Enjoying this article?

One email, two high-value newsletters straight to your inbox. Each one delivers everything you need to be smarter than a private equity investor.

Contrarian Thinking

Contrarian Thinking's 2025 Annual Letter

February 27, 2025
18 min read

Contrarians,

First, thank you. Trust is a rare currency in today’s world, and you’ve placed yours in our hands. We don’t take that lightly. Inside this letter, you’ll find our annual update — where we’ve been, what we’ve learned, and what we’re building for you next.

We vs. Me: Creating a Movement

The American Dream is built on ownership. Today, ownership feels out of reach for far too many. Research shows that across the political spectrum, while faith in corporations, media, universities, banks, and government continues to decline, small businesses are far and away the most trusted institution in America. Main Street remains a cornerstone of economic stability. We aim to bring it to the forefront.

My father always told me, “You can be selfish or great, but you can’t be both.”

I remember the moment I knew my time in traditional finance was coming to an end. I was walking with my CEO — my boss — laying out a vision for the future. We needed to get on the internet, I argued. We needed to share our strategies, teach others about investing, and leverage email and social far more than we needed to sit in boardrooms and take partners out for steak dinners.

He let me go on for a while. Then he looked at me and said, “Codie, here, we get rich quietly.”

And just like that, I knew my last day was coming sooner than I had planned. We had two fundamentally different views of the world. His was built on exclusivity — keeping knowledge and capital behind closed doors. Mine was built on access, leveraging technology, transparency, and attention to create a new kind of advantage. He wasn’t wrong; being public is often not fun, but it is the future.

Increasingly, intelligence, capital, and deal flow are table stakes. But relevance? That’s real leverage. The most valuable asset isn’t money — it’s attention, and at Contrarian Thinking, I decided we’d put that to work. Three years later, I’m still friends with that CEO. I learned plenty from him. But I have zero regrets about the path we chose.

At the core of Contrarian Thinking is the belief that “getting rich quietly” is outdated. Our goal is simple — help 1,000,000 people learn to become financially free, and create 100,000 new owners. We believe wealth isn’t a zero-sum game, that it scales better when you build alongside others. So we started with a hypothesis: If we taught more people how to do deals while doing deals ourselves, what could happen?

  • Maybe we’d unlock more deal flow than we ever imagined.
  • Maybe we’d build a stronger network than traditional firms could dream of.
  • Maybe we’d create more buyers, sellers, and operators for the businesses we acquire.
  • And maybe we’d make the world a little better by driving wealth to Main Street.

We could have taken the traditional private equity route, buying businesses, running them behind closed doors, and flipping them from one fund to another. Instead, we built something different: an academy, a brand, a movement, a community of business builders. Of course, breaking from tradition comes with its fair share of… feedback. Here’s what we’ve found:

  • The more truth you share, the more resistance you face.
  • The less you’ve built, the more you criticize.
  • The more you help the many, the more the few push back.

Yet, we keep going. Doing things with purpose isn’t always easy, but it’s always worth it. I saw that firsthand watching my husband dedicate a decade of his life to the military — certainly not for the money, but for the mission. That lesson stuck with me. Wealth matters, but how you build it and why matters more.

Our goal isn’t just to create one of the largest financial education and media companies; it’s to create a generation of Main Street millionaires. This country is better off when there are more owners. And we’re just getting started.

2024: The Year of “Full Send”

Every year, we pick a phrase to define our focus. In 2024, it was “Full Send” — no half-jobs, no playing it safe. The goal was simple: leave it all on the field, and I think we did. Frankly, 2024 was relentless. High highs, tough challenges, and no shortage of lessons. But when we look back, it’s clear that we pushed harder, bet bigger, and built faster than before.

What I started as a newsletter in 2020 is now a brand closing in on 10 million followers across major media platforms. We now create engaging content about business, ownership, building, and scaling, reaching hundreds of millions of eyeballs annually through articles, videos, speeches, podcasts, courses, and more. In 2024:

  • We started a new video series where we tour and unpack real Main Street businesses. I still chuckle when called a “YouTuber,” but I’m proud of our team. It’s the future of media.
  • We launched the BigDeal podcast, a long-overdue excuse to sit down with Tulsi Gabbard, Scott Galloway, Chris Voss, Bryan Johnson, and more.
  • We scaled our content engine, doubling down on long-form writing, social content, and video education to help more people take action.

