Let me take you back to the audacity of two broke 20-something founders and explain why remembering your early founder self is critical to your success today.
Little gold Corvette
OK, a weak analogy to the Prince song, but now the next lyric might be in your mind: “You gotta slow down.”
No f*#king way. The energy my co-founder and I were running on that random day in Fort Myers, Florida, was unstoppable.
It had to be: we were hustling to win a big deal against some major players and were totally outnumbered.
After nearly missing our flight (rehearsing our pitch to the last second), we got to the rent-a-car place. Problem? No cars left. We went for the cheapest option – except my partner wasn’t having it.
He haggled hard. He wasn’t joking when he said missing that meeting might mean missing rent.
They caved and gave us the last car on the lot.
Dave convinced them to give us the Corvette at the same rate as the compact car. (A very James Bond move – shout out to big energy extroverts like my co-founder!)
So, there we were, rolling up to the meeting in a Corvette, feeling like big shots.
What happened next? It changed everything.
Leave the cringe, take the lesson
As a young founder, I was always after the shiny, sexy thing. And sure, the guy we were going to see — the founder of a multi-million dollar tools company with all the toys, including a private plane — fit that bill.
His tools were top-of-the-line, state-of-the-art, and expensive as hell. There was status in owning one of his drills and also tremendous value. Those things were built to last long enough to hand down to your kids.
I’ll never forget what the tool company founder told us: his drills were great, but the consumable drill bits built his empire.
That lesson? Whether you’re selling razor blades, coffee, or drill bits — recurring revenue and customer lifetime value are the real cheat codes.
We landed the deal and celebrated in that Corvette. I thought that was the end.
That is until our new client asked us to stay longer and took us up on his plane.
Remember this when you’re flying high
We got so deep in conversation and connecting about the client’s life story that he lost his focus on flying. We approached the runway a few thousand feet higher than we should have been. At the last second, the client jerked the flight stick, and we dropped altitude FAST.
I almost threw up.
My life flashed before my eyes.
At first, I thought I was just being a wimp. But everyone else looked green, too.
Afterward, he laughed and said, “You fellas got me so deep in reflecting on my early years I almost missed the runway.”
Your story is your strategy. Don’t operate heavy machinery while telling it.
One more for the road
There’s one more piece of advice I’ve carried with me since that fateful day. It's a view that you only get after fighting tooth and nail to beat the odds and launch a successful business, like the tool king did. From 10,000 feet in the air, he turned to me and said, “Cash is king, kid.”
And it flies in from more than one place. This is a scoreboard that any business can run. If you don’t know your core metrics, you don’t know your business.
Need a set of scoreboards or dashboards for your business? (Hit reply, and I’ll send you some.)
All that from a cringey picture. See, it pays to look back and trip out on how far you've come.
If you’re like me, you use LLMs all the time. In my case, I use them as a developer, a marketer, and a business owner. In fact, I use ChatGPT and Claude for just about everything. But here’s the thing: managing your prompts can become a nightmare, fast. This is why my team and I built Promptly. Check out this Loom for more info and see how it works.
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