There are a lot of reasons I say no to investing in a startup. Unfortunately an investment decision can be a black box, especially one at the earliest stages of a company's life, so it's hard to pick "one reason."

However, I think founders should have at least some clarity around why they're not getting traction with investors. So, this is an ever-growing list of some of the more common reasons I say "no."

  1. Not enough technology.

    I want to invest in things only I can invest in (risky software/technology plays). If you're selling something that could raise money via other means (e.g. bootstrapping or debt), I'll probably pass.

  2. It's too boring.

    I'm interested in boring problems, but the solutions should still be exciting. Ultimately you will not only need to convince investors, but also early employees, later-stage investors, customers, and more. I didn't get excited enough by the product, team, or long-term vision.

  3. It's too early.

    I invest pre-revenue, but I do not like investing pre-product. I'll do it occasionally, if there's a clear reason why you haven't built anything yet. But generally I am skeptical of teams who have decided to raise money for something that doesn't yet exist.

  4. It's in a tough geography.

    I am open to investing everywhere, but there are certain locations that make it tough. This is mostly due to the path between a pre-seed and an IPO being long and ardous. Tough locations may mean that later-stage investors will wipe out earlier investors, and other things of that nature.

    It may also mean that the governments that regulate you are going to make it more difficult for you to succeed (against global competition).

    Luckily, this matters less and less over time.

  5. The team isn't impressive enough.

    I try to invest in the top 1% of people I meet. This means world-class builders, storytellers, recruiters, salespeople, etc.

  6. There's going to be way too much competition.

    I think what you're building is going to be built by 50 other people, meaning that probabilistically your chances of "winning" are 2%. Unless there's a good reason why it's 20% instead of 2%, I won't invest.

  7. Too many credentials, not enough proof of work.

    I don't like backing a team of titles, especially when there's no one technical on the founding team. I want to back people who can go far with the existing team, because recruiting is really, really hard–and expensive!

  8. It's competitive to Gumroad.

    I'm not interested in helping out my competitors, and I don't want to invest in people I can't 100% get behind.

  9. "It doesn't feel right to me."

    For whatever reason, I didn't wake up the next day thinking about you. Maybe that's a good thing...

For what it's worth, I say no roughly 99.5% of the time. I wouldn't take it personally!