The Rise of Community, the Fund

Today I’m excited to announce that, along with my co-founder, Lolita Taub, I’ve launched a new venture fund called The Community Fund! If you didn’t make it to this post via our site or Lolita’s post, I’d highly recommend you start over on our launch post to learn more about what The Community Fund is all about. In short, we’ll invest in community-driven companies that have the potential of becoming unicorns with a team of brilliant investment partners. Today we’re soft-launching the fund to spread the word about building our team. I invite you to learn more and apply to join our investment team and keep an eye out for our offical launch later on this year for when we start looking at startups for investment.

If you’d like to learn more about what brought Lolita and I (and Flybridge) together, I’ve shared a bit more about my story below.

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If you asked me when I was a kid where my career would lead, I don’t believe I could have ever articulated my path. I grew up in a tiny farm town called Pleasant Valley (we didn’t even have a post office). At the time we had a dial-up internet and BBS’s. I couldn’t have fathomed having been a part of the founding team of a company that went from $0 to nearly $100 Billion and back down again. I couldn’t have thought of investing in startups because I had no idea a career like that even existed. There’s so much of this that was foreign to a kid from rural Pennsylvania. NYC seemed like a foreign land, and I had never heard the phrase “venture capital.” What I did know was that I wanted to work on computers, all day, every day.

The Computer

When I was in the 3rd grade my teacher noticed how quickly I took to the computer lab that my tiny public school had installed. It wasn’t just Oregon Trail or Mavis Beacon Teaches Typing that I was good at — although I was one of the fastest in the whole school district — but I was intrigued and curious by the inner workings of the machine. I wanted to learn more about how it worked, why it worked, and how to make it do more. My teacher was aware enough and kind enough to recognize that my family couldn’t afford a computer of our own so as the lab upgraded their equipment, the school offered to “donate” an Apple IIgs to my family. As soon as I powered up the machine at home I was hooked.

Over the next few years, I continued to sit in front of the computer for hours per day. I learned how to write programs in BASIC, and then Fortran, and eventually the ways of HTML and Perl. I learned how to take the machines apart and to put them back together again better and faster. I ran BBSs out of my home where I hosted tons of content and built online communities around gaming and security. By the time I went off to college, I had started a web hosting and development business and was building web sites for local businesses and hosting other sites all over the world on servers from Scranton to Texas. I had learned a lot about hiring, administrative work, finances and accounting, and management before I was 18.

The Start of a Career

In 2004 I entered Drexel University. The early courses were a breeze. I had had a crash course in business management with my parents’ small businesses and my own. The thing I was drawn to, however, was technology and security. I dove into how to protect computers from the same things I had learned to do to break in as a young hacker. This led me to a co-op where I was not only offered the opportunity to get paid for my work but also one that led me around the world from the UK to China to Mexico and beyond. Up until that point I had been out of the country once before and had never even been to the west coast of the United States. The company I worked for offered to renew my passport and a company credit card, and off I went. This role took me down a path consulting for Fortune 100 companies and eventually an offer to move to NYC to join a fast-growing, public, technology company as the head of technology.

I fell in love with New York almost immediately. The subway was magical (I grew up around tractors, dirt bikes, and the occasional go-kart), the food options were incredible and abundant, and the people were driven and brilliant. I had very little money but took what I had and started to explore the city and everything it had to offer. I discovered the New York Tech Meetup and started to learn about startups and venture capital. I met software engineers whose skills far surpassed anything I had learned. But while I lacked the professional software development chops, I learned about the things I excelled at. I was a good storyteller (thanks Dad). I learned to pitch, to sell, had a product-focused mind, and I was a community builder. When I left my job to start a company of my own it wasn’t long before I teamed up with someone, who would become one of my best friends, and started a community of our own — WeWork Labs.

The WeWork Experience

My co-founder, Matt, and I met the founders of WeWork, Adam and Miguel, early in their journey. We became friends and business partners quickly and launched our own take on an incubator, a coworking space, and a community of like-minded people who wanted to support each other’s journeys. My role was not only to help WeWork grow but also to help each of the founders connect with one another and bring in external resources to help these companies thrive. We worked with massive tech companies like Microsoft and Google but also with lawyers, design firms, and development shops to learn the ins-and-outs of startup building and venture capital. We supported thousands of founders over the years through this community and helped to launch hundreds of startups, many of which are thriving today.

As my role evolved and we grew WeWork from 4 to 4000 employees, I learned a lot about myself. I learned about what I loved doing and what I was good at and what I wasn’t. I continued to hone my community-building skills and my storytelling chops, but shied away from spreadsheets, project management, and managing large teams of people. By 2014, I had also experienced helping founders grow their ideas into real businesses. I decided that I wanted to start to put my investor chops to the test. I had saved some money and felt that I had a knack for picking great founders. I believed that my experience helping others to raise capital, hire, build their own communities, and develop a strong roadmap for their business would be beneficial to anyone that I had the chance to invest in. I started as a small angel writing $2500 checks and learned how I could syndicate deals to the tune of many hundreds of thousands of dollars across our own community. By 2016, I knew I wanted to invest full time. So, when my son was born on Leap Day, 2016, I took a break from work, to spend time with my newborn, and started plotting my course to a career in venture capital.

