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.

Lester Chng

Cyber CEOs Brand Strategist. I build your brand as you build your business. | Senior Cybersecurity Advisor | Author | Naval Officer | CISSP | 🇨🇦🇸🇬 |

You head a leading cybersecurity firm.
But your online presence doesn't reflect it.

In fact, being invisible is damaging. 

You understand the power of thought leadership.
You know LinkedIn shapes deal flow and adds credibility in the industry.
You just don’t have the cycles (or the copy) to share your expertise and experience.

You have stories worth telling.

The insights from being in the trenches.
The deep conversations with your ace teams.
The hard discussions with your clients. 

Don’t let this wisdom go to waste.

That’s where I come in.

--------------------------------------------------------------------------------------------

How we work together.

Profile & Positioning
=> Rebuild your LinkedIn profile so visitors see industry authority, not “another vendor.”

Content engine
=> Ghostwritten posts that leverage your insights and expertise into engaging LinkedIn posts. 

Outreach campaign
=> Targeted DM campaigns and audience-building strategies that build your authority and land you on podcasts and conference stages.

--------------------------------------------------------------------------------------------

You focus on growing your firm and protecting your clients.
And we will ensure the industry, clients, prospects, and investors can’t ignore it.

Let’s build the personal brand that commands the cybersecurity conversation and drives business.


Worked with global client portfolio 
- MSPs
- MSSPs
- Agentic AI SOC
- AI-powered GRC 
- Operational Resilience 

Senior Advisor, Financial Crimes Unit Exercises. BMO Fusion Centre

Execution of Financial Crimes Unit Exercise and Drill Program
• Design and execution of exercises and drills to operationalize the Financial Crimes Unit Fusion Centre
• Scenario creation and exercise execution for Information Security, Enterprise Fraud Management, Physical Security, and Global Crisis and Continuity Management teams 
• Providing effective challenge of incident response readiness through exercise observation
• Execution of enterprise-wide Purple Team Exercise


Cybersecurity Exercises: Purple Team, Ransomware, DDoS, Malware, Data Corruption, Data Breach, 3rd Party Incidents
Fraud Exercises: ATOs, Attack on Payment systems, Business Email Compromise, PII Breach
Physical Security Exercise: Active Assailant, Civil Unrest, Bomb Threats
Crisis Exercises: Disaster Recovery, Business Continuity, Operational Resilience, Fire Incidents, Natural Disasters, Utilities Disruption

Welcome to yr cyber flight simulator. 

I promise I won’t make u cry. 

The Cyber Range has been a faithful workhorse of Rogers Cybersecure Catalyst, Toronto Metropolitan University. 

Incident response professionals, IT teams, municipal leaders, law enforcement officers, veterans, and foreign partners have gone through their paces at the range. 

Has yr team seen what a cyber incident looks like?

Have they been in the hot seat, trying to make sense of what’s happening and needing to coordinate and prioritise actions?

Have they been given the rigor of training to sharpen their instinct, rehearsal their articulation, and coordinate competitions priorities?

This is your cyber flight simulator. 

Step in and see what happens when the rubber hits the road. 

Or are you going to take the risk and wait for a real incident to find out?

Good luck. 
Godspeed. 


P.S 
Please follow Rogers Cybersecure Catalyst, Toronto Metropolitan University. 

We have been delivering exciting programs to individuals and organizations for years and have shaped Canadian’s Cyber Ecosystem. 

It’s going to be an eventful year. 

Follow + try to keep up w the Catalyst.

No alternative text description for this image

I once received AAR feedback from an executive that changed how I view these "mundane" reports.

After-action reports are very important to the success of an exercise program. Without it, there is no chance of leadership buy-in, and soon the program will fizzle out.

These are typical uses/benefits of an AAR.

• capture lessons learned
• provide recap of proceedings
• serve as evidence for risk/auditors
• feeds into enterprise-wide action item register

On this occasion, I drafted the AAR for a fraud-related exercise. It involved many operational teams including executive involvement. The AAR was signed and sent.

One feedback from an executive stood out.

"It had alot of detail, but I don't know if it was a success".

That struck me. We just missed an opportunity.

An opportunity to highlight:
• the alignment with the overall security program
• the collaboration involved to run the exercise
• the advancement in teamwork 
• the reduction of risk

Include a clear story and highlight the win in your AAR.

Don't take these exercises and artefacts for granted.
Each event builds confidence, familiarity, and resilience.
Don't let it go unnoticed; give it its due credit.

