Welcome to the Week: Do I Look Like a Stock Picker?
David Osterweil
Founder & CEO @ Fitlife Foods | Strategic Entrepreneur | VC, Private Equity & EOS Visionary
Once a week, I take my son to soccer practice—7:30 to 9:00 PM, 30 minutes away. It’s a long night. I don’t love it (as I prefer to be in bed by 9), but I do love the car time. The best conversations happen when there are no distractions, just the road, a kid in the passenger seat, and whatever topic surfaces.
During practice, I set up shop in a nearby Publix Super Markets to catch up on work in the break area. Nothing out of the ordinary—just me, my laptop, a bottle of water, and 90 minutes of focused time. But then, out of nowhere, a Publix employee walks up and asks:
“Hey man, you look like you make some investments. What stock would you buy?”
Strange question.
But here’s the stranger part—this was the third time in the last 6 months that a random person had asked me the exact same thing. First, it was someone on my home renovation crew. Then, another guy making a delivery. By the third time, I literally looked over my shoulder, half-expecting to see a sign taped to my back: “Ask me about my stock picks!”
Now, besides the fact that I would never make a recommendation on an individual stock, I gave all three people the same answer:
“Invest in the S&P 500. Put a little in every month. Pay attention to the 8th wonder of the world—compounding.”
But after the third time, I had to pause and ask myself:
Why do people keep asking me this?
And after deep reflection, I landed on the most profound answer I could muster:
I have absolutely no idea.
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Maybe I give off “finance guy at Publix” vibes. Maybe it’s because I tend to look up and make eye contact rather than stare at my phone. Or maybe it’s just a reminder that people—especially total strangers—are always looking for clarity, an edge, a way forward.
Which, in a way, is what we’re all doing.
We seek wisdom from books, mentors, or even random Publix customers who just look like they might know something. We want the simple, straight answer to a complex problem. But success—whether in investing, business, or life—isn’t about one hot tip. It’s about showing up, making small, smart choices consistently, and trusting the power of time.
So, as you head into the week, ask yourself:
Because whether it’s money, learning, or life experience—small, steady investments always add up.
Now excuse me while I go check my back for any more mysterious signs.
Go Feed Your Journey,
David
P.S. I have one other philosophy with investing (that I did not share with those who asked me randomly for a hot tip) which is buy something only if you are willing to hold it for 10 years. That was borrowed from Warren Buffet.