We also hit the road hard in 2024, speaking at 30 events across the U.S. and connecting with ~38,000 people live. Some of the highlights:

  • Main Street Over Wall Street: We hosted 100’s of entrepreneurs from our Contrarian Community in Austin for a multi-day deep dive into ownership, acquisition, and connection.
  • Owner Workshops: We led intense workshops for business owners with $1M+ in revenue.
  • Main Street Millionaire Live: We brought together 500 in-person attendees and 20,000 online participants for a massive ownership celebration.

Running a media company at this scale isn’t cheap. Here’s what we gave away in 2024:

  • 104 long-form, detailed articles.
  • 2,831 videos across platforms.
  • 1,231 minutes of free educational YouTube content.
  • 36,000,000+ total newsletters sent via email.
  • 36 free templates & guides — resources built to help people execute, not just learn.

And then, I took everything I’d learned and put it into a book.

The Book That Kicked Off a Movement

In late 2024, we published Main Street Millionaire, a no-BS guide to buying businesses and building wealth on Main Street. I’ll be honest: I wasn’t sure how many people would buy a book on acquisition. Most people don’t realize this, but only around 10% of Americans own businesses, if not less, and far fewer will ever complete an M&A transaction. So let’s just say I wasn’t expecting the book to fly off the shelves. But I was wrong.

The book hit the New York Times Bestseller List and became the #1 book on Amazon in the Small Business, Startups, and Entrepreneurship categories. At points, we even outranked Martha Stewart, Dolly Parton, and Snoop Dogg, which is hilarious. But what really matters — the most quoted line from the book wasn’t from me. It came from my 99-year-old grandmother: “Business ain’t for p*ssies.” She’s right, of course. Another thing we’re proud of — the reviews weren’t just from people liking the book — they were from people actually using it.

That’s the real measure of success here. Not bestseller lists, not follower counts, but whether people are actually taking action because of what we’ve created.

More Owners, More Deals, More Impact

In 2024, our Contrarian Community Business Academy became a true “incubator” for small business ownership and growth across the country. With thousands of individuals engaged in our educational programs and over 1,000 in our primary program, we’re creating a talent pool of builders.

In 2024, our team of 9 facilitators, 4 community concierges, and 11 member ambassadors hosted hundreds of office hours and live calls with our members, providing guidance. We also brought the community together through dozens of in-person events. To date, members of our community have reported acquiring over 200 businesses. Here’s what’s coming next:

  • A 1:1 Concierge Program, every new member is assigned a personal concierge from day one.
  • Monthly calls with sector experts, where specialists from industries like HVAC, law, marketing, and more will share insights and answer member questions.
  • Event-in-a-Box kits to help members organize meet-ups in their areas.
  • Dominium, premier program for experienced business owners with revenue of 7 figures or more. As of this publication, the average member joined the program with revenue of 8 figures. We’re proud to attract such an elite group.
  • 2025 will be a year of learning, challenges, and hopefully many achievements. I don’t say lightly that I believe we’re rivaling the best MBA M&A programs if you want to learn to buy and build a Main Street business.

Investing in the Future of Main Street

The saying goes: “Give a man a fish, feed him for a day. Teach a man to fish, feed him for a lifetime.” I think that’s two-thirds right. What’s missing? Leverage. Because if you teach a man to fish in excess, he won’t just feed himself — he’ll have enough to feed others. Maybe even you. That’s exactly how our flywheel works.

Every deal, every investment, every move we make, aims to feed into a larger system, one where the more people we connect with, the more deal flow, builders, operators, and investors we can work with. Like a waterwheel gaining momentum, the early friction is high, but once it spins, it moves with beautiful force. That flywheel is in motion. And in 2024, it delivered in a big way.

The ResiBrands Deal

Last year, we became owners of ResiBrands, one of the fastest-growing home services franchise groups in America. Our brands include painting, window cleaning, garage renovation, roofing, and handyman work. You may be wondering how the deal came about. The answer may surprise you.

We first discovered ResiBrands through our media team, when we were covering the company for a story. That story turned into an introduction, which developed into a relationship and eventually one of our holding company’s largest investments to date. Since then, we’ve rolled up our sleeves to drive the business forward and help the team navigate daily challenges.

That’s the power of our ecosystem — we are gaining access to really powerful investment opportunities that are impacting real lives. A number of members in our Contrarian Community are now franchisees of Pink’s, That 1 Painter, and Garage Up. We’ve even seen ResiBrands leverage Drillbit, a company in our venture portfolio, to optimize its operations. Here’s more on what ResiBrands accomplished in 2024:

That 1 Painter

That 1 Painter grew to 420+ signed units across 34 states, becoming the largest painting company by territory in the U.S. by embracing a “give to get” mindset. Through their Paint It Forward program, the team painted nearly 100 homes free of charge last year and plans to do the same this year. Their hyper-local marketing and SEO-driven approach proves that serving first is leading to lasting growth.

