How To Convert Customers With Cold Emails | Startup School

[Music] Hi, I'm Aarin Epstein, Group Partner at YC, and in this video, I'm going to talk all about how to write cold emails that convert.

So first, I'm going to give you the all-time best email outreach hack. You ready? Get a warm intro! This is the most effective way to get people to respond to emails that you're sending to them. You're going to have a conversion rate two to three times what you would get if you were just sending a regular cold email.

There's a lot of different ways to get warm intros to people that you're trying to get in touch with. Mostly, you want to use your network and go through LinkedIn—all of your contacts. Look up your friends, your friends of friends, current or former co-workers, your school alumni networks that you're a part of, and even employer alumni networks at past companies that you've worked at. You basically want to turn over every rock and stone to try to find people that might be able to get you a warm connection to the person that you're trying to get in touch with.

It's not always possible to get a warm intro, though, and many times you've got to go in cold. So that's going to be a big focus of what we're talking about in this video, whether it's for sales, recruiting, partnerships, or whether you're just trying to get some of your users to talk to you or even reach out to other founders as mentors to give you advice. All of the tips in this video should be useful for you.

The good news is that most cold emails are actually terrible, so the bar is really low for you to stand out and get somebody to pay attention and respond to you.

The first thing that I'm going to talk about here is mapping out your funnel. To do this, you want to start with your goal. For many of you, if this is a sales context, your goal is going to be: I want to get new customers. So your goal is to get one new customer, let's say. Then, what you want to do is work backwards from that goal to build your funnel, which I'll walk you through now.

We're going to take a look at what a typical conversion funnel might look like if you're a B2B software company. I'll give some sample conversion rates as we go through this example here, but it's important to note that yours may differ, and you're going to need to figure that out through trial and error yourselves.

Let's say your goal is to get that one customer. Then, let's say you have a funnel where you need to give product demos to convert people to a customer. Let's say you know that your demo-to-customer conversion rate is 10%. Well, in order to get one customer, that means you're going to have to give 10 demos to get that one customer.

Now, in order to get 10 demos, let's say you know that you have a 25% conversion rate from people that respond to your email to people that actually sign up and show up for a demo. This means that you need 40 responses from the emails that you send in order to get 10 demos.

Now, in order to get 40 responses, you need 400 people to open your email if you have a 10% conversion rate from opens to responses. Then, in order to get 400 people to open your email, if you have a 50% conversion rate from emails sent to emails opened, that means you need to send 800 emails to get those 400 opens.

When you look at this all in aggregate, basically, what that means is you need to send 800 emails in order to get one customer conversion. If you're expecting to just send a handful of emails every day, every week, every month, and see results, that's not going to cut it. You're going to need to send dozens of emails per day—possibly even 50 per day—to see meaningful results with conversion rates similar to those that I showed.

You should plan to start writing these emails manually and personalized—doing it yourself, not starting with automation. You have to do it manually first so that you can learn and figure out what works, so that you can then start to scale the process more.

It's important to remember that the goal is not to make the sale right away in the first email; your goal should be actually to get to the next step in the funnel. That's all you should be focused on here.

As you're optimizing your funnel, you want to make sure that you're tracking and measuring your conversion rates so you can figure out what they are for your specific situation. This is really important because it helps you understand where to focus your efforts. If you have an especially low conversion rate at one step in the funnel, it might mean that there's a lot of room for improvement that you can do to bring those numbers up, which will help improve your conversion rates across the entire funnel.

I wish I could give you industry standard conversion rates for each of these steps, but the truth is they're all different. It really depends on your industry, your brand, your product, and even the customer type that you're going after.

One thing that's important to note is that conversion rates will decrease as you scale. So if you're starting out in the early days and you're writing these emails manually and you're not getting good conversion rates, then that's something you should fix before you start to scale—because they're only going to get worse as you grow in scale. By definition, you're going to be going after potential customers that are not your most ideal target as you start to grow.

