The Twenty Year Itch: My Last VC Investment Out of Brooklyn Bridge Ventures

Sometime in the next few weeks, I’ll complete my next investment. It will be the 105th deal out of Brooklyn Bridge Ventures, the firm I started back in September 2012, and it will be the last deal I’ll be making out of my third fund.

It will also be my last venture capital deal.

I think it’s important in this era of building audiences and living in public to acknowledge that no one actually needs to explain the reasons why they’re making career moves or leaving a company. What you do for a living, how long you do it, and if you feel like that is no longer a fit for you is your business and it doesn’t need to be explained to others or satisfy others’ expectations.

For me, I don’t mind sharing how I think about it. Venture capital is a pretty opaque industry and if I can shed some light on what it’s like to do this, or to decide to stop doing it, I’m happy to help.

I’ll be doing my best to help this company, rolling up my sleeves for probably about two years while I help them get to a much bigger check down the line, written by an investor who specializes in that next stage of growth.

Around that time, I’ll be able to mark twenty years since I started as the first analyst at Union Square Ventures. To put that timeframe in perspective, here’s a picture of analyst me taken at USV’s first office in 2005, dressed in khakis and a button-down shirt versus a picture of me, a GP at my own firm, over 100 deals later, now on my latest Zoom board call from my couch at home with my junior analyst of about a year and a half.

She’s already a seasoned pro—three term sheets got signed in her room at the NICU where she spent the first 80 days of her life.

Last August, I passed the point at which I had spent literally half my entire life working in this asset class, having started at the General Motors pension fund doing institutional investments in venture funds and late-stage directs back in February of 2001.

No matter how you slice it and what endpoints you measure, this is a very long time to have been doing one thing.

I’ve decided that this is long enough for me—especially given the fact that when you’re in venture capital, you don’t just stop. You can stop making new investments, but it will take years to actually work through your active portfolio companies. For me, I have at least two years of active board and observer commitments to roll off of and far more time before all the founders I’ve backed hit (or miss, I suppose) their ultimate goal of returning lots of money to their investors.

It has been a career that fits my personality well. I know it’s a bit of a cliche that VCs say they like to be helpful, but I really do think of this as a service job—not one that’s purely about asset allocation. It’s been incredibly rewarding to be able to offer relevant advice or a connection at the right time and to see when a founder builds on that key turning point and it leads to success.

It hasn’t always been as rewarding as it could be, however. One thing that Andy Weissman told me when he moved from Betaworks to Union Square Ventures, which I didn’t fully appreciate at the time, was how if you’re a smaller, first-check investor, you really don’t get to enjoy your winners. I understand that now, being an investor in companies that have over 100 employees, closing in on $100mm run rates, where it’s been a long time since I was a Board Observer and most of their interaction is with the bigger, later stage investors that came after me. They’re nice enough to send me the board decks, but that’s about all the engagement I have at this point because I didn’t have a big enough fund to maintain my position. While that may have made sense from an investment point of view, keeping my average buy-in price low, it also meant that I missed out on a lot of joy and accomplishment along the way.

Still, I wouldn’t ever have wanted to trade off the pace of deals and the stage that I start with a company to have worked at a later stage fund where capital becomes more of a commodity. I’m proud to have been the first check when no one else was willing to take the risk for so many companies.

I have also been incredibly fortunate to work with world-class investors like Fred Wilson and Josh Kopelman. I’ve backed over 113 companies built by some of the smartest, most ambitious and, most importantly, highest character founding teams—44 of those started by female founders, 31 started by BIPOC founders, 9 by Black founders and 14 by LGBTQ+ founders.

Nearly all of them were first-time founders when I wrote them their first check and I led most of the deals I was in.

While I helped source companies that made great returns for their first investors like GroupMe, Singleplatform, Backupify, and Moat at First Round Capital, my biggest Brooklyn Bridge Ventures wins are still ahead of me, including a company that will do almost $400 million in revenue this year and another big exit that I’ll be able to announce in the next couple of months.

In other words, there’s still lots of work left to do here and the lights will stay on until the last investment wraps up. I’ll just be flipping the sign on the front door to “Closed” for new investments as the term sheet I just handed out will be my last investment out of Brooklyn Bridge Ventures and I will not be raising a fourth fund.

That’s it.

