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Seth Kravitz: An Entrepreneur’s Guide to Self-Discovery

Casey Gordon | July 21, 2016

“Sometimes feels lost, sometimes found. Varies daily.”

One finds this phrase in the middle of Seth Kravitz’s Twitter bio. It’s a sentiment that at some point will ring true for most people. It’s also a sentiment that many are not accustomed to seeing in the bylines of successful entrepreneurs.

We’re all familiar with the stereotypical narrative: a quirky extrovert with a natural-born knack for sales — probably a millennial — builds an app in their dining room or has an epiphany of the next global tech solution in a coffee shop. Fast forward one year and $50 million in seed money: their personality and their company are one-and-the-same and their name is at the top of every list.

This narrative is a fantasy. For every entrepreneur out there who does fit this mold, there are at least a hundred who don’t.

Seth Kravitz will be the first to tell you he falls into the latter category.

Don’t get us wrong — Seth certainly has his fair share of success. He’s founded three business with two exits to public companies. But the success hasn’t always come easily.

After spending years building his e-commerce site InsuranceAgents.com up to $12 million in annual revenue, a botched update to the site’s technology in 2009 almost imploded the business. With the help of a lucky loan Seth and his business partner Lev Barinskiy did manage to get the company back on track in a matter of months, ultimately selling it to BankRate in 2012.

This episode taught Seth the invaluable lesson that success today does not guarantee success tomorrow, and the wisdom he gleaned from InsuranceAgents.com is certainly reflected in his subsequent ventures.

Technori, one of his more recent projects, has rapidly blossomed into one of the country’s leading startup showcases and has racked up 50 events with 250 companies and $200 million in funding. (Seth will chuckle and point out that one of his main motivations for founding Technori was simply that he wanted to make more friends in the Chicago startup community.)

Seth knows firsthand that the life of an entrepreneur is not for the faint of heart. He wanted to get personal on FIVEinSIXTY with some lessons from his experiences that will not only help aspiring entrepreneurs find success, but also help them maintain their peace of mind along the way.

Seth shares 5 of his strategies for going from lost to found:

1. Writing. Self-discovery is a wonderful thing. Writing is a way to sort out the mess in your head, to work through sources of anxiety or confusion without having to carry them around all day.

2. Therapy. A great way to learn techniques for dealing healthily with stressors as they arise. Mental health is so important. More people should try it.

3. Photography. It’s relaxing to have a creative outlet that’s wholly separate from your work life.

4. Community. Find a community you want to be a part of and join in. Make friends. Participate. If you can’t find the community, make it!

5. Purpose. Finding your place in the universe is important, but do so with patience. Narrow it down as life goes on, and soon enough you’ll find what you’re looking for.

FIVEinSIXTY is our interview series with leading CEOs, founders, and other executives about building amazing company culture, designing creative offices, and creating compelling employer brands.

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