The “secret” side door into any investor

Side door to a large building.

When a startup founder is trying to raise money, they know they should use referrals to get introduced to investors. But those referrals are hard to get! Usually entrepreneurs try cold-calling investors or asking investors they know to make referrals. Investors ignore cold-calls. It is 100% a waste of an entrepreneur’s time to cold-call investors. Even if you get to talk to an investor in your network, investors tend to be cynical as heck. They have to be or they go broke!

There is a source of powerful referrals that most people don’t know about: fellow CEOs. Investors trust and respect their portfolio company CEOs almost as much as they respect fellow investors. And CEO’s smoke the same “hope-ium” as you :).

Here is a simple process to make it happen:

  1. Make a list of 10 startups similar enough to yours that you can talk shop to the CEO but they are not a competitor, and they are no more than a few years more advanced than you. They’ve probably all raised money. If they have, their investors are the people you want to meet – people who have a track record of investing in companies like yours.
  2. Contact them and ask for advice. Leverage your network if you can, but cold-call if you must. If you ask politely something that boils down to “I’d love to be like you when I grow up. Can I get some of your advice on our next few steps?” If they read your message and ignore you, they are likely a jerk. Any decent entrepreneur knows they only got where they got thanks to lots of help, and they want to pay it forward.
  3. Meet and learn. Do not ask for introductions to their investors. Instead ask them to share what they struggled with when they were where you are now. How did they overcome the challenges? What landmines did they find they want to warn you about? The worst thing that will happen… you learn useful things! But if the meeting goes well, it will turn into multiple meetings, they’ll come to love you, and will personally connect you to their investors.

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