No new investments.

No more responding to fundraising decks.

No more founder pitch meetings.

Honestly? I couldn’t be more excited for what comes next—even if I don’t totally know what that will be.

A few months ago, one of the smartest and most accomplished professionals I know asked me to work with them as a coach and while we’ve only just started, it’s been a great experience so far. It’s likely that I’ll opportunistically take on a few more of those relationships as time allows. It would be great to work with some new investors at the beginning of their careers who are changing the face of what the industry looks like.

I’ll also continue to work within the NYC tech community—now thriving at a level I could hardly have imagined when I first got the pitch deck for USV’s first fund as a Limited Partner at the GM pension fund.

To think, I almost didn’t take that 2004 meeting because it was a NYC-based fund.

Now I can’t imagine anyone wanting to start a company in any other community—and I’m proud of all the work I’ve done to promote it and build connections within it.

What I would like to do is to find ways for the community platforms and events I’ve built to continue on past my involvement—but I have time to figure that out. In the meantime, I’ll still likely accept most invitations to speak to groups of founders if I feel like my experience can be helpful, or hop on a podcast to share my experience like I recently did with Matt Blumberg at Bolster where I talked a little bit about my career and this new move—so you’ll still be seeing me around NYC tech stuff, just maybe not as much as I was when I was 31.

This is how Fred Wilson described me back in 2010.

I took a lot of pride in that when I first read it.

Part of what I’ve always strived to do was to be present and accessible in the community—from the countless panels to the hundreds of neighborhood dinners we’ve organized over the last decade. It was all great fun and I hope it was helpful—and I couldn’t have done it without all the other investors and founders who answered my e-mails roping them into showing up to various office hours events, panels, and other networking events.

What I’ve realized since getting married and having a kid is that the way I've done this job just isn't sustainable over the next twenty years the way I've been doing it for the last twenty--not with a spouse and a fantastic little kid who I want to spend as much time with as possible before she goes to school.

There's a lot more competition than ever from scouts, syndicates, and a whole generation of Gen-Z folks with tiny pools of capital and gobs of free time that spend all their time specializing in the narrowest of verticals trying to predict the next big thing—and the speed of how fast the next big thing blows up these days… I’ve never seen anything like it.

Consider this. I joined Twitter nearly a year after it launched and yet somehow, it had remained under the radar long enough for me to “discover it” on behalf of the venture community to the point where I got a mention in the book about it:

That was 16 years ago and yet somehow it feels like a time in history when crossing the country took six months and someone in your family died of dysentery along the way. What tech stays under the radar for that long these days? The window to show up first to something is so narrow that it honestly feels impossible to do unless your work is your absolute number one and perhaps only priority in life—and that’s just not really where I’m at right now.

First-check investors tend to go one of two ways later in their careers when they start a family. Either they build a firm in order to outsource the screening and sourcing, they don't do as much deal leading, choosing to follow instead, or they go later stage to narrow their aperture to a much smaller set of companies that already have traction and shrink the amount of deal flow they need to look at.

Those paths aren’t professionally desirable to me—so it is likely that what I ultimately wind up spending time on will probably look very different than what I do now, most likely something where the goals, accomplishments, or people aren’t measured in dollars.

Still, if you think I can be helpful in some consultative way in your company, your career, or your life, I can’t help wanting to be helpful—so you can still find me in all the ways I made myself findable previously: Same e-mail addresses, same Twitter (for now), LinkedIn, an Instagram full of cute toddler pics, etc.

Just know that I will no longer attempt to answer all the e-mails as it won’t be my job anymore—not that I ever got to all of them anyway.

I’ll also still be writing a bunch as I would like to do some work thinking through some industry perspectives in hopes that I can make what it is that we do in venture capital a better experience for founders. If you’ve been following along, I’m not always happy about how the industry operates and I plan to be even more forthright about my takes given the benefit of some distance going forward.

I’d like to thank all the Limited Partners who trusted me and who I will not stop working for until the very last distribution check is written, as well as all the founders who gave me a look at what they were up to, not just the ones I backed. I didn’t always make the right calls, as many of you showed me with your successful exits—and I couldn’t have been happier for you.

Hope to see you all at our outing to the Cyclones game and before you ask, yes, we’ll be doing Shakeshack in September for at least one more year. :)