It’s not so complicated: Cold email as a channel for startups

Rui Bom: Hi. My name is Rui Bom. I’m originally from Portugal. But I’ve been in Asia living in Asia since early 2007. I was in China first, that I moved to the Philippines, Indonesia. Now I’ve been in Japan for the last four years. From a professional standpoint, I have, I feel a pretty interesting background because I have a good mix of multinational company and startup company experience. I used to work for a big consumer goods company back in Portugal, where I’m from, and in China. But then in 2012, I decided to leave the corporate world to set up my company, I had a co founder, the online travel technology company, we raised a bunch of money from big investors in Europe. But then in 2017, I basically had some issues with with my co-founders, and I decided to leave and I became more of a startup consultant and mentor. So I’ve been doing this for about five years. And since late 2021, I’ve basically gone full time in basically all lean into mentoring, and I’ve been doing mentoring, mentoring full time for for more than a year now.

Spyros Tsoukalas: Welcome, Rui, Your reputation precedes you. So I’m excited to chat with you about cold email as a channel for startups. So let’s hit it right away. Tell us something, please, that we didn’t know about cold email nowadays.

Rui Bom: So I mean, first of all, thanks for for inviting me, as, as a member of the community, I’m happy to be here. Cold email is actually one of those things that I find quite interesting. And I get a lot of people to ask me about it. Because everybody thinks that they know how to send emails. Because I mean, we’ve been doing that. And pretty much everybody’s been doing that for years and years. But the truth is that I would say probably 99% of the emails we send and receive are not getting anything in terms of output, right? So we send emails, because we want to get something out of those. And the truth is that most people get nothing. Of course, if we talk about sales, emails, they get nothing out of it. So I think there’s probably three or four things. insights that I got out of studying this topic that I think most people are not aware of. One is that the vast majority of people spends more time emailing, than this they spend sleeping. So in average, people will spend about 20 weeks a year receiving a reading and sending emails. So that’s that’s actually more time than then we spend in bed. The other thing that I find is very interesting, and most people don’t realise this is more than 80% of people read emails on their mobile devices. And this has a huge impact on first how they read the email, and how much they read. Right? So imagine you’re getting emails on your iPhone, you’re opening the mail app. And what you’re going to see is a name, a subject line, and a two line preview. And based on that you actually decide whether you want to open the email or not. It’s a completely different experience from, you know, reading the email on a laptop, so most people don’t think about it when they create an email. The second thing that most people don’t realise is the attention span of a person is about eight seconds. And this basically means people don’t have time to read your emails, they actually scan your emails. And so the question becomes, how do you make sure within those first eight seconds, people are able to focus on the parts of the email that increase your chances of actually getting the desired outcome out of those emails? Right. So those are kind of two or three important insights. I mean, if I probably could add one more, I think most people think of a cold email as a way to sell something. In my view, a cold email is a way for you to start the conversation. And the reason for this because we know I think is about 85% of people don’t get a positive response to their email, unless they follow up four times. So which basically means that if you give up on your first email, because you thought the purpose of that email was to sell something, you’re probably wrong. And so the first email first cold email should be seen more as a way for you to start the conversation that we know is probably going to unfold over you know, 3, 4, 5, 6 follow up emails. So I’ll say there’s probably four insights that most people don’t seem to be aware of.

Spyros Tsoukalas: These are mind blowing. So let’s say that somebody becomes aware of these facts, what’s next for them, like, what should they just start applying this kind of learnings or like who is they cold email for, like post should be paying attention to it.

