Begging Leaders

Best of news this morning: we fully filled Waverly’s funding round! 🎉

It was… a journey.

So, in my typical manner, I want to overshare about the _emotional_ part of this journey.

But first a teaser. I can’t share the terms of the raise or the investor names but I can say they’re household names — at least if you have an investor or a techie in your house. More importantly, they are perfectly mission-aligned and they are the ideal partners to build a super ambitious consumer platform.

Because that’s what we’re building. A super ambitious consumer platform. Think: Elon Musk is f**ing up Twitter, someone has to stand up. That’s us.

But enough teasing… the emotional journey.

Phil Gagnon and I started on the fundraising trail in January. Right after our holiday break we met for a week in Rimouski. PhilG lives around there and it’s a great place to think (shoutouts to @LaStation). We finalized the pitch and the plan. It was not perfect. No startup ever is. But we were pumped. Let’s do this!

We “ran a process”. We collected a list of the best potential investors, tapping into our network for intros, and, most importantly, having calls after calls after calls. I’m sure it’s not unusual for many of you, but remember that I’m a product-minded math nerd. Uninterrupted Zoom calls with people all over the emotional intelligence spectrum is not exactly my thing.

To tackle this, the only tool I have in my toolbox is genuineness. I showed up to every one of these calls with my full self, pitching things I believed in, sharing our weaknesses and our uncertainties. My gamble was — and always is — that being transparent is the best way to increase my odds of finding the partner I want. The partner I will never regret for the long journey ahead.

But being genuine means being vulnerable. And being repeatedly vulnerable with people I don’t know means getting hurt sometimes. It happened. There are jerks out there in the investor world. But I’m happy to report that there are many more non-jerks than I first thought.

See, I went into many meetings with an unhealthy level of anxiety. The investors I was meeting were often huge and from their online presence I would imagine them to be harsh. I was concerned they’d consider my vulnerability as a weakness. But they repeatedly proved me wrong. I’m still puzzling this one out. How can a braggadocious investor who multiplies football and war metaphors assemble a team of people who are so good at creating a safe space?

Parenthesis. If you’re cynical you might say this is strategic. That the safe space is just a trick to get the most information out of an entrepreneur to better exploit them later. But I refuse cynicism. From the get go, I’ve decided to trust my instinct when it comes to building relationships with people. I default to trust and if you break it, shame on you.

So, investor meetings. Pitches. All day, every day, for months. Looking at my CRM today I have met 128 investors from January to April (that’s 7 bits worth of investors!). I’ve had multiple calls with more than 20% of them. I’ve had nice “no’s”. I’ve had harsh “no’s”. I’ve had ghosting. I’ve had many “we don’t lead”, “we don’t see it”, “you’re too early”, “let’s stay in touch”. It’s fine. It’s the game.

But it stacks up.

Through the darkest moments, my recurring thought was: how paradoxical.

How strange and twisted it is to be an “I’m going after Twitter!” startup entrepreneur. Every day I have to wake up and tell my (amazing!) team “Shit yeah! We’re fixing the world today!” with the kind of overconfidence that only fools should have. But for 4 months every 2 years I have to turn into a friggin’ beggar and knock on a hundred doors saying “Shit yeah! We’re fixing the world!… Can I have your money? …please?”

Sure, if we had users up the wazoo and our servers were on fire and the whole world already wanted what we built, then investors would come flocking. But that’s not where we are. And that’s never where any of the successful startups start. So we do the little dance, and we show that we’ve got the team, and the vision, and that we’re coachable, and confident, and trustworthy, and creative, and ambitious, and business-minded and…

…128 times for 120 no’s.

So, yeah. It’s paradoxical. And I’m not sure investors realize it. I’m not sure they understand just how twisted it is for the great leader they dream of finding to turn into a traveling beggar every other year. They will all say: “But without signal, what am I to do? How am I to decide where to invest?” That’s right, and I don’t have the answer for you. But if we take a couple of steps back and look at the innovation world we created, we have to realize that it has this paradox embedded at its core. Begging leaders…

Anyway, enough mulling over the journey. We closed. Watch out Elon, we’re coming for you. We’re coming with our new posse of shiny and amazing partners. Everybody else better stand back. 🙂

Thanks for granting me your attention for this long post. And thanks everyone — investors and fellow startup builders — for caring so much. I know you do. I know it’s hard for everyone. I hope an oversharing founder helps at least a little. ❤

P.-S: I have a whole other nice, emotional, and analytical post about Canadian investment in ambitious B2C. If there’s enough interest, I might find it in me to write it. 🙂