021: Making Cold Emails HOT with Alex Berman

Pete Mockaitis
Alex, thanks so much for appearing on the How to Be Awesome at Your Job podcast.

Alex Berman
Of course, Pete. Thanks for having me on.

Pete Mockaitis
Now, tell me. Your title is Chief Marketing Sumo. What does that mean, and how did you arrive at that title?

Alex Berman
I actually got it to troll Noah Kagan from AppSumo. I noticed that they had recently hired a Chief Marketing Sumo, so I figured I needed a title and I just came up with that one.

Pete Mockaitis
Oh, that’s cool. So tell us, what is InspireBeats all about? So you’ve generated $20 million in B2B sales or B2B leads this year. That sounds pretty impressive. What’s kind of the background story for how you got up and going here?

Alex Berman
Sure. Yeah. So InspireBeats does cold emailing for companies. So what that means is we basically make lists of leads and then send emails to pitch people on our company, to book sales or to book meetings. And yeah, it’s been a pretty fun ride so far. We’re about 20 employees now. We’ve been around for about two years.

Pete Mockaitis
Oh, that’s exciting and a quick rise. And so are you bootstrapped or VC funding in the mix?

Alex Berman
No. We’re fully bootstrapped.

Pete Mockaitis
Oh, that’s good. So that sounds like there’s some healthy cash flow going your way.

Pete Mockaitis
So now tell me. I think that some people might already bristle at that idea, like “Ugh. Cold emails and pitches,” like “Is that spammy?” Maybe you could set us straight or get reoriented on cold emails. The good, the bad, the ugly.

Alex Berman
Sure. And yeah, there’s a bunch of ways to use cold emails that aren’t spammy. I know most people, when they think about cold emails, they think about those SEO firms that send out three or four paragraphs of messaging that doesn’t make any sense, or for more of like a job seeker point of view, all those random recruiters that might be emailing you. But no, the cold emailing that I preach, I’m all about customizing the email per person. If you do mail merge, checking all the data first and basically making emails that are going to be… It’s going to basically be like you’re just a person and you met in that networking event versus where you’re just hard pitching people.

And cold emails, it’s not just for getting clients. I’ve used them personally to get partnerships. I moved to New York when I first graduated with no job, and got a job within two weeks using cold emails. So there’s a bunch of things you can use them for, and I hope that I’m able to remove some of that spammy connotation by the end of this.

Pete Mockaitis
Well, I mean, you cold emailed me. That’s how we ended up with this interview. And I found great value in what you had to say to me. And I appreciated it because I’m hunting and hustling, trying to get great guests with valuable content, and then you just appeared in my inbox. I said, “Oh. Well, that sounds great. Yes. Thank you.” So I appreciated it.

Alex Berman
Yeah. For sure. And so for context, I cold emailed Pete. The first line of the email was a compliment about the show. I actually went through, I looked through some of the episodes. I found one I liked and gave a quick compliment. And then the pitches for what we were going to talk about were customized for the show also. The rest of it was an email template. So that’s what I’m talking about when I’m talking about not just spamming random emails at people.

Pete Mockaitis
I hear you. And so, now, I guess in process, I’m thinking about this in terms of like a value chain or process flow here. When it comes to executing a cold email well, I guess there’s probably a research phase and then a phase associated with figuring out “What the heck is this person’s email address?” and then the messaging phase. So if it works for you, I’d love to maybe take some steps through each of these.

So tell me, first of all, what are some of the key places that you go to to research for the people that you’re reaching out to in the first place? I know you’re a big fan of conferences. So I think there are many different scenarios, but let’s just imagine I’m looking to form some partnerships or get some information from some people who can help me out so I have a clue and some expertise on a new project. Where would I start that research process?

Alex Berman
Sure. So conferences are a good spot. Mainly, it’s going to depend on who your target is. So for instance, if your target is web design firms, LinkedIn is a great place because they have tags. Basically, everyone that’s a web design firm on LinkedIn is tagged as that. So you can use LinkedIn Advanced Search or LinkedIn Sales Navigator to quickly find a list. And actually, LinkedIn is the number one place I would go for finding hiring managers, finding decision makers, and finding companies.

