At the end of the year, I’ll be leaving my job as General Manager of the USV Network after 5 years to join one of our portfolio companies, Bolster — an on-demand marketplace for executive-level talent. In that role, I’ll continue to build connections and community at the unique intersection of VCs, startup CEOs, and their executive teams. In the world of startups, five years is long; in venture capital, it’s only half of a fund cycle. But I picked up a few things along the way. Here’s what I’m thinking about in my last official week at USV.
How do you reflect on a firehouse of knowledge, nuances, and insights over five years?
Do you start by culling through the dozens of notebooks, rife with scrawled-out observations from thousands of meetings with hundreds of people, from New York to Estonia? Do you pore over past attendee lists, speakers, and topics covered across over 400 roundtable events, summits, and manager trainings? Maybe instead, you turn to your inbox. But with the tens of thousands of emails and contacts and introduction requests, it’s impossible to parse the signal from the noise. Then again, maybe it’s Google Docs. Somewhere, embedded in your 230-page document of “weekly status updates” must exist some extractable higher-level wisdom…right?
Anyone who’s worked at a venture capital firm knows that the really good stuff doesn’t exist in any unified, coordinated way. Despite our best efforts, the threadline of VC know-how always seems to remain somewhat out of reach, trapped within the overflowing brains of everyone lucky enough to have a seat at the table. But it’s there. Peppered between the heartbeat of Monday investment team meetings, afternoon coffee dates, and boardroom debates exists an elusive set of axioms. Gut instinct. Pattern recognition. The nagging feeling that you’ve seen something just like this once before, just give me a second to dig it up in my inbox.
As it turns out, the best information simply can’t be constrained by silly things like Google Docs or Airtable or Notion or Slack. Trust me, I’ve tried.
Those of us who dare to pick up the gauntlet of portfolio management know this problem better than any. To the uninitiated, we are, most simply, networkers. The most connected people they know, renown for the mental somersaults we put ourselves through to keep our inner rolodexes sharp. But after five years in running USV’s portfolio network of 100 companies and 10,000 members, I know now this is not a job about networking. It’s about knowledge management. Systems. Processes. Large-scale stakeholder coordination.
We, the so-named “VC portco keepers,” guard our firm’s collective intelligence with the intensity and reverence of a librarian keeping watch over a rare books collection. We’re professional information wranglers, obsessive about keeping all of our connections in one place, about knowing “who’s who” across an ever-growing and ever-changing list of portfolio leaders. As much as we fantasize about waking up one day to a data-collecting system that does the work for us (rather than against us), there’s always an inherent fallibility to any technology we implement. Execs come and go without telling us. Companies change their names without telling us. And yet, still, we chase this utopia of “information complete.”
Peppered between the heartbeat of Monday investment team meetings, afternoon coffee dates, and boardroom debates exists an elusive set of axioms.
At some point along the way, probably after spending 8 hours on a Sunday diligently copying information out of my inbox into an Airtable instance that only three people in the world knew how to read, something made me pause. It struck me that I’d wasted at least two years of my life asking only one question: “How do I get all of the information I need in one place?” While a worthy pursuit, this in itself was not a means to the end. I was crippling myself in details, confusing activity over impact. I realized, if I wasn’t careful, this desire for information perfection could become my great white whale. Perhaps it already had.
So instead I started asking myself something a bit more fundamental: “What would I do, really, if I were to actually get there? How would I spend my time?” I decided to focus on that instead. As it turns out, this is a much more freeing question. It opens up the world to the bigger-picture stuff: Strategy. Insights. Even… fun. I started to get myself into a new mindset. Less: “Figure out how to build a car from scratch with limited resources” and more: “Supercharge your commute by taking an electric bike.” As you might expect, it’s a lot easier to build an electric version of the thing everyone is already using than to dream up an entirely new vehicle.
Who’s Who in VC Platform
I think a lot about the rise of the portfolio & platform leader in the world of venture capital. When I joined USV, the total number of jobs that existed worldwide for “people like us” was about two dozen. When we hosted the very first VC Platform Summit at USV, we fit everyone into our event space — a sum total of about 30 people. Now, this community is 900 strong.
Despite all this time, I’ll admit that I never quite considered myself to be a venture capitalist. Maybe in part due to my role at the firm, a rare non-investor in an industry that values, above all else, the conviction it takes to write a check. Maybe because I always felt a little less like an industry convert and a little more like a study-abroad student, spending a few years out of her native environment to learn a new language.
Maybe because, despite all of the access and exposure to the biggest ideas on the planet, I’d still, late at night, get that nagging drive to just create something myself. “Put me in coach!” I used to think, at board meetings when CEOs spoke about internal projects that needed resources behind them, when partners spoke about just how much work it might take to get something just right.
“No, no,” I’d tell anyone who asked about my quirky job. “I’m not a VC…I just work at one.” Almost as if there was something inherently scary about being on the side with the wealth, the resources, and the power to shape the technological blueprints for the next decade. After all, with great power comes great responsibility. Even now, I still can’t quite wrap my mind around how influence flows and ideas move through this funny industry. Where hundreds of entrepreneurs hire thousands of employees who collectively build products for millions of users around the world. Talk about the trickle-down impact of a single Tweet.
