A few months ago, I got the chance to join a venture club run by a U.S. VC fund I invest with. More than 200 alumni and existing LPs had expressed interest and around 25 were selected. I was one of them.
We meet once a month to review a potential investment together, with the opportunity to invest in three to four companies by the end of the year. I wanted to learn how people who had been doing this much longer than I had looked at a deal, so I took it very seriously. Before every meeting, I went through the deal room in ridiculous detail. I read the deck, dug through the numbers, researched anything I didn't understand, and showed up with pages of notes and questions. I prepared like I was taking my 12th-grade board exams again.
I have spent much of my career evaluating businesses, markets, and growth opportunities, so that part wasn't new. But this specific venture lens was new, and I found it fascinating to listen to people who had been doing this for decades work through a company and hear what they noticed that I hadn't.
Then I would leave the meeting and keep thinking about questions that weren't in my notes.
If this company became as successful as everyone hoped, what would we actually have helped make bigger?
- What would change for the people who used it?
- Did I care about and understand the problem it was solving?
- Did I believe in this founder and what they were trying to build?
- Would I be happy knowing that some small piece of my money had helped them get there?
A lot of the companies we looked at were in AI, data centers or the infrastructure around them. I could follow the investment case. I could see why people found the opportunity interesting. I was learning a lot from the discussion. Yet, I just kept getting stuck on whether I wanted to put my own money into it.
You don't have to invest in startups to know that feeling.
Someone offers you a bigger job. You have worked for years to be considered for jobs like this; the work is interesting, and the money is excellent. You also know that it probably means another 50 or 60 nights a year in airports and hotels.
There is nothing wrong with wanting the job. There is also nothing strange about standing in Heathrow on a Thursday night and wondering how much you want it.
I see the same thing in companies. A large customer comes along and the revenue is significant enough to get everyone's attention. Winning it might mean hitting the year, opening a new market or giving you a logo that makes the next ten conversations easier. It might also mean changing the product roadmap, pulling your best people onto one account or accepting terms you wouldn't normally accept. None of that automatically makes it a bad customer.
You are deciding how much the revenue is worth when you can see everything else you will have to move around to earn it.
The bigger job has the same problem. You can put a number on the salary increase. It is much harder to put a number on another 50 nights away, or decide how many of those nights would make you turn down a job you genuinely want.
That was closer to what I was wrestling with in the venture club. I wasn't discovering that returns aren't everything. I was trying to work out how much the other things I cared about should influence an investment that might otherwise make perfect financial sense.
So I went back and looked at the angel investments I had made before joining the club. Most were companies founded by women. They were businesses where I understood the problem, liked what the founder was building, and wanted to see her succeed. I also saw an opportunity to make money. I hadn't written any of this down as an investment thesis. I hadn't even noticed the pattern until I went back and looked.
That helped explain why I was having such a hard time with some of the venture deals. I wasn't questioning whether they could be good investments. I was asking myself a more personal question:
If this company does incredibly well, am I glad I put my money behind it?
I don't know yet how much weight I should give that question. I don't know whether it will always matter to me, or whether there will be investments where the financial case is enough. I am still learning, and none of this is investment advice.
For now, I decided to step away from the venture club while I figure out how I want to invest. I am glad I joined. I learned a lot from people who understand venture investing far better than I do, and I suspect I will keep learning from the experience for a long time.
It has also made me notice how often I make some version of this calculation elsewhere. There are things I want badly enough to spend more nights in airports. There are clients worth rearranging a week for and opportunities worth asking more of myself for. I'll probably make investments largely because I think the return could be exceptional.
But maybe the number is only the easiest part to see. The bigger job changes more than your salary. The big customer changes more than your revenue. And an investment, if it works, does more than make you money.
The better question might be: if this goes as well as I hope, what else will it change, and do I want that too?
Until the next room,
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