‑producing assets
→ Prioritize deals that generate 10%+ in cashflow
→ Reinvest as much of that cash flow as I can, for as long as I can

You can have the same net worth on paper and a completely different feeling:

→ Not “I hope this nest egg lasts”
→ More “my assets send me a paycheck every month, and I’m still adding to the machine”

If you’re in your 40s, 50s, or 60s and want more of your later life funded by cash flow instead of slowly draining a nest egg, I put together a free Passive Investing Starter Kit.

When you join my email list from the link in my profile, you’ll get:

📌 25+ current cash‑flowing deals in real estate and other alternatives
📌 New opportunities added every Friday
📌 Simple frameworks to see which ones actually fit your situation

Best suited for accredited investors earning $200K+/year or with $1M+ net worth (excluding your primary residence).

A client of mine sold his e‑commerce business for over $30M.

Now he’s slowly redeploying that capital into “passive” real estate deals.

Like everyone, he sends me decks and asks the same question:
→ “Is this a good deal?”

That’s the wrong question.
The better question is:

→ “What risk am I being compensated for?”

Price is what you pay. Value is what you get. 

In private deals, the “value” is the specific risk you agree to eat in exchange for the projected return.

If you don’t know what that risk is, you’re not investing. You’re guessing.

Let me show you what I mean.

He recently sent me a medical office deal in California.

On the surface, it looked great: glossy deck, strong IRR, nice equity multiple, market stats, pretty photos.

The basics were:
→ Medical office property in California
→ Currently 16% occupied
→ Two signed leases that would take it to ~65% once the build‑outs are done
→ Those tenants don’t pay rent until their spaces are built out over the next ~2 years

So we start reading.

Buried in the numbers was the line that actually matters:

At 65% occupancy, the property barely hits a 1.0x debt service coverage ratio.

In plain English: at that level of income, it just covers the mortgage. No cushion.

That leads to the real diagnostic question I always ask:

“Why isn’t a bank doing this? Why isn’t the sponsor doing it with their own capital?”

At 65% occupancy, no bank will fund this loan.

So what’s actually happening here?

Investors are effectively acting as the “bank before the bank.”

The real bet in this deal is that:
→ The tenant improvements get done on time and on budget
→ The signed tenants actually move in and pay
→ The sponsor can lease another 1–2 suites, taking occupancy from ~65% to ~85%
→ At that point, the property qualifies for long‑term bank debt and a cash‑out refi to pay investors back

That’s the risk you’re being compensated for: lease‑up and execution risk on the path from 16% to a stable, financeable building.

If that doesn’t happen, the refinance doesn’t happen.

And all those “target returns” were just numbers in a PDF.

So next time you’re looking at a deal, don’t stop at “is this good?”

Ask yourself:
→ What has to go right for these returns to be real?
→ Why isn’t cheaper capital doing this instead of me?
→ Exactly what risk am I getting paid to hold here?

If you can’t answer that in one sentence, you’re not ready to wire.

Because in private deals, you don’t just earn returns.

You get paid to hold a specific risk other people don’t want.

Make sure you know exactly which one you’re signing up for.

The older I get, the less I care about “maximum return” and the more I care about “sleeping at night.”

When I first started investing, I obsessed over the upside:

→ “What IRR am I getting?”
→ “What cap rate am I buying at?”
→ “What’s the exit price?”

All important. But incomplete.
As you get more reps, the question quietly shifts from:

“How much can I make?”
to
“What risk am I actually taking, and am I being properly paid for it?”

Right now, the risk‑free rate is ~4%.

So every private deal has to clear a brutally simple hurdle:

Is this extra complexity, illiquidity, and brain damage worth more than 4% in Treasuries?

Take ground‑up development:
→ Timelines slip
→ Construction runs over (sometimes by a lot)
→ Lease‑up can drag
→ The market can change while you’re building

You’re stacking entitlement risk, construction risk, cost‑overrun risk, lease‑up risk, exit risk.

