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Hack To Start
Episode 165

Jesse Middleton

Investor/Entrepreneur; Founder @WeWorkLabs.

Listen to this episode on iTunes, Stitcher, & Google Music

Jesse Middleton is a startup founder and one of the early executives at WeWork who tackled a bunch of growth and operations challenges before launching WeWork Labs, their own global startup incubator, investment fund, business and digital product development lab. But before jumping into the world of venture capital, Jesse launched and sold a few companies of his own and then spent 5 years as part of the early team at WeWork, growing the company from a few buildings to a worldwide network and pioneer of the coworking and remote work industries. Jesse joins us to share his story, what it was like building WeWork and WeWork Labs, what it was like transitioning into venture capital, his two investment rules at Flybridge, and much more.

Main Objectives For This Episode

  • Learn more about how Jesse got into startups
  • Learn more about what it was like growing WeWork and starting WeWork Labs
  • Learn more about how Jesse transitioned into Venture Capital and what he looks for in investments
  • And more!

Episode Overview

Jesse Middleton is a startup founder and one of the early executives at WeWork who tackled a bunch of growth and operations challenges before launching WeWork Labs, their own global startup incubator, investment fund, business and digital product development lab.

But before jumping into the world of venture capital, Jesse launched and sold a few companies of his own and then spent 5 years as part of the early team at WeWork, growing the company from a few buildings to a worldwide network and pioneer of the coworking and remote work industries.

Jesse joins us to share his story, what it was like building WeWork and WeWork Labs, what it was like transitioning into venture capital, his two investment rules at Flybridge, and much more.


Some Of The Questions We Ask

1:49
Can you tell us a bit more about where you’re from and what you studied?

3:00
So where did you passion for tech and startups come from?

5:26
Can you tell us more about that those early startup days and how you created the opportunity to join WeWork?

9:39
So once you did sell the startup that you were working on and join WeWork in more of an official capacity and start working on WeWork Labs, what was that experience like? What were some of the challenges you were trying to solve and projects you were launching?

16:19
What were some of the biggest challenges you guys were trying to solve as a young company trying to put some of these pieces together and build a network?

22:58
So keeping all that in mind, how were you guys approaching growth? Was it all organic or how would you get the word out there about each new location in the network? And overall, how were you attracting the right types of people to either come work out of WeWork or join WeWork Labs?

26:54
As you mentioned you developed an interest in on the investment side of things, and today you’re one of the general partners at Flybridge Capital. How did you create the opportunity to join the team there?

35:04
We’ve covered a lot of ground in this episode already, do you have any final thoughts or words of advice for entrepreneurs out there building their own thing or looking for investment?


Here are some of the most important links and resources mentioned throughout the show.

Twitter Handles & Websites

Jesse Middleton on Twitter
Jesse Middleton on the web
Flybridge Capital Partners on Twitter
Flybridge Capital Partners on the web
WeWork on Twitter
WeWork on the web
Tyler Copeland on Twitter
Franco Varriano on Twitter

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