In a conversation yesterday with a local entrepreneur about a year into his second startup, we both had a story to tell about how we didn’t think there was any way possible to get what we wanted in a certain situation. The two situations were remarkably similar.

There’s No Way They’ll Say Yes

His: we had been working with this very talented individual on contract for several months, and we really wanted to hire him full-time. But, he already had a six-figure full time job and we were really his side hustle. Why would this very talented, very successful 27-year-old want to come work for us. But we decided we had nothing to lose, and we approached him. He said he’d love to join us, and that he wasn’t really happy with his other full time gig.

Mine: we were a completely broke startup. We literally had no money. The two co-founders had put $250 each into a bank account. But we really needed a solid web developer. My friend and former co-worker fit the bill exactly, but there was no way he was going to come work for a broke startup for free, right? We asked anyway. His response? “Sure! I work 50 hours a week, but I’m single and have another 50 hours a week to try something new!”

Always Ask for What You Need

Every week at Pitch Practice, we teach the final point in the elevator pitch: “the ask”. As a startup founder or entrepreneur, you always need something: advisor, mentor, investor, co-founder, loan, investment, introduction, beta user, employee…the list could go on forever. Ask for what you need. Even – or especially – if you think there’s absolutely no chance of a “yes”, ask anyway. You have nothing to lose. You don’t know the entire situation of the person or organization you are asking, so ask anyway.

Remember that really pretty girl or nice looking guy in High School who never had a date? Yeah, the one who finally confessed at your reunion that they had a huge crush on you all through high school. You didn’t ask then, did you? Ask now. If you don’t ask, you will never know.

 

What do you think?