So yes, you should see 20–30% IRR on these if everything goes right.

You’re taking startup‑style risk in a hard‑asset wrapper.

Now compare that to a partially vacant medical office deal I looked at:
→ 15% occupied today
→ Leases signed to take it to 65%, but tenants don’t pay a dollar until build‑outs are done and they move in
→ You’re taking build‑out and lease‑up risk, plus the bet the operator can secure the last few tenants

That deal was offering ~15% returns.

On paper, both live in the “nice IRR” bucket.
In reality, the risk stacks couldn’t be more different.

The point isn’t “this deal good, that deal bad.”

The point is: if the return is higher, something in the risk stack is louder.

Your job as an investor is to answer two questions every time you look at a deck:
1️⃣ Exactly which risks am I taking here?
2️⃣ Given this operator and structure, do I honestly believe those risks are low?

If you can’t answer those clearly, the IRR is just a guess with good graphic design.

Want to invest but can’t seem to pull the trigger.

This could be the reason why:

You’re not clear about why you’re investing.

Most would-be LPs I talk to feel this exact tension:

→ You’re exposed to a lot of deals online
→ You hear about tax benefits and passive income
→ You feel like you should be doing something

But when it’s time to act?

You freeze.

Not because you’re scared.

But because you’re not clear why you’re investing.

So instead of committing capital, you:

 • Watch deals come and go

 • Second-guess every opportunity

 • Feel like you’re “close,” but never quite ready

If you want to escape this cycle, here’s the first step:

→ Decide what problem you’re actually trying to solve by investing.

Most passive investments solve for one of three things:

 1). Passive income to replace or supplement active income

 2). Reducing taxable income

 3). Diversifying away from public markets

Most people say they want all three.

That’s why they stay stuck.

Choose ONE and you’ll escape analysis paralysis and finally move toward making that first investment.

If I could go back and give myself one piece of advice after buying $4M+ of single-family homes, it would be this:

Talk to way more people than you think you need to.

I’ve spent the last decade building a single-family home portfolio that I rent by the room.

Today, I have relationships I trust.

→ Lenders who actually close
→ GCs who pick up the phone
→ Agents and operators whose judgment I rely on
→ People I can call when something needs to get done

But none of that existed early on.

If I were starting over, I’d tell myself to do this sooner:

→ Talk to 30 lenders
→ Talk to 30 general contractors
→ Talk to 30 real estate agents
→ Talk to 30 wholesalers

Not because you’ll work with all of them.

But because the value is in the numbers.

A real example:

In 2022, I did a cash-out refinance on my co-living portfolio.
→ I had 33 lender conversations
→ ~15 said they couldn’t do the deal
→ ~8 said they could… until diligence killed it
→ The remaining handful all offered different terms

Some differences mattered a lot:

→ 30-year amortization vs 15-year
→ Prepayment penalties vs none
→ Lower rates with more strings attached
→ Flexibility vs certainty

That’s where leverage actually comes from.

Not from being “good at negotiating.”
But from seeing all the levers you can pull.

Maybe I’m fine with a 5-year prepayment penalty because I plan to hold long-term.
Maybe I trade flexibility for a lower rate.
Maybe I prioritize certainty of execution over pricing.

Those decisions only exist if you’ve seen enough deals to compare.

The spreadsheet is the real asset.

I can juice returns today not because I’m smarter—but because I’ve built a deep bench of people I can call on to make a specific deal work.

If you’re early in your investing journey, don’t optimize for speed.

Optimize for exposure.

Talk to more people.
Collect more data.
Build your bench before you need it.

That’s how real leverage is created.

If you’re nervous about putting more money into the stock market right now…

You’re not crazy.

Equities feel expensive.

Treasuries finally pay something.

Commercial real estate just went through a real reckoning – capital calls, paused distributions, ugly write-downs.

