CS, the ex-journalist turned private equity investor who is known for her bold, no-BS advice on buying "boring businesses," building wealth through cash flow, and thinking like a contrarian.

Lessons I’ve Learned from CS: Think Different, Build Smart, Buy Boring

CS isn’t selling you a dream. She’s teaching you how to buy real cash-flowing businesses, how to build wealth in silence, and how to go where others aren’t looking.

Her journey from journalist to investor — with a portfolio of laundromats, car washes, and service companies — has flipped traditional startup advice on its head.

Here are the most impactful lessons I’ve learned from her content:

1. Buy Boring Businesses, Not Hype

"The boring stuff makes the real money."

CS specializes in buying "boring" small businesses like laundromats, HVAC companies, mobile car washes — the kinds of businesses that nobody brags about on LinkedIn, but quietly print cash.

What I learned:
Not all businesses need to be sexy to be successful.
Service businesses are often undervalued and underappreciated.
Look for boring problems with recurring needs — that’s where wealth hides.

💡 Lesson: Your million-dollar opportunity might look like a janitorial service.

2. Cash Flow Over Clout

"Cash flow gives you choices. Followers don’t pay your rent."

While many chase attention or followers, CS focuses on businesses that actually cash flow. She encourages creators and professionals to own profit-generating assets, not just build audiences.

What I learned:
Focus on revenue before reach. A small business that brings in $10k/month is more powerful than 100k followers. Freedom is found in profit, not popularity.

📈 Lesson: Prioritize owning income-producing assets over building personal fame.

3. Be a Contrarian — Then Prove You're Right

"The best investments are found in places other people overlook."

CS champions contrarian thinking — going against the crowd with evidence and boldness. She’s known for questioning common financial advice and showing how small business acquisitions can beat traditional career paths.

What I learned:
There’s less competition where nobody else is looking. You don’t need to invent something new — just see things differently. Contrarian = profitable if you do the work.

🚀 Lesson: Go left when everyone goes right — and back it up with strategy.

4. Acquiring a Business > Starting from Scratch

"Why build a business when you can buy one that already works?"

CS teaches the "Acquire, Don’t Build" philosophy — instead of starting from zero, she encourages buying businesses that already have customers, cash flow, and operations in place.

What I learned:
Buying a small business can be faster and safer than launching a startup. Many boomers are retiring — and selling their companies. SBA loans can help you acquire with little capital upfront.

🛠️ Lesson: Don’t start a business. Buy one that someone else already built.

5. Sweat Equity > Ivy League Degrees

"You don't need an MBA to build a million-dollar business."

CS dismantles the myth that you need elite credentials to succeed. She values execution, grit, and common sense over degrees. She herself has been in the trenches — dealing with broken machines, hiring plumbers, and negotiating deals.

What I learned:
The best business education is running a real business. Blue-collar entrepreneurship is wildly underrated. Don't wait for perfect — take messy action.

🧠 Lesson: Real-world reps beat academic theory, every time.

6. Freedom is the Goal — Not Just Wealth

"I don't care about being rich. I care about being free."

CS is crystal clear: money is a tool for freedom, not status. Her content constantly reminds us to chase autonomy, not just income. She walks her talk — living on her terms while teaching others how to do the same.

What I learned:
Build businesses that run without you. Don’t just buy back your time — protect it fiercely. Design your business around your lifestyle goals, not the other way around.

🕊️ Lesson: Wealth means nothing if you're a prisoner to your own business.

7. Distribution Is Power

"Whoever owns the customer relationship wins."

CS invests in distribution-first businesses — like newsletter companies, niche media, or companies with a direct pipeline to their audience. She sees content and audience as assets that multiply business value.

What I learned:
Building an email list is one of the most powerful business moves. Community + communication = leverage. Don’t just build a product. Build a tribe.

📬 Lesson: Own the audience, own the outcome.

8. Speak Loud, Play Smart

"Don’t ask for permission. Build something undeniable."

CS encourages creators and entrepreneurs to be unapologetically bold — in their opinions, their business choices, and their presence. But she always backs it with smart financial strategy.

What I learned:
You don’t need to be the loudest — just the clearest. Confidence without competence is a trap. Don’t be afraid to challenge norms — just be ready to show receipts.

🎤 Lesson: Boldness backed by business wins every time.

Final Thought

CS is not just teaching how to build wealth — she’s teaching a new way of thinking about entrepreneurship.

She shows that financial freedom doesn’t come from unicorn startups or crypto pumps — it often comes from buying boring businesses, printing cash quietly, and playing the long game.

“Build once. Get paid forever.”