Welcome Note
Thanks for tuning into the twelfth episode of The Advantage. A short, weekly note where I share what I am working on, something worth watching, a lesson from history, and one practical edge you can try right away.
This week's theme is about getting out of the AI doom loop and into what I believe is the great proprietor awakening. In my opinion, this is the best time ever to start or buy your first business. From disruptive companies that can change the world, to the next great CPG brand, to the boring businesses we rely on every day but rarely think about, this is the best moment since the western expansion of the early Gilded Age to carve your own path. Also, golf season is almost here, and it is never too late to yell "fore." Your business Rolodex will thank you.
A Correction, And A Deeper Look At Why It Is Easier Than Ever To Start
Two weeks ago, I wrote that when I started Freshly in 2012, it took about $10 million to find out whether the idea worked. A few people emailed me after reading that line, and they were right to push on it. That number was a bit of an exaggeration. The more realistic number is closer to $1 million, which is still a huge amount of capital to commit before you really know whether you have something.
That said, the core point holds, and I actually think it becomes more powerful when stated more precisely. In 2012, starting Freshly still required a warehouse, a full-stack engineering team, a logistics operation, and real upfront investment before we had enough signal. Today, I believe we could answer that same question for under $50,000. That is not just a cost savings. It is a fundamental shift in how fast entrepreneurs can learn, test, and move.
I wanted to dig in more, which I did in this week's blog post "This Is the Best Time Ever to Start a Business," because this idea connects directly to this week's theme. If it is now dramatically cheaper to research, validate, and operate a business, then more people should stop waiting for the perfect startup idea and start building. That is one reason I liked this week's Worth Watching so much. It is a good reminder that ownership does not have to start with something glamorous. In many cases, it starts with something simple, useful, and proven.
Boring Business that Make Millionaires
This week's Worth Watching is a 19-minute video called "6 BORING Businesses that Always Make Millionaires (90% success rate)," about six "boring" businesses that almost nobody dreams about, but many more people probably should. The reason I liked it is not because of the specific list. It is because it makes a point that more aspiring entrepreneurs need to hear: you do not need a revolutionary idea to start building toward ownership. In many cases, the better move is to start with something simple, useful, and proven. That is especially true now, when AI, software, and modern operating tools have made it easier than ever to research, test, market, and run a traditional small business. For someone who wants to be their own boss, boring may actually be the best place to start.
What I loved about this video is that it pushes back on a bad assumption a lot of people still carry, which is that ambition has to look impressive. A lot of would-be founders are still waiting for the app idea, the breakthrough concept, or the business that sounds big enough to justify the leap. Meanwhile, they overlook businesses with real demand, understandable economics, and a much clearer path to ownership. The video makes that point well. It shows how simple businesses can become meaningful businesses when the operator starts lean, learns the model, validates demand before spending heavily, and focuses on one market before expanding. I also liked that it did not frame simplicity as small thinking. That is the real takeaway here. For a lot of people, the smartest entrepreneurial move is not waiting for the perfect idea. It is starting something and getting in the game.
→ Simple Does Not Mean Small: The video's best point is that "boring" businesses are often dismissed for the wrong reason. They may not sound exciting, but they are usually much easier to understand, test, and operate than a high-concept startup idea.
→ Start Lean First: One of the recurring lessons is to keep risk low in the beginning. The creator gives examples of validating demand before making major investments, whether through drop shipping, simple marketing tests, or manually proving there is a real customer before building too much.
→ Local Focus Matters: The video repeatedly emphasizes starting in one local market, learning that market well, and building systems there before trying to expand. That focus is what gives a simple business a chance to become durable.
→ Ownership Is More Accessible Than People Think: Underneath all six examples is a bigger idea. With better software, better distribution, and AI making research and planning easier, traditional small business ownership is now more accessible for people who are willing to start simple and execute well.
AI and the Frontier Era Within the Early Gilded Age
From roughly 1850 to 1890, America still looked much more like a nation of proprietors than a nation of employees. A conservative read is that frontier-era America likely had something like 25% of workers operating as clearly self-directed proprietors or owner-operators. The frontier created millions of proprietors: farmers, traders, merchants, builders, and local operators working for themselves because productive land was available and the barriers to entry were low enough to make action possible.
Economic structure follows the cost of independence. When the tools, infrastructure, and access to customers are cheap enough, more people work for themselves. When those things become expensive and complex, institutions win and individuals get absorbed into them. The frontier was never just about land. It was accessible leverage. That is what created proprietors at scale.
AI may be returning us to an older American default: proprietor over employee. The story may not be the great "AI job loss." It may be the great proprietor awakening, not because everyone will suddenly become self-employed, but because one capable person can now do work that once required a team, real capital, and institutional backing. That is the shift people are underestimating. This is not a normal cycle. It is a frontier moment. In 1948, self-employment still accounted for 18.5% of U.S. employment. Today it is about 10.2%. The long arc of the last century was consolidation into firms. AI is one of the first technologies in a long time to meaningfully push in the other direction, collapsing the costs of research, testing, building, selling, and operating.
Take Up Golf
Golf is one of the only sports I know where a pro and someone who can barely keep it in play can still go out, compete, have a great time, and see the match come down to the last hole. The handicap system makes that possible. It turns a game with huge skill gaps into one that can still be social, competitive, and fun.
That is what makes golf so different.
Most sports separate people by age, skill, or seriousness. Golf brings people together. It gives you four hours with someone in a setting that is relaxed, competitive, and enjoyable all at once. That is rare.
I have found that golf is one of the best relationship accelerators and business development environments in the world. It is hard to find another activity that gives you that much uninterrupted time with someone while also making the experience genuinely fun.
About 90% of Fortune 500 CEOs play golf, and 80% of executives say golf helps them build new business relationships.
That tracks with what happens at the high end more broadly. Wealth research has shown that golf is the most popular sport among very high-net-worth individuals, with 18.6% either playing or watching it, more than any other sport measured. Golf also skews affluent at the participant level. National Golf Foundation research has shown that 41% of golfers report household income above $100,000.
This is not really about golf being fancy. It is about golf, placing you in an ecosystem with a disproportionate number of executives, owners, investors, and high-income people. If you are looking for a hobby that can improve your business networking opportunities, golf is hard to beat.
I did not start seriously playing golf until I was 40. I got introduced to it during COVID and fell in love with the game, but it became a real game-changer when I started connecting it to work.
From colleagues, potential investors, and LPs, to peers in my broader ecosystem, golf has meaningfully expanded my business network. Some of that has come through planned rounds. Some of it has come from meeting people organically on the course or in the clubhouse, through friends, or through friends of friends. Either way, golf has opened the door to relationships I likely would not have built otherwise.
It is rare to get four uninterrupted hours with someone. On a golf course, you do. You have time to talk, compete, laugh, and actually learn how someone thinks. That has helped me build real bonds that later turned into meaningful business relationships.
And beyond all of that, golf is just a ton of fun. That is what makes it so powerful. Usually, the things that are good for your network feel forced, and the things that are fun do not create much leverage. Golf does both.
If you have ever thought about taking it up, there is no time like the present. And for those of you in the Northeast, it is almost golf season.
Thanks for reading.
Mike Wystrach
Founder · Operator · Investor
→ Know someone who should read this? Forward it to them.
→ Follow me on LinkedIn for daily insights.
The Advantage | WiseTrack Collective
© 2026 WiseTrack Collective. All rights reserved.