A lot of accredited investors I talk to (net worth: $1M+) are stuck in the same place:
→ “I don’t want to sit in cash…
→ but I also don’t want to blindly buy more of the same stuff at these levels.”

So here’s how I’m thinking about this part of the cycle — and a few distinct buckets worth understanding if you want to do more than just “hold and hope.”

1️⃣ Short‑term Treasuries (parking lot + defense)

Right now, T‑bills and short‑duration Treasuries actually pay something.

- Pros: super liquid, very low credit risk, simple  
- Cons: you’re not getting rich; you’re buying time and optionality

This is where I’m comfortable holding “dry powder” instead of letting idle cash rot in a bank account.

2️⃣ Monetary hedges (gold, Bitcoin, alternatives)

This bucket isn’t about yield.

It’s about protecting purchasing power.

Assets like gold and Bitcoin play a different role:

They’re a hedge against long-term U.S. monetary policy

They’re not tied to earnings growth, rent growth, or GDP

They exist outside the traditional financial system

Pros: diversification from dollar-denominated assets, asymmetric upside in certain regimes

Cons: volatile, no cash flow, psychologically hard to hold if you size it wrong

I don’t look at this bucket as something that “makes me money.”

I look at it as something that keeps the rest of my portfolio honest if the dollar keeps getting debased.

3️⃣ Real estate (cash flow + tax advantages + real demand)

This is where I’m still structurally bullish.

Yes — real estate values are high in many markets.

Yes — cap rates expanded and a lot of people got hurt.

But a few things still hold true:
Real estate uniquely combines cash flow + tax advantages

Depreciation and expense treatment still matter a lot for high earners

Housing demand didn’t disappear — affordability did

Personally, co-living has continued to work well for me.

Rents may have come down from the absolute peak, but the demand from people who don’t qualify for a one-bedroom apartment hasn’t gone anywhere.

If anything, it’s gotten stronger.

I like being in businesses that:
Serve real affordability gaps

Solve an actual housing problem

Produce income while letting me keep more of what I earn

These are not “throw-a-dart” categories.

But when you underwrite them well — structure, debt, operators, and downside protection — they can deliver cash flow and meaningful tax efficiency at the same time.

Most high earners only ever see one version of real estate debt:

Bank loans on finished properties.

The problem is—that’s not where the highest-paid lending actually happens.

---

Most high earners only ever see one part of the game:

- You buy a house or a stabilized rental  
- The bank underwrites your income and the asset  
- You get a 30‑year or 10‑year loan  
- Done

So when you hear “bridge loan,” it sounds exotic.

In reality, it’s just the debt that funds everything banks don’t like to touch:

- First few projects for a newer operator  
- Heavy rehab  
- Lease‑up risk  
- Hairy situations that need to be fixed before a bank will show up

Fairbridge Asset Management has a simple way of mapping this out.

Roughly, the real estate life cycle looks like this:

- Land  
- Pre‑development  
- Acquisition  
- Construction / rehab  
- Stabilized and boring

Now imagine two lines across that:

- Banks: “No… no… maybe… maybe… YES.”  
- Private lenders: “Yes… yes… yes… yes… yes.”

That’s a bridge loan:

- Short‑term, usually 6–36 months  
- Secured by the property  
- Designed to “bridge” from:
  - Land → pre‑dev  
  - Acquisition → rehab / lease‑up  
  - Construction → stabilized  
  - Distressed → fixed and refinanced

From the *borrower’s* side, a bridge loan is:

- More expensive than bank debt  
- Much faster and more flexible  
- Often the only option for getting a real project off the ground

From the *investor’s* side (as an LP in private credit funds), those same bridge loans are:

- Senior in the capital stack (you get paid before equity)  
- Backed by hard collateral  
- Shorter‑duration than equity  
- Typically paying higher yields (often 9–12%+ in many funds) to compensate for taking that earlier‑stage risk

You’re essentially getting paid to be the lender in the “messy middle” of the life cycle…

…funding the part the bank will only touch **after** the hard work is done.

