Meeting Todd on the beach: luck in fundraising

What does a lobster bathing suit have to do with fundraising or building a company? More than you'd think.

Many years ago, my wife and I had a trip booked to the Bahamas. Three days before we were supposed to leave, she realized her passport was expired. Being a Miami native, and with the Bahamas being so close, she had forgotten one small detail: you still need a passport. Not her finest moment.

Being the saint she is, she rebooked the entire trip in two days. New flights. New hotel. New destination. The Virgin Islands. No passport needed.

When we got to the hotel, we went to the beach and the pool. I was wearing my 🦞 lobster bathing suit. Stylish, I know. And Todd noticed it. (Let's be honest though, who wouldn't? 😂)

Todd is genuinely one of the nicest humans you will ever meet. He may have connected with me regardless of the swimsuit, but the swimsuit created the opening.

He asked if I was from Boston. He had a connection to the area. We got to talking. Eventually he asked what I did for work.

I told him about Perch. He asked if we were fundraising. We were.

A couple days later, Todd committed to our active round.

For a long time, I treated that as a funny fundraising story. And it is. But the further I get from Perch, the more I realize the whole company was full of moments like that. Not always that absurd. Not always involving crustacean-themed swimwear 🦞 But the same basic pattern.

A random conversation became an investor. An article reached the right person at exactly the right time. Responding to the right inbound request turned into an impactful employee. A small decision created a collision we never could have planned.

That is the part of company and life building we do not talk about enough.

We like the clean version: build a great product, tell a great story, hire good people, work harder than everyone else, win.

And yes, all of that matters. Todd would not have invested if there was no company worth investing in. The pitch mattered. The story mattered. The work mattered.

But if my wife had renewed her passport on time, we would have gone to the Bahamas. If she had booked a different hotel, I would not have met Todd. If I had worn a different bathing suit, maybe he never would have started the conversation.

That is uncomfortable because it means some of the most important moments in a company's life or even your life are not fully under your control.

But that does not mean you are powerless. The best founders I know increase their surface area for luck. They meet more people. They tell the story more often. They stay curious. They follow up. They create more collisions.

They put themselves in enough rooms, enough conversations, and enough weird beachside moments (especially these) that luck has more chances to find them.

Looking back, Perch was not built by luck alone. But it certainly was not built without it.

The work is making the most of the luck you get.