Pink’s Window Services

Pink’s expanded to 170+ signed franchise units across dozens of states. From crisp uniforms to clean, nostalgic branding, they’ve built a premium reputation — so much so that Glen Powell rocked a Pink’s uniform in Netflix’s Hitman. The lesson? Dress like a pro, get paid like a pro.

Garage Up

Garage Up is tapping into a competitive but valuable market, rebranding as the best full-service garage renovation company and leveraging unique collaborations to help expand to dozens of signed franchise units.

Monty’s Handyman Services

Monty’s is turning a nameless industry into a timeless brand. After surveying thousands of people and finding less than 1% of them could name a single handyman company, ResiBrands saw the gap — and filled it. Now, they’re launching this concierge-style service.

Action Exteriors

Action Exteriors proved that expertise pays off. By partnering with roofing business veterans, the team avoided costly mistakes and launched with 4 franchisees covering 22 territories. The lesson? Cutting corners costs more in the long run — hire pros from the start.

This is what a bias for action looks like in real-time. I’m so proud of the team at ResiBrands and our CEO Steven Montgomery. Here’s to making blue-collar work sexy again.

Scaling Up Our Work in Venture

While we continue investing in blue-collar spaces, we’re also backing the technology that will power Main Street’s future. 2024 was a defining year for Contrarian Thinking Capital, with 15 investments, including 12 new companies disrupting industries like finance, garment care, pool services, agriculture, robotics, the future of work, defense, logistics, and trade. These additions bring our total venture portfolio to 28 businesses, many of which are scaling aggressively.

In this time, we’ve invested in startups alongside some of the world’s top venture firms — Sequoia, Bessemer, A16z, and others — underlining our capability to put capital to work across highly competitive opportunities time and again.

Recently, we’ve seen exciting progress across our portfolio. Figure AI, a new leader in humanoid robotics, is reportedly in talks to raise $1.5 billion at a staggering $39.5 billion valuation, a sign of how automation is expected to drive productivity across entire industries — including Main Street businesses. Another portfolio company, Shopgenie, recently joined forces with Tekmetric, the leading cloud-based auto repair shop management system, creating a powerhouse platform for Main Street auto shop owners. Saronic, an Austin-based startup, just raised a $600 million Series C to build Port Alpha, an autonomous ship factory.

Beyond these headlines, 2024 was a strong year for several other companies. To name a few:

  • Cents, the leading business management platform for garment care SMBs, closed a $40M Series B to expand its capabilities in a sector long overlooked by technology.
  • Fitness platform Ladder secured over $100M in new funding to fuel its 200% growth trajectory.
  • PostPilot, the fastest-growing direct-mail marketing company in the U.S., secured a strategic investment from Summit Partners, with Klaviyo’s founders participating.
  • Doola secured a strategic investment from HubSpot to expand support for the next generation of business formation, bookkeeping, and tax filing globally.

Most importantly, we’re not just investing — we’re working hard to improve how we drive meaningful impact. Increasingly, our media, education, and investment platforms will be working together, giving us a unique edge that traditional firms will struggle to match.

  • Media drives unique access and expertise.
  • Education creates new business builders and operators.
  • Capital fuels the best products and services.
  • Our audience and expertise help scale them faster.

Our first fund is closed to new investors, and our second fund is coming soon. We think this flywheel is just getting going. In 2025, we’ll be pressing the gas even harder.

BizScout: Scaling Up a Strong Foundation

Since launching in 2024, BizScout has quickly grown into a robust marketplace tool for business buyers and sellers, onboarding 60,000+ users and facilitating 600,000+ deal lookups. As we head deeper into 2025, we’re focused on expanding and improving deal flow, enabling better valuation insights, and making buyer-seller connections more seamless.

We’ve added useful new calculators to the BizScout platform, enabling buyers and sellers to make more informed decisions quickly. These include tools for calculating net working capital needs, deal affordability, exit modeling, valuation multiples, and buying power.

Beyond better analysis, we’re enhancing buyer and broker matchmaking. New features will let buyers showcase their acquisition criteria and financial qualifications, helping brokers connect them with the right opportunities faster. We’re also launching a dedicated broker page that will simplify onboarding to our Partner Broker Program and drive more high-quality deal flow.

With these upgrades, we’re also fine-tuning how users discover deals. Dealbox, our personalized marketplace feature, will allow users to filter listings based on their specific investment preferences — ensuring they see the most relevant opportunities while saving time.

Building this platform hasn’t been easy or simple. We’ve navigated technological challenges, team adjustments, and intense competition. However, with a strong pipeline of new tools, an expanding network, and a proven growth engine, 2025 is about scaling BizScout into the go-to marketplace tool for small business transactions.

High-Performing Teams: Calling Our Shot

At Contrarian Thinking, we believe that a team always beats individuals. The most important work we’re doing right now might not even be in media, small business, or venture, but in developing a team and network of top-tier talent. In the end, it won’t be our ideas or ambitions that define how far we go. It’ll be our people.

I’ve never subscribed to the idea that companies are families. That’s a beautiful lie told by leaders who don’t want to make hard decisions. Companies aren’t bound by blood — they’re bound by mission. A great team isn’t about comfort — it’s about performance. You’re together for as long as it takes to win, or until one of you decides it’s time to hang up your shoes. And if you want to win? You have to play like it.

The Mentality of High-Performing Teams

The best teams walk a fine line. On one end, they must play as individuals, delivering results at the highest level, holding themselves accountable, and taking ownership of results. On the other end, they must move as one, work cohesively, push each other, and play for the bigger goal. No individual performance? No win. No cohesion? No win.

Winning is a cruel mistress. She’ll demand all of you. She’ll let you get so close you can almost feel her, then pull away at the last second. She’ll make you wonder if it’s even possible. But when you do win, when you pull it off against the odds — that’s what makes the work matter. That’s why at Contrarian Thinking, we don’t just set goals. We call our shots. You’ll hear it in our office: “Hold my beer — I’m calling my shot, watch me hit X metric.”

The Reality of High-Performance: Friction & Fire

If there’s one thing I’ve learned about top-performing teams, it is they’re not always calm, cordial, or easy. Pressure is part of the game. People these days don’t seem to like scoreboards. We do. Winners want to know what they’re capable of under pressure.

Audacity. That’s one of my big words for 2025. Having the audacity to aim high, say it out loud, and back it up with action. You don’t get better by coasting. You get better when people challenge you. Iron sharpens iron — but that requires fire, sparks, and hammers.

I think a lot about the rivalry-turned-partnership between Michael Jordan and Scottie Pippen. At times, they hated each other. They were relentless, difficult, and hard to deal with. But they were also driven toward greatness. That’s the line we try to walk at Contrarian Thinking — relentless competition of ideas, camaraderie of equals, and the expectation that we push each other to be better.

Losses from the Season

This year, we had a majority of wins, and I’m damn proud of it. It was, candidly, brutal pulling all of this together. We set big goals, and we hit many of them. But I’ll be the first to say: There’s nothing like a humiliating loss or mistake to challenge a team. We had several of those:

  • Shutdowns of companies that were underperforming. Painful.
  • A cash-strapped company we had to work very hard to turn around.
  • Payment providers nuking revenue for one of our new businesses — multiple times.
  • A bad hire we didn’t cut fast enough, and it cost us.
  • Multiple members of our teams lost very close loved ones.

Here’s the thing, though. When you go through real struggles as a team, something shifts. Trust deepens. Resilience is forged. There’s a Zen proverb I love: “Despite what happens in life, chop wood, carry water.” At Contrarian Thinking, we call it, “Choose your hard.”

For the past few years, we’ve been rookies. Now, I think, we’re coming into our own — not because of the wins, but because of the mistakes we overcame. I’m proud of this team. We’re playing for a championship. And as far as I’m concerned, it’s ours to lose.

Everything Changes

There’s a great story of a Buddhist monk known for teaching enlightenment. At the end of a very long lecture, one of his students cried out in frustration, “I don’t understand anything you said. Can you not tell me one simple, real thing about Buddhism?”

The monk replied, “Everything changes.” That seems about right. The only thing I know for certain about the future is that everything changes. If we are in the game to win, we had better not stay in the same place.

By certain metrics, we are arguably one of the fastest-growing business media and investment companies in the world. But I certainly don’t believe we are the best. To get there? We can’t just repeat last year’s playbook. Momentum requires creation. So this year, expect us to surprise you with a few moves you didn’t see from us last year.

Looking ahead, our word for the year is simple: Flow. Like the waterwheel, we are lining up our team, our business units, and our flywheels to flow. Everything changes. We intend to drive that change.

To the builders,

Codie Sanchez
Founder and CEO, Contrarian Thinking

Share
contrarianthinking.co/newsletter-articles/annual-letter-2025