What a good year taught me about risk

It’s been a year.

When I was debating whether to join SeedLegals in 2023, the then Chief Legal Officer promised autonomy but, quite reasonably, told me to expect deal sizes of around £200k–£500k. He wanted to sell the dream, but ground it in reality.

I said that was fine. That’s where the craft matters. Everything else follows.

In 2024, I drafted a PowerPoint deck in SeedLegals’ open-plan office. One slide set out an ambition: to build the best VC boutique in the world.

A few people from the legal team glanced at it and gave a wry laugh (could I blame them?).
When I showed it to my team, they didn’t laugh. They asked, “When do we get started?”

We were focused.
We had a strong team and clients growing faster than most.
That created a flywheel.

In the end, we were finalists for the UKBAA Best Legal Team for Early Stage Deals award in both 2024 and 2025. My last deal at SeedLegals was a $30m Series B for Definely - a phenomenal legal tech company I’d advised since their Series A, and somewhere along the way, become friends with.

That’s the beauty of venture law and the start-up mentality.

Leaving SeedLegals wasn’t about dissatisfaction. It was about recognising that we’d achieved more than anyone reasonably expected - and that, for me, it was time to do it all over again somewhere else.

Moving to Founders Law reset the scoreboard in more ways than one.
Looking back at my journal from the time, my standing at SeedLegals is described as “highly respected”, with the counterfactual simply noted as: “everything to prove.”

What’s helped is that the work itself has been strong. Over the last few months we’ve closed a run of brilliant deals with interesting AI companies (amongst others), alongside a wider team that’s sharp and collaborative. The conversations are ambitious, the standard is high, and there’s a real sense of shared momentum. That matters. It makes the harder parts feel purposeful rather than precarious.

At the same time, something else happened this year that mattered more than I expected.

I started writing.

Duly Noted started as a way to share the insights I wish I’d had along the way. I didn’t grow up with easy access to professional contexts or unspoken rules, and writing became a way to surface the things that are usually learned indirectly - late, or by accident.

Over time, it’s evolved. As the work has broadened, so has the writing. More of the pieces now sit in the space between markets, technology and judgment - written for busy, curious minds who want to understand what’s actually going on, without having to live inside the noise. Short reads, but with the aim that each is evergreen.

Then it crossed a line.

Recently, I came up against a senior lawyer on a deal who had already read it - and thought highly of it.

So this year wasn’t about growth in the obvious sense.
It was about choosing uncertainty over comfort, and learning what that choice actually costs.

Looking back, the signal wasn’t the deals or the moves or the writing.

It was the discomfort.

At some point this year, I asked for things that felt risky.
I said things out loud before I was sure they’d land.
I backed ideas before they were validated.
I chose paths that didn’t come with immediate reassurance.

Not because risk is virtuous - but because comfort is persuasive.

And that’s probably the only question I’ve found useful in hindsight:

Did I do anything this year that made me slightly uncomfortable?
Did I ask for something before I felt ready?
Did I risk being wrong, or looking foolish, or hearing “no”?

If the answer is yes, you were probably stretching.
If the answer is no, that might be fine too - but it’s worth noticing.

✍️ Note to self: If nothing feels awkward, you might not be stretching.