He Runs Paid Media at Cursor - Here's What Most Growth Leaders Get Wrong (Rex Gelb)

Speaker A: Foreign Excited to share with you my conversation with Rex Gelb. Rex is a performance marketing expert. He both runs Summit Chase, which is a paid media agency. And the performance marketing team at Cursor is excited to have him on the show because well one, he spent hundreds of millions of dollars on ads. He's also scaled teams from being a solo operator to having dozens of people. And he's seen what breaks down when as an A player you stop being the person doing all the work and you start leading and delegating to other people who are doing the work. So we got into all that stuff, we got into all the learnings and the lessons and the stories from his leadership journey from what to do when you sure you've made the right call and then your leadership team isn't on the same page and doesn't agree and how you handle that. We talked about the moment as a player coach when you have to really let go and become a real manager and a better delegator and some of the process and sops that help that. And we talked about how to take tough feedback when your heart's pounding and you're in the room and you don't wanna fire back and wanna take a little bit of a breath. So if you're a growth marketer or you're a growth leader and you're trying to scale yourself out of being the a player involved in every meeting and every decision, you're gonna love this conversation. It's enough from me. Let's go ahead and hear from Rex.

Speaker B: First job outta college. I interviewed at a very, very wide range of companies, mostly at like big brand companies just cause that's what I thought you were supposed to do like IBM, Intuit, pa, paytech, Luminex. Companies I had heard of got a decent amount of offers from those big companies. But then I remember having a conversation with my dad and he was like, if you're confident in your abilities, you might be better off going to a small, scrappy, fast moving startup. And instead of trying to climb the corporate ladder, which would probably be slow and a little bit boring, he's like, you could consider going to a small company and trying to build the ladder. And I ended up getting doing that and I think that was good advice. It was like the company sold nutraceuticals. So things like protein powders, sleep aids, beauty creams, things you'd find at GNC ended up not really loving the space, but it was a very interesting place to get started. And it was very, very like performance marketing heavy and Very data driven. And that kind of like, set me on a, uh, certain trajectory, which I think ended up being really good for me.

Speaker A: Super cool. And was that in Boston?

Speaker B: Yes. Yeah, yeah, yeah.

Speaker A: I feel like I saw that. I feel like I've seen jobs from that company, like, in the job boards in the early 20 teens, basically. I can almost picture the job board in my mind back when, like, Bostono.com was really popular in sort of that era of tech.

Speaker B: Yeah, yeah, we were. We were everywhere. I'm sure you saw us all over the Internet. We're spending millions and millions of dollars a month on, on paid media that you couldn't have missed.

Speaker A: And so if we could go back in time and maybe just be a fly on the wall for you your first week of work, what would we have seen and observed about you?

Speaker B: I think you would have seen I was, uh, very eager. I was like the first one in the office, last one to leave. I was definitely that guy. Just like, working really, really hard, but also, like, just so green and not really realizing. Would have been funny to see, like, how determined I was, but how little I knew. I remember one of my first assignments was to do an analysis on these campaigns. And I remember I, like, diligently, like, went through all the data, put together my thoughts, and I sent it to my boss in a Word document, and it was an analysis. And he just opens it and smiles. And he looks at me, he's like, so this would probably have been much better in Excel, right? And I was like, yes, sure, it would have. But that, like, I didn't even. I didn't even know what application to pick. And so he sent me a bunch of, you know, he's a nice man. He sent me a bunch of articles. And like, this is like, what a Vlookup does. This is what's so myth. This is a pivot table. So I was like, very, very green. But I came out of the gate really, really fast.

Speaker A: Were you getting dressed up for your first gig? Were you wearing, like, nice pants? Was it that kind of job?

Speaker B: It's probably like khakis in a polo shirt, if I had to guess. I don't remember, but probably for my first couple weeks, and then probably I stopped doing that.

Speaker A: I can remember that time in my life, like, tucking in the shirt. Like, I've never tucked in a shirt in my whole life. As an adult, I go to great lengths, like, never to be in a place where I have to tuck in my shirt. And I can remember, like, going through a chapter where I tuck in the shirt. I bought, like, nice work slacks. I had kind of nicer shoes, and

Speaker B: I don't know what I was doing that for.

Speaker A: So I was curious if you went through any of that.

Speaker B: Exactly. Yeah, it was. It was definitely that. But eventually it was. Boston Tech was like, yeah, whatever that is. Yeah, dude.

