7 Lessons Learned Building Businesses From $0 to 9 Figures

Most people only see the highlight reel:

They see I helped build an investment business at First Trust that grew past $1 billion in assets under management, and that I’ve bought and built dozens of businesses doing over $100 million in combined revenue.

They know I also grew Contrarian Thinking from a single newsletter into one of the largest business advisory and media companies out there. And that along the way, we built Contrarian Academy into the largest acquisitions platform and BizScout into the second-largest marketplace for buying and selling businesses.

But what people don’t see is that I’ve also lost millions on bad deals, hired the wrong people, and made more mistakes than I’d like to admit… So I put together the 7 biggest lessons I learned from building businesses from $0 to 9 figures.

Steal my homework, learn from my mistakes, and level up your business.

Early in my career, First Trust handed me an assignment to build an investment business in Latin America. I know it sounds great on paper, but one of the only reasons I got the job was because no one else would take it.

I didn’t live there and I didn’t have a network there, so honestly, I was terrified of failing.

But I cowboyed up, went to South America, and was able to 10X the business through joint ventures and acquisitions until we passed $1 billion in assets under management.

While it was scary, that experience taught me something I’ve never forgotten:

Chaos creates compensation.

When everybody wants something, competition eats the opportunity. On the flip side, when nobody wants it, the math starts getting interesting. Which is why years later, while everyone was hunting for the next Uber, I was looking at washing machines.

So before you chase anything, ask yourself:

Remember, you don’t get paid big money for doing something everyone else is doing. You cash out by solving the problems everyone else avoids.

My first laundromat cost about $100,000 and generated about $65,000 per year. People weren’t exactly breaking down my door to invite me on CNBC to talk about it.

But I was working in finance at the time, and while I was making decent money, I’d figured out that I didn’t want my boss’s job. I wanted freedom.

So I started buying businesses that already had customers, employees, and revenue. Over time, that first laundromat turned into roughly 25 to 30 more, plus stakes in dozens of other companies.

When you start from scratch, you have to figure out:

But when you buy an existing business, most of those questions already have answers.

Of course, sometimes you end up buying someone else’s problems, and I’ve done that too. That’s why I’ve learned how to evaluate, acquire, and improve existing businesses. It’s one of the most valuable skills I’ve ever developed, and it’s what we teach in the Contrarian Academy.

Because while most people spend their lives hunting for a million-dollar idea, I’d rather find a business already doing a million dollars and figure out how to own it.

And your first deal doesn’t need to make you wealthy. It just needs to teach you, because once you’ve bought 1 business, you start seeing opportunities everywhere.

Before it was a giant company, Contrarian Thinking was just a newsletter based on a relatively unpopular opinion. While everyone else was talking about crypto and venture capital, I was over here talking about laundromats.

I wrote about “boring” businesses, cash flow, and the millionaire next door getting rich off cleaning up sewage. I believed (and still believe) regular people should buy businesses the way private equity does, and it turned out you agreed.

That newsletter eventually grew into one of the largest business advisory and media ecosystems, reaching millions of people. And suddenly we didn’t just have an audience. We had distribution.

And even Peter Thiel agrees distribution is king…

Once we had distribution, every new business got easier to launch. We built Contrarian Academy to teach acquisitions, Boardroom to help owners grow, and then BizScout to connect buyers and sellers.

Across those businesses, we’ve now served more than 16,000 people, helping them buy over $100M in assets. And we did it by sharing information people cared about.

While most companies pay Meta or Google every time they want to reach a customer, we spent years building an audience that wants to hear from us.

That’s the difference between attention and distribution. An audience can give you attention, but distribution gives you leverage. That attention (earned or bought) is only valuable if you can turn it into trust, customers, and outcomes.

A great product without distribution is a secret. A decent product with excellent distribution is an empire.

After dozens of acquisitions, I noticed finding good businesses to buy was still insanely difficult.

Some of our best deals came off-market, but sourcing them meant paying analysts to dig up companies and cold-call owners. The time/cost ratio was getting out of hand…

Which is why I ultimately bought a small business that helped people source off-market leads. That’s when I realized the problem was way bigger than I thought. Buying and selling small businesses is a huge industry, but it’s still running on outdated tech and scattered information.

So like any sane person, I invested several million dollars of my own money, raised outside capital, and assembled an entire team of badasses to run the thing. Thus, BizScout was born. And in April 2026 we announced a $5 million seed round with backers including Tinder founder Sean Rad and former Coinbase CTO Balaji Srinivasan.