That one mental picture changed how I look at private credit:

- Banks get paid to lend on the finished product  
- Private lenders get paid more to finance the transition from “idea / broken” to “bankable”  
- As an LP, I can choose *which part* of that spectrum my capital funds

If you’re going to invest in private credit or bridge debt, the key questions aren’t just:

- “What’s the yield?”

They’re:

- “Which stage of the life cycle is this funding?”  
- “What has to be true for a bank or long‑term lender to take me out?”  
- “What happens if that take‑out is delayed?”

Most people never ask those. They just see a percentage and hope.

If you’re an accredited investor and you want more exposure to that 9–12%+ asset‑backed “messy middle” – without having to underwrite every sponsor from scratch – my free Passive Investing Starter Kit walks through 25+ current private deals (including bridge‑lending funds) and the exact filters I use to evaluate them.

I’ll drop the link in the comments.

​​The bigger your portfolio gets, the less it should be about excitement…  
and the more it should be about **job descriptions**.

Every dollar needs a job.  
Not every dollar needs to be exotic.

---

I was reminded of this reading a post from Brian Beers. 

Brian built an amazing business through franchises. He’s seen all the “alternative” stuff:

- Oil & gas  
- Private deals  
- Exotic structures

He chased a lot of it for a while.

Now?

He’s back to dollar‑cost averaging into index funds.

Simple. Predictable. Scalable.

Not because he’s lazy.  
Because his **business** is already his high‑risk, high‑reward engine.

The market doesn’t need to be.

---

It got me thinking about *where* your money comes from.

If you’re a business owner:

- You already have a machine you control  
- You can reinvest in new locations, staff, marketing, systems  
- You often get built‑in depreciation and tax advantages

For a lot of owners, the smartest play is:

- More cash flow → reinvest into the thing you’re world‑class at → more cash flow → more depreciation → more tax savings → repeat

In that situation, exotic outside investments may not make a ton of sense…  
unless you’re deliberately diversifying away from your own business.

But if you’re a high‑income W‑2 executive or professional, it’s different:

- You can’t “open another you”  
- You don’t control the P&L  
- Your income is capped by time, health, and comp bands

You don’t have the same “reinvest into myself” flywheel.  
You may need other assets to play the roles a business would:

- Private real estate or credit funds for **cash flow**  
- Certain alternatives for **tax efficiency**  
- Index exposure for **broad growth**

Same goal (grow and protect wealth).  
Very different tools.

---

Personally, I’m diversified on purpose:

- Real estate I own and operate  
- Private credit / income funds  
- Stocks and index funds  
- Select crypto / Bitcoin‑adjacent bets  
- Oil & gas for specific tax goals  

But every line item exists for a reason:

- This sleeve is for monthly cash flow  
- That sleeve is for long‑term growth  
- This one is for tax advantages  
- That one is for asymmetric upside I can afford to lose

No one‑size‑fits‑all answer.  
But there *is* a one‑size question:

- “What job do I want this next dollar to do?”

If your honest answer is “I just want it to be exciting,” that’s fine…  
as long as it’s the right slice of your capital.

Curious how you’re thinking about this right now:

- Are you still mostly chasing growth?  
- Or are you shifting more toward preservation and cash flow as your portfolio grows?

If you don’t talk about money openly, you’re keeping yourself small.

I was fortunate growing up that money wasn’t taboo in my household.

We talked about it plainly and often:
→ What returns are we getting?
→ What stocks do we own?
→ What real estate do we hold?
→ What’s the rate?
→ What’s the loan-to-value?
→ How much debt do we have?
→ Where is our cash sitting—and why?

That environment normalized learning about money instead of pretending to understand it.

There are a lot of factors that go into becoming financially successful.

But one of the biggest is the willingness to say:

“I don’t know enough about this. What do you know that I don’t?”

That conversation can happen with:
→ Your tax accountant 
→ Another real estate investor
→ A venture capitalist
→ A friend who’s simply one step ahead of you

It’s less about who you talk to—and more about being willing to ask.

