Walking Away From the Money
Within the span of a few weeks this spring, I talked to over a hundred investors, sat in interviews with some of the biggest names in startups, and had real offers on the table. I didn't take any of it.
This is the story of how that happened, starting with a pitch I completely fucked up on stage.
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Riding the high
We'd just come back from Dallas on the biggest high the company had ever been on. We had 100+ calls booked, a pipeline full of people who wanted what we were building, and a team that couldn't stop talking about when the next conference would be.
So when someone from Web Summit Vancouver reached out offering a discounted startup ticket for seven or eight hundred bucks, I didn't think twice. Fuck it, let's do it.
Signing up came with a pile of forms and optional extras. One of them was an application for PITCH, their startup competition, where a small group of companies get picked out of the entire startup cohort to pitch on stage in front of judges. I filled it out absentmindedly, the way you fill out a warranty card, and went back to real work.
A few weeks later, an email came in: we'd been selected. Out of almost 1,200 startups, only a handful get picked. Every time we mentioned it to someone at the conference, the reaction was the same: "Holy shit, you actually got in?"
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Vancouver
Four days before we were supposed to fly out, I realized I had booked the flights and completely forgotten the hotel. If you know anything about Vancouver, you know nothing there is cheap. After a lot of scrambling, we landed an Airbnb in Chinatown for three or four grand for the week. Overpriced, obviously, but it was a place to sleep and lock in.
I went in with one goal: money.
Dallas had created a good problem. We had more interest than we could handle, we were short-staffed, and everyone was running at full tilt around the clock. Up to that point, we'd been completely bootstrapped, and I'd been funding everything myself. I kept thinking about two things: how do we survive the current workload, and when it finally subsides, how do we keep the momentum instead of sliding into another lull? A couple hundred K, maybe a mil, felt like it could go hard.
And here was a conference packed with investors. So I went through the entire list of investors attending, filtered it down to anyone who invests in our space, and sent every single one of them a cold message. To my surprise, a lot of them wrote back. By the time we landed, I had twenty meetings booked with investors from Canada, the US, and overseas.
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Good money, bad money
About ten minutes into the very first meeting, I remember thinking: this is going to be a long week. It was mundane. Boring, even. And halfway through, a thought popped into my head that I didn't expect: I don't know if I want your money. You seem nice, and the money would help, but I'm not sure I could work with you.
That thought turned the whole week into something different. I'd walked in naive, thinking money is money. Very quickly, I started asking different questions. What strings come attached to this cheque? Is this person going to be active or passive? Is an angel better for us right now, or a fund? What does dilution actually look like across a seed, then a Series A, then a Series B? Can I turn giving up a chunk of my company into something massive, or am I just shooting myself in the foot?
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The anti-pitch
The strangest part of Web Summit happened after hours.
One night at a mixer, two of the guys and I were completely fried from a full day of meetings. We decided we were done working. We sat down, grabbed drinks, and just talked to people like we normally do.
Somewhere in there, we started chatting with a guy who, it turned out, was an investor. He kept asking what we did, and I kept dodging it. I'd been pitching all day and I wasn't about to do it again. Not tonight, bro.
Weirdly, that made him want it more. He started pushing: no, no, I actually want to know now. And then another investor wandered into the conversation. Then another.
It kept happening for the rest of the conference. Everywhere else, founders were chasing investors around the room, and investors were flipping their badges around so nobody could see who they were. We weren't chasing anyone. We were just hanging out, talking to other founders, having a good time. And somehow that pulled investors toward us like a magnet.
By the end of the week, we'd spoken to well over a hundred investors. Most were genuinely interested. The valuation made sense to them, the amount made sense, and a lot of them wanted to keep the conversation going the following week. Some of the best conversations weren't about our business at all. They taught me how money actually moves through a company, how dilution compounds, and why sometimes you're better off striking the right partnerships than raising at all.
I left Vancouver with more investor interest than I'd ever had, and less certainty than I walked in with.
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The pitch
Now, the pitch itself.
As CEO, the unspoken agreement on the team was that I'd be the one on stage. The problem was that I had no prep. You had to submit your deck well in advance, so one of our sales guys built it, and another wrote me a script.
Here's the thing about me and scripts: I can't do them. I talk off the cuff. That's how I sell, that's how I think. But I was buried in work, so I told myself I'd memorize it and it would be fine. I spent two days trying to get it into my head. It wasn't sticking. Five minutes before my turn, I was sitting in the audience watching other founders go, still mouthing the script to myself and praying.
Backstage, while everyone else was pacing and psyching themselves up, I was chatting with the production crew, asking how their week was going. That's just how I calm down.
Then I walked on stage.
I had the first minute memorized perfectly, and I nailed it. Then I hit the one-minute mark and my mind went completely blank. Fuck. What comes next? Fuck, fuck, fuck. I stood there frozen for what felt like thirty seconds, probably closer to fifteen or twenty, while a room full of people watched me. You could see it on their faces: what the fuck is this guy doing? I rambled through something that meant nothing and wrapped it up.
Then the judges went in. One of them tore into our business model. Our whole approach is land and expand: come in small at $700 a month, under the threshold where a company needs a buying committee to sign off, prove the value fast, then grow into multiple agents and a big account over time. I think that model is rock solid. He told me I should rethink it. In that moment, still shaken, I couldn't defend it the way I should have.
I walked off stage sure I'd completely blown it. And then people started coming up to me, including investors, saying, "Don't listen to that guy. Your model is great." One of them put it less politely than that.
Only one company from our round moved on. When the results came out, we'd been ranked second, effectively a toss-up for first, despite the freeze. The guy who beat us was from Toronto too, and he found me afterwards to say he loved what we were building and wanted to help however he could. I couldn't even be mad about it.
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Walking away
Web Summit wasn't the only thing happening that month. Around the same time, we landed interviews with YC, a16z, Techstars, and a few other top-tier programs. For a stretch of a few weeks, I was sitting across from some of the sharpest minds in the investing world.
By the end of it, the money was genuinely on the table. We had real offers.
And I decided not to take it.
That's not because I don't want to build something massive. I want this company to be worth every dollar it possibly can be. But I've watched plenty of companies get there without ever touching institutional money. They start small, stay close to their customers, grow on their own revenue, and one day you look up and they're worth hundreds of millions of dollars. Nobody wrote a TechCrunch article about their seed round, because there never was one. That path makes a lot more sense to me than the unicorn playbook.
The venture path has you optimizing for the next round: the next valuation bump, the next milestone that makes the story sound good to investors. I'd rather put every ounce of my focus into the people actually using what we build. I want to solve their problems so well that they can't imagine going back, and build something I'm genuinely proud of that actually moves the needle for them. If we do that right, the valuation takes care of itself.
We've been bootstrapped from day one. I've spent a fuck ton of my own money getting here, and I still have a fuck ton to keep going. So the question was never whether we could survive without investment. It was whether investment would make us better, and when I was honest with myself, the answer was no. Not right now. Not at the cost of control over where this thing goes.
So I'm betting on us. My money, my call, my full attention on the customers. If I'm going to scale this, I'm going to do it on our terms.
I went to Vancouver looking for money. I came home realizing I'd rather bet on myself.