So first step: Figure out exactly who you want to target.As granular as director of marketing at a company with over 500 employees that’s been at the job for three months or less.You want to get as granular as you possibly can. That way, when we get to the cold emailing stage, you don’t have to customize the email as much.

Pete Mockaitis
Oh, that makes sense. Certainly. And so you’re telling me that within the LinkedIn Advanced Search or the Pro Find or Premium or something (I’m a premium user, but I haven’t used many of the features), I can specify all those fields with that level of specificity?

Alex Berman
So you can specify most things. Some things require just manual checking, but yeah, you can find job titles. You can sort by seniority. You can find industries, cities, all of that. And then what you’ll do once you have those criteria that you want is you’ll go out, open an Excel doc, and basically just start making a list of people, first names and last names, and then I like to just link to the LinkedIn profile as well.

Once you have that, you can start guessing the email addresses. There’s a few different ways you can do it, but other people have said it way better than I have. So if you just Google “how to guess an email address,” there’s over 500 or 600 articles outlining how to do that.

Pete Mockaitis
Oh my goodness.

Alex Berman
Yeah.

Pete Mockaitis
So, well, you tell me, since you’ve read all of them, or a reasonable segment, a slice of them. What are maybe some of the top three best practices you find yourself using the most often?

Alex Berman
Yeah. Sure. So for any startup, usually it’s just firstname@thedomainname.com.Three resources off the bat that you can use: There’s a Gmail plugin called Sidekick that basically what it will let you do is guess an email address, and if the email address is correct, it will show you the profile of the person. So what you can do is keep guessing email addresses. Firstname.lastname@, firstinitial.lastname@, until you find one that has a profile.

Pete Mockaitis
Okay.

Alex Berman
And then once you find one of those, then you know what the correct email address is.

Pete Mockaitis
Okay. Great. So we figured out a relevant name. We’ve used some tools to successfully guess the email address. So the two-line is populated. Well, now, this sounds like the hard part. I guess the next step is maybe the subject line. How do I kind of make that captivating so that it gets an open?

Alex Berman
What’s worked best is “Hi, first name. About company name/InspireBeats.” So “Hi, Mike. About Tyson and InspireBeats.” Very generic subject line, but that’s the one that’s worked best for us. When I was doing informational interviews for jobs, I just used “Hi, from Alex.” That one worked pretty well. Quick question works really well. You can get super specific with your subject line. So one that I was using to validate one of our products a few months ago was a subject line that said, “Hi, Brett. Built a tool that autofinds Ruby on Rails projects. Is that something you’d be interested in?” So that was a longer subject line, which makes each open more qualified, but it also might lead to a lower open rate. So you can do either way.

Pete Mockaitis
Okay. So it sounds like there’s no magic sauce in terms of “These are the magic words.” Like “free.” This probably even works against you.

Alex Berman
Some things to know when you’re doing your subject lines. Subject line, in my experience, most of the time, it will hurt you if you do it wrong. So that’s why I stick to the generic subject line. The thing that actually works the most for getting responses is going to be the next thing we talk about, which is the custom first line of the email. So yeah, I stick to a generic subject line, like “Hi, from Pete.”Or for you, I think it was “Hi, Pete. Room for another interview?” So just something that clearly articulated what the email was going to be about.

Pete Mockaitis
And that makes sense. And that’s actually a generous, friendly way to do it because as busy professionals, you know that’s handy because I could say, “Okay, I can delete that or I can go further,” which is kind of what a subject line should do for me. And so to recap, you said that formula you were using before was “Hi, name. About your company/my company”?

Alex Berman
Yeah. So that’s good for strategic partnerships. If you’re a job seeker, just “Hi, from your name.” So “Hi, from Pete” works, or “Quick question.”Those work great.

Pete Mockaitis
Okay. Lovely. Well, now, you got us all teed up. So what’s in the first line of the email body itself?

