Chapter 35

1K 89 1

"David," said Andrea with a warm smile and open arms. "It has been far too long. You're looking good. How has life been treating you?"

"Okay, I guess."

David hugged Andrea halfheartedly.

"That good, huh?"

David sat down and made himself comfortable in one of Andrea's blue swiveling chairs. He swiveled it back and forth. Andrea looked at David intently with her soft grey eyes. David was always impressed with how radiant and vibrant Andrea looked. He noticed that she had cut her blonde hair, which settled well with her face.

"Well, let's see. I was kidnapped and interrogated by the Secret Service, my girlfriend broke up with me, I made a fool of myself in front of eight million people on national TV—"

"Yeah, I saw that. It wasn't that bad. Many people never get exposed to millions of viewers like you did."

"Thanks for saying so, but yes, it was that bad. I had an acquisition offer rescinded, my cofounder quit and took a day job with you, and I was nearly evicted from my apartment."

"Nearly? How'd you get out of that mess?"

"I found an ad behind my couch for the auction website I used to buy the jellyfish website in the first place. In the excitement of Cryptobit, I forgot that I even owned the thing. I put it up for sale in a quick auction. I got a quarter for every dollar I originally spent, but that was enough quarters to pay rent for a couple more months."

"David, can I ask you a question?" Andrea said as she leaned back in her chair.

"Sure."

Andrea looked directly into David's eyes. "When are you going to forgive yourself?"

"What do you mean?"

"Terrible things have happened to you. Clearly. You can't choose the cards you're dealt in life. Sure you have been dealt some pretty crummy ones recently, but how you react to life is always in your control."

Andrea paused as the words sank into David's consciousness.

"These things that have happened to you are not your fault. But you're carrying them around like a ball of pain. You carry it with you and flog yourself with your misfortune. And you flog those around you. Your girlfriend, maybe? So again, I ask, when are you going to forgive yourself?"

David fidgeted in his seat. He felt something deep inside his belly like a cannonball coming up to his throat. He tried to respond, tried to say something, anything, but the words wouldn't come.

Andrea continued: "These things didn't happen to you because you weren't good enough. They didn't happen to you because you are failing at being an entrepreneur. These things happened to you precisely because you are succeeding at being an entrepreneur."

"It doesn't feel like that," David managed to muster.

"I know it doesn't. This is life, though. This is how it works. Let me tell you a story. I know you might not believe it on first glance, but I've been around the block a few times. This is not my first rodeo. The startup I did right before MochaToca started out as a huge success. We had created an analytics company right as online advertising started to take off. For years, it felt like we could do no wrong. It was the fastest growth I had ever experienced or seen in my career, even faster than MochaToca.

"We raised twenty million dollars over four years and hired a hundred and fifty people. We made millions of dollars, but we were hiring ahead of revenue and running out of cash quickly. I had almost finished putting together our next round of financing when...we...when life happened. One of our founders was sued for sexual harassment a few days before the investment was set to close. Then our biggest customer dropped us without notice. The investment fell apart and I went to the bank to get a loan, but we were spending so much and had so little left that the banks wouldn't lend us a dime. I went back to our investors who got cold feet. With no other options, I had to fire most of the staff, which of course stalled our growth. This led to a death spiral and within a month, we shut down the company. I was devastated. For months it ruined me. I bought a one-way ticket to Hawaii and just sat on the beach for six months trying to figure out what I did wrong. Do you know what I learned on that beach?"

"Never trust investors?" David asked tentatively and with a slight smile.

"Dear goodness, no. If I were in their shoes, I would have made the same decisions. No, what I learned is that when they say nine out of ten startups fail, they're not just talking about the bad ones. It's equal parts luck and preparation, and all I can do is bring my best every day. I stopped taking it all so personally. There was nothing I could have done differently. It was like a sudden wave that came out of nowhere and ripped my ship in half. A wave isn't good or bad. It doesn't care, it has no motives. It's just a wave. Mother Nature. I just happened to be in the way. And I projected the darkest parts of me to that wave. I blamed the world for what was inside of me. For the ball of hurt I was carrying around."

Andrea paused.

"David, it's not the startup troubles that are making you feel this way. Who made you feel not good enough? When did that happen to you? You know it's not your fault, right?"

David looked up. His eyes filled with immense pressure.

The Term Sheet | Wattys 2016 WinnerRead this story for FREE!