Speaker A: So you go on the version. I get to chat with you today. Super impressive. I'm not going to read off all the stuff on your LinkedIn because there's too much stuff to read, but, like your highlight reel of companies that you've advised, obviously you had a long, successful run at HubSpot. You've gone on to other places like Ramp, like Summit, Chase, got your own gig. Now, someone like you does not need to come on a show like this and to talk about some of the mistakes most people, like, you probably want to forget. Most of the stuff that I want to ask you about. Why in the world did you say yes to, uh, coming on this show and maybe shining a light on some of the more forgettable moments?

Speaker B: Well, I think this show is great because you do, when you look at people's career, you always see the highlight reel, but of course, it never works like that. There's setbacks along the way. And one of my favorite quotes is from the movie the Founder. It's about, like, the guy who started McDonald's, and I'm very, very far away from doing anything that impressive. But he goes, and just like that, 20 years later, I was an overnight success. And I think that's hilarious because it is like, you don't see the first 20 years of just, like, people being an idiot and falling on their face. And I think, like, all you see is the highlight reel, and that's of course not how it goes. So I think it's a great thing that you're doing to talk through some of that stuff.

Speaker A: Hell yeah, man. Well, dude, let's double click on a few of yours. So I like to ask about questions in a certain. A few different categories. One of them is around strategy and influence. And this is just because I think for most of us, some of the most important lessons that are hard to learn from a manager and a mentor are the right way to share your thoughts in a way that brings others along. Usually we figure out if our strategy is good or not good when it's too late. And it's hard to rejigger things. And I hear about it a lot from my coaching clients. I've made a bunch of mistakes in my own journey here. And so I like to double click on one of those moments. So for you, I'm curious if you can think about a time when you were blindsided, when you are sure that you, you had the right strategy or uh, idea or vision and then you got a reaction from somebody else above you, from the leaders, from the exec, from whomever that caught you off guard a little bit.

Speaker B: I think I have a pretty good one for this. So at HubSpot I ran the paid media programs like Google Ads, Facebook ads, LinkedIn ads. But I also ran smaller uh, team, still a big team, which was the affiliate program. And for your listeners who might m not know what that is, affiliate marketing is we had partners that had an audience or a website or some, something that, and we would give them a, it's called an affiliate link or a tracking link and they could go out and they could promote HubSpot and in exchange they can get a uh percent of revenue for any business they send HubSpot's way. And it was a great program. We had certain terms and conditions that affiliates had to follow. We had a lot of them actually. And one of them I remember was they weren't allowed to drive traffic directly to our website. They had to go through their own thing first and then to our website. And the reason for that was there's too much brand risk. So if we let people like buy ads or send emails or do something, it could be perceived as HubSpot's doing this thing, not this other person is doing this thing. And that's kind of risky if they say something incorrect or stupid like it wouldn't be us saying it, but it could look like we're saying it. So anyway we had this one affiliate that we were working with for a long time was driving a ton of volume and uh, he wasn't it turned out, following that rule. But all it wasn't fraud. Like everything was legit. And uh, it was like he was great. He was like helping really helping us reach our goals. We liked, we had a good relationship with him and I was kind of like let the guy cook. Like we can manage this. We can like we can review his stuff, we can make sure everything's on brand. We can uh, put like tools in place to monitor. We can manage this contractually and operationally. I'm not saying we should open up this rule to the whole program, but this is something other companies allow this. We didn't but it's not like unreasonable. And anyway I kind of like made the call and mentioned something to uh, my manager. And she, it was like hard. No, she was like, no, we're not doing that. And it was this whole, it was this whole big thing and it was a little bit of a blind side. And uh, you know, I had to go back and like unwind that decision and tell everyone, no, we're not doing this. Like, it got shut down and yeah, it was fine. I didn't agree. I think sometimes this happens at work where you don't always agree with your boss, but that was definitely a time where I made a decision. I thought people were going to agree with me. And I think I underestimated the risk tolerance on the brand side and only was factoring probably in too much like what this revenue boost is worth. Like the risk, risk, reward, calibration. I was doing differently than our leadership team was doing.

