What I'd do differently if I started at 30

This week in the House

Last Friday at the Summer Lounge, we explored a question that is becoming increasingly important for every AI investor: what actually stays defensible when the agent does the work?

As AI models become more capable, many of the advantages that once looked like durable moats are being challenged. Alongside Nicolas Trésegnie, Co-founder of Capably, and Manny Singh from Arāya Ventures, we discussed where real defensibility still exists in an AI-native market, from embedded judgement and deep domain expertise to regulated trust, and what this means for how investors should diligence AI companies today.

This Friday, we’ll continue the conversation with The $1 Trillion Women's Health Opportunity.

Women's health has moved from being one of venture's most overlooked categories to one of the most compelling investment opportunities of the decade, driven by AI, consumer demand, and changing healthcare systems.

I’ll be joined by Kavit Haria, Co-Founder and CEO of House of Arāya, Ann O’Neill Co-Founder of Adora Health and Hannah Samano, Founder of Unfabled, to explore why the category has changed, the businesses now defining it, and what investors are looking for today.

These conversations are part of a bigger theme I’ve been thinking about recently: how investors develop the judgement to make better decisions.

My first angel investment was one I felt good about. That early confidence pushed me to make investments two, three, four and five in quick succession.

Looking back, the speed was the problem. I was moving fast without any of the structure I'd insist on now. If I were starting at 30, four things would be different from the beginning.

1. Access

My first investment was the only deal I was looking at. I invested, and I kept going, but I was still only seeing the handful of deals that happened to reach me. That one successfully exited but still – I wasn’t seeing enough. 

That's a real problem, because angel returns come from one or two outliers, and you can't find an outlier in a pool of five. You need to see enough to be selective, and you need the deals you do see to have had some diligence around them rather than arriving raw.

For contrast, at Arāya Ventures we look at over 3,000 deals a year and invest in fewer than 30. When I started, I was seeing almost none of that. The gap between those two numbers is the gap between hoping and choosing.

2. Portfolio construction

I didn't start with a portfolio mindset. I invested in single companies as they came, with no view of the whole.

Angel investing only works as a portfolio. Ten companies probably isn't enough to catch an outlier. You're realistically looking at 20 or more, built deliberately over three to four years, with a clear view of your total pot, how much you'll hold back for follow-ons into your winners, and how much goes into each company so the maths can actually work.

This is the thing that quietly ends most angel journeys. Someone backs a friend or a cousin, that one company doesn't work out, and they decide angel investing isn't for them. They never really tried it, because they never built a portfolio in the first place.

3. Thesis

I'd think harder about where I was investing, and sooner. But not in the way people assume.

You don't need deep domain expertise to have a thesis. Healthcare became a big part of mine, and it was never my area of expertise at the start. I was interested in it, so I went and learned. I joined other investors' diligence sessions on health startups and immersed myself until I understood the space well enough to have an edge.

So a thesis can come from expertise, like the doctors I've watched become sharp health-tech investors because they see what others miss. Or it can come from genuine interest you're willing to turn into knowledge. Both work. What doesn't work is investing across random sectors with no lens at all.

4. Education

I learned as I went, through the exits and the losses and the badly sized cheques. That's an expensive way to learn.

If I were starting again, I'd put real time into understanding how a successful angel portfolio is built while I was deploying, not years later with hindsight. The discipline you bring to your first five to ten investments shapes the returns you'll see from the whole thing.

Where to start

Before your next investment, it's worth an honest look at where you actually stand. We built a short angel readiness assessment for exactly that: 8 questions, about 5 minutes, across financial readiness, knowledge, network, and access. Most people find at least one gap they hadn't seen clearly before.

I go through all four of these in more depth in this week's video if you want to hear the full thinking.

Warmly,
Rupa

P.s. When you're ready, here are 3 ways you can connect: