Being an entrepreneur can be exciting. It can be rewarding. Stressful? Sure. But what most people at startups don't speak about is the fear that often envelopes them. There are the money worries, hiring dilemmas--even the thought that maybe someone will catch on and realize you don't really know what you're doing.

The need to talk openly about these problems and maybe get advice safely is what pushed Dana Severson to start the site Here's a smattering of the post topics that the site has already attracted:

The topics can be compelling--raw notes from the bleeding edge of business that B-school and rah-rah stories about breakthrough success never mention.

The Big Idea

Severson knows firsthand what it's like to grapple with startup challenges. So, like many entrepreneurs, he built something that might help him solve his own problems. 

"I started StartupsAnonymous because I wanted to air some of my own stories without fear of retribution," said Severson says. He's no newcomer to the issues of entrepreneurs. He co-founded Wahooly, an equity-for-publicity concept profiled by Inc. a few years ago. He went through a funding round, changed the concept in an accelerator, rebranded, and now is trying to rebuild.

Anyone in the startup world is free to post stories or questions with complete anonymity. "This for me is a passion project," said Severson, who purchased the domain name last summer. "There is no safe zone. You have questions, you have issues, you have concerns, and a lot of times it's difficult to talk to people in your network because they're all connected. The time I had my first potential investor call, I didn't know anything. He asked if I was going to have a seed round as an equity round or convertible debt." Severson didn't have an answer. "That's not the image you want to portray to the person you want as an investor. Those are the things you learn the hard way."

Ask the wrong question in high-stakes situation, and you look incompetent. Mention a problem and people might assume your business is in trouble. Advisers might distance themselves and warn off potential investors. Current investors might come down hard. Even co-founders might be looking warily for signs of weakness. How do you trust anyone with a candid conversation that might at least help break a logjam?

"At the end of the day you only can rely on founders who don't have a vested interest in your success," Severson said. The site is getting about a thousand visitors a day, although a couple of posts that ranked high on the technology and entrepreneur social site Hacker News gained significant traffic. StartupsAnonymous doesn't bring in any revenue, though Severson and his programmer co-founder hope that eventually there will be enough "at least to cover the costs."

There is a Q&A section, where people can ask questions and get answers, although because the posters are also anonymous, you have to think through whether the answers seem sensible. Severson plans on adding a short "confessions" section, where in maybe double the length of a Tweet people can get things off their chests. Sort of like a PostSecret, only all about startup business and lacking the artwork.

What ultimately drove creation of the site? "I think there is a lack of realism," he says. "I can only speak to the startup community, but the articles you read and the inspiration you're going after is always about success and what worked. It leaves you on an island. Maybe you're alone, maybe you're not cut out to do it, because everyone else seems successful. I think there's a lot of fear that doesn't get discussed."

Published on: Feb 5, 2014
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