I’ve spent my life in rooms where the stakes are high and the egos are higher. What keeps me steady is a simple rule I learned on a skateboard: progress is a contact sport. My view is clear. If you want real growth in business, investing, or real estate, you must learn how to fall and get back up—again and again. This matters now because wins are scarce, noise is loud, and attention spans are short. Reps with failure are the unfair edge.
The lesson a skateboard never lets you forget
Skateboarding is one of those things you never get the trick first try.
That line isn’t about boards. It’s about identity. The park teaches what classrooms often skip: repetition under pressure. Falling isn’t a flaw; it’s feedback.
If you can fall on your skateboard 40, 50 times in a row and then finally land that trick and roll away, I mean, that’s like one of the best feelings.
I’ve felt that same rush closing a deal on the fifth pitch after four hard no’s. I’ve felt it when a property finally cash-flowed after months of fixes that didn’t stick. Those moments pay out because the falls trained me to stay calm and adjust.
That’s one big thing that skateboarding has taught me is how to fall and then get back up.
That line guides how I coach founders, structure deals, and review setbacks. It’s not bravado. It’s process.
How I use “falling well” in business and investing
My rule: fall fast, learn fast, move fast. I don’t worship failure; I study it. The first version of a pitch is a test. The first offer on a property is a probe. The first model for an investment is a draft. When it “falls,” I adjust one variable, not ten. Then I run the rep again.
Here’s the short playbook I run daily. Use it and you’ll turn stumbles into speed.
- Set one clear trick: define the next small win, not the perfect win.
- Limit variables: change one thing per rep so you know what worked.
- Log the fall: write the miss in one line and the lesson in one line.
- Shorten the cycle: shrink the time between attempts.
- Protect the body: in business, that means cash, calendar, and mental health.
Skaters wear pads for a reason. In business, my pads are reserves, honest calendars, and mentors who tell me the truth. That safety lets me take smarter risks and keep trying.
But isn’t failure wasteful?
I hear it often: “Failure costs too much.” What costs more is avoiding the reps that teach you where the real edge is. The market punishes guesswork. Reps reduce guesswork. Even small sample sizes beat blind hope.
Another pushback: “Some people can’t take that much rejection.” I get it. Volume matters, but so does design. Don’t aim for pain; aim for fast feedback. Short loops carry less emotional weight and more useful data.
The hidden upside of 40 or 50 falls
Every fall builds timing, pattern recognition, and emotional range. You start to feel when to step off a bad deal early, or when a tough moment is just a wobble before the landing. Confidence isn’t noise in your head. It’s evidence in your history.
In my coaching and deal work, the people who win aren’t the ones who avoid falling. They are the ones who can fall without losing their focus or their values.
The stance I’m taking
We need a culture shift: praise clean landings, but reward the reps that made them possible. Track attempts with the same pride you track wins. Put “falls” on the scoreboard, then cut the time between them. That is how you build durable success in markets that don’t care about your feelings.
Here’s the challenge I’ll leave you with. Pick one “trick” for this week—a sales script, a capital raise ask, a rehab plan. Run 20 clean reps. Log each fall in one line. Adjust one variable at a time. By Friday, ship the improved version. Then do it again next week. You’ll feel the roll-away.
Frequently Asked Questions
Q: How do I know which goal to treat as my “trick” first?
Pick the smallest target that moves real results: one qualified meeting, one revised offer, or one property walk-through. Make the win obvious and measurable.
Q: What if repeated tries drain my motivation?
Shorten the loop. Reduce the time between attempts and track tiny gains. Momentum creates energy, and small wins feed the next try.
Q: How many “falls” are too many before I pivot?
Set a cap up front—say 15 reps. If results don’t improve, change one major variable or switch the goal. Don’t wander; decide.
Q: How do I protect cash while taking more swings?
Use guardrails: fixed test budgets, time-boxed experiments, and clear stop-loss rules. Safety lets you learn without risking the core.
Q: How can a team adopt this without burning out?
Make attempts visible and short, rotate who leads reps, and review lessons in five-minute huddles. Celebrate learning speed, not just outcomes.