Speaker A: About a year ago I had the opportunity to coach this amazing guy named Philip. He was the head of growth for a pretty large subscription business. They were series A on their way to series B when he and I worked together. He was an incredible guy, but relatively new to the head of growth role and relatively new people manager. And so a lot of what he and I worked on together was creating a team of a players, hiring them, putting the right team structure in place to support his growth goals and what it looked like day to day, week to week to manage that team. And he had a big team. He had 12 US based team members and another 25 overseas contractors on his team doing all of this different specialized execution work that ended up being a huge lever for him. Fast forward to today. Philip co founded a business called Hire Overseas, helping other teams find, hire, train and manage exceptional overseas talent based on the experience that he had in his previous role, which is pretty cool. So if you're looking to bring on some amazing talent in 2026, check out hire Overseas. It's built by a member of our tribe. Former head of growth co founder also comes from the startup marketing world and they can help you find amazing folks to join your growth or marketing team. You can hire growth marketers, paid ad folks, SEO designers, content creators, dozens of other roles. Check them out for yourself@hireoverseas.com value it's higher overseas.com value this episode is presented by Novatic. If you've been following me or you're a fan of this show, you know how bullish I am on the interactive demo space and how much I love the Nevada team. Done a ton of stuff with them over the years and they just dropped a bunch of new features that are really exciting. First they've got a new template library you can choose from. A bunch of pre made templates that have the most common demo use cases and all of the best practices built in help you go 0 to 1 in a few seconds if you're not sure what to build. They also have a new AI storyboard generator. It's exactly how it sounds. You drop in a website URL or some copy or a landing page, whatever you've got, it reads the information, pulls out the key sections and then builds a working product demo for you in a couple minutes. And after you've built your demo, you'd probably want to use your data as part of your go to market approach. They've got a bunch of plug and play demo playbooks where you can send that interaction data to your CRM. You can use it to trigger alerts, all kinds of good stuff. It's actually a bunch of the things that my team built manually took us forever when I was in house. So I love this. And after you've built your demo, if you need to make any adjustments, if you're displaying numbers or data, as part of that, they have a new table AI feature which helps you to clean up that data in a more conversational way and at scale in just a few seconds. They have made it so stinking easy to use your product as your marketing tool without needing an engineer or heavy design work. You can get started with all this in their free plan. Check it out@novatic.com value to get started. That's nevadic.com value and I'm curious to know like, because I also worked at HubSpot a little earlier than you and at some point they prioritized taking risks and that was like one of the most important parts of their operating system and the company culture. And so I'm curious if this was at a time when maybe that was starting to shift. Like, were you surprised by that reaction because of that sort of historical context? Or had that shift already been underway and maybe your personal operating system was maybe just a little bit more risk tolerant?

Speaker B: I never thought about it like that. Maybe I do think HubSpot, um, is willing to take risks and gamble and let people fail. I think that when it comes to the brand, they're very, very protective. And I do think that that probably changed somewhat. Like when I started there, especially like coming from my previous background, like everyone was just kind of like letting things rip and because if you said something live that isn't exactly right. No one's heard of HubSpot, um, it's fine, but like, at a certain point, it's like if you make a mistake, this screenshot is going on TechCrunch with a headline, HubSpot, what are you doing? You know, and everyone sees it. So I do think, yeah, probably the company changed a little bit. I wouldn't say that HubSpot is not risk tolerant. They do have a good experimentation culture. But for this one in particular, yeah, it was, it was a no.

Speaker A: And so can you take us to that actual conversation? I'm like, if we could go back in time. Is it with you and your manager? Is it like you and your manager and their manager? Is it like you get called into a room and they're in the middle of talking about it? How does that conversation unfold?

Speaker B: I think I brought it up like in a one on one, somewhat casually, not really expecting it to be a thing. And it was kind of like, whoa, hold on, back up, back up a sec, let's talk about this. It did end up getting escalated. It was a meaningful enough thing that like, more people had to be looped in. Probably like my boss's boss, the team that worked for me, just like, are we sure we want to do this? Like, we're going to notice it in the numbers. But it was like, yeah, we do.

Speaker A: And so for folks listening to this, how can you sniff this kind of stuff out faster the next time? In retrospect, are there early warning signs or red flags or patterns that the version of you today might recognize that that version of you didn't know to look for?

Speaker B: Yeah, I think that, I think I have come to learn, maybe this is like a very specific answer, but I think I have come to learn that when you're dealing with things that can impact the brand, you have to be very careful, especially on paid media, because, like, I've bought so many hundreds of millions of impressions all over the world and people, people see this stuff a lot and it's actually really hard to like some of it's subjective and it sucks when you like get a screenshot. For some, someone is like, this ad isn't good, especially when they're right. And I think that I don't know if there's a way around it, but I think probably erring on the side of being more careful on brand, like you don't want to be too careful at work. I do think it's good to take some risks and ask for forgiveness sometimes. But if you're doing something that there's a process in place because it's a brand thing. I think that's the kind of thing you do have to not really gamble much with.

Speaker A: I think this is one of the hard parts about working in growth because sometimes the best results are surprising. And there are things that you thought of kind of quick off the cuff and it turns out it solves something that you didn't fully understand, but it turns out was really impactful. And so you kind of need to try a bunch of stuff to get, uh, enough data points to figure out what works and what doesn't work and eventually find the patterns. And so to do that, sometimes it means you need to figure out where the line is. And to go over the line is how you figure out where the line is. And that's hard. So I used the words earlier, like the cultural norms and the operating system. And that's something that I think everybody needs to think about and to assess. Every company is different and even different moments at the company that line shifts and their priorities shift. And that's just one of the challenges with the role, I think.