A small example from this weekend:

I was comparing brokerage accounts and casually mentioned margin rates in conversation.

→ Fidelity: north of 12%
→ Robinhood: closer to 6%

Then I learned Robinhood was offering ~2.5% matching on transferred assets.

Same capital.

Lower borrowing cost.

Less risk.

Free upside.

Nothing changed except knowledge.

That’s how a lot of life works.

Not because you’re doing something wrong—
but because you don’t yet know what’s possible.

For better or worse, I’ve gone against the taboo and talk about money openly.

It’s uncomfortable—especially online.

You risk sounding ignorant.

You risk being judged.

But I’ve noticed something:

The people worth betting on are the ones willing to look a little stupid in public long enough to learn.

If you’re not where you want to be financially, the biggest unlock for me wasn’t a single deal or strategy.

It was talking openly about my situation—and listening to how others think.

Curiosity compounds faster than capital.

You open a deal deck that looks perfect — polished returns, confident operator, flawless pitch.

But something still feels off.

That hesitation isn’t fear — it’s intuition. And for most LPs, it’s the only line of defense they have… because nobody ever taught you how to actually vet a deal.

In this solo episode of The Passive Income Playbook on the Best Ever CRE Network, I walk through my real due-diligence checklist — the exact questions I use to vet private debt and credit funds before I invest.

Most investors stop at that hesitation because they don’t have a framework to go deeper.

After getting the opportunity to deploy over $150M at Techstars and personally investing $3.3M across two dozen private deals, I built a repeatable, institutional-grade process to separate marketing from merit before wiring a dollar.

In this episode, you’ll learn:
 ✅ The baseline: thesis → deal flow → filter before deep-dive
 ✅ 100+ questions across 6 sections (manager, fund, performance/structure, loan tape, investor terms, external checks)
 ✅ How to push for actual numbers (e.g., 2024 return—not “last 12 months”)
 ✅ The two leverage questions most IR teams dodge—and how to ask them
 ✅ Default rate, LTV, first vs. second position: what’s acceptable vs. a red flag
 ✅ Lockups, redemptions, tax forms, audited financials: the “investor experience” checks most LPs skip
 ✅ External diligence: litigation searches, background checks, and how to document your work

If you’ve ever stared at a deck thinking, “What am I missing?”—this episode reveals the questions that turn hesitation into conviction.

Youtube Link in the comments 👇

There’s a spectrum I see over and over again when it comes to private deals.

At one end are the *best deals* I ever come across.

The kind where the operator or founder can take the whole thing down themselves.

They put all their own money in.
They don’t need outside capital.
And if you’re lucky, you might even have to squeeze into the deal.

That’s a massive signal.

It means the person running the deal believes in it enough to concentrate their own capital and live with the outcome. The incentives are simple: if the deal works, they win. If it doesn’t, they feel it.

On the other end of the spectrum are deals where the operator puts little to none of their own money in.

Investors fund the deal.
The operator collects fees.
And most of the downside lives with other people.

I’m not saying those deals can’t work—but the incentives are very different. 

When someone is primarily making money by doing deals, rather than owning them, volume starts to matter more than outcomes.

Most real-world deals sit somewhere in between.

As deals get larger, it’s not always realistic—or smart—for one person to fund 100% of the capital. 

For me, once deals move into the $1–10M range, putting all my net worth into a single asset doesn’t make sense, no matter how good the deal is.

So I’ll typically put 20–30% of the required capital in myself and raise the rest.

That’s still real exposure.
The deal still needs to work.
But the risk is sized appropriately.

And this is where nuance matters.

What’s “meaningful” skin in the game depends on the operator’s net worth, cash flow, and overall portfolio. A $250K check might be massive for one person and irrelevant for another.

But in general, I’ve found this to be true:

The more capital an operator willingly puts at risk, the more aligned the deal tends to be.

