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Big Omaha Backstage Pass – Phil Kaplan: Get in over your head

This summer, you heard their speeches in our Big Omaha Video Series. Now, in partnership with our photography and moving images partner Malone & Company, we’re giving you exclusive access to backstage interviews with the entrepreneurs and innovators who presented at our Big Omaha event in May.

For one week only, the Big Omaha Backstage Pass will feature 10 of our Big Omaha speakers in 15 previously unreleased video interviews. We hope these interviews, with topics ranging from the importance of mentoring to the quest to change the world, will engage, encourage, enlighten and excite you to follow your passion, a message at the core of Big Omaha. 

Our third backstage interview is with Phil Kaplan, a San Francisco-based investor, author and founder of companies like Fandalism, TinyLetter, AdBrite, Blippy and F-d Company.

Get in over your head


The one piece of advice – and this may sound like a platitude or something but I think it’s actually usable – is to get in over your head. Sign up for something that you don’t think you can do. Like, get a job that you’re totally unqualified for or promise something to a client that you don’t think you can deliver. Because I happened to sort of get, like almost like, duped into doing those things when I was getting started as an entrepreneur, and they made me grow so much that I’m really glad I did them.

Bounce ideas off me


I mentor dozens of companies, in some way hundreds of companies … so I’m not only an investor in a bunch of companies, but I’m an active advisor in a lot of companies and then I’m also a mentor in various programs.

I love helping, you know, it’s really fun. I don’t like actively seek these mentor opportunities, but when they come to me, I almost always say “yes.” And in fact, I just started, two days ago, doing like an office hours kind of thing. So I’m picking one day per month and I’ll meet with like anybody that wants to, you know, bounce ideas off me or talk to me for whatever reason, I’m just going do that for a whole day because it more fun for me than it is for them.

To watch Kaplan’s Big Omaha presentation, see our post: “Big Omaha Video Series: Philip Kaplan“.

About Big Omaha and Thinc Iowa, our two premier events:

Big Omaha, a Silicon Prairie News premier event, is held each May to inspire, educate and connect entrepreneurs, especially those with an interest in the tech industry. Visit BigOmaha.com to learn more.

Thinc Iowa, a Silicon Prairie News premier event, will take place for the first time October 20-21 in Des Moines, Iowa. Its mission: Provide a common ground for startups and corporations to explore partnerships, examine innovation and share lessons learned. Visit ThincIowa.com to learn more (tickets still available).

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