Alex Berman
Sure. So this is where your emails are going to stand apart from 99% to 100% of everyone else in their inbox. The first line is going to call out something specific that you like about their site or that you like about their career, basically something that you like about the target. So for instance, let’s talk strategic partnerships for a second. Let’s say you are a mobile development company and you’re trying to find other mobile app development companies to send you overflow work. So for them, you could go over to the mobile app company’s website, browse around, find a client that you like, and just say something like “Hey, Mike. Just found your website. Really impressed with the work you did for Hilton Hotels.” That’s something that’s very customizable right there.

Pete Mockaitis
Okay.

Alex Berman
If you’re reaching out for podcasts because you want to do podcast interviews, browse through the episodes. Maybe listen to the first five, six, seven minutes of an episode, or a whole episode, depending on how much time you have, and say “Hey, I really like the episode you did on interview skills.” So it’s something very specific there. And what that does is in Gmail, and in actually most mail apps, you’ll see the subject line and then you’ll see the first line of the email also as part of the preview.

Pete Mockaitis
That’s right. Yeah.

Alex Berman
So someone will glance at the subject line usually, and then they’ll glance at the first line of the email, and if it’s something like “Hi, my name is Mike. I’m a salesperson from XYZ Company,” they just won’t even open it. They’ll delete it, or worse, they’ll mark it as spam, which I’ve had a couple of domains that I’ve had to lose because early on I got marked as spam. So it’s not a good thing to go through.

Pete Mockaitis
I hear you. Well, that makes sense. So that conveys you are a human being. You have taken a look at something that I’ve done, or my company has done, and so it almost feels like “Okay, you have earned my attention,” as compared to someone who’s just blasting a thousand of these with less than seconds of preparation for each.

Alex Berman
Exactly.So I like to approach it similar to how you’d approach a cold call. If you were going to cold call somebody, you’re not going to cold call a thousand people at the exact same time, get them all on the line with each other, and do your pitch. You’re going to call each one, one by one. You might spend 30, 45 seconds, maybe five, six minutes looking at their website before you call them, or just browsing on it while you’re on the phone with them, and you’re going to customize your pitch for each person. So that’s why I recommend the next three to five minutes on each email, and approach it like you would a cold call.

Pete Mockaitis
All right. That’s great. So I got the subject, the opening line. And what’s next?

Alex Berman
Sure. So then you go into your pitch. I like to keep emails in general about five sentences, sometimes shorter. So your pitch should convey very easily who you are and what you want from them. So let’s go back to the strategic partnership example. After you do that custom first line, then you can say something like “Hey, my name is Pete. I run a podcast about being awesome at your job. We’re looking for new guests.” That’s a simple enough pitch. Or “My name is Mike. I’m the founder of a mobile app development agency. We help enterprise companies develop their mobile apps.” So a very short sentence like that that introduces who you are.

Then you do the ask. So “I’m looking for new strategic partnerships, and your agency seems like a very good fit for finding projects.” Or “I’m looking for new interview subjects, and your background looks super interesting.” Then after that, you go and do the ask. So all emails I like to end with a question mark. You never want to send a cold email without a question. I like to make it as easy as possible for somebody who’s busy to say yes or no, so I like to have it be a yes or no question. My favorite is “Does that sound like something you’d be interested in? If so, I can send over a couple of times for a call.”

What’s worked for me a lot when I was first starting out freelancing was meeting people for coffee because all of my targets basically was in New York already, so all my targets were based in New York. So I could be like… I used to say, “If so, I would love to grab coffee. Does that sound like something you’d be interested in? I’ll send over a couple of times. Otherwise, happy to hop on the phone or just send questions over email.”

Pete Mockaitis
Mm-hm. I like that, too, because that further conveys you’re a human being and you’re willing to invest some genuine time associated with travel and whatnot to get out there and do coffee. So I like that. And so I’m curious. Do most people say, “Let’s just do phone”?

Alex Berman
Most people, when I was looking for a job, I’d say most of them said, “Send me the questions via email.” After I asked a couple of really good questions, then they would hop on the phone. A few people, though, loved the coffee. One startup founder I got an internship with within 30 minutes of meeting him because of the coffee. The other one was the one who actually offered me a job after a 30-day trial, and that was from one coffee. And then the third one is actually the Chief Marketing Officer at this startup called Betterment. They’ve raised about $250 million, but back then they were just a team of eight. And he introduced me to a bunch of people that ran like WeWork Labs.