P.S Have you seen AARs put to good use?

Most cyber CEOs think LinkedIn is about “posting more.”

It’s about posting with a positioning equation:
Authority + Trust + Leads

Don't start without a clear content strategy.

Here’s the simple way to build your content calendar.

𝗔𝘂𝘁𝗵𝗼𝗿𝗶𝘁𝘆
1. Build authority so you become the obvious expert.
Authority is when your audience says,
“This person knows the space.”

Teach one niche concept per post (one takeaway).

Share your lived experienced not conceptual ones.

Break down “why this fails” in real environments.

Add proof when possible:
Lessons, patterns, results, before/after.
Authority posts go deep in your niche.
More “results, insights, wisdom.” Less "frameworks"

𝗧𝗿𝘂𝘀𝘁
2. Build trust so people believe in what you stand for.
Trust is when your audience says,
“I’d take a meeting with them.”
It comes from clarity and consistency, not hype.

Show how you think, how you communicate risk, and how you make tradeoffs under constraints. Use stories, principles, and honest calls on what you will and won’t do. When people understand how you deal with situations, they start to trust your delivery.

𝗟𝗲𝗮𝗱𝘀
3. Generate leads without sounding salesy.

Direct: a clear CTA after you have earned it.

Indirect: a walkthrough of what it is like working w you.

Remove friction:
scope, timeline, roles involved, what success looks like.

Make it obvious you solve this specific problem for this specific buyer. Lead posts can be direct or indirect, and “walk-through” posts remove buying friction fast.

If you want a repeatable content calendar, stop brainstorming topics.

P.S Do you start writing without a plan?

Thanks Timothy Martens for prompt inspiration.

And Gerald Auger, Ph.D. + Mike Miller
for the reminder to include an image =)

How was your first full week at work?

This will happen if you don't intervene.

The Rule of the First 5 Days is a stock market indicator that states that if the market performs positively in the first 5 trading days of the year, there is a high probability that the markets will end the year positively.

Historical probabilities are between 69 - 84%.

Some of the reasons are:
Early Positioning
Investor Sentiment
Self-Fulfilling Prophecy


Bringing it back to how was your first week back at work?

Busy?
Stressed?
Juggling priorities?

Chances are if you don't make any changes, this will be how your year pans out.


If you had a great week, keep at it!

If not, time to review:
- the triggers
- the pain points
- the larger picture
- the longer term goals

Good luck for week 2!

P.S Dow has best 5-day start to year since 2006!

undefined undefined

bootcamp

Sign up here:
https://catalystcorporatetraining.classe365.com/form/view/AutoBootCamp?_gl=1*9rfqtg*_ga*MTQ4NTczNDM0MC4xNjk4MjQxODM1*_ga_YYXBQS6S5Q*MTcwNzgzMzEyNi4xODEuMS4xNzA3ODMzMTYwLjI2LjAuMA

Time is flying by. Jan is almost over. 

This is 1 thing I miss from 10 years ago. 


My lucious hair that would give me a chance at K-pop auditions. 

Just kidding. I stand no chance. 



What do u miss from 10 years ago?




Thanks sir Chris Chia for taking this pic and sending it again to me recently!

Leader, Coach, Facilitator

If your cyber exercise doesn't make you sweat,

why do you call it an exercise?

Too many teams are taking a stroll during tabletop exercises. They don't prepare in advance, they talk in circles, and frankly take it too lightly.

I have seen teams prepare extensively for exercises.

They relook their process and hold internal preparation meetings to validate if it still makes sense. They ask tough questions internally and the leaders confirm if their assumptions about alternatives, recovery times, capabilities, and priorities are still accurate.

The best teams go in well-prepared and respond confidently. This is not just for show. This is an opportunity where leadership teams have recognized the importance of readiness and set aside protected time to be intentional about preparation. 

This only happens if the exercise program is well-socialized.
When the experience and outputs are understood.
And the leadership is serious about training.

Otherwise, what's the point?
Check a box? It's 2026, do better.

Your next Cyber TTX will be miles better with this small tweak. 

Don’t rush the start of the exercise. 

I know you have been planning it for months. Your adrenaline is pumping and you assume the participants are chomping at the bit to begin. 

But don’t neglect the pre ex brief. 

Here’s why it matters. 

1. Not everyone is familiar w exercises

Some have never participated in one. 
Others can’t remember what it’s like. 
1 or 2 even have weird assumptions. 

