I thought I was joining the future. Then I opened Outlook.
I joined a top-tier venture firm thinking it’d be my dream job. Spoiler: it’s not perfect.
Some expectations held up. Others didn’t. And in a few ways, the reality is actually worse than I imagined.
Let’s start with the people - undeniably smart. Impressive on paper, thoughtful in meetings, sharp in all the right ways. Are they assassins? Still evaluating. But the talent is real.
The tech stack, though? A disaster. This is one of the world’s leading technology investors. We’ve backed world-changing, category-defining companies over the last decade. And yet – internally - we’re running on a 15-year-old version of Outlook, clunky tools, and sluggish machines. We don't even use any of our portfolio companies. It's embarrassing.
But maybe the issue is deeper than tech. Maybe we just never needed it.
We’re been a growth-stage fund. We could afford to wait. Let the early chaos play out, identify the breakout winner, and write a big check once the dust settles. In software, the top player often takes 70%+ of the market. If you bet on the right one, it doesn’t matter when you show up.
That strategy worked in the Cloud and Saas era. A few big bets carried entire funds. But the game has changed.
Returns today? Maybe top quartile, but no longer exceptional. Meanwhile, the market’s getting tighter. Platforms are vertically integrating and moving earlier. They’re beating us to the best companies. The bar keeps rising, and we’re falling behind.
The worst part? In venture, it takes 10 years for the truth to show up. By the time you realize you’ve been playing the wrong game, it’s too late to catch up. Which makes it even harder – and more important – to get this right now.
Here’s the uncomfortable truth: if we don’t evolve, we lose.
Yes, we’re heavily regulated. The SEC in the U.S. and the FCA in London slow us down. We operate more like a bank than a tech company. But that can’t be an excuse.
We have to figure it out because we’re sitting on an under-leveraged asset. Our LP base includes some of the best entrepreneurs and CEOs in tech. That gives us unmatched access. We’ve institutionalized the art of the introduction – our real competitive edge – and layered in world-class founder-facing support across talent, analytics, and GTM. The foundation is there.
But now we need to build on it.
To win the next decade, we have to answer two questions:
What do we believe? Historically, we’ve concentrated on enterprise SaaS - with a bit of exposure to fintech and consumer on the side. That’s been our comfort zone. But the software stack is shifting - AI is rewriting the rules, especially at the infrastructure and platform layers. We need to re-underwrite our core thesis, reassess where real value is being created, and figure out where we can win in the next decade.
Where do we play? Once we sharpen our beliefs, we need to focus. That might mean going earlier. Going deeper. Or going outside the traditional categories we’ve known. The next generation of winners won’t look like the winners of the last cycle - and if we wait for clarity and writing late-stage checks, we’ll miss them.
To play and win in this new game, we need to solve for three things:
- Talent – Start hiring the next generation of people built for this game. That might not mean more ex-bankers.
- Structure – Operate in multiple game modes – early and growth – with real agility and adaptability.
- Tech – Build infrastructure that accelerates us 10x - 100x. Tools that actually augment the team in every single way.
We need to be tech-native, AI-forward, and willing to get uncomfortable. Push the team to adopt new tools. Show up earlier, go deeper, and stop waiting for the dust to settle.
The next era of VC will belong to firms that play offense.