Following up with investors

When I host fundraising workshops for early-stage founders, I usually ask a version of "What is the most frustrating/challenging part of fundraising that I can help you with?" We always start by talking about how to find investors to talk to but inevitably, I'll get to the question about how to best follow up after a pitch meeting. Founders always get confused when a seemingly interested investor ghosts them and want the situation explained! 

I completely get why first-time founders are often left scratching their heads about the best way to follow up - it’s the source of tons of anxiety. Let’s dive in.

Navigating the Investor-Founder Dynamic

The dynamics going on between founders and investors can be a bit of a mystery, especially for those who are new to fundraising. Founders will often put investors on a pedestal, leaving them unsure and lacking confidence in their approach. This uncertainty is only compounded by the conflicting, sound-bite advice floating around. Some suggest treating investors coldly and opting for the "hard-to-get" approach. Others suggest simply being warm and friendly. So it can be very confusing each step of the way, especially right after you finish a pitch.

Instead of providing a one-size-fits-all answer on how to follow up after a pitch, it's crucial to understand the first principles of fundraising and adapt your approach based on the situation and your personality:

Be mindful of the signals you're sending

The first principle to keep in mind is the importance of the signals you send to potential investors. Your actions and communication can significantly impact their perception of you and your startup. When investors are evaluating you, it's a lot less scientific than it might seem. Traction and founder experience/background are obviously important, but don’t underestimate the signals you’re giving off around how confident you are and how much interest there is in the deal. While it might be tempting to email them right away and explain all the X,Y,Z things you weren’t able to cover during the pitch, some investors might take that as a signal that you’re trying to hard to prove yourself and don’t have a ton of other options besides them. Instead of appearing overeager or constantly seeking their response, focus on conveying your genuine interest in working with them and remember that you’re the one giving them an extraordinary opportunity.

Tailor your approach to your personality and the situation

How you follow up after a pitch should be influenced by your personality and the dynamics of the meeting. If you're generally not an emotive person, a colder approach might be more fitting. However, if you're naturally friendly and warm, trying to force a cold demeanor could feel uncomfortable and inauthentic. The key is to stay true to your personality while remaining professional and respectful.

Setting the stage for following up

Now, let me share a specific approach to following up that works for me and I often recommend to founders. Please note that this may not be suitable for everyone.

Here's what I do: when I conclude a meeting and want to create an opportunity for a follow-up without coming across as desperate or overly eager, I set the expectation for the follow-up right at the end. I express my gratitude and mention that I will send the materials we reviewed in case they have any further questions. I assure them that I will be following up to ensure they have all the information they need. By establishing this intention to follow up, the purpose behind your follow-up becomes clear. It's not driven by nervousness or the need for an immediate answer. It's simply because you said you would. As a result, you gain the benefits of more communication, getting a better read on how things are going, and the opportunity to schedule additional meetings or follow-ups. This approach avoids signaling desperation and instead shows that you’re organized, attentive, and professional.

What if you don’t hear back?

A common question I get from founders is, "What if I send a follow-up email and I still haven't heard back in two weeks? What should I do then?

My first response is that this is a great example of a question that you’d be a lot less likely to ask if you’ve followed my principle of calendar density. If your week is lined up with other investor meetings, you’ll be too busy preparing for those meetings instead of waiting for someone you pitched to get back to you.

When a founder receives their first term sheet and truly grasps what genuine interest from a VC feels like, it's a game-changer. They wouldn’t ask this question because they know what real interest sounds like and feels like and have a better sense of when the investor is just going through the motions.

The reality is that if a VC isn't following up with you, it's a sign that they're not that interested. Of course, there are always exceptions to this rule. Maybe the investor is on vacation or they're dealing with a personal emergency. But in general, if you haven't heard back from an investor in two weeks, it's time to move on.

If you do still want to follow up again, the key is crafting an email that doesn't come across as desperate. It's a delicate balance, but try to put yourself in the shoes of someone who isn't anxious or desperate, even if that's how you feel.

Challenge yourself to come up with reasons for when and why you would send a follow-up for NON-desparate. You might want to stay organized, keep on top of your CRM system, or simply maintain communication. Use these reasons to frame your follow-up email, emphasizing that you're checking in to stay organized and manage your process effectively, rather than appearing needy.

For example, you could write, "Hey, it's been a couple of weeks since we last spoke. Our process is still rolling, and I just wanted to touch base to understand where you stand so I can organize my process as efficiently as possible." This approach conveys that you're checking in for organizational purposes rather than out of desperation.

Avoid these common mistakes…

Unless the VC specifically asked for certain information or expressed a need for answers to particular questions, you should avoid selling in the follow-up e-mail. A founder with options doesn’t have to promote so hard and answer something that wasn’t asked - that just signals desperation. There’s nothing you can say over email that will magically change their mind. Keep your communication concise.

I’ve also seen temptation to retaliate if the investor was dismissive or rude. Even if they treated you rudely, there's absolutely to scratching that itch to punch back. It might provide a fleeting sense of satisfaction, but it ultimately holds no value for you. In fact, it likely results in burning bridges, and in the tiny world of VC and startups, a burnt bridge is no bueno.

Final Takeaway… just do it

I wrote this essay to unpack some of the nuances around follow ups with the intention of making you better at it. Hopefully this helps you understand there are situations where waiting and carefully choosing your words can make a difference. The final takeaway on following up is this: if it’s ever a tough call whether or not you should follow up, the answer is always to just do it but with confidence. You can’t go wrong with a confident follow up.