Learn from Rejection

In high school, I ran for sophomore, junior, and senior class president. I lost all three times. Based on this track record, it was obvious I should run for student body president. I did, and I (wait for it) lost. I was also cut from the baseball and basketball teams. I remember my mom and I going to Junior’s Deli on Sepulveda to celebrate my admittance to UCLA after initially being rejected.

Arriving on campus, I rushed five different fraternities and got admitted to one, as they were looking to fill a room in the house with someone who’d help pay the dues. When I graduated, I interviewed at twenty-two firms and got one offer, from Morgan Stanley.

I applied to several MBA programs and was rejected by Stanford, Indiana, Wharton, Duke, UT Austin, and Kellogg. I was admitted by UCLA and Berkeley Haas with the same narrative I pitched to UCLA the first time: “I’m an unremarkable kid, but I’m your [California’s] unremarkable kid.”

In business school, I ran for class president, and lost. Since graduating from business school, I have started nine businesses. Most have failed.

Serendipity Is a Function of Courage

I enjoy alcohol, but it’s also served a useful evolutionary purpose, as it’s dramatically increased my pool of potential mates. In social situations, “alcamahol” has been Kevlar against rejection. I’m a better version of myself after a couple of drinks: funnier, more affectionate, confident, engaged, nicer … better. (Can’t wait for the judge-mail on this one.) I remember being at the pool at the Raleigh Hotel in Miami Beach and seeing a woman I was incredibly drawn to. I committed myself to speaking to her before I left, and immediately (not proud of this) ordered a drink. Asking a VC for money is nothing compared to approaching a woman midday in a beach chair, sitting with another woman and a guy, and opening. I tell my students that nothing wonderful, I’m talking really fantastic, will happen without taking a risk and subjecting yourself to rejection. Serendipity is a function of courage.

My willingness to endure rejection from universities, peers, investors, and women has been hugely rewarding. Knowing what you want is a blessing, and fear of rejection is a bigger obstacle than lack of talent or the market. Train yourself to take some sort of risk (ask for a raise, introduce yourself around at a party) every day and get comfortable grasping beyond your reach.

My oldest son’s middle name is Raleigh.