Of course the venture capital industry has been around since long before the era of bringing on community connoisseurs. It’s too soon to tell whether this will be a permanent installation in this industry. I wonder — what will happen to this eclectic crew in the next 5 years? Will we pave the way for a new type of leadership in the VC ecosystem? Start a new wave of companies?
Or maybe, like moths to a flame, we’re simply attracted to disorganized chaos and potential. The next wave of “something big” will eventually need people, resources, and community built around it. Crypto…climate…we’ll be there, adding methodology to madness. Moderating another panel discussion. Taking notes.
Getting the Job Done
Much like any large, open-ended project, the biggest challenge of all in this role is never quite knowing when you’re done. In a world where there’s always more work to do and always more companies to support, at what point do you simply “call it” and move on? In a job where measuring the impact of the work you do is “squishy, at best,” when, if ever, can you sincerely claim success?
Over the years, I looked for signals that this time might be coming. Is it when a portfolio network “alum” comes back to work for another portfolio company in a leadership role? Or when an entrepreneur tells you that the existence of the network was a big selling point in deciding which VC firm to work with? Or maybe when you get asked a question that you can answer with a link to a document in a resource library you already created.
Given the new-ness of this industry niche, there isn’t a lot of past precedent to go on when it comes to how to hire (or how to move on) from these roles. You might look to those who came before, and what they do today. But even that’s a smattering of disparate stories. Some start companies. Some become GPs. Some stay in startups. Some start funds. Some go to grad school. You might not notice any discernible pattern.
I like to think of myself as somewhat of a career chameleon: I can mold and shape to many different environments and in many different audiences. In my career to date, I’ve held roles in sales, marketing, writing, community — ranging from publishing to consulting to startups to venture.
Stories like this are pretty common among this cohort. I’d hire an ex-VC community leader in a heartbeat as an early stage employee at a fast-growing startup, anytime you just need a “catcher” to pick up pieces. But I’d also hire one for a large enterprise org if you need someone to connect the dots with different stakeholders internally or run learning and development initiatives at scale. There’s something to be said for having an “expert generalist” on your team. The person who knows a little bit about everything.
There’s something to be said for having an “expert generalist” on your team. The person who knows a little bit about everything.
“I can’t step away until I’m confident that this can continue without me,” has been my mantra all along. I made that mistake once before, when I left a startup where I was the sole proprietor of the know-how that I’d spent years cultivating. Unsurprisingly, when I left, all of those systems I’d meticulously established left with me, too. And I resolved to avoid that same outcome again. I used to visualize my time at USV like a set of cards on a table. I spent years constructing and holding together a tiny little house with all sorts of funky pieces, paperclips and counterweights. But the true test is — can you step away and see it still standing? Can it sustain a gust or two of wind? And does anyone else know how it’s constructed? Of course, that’s not to say anyone needs to keep things exactly as they were. But it’s important to me that I at least know it could be done — that there exists some institutional knowledge of my mistakes as well as my successes.
To me, there were two catalyzing moments where I realized my time at USV was complete. The first — when our CEO summit achieved a net promoter score of 92. I remember reading the results coming in from that survey, relishing in the success of our keystone annual event and thinking, “I think this is where I top out. I can’t do any better than this.”
The second was when I returned from maternity leave this summer, stepping away from the network activities for the first time in four years. On that first day back, I sat in on our Monday investment team meeting as usual, which happened to include a 30-minute overview of everything the rest of the Network Team did in my absence. Amazingly, they hadn’t skipped a beat. “Where do you need my help? Where are the fires?” I asked everyone, upon my return. “No fires,” they shrugged with a smile. “Just keep doing what’s working.” It took me about 30 seconds to realize that was the sign I needed to finally take the leap onto something new.
Goodbye to all that
Like it or not, there is a shadow persona that looms over all of us in the VC industry. It’s stuck somewhere in between the way we expect VCs to behave and the way we actually do. It chimes loudest on Twitter, on Clubhouse, on Product Hunt, and on Medium. It’s the temptation to disrupt everything, to ask, “but will it scale?” and to pack your schedule so full of coffee meetings that you end every day with the jitters. I had to fight it so hard even while writing this blog post. “Don’t just write the top 10 things you learned in venture capital,” I told myself, repeatedly. “Don’t just make a click-baity (albeit quirky) list about where you’re going and why you’re leaving. You can do something different.”
So I’m not going to leave you with a perfectly constructed list of advice. I’m not going to name names just for the sake of dropping them, nor am I going to give you an easy-to-find reference of every past post I’ve written on VC platform and community over the years. But, much like the signal through the noise of VC in itself, it’s all in here. That is, if you want to look hard enough to find it.
It’s a weird thing to leave a company in an all-remote era, so digital “thank you’s” are about as good as it gets. To the USV partnership, investment team, and network team (past and present) — thank you for all of the support, conviction, and guidance over the years. None of this would be possible without you, and I’ll carry all your conversations and advice with me for a very long time.