Now, let's talk about how you can increase open rates. The most effective way to increase your open rates is going to come through better targeting. We talk a lot at YC about making something people want, and targeting is really all about finding the people that want it. This is the highest leverage thing that you can do to improve your open rates and your responses because it's better to send 100 targeted emails that are going to have a much higher open rate and a much higher likelihood to respond than a thousand untargeted emails that are mostly going to be deleted.

The thing is you should get better at this over time as you learn to qualify your leads better. This is an iterative process. This is effectively the screen that your recipients are going to see when they're trying to decide if they should open your email or delete it. It's an email client—you basically see the name of the sender, and you see the subject line, and maybe a tiny preview of that first sentence in the email.

The "from" in your email should just be your personal name; it's better because it feels like it's coming from a human rather than a company. The subject should be something that's short, relevant, and interesting: "Hey, quick question," "Can I get your advice?" "Help a fellow founder," "Hello from your company name." These are all great examples that are just really simple, don't feel overly salesy, and feel like your friend could have written them.

When reaching out to people, I've found that the ideal channels to contact are email, which is usually better; LinkedIn is usually worse. If you're text messaging somebody, it can be even more personal, but only do that if you have their explicit permission. Otherwise, if you get a text from somebody and you don't know them, it can almost feel like an invasion of privacy sometimes.

This isn't always true for all industries. There are some people where, you know, they get LinkedIn messages all the time, and it feels overwhelming for them—they feel like it's filled with spam. So you don't want to fall in that category. There are some people that never get LinkedIn messages, and it feels special to them when somebody reaches out. So you're going to have to adapt this for your own specific industry and use case.

When it comes to finding strangers' emails, there are a few different ways that you can go about that. First, you can ask someone who knows them if they have their email address that they can share with you. Although an intro from that person would obviously be better, you can try to connect with them on LinkedIn or look up their blog or the website if they have one. Oftentimes, people will put their own personal email address there.

You can use the LinkedIn Sales Navigator tool, which is a great way to find relevant people to reach out to and also contact. Sometimes, you can even guess based on the company format—if you know that everyone at the company has first name.lastname@companyname.com, then you can probably guess just about anybody who's working there and be able to reach them.

There are even really great tools that can help make this pretty simple too, like apollo.io, hunter.io, clearbit, and many others. So it's worth checking those out to find the right email address.

Building your brand is really important when you're reaching out. It's important because your company brand—when you're really small—actually isn't going to help you. It's not going to open doors. Nobody knows who you are. But it will help you as you scale if you do things right.

So what's important to remember in the early days is that you are the brand. The words that you use, the way that you reach out, the level of personalization, and the effort and work that you've shown in reaching out to somebody will really stand out to people. You basically are trying to get users, customers, partners to not just make a bet on your company but to make a bet on you personally in order to work with you. It's risky working with a startup, and so if you can put your personal cell phone number in there and tell them to reach out to you at any hour of the night if there's anything that they need, that's going to feel like you really care and you're going above and beyond to make them successful.

It's important to remember that the highest ROI when it comes to increasing open rates is really going to come from better targeting.

Now let’s talk about ways to get more responses. Once people have opened your email, it all comes down to what you write and what you say in that email—whether they're going to respond or take the action that you want.

In order to guide you through this, I've come up with seven principles of effective email copy that are going to help you write emails that stand out.

The first is to have a focused, specific goal. Your goal can be getting to the next step in the funnel and starting a conversation with them, and you want to keep it focused on a single outcome. You want them to respond, click, intro you to somebody—whatever the action is that you want them to take—and you want to focus just on that one outcome and moving them towards that action. If you have multiple asks or multiple things you want them to do in the email, it can create a paradox of choice, and then this feels hard and overwhelming for the recipient. If they have too many things they want to do or it's not clear which is important, they're just going to either delete your email or shelf it, archive it, forget about it, and move on.

That's why it's really important that you have this one focus goal. All the copy in your email should drive towards that single goal, and every word counts. If there's anything that doesn't move the recipient towards that goal, you should delete it.