2. Remind everyone of the Why

The stakeholders are not equally invested in the exercise or outcome. Half are wondering why they are there. 

3. A good start is important

Some exercises that start poorly can result in minutes of waffling, rabbit holes or just straight up disengagement. 

4. Questions forces a buy-in

Facilitate a short quiz or discussion. 
This makes participants feel involved and helps them warm up as well. 

5. Simple introductions helps

You will be surprised how often teams don’t know each other or what role they play in an incident. 
Take time to do a roundtable intro. 

6. Sponsor emphasis 

Allow the exercise sponsor to speak. 
This reiterates the investment, focus, and important of the exercise. 

7. Calms your nerves

Address concerns before an exercise can help mitigate against difficult scenarios such as wrong expectations and challenging stakeholders. 
There will also be disruption but touching on some issues early helps. 

The next time you plan yr exercise. 
Spend abit more time on the start. 
It will be worth it. 

P.S any other exercise faux pax?

What most Cyber CEOs post on LinkedIn 
 
- repost their company's post 
- post about the latest hack 
- random AI blog 
 
What should Cyber CEOs post on LinkedIn 
 
- customer success stories 
- lessons learned about your business 
- strong opinion about industry issues 
 
You are the leader. 
 
Lead by example. 
 
Here are more post ideas. 

Subject Matter Expertise
- insights
- pain-points
- transformation
- trends + opinion
- counter-trends
- mistakes you have seen others made

Trust
- client success stories
- decision-making dilemmas
- framework for decision-making 
- social proof
- results

Character
- guiding principles
- values
- client examples
- stories of resilience
- leadership

Authenticity
- challenges that excite you
- lessons learned
- challenges that you overcame
- best advice that you received

Majority of my bosses in Cybersecurity have been female.

Yet female only make up 21% of the cyber workforce.

I interviewed Sarah to get her insights on Women in Cyber.

Sarah is a certified coach, facilitator, and founder of the Human Skills Leadership Lab, a unique and customizable program that helps professionals develop the human skills (or ‘soft skills’) required for effective leadership in the modern workplace. 


𝗪𝗼𝗺𝗲𝗻 𝗶𝗻 𝗖𝘆𝗯𝗲𝗿 𝗟𝗲𝗮𝗱𝗲𝗿𝘀𝗵𝗶𝗽 𝗣𝗿𝗼𝗴𝗿𝗮𝗺

1. When you think about women leading in cybersecurity, what have you noticed most often in how they lead, communicate, or navigate their roles?

They’re brilliant and discerning. They carry a full plate - navigating complex decisions and significant risk - and still, they lead with calm authority, thoughtfulness and integrity. They think deeply about their teams, their organizations, their families, and the broader systems. They’re the kind of leaders the world needs more of.


2. As you look ahead to the Women in Cyber Leadership Program in Malaysia with the Catalyst, what aspects of the program are you most curious or energized about?
   
After 4 years collaborating with the Catalyst to support cyber leaders from across Canada, I’m incredibly excited to connect with cyber leaders from 7 countries across ASEAN. It will be thrilling to be part of the conversation as these women come together to learn from and with each other.

 

If you enjoyed this interview series, please follow Sarah Lang (MA, PCC, CPCC). She is a human skills expert, a Leadership in Communication Skills Coach, and has trained leaders from leading corporations and brands.

P.S. How are companies promoting diversity?

Soft Skills Expert • Certified Leadership & Public Speaking Coach & Facilitator • Program Design and Instruction @ U Toronto, KPMG, ESRI, Rogers • I help leaders transform confidence into connection and influence.

I trained Principle Warfare Officers. 

We assessed them on 3 attributes. 

The Principle Warfare Officer (PWO) was responsible for fighting the ship. 

This included the deployment of weapons, manoeuvres, and in many cases the control of multiple ships and aircraft to fulfil a mission. 

These are the 3 attributes. 

Knowledge 
- know the procedures 
- know the asset capabilities
- know the adversary’s capabilities 
- know the ever changing situation 

Command and control
- clarity of situation  
- clarity of instruction 
- clarity of orchestration

Creativity 
- demonstrates intuition 
- demonstrates flexibility 
- demonstrates adaptability 


In cybersecurity operations,

We assess
.
.
.
.
.

Hope you get my point. 

Happy training.

Most cyber CEOs aren’t afraid to post.
They’re afraid to be misunderstood.

And 19 other myths of writing on LinkedIn. 

