What Two Bums Taught Me About Pitching

For years, Kelly and I walked past the same guy on the same block. We called him Gotta Dollar 1.

He laid on a planter on the side of the sidewalk — not sitting, laying — with the energy of someone who had decided long ago that the world owed him something and was furious it hadn't paid up. Surly doesn't quite cover it. This guy radiated a specific kind of hostility that made you want to cross the street, which was unusual in sunny downtown West Palm Beach.

His pitch was exactly one word. Dollar. Sometimes framed as a question. "Gotta dollar?" But here's the thing — and this is the part that always got me — he'd wait until you had already walked five or ten feet past him. You were already gone. Mentally, physically, emotionally gone. And then, from behind you, in a tone that suggested you had personally wronged him: Gotta dollar.

No eye contact before the ask. No setup. No warmth. The request came after you'd already escaped, delivered with enough contempt that turning around would have felt like a defeat.

We walked past Gotta Dollar 1 for years. Never gave him a cent. Never made eye contact. Never even slowed down.

Then one day, on another sidewalk downtown, we met a completely different guy.

We never got his name. We just called him Sane Friendly Sympathetic Bum, which, in the taxonomy of street characters, is actually high praise. He was clearly homeless. Probably had some version of the drug or alcohol situation you'd expect. But he was on. He talked about the weather. He held the door. He had this energy — hard to describe — like he'd made some kind of peace with where he was and had decided that today was going to be a good day regardless.

He didn't ask for anything in a way that made you feel cornered. He just existed in the world like a person who was glad to be in it. And what happened was strange: you actually wanted to give him something. Not out of guilt. Not out of obligation. But because the interaction left you feeling better than before it happened.

He was a net positive. A genuinely rare thing on a crowded sidewalk.

We only saw him for a few days. Then he was gone.

I like to think his attitude got him out. That somebody hired him, or he kicked whatever he was fighting, or he started something of his own. Wherever he ended up, I'd bet my money his outlook followed him there and served him well — and served everyone around him well too.

Gotta Dollar 1 is also gone. Been gone a while now. I don't have the same optimistic theory about where he ended up.

Here's what I think about when I think about these two guys.

Every single one of us is making an ask, all the time. Investors pitching LPs. Founders pitching investors. Sales guys pitching clients. People in relationships, in businesses, in negotiations of every shape and size — everyone wants something from someone.

And the difference between Gotta Dollar 1 and Sane Friendly Sympathetic Bum is not circumstance. It's not luck. It's not even talent.

It's whether you add value to the interaction before you make the ask.

Gotta Dollar 1's entire strategy was to demand, from behind, with contempt, and hope guilt did the rest. It never worked. Not once in all the years I watched him run the play.

Sane Friendly Sympathetic Bum just showed up as a decent human being and let the rest take care of itself.

The ask almost becomes irrelevant at that point. When someone makes you feel good just being around them — when they hold the door, when they're genuinely warm, when the encounter leaves you better than it found you — you want to give them what they need. You want to see them win.

Nobody wants to turn around for the guy yelling at their back.