The second principle for writing effective emails is to be human. This really helps to talk about emotions—things like "I'd love to," "It would mean a lot," "I'd really appreciate," "Thanks, you have no idea how much this helped." Because humans talk about emotions, and bots or LLMs or whatever else you're using to try to automate this process are not good at this type of thing.

It helps to be informal. Instead of "Hello," or sometimes I get emails, "Hello, Mr. Epstein," and I don't take those very seriously. Versus if somebody says, "Hey," or "Hey, Aaron," and you can even have no capitalization—typos can be okay. These are all things that make me think that a human has written this email rather than a robot. You can even get creative with GIFs or videos or other types of custom content to get people's attention, and the more personalized it is, the better.

I remember one time somebody sent me an email, and in it, they had an animated GIF of them holding a little whiteboard. It said, "Aaron," it had my name on it, and it said, "Hi Aaron," and she's waving to me. That got my attention! I clicked through; I wanted to see what this was about because it felt like they had done something very personalized that probably took time to create, and that made me think that they actually cared about building a connection with me rather than just spamming thousands of people, of which I was one of them.

The main point to emphasize here is that you really want to write how you talk to a friend. This is super important. A lot of times, people will go and they'll open up a Google Doc and they'll start writing out a generic email with sequences and placeholder variables for company name and recipient name and all these things. That’s not a good way to do it. Instead, you want to open up your email editor just like you're composing an actual email to a single person. Put the specific person's name or email address in the "to" field, and then write the email with that specific person in mind.

I know it's tempting to use LLMs and other techniques to try to automate a lot of this, but they often struggle with a lot of this personal connection here. A final trick here: once you've written that personalized email to one specific person, read it out loud either to your co-founder if you have one or to yourself, and see if it feels awkward. Anything that you're saying—if there's something that you've written that you wouldn't feel comfortable saying out loud to somebody, that's probably an indication that you should change it to be a little more human.

The third principle here is to personalize. Everyone's used to getting tons of spam, and people can smell spam from a mile away. That's why personalization and making it feel targeted is super important to avoid the delete button. Everyone loves their name! The difference between "Hi there," which feels generic, versus "Hey Aaron," feels like it was written for me—very simple to do, very simple bar across, and it helps to be specific in the personalization that you're writing.

A lot of times, I see founders say things like, "Hey, love what you're doing at Creative Market," which was my startup, and this feels kind of generic. It feels like there was a placeholder variable for company name and they just swapped my company name in instead. If somebody writes to me and they say something like, "I'm a huge Creative Market fan. Ever since you launched the Photos category, it's now my go-to resource," that shows me that at the very least, they've done some research on my product and the history of what we've built and how it's evolved. At the highest level, maybe they're actually a user of my product, in which case I would be super excited to respond to them and get to know them.

The key takeaway here is that if you're just swapping out a few words, it's probably not specific enough. One really important point here to help with personalization is that you want to try to find the uncommon commonalities with the people that you're reaching out to. Uncommon commonalities are things that you have uniquely in common with somebody else—things that are not obvious to have in common with other people.

For example, if I'm reaching out to somebody and I say, "Hey, I see that you are a man; I also am a man. We should do business together." Then they're going to be like, "Okay, that's a little weird." It's a lot of people that are like that versus if somebody reaches out to me and they say, "Hey, we went to the same college and went to class in the same buildings," instantly I'm starting to build a connection with them, or I feel like we have something in common, and I want to get to know them better. I want to help support them because I know what it's like to be in their shoes as well, and it's not easy to figure out what these uncommon commonalities are.

That means that you have to do the work—you have to put in the work to research the company, find the right contact, look them up on LinkedIn, use their product so you understand at a deep level how it works, and then reach out to the person. That’s how you're going to be able to build the deepest connections and get the most responses.