 1. “I’ll get DMs from random people and waste time.”
 2. “If I post about a niche topic, it’ll limit my market.”
 3. “I should wait until my messaging is perfect.”
 4. “I’ll get fact-checked and embarrassed.”
 5. “I’ll be judged by peers in the industry.”
 6. “Clients will think I’m wasting time.”
 7. “I’m not a ‘social media' person.’”
 8. “I need a hot take every time.”
 9. “I’ll look like I’m bragging.”
10. “My team will cringe.”
11. “I need perfect writing.”
12. “People will think I’m selling.”
13. “I’ll attract trolls or get dragged.”
14. “I’ll upset a partner/vendor/client.”
15. “My competitors will copy my ideas.
16. “I’m not ‘big enough’ to have opinions.”
17. “If I post, I’m giving away the secret sauce.”
18. “Need to sound super technical to be credible.”
19. “If engagement is low, it means I’m bad at this.” 

P.S which is your fav? Mine is #8  🔥

I reviewed the LinkedIn headlines of 23 Cyber CEOs.

Not 1 mentioned these important aspects.

LinkedIn headlines are your first impression.
More precisely, the first 57 characters matter.

They are seen:
• on your profile
• during connection requests
• on the main feed via your posts
• in the comments with every response


I help [buyer] achieve [outcome] without [pain].

None of the CEOs mentioned buyer, outcome, or pain.

How would you write your headline?



[9]
CEO at [Company]
CEO at [Company]
CEO at [Company]
Founder/CEO at [Company]
Founder and CEO of [Company]
Founder and CEO at [Company]
Co-Founder & CEO at [Company]
Co-Founder & CEO at [Company]
CEO & Co-founder at [Company] - We are hiring!

[7]
CEO at [Company]| Autonomous SOC
CEO @ [Company]- Enterprise Hyper-Automation
Co-founder & CEO at [Company]| AI for Security Operations
Co-founder and CEO @ [Company] | Security Operations, at scale
Co-Founder/CEO at [Company]| Outpace attackers with agentic AI SOC Analysts
CEO @ [Company]| Executive | Entrepreneur | Revolutionizing the SOC with AI
Founder, CEO @ [Company] Autonomous SecOps & Investigation Platform with Hyperautomation.


[7]
Hiring misfits to solve security!
Tech Entrepreneur, investor and board member.
CEO at [Company] and Author of [Book] available now!
Building Your AI Knowledge Engine for Security Operations. Hiring!
Building great teams to execute on very difficult engineering problems
Tech Founder & Executive. Defender. Nation-state Hacker. Medal of Honor Recipient. Public speaker.
Empowering businesses: ChatGPT training, strategizing AI implementation, and offering tailored LLM and AI solutions for process automation.

AI tools are being used in yr org. 
Have your IR plans kept up?
Here are 4 changes to make. 

Implementing AI tools have left security team scrambling over the last couple of years to ensure it is securely deployed and monitored. 

Your incident response plans may have be neglected in the process. 

Consider these updates. 

1. Include AI related incidents 

- sensitive data exposure
- supply chain vulnerabilities 
- unauthorised model changes 

Don’t assume your plan is a catchall. 
AI asset owners don’t fully understand the security risks. 

2. Validate asset + contact list

- AI asset owners 
- data architects r crucial
- most of these folks r probably new

These AI gurus have been heads down focused on speed on implementation. They probably can’t spell cyber if u meet them for the first time on an incident call. 

3. AI specific containment

- understand the impacts 
- ask if traditional options will work

It’s going to get more complex as AI tools integrate across enterprise. It may soon become so entrenched that disabling it is a non option. 

4. Logs and investigation 

- review if current threshold is valid
- check on logs before/after go-live

You will learn to love “black boxes” and need to navigate round them. 


P.S what other areas to add?

2.

Incident response plans only play a small part in cyber resilience. 

“Do you have an IR plan?”

Is probably one of the most common question that consultants and experts use to gauge a company’s resilience. 

Many teams are happy to tick yes. 

But having a plan is merely the start. 

Here’s why:
- high turnover of staff
- fast pace of tech change
- lots of assumptions remain  
- plans get outdated due to new tech 
- teams don’t use the playbooks/plans
- primary teams hardly get trained
- secondary teams ignored 
- random cyber exercises 
- no training plan

There is barely any focus on training. 

7 men squads in the military get more training time and resources than multi-million dollar cyber defence teams protecting our financial ecosystem. 

Will having a plan alone save you?

