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Contrarian Thinking

How We Turned 1 Email Into a Portfolio of Profitable Businesses

March 6, 2026
11 min read

Here's what we've built at Contrarian Thinking:

An advisory business with ~3000 members. A venture capital firm. A New York Times bestselling book. A top-10 business podcast. A 1,000-person annual conference. A software platform for buying and selling businesses. Ownership stakes in a portfolio of Main Street companies. A media operation reaching 12 million people. A team that outgrew two offices in 12 months.

People often ask how we built all of this.

They're usually expecting some sophisticated answer about capital allocation or brand strategy or a lucky break. The real answer is comical in its simplicity:

We sent some emails.

Yup, one of the most important business moves we ever made cost nothing and took 20 minutes to get off the ground. No investors. No permission. Just a decision to start a newsletter and actually send it to people.

Here's how it happened and how you can steal the model.

We Started With Something Mega-Cringe

5 years ago, we grabbed every contact we could. And we wrote them a newsletter out of nowhere.

Just an honest, unpolished note about our goal, plus some thoughts on money and business ownership. The stuff we heard people in finance talk about behind closed doors but never really say publicly.

We almost didn't send it. Spent a solid chunk of time convincing ourselves it was a terrible idea. Then we got the hell over cringe mountain and hit send.

Seen on X @ArjunMahadevan

Even Harley Finkelstein, President of the $200B company Shopify, agrees. “Cool waits for results; cringe creates them.” Hey, it worked for us. 102 people opted in. That was our launch list.

What followed was 4 genuinely chaotic weeks focused on growth. LinkedIn posts, Facebook groups, podcast appearances, lead magnets, tagging bigger accounts, begging friends to forward it. Plenty of things that flatlined completely. A few that worked better than expected. A lot of figuring it out in real time with no real playbook.

Today, everyone wants distribution. But few actually want to build it. They want the shortcut. But the reality is rarely neat and tidy.

We posted the full day-by-day breakdown on Reddit 5 years ago if you want the details. It's dated, but the bones still hold. It tells you exactly how we got to 10k subscribers in 30 days.

To be honest, in hindsight, timing helped. In 2020, people were sitting at home actively looking for content like this. Demand exceeded supply in a way that doesn't come around often.

Today, though, all of this is just as possible. The space is more crowded, and you need proper infrastructure to do this well. But there are better tools.

If you're not using beehiiv for this, you're falling behind...

Big brands use beehiiv. But so can anyone. And that's the whole point. We used beehiiv to send you the email you're reading right now.

Using it feels like having an automation whisperer / analytics nerd / website sorcerer / growth goblin on hand 24/7, but without the payroll.

That's why we love it, and why we invested in the company.

(Also, the team wanted to help you out: use the code CODIE30 for 30% off for 3 months.)

From 1 email → businesses, investments, and media

Here's what 95% of people on Earth have never thought about when it comes to email:

A newsletter isn't just how you reach people. It's how people tell you what to sell them so you can… make money.

Most businesses spend fortunes trying to understand their customers. A newsletter inverts that entirely. Every send is a data point. What gets replied to. What gets clicked. What question shows up over and over, worded differently each time, but asking the same thing underneath.

After enough time, you stop guessing what your audience needs. They've told you. Clearly.

Most people hear "distribution" and think: views, content, followers. Post more. Go viral. The end. That's thinking too small.

We treat distribution as the central hub of every business we run. Everything else is a spoke. It fuels how we find customers, source deals, test products, and hire people. It tells us what to build before we build it. It gives our portfolio companies an unfair advantage the day we get involved.

Reid Hoffman said it plainly: “A good product with great distribution will almost always beat a great product with poor distribution.”

Here's exactly how that played out for us.

  • The Contrarian Academy: The inbox kept asking the same question in a hundred different ways. How do I buy a business? Where do I find deals? How do I learn to understand the numbers? Today our Contrarian Academy has 2,500+ active members and many millions in collective transaction value. Many of those members found us through the newsletter. So did several of our best hires.
  • Our investments: We didn't build a VC fund and then find an audience. We built an audience and then a VC fund grew out of it. When a group of business builders trusts your thinking, deals start coming to you.
  • The Growth Boardroom: Business school is largely focused on theory. Accelerators teach startups. Nobody was doing anything useful for the Main Street operator working through a real hurdle in real time. We knew that gap existed because our readers told us, loudly and repeatedly. So, recently, we built the Growth Boardroom for them. Today we serve hundreds of business owners across sectors.
  • Our events: The newsletter readers told us they wanted to be in the same room as each other. So we built the room. In 2025, 12,000 people came to our virtual events and well over a thousand showed up in person. We're expanding this aggressively: multi-day workshops, camps, and an annual summit.
  • BizScout: For years, one of the most common questions in our inbox was some version of: where do I actually find a business to buy? We got it so many times we eventually just built the answer in BizScout.
  • The media: Reputation is the whole game. And you can't buy it. Before anyone knew who we were, we spent years showing up in the inbox every week with something we thought was genuinely worth reading. That trust is what made everything else possible down the road. Top 5 podcast. 2 million YouTube subscribers. 3 million on Instagram. 12 million across all platforms.
Your Call to Arms

The cool thing is, we still believe email will be a wildly powerful channel in 2026 and beyond. More crowded, but more capable, too.

Email is intimate. Direct. Personal. It’s 1-to-many but also 1-to-1. There’s no “views” counter at the bottom. Just a chance to talk straight to another human being. That’s why it’s a great on-ramp into an ecosystem.

Every time we send something out, we get replies from real humans. It’s awesome! Sometimes you’re annoyed at us. Most times, we get to hear about your wins, challenges, and ideas. All of it is priceless.

It really doesn’t matter if you’re emailing 100,000 people or 10 people. WHO those people are is what matters. We don’t take it lightly that you choose to open these emails, learn something, and be part of this journey with us.

Thank you for being here.

-Team Contrarian

The information contained here is educational, may not be typical, and does not guarantee returns. Background, education, effort, and application will affect your experience and the profitability of any business. Individual results may vary.

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