Ten things from ten years in venture

2025 has been an important year. In May, we celebrated the firm’s 21st anniversary and announced our latest set of funds, Uncork VIII and Uncork Plus IV. However, in all of the excitement of that month, two important personal milestones almost passed me by: fifteen years living in the US and ten years as a professional venture investor at Uncork.

Several years ago (during deep, deep Covid), I wrote a blog post about some lessons learned during my first few years in venture: what are some of the things I wish I’d known when I first started? The passing of this year’s big anniversary prompted me to revisit this, so please enjoy these updated bits of advice to my younger self and other new or aspiring venture capitalists.

What Venture Capital feels like at times (image via ChatGPT)

1. Even after ten years, you’re still learning

There is so much to digest when you first start investing, and that feeling of bewilderment will never totally disappear: there are new technologies and business models to understand; the intricacies of portfolio, fund, and LP management; and new and interesting ways later-stage investors can screw you over when things go less-than-perfectly with an investment.

It all reminds me of a childhood trip to Disneyland. You’re in line for the amazing Star Wars ride, and every time you think you’ve reached the front of the line, you turn a corner and the line extends in front of you again. And again. And again. Venture is kind of like this. Whenever you think you’ve got it all figured out, something will happen that brings you down with a bump and reminds you that you’re still figuring it out. And that’s OK — the best investors I know are humble enough to admit this and curious enough to want to keep learning.

2. You don’t want to be the smartest person in the room

One of the magical things about working in venture capital is the opportunity to surround yourself with incredible people — people who are smarter than you, more driven than you, and have deeper expertise in an area than you’ll ever have. VCs should be excellent generalists, but we should be in awe of the founders we back. This may sound obvious, but if you’re sitting with a portfolio company and find yourself thinking that you’re the smartest person in the room, then you’re either delusional or you’ve made a terrible investment decision. Neither of these is a good thing.

3. Your network is your superpower

A benefit of having been around the startup ecosystem for a decade before making the leap to venture was that I’d met a lot of people — founders, technical and commercial leaders, journalists, analysts, etc, who became an extension of my own expertise and network. They’d help me diligence markets and technologies, lend their social capital, and help me win competitive deals.

Like any living thing, your network requires constant care, and you should be extremely careful not to fall into the trap of only taking. I’m a firm believer in karma and the more you put out, the more you’ll get back: take care of your network and they’ll take great care of you. And if you serve the entrepreneur you just invested in and live up to the promises you made, they will likely become an advocate you can call on in the future. Ditto for your co-investors: provide outsized value for them and they’ll help you again and again. I’d been told this going into the job, and then years in, I totally appreciate it: it’s *all* about the people.

4. It really is all about the people

Wait, didn’t I just say this? Yes, but this adage holds equally true for startups you’re assessing as it does for your network. Tripp Jones, my partner at Uncork, has a saying I love regarding what he’s looking for in startups: “Team, Team, and TAM.” In other words, focus on the people first and the market opportunity next. It’s very easy to get tied up in understanding market size and competitive dynamics when looking at a deal, but when you invest as early as we do, you have to be comfortable that shit happens, markets change, and it’s often out of the company’s control. Great people will take it in stride and hopefully figure it out. Mediocre people can’t.

5. Storytelling matters

Great storytelling is a huge competitive advantage. As software creation becomes ever more democratized and we often see several similar companies enter a market around the same time, the ability to tell a compelling story can be the difference between a market leader and an also-ran. Why is this? Storytelling is integral to successful fundraising, selling, and hiring. And the story for each constituent needs to be subtly different. Great storytellers can raise ahead of traction, hire A+ players, and convince early customers to take the leap on their unproven startup.

6. Sometimes it takes time

It’s easy to romanticize the rocketship startup where everything immediately clicks, all the metrics are up and to the right, and revenue growth & follow-on financings happen “effortlessly” (although there’s really no such thing as effortless in startupland). Very occasionally, companies are born as rocketships, but more likely, rocketships are multi-year “overnight” successes with dozens of pivots, rehashes, and near-death experiences along the way.

Early-stage venture is a game of patience, especially when there’s a large surface area of software or truly deep technology to build. Sometimes the most valuable thing an investor can do is stay nearby but out of the way and let the team build. Customer and follow-on investor intros are great, but until the thing is built and ready to scale, they’re just noise.

