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Taking the Start-Up Plunge: Can You Handle the Red Pill?

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Alamy
Alamy

I shot upright in bed in the middle of the night, my heart pounding in my chest, the sheets drenched in sweat. I had narrowly avoided a terrorist bombing, I'd made it through the Marine Corps' toughest school, and I'd fallen through the ice into the Arctic Ocean in the middle of winter. But this was the first time in my life I had been shocked awake by a panic attack.

Before the venture capital offers, before the New York Times and Wall Street Journal articles, before the dozen employees and the hundreds of new customers each week, all we had at Plated.com was an idea. And no matter how much my co-founder Josh and I believed, everyone else at the time thought our idea sucked.

"What do you guys know about food?"

"Who has the deep logistical expertise?"

"Who's writing your first check?"

"Why are you doing this?"

I had been married less than a year, and I'd left a cushy job on Wall Street to pursue something where I thought I could have an impact, where I thought I could have fun, and where I thought I could build something that mattered. Josh and I wanted to use the cutting edge of the consumer web to help people reconnect with cooking. We had done our homework, and we knew there were millions of Americans who wanted to cook, but currently it was just too damn inconvenient, expensive and hard.

Late last spring, we took the plunge. We had met at Harvard Business School back in 2008, and now we were officially co-founders. Over the next few months, we burned through our personal savings and put over $40,000 on our personal credit cards as we sprinted to prove that our idea had legs. We bought groceries and packed them in boxes at my apartment on West 14th Street, hauling boxes of salmon and basil down to FedEx in sweltering 95-degree heat.

My parents thought their first born Jewish son had officially lost it. My wife was on the brink of running away. And our friends who were kind enough to be our guinea pigs rarely re-ordered. We had spent almost $20,000 of our own money attempting to build a cold packing space inside of the old Guinness bottling factory in Queens. Using Josh's engineering degree, we planned a system where we could save cash by using six industrial air conditioners instead of buying a proper walk-in refrigerator. After two weeks of building and thousands of dollars of expenses, when we turned on the system, the room wouldn't get below 75 degrees. Our idea was failing.

It was the most stressful and frightening time of my life. I had liquidated my IRA and 401(k) accounts, my credit limits were maxed out, and I had less than $1,000 in the bank. I couldn't tell my wife any of this, or she would tell me what any rational person would say -- go find a real job.

In The Matrix, Morpheus offers Neo a red pill and a blue pill. "You take the blue pill -- the story ends, you wake up in your bed and believe whatever you want to believe. You take the red pill -- you stay in Wonderland, and I show you how deep the rabbit hole goes." When you decide to take the plunge of founding your own start-up, whether you like it or not, you've already taken the red pill. There is no going back to the contrived reality of suits, face time, and death by PowerPoint. The rabbit hole is deep. Giving up is not an option. The only way through is deeper.

I ordered a company credit card from Bank of America, and miraculously they gave us a $5,000 line. With that new lease on life, Josh and I flew out to Silicon Valley. Only the very rare, lucky or dishonest entrepreneur will tell you fundraising is easy. We found a group of successful entrepreneurs who were willing to take a flyer on us as angel investors. We had to give up a chunk of our company, but they gave us what we needed to keep building. We could stay in Wonderland.