How to Fail Successfully: Take Two Hours to Cry

"Don't underestimate the trauma you will experience as an entrepreneur"

by Liza Mundy
amanda steinberg image
Photograph: Courtesy of Amanda Steinberg

Amanda Steinberg is the founder and CEO of DailyWorth, a media company that provides financial advice to nearly a million women. Before starting DailyWorth, Steinberg had at least four failed enterprises under her belt. When she was an undergraduate at Columbia and already working as a computer programmer, she saw the frenzy surrounding e-commerce and decided to join it by selling a Y2K survival kit online. Problem was, as an engineer, she didn’t know how to market. Another of her ideas was to create an online chat room in which therapists could confidentially discuss cases. Though the concept was interesting, she couldn’t attract advertisers or come up with a subscription fee that solo practitioners could afford. Each successive failure taught her something important: how to market; how to develop a revenue model; how to build an online product that would accommodate limitless subscribers. And all that learning was tested when she started DailyWorth and had to teach herself how to attract investors.

Most terrifying moment: “Raising my first real round of capital was excruciating. Here I was, a mom in Philly. I don’t fit the whole Silicon Valley persona, even though I have this thriving business. After nine months of relentless capital raising, I was on the phone with a group of women who were going to commit a quarter of the funds, but they would not give me a date to close. I said, ‘How about we close in six weeks?’ and they told me I was too pushy, and they pulled out. At the time, my marriage was on the brink, my children were screaming in my bed in the middle of the night, and everything was based on my ability to close this round. I felt like a complete failure.”

How she got through it: “I cried all night. I stayed up shaking. My fear was that the withdrawal was going to send a warning signal and make the rest of the investors nervous. Fortunately, that didn’t happen.”

What she learned: “It doesn’t matter how desperate you are; your desperation does not translate into somebody else’s urgency. Part of being an entrepreneur is that you get up the next day and shake it off. Now I give myself two hours to cry about any failure. Then it’s back to work.”

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First published in the December 2013/January 2014 issue

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