Mistakes I’ve Made
Lessons Learned the Hard Way in Investing, Business, and Life
I’ve spent a lot of time trying to get everything right. I stared at spreadsheets, obsessed over the math, and worried about how decisions might look to others. Over time, I learned you cannot figure everything out from a screen or a book. The best lessons I have learned came from doing something, realizing it was not what I wanted, and being forced to change course.
The truth is, nobody bats 1,000. Not in business, not in investing, and definitely not in life. We all have things we’d like to do over, but that’s part of the journey.
I’ve found that the most important moves I’ve made weren’t the ones that looked perfect on paper, but the ones where I had to figure it out as I went. They came from getting things wrong first. From doing something, sitting with it, and realizing I would do it differently next time.
I’m sharing these mistakes I've made because I’ve realized that the cost of waiting for the “perfect” moment is almost always higher than the cost of making a mistake and moving forward. Whether it’s a stock I sold too early or a business strategy that didn’t pan out, these are the insights I’ve gained from simply staying in the game.
It’s not about perfection, it’s about progress. Every misstep, every second-guess, every decision that didn’t go as planned is just another step forward. What matters isn’t that you never fail, but that you keep moving, learning, and building conviction along the way.
Here is what I’ve learned from the times I got it wrong and what I’m doing differently now.
Business Lessons
Find Your Niche: You cannot be everything to everyone. Trying to serve every single person who walks through the door is a recipe for burnout. When you find your niche, you find your value. Finding a niche changed everything. Not everyone is a fit and that is normal.
The Advertising Donation: I spent years putting money into advertising just because I felt like I was supposed to. It didn't bring in business. It just felt like I was donating to the advertising and media companies. If an ad isn't moving the needle, stop doing it.
The Billboard Exception: I did not recognize what actually worked soon enough.
Billboards ended up being the best advertising investment I have made. In a digital world, sometimes the most physical and old school presence is what actually sticks. It’s the one form of advertising that I have always done and still do to this day.
It’s Okay Not to Fit: I used to take it personally if a client wasn't a match for my business. Now I realize it’s normal. Not everyone is a fit for you, and that’s perfectly fine.
Focus on Clients, Not Competition: I wasted too much energy looking at what the guy down the street was doing. Focus on your clients, not the competition. Your clients, not your competitors, drive your success so keep your attention where it matters.
Surround Yourself with Strengths: One of my earliest mistakes was trying to do everything myself. I was reluctant to ask for help. Delegation didn’t exist in my world. Now, I focus on finding people whose strengths are my weaknesses and letting them do what they do best. I’ve realized I’m not an expert at everything I thought I was.
Investing Lessons
Selling for No Real Reason: One of my biggest mistakes was selling a stock simply because it was up, even though nothing about the business had changed. If the reason you bought it is still true, don’t let fear, market noise, or boredom push you out of a winner. Let your best positions run.
Double Down on Winners: We’re often conditioned to think that if a stock is rising, we’ve missed it, or that it’s time to sell. The opposite is usually true. Nothing is more bullish than all-time highs. They signal that a company is winning. If a stock you own is performing well, don’t be afraid to add to it. Success is a signal, and rising stocks often attract even more buyers.
Cut Your Losses: One of the hardest lessons I've learned is knowing when to let go. If a position isn't working and your original thesis no longer holds, don't hang on out of pride or hope. Hope is not an investment strategy. Protecting your capital is just as important as letting your winners run. Remember: it takes a 100% gain just to recover from a 50% loss. Cut the cord and move on.
The Waiting for a Dip Trap: I’ve waited too long to buy stocks I loved because I thought, "Surely it can fall a little further." Usually, it doesn’t. You end up with buyer's remorse because you missed the move entirely. Trust your conviction and buy.
Just Buy: When the stock market falls, your instinct is to wait for the dust to settle. But looking back, buying during the sell-offs has always been the best move.
Paying Off a Vehicle: When I was younger, I paid off my truck because it looked smart on paper. A few months later, I bought a new one. I like new vehicles. Leasing has made far more sense for how I actually live, and I’ve done it ever since. Do what you enjoy, not what others think you should do.
Life Lessons
Caring What Others Thought: This was my biggest waste of energy. I used to worry about how my choices looked to people who weren't even living the life I wanted. The truth? Nobody cares as much as you think they do. Do what’s right for you.
The Cost of Waiting is Real: Whether it’s traveling, building a home, or starting a renovation, waiting will almost always cost you more money. Materials go up, labor goes up, and time disappears. If you have the means, do it now.
Helping Others: I did not help others soon enough. Sharing what you know can change someone’s life. Business, investing, or otherwise. It’s why I started to gift my book as much as I have. Make sure you give back.
Life is a Series of Routines: We are what we do every day. If your routine is nothing but stress and spreadsheets, that’s what your life will be. So build good ones.
Work to Live, Don’t Live to Work: We all have to grind sometimes, but don’t let the grind become your identity. Work is the engine that funds the life you want to lead, not the other way around.
The U-Haul Principle: You’ve heard it before, there’s no U-Haul behind a hearse. You don’t want to be the richest man in the graveyard. Use your investments to fund a life you actually enjoy today, not just a number for a future you might not see.
Spreadsheets Don’t Capture Everything: You have to do what you want to do, not just what looks mathematically optimal on a spreadsheet. Sometimes the “right” move for your life doesn’t fit into a cell in Excel. Not everything fits on a spreadsheet. You do what works for you, not what looks right to others. Who cares.
Nobody is perfect.
You learn as you grow and you grow by doing.
Create joy.
Make memories.
A legacy is built while living, not after.
Have fun.
Enjoy the ride, my friend.
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