I share a new video on Angel Investing every week, and in this week's episode, I show you exactly how to think like them
There is a part of angel investing that almost no one talks about openly, but which I have watched determine outcomes more times than I can count. It is not deal selection. It is not market timing. It is not even founder quality.
It is how the deal is structured around the company.
Before reading further, pause and answer this:
When you review a deal, how much attention do you pay to deal structure?
I have been co-investing alongside venture capital funds for years now. More than 100 funds across my angel portfolio and Arāya Ventures. And the thing that changed how I invest most fundamentally came from what I saw from the inside:
How decisions actually get made. What experienced investors focus on when they are inside a round. And where a huge amount of the game is actually played in ways that are completely invisible from the outside.
Here is something that took me longer than it should have to fully absorb. Two investors can back the exact same company, at the exact same valuation, in the exact same round, and walk away with completely different outcomes. Not because one picked better, but because of how their position was structured.
I have seen this play out in a real investment. The company was acquired. Some investors got meaningful capital back. Others, who had invested earlier and believed just as strongly in the business, received nothing. Same company. Same founder. Same exit.
The difference was in the terms. One set of investors had preference shares, whilst the other had ordinary shares. The preference shareholders received funds first, and as it was a modest acquisition, there was nothing left to distribute to the ordinary share investors.
That’s why things like liquidation preferences, pro rata rights, and anti-dilution provisions are not legal details to skim past. They determine how returns are distributed, how much downside protection you actually have, and whether you even get the opportunity to keep investing in future rounds to maintain your ownership.
Most angels only discover this after an exit that should have worked out differently.
In this week's video, I walk through exactly what I learned from being inside 100+ VC-backed deals - the patterns, the structures, and the shifts in thinking that changed how I invest.
A quick exercise, and I would love to hear your answer:
Take the last deal you invested in, or the one you are looking at right now. Then answer these three questions honestly:
If the company were acquired tomorrow at a modest multiple, would you know exactly where you stand?
Do you hold pro rata rights, and if so, have you actually used them?
And when you reviewed the terms, did you model what your ownership looks like across two more raises?
Most angel investors I speak with can answer the first question confidently and struggle with the second and third.
Reply to this email and tell me which one catches you out. I read every reply, and I would genuinely like to know where people are with this, because it shapes what we cover next.
The Angel Diagnostic
The investors who compound over time don't have better luck. They have better systems across four specific dimensions: how they evaluate deals, how they build a portfolio, the quality of access they've built, and the discipline they maintain when it matters most.
Through the House of Arāya, I have built a diagnostic tool that gives you an honest read on all four. Twelve questions. Four minutes. A personalised breakdown that shows you exactly where you stand - and what to do about it.
Warmly,
Rupa Popat
P.s. When you're ready, here are 3 ways I can help:
Follow me on LinkedIn: I share quick takes on deals, founder patterns, and what I am seeing across the ecosystem between newsletters.
Subscribe to my new YouTube channel: I'm releasing in-depth videos every week on how to succeed with angel investing.
House of Arāya Membership: Access pre-vetted deals, co-invest alongside Arāya Ventures, and join a community that pools diligence and shares real perspectives.