Rui Bom: So if you think if you think about, and we call it cold email, but you could actually just call it email, right? Think of think of as much as 20, 20 weeks a year spent on email. And I think out of these, if I’m not, I don’t have the numbers in front of you right now. But I think about the average person receives or sends and receives about 120 business emails a day, right, and the business email is supposed is being sent, because the sender is trying to get something out of it. So I mean, think about, you know, investors, partnerships, media, people trying to hire, sales prospects, right, the way for you to communicate with these people is through, doesn’t need an email, a message, a LinkedIn request. But at the end of the day, it’s about you know, communicating with someone. And what you want out of it is to get them to react and act, depending on of course, what your desired output or outcome is. Now, two things. And I’m going to use two quotes that I love that I think, helped to understand why having these insights and acting on these insights is important. First, you don’t rise to the level of your ambitions, you fail to the level of your systems, what this basically means everybody wants to put together amazing emails and be successful. So what distinguishes the different people is not the level of their ambitions, but whether they have a system that allows them to be successful. And that’s kind of the I’m going to explain a bit what the system is for me. But so this is important thing to bear in mind. The second thing is every system is perfectly designed to achieve the results it is achieving, which means if you’re employing a system, and the system is bad, you’re gonna get that results. If you have a system that is a bit more sophisticated, you might get better results. And so it’s really important that we start thinking about emailing as employing a system that has been created and tested. The one I use is called 3R framework. 3R standing for Relevance, Reward, and Request. And so if you ask me who is this for this is pretty much for anybody who needs to send out the message. And again, it could be, as mentioned, leaving a cold call to be an email could be an SMS or WhatsApp message, LinkedIn requests, a dating app message, I mean, whatever kind of communication you have, having the system that has been tested and validated, he’s going to help you get more a lot more out of it.

Spyros Tsoukalas: Makes total sense. I have actually been through your blog and read about it. So I have been being I have, I have been spending some time in cold email, in email in general recently. So what I realise is that there is a huge list of things that people should be paying attention, before or after the message per se, as you mentioned, like with the your, the framework you just highlighted. So there is an indicator of a list of problems or things that should be taken care of like warming up not going to spam, open rates, subject, CTAs, like how many follow ups? So how does someone define a process a process around this huge list of stuff that should be taken into account? And like what would then very brief like very few steps that you would highlight to people that are interested in to getting started with email.

Rui Bom: So I think, as mentioned, there’s there’s a lot of stuff online, everybody’s giving you advice. And I think for the most part, the advice is in line with with the one that I’m going to share here, I think the problem mostly is sometimes not organised in a very concise manner. And so what I’m trying to do here is basically go through the three or four things that I think you need to pay a lot of attention to, if you’re going to beat, you know, or if you’re going to basically crack and hack the mail game. So the first one as much as the system, right? So the system is what I call 3R, Relevance, Rewards, Requests. What does this mean? In a nutshell, Relevance is about you explaining right away to the reader, why is it that you’re getting in touch? The reason why this is so important? Because if you can see that you’re opening most of your emails or people open most of their emails on a mobile device, the thing that they’re going to see before they click the email is the first two lines or three lines, right? The preview, unless you tell the person why is it that you’re getting in touch with them, it’s very likely that the reader is going to basically these miss the email or delete it, right? So you want to make sure that the first two lines of the email, rather than saying Oh, my name is X and I’m the CEO of this company, and here’s what we do. You know, all that is basically a bunch of BS, you need to go straight to the point and tell the person why is it that you’re getting in touch with them? Now, how do you do this? For the most part, the way I like to do it is maybe research the website, go on YouTube, try to find something that allows me to create a good reason for getting in touch with people So for example, oh no, I saw you’re hiring a UX designer. My company basically specialises in hiring remote people, maybe I can help. So being very relevant. The second part is Rewards. Most people, and I guess it’s just a human, normal or normal predict predictable human behaviour is most people ask, before they give. And so the idea here is, can you give something to the reader that allows he or she to experience your product, ideally, for free? Before you actually ask for something in return. So an idea here might be a list, you know, I, I know you’re hiring a UX designer, I’ve actually just interviewed four people, great people this week. I’m attaching the interview notes and resumes in case you want to take a look. So I’m already providing value to you so that you can see that I can actually help you hire people, without me even asking you for something in return. Okay, so this is the reward. The third and last R is Request. What is it that you’re going to ask this person to do? Now, the big mistake that I’d say 99% of people do is most of the times the request on the first email is, you know, would you have, you know, 20-30 minutes for a call next week. The problem with this is that if you’re sending an email to somebody that doesn’t know you, and you’re already asking this person to jump on a call with you, it feels a bit too intrusive, right? So the idea is, can you find something that is more of a soft request on the first email to increase your chances of the person actually acting on it. So an idea here might be instead of you asking for a phone call, or a meeting, maybe you want to say, Listen, I’m gonna have a webinar tomorrow, five people are going to come to the webinar to interview this candidate, you know, if you’d like to join, here’s the link. So the person doesn’t need to join, it’s not as intrusive, but you’re still requesting something for the person to do. Okay. So this is, again, very, very oversimplified. But this is what the 3R system means, Relevance, Reward, Request. The second thing that is super important is the subject line, right? Most people don’t think about the subject line. But again, if most people are receiving emails and reading emails, on a mobile phone, there’s three things they see your name, the subject line, and the two line preview. We know from statistics that are available and experienced that 34% of people actually open the email based on the subject line. So if your subject line is good and straight to the point, that increases, massively increase the chances of people actually opening the email. Now, there’s a lot of things that we go through in terms of how you should grab the subject line, I’m not going to go into that right now. I mean, for people who are interested, you can, as you mentioned, go to my blog, or follow my LinkedIn posts, I write a lot about that. So subject line is super, super, super important. The third thing to bear in mind, as mentioned before, is very few people get anything out of a first email. So one of the most important skills for anybody who’s using cold messaging is patience. You need to be an, of course, and being able to suffer. And the reason why this is important is because 80% of people say no, four times before they say yes. Meaning that unless you spend a lot of time following up with these people, you’re not going to get the yes that you need. The problem is that at the same time that 80% of people only say Yes, after four emails, 92% of us actually give up give up before email number four, so most people are not getting anything out of their cold messaging strategy, because they just give up too early. Okay, so follow up is extremely important. And the idea behind follow up is that, of course, you keep using the 3R system in every single email, because this is the system that again, is going to output, our likely output more value. Now, the last thing that is super important is tracking, you need to find a way to send your emails through some sort of piece of software or tool that allows you to track, number one will open the email. Second, read the email. Third, reply to the email. Why is this important? Because if you need to send a follow up email to someone who didn’t read the email, or you need to set up, send a follow up email to someone read the email, the body of the email needs to be completely different. And unless you track it, you will never know it. Okay, so just to recap, use the system. Think about the subject line. Don’t give up too early, you need to follow up at least four times to get something out of it in average, and make sure you’re tracking what’s happening to your emails, because that should determine the way you follow up with your prospects.

