Entrepreneur 2 Entrepreneur: Dana Severson on jumping



Dana SeversonMinnesota tech entrepreneur Dana Severson began crowdfunding experiment Wahooly last fall after identifying a widespread “chicken and egg problem in terms of startup traction and funding.”

Wahooly was original enough to build some quick buzzstrategic partnerships, tens of thousands of early adopters (4:00), and notable launch in February.

Although the site crashed and burned within the first week, the only thing Severson quit was his day job.  Over the following 90 days, Wahooly would come back with validation and cash.

Severson is the first to admit that Wahooly has a long way to go, but he’s already crossed the hardest entrepreneurial line of them all: doing.

TECHdotMN: When asked about a theme which you felt was most relevant to your experiences as an entrepreneur so far, you chose “jumping”. Why?

DS: Because I believe it’s the single biggest thing that holds an entrepreneur back from succeeding. Before you can even get to the point of finding co-founders, raising money, hiring a programmer, etc., you need to commit to the jump. It doesn’t mean you need to quit your day job immediately, it simply means that you need to stop making excuses and start making progress. The stars will never align.

There’s never going to be a perfect time, scenario, idea, etc. If you can’t make the commitment to sacrifice for the good of your company, how can you ever expect anyone else to?

TECHdotMN: How would you describe your jump?

DS: Not quick enough, but I think that comes with the territory. I would guess that most entrepreneurs are impatient, especially when it comes to having the freedom to focus on your vision full time. For me, every day that I spent working on something other than Wahooly was eating at me. But, that desire also bread the creativity to come up with a solution. In my case, we were (and still are) a single-income family of five.

My day job was our only source of income, not to mention insurance. Wahooly had been getting a ton of attention and my wife was starting to buy into the hype. She saw my commitment and believed in the vision, so I got clearance to jump (safely, of course.) We got ourselves to a point where we could support the family for three months financially, so I made the move. At the time the decision was made, Wahooly wasn’t funded, but I did feel that it was imminent.
Split Rock Partners

TECHdotMN: Before jumping, what can be done to increase the chances of a smooth takeoff and a safe landing?

DS: The temptation to go all-in is extremely strong. This shouldn’t be an easy decision, and if it is, it’s probably not the right one. Committing to your idea is one thing, but giving up security, needs to be handled more delicately. It’s not a good idea to go grocery shopping on an empty stomach. Don’t rely solely on your appetite for freedom to make sound financial decisions. Hate your day job, but just don’t quit it hastily.

I believe that you’ll come up with better solutions when they’re not driven by fear. If you’re worried about monthly bills, you’ll only be focused on making short-term decisions. Use motivation as your driver. Most importantly, if you have a spouse, make them a believer as well. Nobody wants the “I told you so” hanging over their head.

TECHdotMN: How do you cope with turbulence like anxiety, or fear of the unknown once you’re in the air?

DS: The day I quit my day job, was the day we launched Wahooly. To put it lightly, our launch was a mess. Aside from the fact that users weren’t happy, we were in the middle of discussions with investors. I literally thought it was over. I had spent the previous five months working towards making Wahooly my future, for it all to coming crashing down on day one. This was the best and worst day of my professional life.

Shit happens and you deal with it. Chances are, your fears are much worse then reality. In our case, we ended up building a better product as a result and users were supportive. Funding came through and all was right with the world once again. Problems suck, but they’re inevitable. I think as time goes, you become more and more immune to the anxiety.

TECHdotMN: Knowing what you do now, so far, what would you do differently before jumping…again?

DS: Personally eliminate as much debt as you can and simplify your life as much as possible. In terms of the business, talk to other startup founders. Listen to their stories and take in their experience. I wish I had done more of this early on, it has been extremely valuable. It turns out that many of our paths are quite similar.

Special thanks to venture capital firm Split Rock Partners for underwriting the Entrepreneur 2 Entrepreneur series.

Previous E2E interviews:

Justin Kaufenberg on acquisitions

David Bagley on bootstrapping

Daren Cox on fundraising

Corey Thompson on focus

Rashaun Sourles on storytelling