So everyone that decided to meet in person was super high value. Most people, they’ll say, “Send the questions.” But it’s worth just sending more and more emails because there are a certain percentage of people that want to give back and will meet in person.

Pete Mockaitis
I like that. So can you tell us then? I’m thinking about data now, and I’m sure open rates, response rates, close rates, whatever, very wildly. But could you maybe give us a sense for what kind of ranges of numbers would you consider bad versus good, and how do you go about tracking that? Are there tools, software, or spreadsheets? Or what could you do?

Alex Berman
Yeah. So my favorite tool right now for tracking is Streak CRM. I think it’s like $10. And then I used to use Yesware a lot, too, but now it’s paid, and I don’t find enough value in it to pay for it.

Pete Mockaitis
All right.

Alex Berman
So Streak is the one that I like the best. Good open rate. If you could get 80% to 100% open rate, that’s perfect. Just use some of the subject lines that we just talked about. You’ll be able to hit that pretty easily. The only number I really like, though, is meeting book rate, which is how many qualified people are returning your requests and actually meeting. We’re able to hit consistently about 2% to 3% from most clients. Sometimes, it’s higher than that, 6%, 7%, 8%, on scales up to like 1000 to 2000 emails a month. So I’d say that is good if all you’re doing is sending cold emails all day. For instance, you’re a job seeker and you have eight hours a day to put into the job search, and you can customize your emails, I’d say if you could get a 20%, 30% response rate from customizing your email, that’s really good.

Pete Mockaitis
Okay. That’s helpful. So that tells me that if my open rate is 50%, you’re doing something wrong.

Alex Berman
Yeah. And I would check your subject line. But if you’re using some of the subjects that we already used, I would check your first line of the email and see if you’re starting with something like “I am” versus a compliment.

Pete Mockaitis
Mm-hm. And the Streak CRM that also you could input right there “Hey, what happened with regard to the follow up?”

Alex Berman
Yeah. So it’s a CRM. So basically, it lives inside of Gmail, and you can run a funnel where basically you can put them on, open the deal, negotiating, closed, and basically track where they are. And there’s notes and everything in there as well. It also has a mail merge built in for sending cold emails in bulk.

Pete Mockaitis
Oh, that’s great.

Alex Berman
Yeah.

Pete Mockaitis
That’s great. And so talk to me a little bit about… And I don’t imagine most folks are going to be going so hardcore with so many messages that they get their domain in trouble, but what are some of just sort of basic things we’ve got to watch out for when it comes to deliverability? So making sure you don’t land in spam or junk, which are actually different in some places. What are some things to bear in mind there in terms of like message sending velocity or no-no-no keywords? We’re not going to talk about Viagra, I know, or Cialis. But what are some no-no’s, just to make sure that basic technological delivery is happening?

Alex Berman
Yeah. And I actually just recorded a YouTube video on this. It’s going to go live on Monday. But basically, there are a couple of things to watch out for. If you customize your email, it shouldn’t be an issue. If you’re sending too many emails at once, Google will flag you. So if you’re going to send bulk emails using a mail merge, use something like Streak.

Or another one is QuickMail.io. And what they do is let’s say you have 100 emails queued. They’ll send one every 30 seconds rather than sending them all at once. So it looks to Google like you’re sending them manually. Also, if you’re using a mail merge, something like ToutApp, make sure you send through your Gmail servers rather than Tout’s servers. Don’t use something like MailChimp. Don’t use html in your emails, and make it seem like it’s you writing to them. All of that is going to remove the likelihood that it’s going to be spam. I can keep going.

Pete Mockaitis
Please do.

Alex Berman
Another thing is you want to make sure your profile is tied to a real LinkedIn profile. For that reason, I don’t recommend creating a domain just for cold emailing. Use your main domain and tie it to a LinkedIn. People are less likely to mark it spam if there’s an actual person tied to it.

Pete Mockaitis
And so the tying just sort of happens in the background of companies sharing data as opposed to actually you could make a linkage between my pete@awesomeatyourjob.com, which is on my LinkedIn and my Gmail?

Alex Berman
Oh. So when I say Gmail, I’m talking Google Apps for business. Basically, you can use Google to use a custom domain.

