I own a portfolio of Main St companies. NYT best-selling author | Invest: @CTVentureCap, https://t.co/GeVvWuYSgV | Build: @_CTCommunity @bizscout_ @resibrands
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Aug 2 • 13 tweets • 4 min read
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.
Jul 26 • 12 tweets • 4 min read
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
Jul 23 • 10 tweets • 3 min read
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.
Jul 22 • 10 tweets • 4 min read
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.
Jul 19 • 12 tweets • 4 min read
How the rich get richer:
Buy profitable businesses.
Here’s how you can steal their playbook and buy a cash-flowing biz without their millions:
Three reasons why buying beats building a business from scratch:
- 45% of new businesses fail within 5 years
- Most entrepreneurs make only $67k/year
- First 3-4 years are unprofitable
Compare that to when you buy…
You inherit customers, systems, and profits from day one.
Jul 15 • 15 tweets • 3 min read
If you own a business and don't have a newsletter, you're missing out on your biggest revenue stream by far.
After sending 15M+ emails this year, here's why newsletters are still wildly underrated in 2025:
Most people grossly misunderstands the attention-conversion game.
Specifically, how to turn eyeballs (views) into money in the bank.
This concept is best understood by explaining the difference between a “rented” audience and an “owned” audience…
Jul 11 • 9 tweets • 4 min read
This guy’s one of the most well-known faces on earth, multi NYT best-seller, and has built many $100M+ businesses.
Fascinating person to talk to.
Here are 7 brutally honest truths on wealth, success, and media leverage from my recent chat with Gary Vee:
Parents Are Destroying Their Adult Children
If you still pay for your kid's life after 22, you're telling them you don't believe in them.
Gary gets DMs from depressed 28-year-olds on their parents' payroll. They know they're failing, and it destroys them.
Love your kids enough to let them struggle.
Jul 10 • 12 tweets • 3 min read
The difference between a $1M business and a $100M business:
Hiring operators.
After years of making the right & wrong decisions, here's the exact process we now use to find killer operators:
When it comes to hiring for this role, the stakes are always higher than you think.
A poor hire will cost you $200-300K+ and waste 6-12 months of momentum.
I've learned this the hard way numerous times—including watching an operator fund his family vacation while our business bled cash.
That’s a story for another day…
Jul 8 • 9 tweets • 4 min read
The best founders do one thing brilliantly…
Build systems.
It sounds easy. It’s not.
Here’s how we think about building systems for our portfolio of 30+ businesses:
Think of systems like a car. You need:
- Vision = windshield (see where you're going)
- Dashboard = gauges (track your speed)
- Goals = GPS (know your destination)
- Communication = alerts (stay coordinated)
- People = maintenance (keep everything running)
Miss any one and you're broken down on the side of the road.
Jun 30 • 10 tweets • 4 min read
I just spent 2 hours with a guy who sold multiple AI companies for $400M and built AI systems for the Pentagon.
He broke down AI's current influence and future dangers in ways I'd never heard before.
Here are the 8 most important things he told me:
AI Already Controls More of Your Life Than You Realize
Here's a stat that blew my mind: AI mediates 20% of your waking hours.
That's 1 out of every 5 hours you're awake.
The posts you see. The products suggested. The news that reaches you.
Most people have no idea how much AI is already shaping their thoughts and decisions.
Jun 27 • 8 tweets • 3 min read
I asked a former Secret Service agent her secrets to reading people.
7 lessons from Evy Poumpouras on manipulation, lie detection, and influence:
Stop Talking So Much
People think they need to explain themselves, defend their position, or fill every silence.
But when you're talking, you're gathering zero intelligence—you’re just focused on yourself.
The quieter you are, the better you become at picking up cues.
Jun 26 • 11 tweets • 3 min read
I love this quote from Marc Andreessen:
“If you know what you want, and you go for it with maximum energy, the world will often reconfigure itself around you much more quickly than you would think.”
5 cheap ridiculous things we did in the early days that oddly 10’xd our biz:
Before starting Contrarian Thinking, my resume looked like it was written by ChatGPT after six shots of whisky:
- Walmart model
- Reporter in Latin America
- Wall Street analyst
- Private equity investor
- Laundromat owner
- YouTuber
- Fund manager
Jun 19 • 9 tweets • 3 min read
Everyone's either excited about AI or thinks it'll steal their job.
I used to be on the fence.
Then I hired a full-time employee just to integrate AI into everything we do.
5 tools that made me 3x more productive in 6 months:
1. Whispr Flow
I don’t text anymore because of this.
All you have to do is hold Fn, speak naturally, and watch it transcribe your words perfectly like a court reporter.
It capitalizes names, adds punctuation, and even writes “fuck…” (it knows we never actually mean “duck” lol)
Jun 14 • 15 tweets • 4 min read
By 2030:
• $5,000,000,000,000 will change hands
• 2,300,000 biz's will be passed down
• 24,700,000 jobs are at stake
The greatest opportunity of the decade isn’t building something new... It's this:
As of right now…
Baby Boomers own nearly HALF of all private businesses in America.
Problem is, 10,000+ Boomers are retiring DAILY, and 70% of their businesses have nobody to take over.
But it wasn’t always like this…
Jun 11 • 15 tweets • 4 min read
The best founders do one thing brilliantly...
Hire.
It sounds easy. It’s not.
Here’s how we think about hiring for our portfolio companies:
Most owners hire like they're running a restaurant.
They think more cooks = faster service.
Instead, they get a kitchen full of people bumping into each other, burning food, and blaming everyone else.
That’s why hiring isn’t a numbers game.
Jun 10 • 12 tweets • 3 min read
The fastest way to build a memorable brand is to pick a fight.
Here's a simple framework to define your enemy and build a magnetic business (The 3 Vs):
Harley-Davidson figured this concept out in the 80s.
They were getting bodied by Honda and Yamaha's smoother, faster, quieter bikes.
So Harley said screw it.
They stopped selling motorcycles and started selling middle fingers.
Jun 7 • 12 tweets • 4 min read
I spent 90 minutes with Harvard professor Arthur Brooks, and he made me rethink what I knew about happiness.
Here's everything you get wrong about being happy:
According to Arthur, the pursuit of perfect happiness is a dangerous myth.
As much as we hate them, we need negative emotions because they keep us safe and alive.
They're defense mechanisms that signal when something's wrong around us.
Jun 5 • 9 tweets • 4 min read
I asked a former Green Beret how to raise a family in 2025.
7 lessons from Nick Freitas every father should hear about raising strong men:
Dads Should Be Dangerous
One of the core duties of dads is to protect.
That’s why Nick believes the world needs more fathers who are kind, but never weak.
If you can’t be violent in the service of your family, you aren’t peaceful.
You are harmless.
Jun 4 • 17 tweets • 5 min read
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.
Jun 3 • 14 tweets • 4 min read
5 businesses I'm investing in that don't give a damn about interest rates, market crashes, or tariffs.
Here they are:
July 2024, I became a co-owner in Resibrands.
It’s one of the fastest-growing home services franchise businesses in the US right now and we’re not slowing down any time soon.
Here's exactly which industries we're building in and why…
May 31 • 15 tweets • 4 min read
The cheat code to becoming a millionaire:
Sell things to rich people.
I met someone who made multiple millions from an $8,000 jet business. Here's how:
The wealthy operate differently.
You can get 1000x the reward with the same effort when selling to them.
That's why the richest salespeople in the world sell planes, yachts, and luxury cars.
But here's what most people don't realize about breaking into this world…