Joined July 2011
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1 Aug 2025
Most entrepreneurs are playing a rigged game.
96% of businesses never reach $1M in revenue.
75% of VC-backed startups go completely to zero.
Yet we keep following the same playbook.
After buying 7 companies in 10 years, I discovered why: ⬇️
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Jun 12
The fastest way to romanticize buying a business?
Assuming you'll inherit the previous owner's lifestyle.
Every time I hear, "The owner barely works anymore," I wonder how long it took them to get there.
Because ease is usually earned.
Years of solving problems create shortcuts.
What feels effortless to someone who's been in the business for a decade can feel overwhelming to someone stepping in for the first time.
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Jun 12
The transition period matters more than the steady state.
You're learning the business while trying to improve it, make decisions, and potentially service acquisition debt at the same time.
That doesn't mean you should avoid buying businesses.
It means you should go in with realistic expectations.
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Jun 12
Ask yourself:
• How dependent is this business on specific people?
• What systems actually exist?
• Where are the operational blind spots?
Building a business that gives you freedom is absolutely possible.
Just remember: the version you see today is the result of years of refinement.
You're not buying the outcome.
You're buying the opportunity to create one of your own.
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Jun 8
What's an opportunity you still think about years later?
Not because you made the wrong decision.
But because it taught you something about how difficult it is to recognize extraordinary opportunities when they're still ordinary.
This week's #WealthStackWeekly is about conviction, uncertainty, and why some of the biggest investing lessons come from the deals you never make.
👀 Curious what opportunity changed the way you think about investing?
wealthstackweekly.com
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Jun 3
Most people think building wealth is about earning more and saving more.
But eventually, something changes.
There comes a point where your portfolio starts generating more income than your job ever could.
And that's when the old playbook stops working.
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Jun 3
The habits that build wealth are powerful:
• Save aggressively
• Spend below your means
• Avoid bad debt
• Invest consistently
But once capital starts doing the heavy lifting, the challenge shifts from accumulation to allocation.
Different game. Different risks.
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Jun 3
Many high earners keep optimizing for income long after they should be optimizing for protection, diversification, and capital allocation.
The saver’s toolkit is great for building wealth.
It’s not always enough to preserve and compound it.
The question isn't just "How do I make more?"
It's "How do I manage what I've already built?"
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Jun 2
The new 007 game sold 1.5M copies in its first 24 hours.
Everyone talked about the developer and distributor, but almost nobody talked about the publisher.
That caught our attention.
In business and investing, the key player is often the one behind the scenes, shaping incentives, structuring economics, and deciding on the distribution of value.
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May 27
The startup world made “raising money” look like the finish line.
But a lot of experienced operators eventually realize:
Capital is easy to celebrate…
Ownership is harder to get back.
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May 27
There’s a huge difference between building a company to maximize valuation vs building one to maximize control, cash flow, and long-term equity.
More founders are starting to ask:
“Am I building a business… or building an outcome for the fund?”
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May 25
The investor who helped Yale grow from $1B → $40B told institutions to invest heavily in private markets…
Then later told everyday investors to avoid alternatives and buy index funds instead.
Contradictory?
Not really.
We break down the 3 reasons why in this week’s #WealthStackWeekly
wealthstackweekly.com
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May 20
"You never really know a borrower during good markets."
The most underrated line in private credit.
The shift from $500B → $2.1T isn't about rates.
It's about which lenders show up when things get hard.
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May 20
Private credit isn't an "alternative asset" story.
It's an operator story.
Founders got tired of being lent to like institutions, and once they tasted speed and flexibility, they didn't go back.
That's the real $2.1T shift.
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May 20
$500B → $2.1T in a decade.
McKinsey says the U.S. private credit opportunity could exceed $30T.
The firms that win the next decade won't have the flashiest models.
They'll understand operators best.
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May 18
I structure private deals for a living…
…and I still had 6 figures sitting in cash for years.
Turns out I’m not alone.
Vanguard found that many investors leave rollover accounts sitting 100% in cash long-term.
The problem:
Cash feels safe, but can quietly become one of the most expensive forms of liquidity.
This week in Wealth Stack Weekly:
→ the liquidity spectrum
→ why more cash ≠ more safety
→ and how a 1% cash position can sometimes be safer than 7.5%
We break it all down in this week’s Wealth Stack Weekly.
wealthweekly.com
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May 14
The biggest edge in investing usually isn’t intelligence.
It’s information timing.
Some people exit before the panic ever reaches the headlines.
Not because they predicted the future perfectly…
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May 14
But because they were closer to the reality on the ground.
By the time retail investors feel “certain” that something is wrong, the repricing often has already happened.
Markets move on whispers long before they move on announcements.
Makes you wonder:
How much of investing is actually analysis… and how much is simply access?
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May 11
Since 2022, the stock market and the job market have been moving in opposite directions.
Translation:
Your portfolio may benefit from the same automation threatening jobs.
That’s why real diversification won't come solely from the stock market.
It’s now about building income streams that are non-correlated with public markets and your employer.
This week in #WealthStackWeekly :
→ How to think like an allocator
→ How to evaluate your balance sheet in 2 steps
→ Why private assets matter more than ever
Join free: wealthstackweekly.com
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May 7
I really thought taking my honeymoon to a conference was normal at the time 😅
I had just bought my first company and couldn’t shake the feeling that if I missed a few days of networking or trend spotting, I’d fall behind.
So while most people were relaxing, I was walking conference halls, talking shop with people twice my age.
That’s the thing about building a business:
it slowly trains you to believe every moment should be productive.
-You stop taking real vacations.
-You check emails during dinner.
-You convince yourself the business can’t function without you for 48 hours.
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May 7
And for a while, that mindset helps.
But eventually, you realize the business will always ask for more.
More time.
More energy.
More attention.
It never naturally says, “That’s enough for today.”
You have to decide that.
Now, looking back, I don’t regret working hard.
I just understand something I didn’t back then:
Some memories compound more than money does.
What’s a moment where work quietly took over more space than it should’ve?
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