Pete Mockaitis
Oh, yes. And that’s what I’m using there. But if you say tied in, is there something I need to say, like “Hey, Gmail. Here’s my LinkedIn.” Or Gmail is like, “Yeah. We know. We know everything about you.”

Alex Berman
It’s actually in the LinkedIn settings. You can add, I think it’s unlimited emails to LinkedIn, and basically they’ll associate it with your profile. And that way, if someone is using Rapportive, which is a Gmail plugin, or if someone is using Sidekick, which is the plugin we talked about, your profile is going to pop up when they mouse over your email address.

Pete Mockaitis
Okay. Got you. Well, this is thorough and beautiful and exciting. I’m looking to maybe adjust the way I’m reaching out to potential guests based on this. So this is edifying for me. And this is kind of rapid fire tactical goodies, which is kind of fun. So you tell me, before we maybe have to shift gears into the fast faves, is there any other key stuff that you think folks seeking to be more awesome at their job should know when it comes to the cold email research, crafting, delivery process?

Alex Berman
So key things. Basically, you’re going to have to send a lot more than you think are necessary. Rather than sending four or five, which is what a lot of people start out with, I recommend just taking time sending 50, if you can, just 10x-ing it.That way, you’ll start getting positive feedback. If you only send five or six cold emails, you’ll run the risk of having one person respond “Not interested,” and it will kill your vibe sometimes for the rest of your life. You just will never send cold emails again.

Pete Mockaitis
Oh, you’re doomed?!

Alex Berman
Yeah.

Pete Mockaitis
Bummer. Okay. So that’s great. So more than you think you need. Anything else?

Alex Berman
I’m going to hit the customization note again. Don’t think that you can just send a template out and have it be enough. Even if you write the perfect email template, every person that you send to, the language is just going to be slightly different, and they can get a read when they see your email. So the more valuable your product is to them, the less custom you can make it. But when you’re just starting out or you’re doing sponsorships, I would take the time and customize as much as possible.

Pete Mockaitis
Perfect. All right. Well, thank you, Alex. These are some good nuggets. Absolutely. So I’d now love to shift gears a bit into the fast faves. Can you start us off by telling, is there a favorite quote you have that inspires you again and again?

Alex Berman
Sure. It’s not really a quote per se because I don’t remember the exact words of it, but Zach Galifianakis. He was an actor in The Hangover. He also makes movies and shows and all this. He was on, I think it was the Nerdist Podcast. It might have been “You Made It Weird.”But he was talking about how the first take of a project, or the first draft, is usually the best. And it’s not really worth spending hours perfecting language or really like editing too hard just to get that extra 5% benefit. He was pretty much talking about how he rushes things out. And I really like that way of looking at things. Some people have spent hours or days on a blog post or on a project when the first draft is usually good enough. You just need to read it through maybe and change a couple of sentences.

Pete Mockaitis
All right. And how about a favorite study or a piece of research?

Alex Berman
They might have a common theme to them, but my favorite piece of research is the Pratfall effect. Have you heard of that one?

Pete Mockaitis
I sure haven’t. Please, enlighten us.

Alex Berman
Sure. So the Pratfall effect basically says the more you mess up in a professional context, so the more human or the more foibles you have, the more people like you and trust you.So for instance, if you’re in sales and you open the call by talking about how you love playing Xbox or you just saw The Avengers or you lose the professionalism at some point in the interview, that actually, according to the Pratfall effect, makes the salespeople trust you even more.

Pete Mockaitis
Oh, that’s fun and effective at the same time.

Alex Berman
Yeah.

Pete Mockaitis
How about a favorite book?

Alex Berman
Favorite book. The one that came to mind was “Call Me Ted” by Ted Turner. It’s basically about his rise as the founder of TBS, Turner Classic Movies. And he was also one of the first individual entrepreneurs to launch a satellite into space, which I thought was really cool. So I really like that one, “Call Me Ted” by Ted Turner.

Pete Mockaitis
And how about a favorite website or blog podcast?

