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Confessions Of A Serial Entrepreneur: Jason Cohen On Success & Failure

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by David Garland in Interviews & Guests

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The Rise To The Top mission is simple:

Inspire (and entertain!) you through interviews with successful, unique, passionate, dynamic and creative guests who tell you their story and offer advice based on their experiences rising to the top (minus the fluff). Unscripted. Unedited. Uncut.

Jason CohenMy goal with The Rise To The Top interviews is to bring you interesting, creative entrepreneurs in a variety of fields. Different personalities. Different perspectives. Different stories. Today’s guest, Jason Cohen, has one heck of a story. He has founded four companies, including SmartBear and WP Engine. He took SmartBear from start to multiple millions in profit, without debt or VC, and then sold it for cash.

In this interview with Jason, I wanted to dig deep. To find out his journey. Why he does what he does. Successes and failures. Mentors. Lessons. And advice for hustling entrepreneurs.

Enjoy and, as always, looking forward to your feedback, thoughts, questions…whatever is on your mind.

Connect With Jason (and tell him you saw him on RISE):

On Twitter
On His Blog
His New Project: WP Engine

This Episode Is Ever-So-Proudly Sponsored By:

Rizzo TeesRizzo Tees: You know those funny t-shirts like mullet 2.0 and Props To My Tweeps? They come from my man and former show guest, Chris Reimer at Rizzo Tees. Make sure to check out all the new designs at and in the show notes look for an exclusive link to nab a limited edition “If you want some fluff, go pet a bunny” t-shirt. (No RISE viewer should be without one.)

KISSinsightsKISSinsights: Want to know what your website viewers REALLY think about you? The easiest way is to use the cool survey tool KISSinsights to conduct online surveys. It takes seconds to install and you have seen me use it here on The Rise To The Top. All you have to do is pop in a question and collect your community’s responses. Try it for free.

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Reminders & News:

You can join the 100,000+ RISE enthusiasts and catch new episodes every Tuesday and Thursday, featuring interviews with a unique guest on, as well as iTunes (video and audio) and now on your television via Roku and Connected TV.


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Book Update: It’s here! Smarter, Faster, Cheaper: Non-Boring, Fluff-free Strategies for Marketing and Promoting Your Business is officially on sale! You can grab the first chapter for free right here, and you can buy it on Amazon or anywhere books are sold.

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8 Steps to Turning What You Already Know into a Successful Online Course

The 8 step process to the successful with online courses + free gifts for attending!

Unlock the Offer!