Not always.
Not perfectly.
But often enough that it’s one of the first things I look at.

Before the IRR.
Before the deck.
Before the story.

Once you start evaluating deals through that lens, it gets a lot easier to understand who’s really taking the risk—and who isn’t.

And that clarity alone can save you from a lot of bad investments.

“We did our due diligence.”

Probably the most overused and misunderstood phrase in private investing.

Almost everyone says they do due diligence.

But after coaching 30+ multimillionaire investors, I see the same mistake over and over:

What most people call due diligence
and what actual diligence looks like in practice
are two very different things.

Here’s what most LPs mean by “we did our diligence”:

→ Read the investment memo
→ Skim the pitch deck
→ Ask a few questions
→ Sleep on it
→ Wire

That’s not due diligence.
That’s familiarization.

You feel familiar with the deal. You feel familiar with the person.
So your brain labels that feeling “diligence.”

Here’s what real due diligence looks like for me.

When I buy a real estate asset for my single-family portfolio, I run everything through a written checklist.

Not a vibe check.
Not a gut feel.
A checklist.

Each item has a clear, binary answer:

→ Yes / No
→ Verified / Not verified
→ Documented / Missing

It’s a simple, repeatable process designed to:

→ Force discipline
→ Reduce blind spots
→ Make sure I’m following my own rules
→ And keep emotion out of the decision

I pull screenshots.
I collect documents.
I organize everything in one place.

Not because I’m paranoid, but because I want proof that I actually followed the buy box I’ve built and refined over time.

And the same principle applies whether you’re:

→ Buying a cash-flowing business
→ Investing in commercial real estate
→ Or evaluating early-stage tech (which I did during my time at Techstars)

The specifics of the checklist change.
The existence of a checklist does not.

For example, in a cash-flowing debt fund, my checklist forces answers to things like:

→ “What is your delinquency rate today?”
→ “What was your delinquency rate 12 months ago?
→ “How has your underwriting process changed over time? 

There’s no “trust me” box.
Only “show me.”

If you want to be good at private investing, you need a step-by-step due diligence checklist that you follow every single time.

Not one that lives in your head.
One that lives on paper.

Inside my Cashflow Academy program, I walk you through building your own version of this and I share a sample due diligence checklist specifically for evaluating different asset classes.

If you’re looking at private deals and want more structure around how to:

→ Spot hidden risks
→ Ask sharper questions
→ And avoid paying tuition in lost capital

Start with the LP Investing Starter Kit on my Linkedin profile.

Most losses in private investing don’t come from bad intentions.

They come from vague processes.

And in private markets, “vague” is just a polite word for unpriced risk.

Most LPs don’t struggle with due diligence because it’s hard.  

They struggle because it’s uncomfortable.

—

When I first started investing, “due diligence” meant:

- Read the deck  
- Skim the website  
- Assume someone smarter had already done the work  

That’s how a lot of investors operate.

Over time I realized something simple but awkward:

You’re allowed to ask real questions.  
And if you do it right, it *will* make things uncomfortable.

Because real due diligence looks more like:

- Hours of phone calls  
- Filling out checklists  
- Asking for documents that aren’t in the deck  
- Doing your own third‑party research  
- Being willing to walk away after doing all that work

I remember spending about three hours on calls with one fund:

- I worked through my checklist  
- I asked for performance data and underlying exposure  
- I did my own digging

Nothing “blew up.”  

But the longer I pushed, the fuzzier the answers got.  
Requests for basic info were delayed, dodged, or minimized.

So I walked.

Not because I had proof they were bad actors.  
Because they weren’t willing to be transparent at the level my capital requires.

Maybe the next fund wouldn’t fit either.  
Then I’d start over again.

That’s the job.

Here’s my simple rule:

- If a fund won’t provide basic information (loan tapes, underlying holdings, historical performance, reporting samples, audited or at least reviewed financials)… I move on.  
- Banks require that info, so it exists. If they won’t share it, they’re choosing not to.