All right, the next principle is to keep it short. If you've got a wall of text, that's just going to be an instant delete for most recipients. You want to focus on making it short because your email will then be easy to read and respond to right away. Most people are pulling up emails on their phone. If you can make it so simple that they can just hit reply and fire off a quick response or link—whatever the thing is that you want—they're going to do it right there in the moment.

If it's something that has more cognitive overhead, is longer to read, then it means that people are going to put it on archive, maybe flag it to try to respond later, or else just delete it altogether, and your email will be lost.

The fifth principle for effective cold emails is to establish credibility. If you're in YC, often that can be credibility enough to open doors, but if you're not in YC, this can be through former schools that you've attended, companies that you've worked at, or other impressive things that you've done. You can include all of this in your email to get people to take you seriously right out of the gate.

Also, if your company is live and you have customers, you can share some well-known customer names as social proof in the email too. If people see that either they're competitors or other well-known customer names that they know are using your product, then that can provide a lot of credibility for them to get excited to use you too.

If you have any interesting or useful data or trends or anything that's industry-specific that your customers might find interesting or relevant, you can publish that too to help establish yourself as an expert in the space. If you have any shared connections, people that you know in common and that sort of thing, it can be great to mention that too because that'll create a baseline of trust.

The sixth principle here is that it's all about the reader—not about you. This means that as you're writing your copy, you want to reframe all the "I's" as "you" and "yours." The trick here is to tell your story as the quest to solve the problems for your users. This works especially well if you are solving a problem that you have felt yourself.

For example, if you know at your past company you ran into this problem—it was a huge headache for you—and now you're building this company to solve it, you should tell the user that. Tell them that you're dedicating the next 10 years of your life to building this company to solve this problem that you felt so deeply that you know that they feel too. People are really going to connect if they know that you understand their problem too, and they're going to want to share everything with you so that you can hopefully fix it for them.

It's also important that you use the language that your users use to describe you—not necessarily how you think about or describe your company. A good trick for this is to ask your users, "Say, how would you describe my company?" They'll typically tell you in a short phrase how they would describe it, and you want to take that exact phrase and use that as the language when reaching out to other customers.

I would even recommend putting that exact phrase right as the header on your website because the language that your users use to describe you is almost certainly the same language that's going to resonate with other people just like them. It's also important to remember you shouldn't make demands in these emails—"Respond to me by this date," or whatever. You're on their time, you're in their inbox, and it's not their responsibility to get back to you.

Finally, the last principle, number seven, here is to have a clear call to action. You want to end with a concrete next step: "Reply to let me know," "Click here to get started," "Can you intro me to Aaron," or whoever you're trying to get in touch with. This makes it really clear what action you want the user to take.

Then, it's really important to make this its own paragraph, its own standalone sentence right before you sign off at the end. Oftentimes, people will scan an email, get down to the end, and try to figure out what it is they're asking me to do—is this something that I could take care of right now in just a few seconds, or is this something that's going to take more time and effort, in which case I'm going to have to think about it and process it some more? By ending with a clear call to action, you're more likely to get somebody to take that next step.

All right, so these are the seven principles of effective email copy: have a focused specific goal, be human, personalize, keep it short, establish credibility, make sure it's all about the reader—not about you—and have a clear call to action. If you do all of these things, the good news is you'll be in the top 5% of all emails that are sent, and it's going to be hard for your recipients to ignore them.

But one email is often not enough. People are busy—they’re out on vacation, they get distracted. So you should plan to manually follow up two, three, four times as needed. Now, there's a fine line between being persistent and being annoying. You want to give it a few days between emails, and you can also get creative with each follow-up.

I've done this in the past: I was emailing somebody, and they weren't responding. I sent an email with the subject line "Free donuts." They opened that one, and I went and brought some donuts to their office to get them to talk to me. Sometimes you just got to get creative. If someone doesn't respond, don't get angry; don't get frustrated. Nobody owes you anything here. Just move on. You can check back in a couple of months—maybe it's not a problem for them right now; maybe it will be in the future.

