Asking for investment money is hard. But it’s nothing compared to begging for spare change on the sidewalks of Hartford, Connecticut.
Let me explain. While I was in college, I spent one month each summer working for The Wilderness School, which took disadvantaged city kids and introduced them to the wilderness.
Most of these kids had grown up barely having stepped off the sidewalk - but we soon had them canoeing rivers, climbing cliffs, and sleeping on the ground. Thrilling yes, but the real objective was to put the kids in situations that seemed impossible, and prove to them, over and over, that they were capable of much more than they imagined.
My fellow instructors and I didn’t have much in common with the kids, so to help us understand what a shock this kind of experience could be, our two-week pre-trip training would culminate in us being blindfolded, driven to a random intersection in downtown Hartford, having our wallets and watches confiscated, and told that we’d be picked up in three days. No food, no water, no prearranged place to sleep. Just a phone number written on our arm, in case we decided to give up.
At first it didn’t seem that different from a regular afternoon in any city. But after a night sleeping on the street, and nearly 24 hours without food, I was starving. I needed money. People had it. And all I had to do was walk up to them and ask for it.
No problem. I was in clean, preppy, East Coast clothes, relatively clean-shaven, so I asked myself: How hard could it be?
Answer: very hard.
Panhandling is salesmanship at its purest. It’s the totally naked ask: money for nothing. We’re conditioned not to ask for things — and when we do ask for them, we’ve learned that we have to offer something in return. But asking for money and offering nothing back—no service, no product, not even a song—is truly terrifying.
At first, I couldn’t even ask. I would see someone coming, I’d resolve to make eye contact and ask for money, and then my body would recoil. I had climbed mountains. Rafted rivers. Run triathlons. But this was the hardest thing I had ever tried to do.
It took almost an hour, but finally I did it. A friendly-looking woman, about my mother’s age, turned the corner and walked toward me. I looked her in the eye and asked, my voice barely a whisper, “Do you have any spare change?”
“No,” she said, her face turning to stone as she walked right past me.
But I had broken the ice. Over the next four hours, I made a dollar and seventy-five cents, enough for a hot dog at the food court.
I got gradually better at asking. I learned to keep it short. To make eye contact. To slump, but not too much. To use a voice loud enough to be heard, but not loud enough to seem demanding or scary. But the breakthrough for me was simply telling people the truth. “Can you spare some change? I’m really hungry.”
There was something about speaking from the heart that cut right through. It got people’s attention and broke down their cynicism and defenses.
It’s more difficult than it sounds. It made me feel sleazy to ask. It made me feel low when people said no. But by far the most difficult thing to bear was the invisibility. Mustering up all your courage and desperation, then debasing yourself in front of a stranger, only to be totally ignored—that was worst of all.
But believe me, after that, asking an investor for $250,000 was nothing.
If you are trying to make a dream come true, there will probably come a time when you do need to put your hand out and ask for support. I can reassure that while it’s never easy, it does get easier.
And in addition to being heartfelt, there are some tried and true techniques I’ve learned from the countless time I’ve had to put my hand out and ask for the money I needed to support my latest dream.
If you’ve ever been in that situation, I think you’ll especially appreciate this week’s That Will Never Work podcast. I’m speaking with Leanne, who has an idea for a life-changing non-profit that will provide counseling to victims of sexual assault. Despite being convinced that her idea is a sound one, she’s having problems getting anyone else to support her financially. But I quickly recognize a few flaws in her approach and give her a few suggestions for things she can do that I’m confident will lead to a funding breakthrough.
I would also encourage you to read the full version of my panhandling story in my book, That Will Never Work. I go a bit deeper into making the “naked ask” which is a particularly important part of funding any early-stage venture.
As the leader of an organization, one of your two primary responsibilities is “don’t run out of money.” So regardless of what your idea is - whether you’re doing it for profit or for the good of mankind - you’re going to have to develop the critical skill of asking for money.
I’m not suggesting that you head out onto the sidewalks with your hand outstretched to learn how to be more effective. But then again, it wouldn’t hurt.