I recently turned 39.

Here are 39 brutal truths I wish I knew at 20: 1. Choose your hard. If you don't choose your hard, hard will choose you.

2. Ask more questions. As Socrates said: “Smart people learn from everything and everyone. Average people learn from their experiences. Stupid people already have all the answers.”

The smartest youth are losing faith in traditional education.

And I don’t blame them.

Here’s why MBAs are rapidly declining in value:

(*and a breakdown of the “DOJO” model that’s replacing $100k+ degrees) When Stanford GSB students say things like this, you know we've hit rock bottom.

That's one of the top business schools in the world being criticized by its own students.

If elite institutions are failing, what does that say about the rest?

Wall Street has one rule:

Never start what you can buy.

Here’s everything you need to know about buying a biz in 2025 (full guide): While 90% of startups fail, 80% of acquisitions survive the first year.

88% of people worth $30M+ have done at lease one acquisition.

That means the best way to get rich isn’t to start a business like they love to tell us.

The best way to wealth with the highest degree of certainty is through acquisitions.

You don’t need an MBA or tons of money to start a business.

I recently had Chris Koerner on the pod and he showed me three regular 6-figure side hustles anyone can start THIS weekend.

Here they are (with real examples): Porch Decorations

Rich people want their houses to look amazing, but they're too busy (or lazy) to do it themselves.

That’s where this mom Chris found comes in:

- She buys wholesale pumpkins by the truckload
- Decorates porches
- Films it on her iPhone and uploads to Instagram

She charges $600-1,300 per porch and makes $1M+ a year from this side hustle.

Isn’t that wild?

I’m obsessed with laundromats.

I've made more money from dirty laundry than most finance bros make on Wall Street.

Here’s the playbook I always use to find profitable laundromats: Quick disclaimer…we’re going to skip a few steps today.

We’re jumping right into the part of the biz buying process where you’ve found a biz that you could buy…

Now we’re going to check if you SHOULD buy it.

Follow these 5 steps:

Meet Taylor Sheridan.

15 years ago, he was sleeping in a tent and got rejected by every production company.

Today, he owns a $500M empire and charges Paramount to film on his ranch.

Here’s his story (and what you can learn from it): Most people think you need money to make money.

Taylor Sheridan (and countless others) prove that’s false.

You need LEVERAGE to make money.

Here's the Leverage Ladder framework Taylor Sheridan used to build his wealth:

If you follow where rich people put their money, you’ll never go broke.

Here's the unsexy asset class private equity billionaires & millionaires are flocking to: For decades, PE meant massive funds buying massive companies:

• KKR buys RJR Nabisco for $25B
• Blackstone acquires Hilton for $26B
• Apollo takes Harrah's private for $27.8B

The formula was simple: Big money buys big companies, adds big debt, cuts costs.

I just heard an acquisition story that made my heart melt.

Meet Cody:

• 6-year veteran
• #2 at a production company in California
• Runs the show while his boss lives in Utah

Here’s how he went from employee to owner of a biz in 90 days: After 12 years of building someone else's empire, Cody landed on our content about ownership.

He’s been leading operations at a production company so he definitely has experience running a business.

So I don’t blame him when the idea of ownership struck a cord with him.

You want to get rich... build relationships with people in finance.

They understand the game of money.

7 acquisition terms you should know to speak their language: Free Cash Flow (FCF)

If you're going to be obsessed with any number in your biz, it should be this one.

It's the cash left over after you've paid all operating expenses and capital expenditures (building improvements, vehicle purchases, etc.)

= Operating Cash Flow − CapEx

This is the ONE strategy that’s made:

• Warren Buffett one of the greatest investors of all time
• Amazon a trillion-dollar company
• Zuckerberg a billionaire

Any person who doesn’t know this model is missing out.

Here’s how it works: To show you why this strategy works, I want us to look at the wealthiest people on earth.

Why? Because success leaves clues.

And if you copy what successful people do, chances are you’ll be more successful.

Here’s a breakdown of how each of them reached billionaire status:

I recently had the most eye-opening conversation with Amjad Masad, the CEO who took Replit from near-death to $100M ARR in 6 months.

7 takeaways from our chat on talent wars, vibe coding, and AI myths: AI Talent Wars Are Fracturing Startups

Google just paid $2.4B to lift Windsurf's team and left a shell company behind.