And how long are you going to assumed your team is ready?

P.S the world is still a vulnerable place

Human skills training will unlock your career potential.

These are your advantages against AI... for now.

I interviewed Sarah to get her insights on human skills.

Sarah is a certified coach, facilitator, and founder of the Human Skills Leadership Lab, a unique and customizable program that helps professionals develop the human skills (or ‘soft skills’) required for effective leadership in the modern workplace. 


𝗛𝘂𝗺𝗮𝗻 𝗦𝗸𝗶𝗹𝗹𝘀 𝗧𝗿𝗮𝗶𝗻𝗶𝗻𝗴

1. What are some of the key human skills that will unlock an individual’s potential in the workplace?
   
First: self-awareness, because awareness always precedes change. From there, the skills of emotional intelligence, listening and clear communication. These will help you improve your relationships and increase your influence and impact.


2. Were there pivotal moments from your own experience or from those that you coached that reaffirm that Human Skills Training is a vital part of career development?

I’m reminded of this everyday, given how easy it is to outsource one’s thinking, ideas, and voice to AI. We’re constantly pitched the benefits of efficiency, when really it’s our unique essence as a human that makes us compelling. Human skills will always be vital to professional and personal development.  


If you enjoyed this interview series, please follow Sarah Lang (MA, PCC, CPCC). She is a human skills expert, a Leadership in Communication Skills Coach, and has trained leaders from leading corporations and brands.

P.S. Are you worried about AI impacting yr career?

5 LinkedIn posts that should be part of your pre-RSAC marketing plan. 

If your Head of Marketing is not bugging you to start posting on LinkedIn before RSAC, ask them why?

Even better if they tell u what to post. 

Here’s 5 posts that I will write. 

“Heading to RSAC next week. Here’s the one question I’m asking every CISO I meet.”

“One year ago, [Client Type] was struggling with [Specific Problem]. Here’s what changed.”

“Everyone’s talking about [Trending Topic] at RSA. Here’s what they’re missing.”

“We’re bringing [Specific Thing] to RSA. Here’s why we built it.”

“I have 8 meeting slots open during RSA. Here’s who I wld love to talk to.”

_____________

Here’s 3 reasons why you shld post. 


REASON 1: 
Conferences are chaotic. 

This gives you a chance to cut through the noise.  

REASON 2: 
Post-Conference follow-up success is built upon pre-conference interaction.  

Unless you are a magician and can engage random folks on the floor. 

REASON 3: 
Yr competitors are already doing so. 

Silence = Falling Behind

You don’t want to waste all that $$$$

———————

No time to write?
Overwhelmed by the preparation?
Rather spend time on client demos?

Let’s work together and take that off your plate.

LinkedIn posts can be complicated.  

I simplify it by 3-2-1 method. 

3 types of posts 
- authority 
- leads 
- trust

Cycle this through the week. 

2 content pillars
- cybersecurity exercises
- LinkedIn copywriting 

Alternate pillars per day. 

1 target audience per post

Focus on 1 reader. 


What’s your 3-2-1?
⬇️

People judge within 7 seconds of opening yr mouth.

That's why I still get nervous before every presentation.

I interviewed Sarah Lang to get her insights on public speaking and establishing leadership presence.

Sarah is a certified coach, facilitator, and founder of the Human Skills Leadership Lab, a unique and customizable program that helps professionals develop the human skills (or ‘soft skills’) required for effective leadership in the modern workplace. 


𝗔𝗰𝘁𝗶𝗼𝗻𝗮𝗯𝗹𝗲 𝘁𝗶𝗽𝘀 𝗳𝗼𝗿 𝗹𝗲𝗮𝗱𝗲𝗿𝘀𝗵𝗶𝗽 𝗽𝗿𝗲𝘀𝗲𝗻𝗰𝗲

1. How would you explain what leadership presence is for those looking to grow in their career?
   
Leadership presence is your ability to stay grounded and intentional in all moments - including when you’re under pressure. In a society driven by distraction and dopamine hits, leaders who embody this type of presence, steadiness and self-trust stand out.  


2. What are some ways to practice being more grounded and present?

• Spend time on analogue hobbies that anchor you to the physical world - art, books, gardening, cooking, etc.
• Practice mono-tasking on purpose.
• Try slowing down your communication - listening, speaking, pausing, saying less.
• Regulate your nervous system with breathwork, yoga or grounding activities.
• Carve out daily moments to pause and transition between meetings and events


3. Presenting to an audience is a real fear for many professionals. Do you have a couple of tips that you usually teach?
   
First, get crystal-clear on what you’re trying to say and why it matters to your audience. Then, practice your vocal and non-verbal delivery to make sure you sound like you care about what you’re saying! I also teach simple ways to work with nerves rather than fight them so speakers can stay connected to themselves and their audience.
 