Speaker B: Yeah. Do you know about Jeff Bezos's like two by two and one way doors versus two way door thing?

Speaker A: Yeah. Yeah. So it's like the one way door. Well, it isn't his whole thing. Like most decisions are two way doors. Like if you make a decision you can always roll it back. There's 1% of decisions you can't really roll back. Is it sort of like that?

Speaker B: Yeah. His thing is like if it's a two way door and you can just hit undo, just do it and we'll undo it if we have to, no big deal. Or if it's like, if it's kind of a small decision that if it's a one way door, it's fine, just do it like we trust you. It's the big decisions that we can't undo. Okay, let's take a beat and, and be really thoughtful about this.

Speaker A: So shifting gears a little bit. One of the other things that I hear about a ton with coaching clients and even in my own journey is this transition from being a, uh, great doer to becoming a manager and a leader. And there's normally some stuff you have to learn as part of that and some stuff and some habits you need to unlearn. And I'm curious for you what comes to mind as I share that if there's been a time for you in the way that you are doing stuff or managing a team just wasn't working, either you were trying to do too much or you were trying to kind of grind your way through it or staying in the weeds when you should have been pulled out any of that track for your journey.

Speaker B: This happened twice for me recently. So when I started Summit, uh, Chase, my paid media agency, it was pretty much like I had done other businesses before. And it was kind of like a grind. Didn't really work. This one was right away, flood of people that wanted to work with us and more and more and more. And at first it was just me and you know, I was the one working with all the clients and running the Google Ads and Facebook ads and LinkedIn ads. And that worked for, I don't know, like I was able to do it for the first five, no problem. Eight, I was a little stretched. Ten, it was like, oh dang, like clients are waiting on me for things like I'm, um, working 15 hour days. This is not going to be sustainable. There was like this huge wait list piling up and then, so then I hired five or six people and, and that was better. That worked for a period of time. I became player coach. I was still supervising everything, queuing every ad personally, like setting all of the strategy, making all of the big decisions. And that worked for, I don't know, 15 clients, 20 clients, 30 clients, whatever. And then it was the same thing again where I was just like everyone was waiting on me back to 15 hour days. And then eventually it was partially a problem. It's like I just needed more people. So I hired 10 more people. But it wasn't until I kind of built all of my systems and processes and strategies and put together SOPs and looms and trainings and it's like, this is how we do things where everything. Because it's like, why do I like, sure, it's great if I'm the one QA personally, but why can't there be a checklist and like a peer qa? And that's going to be just. Do I have some special QA ability? No. If you hire smart, capable people, that's fine. Yeah. So it was like going from player to player, coach to manager, and then like managing managers and processes and systems. I kind of had to do that transition twice and now I think everything is pretty stable and going well.

Speaker A: Hey, I hope you're enjoying this episode of the show. If you are, please don't forget to hit that subscribe button on whatever platform you're listening on. The data show. Something like 40% of the people who listen to the show are actually subscribed. It is the best way for you to support the show. And it helps the algorithm find other listeners who are just like you. If you're feeling generous, a quick rating or review makes a huge difference as well. Thank you so much for listening and for your support. Now, let's get back to this episode in the creating of the SOPs and the checklist and all that stuff. Obviously you did it, uh, at a certain point in the journey. Here is the reason why you didn't do that earlier, because you didn't know to do it, you didn't think it was important, you. You thought it was too soon, or some other reason. I don't want to put words in your mouth.

Speaker B: Yeah. I think when it's a smaller company, like, so when it's just me, I feel like there's not really a need for it. There's not going to be any breakdown in communication between anyone. It's only me. I know the expectations. I know how to do this when it's just a few people. My system was just, like, manually watching everyone all the time. And that kind of worked for, like, a few people. But then at some point it's just like, this is crazy. I can't read every single word that's written by everyone in my company and review everything. And at that point it was like, we need to have some process in place.

Speaker A: And have you done that when you were in house as well? Like, did you do that when you were leading any of your performance teams or other teams?