We also partnered with Transworld Business Advisors and Viking Brokerage, 2 of the largest brokerage networks out there. BizScout is now growing rapidly, offering serious buyers a place to quickly find the kind of off-market deals that used to take ages to source.

Two years into business, we have:

Here’s the takeaway: I didn’t dream up BizScout in a conference room. I found it because I was already paying to solve the problem.

So take a look at what you keep paying for that doesn’t work, or the task your team grinds through by hand every week. Because sometimes the best way to find a business is to be a really pissed-off customer.

I’ve made some expensive mistakes. If you’re in business long enough, you’re bound to make a few blunders…

One of my worst involved a private equity deal where we were dealing with approximately $12 million in exposure across the investment group, when we discovered fraud.

Money had been taken, financial statements had been manipulated, and someone involved left the country. We were able to recover some of the money and rebuilt parts of the business, but it still wrecked me. I don’t think I slept for weeks…

And what bothered me most was that I knew how to analyze the business and model the deal. We just trusted the wrong person.

The biggest mistakes in business are usually WHO mistakes, not HOW mistakes.

The wrong partner can sink a great business, the wrong executive can cost you years, and the wrong seller can make fake financials look real.

So now I spend as much time sizing up the people as I do the numbers, because trust is not due diligence.

In the early days, I wrote every piece of copy, sold every product, hired every person, and made every decision at Contrarian Thinking.

That stopped working the moment we grew into multiple companies with a (much) larger team.

We needed leaders who could run entire functions and companies without waiting for me, so we built out leadership across Contrarian Thinking, our acquisition education and advisory businesses, our investment fund business and BizScout.

And I had to learn something many founders hate hearing. If every important decision requires you, you don’t have a business you have a job with a dictator for a boss… you.

I see the same thing all the time in businesses we look at buying. The revenue looks solid, but the owner is the top salesperson and the only one who knows how anything works. So what happens when that person leaves? The business falls apart.

That’s why you have to learn how to delegate.

But before I hand anything off, I like to fill out what I call the 6D Execution Brief.

Try it this week on something you’ve been holding onto. If you can’t answer all 6, the handoff isn’t ready yet. Because just telling someone to “take ownership” isn’t enough. People need authority, clarity, and accountability.

And leaders need to stop confusing being needed with being valuable. The goal isn’t to be the most important person in your company, it’s to build a company that can succeed without needing you in every meeting.

When I started Contrarian Thinking, I didn’t set out to build a media company. I just wanted to make ownership more accessible.

But as we grew, I noticed each business made the next one stronger.

Our content brought in people curious about ownership, who wanted to learn how to find and buy businesses. So, naturally, we built Contrarian Academy.

When those buyers needed deals, we built BizScout.

And once they owned something, they needed help running it, so we built the advisory programs, playbooks, and operating systems that became Boardroom.

Meanwhile, our own experiences gave us real stories, data, and lessons to share with you, and you helped create opportunities for the businesses. I call that advantage Operating Systems + Ecosystem + Audience, because each part feeds the others. It’s what a Deloitte consultant might call “synergy.”

That’s a very different strategy from building a business, selling it, and starting over from zero.

Rather than pump out more and more products as fast as possible, I’ve come to believe that the best businesses are the ones where every new product makes the existing ones more valuable.

One business can certainly make you rich, but an ecosystem of businesses can create compounding advantages that a siloed portfolio never could. It’s like the difference between putting your money in a standard savings account and investing in the stock market. You can build one up slowly, but the other can take off in ways you can’t predict.

The goal isn’t to own a random collection of companies. It’s to own businesses that make each other better.

After all of it, here’s what changed how I define success: making money and owning your life are different things.

I’ve met people making millions who can’t take a vacation, and I’ve met owners of boring little businesses with more freedom than CEOs running companies 100x their size.

(And if you’re an owner with a business doing $500K+ a year, I’m hosting the Growth Accelerator Workshop from October 20-22, in Austin TX.

It’s designed to help you scale past your sticking points, show you where you’re losing revenue, and turn you into a delegating black-belt. But it’s not for everyone, so if you’re interested, you can apply for your seat HERE!

Look, I’ve been the person grinding ridiculous hours for someone else’s company, and I’ve been the owner, so I know which one I’d pick again. The goal was never just to build a nine-figure business. Not really. It was to build assets that produce cash flow, create opportunities, and give me more control over my life.

Because you can win the game everyone else is playing and still lose the life you wanted.

After all, a bigger job is still a job.

Own or be owned.

-Codie