The offer that made me stop and think

Last Friday we hosted the House of Arāya Summer Lounge on the $124 trillion wealth transfer, the capital moving between generations over the coming years, and what it means for who makes the decisions and how.

The best part of these mornings is always the questions from the room. What stayed with me was how much of it came back to judgement rather than money. Capital can move quickly, but the judgement to allocate it well takes years to build.

One place it gets tested is when an investment actually works and you have to decide what to do next. That's exactly the decision I faced recently.

Recently, someone offered to buy my shares in one of the first companies I ever backed. The offer was 3x what I'd paid, and deciding what to do with it wasn't as simple as I'd have expected.

Back in 2021 I backed a company called Indē Wild. I met the founders, Diipa Khosla-Büller and her husband Oleg Büller, at an event, and later Diipa called me while I was walking through Regent's Park on one of my lockdown work calls. She told me the brand she wanted to build, bringing the ancient practice of Ayurveda together with modern ingredient science, and I knew almost straight away why she was the right person to build it. After a few calls with her and Oleg, I became the first angel cheque into the company. It was still just an idea then.

A year later, a VC firm I'd introduced led a seed round at almost 5x the valuation I'd come in at. Later there was a pre-Series A at another strong step up. On paper, the growth has been remarkable.

Then, recently, Oleg emailed the earliest investors to say another investor wanted to buy some of our shares. A secondary, at 3x what I'd originally paid.

This is the moment most people don't plan for, and it's a real decision.

The case for taking cash

Angel investing is illiquid. You put money into a startup and you don't know when, or if, it comes back. Acquisitions and IPOs take years. Plenty of paper markups never turn into cash at all. A secondary is a rare chance to get liquidity while you wait.

I learned that the hard way once. Earlier in my portfolio I had a chance at a secondary and passed, holding out for the bigger outcome. Looking back, I wish I'd taken some off the table. That memory was with me this time.

The case for staying in

Venture returns come from your winners. Portfolio construction only works if you let the one or two outliers run, because they pay for everything else. My conviction in Indē Wild is stronger now than the day I invested, and I still believe it will be one of my outlier investments. Selling out completely would have meant giving up the upside I took the early risk for.

What I actually did

I sold a small slice, enough to take my original investment back out, and let the rest ride.

That does two useful things at once. My initial capital is recovered and back in my hands. And I keep almost all of my upside in a company I still believe will be an outlier.

Once your initial cheque is back, you've recovered what you risked and you still hold the shares that could return many times over. For an illiquid asset class, that's a strong place to be.

What this means for you

If a winner in your portfolio ever offers you a secondary, see whether there's a middle option: take your original capital back while keeping most of your upside. Recovering your initial stake and staying in for the rest is often the most attractive outcome available in angel investing.

And if your conviction has genuinely grown, let the upside run. The whole game is staying in the outliers long enough for them to matter.

I go into the full Indē Wild story in this week's video.

The decision to sell, hold, or take some money off the table is one every investor hopes to face. But making that decision well requires more than capital. It requires judgement, perspective and conversations with people who have faced the same questions.

That is what the House is built around: bringing investors together to share perspectives, sharpen decision-making and build conviction.

Our Summer Lounge Series continues with two upcoming conversations, designed to do exactly that. On 24 July we're getting into where defensibility actually holds in AI, which is one of the questions I'm most preoccupied by right now. And on 31 July we're looking at women's health, an area I believe is one of the biggest opportunities of the next decade.

24 July | When the Agent eats the Moats
AI is changing how companies build value and where defensibility comes from. We’ll explore what investors should look for as traditional moats are challenged.
Join us → https://luma.com/frw29zal

31 July | The $1 Trillion Women’s Health Opportunity
A deep dive into one of the most significant investment themes of the next decade and the companies building the future of healthcare.
Join us → https://luma.com/qk94xbrn

I'd love to see you at there.

Warmly,
Rupa

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