You're not stuck, you're just alone at the top. Most entrepreneurs hit a ceiling, not because the opportunity isn't there, but because you're solving $10M problems with $1M strategies.
We just hosted ~1,000 owners, investors, and operators in Austin for 3 days.
It might’ve been one of the most fun yet brutally honest rooms in business. Acquisitions, AI, family, risk, and staying sane while the whole world gets louder… All of it was covered.
Thousands of conversations later, here are 31 observations:
Most people drastically underestimate the number of paths available to them in life. They think there are five good options when there are five thousand.
Meeting someone who’s actually doing the thing you want to do changes everything. It stops being a fantasy and becomes a roadmap. Once you see it, it’s a paradigm shift.
The average person can barely imagine how many weird, profitable, legacy businesses exist right under their nose. Not just HVAC and laundromats. Tool shops, seed distributors, niche manufacturers, you name it. And these aren’t side hustles.
One immersive weekend in the right room can replace five years of networking online. Bathroom breaks at Main Street Over Wall Street were probably more powerful than any Zoom room could ever be.
The 30-year career is dying. Reinvention every 3, 5, 7, or 10 years is becoming a new normal, even among business owners. Most young people will live multiple professional lives and have multiple career arcs. The ones who learn to adapt to AI will own the future.
The family business is cool again. Husbands and wives are building together. Fathers and sons. Siblings. People want to spend more time with their families and find ways to make money doing it.
“Fit beats hot.” The next generation of builders will care less about sexy industries and more about using their hands. We were meeting 19-year-olds saying they’d rather own a boring trades business that feeds their family than a SaaS dream that feeds their anxiety.
In-person is an obvious cheat code. We did a virtual 3-day event earlier this year. It was awesome and enabled affordable, large-scale participation (and we’ll do more of these), but in-person events go deeper and nurture relationships. It’s the difference between information and transformation.
Every deal being worked on over these 3 days, no matter how big or small, was really a discussion around incentives. Align them early, and magic happens. Misalign them early, and your trouble compounds.
The best negotiators are great at removing emotional logjams. Figure out what the seller truly, truly wants and offer them THAT. It may be legacy, certainty, peace of mind, or something else entirely. Solve for it, and they will work with you under better prices and terms.
“Industry agnostic” sounds sophisticated until you’re knee-deep in a mess you don’t really care about. You need to have a way to push forward when you’re on your knees in the dark, praying to God. Focus on an industry or an aspect of ownership that brings you a little light.
Hard truth: A business that’s hard to find a seller for today is likely going to be hard to find a seller for later. You need to ask yourself if you are okay underwriting that for the next 10 years, and you need to bake that into the price today. (Brought up during a live deal review for a tourism business located on a remote island.)
There is such a thing as muscle memory when it comes to dealmaking. The importance of getting in reps and remaining consistent cannot be overstated. We asked one owner how many deals he looked through to find his one. “Probably 1000.”
Everyone agreed on this: Business buying is not an easy path, but more than that, it is the sprint toward the starting point of a marathon. Successfully buying a business is the BEGINNING of the journey. Not the end.
Devote time to building relationships with business brokers. They talk to each other. They want qualified buyers. Meet them in person. Build a reputation. Come prepared with a deal box, prequalified financials, etc., and you’ll immediately jump ahead of 80% of buyers.
If buying a business at the sub $500k scale, you need to pay extra attention to key man risk and address it head-on. Pay attention to skill gaps and the seller’s customer relationships. “It is really hard to execute against key man risk,” one elite investor put it.
The business education industrial complex is on the brink of total disruption. People are entirely unsure what their kids should learn in school or even if they should learn in school. Things will look very different in 10 years, maybe even 5.
Technological disruption is coming for every small business, from healthcare billing to laundromats to logistics. But for many owners, that will be a good thing. Long-term, AI will drive disinflation among certain cost sectors. If you’re exposed to these as costs, you will benefit. If they are your business, it could hurt.
You’re an allocator of both time and money. Clearly define for yourself if you want to buy something that’s a true “investment” or more of a job with equity that gets you in the game. For some, the job may be the right place to start; for others, that may not make sense.
This came up dozens of times: Expect the unexpected. Always be negotiating lines of credit. Always make sure you have enough cash. When you buy a business, your business will not do what you think it’s going to do in month 1.
The world is increasingly polarized and defensive. Negotiation and communication are daily life skills now, and essential skills for owners and dealmakers. Framing facts matters as much as facts themselves.
Some of tech’s most prominent thinkers see a huge need for greater small business ownership. Joe Lonsdale put it this way: “Whether it’s AI, shipbuilding, or defense, there are huge downstream ecosystems powering these industries, and small businesses are essential to them.”
American manufacturing weaknesses are still a major national risk. Joe’s goal is to build the biggest shipyards in America. “You’d think 80 years after World War 2, we’d actually be more efficient at shipbuilding, but we’ve gotten worse as a country.”
Leadership from the Small Business Administration told us that deregulation, skilled workforce resources, and reindustrialization investments into small manufacturing businesses are just starting to come into play to address these issues. Time will tell.
We heard from a number of AI sector experts who made it clear that AI will give people more time to think about “finding their calling”, but that AI’s impact on work and career arcs will make determining this more difficult, as people feel less purpose. Ownership may help address this, they think.
Bill Perkins shared a great lesson: “All of my regrets basically come down to one thing: whenever I didn’t do my best. Whatever period of life you’re in, if you’ve chosen a dream, do your f*cking best to pursue it.”
Another great lesson from Bill: “You are always in an interview.” Every day, every introduction, every action taken or not taken, you are always in an interview. Live life this way and watch yourself step up to the plate.
Some of the things most broken in society stay broken because no one has the courage to fix them. That’s why courage is such a high-value characteristic and is so appealing to investors when accompanied by skill.
Incentives are king. Whether it’s a new hire, a government agency, a non-profit, or a single small business deal, it’s not about funding alone but about HOW you fund. So much business success can be traced back to incentive structures.
The goal is never to avoid risk but to win more often than you lose over a long enough time horizon. Jenny Just is a mom who built a multibillion-dollar investment empire. She showed us that risk-taking is a skill you can develop.
On that note, by far one of the biggest themes across this event was the need for more (smart) risk-taking. Billion-dollar founders shared lessons with us that they’d stolen from poker. Government leaders stressed plans to support more risk-taking, especially among small businesses. And, as one new owner told the room:
“You either control your destiny or you don’t. Either way, it’s a risk.”
-Team Contrarian
ONE LAST THING…
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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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