Cold Emailing Will Change Your Life

Something, I think it was Cody, that you said on a call, uh, one of our Enjoy Basketball team calls from a few months back. You said cold emailing is my favorite thing to do. You said you never know who you could meet when you cold email someone. And I have, it's like rattled in my brain since then. And I realized like, I don't think like that. I don't think of like, oh, oh my God, should I be spending hours DMing people, cold emailing people every day? I just want to talk about that because It's a, it's a mindset shift that has obviously like played into your guys' success and I wanna know like what you think about just the constant outreach.

Sure.

So I mean, for me personally, I've been trying to cold email people for over a decade in my quote unquote working career. And the reason why I continue to do it is cuz it's paid off, you know, immensely for me. I, everything from like my first internship was through cold emailing. My background is I'm a lawyer and. When I thought I was gonna go down the path of practicing in LA in entertainment, I met like 125 lawyers over the course of a few years because I was like, I need to know everything that's going on so that I can prepare myself to do that once I graduated from law school.

Who gave you kind of like the, the impetus or like the boost to do that? Is that just like, cuz when most people think of cold emails, they like would break out in hives and they like, this is not something I'm going to do. So like where, Sounds like you've been doing this for a really long time. Like, where did that kind of start?

It's funny. I think that, you know, Cole and I are entrepreneurs, but like, we were never your, like, typical necessarily, like, oh, we're trading baseball cards and lemonade stands. Like, there were things here and there, obviously, when we were growing up. But I think this was kind of my version of that, if that makes sense. Like, this was where I was proactive and trying to hustle and meet people and connect. Which is a little different from the quote unquote conventional wisdom that you hear from people growing up. So I just felt it was inherent. If I was gonna be successful in doing that, I needed to just know everything about the industry. I needed to know who the players were. I needed to keep up and, you know, read the news so that if I was presented with a situation or a problem, I could just act accordingly. And then you fast forward to today. It's funny, Cole and I spent a week in LA last week 3 or 4 of our meetings were from cold emails and they were to very high-level executives in the sports media world. And like, it was just a shot in the dark. And like, if we get it, we get it. If not, it's all good. Like, there's nothing to lose by reaching out and trying to connect with someone. And if you can, you know, provide value back to them, you know, it's a no-brainer. It's a win-win. And today with, you know, the age of Zoom, It's like, okay, you can get on a 15-minute Zoom call. Like, it's not really going to kill you. You don't have to go to the coffee shop.

Yeah, it reminds me one of the things that my parents told me when I was, when I was in high school is that you don't get to be the one that tells yourself no. So whether that is like cold outreach to something or applying to a school or asking a girl out that like you don't be able to be like, oh, she's not going to go out with me or this person is not going to take my calls. Like, you don't get to tell yourself no. It's the other person's job to tell you no. It's your job to ask.

Yeah, there's, there's nothing to lose. Like there's literally nothing to lose by sending a cold email. And like similar to Cody, like sending cold emails literally changed the entire trajectory of like my early career. Before we even started Up North, I worked in the music industry. I didn't know anybody. And so when I was coming out of college or in college, like I literally carved out probably 2 hours per day just making a list of, of different executives and people I wanted to meet and just cold emailing., and it worked. I mean, not everything's going to hit, but that's the game that you play.

So I want to go back to the cold email part for a second, because like my mind is still spinning on that. Uh, it's like I said, it is something that not too many creators would think of doing naturally, or they just get like worked up about it. Besides thinking, oh, this person is going to say no, that's maybe a limiting belief that needs to be eliminated instead. So what kind of goes into a cold email for you guys? Like from, maybe it's not like specific phrasing, but just how, how do you make it, how do you make it a win-win or how do you drive, how do you drive that value and make it interesting enough? Because I think people will, besides telling themselves it's not going to work, they're telling themselves the reason it's not going to work is because I'm not going to, I'm not going to do it the right way. And so it's just, I'm going to look, I'm going to look bad. Not only now this person will know who I am and that I can't write cold emails.

Okay. Overall, less is more. That's how I approach all cold emails. Less is more. Nobody's trying to read, you know, 4 or 5 paragraphs of text. Um, I start with a really quick intro, uh, you know, a one-liner, here's who I am. And then the next part, um, I try to sort of establish some somewhat credibility, you know, hey, we're building this brand and we've achieved X, Y, and Z in a matter of a year or two. Um, next is the ask. Keep it straight to the point. What exactly are you looking for? I think sort of playing into, you know, showing your admiration for the person that you're trying to reach out to or why you are looking to connect or how you appreciate something, whether it's a business that they're building, a project they've worked on, that's kind of it. And then like sort of what is the ask? Hey, let me know if you're available. Is it coffee? Is it a 10, 15-minute Zoom? Cody, you know, if you have any other things that you put into the cold old emails?

Yeah, I would say like maybe the order changes in terms of those points that you hit on, but relatively, I mean, you, you hit basically all the points. I would say shorter is better. I think people overlook, um, and overestimate the subject line. I don't think it needs to be so complicated. Again, simpler, I think the better. Um, you know, sometimes if you're asking something more complicated, it comes off salesy. So I feel like people aren't as inclined to maybe open it. So I would refrain from doing that and make it, try to make it as simple as possible. But like even to this day, we've sent thousands of cold emails. Like Cole and I still go back and forth with each other on the semantics and, you know, the inner workings of, okay, what if we use this word or that word, or if we phrased it like this? But yeah, I think trying to provide some sort of value prop compliment, but compliment in a unique way, make it personal if you can, try to have some tie to that individual in some capacity.

I'm also going to add one more thing and we can't say who it is now, but just for the sake of this conversation and this topic, Cody and I've been trying to connect with exec in the sports media space for 2+ years. There's some mutual connections. There's some requests for intros that have been made. Nothing came to fruition. We decided screw it 2 weeks ago. We're going to send a cold email. And boom, we got the meeting. So like, I just want that to speak towards our point here of why cold emails are so important and how there's like truly nothing to lose.

One of our friends, people that we work with through like Hey Creator and Good People Digital, her name is Amanda Goetz, and she said that she, she cold DMs like one person a day that she wants to connect with. And she's like, you wouldn't believe the number of people that I've been able to connect with just because I'm like, I'm consistently like taking those swings. I'm stepping up to the plate and just going for it and making the ask. So I think it's a valuable thing, whether it's like partnerships or like people that you want to connect with. It could be any number of things for like these more like digital creators who are in the pro— that are in like the course space. That's a lot of who, like a lot of our listeners, but it's still something that like there are definitely people out there that you want to connect with. And I think just following that like simple framework can, could be like a huge win.

It's really really funny that you say like the one DM a day and like DM specifically, not email. I'm pretty sure I DM'd Cody first and was like, hey, like, just if you have any short-form video needs or anything, like, big basketball guy here, let's see if we can make something happen. That's like, I'm not gonna lie, that might be the only cold DM I've sent to someone I wanted to work with.

If you get a follow from someone that you're interested in, auto cold DM like you have. I mean, it's not even that cold. At that point. Like, as fresh as possible, get in there.