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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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 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…
May 28 • 13 tweets • 3 min read
Harsh truth:
Running a company is simply a game of prioritizing problems.
Here’s how to become the Chief Problem Solver in your business:
Want to know Elon Musk's "secret" to running Tesla, SpaceX, and 3+ other billion-dollar companies?
According to Marc Andreessen, it's simple:
"He shows up every week, identifies the biggest problem, fixes it, and does that 52 weeks in a row."
May 7 • 15 tweets • 4 min read
Opportunity nobody talks about:
Buying unwanted land.
With $10K and 7 days of work, I was under contract for 10 acres in West Texas.
Here’s how I did it (and why):
Step 1: Set clear “make or break” criteria
I wanted:
• 10+ acres
• Located in West Texas (near Marfa/tourist spots)
• No restrictions on land use
• Under $10K budget
• Close in ONE week
May 1 • 11 tweets • 3 min read
In 2025, more people are buying businesses than ever before.
Here are 8 revealing stats from our comprehensive survey of small business buyers:
1. Top industry to buy in
Home services. Overwhelmingly.
Followed by:
- Professional services
- Health & wellness
- Construction
Apr 30 • 22 tweets • 6 min read
SBA loans are getting their biggest overhaul in years.
If you want to buy a business in 2025, here’s what you need to know:
First, little disclaimer: SBA rules are crazy complicated.
This is the high-level overview, but ALWAYS double-check info you find online before applying it to your specific situation.
Here are 5 new policy changes that stood out to me:
Apr 23 • 10 tweets • 4 min read
This is Bill Perkins.
He's worth 100s of millions, a hedge fund manager, poker player, asymmetric thinker...
And my smartest mentor.
Steal his 7 principles on how the rich think differently: 1. You Have ZERO Risk
Most people are afraid of risk because their egos can’t stand looking like an idiot.
I remember being slightly mind-f*cked by Bill's idea that educated people have no actual financial risk.
Listen to him explain it here:
Apr 22 • 18 tweets • 4 min read
The system is designed to keep you comfortable, not wealthy.
This financial autopsy of a 36-year-old couple earning $350k proves it.
Look at these numbers:
I just analyzed this financial autopsy of a couple in the Detroit suburbs:
- 36 years old
- $350K combined income
- $700K retirement accounts
- $900K mortgage
Looks like the American Dream on paper... Let’s look at the monthly
Apr 12 • 12 tweets • 4 min read
Last year, I brought together 100s of business owners and asked them: what's the biggest thing holding your business back?
This is what they said (& how I answered):
1. Hires That Weigh Down Your Business
Q: How do you know you’ve made a right hire off the bat, instead of wasting a bunch of time and money before you realize they’re a bad fit?
A:
Apr 9 • 13 tweets • 3 min read
Stressed about what you pay in taxes?
Start a business.
Whether you run a VC-backed startup or freelance on the side, the US tax code favors business owners over everyone else.
Here’s everything you should know:
1 - Business Expenses
You can take a deduction for anything you use to run your business.. internet, phone, software, conferences (including travel)
Business owners can also deduct their home office square footage from their rent or mortgage (which W-2 employees cannot!)
Apr 5 • 15 tweets • 5 min read
Business scaling isn't rocket science.
But it is a science.
After working with 100s of companies, I can tell you the difference between the ones that plateau and the ones that explode comes down to these 3 levers:
Every scalable business needs:
- The right people (who)
- The right systems (how)
- The right focus (what)
Miss any one, and you'll hit a ceiling.
Let's break down each piece (and I'll share what most get wrong):