7. But don’t be afraid to call it

Patience is important, but you can’t be infinitely patient — your fund can’t be around forever, and you shouldn’t cling onto reserves that could be better deployed elsewhere. Sometimes things just won’t click, regardless of how good the team is or how large the market opportunity appears.

Often, the kindest thing you can do for a great founder grinding away in a tough space is to encourage them to think about what the next adventure might look like. If you’ve done your job and invested in great founders, chances are they’ll start something new, and hopefully you’ll want to be a part of it.

Knowing when to call it a day, as painful as it will be, is essential. And understanding how to do it constructively and sensitively can be the difference between retaining an advocate and creating a detractor. More on this below.

8. Everybody talks

When we founded our startup in London in 2007, “Silicon Valley” felt like a distant and nebulous place. It didn’t take long after moving here to realize that it’s much smaller with far richer connective tissue than I had assumed: friends investing in each other’s companies, prolific angel investors with hundreds of portfolio companies, and huge networks like YC’s. This means that nearly everyone is connected (maybe not directly, but closely enough) to everyone else.

We may not always like to admit it, but venture capitalists are service providers. And as with any service industry, customer service is key. The old quote that “a happy customer tells a friend; an unhappy customer tells the world” is equally — if not more so — true here, given the hyper-connectivity in our world. Good reputations take years to forge, but bad behavior can dash them in a moment.

9. Fads come and go. Be authentic but remain curious.

Back in early 2022, while we were raising Uncork VII and Plus III, we got plenty of questions from potential LPs regarding our “web3 strategy” (given they’d been told by many VCs that this was absolutely, definitely the future). What about ICOs? How did we think about distributing tokens? What were the implications of blockchain on the way software is built? We didn’t have particularly good answers to these questions beyond believing it was important to assess each company on its own particular merits (and still having real reservations over the viability of the technology’s primetime readiness).

We were thanked for our time and didn’t hear from many of them again for several quarters (by which time the fund was well closed) when they got back in touch to commend us on our commitment to “unsexy” enterprise software and “traditional” consumer services. In our industry, it’s all too easy to jump around to whatever seems hot, but entrepreneurs are pretty good at sniffing out a phony (plus it’s hard to provide outsized value in an area you know nothing about). Which isn’t to say you should stop exploring, but rather, once you find something you’re passionate about — build expertise, generate a network, and go deep.

🎵 If everybody looked the same, we’d get tired of looking at each other 🎵 (image via ChatGPT)

10. Diversity of everything matters

Having the opportunity to build a team of peers — a group of investors with different yet complementary skills and interests — has been incredibly rewarding. We have people on the team who are exceptional at building and managing relationships, people who are incredibly analytical, and people who find that speaking and writing just come naturally. We have former entrepreneurs, career VCs, and ex-rocketship operators around the table. We have people who love to invest at inception stage and others who prefer companies with metrics and the beginnings of product-market fit. We also have people in their 50s, 40s, 30s, and 20s around the table.

Why is this important? Firstly, as discussed above, networks matter, and the ever-growing Venn diagram of the Uncork teams’ network is a huge asset to the partnership and our portfolio companies. Secondly, nobody can be great at everything, and having a team you can call on to help with the stuff you may struggle with is awesome. And, lastly, quoting legendary British electro band Groove Armada: “If everybody looked the same, we’d get tired of looking at each other.”

Special ten year bonus point: Generational transition isn’t hard if the prior generation wants it to happen

A broadly accepted opinion is that venture capital generational transition is hard, if not nearly impossible. By the data, this view probably holds, but I wanted to offer a counterpoint: it isn’t hard if the prior generation genuinely wants it to happen and is prepared to gradually let go of control and economics. Of course, this is easier said than done (especially when the promise of real future money is on the line), but with a clear plan of how this shakes out for everyone involved (and a healthy dose of mutual respect), it’s absolutely possible.

I have to give a huge amount of kudos to the firm’s founder, Jeff Clavier, who was thinking about this long before it was apparent to me that it was on the cards. He knew that transition takes time (there can’t be a “mic drop” as he rides off into the sunset) and a gradual change in roles (for him, transitioning from sole Managing Partner to co-Managing Partner to a regular GP who can focus on investments, not operations) would set him up for future happiness and the firm for ongoing success.

(Originally published in our Q2 investor letter. Thanks to my Uncork colleagues for proofreading and imagery creation)