Alex Berman
Sure. So I’ve been spending a long time on YouTube. The last three months, I’ve been trying to master YouTube for marketing. I’m up to about 500 subs right now. So I’ve been studying all these big YouTubers. My two favorite right now: Grant Cardone talks a lot about sales and he talks about motivation on B2B. I really like him. The other YouTuber, Gary Vaynerchuk recently has been crushing it with one of his books.

Pete Mockaitis
It’s what he does.

Alex Berman
Yeah. On YouTube, and making all these super motivational videos. Podcasts. I’m a big fan of Kevin Smith’s SModcast. It’s not really a business podcast. It’s more of entertainment podcast, but it’s good after a long day to just get some distraction. And then also, “You Made It Weird” with Pete Holmes. They’re like four or five hours long of him just interviewing celebrities, and they go into these super deep mental exercises and talk about philosophy and psychology and all these things. And sometimes I just wander around on weekends and listen for like four hours at a time.

Pete Mockaitis
Oh, that’s fun.

Alex Berman
Yeah.

Pete Mockaitis
And how about a favorite habit or personal practice you find very effective?

Alex Berman
Sure. Yeah. So the biggest game changer for me was keeping a day by day to-do list just in a TextEdit file that’s always on my desktop and always open in the right corner of my screen. So I’m looking at my laptop right now. I dedicate, it looks like about 10% of my screen at all times to this to-do list. And it’s just a TextEdit file. I haven’t had too much luck using Todoist or any of those apps, but just knowing what my goals are for the week and then knowing the tasks I have to do every day has been super helpful.

Pete Mockaitis
And a favorite time-saving trick in addition to the to-do list? Or is that the mother of tricks?

Alex Berman
So now the mother of tricks is your gut instinct is usually right.

Pete Mockaitis
Well, that will save you that time.

Alex Berman
Yeah.

Pete Mockaitis
As per the Prat something.

Alex Berman
Pratfall effect.

Pete Mockaitis
Pratfall.

Alex Berman
Yeah. So I found that your gut instinct is pretty much correct. Let’s say you’re talking to a potential client and you have just a feeling that they’re going to be bad to work with. Most likely, it’s going to end up poorly. The opposite is also true. Let’s say you’re talking to a potential new boss and he seems like a really cool guy off the bat. Usually, that’s going to turn into something good. So I’ve learned to just start going with my gut a lot more.

Pete Mockaitis
And how about a favorite truth bomb? If you are doing more YouTube-ing and podcast appearances, you’re building a bit of a content library or arsenal. What sort of stuff are you sharing that you find it really gets people nodding, taking notes, retweeting?

Alex Berman
You listen to my Rocketship.fm one. I know you called that out over the email. And the thing that they quoted over there was the only number that matters when cold emailing is the meeting book rate. So not open rate, response rate, or anything like that. Also, I think the quality of leads beats content of the email in terms of importance. So if you have a high enough quality lead, you can basically email them one- or two-sentence quick tips and get some kind of response, versus if you email everybody on LinkedIn a super targeted email but they’re not interested, you’re never going to get anywhere. So those are the two.

Pete Mockaitis
And how about best way to find you? If folks want to learn more about you and your stuff, how should they get in touch?

Alex Berman
Sure. Yeah. If you need B2B leads or you need help with outreach or anything like that, we’re on inspirebeats.com. And then if you want to watch more YouTube videos, tutorials on B2B selling, interviews with people like Aaron Ross, Neville Medhora, check out youtube.com/alxberman, with no E, so A-L-X-B-E-R-M-A-N.

Pete Mockaitis
All right. And a final, perhaps, challenge or a call to action to leave listeners with?

Alex Berman
Sure. So say you’re at a job. What I want you to do is brainstorm 10 ways the company can improve, and then list out three deliverables you could personally produce for each one of those ways, and then I want you to email it to your boss’ boss by Friday, by this week.

Pete Mockaitis
Well, that is bold.

Alex Berman
I know. Last time I did that, I ended up as director of marketing at that company.

Pete Mockaitis
That’s fantastic. Well, Alex, it’s been a lot of fun. Thank you so much, and I wish you and InspireBeats all the best of luck as you continue to grow.

Alex Berman
Sounds good, Pete. Yeah. Thanks for having me on.