Something clicked for me in the middle of all this fundraising chaos that I can't stop thinking about.
A lot of the advice I've been getting comes from founders who have already raised. Which makes sense, they should know best, right? A lot of those founders happen to be men. That is inherently not a problem, and I'm genuinely grateful to every single one of them for their time and their willingness to speak at me. I mean, with me.
But here's what I noticed: when we'd get to what I consider the hardest part, the actual ask, the close, the "so will you write the check" moment, they'd kind of... brush past it. Like it was obvious. Like of course you just ask. What's the big deal?
And I realized: for them, it kind of isn't.
Here's my theory as to why. Men have been training this exact muscle since puberty. Shooting your shot (in dating, in rooms they have no business being in, on job applications they're laughably underqualified for) is a numbers game they've been playing their whole lives. Women have largely been socialized to do the opposite. To wait to be asked. To be selective, deliberate, considered. To only put ourselves out there when we're pretty sure the answer is yes.
Don't believe me? Look at the data. Men swipe right on almost everyone and let the matches sort it out. Women deliberate and curate. Men apply to jobs when they meet 30% of the criteria. Women wait until they're at 80%. Men are simply getting more reps and they now have no hesitation.
The result of all this is that men have years of embodied muscle memory around the ask. Any sting of rejection or second thought was beaten out of them by that 3rd middle school slow dance. For a lot of us, it hasn't. We've been too busy being excellent (if I do say so myself) and waiting to be discovered. (But baby, as much as no one is coming to save you, you don’t get what you don’t ask for).
I told a friend about this theory and she said something that stopped me cold. She gets devastated by the two rejections she gets a year. Two total. Not two per month. Two. And I don't say that to make fun. I say it because I get it completely, and also because I wonder: what if the devastation isn't about the rejections themselves? What if it's about never having built the muscle to sustain the sting?
Because here's what I think is actually true: rejection doesn't get less real, it just gets less loud. The nos stop feeling like verdicts and start feeling like data. Like you're statistically doing it right. Someone much wiser than me said: If you're only asking for things you get, you're not aiming high enough. There must be a proven number of nos we get in a year to know we are absolutely optimizing all things in life. If you only get told yes you never progress. (BRB emailing my stats professor to see if there's a proven rejection quota-stay tuned).
So how do we get reps? That's what I keep asking myself. Do I say hey to every shirtless man on the Austin riverfront? (I'd probably just end up stopping to ask about all their dogs names in baby voice, so prob not that.) Do I swipe right on everyone? What is the business equivalent of swiping right on everyone?
I'm still figuring out the exact prescription, but here's what I know: the ask is a learned skill. And the only way to learn it is to do it badly, repeatedly, until it becomes muscle memory. Until the nos stop stinging and start counting. So let’s channel some BIG ASK ENERGY.
Your challenge this week: Make one ask you've been putting off because you're not sure the answer is yes. A pitch. A raise. Reach out to someone “out of your league”. Whatever your version of shooting your shot is, take it!
Then hit reply and tell me what happened.
Stay unscripted my loves 🖤 - EmmyLu