There are too many deals out there to settle for “just trust us.”

Due diligence isn’t complicated.  

It’s asking clear questions, insisting on data, and being willing to make it a little uncomfortable.

If you’ve never lost a deal because you asked for too much information, you’re probably not doing real due diligence yet.

When you invest in a fund, the most dangerous number isn’t the IRR.

It’s the incentives and cash‑flow dynamics of the fund manager.

Most fund managers are asset‑rich and cash‑poor.

They don’t have a separate cash‑flowing business.
They don’t have a meaningful W‑2.
Their primary way of creating value is growing asset values over time, not producing steady cash.

→ Buy a $1M property
→ Put $1M into renovations
→ End up with a $3M asset

That’s a real $1M gain – but it usually takes years.

During that time, the operator is:

→ Funding capex
→ Upgrading systems and interiors
→ Re‑tenanting
→ Reinvesting nearly all cash back into the asset

There’s usually not much cash flow to live on.

So how do fund managers survive?

Fees.

Acquisition fees.
Asset management fees.
Refinance fees.
Property management fees.

Many commercial operators also own asset management and property management companies. 

Those businesses can’t live on one deal.

If a property generates $1M in gross rent and the management fee is 10%, that’s $100K in revenue.

That $100K has to cover:
→ Bookkeeping & tax
→ Software & CRM
→ Staff or VAs
→ A real property manager

So what happens?
They need volume.

More assets.
More deals.
More AUM.

That’s why you’ll often see managers putting only their earned fees into a deal. It’s not always because they don’t believe in the asset – it’s because they’re cash‑constrained and need liquidity to keep the machine running.

When a deal goes full cycle and capital is returned to investors, that fee stream disappears.

The management company loses that recurring revenue overnight.

That’s exactly what we saw over the last cycle in commercial real estate: as deals exited, newer managers had to keep doing deals just to sustain their teams. Some deals exist just to keep them alive.

That doesn’t make a fund manager “bad.”
But it does mean the incentives matter.

Now compare that with an operator who:

→ Has real cash flow from another business or career
→ Doesn’t rely on fees to pay the bills
→ Is primarily deploying their own capital into assets

They can afford to say “no” when a deal doesn’t clear a high bar.

They’re optimizing for:

→ Risk‑adjusted returns
→ Durability
→ Long‑term ownership

Not deal count.

The point isn’t to avoid funds.
It’s to understand what game the manager is actually playing.

Before you wire money, ask:

→ If you stopped doing new deals for 3 years, how would you pay yourself and your team?
→ What percentage of your personal net worth is in this strategy?
→ How much of your income comes from fees versus performance / ownership?

You don’t just underwrite the deal.

You underwrite how your manager eats.

If your stock portfolio looks “great” on paper but your gut feels uneasy…  

You’re not crazy.

This doesn’t feel like a strong, broad‑based economy to me.  
It feels like a fragile, top‑heavy one.

From where I sit, a huge share of the S&P’s strength is coming from a small group of AI + mega‑tech names.

Depending on what you look at:

- 5–10 companies are driving a disproportionate chunk of index returns  
- A lot of “old economy” businesses are flat or negative on real earnings  
- Under the surface, households are stretched: record‑high debt balances, rising auto delinquencies, and consumer credit stress in several buckets that’s uncomfortably close to ’08‑era levels

On the surface:

- Unemployment is low  
- Index is up  
- AI productivity stories are everywhere  

Underneath:

- Consumers are carrying more debt  
- Financing costs are higher  
- Many businesses are feeling margin pressure

In a setup like that, it doesn’t take much:

- A couple big earnings misses from the wrong names  
- A sentiment shift in AI  
- Or a credit event that hits already‑stretched households

…for the mood to flip fast.

I’m not trying to play armchair Fed here.  
I’m just looking at this as someone who has to allocate real money and live with the consequences.

