Make All the Asks

“I didn’t want to bother you.”

“I didn’t want to impose.”

“I didn’t want to show up with my hand out.”

“I feel like if you were interested, you would have said something already.”

“I wasn’t sure if it was ok to ask.”

“I haven’t spoken to that person in a while—it might be too random now.”

Do any of these lines sound familiar? Too often, I meet founders that need something, and feel awkward about asking for it for a variety of reasons. Disproportionately, the ones who hesitate to make the ask are women or people of color—at least in my experience.

Speaking from a position where I often get asked a lot, what I don’t think people realize is what the other half of the exchange is in an ask. If a startup pitches me, for example, they’re not asking—they’re selling their equity. That’s a fair tradeoff (at least, if they don’t think it is, they probably shouldn’t have quit their job to start this company.) If no one ever pitches me, then I’ll have no companies to invest.

And if I know the person, I’d so much rather get a pitch from them than someone I have to get to know from scratch (although I’m happy to take cold pitches anytime, too!).

Pitches, while asks for the founder, are potential opportunities for me. Even if I don’t find the company, it’s an opportunity for me to learn about a new space, or just to be helpful enough where you might recommend a founder come and pitch me later on—and maybe that founder is the next big thing.

Most people like feeling helpful—it makes them feel less alone and more useful to others. An ask is really an offer of purpose to someone else.

“Here’s something you can do to help me,” can be a welcome interpretation of an ask if someone is feeling low on self-worth.

You should never be scared to ask for something you need—because the worst thing that can happen is that someone says no. Anyone who dings you just for making an ask, saying perhaps that you’re too needy, probably was never really going to help you with much of anything anyway, and probably doesn’t add much value to your life.

No person is an island—and getting ahead means getting help from others. An ask is a very simple way to direct those who are interested how they can help—because you probably have a lot of people in your life who would help you, but aren’t sure what you need.

I wouldn’t have gotten my first job in venture capital had I not asked to extend my internship part-time past its original deadline. I wouldn’t have gotten that internship if I hadn’t asked if there were other opportunities after interviewing for a few that I didn’t love.

And if you’re ever concerned about making too many asks, you can ask just one more—ask how you can help someone that you’ve asked for help from.