I spent last week chatting with a few founders who are thinking about raising money soon. One question that kept coming up was, 'What do you think of XXX firm, and should I raise from them?' Then over the weekend, I saw a tweet from Alana Levin about picking VCs. That got me thinking—so I figured I’d throw in my two cents.

Fund number. VC firms usually raise and manage multiple funds over time. When a firm is just starting out, it's working with Fund 1. If things go well, they'll go on to raise Fund 2, Fund 3, and so on. It’s kind of like how startups move from pre-seed to seed to Series A and beyond. The number of funds a VC has raised can tell you a lot about their ability to find, pick, and win great deals. In fact, many experienced institutional LPs won’t even consider investing until a firm is on Fund 3. Personally, I think fund number is a way better signal than whatever logos a VC throws on their website or the vibes they give off on Twitter.

Fund size. There’s a saying in VC: “Your fund size is your fund strategy.” And it’s true. The way the VC business works, bigger funds usually need to write bigger checks—which often means they focus on later stage deals. Personally, I always prefer working with firms that are the right fit for the stage you’re at. When there’s that alignment, the size of the check you're raising, the support the firm can offer, and the attention you’ll get all tend to line up much better.

Can you learn something new from this person/team? Most of the VCs I’ve met—like 9 out of 10—are super likable. But only a few really stick with me. The ones I remember are usually the ones who teach me something, even if they don’t end up investing. They are not always the "nicest" people but often the sharpest.

How they handle the losses. It’s easy to be supportive when things are going well—but the real test is how they show up when a company’s struggling. I’d talk to founders from their failed bets and see what the experience was really like. That tells you a lot.

Fund vintage year. Most traditional VC funds run for 10 years, but in crypto, I’ve seen shorter ones—sometimes 7 or even 5 years. A fund is usually most active in its early years when it still has plenty of “dry powder” to deploy. As that money gets used up, things slow down and they get pickier. Asking when the fund started gives you a sense of how tightly they might be holding onto their cash.

As a startup CEO, doing deep due diligence on investors isn’t always the highest ROI use of your time—there are usually bigger fires to put out. Hopefully, these tips help you get it done faster and with more focus. At the end of the day, investors won’t build your product or find PMF for you—that’s on you.

I spent last week chatting with a few founders who are thinking about raising money soon. One question that kept coming up was, 'What do you think of XXX firm, and should I raise from them?' Then over the weekend, I saw a tweet from Alana Levin about picking VCs. That got me thinking—so I figured I’d throw in my two cents.

Fund number. VC firms usually raise and manage multiple funds over time. When a firm is just starting out, it's working with Fund 1. If things go well, they'll go on to raise Fund 2, Fund 3, and so on. It’s kind of like how startups move from pre-seed to seed to Series A and beyond. The number of funds a VC has raised can tell you a lot about their ability to find, pick, and win great deals. In fact, many experienced institutional LPs won’t even consider investing until a firm is on Fund 3. Personally, I think fund number is a way better signal than whatever logos a VC throws on their website or the vibes they give off on Twitter.

Fund size. There’s a saying in VC: “Your fund size is your fund strategy.” And it’s true. The way the VC business works, bigger funds usually need to write bigger checks—which often means they focus on later stage deals. Personally, I always prefer working with firms that are the right fit for the stage you’re at. When there’s that alignment, the size of the check you're raising, the support the firm can offer, and the attention you’ll get all tend to line up much better.

Can you learn something new from this person/team? Most of the VCs I’ve met—like 9 out of 10—are super likable. But only a few really stick with me. The ones I remember are usually the ones who teach me something, even if they don’t end up investing. They are not always the "nicest" people but often the sharpest.

How they handle the losses. It’s easy to be supportive when things are going well—but the real test is how they show up when a company’s struggling. I’d talk to founders from their failed bets and see what the experience was really like. That tells you a lot.

Fund vintage year. Most traditional VC funds run for 10 years, but in crypto, I’ve seen shorter ones—sometimes 7 or even 5 years. A fund is usually most active in its early years when it still has plenty of “dry powder” to deploy. As that money gets used up, things slow down and they get pickier. Asking when the fund started gives you a sense of how tightly they might be holding onto their cash.

As a startup CEO, doing deep due diligence on investors isn’t always the highest ROI use of your time—there are usually bigger fires to put out. Hopefully, these tips help you get it done faster and with more focus. At the end of the day, investors won’t build your product or find PMF for you—that’s on you.