Kobe Bryant. Five-Time NBA Champion. Sure-fire first-ballot NBA Hall of Famer. Venture capitalist. And now the first former NBA player to receive an Oscar nomination for his short film Dear Basketball.

If you're like me, you might be wondering, "What? Oscar nomination? He just became a  venture capitalist."

As a longtime NBA fan, I've followed Bryant's career ever since he entered the league. As an 18-year-old rookie, Bryant dazzled the league with his high-flying dunks, often against opponents twice his age.

After a legendary career, Bryant went out in Bryant-like fashion, shocking the sports world by scoring 60 points in his last game. Then, just two months into retirement, he shocked the non-sports world by announcing the launch of his $100 million venture capital firm.

And earlier this week, Bryant received an Oscar nomination.

Who is this guy? The 21st-century Leonardo Da Vinci? (After all, Bryant does speak fluent Italian, having spent his youth in Italy.)

The short answer is no.

Never be afraid to ask for help.

In an interview with Jimmy Fallon in April of 2017, months before we knew Bryant's short film had any chance at an Oscar nomination, Bryant confesses how he convinced veteran animator Glen Kleane and legendary composer John Williams to join his project just by asking.


When Fallon asks how Bryant knew John Williams, Bryant's response is pure gold:

"Well, I reached out to John years ago because I just wanted to talk to him about how he composed, because I believed there was some connection between how he orchestrates and how I conduct a basketball game and putting guys in the right position..."

Fallon then asks in a surprised tone if Bryant regularly cold calls people for advice. Bryant confidently admits that's what he does. He then emphasizes: "The best way to learn is to reach out and ask."

The last sentence speaks volumes. All you really have to do is ask.

In an interview in 1994, shortly after Steve Jobs had returned to Apple, Jobs emphasizes the remarkable power of asking. Says Jobs: "I've never found anybody who didn't want to help me when I've asked them for help."

Always be asking.

Time and time, as an entrepreneur, I've found the most successful way of getting advice or assistance was just asking. The worst thing that could happen to you is someone says no.

Want to fundraise? Ask. Need a co-founder? Ask. Need a customer? Ask. The hardest part is the fear of rejection. However, after a while, the fear of rejection will become smaller and smaller until it eventually disappears. If the fear of rejection is the only downside of asking, why not ask more often?

When I was recruiting for my first technical co-founder for my startup, I would walk around college campuses and approach anyone who looked like a coder. My goal was to build a minimal version of our product to show potential customers. If the person I approached had a big backpack and/or big glasses, I assumed he could possibly code. 

At first, I felt extremely awkward. Especially because I didn't know how to code and I didn't attend the schools I was recruiting at. However, after getting rejected so many times, approaching people and asking them to join my startup became easy. Surprisingly, within two weeks, I was able to recruit my first technical co-founder, who was able to help us with our beta launch. 

A few years down the line, we raised $4.6 million and built the company to a $15 million dollar valuation. If I had stopped asking before we launched, we would never have had the success we achieved. 

Go ahead. Want something? Take a page from Kobe Bryant or Steve Jobs and just ask for it. You might be just one question away from building that company you always dreamed of, or in Kobe's case, receiving an Oscar nomination.