If you enjoyed this interview series, please follow Sarah Lang (MA, PCC, CPCC). She is a human skills expert, a Leadership in Communication Skills Coach, and has trained leaders from leading corporations and brands.

P.S. What's the best advice u received on public speaking?

Most Cyber CEOs post randomly and wonder why LinkedIn isn't working.
They write when inspiration strikes.
They share whatever feels right in the moment.
They post about the latest breach one day, their product the next, then go silent for weeks.

The result? Confusion. Zero traction. Wasted effort.

Here's what you should be doing instead:
Plan your content around 3 post types.

1. Authority posts
This is where you demonstrate expertise.
Share insights from client engagements. Dive deep into problems you're solving. Break down complex security concepts.

Examples:
"5 issues all enterprises face with AI governance"
"How we helped Company X reduce risk by 40%"
"The biggest misconception about Zero Trust"

These posts establish you as the expert in your niche.

2. Trust posts
This is where you build relationships.
Share your founder journey. Talk about team culture. Reveal the challenges you've overcome.

Examples:
"Why we started this company in 2019"
"The toughest decision I made as CEO"
"What our clients don't see behind the scenes"

These posts show the human behind the solution.

3. Lead posts
This is where you attract prospects.
Address pain points directly. Show transformation. Make your solution crystal clear.

Examples:
"Overwhelmed with compliance requirements?"
"How we saved a client 2000 hours per year"
"Is your board asking about AI risks?"

These posts turn readers into conversations.

Now here's the system:

Mon: Authority post
Wed: Trust post
Fri: Lead post

Repeat this for 6 months minimum.
Map out topics under each category. 
Populate your calendar. 

Never start from a blank page again.

Most cyber CEOs will read this and do nothing.

They'll keep posting randomly.
They'll keep getting zero results.
Don't be most CEOs.

Plan your content. Execute consistently. 
P.S. What type of post do you struggle with most?

Worried about the removal of your role?
Don't be a deer in headlights.
Do this immediately.

2025/2026 is the new 2020.

The trigger is different.
Lockdown vs AI.
The outcome is becoming the same.

And we shouldn't really be surprised...
If you are, stop living under a rock.

What did you think would happen?

Just look around the wider workforce, companies, tasks, processes, meetings, discussions, emails.....

Bots will be much better at most of that.

Thanks Sherlock, so is that the end for the human worker?

Maybe.... but not yet.

So, until we start serving robotic overloads, let's prepare and control what we can.

These are 5 things I'll immediately do to mitigate job risk.

1. Get better at your work

Thanks, Captain Obvious.
You are welcome, but I made Major.

The people who are most worried are probably the ones with the most areas to improve...so if there was a time to buck up, its now.

Say yes more than no.
Spend that extra hour.
Put in that additional effort.
Put yr hand up for that project.
Capture your achievements.
Socialize the wins w teams.
Help other teams win.


2. Restart your network

Your Rolodex is creaky, I know, but it is time to revisit.

It will be awkward at the start, but keep at it.
Better now than when you "need" a job.

Pro Tip: Be genuinely interested in them

Your older connections are easier to rekindle than establishing new ones. 


3. Build your profile

Refresh and improve your LinkedIn profile + professional portfolio.

It's 2026, we go to your profile and website if we want to get a good sense of who you are.

How are you showing up?
• old dated profile pic
• high school quality about section
• boring as f experience description

Or are you invisible?
Makes sense if you are James Bond.


4. Grow your network

Do some research. 

Who are your peers?
Who is in your dream role?
Which are the interesting companies?

Some of the folks who reported to you may now be execs.

Don't wait till your need a network to build one.

The earlier you start the better.

What are you waiting for? The HR Call?



5. Think like an owner

This is the future of the worker.
Gone are the days of 40 year old career.
My mom celebrates 45 years at 1 company soon!

If you think like an owner, you stop waiting for permission.

You start taking action, owning the risks, and keep going.

What is one thing you think will change when there is this mindset shift from employee to "owner worker"?

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taplio

The Battle

Pascal Wagner

Lester Chng

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Pascal Wagner's LinkedIn Performance

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