Speaker B: Definitely. So, like, an example of that is, like, when we first started. So at HubSpot, we kind of had two jobs, uh, on my team. One is we were doing customer acquisition for HubSpot, so we were getting people to sign up for HubSpot. But then we also kind of served as this, like, mini agency within the company. So there would be like, some random person on some random team who has some idea and wants to run ads, and they have a, uh, $20,000 budget or whatever, and they could come to us and we could help them do that. And at first, the process on that was so chaotic. It was just like firing off slacks, like, hey, I want to do this thing. And then we have to go back and forth, well, what's the audience? How much budget do you have? How are we going to report on this? What copy do we want to use? Do you have, like, design? Are we working on video? And, you know, you're asking the same question over and over again, saying, oh, we should probably have a form, like an intake form that gets fed into asana that gets assigned to someone that has capacity. So definitely had to build that and then some many times in HubSpot.

Speaker A: Man, it's so funny to hear you say. It's not funny, but it's awesome to hear that you say that. Honestly, it's one of the things that I stumbled into as I scaled my team. I found that the way that I intuitively thought about things and made decisions and the way that I approach projects was hard to train people on. I'd be like, why? I would find myself getting frustrated, like, well, I don't understand why they don't just get it. I've explained it a couple times. I've sort of showed them. Um, but it wasn't until I started creating artifacts. Eventually. I called it my operations manual, which is sort of a set of rituals, beliefs, prioritization frameworks, SOPs, things like that. That took me a long time to get this stuff out of here and figure out, like, oh, when. When I see something that I think is good, why do I really think that? What does it really look like to lead the, um, project or run some experiments or whatever at an A player level? And then eventually I wrote all that stuff out, I put it on paper, and then I trained my team on it. And then eventually I. With the rest of the company. And then finally I felt like I unlocked some of my time. Because for me, until then, I was just working. I was in every meeting. I was like, in every major decision. Just like you had all flowed through me. It's really a tough place to be. And most folks wait too long to do. The thing that you talked about doing is what I've seen.

Speaker B: Definitely would have saved myself a lot of pain if I had done it sooner.

Speaker A: Why is it so hard for people to figure that out? Right, because you've gone through this, I've gone through this. I hear about this all the time. Like, what is it that we're missing? What should we share with people who are out there who haven't figured this out yet?

Speaker B: I think for me, part of it came down to trust issues. And I just wanted to. Like, I knew I interviewed well and had hired smart, capable people that had done this before, but they're still in the back of my head. It's like, what if somebody messes up? And it wasn't until it becomes impossible, you just hit this breaking point where it's like, this is not going to work. And, uh, it also flipped where it wasn't possible. And at a certain point, I was so much Worse, I was slowing things down. You know, even if we had made some mistakes, that would have been better than me taking two days to get back to people. And then, you know, you do it and it's fine and it's great. And it's like, everyone's better off. You're better off, your team's better off, the clients are better off, the business is better off. Uh, yeah, but you have to get over that. That hump.

Speaker A: Well, and whether you're leading an agency or a team, when it's yours.

Speaker B: Yeah.

Speaker A: There's a lot of accountability and pressure that I think we put on ourselves for things to be perfect. If there's a mistake, it's a reflection on us. We're not good if something isn't going well. And for me, there's always been a little bit of my identity that's been tied into that where it's like, to let go means I could fail. And that's, like, really scary because I don't identify, you know, I don't identify as somebody who would let myself fail. But. But to get further and to accomplish more, we kind of have to do that.

Speaker B: Yeah. Yeah, exactly.

Speaker A: I also chat with a ton of folks who struggle with different flavors of imposter syndrome. You ever work through some of that stuff where your confidence has taken a hit either through feedback or being in an environment where you feel less than or difficult conversation or any of the above?

Speaker B: Yeah, definitely have gotten hard feedback many times. Honestly, it's been a blessing to work with managers that, uh. Tell me how it is. I can give you an example. And actually similar to my last one in the sense that it was like a brand thing. So I had this other job before HubSpot, that was extremely direct response. It was just like everything was return on ad spend, return on ad spend. And this is, like, embarrassing to talk that, like, I even did this. But I remember I got the HubSpot and I was using my old tactics, and I had this headline, and it was like, creepy question mark maybe, but still an interesting trick, talking about a HubSpot product which was allowing you to. I mean, it was not doing anything remotely illegal or unethical, but it gave you a lot of visibility into a lot of stuff. And the headline just crushed. I was smashing my goals. And I got some. I got some hard feedback. This is, like, totally warranted feedback. Just like, yeah, you can't do that here. You know, like, early on in your career, your first instinct, when you get feedback, fight back. Like, just get defensive. I think I Did some of that. And anyway, it was totally accurate feedback. And by the time I left HubSpot, I was the one that was like giving presentations of like, these are things we don't do in ads. Like, and I probably use that example. But yeah, like, I think, I don't know. I've gotten feedback so many times at this point from managers that I've started to recognize a physical sensation that I get where like, I don't even know how to describe it. Maybe my blood pressure's going up or something. And I know when I feel that just like, shut up. Listen, sleep it off. Don't say anything defensive even if you're 99%. Because in the moment I'm like 99% sure I'm right. And then I wake up in the morning and it's like, oh. And the truth is, when you get feedback you don't agree with, usually in my experience is a mixed bag. Usually after I've given it some thought, I still think I'm kind of right on some stuff. But usually there's some aspects of the feedback that they were right on, but you can't see it in the moment. In the moment, you just think you're right about everything. When I feel that feeling, I just know, like, okay, agree, say thanks for the feedback and then come back 24 hours later. And if the feedback turns out to be right, great, you've agreed and you're in good shape. Feedback turns to be wrong. Now you're like having a level headed conversation that. No respect.