Spyros Tsoukalas: Amazing. Amazing. Thank you very much for getting in so many details. Before we wrap it up. Would you like to list the favourite tools that come in your mind like your favourite tools around emailing?

Rui Bom: Yep, absolutely happy to do that. So I and I don’t use all of these tools. I mean, I’ve seen them before. I try to keep things simple but out they probably the five tools that you want to take a look at are, number one, Hunter.io, which is basically a MailChimp type of automation software. The reason I use this because I kind of know for some reason I prefer the the interface where the ID is you build, you know, you import your, your, your email list, and you basically create the message, automate the message, and then it allows you to track know who opened will open as templates. So it’s kind of a one stop shop, I would say, for email automation. The second one is Mailcharts. Mailcharts is a website where you can from where you can get a lot of industry insights, like what kind of keywords work best for certain industries, what kind of call to action should you have. So it’s kind of industry slash business related. So I think you know, because all our businesses are different. Taking a look at this might give you some insights that you currently don’t have in terms of how to communicate with those specific people within those industries are those targets. The third one, Hemingway App is basically artificial intelligence is an AI tool that helps you write more impactful emails, I have kind of because I use the 3R system, I kind of have already my no my favourite templates, so I don’t really use AI too much. But for someone who’s starting May, you can get some ideas out of that. Fourth one, a website called Really Good Emails. So it gives you a bunch of best practices and templates. So if you want to get inspired, that’s a good website to, to go to and and check out. And then last but not least, it’s especially when you get into the automation and people with big email databases, you want to make sure that you clean your list as much as possible to avoid, you know, fake fake emails and emails that don’t exist anymore. It’s called Neverbounce. So basically allows you to clean your emails list to make sure that you don’t get the most to bounce. So those are kind of the five tools. And again, if you go, if you will, you’re going to find a lot more. But given the fact that I like to keep things simple, these are probably the four or five that I would suggest everybody to check.

Spyros Tsoukalas: I’m impressed as I know, one out of five. So I’m impressed and I will start taking them soon. So Rui, thank you very much for your time and your amazing insights. I hope you enjoyed this recording like in this discussion as much as I did. And yeah, I would encourage people to read The Unicorn Playbook and look for you on Growth Mentor.