Little Nudges

A short guide to fielding non-obvious inbound investor interest

As an outsider, you can fundraise in two ways. For the first, you can pursue investors who aren’t connected to you yet, and convince them to give you 30 minutes of their time to pitch them. Generally this comes through a cold email. This works. I have done it. Many others have done it. Yet, this path takes a long time to fine tune and there is a high chance it will never lead to an investment. But for many, this is the perceived only path to raise capital.

The other way to raise capital is to build something great and wait for investors to come to you. This is obviously the more favorable option for outsider founder, yet it’s not in their control. It’s up to an investor if they want to reach out and engage. Due to this, many founders opt in for the first option because no investors express interest in their company. Or so they think. Candidly, I call BS on this. I just don’t think most founders are thinking about it clearly enough.

An investor saying they’re interested in investing in a startup does not generally happen as explicitly as founders think it does. In my experience, it comes through little nudges. For example, a like on Twitter from an investor I haven’t met before. A follow from them. A new investor newsletter subscriber. Or a LinkedIn profile view. These are all things that an investor could do to signify they have an interest in what I’m doing without telling me.

Once I feel like I get a nudge, it’s my job to reach out and see if there’s something there or if they really just want the content and nothing else. But in order to do that, I need to message them and they need to reply. Isn’t this the start of how relationships work? If someone followed me on social media, they’ll probably reply if I reached out. And even if there is no investment interest, maybe they can help me with a hire. Or be a mentor. Be a nice internet stranger. Or even invest a year or two down the line. But at the end of the day, being a founder is just about knowing a lot of people. And paying attention to nudges is like using a cheat code.

So if you’re spending all your time doing outbound fundraising, stop for just one second. Has any investor been judging you without you knowing it? Do you have any investors following you on Twitter or LinkedIn? Any newsletter subscribers who are also investors? Any social media engagement from investors? If so, these are nudges, it’s worth your time to reach out to every investor who does one. You never know where it could lead. Also remember, this is the one type of investor you don’t email cold, because for the first time, they may have more context on you than you have on them. Good luck :)