Speaker A: And did you get that sensation during that moment when you got feedback on the creepy, uh, ad copy?

Speaker B: I don't know if I was mature enough yet to handle that. Great. I think I handled it fine. I didn't get fired thankfully, but probably should have been.

Speaker A: And if we could go back to that one, like, was that, was that in your one on one? Did they initiate that one? Did you initiate it because you thought things were going well? Right. You're hitting your goals. Probably still somewhat new. If you're hitting your goals, you're probably kind of swaging a little bit. Or at least I would have been. Yeah. Take us to that moment.

Speaker B: It was a sit down. It was like my boss had looked under the hood and it was like a, uh, we need to talk moment.

Speaker A: Yeah.

Speaker B: Uh, it was not good.

Speaker A: Was the heart beating a little bit as that conversation starts to unfold?

Speaker B: Definitely. Yeah. Yeah.

Speaker A: Hey, if you're enjoying the stories on this show and feeling like you're ready to tackle some of your own Hurdles. I'm here to help. If you didn't know already, I offer one to one coaching specifically for people who work on or around growth teams who want to have a bigger influence and impact in their roles. Maybe you're navigating some tough moments, whether it's managing your team or handling feedback. Maybe you just want to step into a bigger leadership role or maybe you're at a unicorn company today and you want to make sure that the company doesn't outgrow your skill set. Either way, I can help. If you're interested in learning a little bit more, head to deliveringvalue co coaching to learn a little bit more and set up a call with me to see if we jive. All right, enough from me. Back to the episode and you talked about learning to pause when you feel that feeling. I've had a version of that sensation. I think everybody has a version that's personal to them. For me, I get a little tingly is maybe the best way to describe it. And I feel like my brain shuts down a little bit and sometimes my eyes feel really dry. Sometimes it's similar to when I'm having an allergy attack where my eyeballs feel like they're on fire and it's like, that's what it feels like for me. And anyway, so you've got a version of that. How does somebody learn to pause? Or how did you learn to pause? Because I feel like that is a hard skill to learn how to do in a high stakes moment.

Speaker B: Just reflecting of like thinking about it from the other person's perspective. They have feedback for you. In their perspective, you're not doing something well or correctly. And if your initial reaction is defensiveness, they're going to be like, okay, so he's not hearing me. He's like, I'm trying to give him feedback. He's not getting it. In their perspective, they're right. Even if they're wrong, their perspective is their perspective. And if you just start fighting, they're going to be like, okay, so I can't work with this guy. I'm trying to help him.

Speaker A: Right? This is an easy correction, right? This isn't the end of the world. We're letting him know this is starter. Stop doing this thing.

Speaker B: Yeah. And if you just say, if you just always fight, then yeah, that's being hard to work with and that's not how you get better. Whereas if you reflect and I'm not saying never push back on feedback, like I think sometimes I've gotten feedback that was unfair and I did push back and I'm just saying be careful about doing it in the moment because I think people's first instincts can lead them wrong. And uh, yeah, it was just like a pattern recognition with that physical sensation. And I do think that's kind of like a blessing if you, if that happens to you and you can identify it. It's like, okay, that's your cue. I get this with emails too sometimes where I'll get like an email that pisses me off and I'll get that feeling and I know and I type it up and now I know. Rex, don't hit send when you feel like that. Come back.

Speaker A: But, but you gotta type it up. Or at least for me I gotta, otherwise I'm just gonna stew on it.

Speaker B: Yeah, yeah, but I just, I know I'd sent it enough times that I regret it and it's like now I know, like now I know what it feels like.

Speaker A: Yeah. And because you do know what it feels like, has that influenced how uh, you give feedback to others?