All right, so let's see some examples. First, we're going to take a look at a couple of emails that are not effective and need some work, and we'll critique those. Then, we're going to take a look at a few emails that are actually really effective and point out some of the good parts of them. It's worth noting these are actually real emails that I have received, and I'm going to be reading them out of my inbox, but I'll be anonymizing some of the details to protect the innocent here.

All right, so the first one says, "Hi Aaron, hope all is well. I wanted to follow up because I noticed your order processing time could be faster. Our company plugs into your e-commerce platform to pull orders in real-time and guarantees all orders are fulfilled and on their way to your customer within one day or your money back."

The problem with this is that my company sold digital design assets that were downloadable from the internet. We did not ship physical products. So clearly, this is a company that's trying to sell me a shipment service, and because this is not targeted, we are never going to be their customer. This could have been the most amazingly written and personalized email, and nothing they could do would make me their customer because the targeting is not right. This illustrates the importance of having really strong targeting with your emails and why that will help you see much better conversion rates.

All right, this next one: "Hey there, hope you are doing great. I've just checked your website and your audience and content look interesting to us, so here's a quick question: do you partner with companies or collaborate somehow to make extra bucks? Best, in waiting for your reply. P.S. If you don't want to hear from me anymore, just let me know."

Okay, a lot of problems with this one. First, they didn't even have my name; it just says "Hey there." So they couldn't be bothered to personalize with my own name. Not a great start. There's nothing personalized in here: "Checked out your website; your audience looks interesting to us." And then, I think this is their ask: "Do you collaborate somehow to make extra bucks?" I don't even know what they're specifically asking for here. Finally, nobody actually signed their name to this email, and the P.S. says, "If you don't want to hear from me anymore, just let me know," which is basically telling me that this is spam. They've added me to some list, and now it's my responsibility to get off that list. So this is an example of an email that I could not delete fast enough.

Okay, here's the last one, which I almost instantly deleted: "Hi Aaron, my name is so and so from the Philippines. I saw your LinkedIn profile and took an educated guess in sending this email. You don't need to tell somebody how you found their contact information; that's relevant to you, not relevant to them. I'm a freelancer that offers contractual work to executives all around the globe. I have been helping companies since 2014. During my past jobs, I was able to facilitate good business relationships. I can help assist you in your sales team. I hope to share my skills and expertise with you."

You can see that this is all about the person who's sending it, not about the recipient at all. Basically, everything about this email is "I, I, I." It's all focused on the person who sent it, not on me, the recipient, and why I should reach back out to this person to work with them. This is an example of not focusing on the recipient. Make sure it's all focused on how you can help their problems—that's all they care about.

All right, now let's take a look at some good ones that actually worked well on me and converted. First one: subject line "Go Terps." This was a LinkedIn message, of which I respond to very few of them: "Hope you don't mind the cold reach out, but saw you also spent time in Van Munching Hall, so I went to the University of Maryland—the Maryland Terrapins, which we call the 'Terps.' I actually had a number of classes in Van Munching Hall on campus."

Right away, this is somebody that says to me they have context about where I went to school—they likely went there themselves. We have some uncommon commonalities together. "As a quick intro, my co-founder and I are both ex-Googlers working together on a meeting-driven task manager." So this tells me they're building some credibility: they've worked at Google in the past, making me think maybe they're solid engineers.

"I was hoping you might help out a fellow Terp and review my YC app. I've already had a few friends review, so it's been cleaned up significantly." This is really helpful because it tells me that they've done the work to get it to a point where they're not going to be wasting my time, and I'm going to be able to help them with the high-value things, not the obvious low-hanging fruit. "If you have a few moments, let me know the best email to send you the doc, and thanks in advance!"

This is a very clear call to action: "Share your email with me and I'll follow up with a doc that I can just leave some feedback in." So this was super effective; I responded to this person, which is something that I very rarely do.