This isn't a normal acquisition...they wanted the people, not the business.

The downstream effect? Startup employees now wonder if their founders will abandon them for big payouts.

It's eroding trust on a systematic level in the venture ecosystem:

One of the most underrated things you can do:

Buy unwanted land.

I spent $22,607 on 1 acre of dirt and turned it into a glamping site.

Here’s how I did it (and why): Quick overview of the full step-by-step:

1. Figure out my business model
2. Find my operator
3. Find the land
4. Prep the land
5. Create the design for the land
6. Market the site
7. First guest booking

Let’s dive in…

The longer something has been successful, the more likely it is to continue being successful.

Here are 12 businesses with historically low failure rates (backed by data): 1. Discount & Thrift Stores

People don't stop buying during recessions - they just buy cheaper.

Discount retail was one of the only sectors that "crushed it" during 2008.

In 2009, small thrift stores averaged 31% sales growth.

While big retailers were laying everyone off, these little shops were printing money.

I’m 38.

Here are 17 lessons from 17 years in business I wish I knew at 21: Never Lose Money

There's a reason this is Warren Buffett's #1 rule.

It doesn’t matter if you make $10 or $10M. If you lose money faster than you can make it, you're screwed.

Everything else in business is secondary to not going broke.

How to stay poor:

1. Never take risk.
2. Take risks you don’t understand.

Here’s how to minimize your risk when buying your first business: There's no such thing as the right or wrong business.

There's only the business that's right or wrong for you.

The risk is often in buying something you know nothing about.

That's why I created the Contrarian Deal Clarity Framework to help first-time owners find their perfect biz.

Why you never get what you want...

• You don’t ask.
• You don’t make it a win-win.
• You don’t know when to walk away.

Here's how to avoid these negotiation mistakes (& get the deal you deserve): If you want to fail in negotiating and alway overpay… don’t read this.

Buyers with experience only negotiate on three variables that determine the value of a business.

Most sellers don't even understand these concepts, which gives you a massive advantage if you can educate them on how deals really work:

Only 6% of Americans own a business.

And of that, less than 1% ever hit $1,000,000 in revenue.

After investing in businesses for 15 years, here are three reasons why 99% of businesses never scale past 7-figures: 1. Organizational Challenges

There are a ton of sub-catagories here but today we’re going to unpack “Executive Vision.”

Most owners think their problems stem from poor strategy, when it’s typically poor execution.

You can have the best plan in the world, but if your team can’t understand it... you're not going anywhere.

One failure I wouldn’t trade for a success:

Losing $50,000 buying my first business.

Here are 10 lessons on deal-making that I learned the hard way (so you don’t have to): Don't Buy An Unprofitable Business

It's tempting, but just don't.

Buying a turnaround means you're buying someone else's problems - cash burn, broken systems, demoralized teams.

Even if you fix it, you'll spend 3x more time and money than if you bought something that already works.

Harsh truth on scaling businesses:

Your goal as CEO is to build a team that runs your entire company better than you.

5 other lessons I’ve learned the hard way from 15+ years of being an owner: Operating Systems Win

The difference between McDonald's and your local burger joint isn't the food.

It's that any 16-year-old can run McDonald's because of their systems.

If your business needs you to be the hero every day, you own a job, not a business.

No systems = Everything breaks when you aren’t there

Everyone thinks the paths to wealth are:

Building a startup. Going into finance. Investing in real estate. Inheriting it.

I think there's a better way...

Here’s what it is (and why I’m investing millions into it): For years, I've been yapping about "boring businesses" - laundromats, car washes, etc.

But one industry fascinated me more than any other: home services. Why?

Because after a bad storm, ChatGPT can't climb on your roof and fix it.

I just sat down with one of Shark Tank’s most successful investors…

He turned $40 into a $6 billion fashion empire with FUBU, multi NYT bestseller, emmy winner, and so much more.

Here are 7 lessons from Daymond John about building a business that every owner should hear: Being Broke Has Its Perks

Everyone loves to say ‘you need money to make money’ but that isn’t 100% true.

If you can't get a customer with $200, you won't get one with $2M either.

Being broke forces you to work out the kinks in your business ASAP.