The Community Fund v1

Yeah. I left WeWork to build a fund. I had never raised institutional capital before so I decided to talk to as many other investors, who had gone down this path, as possible. I went out West and met with first-time GPs, seasoned fund leaders, and LPs and started to build out what my thesis was going to be. I was planning to invest in the community I had been a part of cultivating. Many of the hundreds of thousands of WeWork members had never heard of venture capital. They had incredible ideas, and the skills to execute, but they didn’t come from money to bootstrap and they didn’t have the network necessary to pitch investors on their billion-dollar concepts. As a VC, I knew that I could build the bridge between them and institutional LPs. I planned to leverage the power and insights of the community managers, their relationships with their members, and their knowledge of how hard and smart the members worked to identify some of the greatest opportunities within the ecosystem — this was something that I had been doing since the day WeWork Labs opened. I knew that if I could put capital behind some of these brilliant minds it would lead to outsized returns and I’d love my work every day.

The Flybridge Journey

As I went down the path of developing the fund, fundraising, and building a team, I got to know the team at Flybridge. My mentor and friend, David Aronoff, started helping me think through how my fund would work. At the same time he was courting me to join their team. They had a goal to expand the partnership and to establish Flybridge as a native NYC firm. Having a full-time partner there was important and they were looking for someone deeply embedded in the startup community. As I realized that I didn’t want to build a fund from scratch and I had so much to learn, I dug in a bit more with the Flybridge team. After months of “partner dating” we decided that we wanted to work together. I joined the team and within a few months had already done my first deal and was quickly learning the ropes of running a venture fund.

I’ve had an opportunity to learn from David Aronoff, Chip Hazard, and Jeff Bussgang over the past four years and can honestly say that this is the luckiest break I could have ever imagined. If I think back to when I was nine years old, again, the thing that I truly couldn’t have imagined was having partners who could be friends, mentors, and pseudo-family, at the same time. This was the thing I was missing — I was missing my own, tight-knit, community.

At Flybridge, we have always focused on finding founders early in their journey, identifying those with massive potential, and investing in them early and often. We each bring our own experiences to the table when it comes to helping founders as they build from idea to business and business to empire. We’ve been fortunate to have backed companies like Chief, Codecademy, Crashlytics, Firebase, Imperfect Food, MongoDB, and Splice. More importantly, we’ve grown a community of founders that we feel excited and passionate about working with every single day.

Over the years, we looked at our own deal flow and the communities we met founders from and realized that we were missing out on incredible people in communities we had no access or insight into. We are deeply plugged into the NYC and Boston ecosystems. My partner, Jeff, is a professor at Harvard Business School, Chip has led the charge on open-source startups backing companies like MongoDB and Firebase, and I have a network of hundreds of thousands of people from WeWork but there are still so many underestimated and underserved communities out there. A few years back, Chip and Anna Palmer decided to set out to change that. They founded XFactor Ventures whose fund’s purpose is to make a difference for the next generation of female-led businesses. Their twenty-two partners focus on identifying and investing in billion-dollar opportunities founded by people who we don’t have the fortune of being plugged into. In three years XFactor Ventures has seen thousands of deals and made more than 50 investments. While the fund is funded and operates independently from Flybridge, through our involvement we have expanded our network and relationships and have been fortunate to co-invest alongside XFactor in a number of those companies that we would not have otherwise seen.

The Community Fund v2

We understand the power of community. We have built communities that are hundreds of thousands of people strong ourselves and have helped founders to do the same — whether they’re trying to engage the open-source community to guide product decisions and early implementations like MongoDB or they’re building a company whose product is their community like Chief — we’ve seen it play out and we know the playbook. It’s our entire investment thesis that community-driven companies are better businesses and outperform. In May of 2020, we set out, again, to expand our community.

I was fortunate, at the time, to be following some pretty amazing people. One of them was an operator-turned-angel-investor-and-underestimated-founder-advocate named Lolita Taub. I was enamored with her passion and drive for reaching out and connecting the dots between founders who, like many of the early WeWork members, were not connected with the venture world. She built a Startup-Investor Matching Tool with her husband, Josh, and connected hundreds of founders with early-stage investors who never would have had the opportunity to meet. I reached out to Lolita to thank her for the more than 50 pitches I received from one of her tweets alone! As we continued to get to know each other I asked if she’d be willing to talk to me about launching a fund together. I told her that we were looking to expand our own reach and to connect with founders who were outside of our own communities and that “we believe that underestimated founders can and will produce outsized returns.” I asked Lolita if she wanted to talk about co-founding this new fund with us and she quickly replied with a, “Sign me up!” We set out on this journey together.

Here we are: I am a general partner at Flybridge Capital where we invest in community-driven companies where we lead by example. The Community Fund is a fund that with Flybridge’s backing, Lolita and I, and will run with 9 other partners — a team of incredible investors investing in the most brilliant and driven founders from their own communities.

Lolita and I are looking for your help to recruit investment partners. We’ve begun to talk to operators, founders, and community leaders that we believe will make great investors but we want to hear from you. The Community Fund will be officially launching in October and we’re looking for you to share who you think we should bring on to our inaugural team.

You can read more about what we believe makes for a great investment partner and how to apply or to nominate someone over here. We are looking forward to sharing more as we embark on this new venture!

Written by

VC @Flybridge. Co-founded @WeWorkLabs. Previously @WeWork.

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