001 How to Follow Up the Right Way

When we raised our first round of funding for Encore, I had the opportunity to pitch to a group of angel investors in DC called NextGen Angels. The pitch meeting itself was a thrilling experience —there's nothing like getting up in front of a room of 50 mostly-strangers, pouring out your heart and soul over 15 minutes, and essentially getting judged on something you've put countless hours into. There's a pure rush of adrenaline--it's ridiculously exciting and exhausting at the same time.  

But what I learned that night was that even though the pitch itself was important, what came afterwards was the real difference maker. After the pitch, the whole group moved to a nearby bar to have drinks. The majority of us, including myself, stayed until around 11 — I went home feeling completely drained, ready to sleep. But for whatever reason, I decided to shoot off some emails before turning off the lights. I sent each person I had met that night a quick note telling them how much I appreciated their time and interest, and that I'd love to schedule a follow-up coffee chat in the coming weeks. 

I found out a bit later that this gesture had made a much larger impact than I had thought. The investors later told me that they had appreciated my quick follow-up, and it showed them I was willing to hustle and someone they would enjoy working with. What really surprised me was when they told me that not only do others typically follow up much later, but many entrepreneurs don't even follow up, period!

It seems like such a small thing for sure, but hey — when you’re a younger entrepreneur with a shorter track record looking to raise money, these small things matter.

To me, following up is a no-brainer: it's a small action that can have a massive impact. When somebody — whether it’s a mentor, a potential customer, or someone you met at a conference — takes time to meet with you, you need to follow up. Here's a playbook I've found effective:

1. Get their information

I cannot emphasize enough how important this is, especially if you're meeting someone at an event. Often, the person you meet will ask you for your info ("hey, can I have your business card?" or "can you give me your email?"), and we mentally fall into the trap of thinking that's good enough. Trust me, it's not — there's a reason I have to write this post. Most people just don't follow up!

Instead, own the responsibility of getting their information and following up, even if they say something like "I promise I'll follow up."  

2. Follow up as soon as you can

This is where things get really unsexy (and where people like us make our money). The difference between you following up right away versus saying "I'll do it later" is the difference between your email hitting their inbox while you're still top of mind versus your message being lost along with all the others. You can always mail a handwritten card later on for bonus points, but I'd recommend still sending a quick email in the meantime. 

3. Show your thanks

Showing how much you care and appreciate meeting them matters way more than how good of an email writer you are. 

This is a template that's worked well for me:

“Hey Jesse, 

Thanks again so much for taking the time to meet with me today. 

I really appreciated the advice you gave me about specific topic X and specific topic Y. I’m really excited to share your thoughts with the team, put your guidance into action, and will follow up after we’ve tried it out. 

In the meantime, I thought of this article z I read recently when chatting with you. Thanks again!”

If you do all of the above, you're already doing better than 90% of entrepreneurs. But here's how you can really build lasting relationships:

4. Maintain the feedback loop

Remember the last few times you recommended a book or a podcast to a friend. Have you ever had a friend come back and say something like, "hey! I actually listened to "Radio Lab," and it was awesome — I listen to it every week now!" It truly is one of the best feelings.

Turns out, advisors and investors are human too (shocking, I know) and love hearing the same thing. There is nothing — nothing — that makes a mentor happier than seeing some of their advice actually be put into action and receiving an update on how things have gone. Seriously: a mentor or advisor getting some equity or compensation is nice, but what makes the relationship so fulfilling is this “feedback loop.” It’s even fine if you come back say, “Hey Jesse, we tried this — but it didn’t work,” because people are rarely always right but it will get them to help you even more. Essentially, it makes them feel like they’re a member of your team. And that is the strongest feeling. (Yes, that does mean you actually need to absorb their advice and do the hard part of executing on it.) 

One more note to this: especially when you’re first starting out, mentor relationships can often feel like you’re doing way more “taking” than “giving.” That’s true, and inevitable. But following up over and over again in the long run is one of the best ways you can give back. When I’ve been on the other side mentoring someone, what I get is a sense of accomplishment, a team to root for, and real feedback on whether I was right or wrong that I can incorporate into my pattern recognition for future meetings.

I’ll be the first to admit that I'm not perfect at following up quickly every time (especially through the last step), but it’s something I’m working on improving — because every time I do follow up, it results in the most meaningful and helpful relationships. It’s hard and boring — if it wasn’t, everyone would be doing it. But it’s the type of thing that makes you stand out amongst all entrepreneurs (not just student ones) and pays off huge in the long run, when you have an army of smart and experienced mentors at the ready to help you with any challenge your startup faces.

If you like what you see, it'd mean the world to me if you share this on social and/or subscribe to the email list (below). A lot more coming!