Right now, that’s pushed me to tilt more toward:

1. Short‑term Treasuries
   - Get paid while I wait  
   - Keep optionality if/when better entry points show up  

2. Boring, asset‑backed cash‑flow
   - Private credit and real‑asset deals I can actually underwrite  
   - 8–15% type yields with real collateral instead of hoping multiple expansion bails me out  

3. Gold
   - A balance-sheet asset, not an income one
   - To hedge rising deficits and weakening fiat credibility

In other words:

> I’m not all‑in, and I’m not all‑out.  
> I’m just assuming this is a fragile, concentrated environment,  
> not a “this goes up forever” one.

I don’t know exactly when anything breaks.  
I do know I’d rather be slightly early on defense than very late.

That’s how I’m thinking about my portfolio right now.

How are you positioning your portfolio in a market that looks strong on the surface, but this top‑heavy underneath?

I think one of the most underappreciated challenges in private investing is this:

Every deal “speaks a different language.”

Some sponsors share a 60‑page deck, full data room, and historical financials.

Others send a 3‑page PDF.

Risk is framed differently.
Track record is framed differently.
Tax treatment is framed differently.

If you don’t have a standard way of reading deals, you end up comparing story to story instead of deal to deal. 

That’s how smart people end up taking asymmetric risk without realizing it.

To do this well, you have to be good at reading between the lines:
→ What’s missing from the materials
→ How assumptions compare to actuals
→ How this deal stacks up against comparable opportunities
→ Whether the structure really matches your goals (cash flow, growth, tax, liquidity)

The pros don’t just “review” deals. They normalize them.

Same metrics. 
Same questions. 
Same red‑flag checklist. 
Every time.

That’s what turns a random stream of pitch decks into a coherent portfolio strategy instead of a collection of one‑off bets.

If you’re a busy accredited investor and you feel like every deal is a new puzzle with new rules, you’re not crazy. That’s the game.

Your edge is having a repeatable way to read the game.

Private investments feel risky for one reason:

They don't offer public-market transparency.

When you invest in public markets, you’re trained to expect:

  • Standardized disclosures
  • Comparable metrics
  • Endless third-party analysis

So when you start looking at private deals and that structure disappears, it’s unsettling.

Suddenly:

  • There isn’t much public information
  • Every deal looks different
  • You don’t know what’s normal or what’s a red flag

That doesn’t mean private investments are inherently riskier.

But they are less standardized.

And when standardization disappears, confidence can’t come from “more data.”

It has to come from better filters.

So instead of asking:

“Where’s the public information?”

Better questions are:

  • What should a credible operator be willing to share?

  • What information can’t be standardized in private deals?

  • What patterns show up across well-run investments?

Once you know what must be there, the lack of public information stops feeling like a problem.

It just becomes part of how private markets work.

P.S. Join 1,000+ investors who’ve stopped guessing and started vetting private deals the right way. 

Grab my Passive Investing Starter Kit  today. 

Link in bio.

Greystone

Commercial Real Estate Production Analyst

Commercial Real Estate Intern

Matt is a Real Estate Financial Analyst for Greystone Servicing Company. Working on the Chicago Production Team, Matt analyzes, underwrites, and completes due diligence for multifamily commercial real estate loan originations. In his role, Matt makes exceptional use of his skills in financial modeling, cash flow analysis, market research, risk evaluation, and more. He has proficiencies in applications such as Excel, CoStar, and Moody's Analytics. Matt has over a year and a half of industry experience between his current role as an Analyst and his previous role as an Intern at Greystone.

Matt is a 2023 graduate of Hope College in Holland, Michigan. He graduated with honors as a double major in Business Finance and Economics. Matt was a student-athlete on the men’s tennis team, serving as a three-year team captain and earning multiple all-conference athletic and academic awards.

In addition to real estate, Matt is passionate about personal finance, economics, and investments. He is always eager to learn new skills, complete courses or certifications, and engage with others to broaden his knowledge of the overarching financial industry.

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