Breaking down million-dollar emails
Another example of someone who’s invested millions as a result of cold emails is Jason Lemkin. Fortunately, we don’t have to guess what it took to get his attention. He’s published the emails and shared why they worked.
Here’s the first one:
Here’s what Jason had to say: “It is really strong. Not just the metrics, but the case studies, the sense of the go-to-market strategy, and more. Lesson: anyone would want to take this meeting.”
Let’s break down what we’re seeing.
The greeting: “Hi Jason.” When you’re pitching a big-name investor, it’s easy to think you have to be formal. However, opening with “Dear Mr. Lemkin” sounds like the start of a letter from the bank or, even worse, a scam email. Being respectful is great, but there’s no need to be overly formal.
The opener: Tiago doesn’t waste space on trite niceties, asking Jason how he’s doing and that he hopes his family is well. He doesn’t even go for any flattery, saying how much he admires Jason and the work he does. Instead, he dives straight into the reason for his email. In two sentences he introduces the business and its advantages. Short and sweet, with a link to the website if Jason wants to check it out and learn more.
The stats: Tiago then outlines all the details that an investor would likely want to know. These are all cold hard facts, with the MRR down to the last dollar (and backed up with a screenshot if an investor wanted to verify it). This is all presented in bullet points, so it’s easy to scan and digest without going through a wall of text.
Case studies: Finally, Tiago gives some case studies, so an investor can go beyond the stats and see how the business is working in the real world. He’s able to drop some big names too, which helps, but more importantly he’s able to give details and concrete numbers. Rather than making baseless claims, the results speak for themselves.
Let’s take a look at the second email.
Why did this stand out to Jason? “It does a good job of summarizing the opportunity, early customers and traction, growth profile, and market size. Perhaps just as importantly, it is truly personalized. Also for me at least, it’s low drama. “Do you have any time the week after next?” The confident and relatively data-rich but low drama emails work best. Knowing there’s a little time makes it much less risky to meet a founder you’ve barely met before and dig in.”
I love the idea of a data-rich yet low drama email. Let’s jump in and break it down a bit further to see exactly how it works.
Subject line: On paper, this goes against everything you’ve ever read about subject line length. It’s massive, far longer than what I’d normally recommend. However, in spite of its length, it’s still concise, giving plenty of information:
- The company name (“Mapistry”)
- What the business does (“SaaS for environmental compliance”).
- Why investors should care (“Fortune 500 companies”)
- Why Allie is emailing them (“Seed” funding)
While I still wouldn’t recommend using needlessly long subject lines, this example makes it clear that clarity is even more important.
The greeting: Again, as with Tiago’s email, Allie keeps it simple and relatively informal.
The opener: Allie very briefly introduces herself and her company. No niceties, no unnecessary questions, no wasted space. The rest of the opening paragraph describes the problem they’re solving, all in easy-to-understand language. It’s deceptively simple. As Allie explained afterward: “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.”
The stats: Again, Allie uses bullet points to highlight the facts and figures an investor would want to know. At a glance, you can see the company’s current customers, their growth rate, their revenue, and more. As an added bonus, she includes a link to a presentation if the investor still wants to learn more.
The plan: This is where the two emails differ. Rather than going into case studies to illustrate her business, Allie goes into why she’s emailing and what she would do with the investment. Investors still like to know where their money is going, and that it isn’t just going to fund the biggest office party ever.
Personalization: Something that we always encourage at Reply is personalization, and Allie does a great job of it here. This isn’t a quick one-liner mentioning previous companies the investor has funded; Allie uses a couple of paragraphs to show, in a natural way, that she’s done her research. At the same time, she ties it back to her business, so that it’s relevant rather than a vague compliment to the investor.
The conclusion: Allie finishes off the email with a request for a 30-minute phone call or coffee next week, which is a great CTA. It’s highly unlikely that an investor will be ready to invest in you off the back of one email, but if you’ve done a good job with the email, 30 minutes of their time to learn more about a potentially lucrative investment is a much more reasonable request.