Jesse Middleton

Director @WeWork. Co-founder @WeWorkLabs & @GetBackstory. Investor/Advisor @ThunderclapIt, @JoinTheRukkus, @UseBenny, @inDinero, @fitmobapp & Camelot Metrics.


How are you doing?

Entrepreneurs, have their own special way of answering this question. See if you can spot the pattern:

  1. You just closed your biggest deal or your first term sheet. How are you? I’m doing great!
  2. This weekend your newly-listed-on-Product-Hunt app went down and you lost some really important customer data. How are you? I’m doing great!

Double Your Chances

“Work smarter, not harder” — Alan Lakin (1962)


These words still ring true today, 52 years later. It’s one of the most important skills to learn when you’re growing up with your startup.

I meet with smart, creative entrepreneurs weekly and I usually begin the conversation by sharing a very simple fact that I have no idea what


Hey You, Quit Lying to Yourself.


I don’t read self help books. I loathe them. I believe that you have to actually talk to people, experience life and make mistakes to get better. Reading…


Lesson two: Build something people want.


Before you build your next big idea, ask then people one simple question:

Do you want it?

The Walkie-Talkie Fight

One simple way to argue. Roger that.


Recently my wife and I had a disagreement. What started as a chat turned quickly into an argument. It…


A Recovering Startup Junkie

How I battled serial entrepreneurship and won.


It was less than two years ago when Fast Company shared a story about all of the startups and projects I had started. I had a lot of them but at the time I thought it was cool. And the way to success. Hey, I was a serial entrepreneur.


Creating for Collaboration


When Adam, Matt and I created WeWork Labs a little over two years ago we never dreamed it would grow into the community it is today. We were looking for a place to hunker down with other entrepreneurs working on cool projects who were, most importantly, at the same stage in their business’ lifecycle — crazy, hungry and early. Everyone in the space would need a lot…


Choosing Entrepreneurship

In high school, if you can.


I recently had the honor of speaking to one hundred high school students in 11th and 12th grade in Brooklyn. As…


Dear Intro-Making Friends

No one gives out badges for the most introductions made.


I want to share a few tips on making good introductions that will leave a good, lasting impression on both parties. It’s not rocket science but it isn’t always as easy as it looks.

Be Honest


The Customer Is Not Always Right

But you’d be surprised what you can learn from them if you just stop and really listen.


I wrote a version of this post a little over two years ago on my blog but I wanted to share it again. I’ve adapted it a bit since I’ve learned a few more things along the way.