Why One Entrepreneur Will Never Sell Her Company

Jen Boulden sold a company for $20 million – with regrets. This time, she’s doing things differently.

Jen Boulden

We can’t sing enough praises for Jen Boulden. After all, she’s one of DailyWorth's advisors. But beyond that, the lifelong environmentalist is famous for creating Ideal Bite, a daily email based on the DailyCandy newsletter model, that delivered tips for green living to more than half a million subscribers. It made Jen a regular on morning shows like The View and landed her a two-page spread in Vanity Fair. In 2008, she and her co-founder sold the company for $20 million to The Walt Disney Company.

You might imagine it’s all smooth sailing from there, but in fact, the story ended on a regretful note for Jen. Roughly a year and a half after purchasing Ideal Bite, Disney, facing a bad economy, a hiring freeze and declining trendiness of the green movement, closed the site.

Jen took some time off — to “lick my wounds,” as she puts it — and to advise other entrepreneurs for a while. And now she’s back with a new company called JenB.TV. It’s like Ideal Bite, but 2.0 — a weekly, five-minute video about sustainable living (how and why to raise chickens, for example), alongside other Web offerings like quick-tip articles and discussion forums. We spoke to Jen about life after Disney and what she plans to do differently this time.

How did the financing work for Ideal Bite?

When my co-founder and I started Ideal Bite in 2005, we thought we could do it with self-financing. We both emptied out our savings accounts, about $20,000 each, and within six months, we were out of money. But we had a lot of traction. I think we had 85,000 subscribers already. So we said, “OK, let’s get a loan” — then quickly figured out that [small business] loans took too long and required too much in interest.

At that time the Internet space was skyrocketing and we had both worked at startups in New York City, so we said, “We’ve watched other people raise money for companies; let’s take those lessons learned and raise our own money.” We went out and raised a friends-and-family round, which was eight people who knew us, trusted us and each put in about $25,000. All of a sudden we had about $265,000 in the bank account, and that took us another year, then we were almost out of money again.

We talked to a bunch of venture capitalists and private equity guys and ultimately ended up taking money from Bob Pittman’s group [Pilot Group], who was also the majority investor in DailyCandy. It was strategic money, as they say. We got all that knowledge given to us in terms of lessons learned and how they had grown DailyCandy. We benefitted from the network and the knowledge from Bob Pittman, who’s wicked smart, and the people he surrounds himself with.

Photo: www.maximomorrone.com

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