Okay, now this next example is one that I actually wrote myself back when we were launching Creative Market, a marketplace for graphic design assets, and we were recruiting some designers to be our first sellers on the marketplace when we opened the doors. "Want to be one of the first Creative Market Sellers and start adding your stuff? We're just starting to open the doors for sellers to come in and add their content to be ready on day one of launch. Here's a special link to start setting up your shop."

"It's still super early in the rollout process for us, so I'd love any thoughts or feedback you have on how things are working right now. We're working hard to improve things every day, but definitely let me know if you run into any bugs, weirdness, or anything else you think we should know. Your feedback is super important to us."

"Oh, and please don't share any info or screenshots about the new site and the seller terms with anyone else just yet. We're inviting handpicked sellers only at this point, so trying to keep it super exclusive for now. Welcome to the club! Look forward to hearing your thoughts."

What's interesting about this email is this is entirely a templated email except for the person's first name and the special URL that they need to come and sign up early. But I used a lot of tricks throughout in order to make it feel very special and personalized. For one, a bunch of smiley faces makes it feel a little more informal. I write how I talk: "Oh, and please don't share any info," that sort of thing. I also use the word "special" and make it feel exclusive a lot: "Here's a special link," "It's super early for us," "I'd love your feedback," "We're working hard to make it better," "Don't share anything because, you know, we're inviting handpicked people only at this point. It's exclusive! Welcome to the club."

So it makes it feel very special for the recipient rather than something that I'm spamming out to everybody and hoping anyone responds to me.

Okay, and this last email is going to be a little bit different. We're going to do a before and after with a company that I worked with in the batch a few years back. They were a company that sold in-office smoothie machines and pre-made smoothies that they were trying to get startups and other companies to buy subscriptions with them.

They had this email they were sending out: "Hey, we're in the current YC batch hustling to achieve our demo day goal. Can you forward me to your office manager to chat about trying our delicious smoothies in the office for free in exchange for feedback to improve our product? We got Uber, Fitbit, GoPro, and others using us and thought your team would enjoy them too."

There's some good stuff in here: they've got the social proof that Uber, Fitbit, GoPro—those are logos that we recognize, so it makes it seem like they're more legit. But you know, it's all about them trying to get their demo day goal, and it doesn't seem as enticing for somebody to want to try to help them out. It's less clear what's in it for the recipient.

After brainstorming a bit and iterating on it, here's what we came up with working with the founders. The subject was "Smoothie Party—Current YC Company." "Hey, [first name], I'm Oliver, the founder of Snack Blends from the current YC batch, and I'd love to throw a free smoothie party for the whole company team at your office. It's like happy hour but smoothies and free! Are you interested? All we ask in return is for some feedback on the smoothies. Is there an afternoon I can come by to treat your team? Thanks!"

When they started doing this, one, it almost seemed like a no-brainer for their recipients. "Yeah, free smoothie party! Somebody's going to come and give smoothies to my team? Sounds great!" That helped get them in the door to be able to then sell those long-term deals.

All right, so I'm going to leave you with some final advice here. First, you should be doing this manually to learn and focus on scaling later. If you're trying to automate right out of the gate, you're doing it wrong. Instead, if closing customers by sending cold emails is an important part of your growth strategy, you should be blocking off hours per day to do this and do it incredibly well. It's worth it for the return.

Once you've got it working really well with you doing it personally, then you can try to figure out how to automate and scale the process more. To do that, you’ve got to be tracking and measuring. Remember that funnel—you've got to figure out at each step of the funnel: what’s the conversion rate? How can I improve it? Figure out where you're dropping off and focus on those areas.

You, the founders, should be sending these. People are going to take them way more seriously when it comes from the founders or the CEO, much more so than if it comes from some account executive or some intern or some other automated process that you set up here.

You should be sending dozens of emails per day. Block off the time and do the work to get it right, and you will see the results. You may be small, but that is your advantage because you can give your personalized attention to making these dedicated emails feel special to the recipient.

So personalize, be human, be persistent, and do the work.

So thanks for watching, and I hope this video helps you turn more of your cold emails into customers.

Thanks!
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