Speaker B: Yeah, I think I do try to at least the first time be very nice, very gentle. I always, always give examples. I think if you give feedback, the person deserves to, to get examples. And I also, I do try to be patient if they get defensive, especially if they're like earlier on in their career because I know like, it's hard but yeah, I mean getting tough feedback's hard but like the truth is the person giving it to you, hopefully they're on your team and they like are rooting for you and they're not telling you you're an idiot, they're just saying, hey, there's, this is a way that you can get better.

Speaker A: As you've progressed and navigated your career, what has been maybe the most surprising part of the leadership journey and the manager journey kind of once you started down this path, anything specific you had to uh, either identity wise kind of shift from or learn or unlearn specifically that we haven't talked about already.

Speaker B: You have to manage different people differently. Mhm. I think that some people need like, they really do need a kick in the butt and they need a lot of structure and they need their Kanban board and they need regular check ins. No one likes to be micromanaged. But I do think there is a gradient of like you have to be more involved with some people than other people and I think if you mess that up, you can really screw yourself over. So if you have someone working for you that really does need structure and you don't give Them any it's not going to go well. And then on the other end of the spectrum, if you have a real self starter who is like very determined and is already working super hard and doing a great job and uh, you try to micromanage that person or you try to give them too much structure, that's going to go over terribly. So you have to definitely not a one size fits all when it comes to leading and managing people in any

Speaker A: tools or tricks that you've picked up to identify sort of where on the spectrum somebody new might be.

Speaker B: I think you kind of have to wait and see to an extent because I think if you start applying your, your standard method and you get it wrong, you're liable to really piss people off. I'm definitely in like the self starter camp and I don't need a lot of direction and I've had managers that uh, you know, I start with them and they start pushing me and being like when are we doing this? I'm just like, I get it, you've had a bad experience with other people. I'm telling you, you don't have to do that with me. It's going to get done. I'm extremely type A on top of my shit. Like you don't have to. And it's just if they just waited two weeks and just watched me work, they would have figured that out.

Speaker A: I had a manager do that too. They asked me to write down at one point how I was spending my time, maybe do a timesheet more or less. And I was like list, we are crushing our numbers. What is the problem? You don't need to do. I don't know what's going on with the other people on the team, but this is going to push me off of the team if we keep doing this. Right.

Speaker B: Right. And like so from their perspective they had had a bad. I guarantee you they had a bad experience with the person before you for sure. And they tried to apply that to you and it just, they shouldn't have.

Speaker A: And for folks listening if they want something else to try. One thing that I have liked is having everybody create a readme file. I actually do this as a manager for if I have a new direct report it's like here's like my manager pet peeves, my communication preferences, the decisions. I really want to be involved in some of that kind of stuff. And then on the, you know, if you're a new hire reporting up to a new manager or if there's somebody new on your team coming in like to have Them fill out a version of that as well. Here's the pet peeves that I have with a manager. I like this type of communication, this type of involvement. Uh, I do my best work in this environment. Stuff like that can be helpful as well for folks listening.

Speaker B: Yeah, we did that at HubSpot, and that kind of thing is very. Not really my style, but I found it extremely valuable. And that's one of those kind of like corporate feelings, the exercise that I actually took with me to some machine agency. Because, yeah, I do think that, you know, if you don't talk about that stuff, they never get said. It's a shame.

Speaker A: Yeah, yeah. Well, it's like, it's hard to figure that stuff out in the moments, like once the car is already driving, it's hard to be like, well, how's the engine going? Do we need it? It's like, uh, you got to do that before you get in, before you get going too quick. And at the beginning it makes sense.

Speaker B: Yep, absolutely.

Speaker A: And so for you, has there been a, uh, mindset shift or a habit or something like that that you feel like has had maybe some of the bigger impact on your career growth?

