Ryan Hoover

I realized fundraising was the first time in my life I got rejected at scale. And honestly, as a woman, I was not emotionally trained for it. Before the feminists come for me, let me make my point. I think the first real arena where most people experience power, desire, status, and rejection is dating. And dating trains men brutally. A lot of men learn very early that if they want someone, they have to walk across the room, risk looking stupid, get rejected, survive it, and do it again. They learn that rejection is volume, timing, targeting. It’s a numbers game. A lot of women are trained very differently. Especially if you’re a pretty girl, you don’t usually walk into a bar looking at a guy thinking: “Can I have him?” You only think: “Do I want him?”. You don’t build your identity around shooting your shot 100 times and surviving 99 no’s. You don’t get trained to ask directly, get rejected publicly, and act normal 5 minutes later. You get trained to be “chosen”. To be impressive enough that the opportunity comes to you. And then you start building a company. And the whole paradigm changes. Suddenly, everyone can say no to you. Investors say no. Candidates say no. Customers say no. And when your rejection muscle is weak, your brain does the dumbest thing possible: it makes the “no” mean something about you. That you’re not smart enough. Not compelling enough. I think this is one of the most underrated gender differences in fundraising. Not that men are inherently better at it. But a lot of them have built thicker rejection scar tissue earlier. They know how to hear no and keep moving. They know how to make it less personal. They know how to treat it like volume, timing, targeting, iteration. I didn’t. I’ve raised 3 rounds. On the surface, the story looks great: I raised with Sequoia, OpenAI, Khosla. Woohoo. The real story is less sexy: every round wrecked me. I lost 5kg each time. I probably donated a few years of life expectancy to the cap table. Because every round, I only got 1 term sheet. One. EVERYONE else said no. And when almost everyone says no, your body does not care about the intellectually correct explanation. It only hears: Maybe they’re right. Maybe you’re not that compelling. Maybe you’re not the founder you thought you were. For a long time, I thought confidence meant learning not to take the no personally. I don’t believe that anymore. Maybe some people are built like that. I’m not. 30 years of being trained to be chosen does not turn into resilience because someone in a Patagonia vest says fundraising is a numbers game. So now I think confidence is something less glamorous. Confidence is taking the no very personally. Letting it ruin your day, losing your appetite, spiraling for hours… And still taking the next meeting. Confidence is just being bothered as f*** and not letting it make you smaller. I still don’t fully believe my own BS as I’m writing this, but I guess that’s the point. Can’t wait for the next round to find out.