In 2005, Jesse Lipson founded ShareFile, which he bootstrapped until it was sold to Citrix Systems in 2011 - for $93M.

So how did he do it?

And what inspired him to start Raleigh Founded coworking and his latest venture Levitate?

Let's find out on today's Triangle Tweener Talks!

Where to Find Jesse Lipson:

• Linkedin: https://www.linkedin.com/in/jesse-lipson-625195
• X: https://x.com/jesselipson
• Levitate: https://www.levitate.ai/

Where to Find Scot Wingo:

• Linkedin: https://www.linkedin.com/in/thescotwingo/
• Tweener Times: https://www.tweenertimes.com/
• X: https://x.com/scotwingo

In this episode:

(00:02:30) Does a Philosophy Degree help with entrepreneurship?

(00:06:20) Jess gets caught up in the dot-com boom

(00:09:00) An email signature idea that didn't work out

(00:13:20) The origin of ShareFile, and the origin of a power couple

(00:22:30) Testing Google AdWords - and then spending $300K/mo

(00:29:05) How many dials does it take to book a demo? What's the show rate on the demo? What's the close rate on the demo?

(00:35:00) Selling ShareFile to Citrix Solutions

(00:41:30) Several employees became millionaires because of options

(00:46:00) On selling ShareFile, "I can't decide whether I regret it or not."

(00:47:45) The origin of Raleigh Founded

(00:52:30) On starting Levitate - "I decided I was too young to retire."

Referenced:

• Startup Spotlight: Raleigh startup Levitate, led by Jesse Lipson, lands new partnership: https://wraltechwire.com/2022/03/08/raleigh-startup-levitate-led-by-jesse-lipson-lands-new-partnership/
• Citrix buys cloudy storage biz ShareFile: https://www.theregister.com/2011/10/13/citrix_buys_sharefile/
• Progress acquires file management platform ShareFile for $875M: https://techcrunch.com/2024/09/09/progress-acquires-file-management-platform-sharefile-for-875m/

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Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Earfluence.

• Atomic Object: https://atomicobject.com/