Today I had a great chat with founder friends about being unapologetic about asking for opportunities, even if the requests are somewhat outlandish. If someone is going somewhere you want to be, ask if you can join them. If someone is working on a project you want to learn about, ask if you can work on it too. If someone knows a person you’d like to meet, ask if they’ll give you an intro.
Some people might call it being pushy or overstepping. I disagree. I think it’s the sign of a hustler. Hustlers get opportunities others don’t. One of many reasons for this is that they ask when others won’t. Of course, you should be respectful in how you ask. But I don’t see anything wrong with making the ask. The worst that could happen is they’ll say no. In fact, people will say no most of the time, and that’s OK. But the one time someone says yes, it could change your trajectory. Sometimes it’s as simple as they like the fact that you asked when others didn’t—they like the hustle and reward you with an unexpected yes.
As one friend put it, “The answer is no to 100% of the questions you never ask.”
Hearing no doesn’t really bother me. When I was an early founder, I was aggressive about asking for opportunities because I had to be. Over the years, I’ve lost a little of that edge. Today was a reminder that I need to get it back and be unapologetic about asking for opportunities.