jesse middleton

Flybridge is Growing

When I joined Flybridge back in June (wow, time flies!) one of the first things we discussed, as a partnership, was how to…

Who’s crazy enough to join us on a year-long journey around the world?

My buddy, Alex, sent me a note back on April 21, 2016. It seems so long ago. He had one simple question: “A good friend of mine asked for an intro to you. He runs http://www.remoteyear.com. Can I make the…

The Twenty Minute VC

I’ve been a huge fan of Harry Stebbings and The Twenty Minute VC since inception. I’ve heard amazing stories from David Cohen, Dave McClure, Steve Schlafman, Ann Miura-Ko and even my partner, Jeff Bussgang. So when Harry asked me if I would join him on the show I was beyond thrilled…

I agree completely. I hate the idea of just removing a part of who I am at any point of the day or night. This concept brings to mind the song Turn it Off from the Book of Mormon whenever I hear it today. If you’re doing something you love it should never be turned off.

Being incapable of failing is the name of the game

I was having breakfast with a friend and fellow VC (with a shitload more experience) this week and we touched on the topic of the qualities we look for in founders we’d like to back. I’m still learning a lot but we agreed on one thing right…

A few thoughts: Two weeks into this amazing adventure

I’ve heard pitches from 20 companies, I have been to 2 partner meetings and I’ve responded to 350 people about my new adventure which has led to an unbelievable number of breakfasts, lunches, dinners and coffees scheduled in the coming…

My venture into venture (capital)

In February I took a look at my journey into the angel investment world. I had been doing it for only a little over a year, but I learned a ton. I learned that I loved discovering and getting to know new founders. I learned that I enjoyed helping to solve some of the…

A Thank You To My Father On His 30th Father’s Day

On your 30th Father’s Day I wanted to give 30 “Thanks”. So here we go.

Thank you:

• For raising me to be a good person.
• For teaching me about trees and the bird…

“We’ve spent $0 on marketing!”

I see and hear this line from almost 50% of the founders who have pitched me in the last six months. Please stop saying this.

I know it sounds good. You’ve been able to gain your first 1000 users or have made your first $150,000 without spending a…

When should I pitch?

The answer is almost always too early and too often.

The response from this post has been nothing short of amazing. Hundreds of people have reached out to say “Good luck.”, “Let’s hang out.” and “How can I help?” To all of these people I say thank you. I believe I’ve responded to everyone that’s said hi via Twitter, Facebook, LinkedIn, email and text but if somehow I missed you, it was not intentional…

Life is a journey (my last full time day at WeWork)

A little over five years ago I took a few large leaps in my life in a very short period of time where I left LivePerson, started a startup with Mike and Andrew and started WeWork Labs with Adam, Matt and Miguel.