How I Turned A Cold Email Into A $2.5M Seed Round
Everything you’ve read has probably told you that to get a meeting with a VC you need to get an introduction. This is only partly true. An intro is going to increase your odds tremendously, but what if you can’t get an intro? What if you want to meet with Mrs. X, and you can’t find anyone to introduce you to her? Common wisdom might say to keep digging, keep networking and find someone to make that intro, but why not try emailing Mrs. X? It isn’t going to hurt, as long as your email isn’t awful. Even if Mrs. X doesn’t respond, you can still keep networking, hoping you’ll find someone to make that introduction to her.
But how do you write a great email, something that grabs Mrs. X’s attention when she is skimming through her inbox in a Lyft?
Cold Email V1.0: How Not to Do It
Let’s start with how not to do it. Although I eventually convinced Jason Lemkin (from SaaStr) to invest in Mapistry, my first attempt to get a meeting with Jason went unanswered. I had been following Jason’s writing on SaaStr for a while, so when I saw he was speaking at UC Berkeley, I jumped at the chance to see him speak.
I remember a moment in the course of the event when Jason, or one of the other VC’s on the stage, suggested that audience members volunteer to do their elevator pitches and get feedback from the speakers. Pitching would have been a great way to get Jason’s attention, but I chickened out. Instead, I waited around afterward with the hoard of people surrounding him and asked him a short, probably unmemorable, question and then followed up with this email:
On the plus side, I made the email somewhat personal and mentioned something that he had talked about during the event. But a lot is missing. I didn’t explain what Mapistry does, I alluded to it, but didn’t provide a clear explanation. In the second paragraph, I was pretty self-deprecating, which looking back at, I hate. I didn’t brag about our progress; I mentioned our MRR but essentially said “our traction is pretty lame, and I’m sure you wouldn’t want to talk to me now,” which might be true, but why did I say it? Finally, my ask is awful. “Can I reach out to you in a few months…” That isn’t an actionable ask. Plus, I didn’t follow up in a few months! Overall the email comes off as unconfident and vague.
Cold Email V2.0: The Right Way
Two years later, I was ready to make a real pitch. I had worked on my confidence, my social anxiety (I wouldn’t pass up that opportunity to do an elevator pitch again), and Mapistry had made a ton of progress. But I still didn’t have anyone to make that warm introduction to Jason, whom I really wanted Jason to invest in Mapistry. I was looking for an investor who would be an engaged, valuable mentor. I thought the best way to achieve this was to find an investor who had started a successful startup earlier in their career (this is less common than you might think). After reading and listening to Jason through the SaaStr community for a couple years, I found his advice more valuable than anyone else I followed. So once again, I thought I’d try to cold email him (if it hadn’t worked I would have tried to track him down at an event, but it would have been tough.)
I started by putting together a template email that I used whenever I was emailing an investor cold. I shared this template with lots of mentors and got feedback. This was not a quick email I threw together. I spent hours and hours honing the template.
Next, for each investor I emailed, whether it was an intro or cold, I modified the template to personalize it for them. For Jason, who was my number one choice for an investor, I spent a couple of hours researching and putting together the later part of the email. Here is the final product:
My Cold Email Structure
I’m going to break down the structure of this email and why it worked:
- First, the subject line explains what Mapistry does in just a few words (“SaaS for environmental compliance”). It also mentions our biggest point of pride (our impressive customer list). Finally, it tells the reader why I’m emailing them (“Seed” or shorthand for “we’re raising a seed round and I want you to be an investor”).
- The first paragraph explains a little more about what we do, chiefly by describing the problem we solve. The goal is that by the end of reading this paragraph, the reader understands what we do. This paragraph was the same in every email and took many iterations. Explaining what Mapistry does and the problem we solve to investors is not easy. Customers get it because they have the problem, but investors never have the problem we’re addressing, so this paragraph was a tough one. But luckily, figuring out this paragraph is very related to figuring out my pitch in general.
- Next, I hit the reader with some numbers and impressive facts. They jump out because I’m using bullets. I even bold the bullet point that I think is most impressive. My guess is a lot of readers skim this section first, which is fine with me if it gets them interested enough to keep reading. After reading this list the reader knows that an impressive list of companies is buying our solution, we’re growing at a decent clip, and that this is a reasonably large (but not unrealistically large) market. Put some serious thought into what you want to highlight here. You don’t want to wave your hands and give the impression that you’re full of hot air, but you can still choose the metrics that will highlight you at your best. If you have a small but incredibly active list of customers, highlight DAUs and focus less on revenue. For me, I highlighted our customer list, because companies at our stage don’t often have Fortune 500 customers in old-school industries (not traditional early adopters).
- Next, I explain why we are raising money and what we are planning on doing with it. I like this because it makes it clear that I have a plan and a clear reason for raising money. Maybe I could have left this out. In retrospect, I might have included how much we were raising.
- Finally, I make it personal. This is crucial! This is how the investor knows that they aren’t getting hit with an email sent to 100’s of investors, but that you want them to invest in your company. With my most successful cold emails, I spent a lot of time on this part. When I emailed Jason Lemkin, I spent a couple of hours going back over the content on SaaStr, trying to find a piece of content that I could talk about and could make Mapistry stand out. I came across an interview that Jason had done with Peter Gassner, the CEO of Veeva, which I had seen in person the previous year. This interview turned out to be perfect to reference because it highlighted something that Mapistry is doing that is a little contrarian. (We don’t just sell software, a significant portion of our revenue comes from environmental services.)
- Finally, I wrap it up with an ask for a 30-minute phone call or coffee next week. (In reality, everybody gave me 60 minutes, but I thought 30 minutes sounded less intimidating.)
More generally here a few things that this email does:
- It is relatively concise and doesn’t feel like a wall of text. I use bolding, bullet points and short paragraphs to make it feel less intimidating.
- It highlights all the basics: what we do, what problem we solve, what our traction is, how big the market is, and why the investor would be personally interested.
- It includes our deck.
Do Investors Like Cold Emails?
I also got a lot of inspiration from a few blog posts that you should read, including this one from Patrick Mathieson from Toba Capital (Incidentally, Patrick is actually a pretty good fit for Mapistry, and I cold emailed him. He responded(!), and we’ve met a few times. We’re a little early for him, but you never know when we go to raise an A round.) Patrick has a great list of what not to do.
Not all investors are going to take meetings from cold emails, but some do (see Jason’s recent tweet on the subject below). I had a 33% success rate in scheduling a meeting/calls after sending a cold email. Some investors are even vocal about their willingness to take a meeting based on a cold email. So don’t be afraid to give it a shot. But don’t just throw together an email. Put together a draft template (without the personalization) and get feedback on it, do another round of edits, get feedback again. Hone that email (and your deck), and you might get a meeting, and even investment from a cold email. It worked for me, why not you?
A Final Note to Investors
A final note to investors who don’t answer cold emails: if you are looking to make investments in more diverse founders, this is a great way to find them. Unfortunately, the reality is that founders are going to bond with other founders like them. I bond more quickly bond with other female founders. My guess is that this is the same for black founders or founders from any other underrepresented group. So, if you don’t have many investments in minorities, you’re probably going to get far fewer introductions from your portfolio to founders who are minorities. If you want to do more than pay lip service to diversity, reading those cold emails is a great way to increase the diversity of the founders in your portfolio.
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