A few thoughts: Two weeks into this amazing adventure

Jesse Middleton
Jesse Middleton
Published in
3 min readJun 27, 2016

--

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 weeks. It’s been a phenomenal and humbling experience. I’m beginning something new with amazing partners and, more importantly, with my eyes wide open.

My plan has been to share, in a very transparent way, my transition into this new role. One of the first things that’s been asked by almost everyone I’ve talked to is:

What kind of investments are you looking at? Any specific focus area? Geography? Stage?

I wanted to break down my response so far. I am 100% sure that this answer will change over the coming days, weeks, months and years to come but right now this is how I’m thinking about my journey.

What kind of investments are you looking at?

Great investments. I know it’s a simple answer, without much meat, but it’s the truth. I’m looking for founders with companies that you, the introducer, would consider great. In fact, I would go so far as to say that they should be exceptional, in your opinion, on at least one dimension, such as the founder rocks, the market opportunity is massive or the product is killer. If you’re ever putting your stamp of approval on a person, idea or company, you should believe in them. That’s one way to help me believe in them too. Ultimately my goal is to see as many brilliant ideas as I can and to meet as many awesome people as humanly possible.

Any specific focus area?

While my background (in health-tech, ecommerce, marketing-tech and as an early team member of WeWork) has led me to be particularly interested in marketplaces, SMB-related products, IoT, real estate tech and community-powered consumer products in the past, I want to make sure I’m going into this with my eyes wide open. They say that a lot of what turns a good VC into a great VC is the ability to spot patterns in people, ideas and markets. I’m just beginning to train this pattern recognition engine myself. As I continue down this path, I’m sure I’ll find one or two areas that I’d like to delve deeper into, but for now I’m making sure I say “Hi” to as many people with as many ideas in as many categories as possible.

Geography?

This one is easy. I love New York. I’ve built companies here, worked with the amazing team at WeWork here and, recently, began my new family here (hi Holden and Magda Kozak). This doesn’t mean that I won’t be spending time with my partners looking at companies in Boston, SF, LA and beyond but for the time being this is where I need to keep my eyes and ears open.

I don’t believe that all companies have to start in any one market to be successful but starting a business in New York City has some unique advantages. This post from Mona Bijoor at TechCrunch nails it: Hyphen tech, more diversity and the energy are at the top of those unique advantages.

Stage?

While my history and passion would lead me down a path of looking at super early stage (pre-seed, angel and F&F round) companies, I want to keep my eyes peeled for amazing companies at a few different stages. With the support of my partners, Chip, David and Jeff, I know that we can support companies of almost any stage in their journey. While we’ll continue to push toward investing in more pre-seed and seed deals we’re very open to the idea of coming in at a Series A or slightly later for the right company. Flybridge Fund IV, while very new, is currently made up of 4 direct-to-Series-A and 9 seed investments.

The next 4–6 months…

…are going to be spent in almost pure learning mode for me. I’m looking across the board at everything from consumer to enterprise and pre-seed through Series A/B. Having spent the last 5+ years working with thousands of entrepreneurs in WeWork Labs, I’ve had a lot of time to look at companies across the spectrum. As I learn more I’ll hone my skills, my thought process and my interests but for now I’m happy to look at almost anything you see that you think is great. Feel free to make an introduction or say, “Hi.”

--

--