Speaker B: Yeah, I think that two things that happened. One is like we were talking about earlier, when you're working in growth, I do think you have to do a bunch of stuff and try a bunch of things. And I do think I went through an evolution of this outside of the brand stuff, which I still think you have to be careful with. I think I have gone through an evolution of not trying enough stuff and kind of being too careful. And I think when I take a step back, things are a lot less risky than they seem. And if you're ever on the fence, I do think you should err on the side of just try it. So when I'm like, people are asking me all the time, when should I start on paid media? And I don't know exactly the timing, I think that can be hard. But I do think almost every company should try it. Because if it doesn't work, if you look just getting started in your own family dollars, you have to be more careful. But let's say you just raised $5 million. It's like if you carve out 50 to $75,000 for a paid media experiment and it doesn't work, it's like, oh, well, like, I guess you shouldn't talk about money that way, but like, your life goes on. When you're thinking about if your business failed or succeeded in five years, it's not Gonna. That is going to be a rounding error. It really has no material impact on your business. Whereas if you don't try out something like that, there might have been, like, a huge pipeline driver that could be completely transformative for your business that had this huge upside. So, like, the downside is so small and the upside is so big. And I think that's the case with many things in marketing, not just paid media. If you're ever on the fence, I think try it out. And that's a mindset shift that I came to learn. So that's the first one. The second one is I had this, like, business, like, 10 years back. I effectively was an affiliate myself, but it was a white labeling thing. So I had. I put my logo on someone else's product and started running ads. And at one point, I was spending like $50,000 in my own month on paid media, uh, of my own dollars that I didn't have. It was on credit cards and lines of credit from different ad networks. And that experience got me to think really, really critically about dollars. Because I think that people who work in paid media, uh, and probably in business in general, they kind of start thinking about dollars as units and they stop forgetting, like, that these are like, doll. Like, you can buy, like, MacBook Pros with this or cars. This is like, dollars. And that experience. I still go back to that mindset sometimes when I'm on the fence about a tough decision. I'm like, rex, if you were working on Skyvolt, how would you have made this decision? And it's just a little mind game that I play with myself. And when I do that, actually, the decision often becomes very clear. It's like, what would I do if this was my money? And I actually took that a step further at HubSpot. Everyone that worked for me, I made them come up with a fake business. So we have Lara's mousetraps and Josh's socks. And. And anytime they're like, rex, what do you think I should like, well, what would you do if it was Lars Mousetrap?

Speaker A: Oh, I love this, dude. That's such a fun idea.

Speaker B: Yeah, yeah. Like, what if this was your money? What would you do? And I think it just becomes immediately clear, like, a lot of the time.

Speaker A: Dude, that's so funny. I stumbled into something like that too, where sometimes folks will come to me, even now as a coach or as an advisor, and they'll be like, hey, do you think we should do this or this? It's kind of risky. And I. I would always Ask him. And I'd say, if this was your family business, forget the VCs, forget all that shit. If this is your family business, this was going to be like your inheritance and everybody you worked with was like related to you in some way, shape or form, would you still recommend it? And if the answer is yes, then it's obviously the right thing to do. And if the answer is no, then it's obviously the wrong thing to do. And if you're not sure, then let's talk about how to maybe take a bite of it and see what it feels like. And so I love that question where they made their own business and was like, would you spend your business's money on this?

Speaker B: Right, right. Tiny little mind game, but I think pretty effective, dude.

Speaker A: I mean, I do that even in my own thing, right? So I'm on my own. I work with some partners and, you know, an EA that support my business. And when I, when I make decisions, it's literally like, hey, this is our vacation money. You know, could it, if it's a moonshot and it works out, totally worth it, right? A rounding error in my life. But, like, it also is a vacation or diapers money or swim, uh, class money or whatever it is, you know, and that changes how you make decisions and cater to the brand and to the money, which is cool. And so we've talked about a few of the learnings and the mistakes along the way. As you look back and do some of this reflection, is there a through line for you between some of the toughest moments and the biggest lessons and the most amount of growth?

Speaker B: I don't know if it's a single line, but I think the common thread is just you learn a little bit as you go and, I don't know, building a career or a business, sometimes I feel like it's like a, uh, video game. When you lose the level, you don't have to really start over from the beginning, you just start over from that level. I've, like, tried starting a bunch of businesses and at first it's like, how do I make an llc? How do I build a website? What do I do for my terms and conditions? Do I need terms and conditions? You have to figure out all of these little things and then if it doesn't work, you go to the next one. You're not really starting over. Uh, you already know how to do all that stuff. You've thought about it, you've made the decisions.

Speaker A: Yeah, that's a good analogy too. You're right. And even if you do have to start the level over, you speed through it to get back to the point where you failed. Right. So it's like getting back to where you left off or where you, where you stopped is faster. And so it's all about how do I incrementally keep plowing ahead and unlocking, uh, new stuff.

Speaker B: Exactly. Exactly.

Speaker A: Dude, I appreciate you coming on and sharing some of the game and your journey and the lessons here. For folks who are listening that want to connect with you, where should we send them? We'll put links to everything in the notes.

Speaker B: Yeah, so I do a bunch of stuff. The easiest way to Find Me is LinkedIn. I own a paid media agency, Summit Chase, so if you need help running ads, you can find me there. Uh, I also work at Cursor building out their performance marketing team. So if you are a builder and looking to build with AI, you should go check that out. But yeah, feel free to connect with me, find me on LinkedIn. And always fun to jam with different folks.

Speaker A: Hell yeah, dude. Thanks for coming on, man. Appreciate it.

Speaker B: Awesome. Thanks, Andrew. Take care.