BRUTAL Truth About Startups, VC Pressure & Scaling to $3M ARR with Max Greenwald

Max Greenwald, CEO of Warmly, shares his raw, unfiltered journey of taking a startup from zero to $3M ARR over five grueling years. Comparing the startup grind to an ultramarathon, Max emphasizes that success isn't about raw strength—it's about feeding your brain the right "nutrition" through constant learning and simply refusing to die. He candidly breaks down the fundamental misalignment between founders and venture capitalists, noting that while VCs need a few unicorns and expect the majority of their portfolio to fail, founders are playing a single-hand game where survival is the ultimate metric. Through multiple pivots—starting bizarrely with "Tinder for co-founders"—Max outlines how to navigate the "idea maze" and finally hit product-market fit. He borrows the brilliant "supermarket vs. lettuce" analogy to explain software stickiness: are you a necessary system of record or a nice-to-have feature that gets cut the moment it isn't fresh? Max also unpacks why taking customer and prospect calls remains the highest-leverage activity for a CEO, warning leaders not to hide behind the excuse of "being strategic."

Discussed in this episode

• How building a startup is like an ultramarathon focused on daily learning nutrition rather than raw endurance.
• The fundamental misalignment between VC portfolio strategy and a founder's single-minded need for business survival.
• Why founder transparency and managing investor expectations are critical when trying to extend runway.
• Navigating the idea maze and surviving seven major pivots to eventually find real traction.
• Defining product-market fit as the undeniable visceral feeling of being yanked forward by your nostrils.
• The difference between building essential supermarket software versus easily cut lettuce software.
• Leaning into brand differentiation and the software cowboy ethos to stand out in a crowded, noisy tech market.
• Why founders must continue doing unscalable tasks like joining prospect calls even as the company scales.

Episode highlights

1. 2:15 — The ultramarathon analogy for startups and learning nutrition
2. 5:30 — The brutal misalignment between founders and VCs
3. 10:45 — The overnight success that actually took 1,861 days
4. 14:20 — Navigating the idea maze and surviving seven pivots
5. 18:10 — Asking founders about their remaining runway before joining
6. 21:30 — Defining product-market fit with the nostril test
7. 25:15 — The supermarket vs. lettuce software analogy
8. 31:40 — Competing loudly on LinkedIn in a crowded market
9. 37:20 — The birth of the Warmly software cowboy brand
10. 41:50 — Doing unscalable things as a strategic leader

Key takeaways

• Startups require constant learning nutrition, not just brute endurance.
• Founder and VC incentives are fundamentally misaligned regarding risk.
• Real product-market fit aggressively pulls you and your product forward.
• Build supermarket software that customers need every week, not lettuce.
• Never stop taking customer calls, no matter how strategic you get.

Transcript

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Welcome back to another episode of the revenue reimagined podcast. We have a, I guess we'll say a friend of the show today because Warmly is definitely a friend of RR. We have Max Greenwald who is the founder and CEO of Warmly, which if you don't know and you're living under a rock, is an AI sales platform that generates warm leads. He's a first-time founder who spent time at Google, didn't know anything about sales when he started Warmly five years ago.

And after we'll say a few pivots, they've actually hit their stride, have over 300 paying customers who want to use AI and automation to land more sales. We'll talk about this year of clear that you've been doing that I've been following along with. Um, Max is an avid skier and ultramarathon and triathlete, so I'm just going to go eat my ice cream in the corner because you're in much better shape than I am. Uh, but welcome to the show, Max.

So great to be here. Thanks for having me, guys. Max, welcome to the show and, um, let's start off a little bit differently. So you're an ultramarathoner, uh, you're, you're, you love skiing.

What's the parallel between ultramarathoning and founding a tech company? I mean, I think uh, I like that one. I mean, I, I think it's pretty much there, right? It's just the idea that uh, it's it's it's uh, not a sprint, it's a marathon, probably an ultramarathon.

It can take a lot longer than you think it's gonna, uh, take. And uh, the other fun analogy that I'll draw is that it's not a race about your endurance, it's a race about your nutrition. Um, and basically what that means is, as long as you're learning as much as possible every day, and that I'm gonna equate to eating right during this race, right? Eating the goose and the gels and the bananas and whatever it takes to like make it to the to the, you know, the finish line, um, you're gonna be able to sustain and endure throughout the distance of the race.

Um, and I think a lot of people think that it's more of a an um, a strength race, right? It's all about if I did enough pushups, you know, uh, which maybe you could equate to, um, you know, did I, did I come from the right background? Or, um, you know, did I, uh, practice enough of my swimming laps? Um, and and that you can equate to, um, you know, did I, did I hire amazing people who've been there, done that?

Um, but at the end of the day, I think it's more about just learning and I'm a first-time founder, right? So I'm biased, of course, but uh, I really think it's about, it's about nutrition, it's about feeding yourself knowledge day after day, Um, and also not dying, is another very good one. I think like, you know, basically the the like classic saying that like, uh, startups, um, what is it? It's like, uh, startups, the most common way that startups, uh, go under is they commit suicide, uh, which basically is the idea that like, you know, as if you're giving up on yourself, if you don't think you're gonna succeed, um, if you let sort of negativity get you down when things aren't easy and going well, which things never are easy and never go well, um, then really you're, you're gonna fall on your own sword.

Um, but uh, if you just keep at it, pound the pavement, eat the next banana, you know, eat the next goo or gel, um, you'll be able to to get to the end of the ultramarathon. How do you, how do you rationalize that with like investors or people that are trying to put money into the company or like pushing you at growth at all costs as a founder where you're like, no, it's a marathon, it's not a sprint and you have people like trying to push you to towards that. Yeah. I don't really think the needs uh, and desires of founders and VCs are aligned.

And that's one of the hardest pieces to it. Um, I, I fancy myself a bit of a Can can you just say that one more time for everyone listening. Founders and VCs. That's so spot on.

They're not aligned. Um, and I don't mind telling VCs that. I mean, uh, one of the like the things that makes me, makes my blood boil a little bit is that, um, any VC when they give you advice, they're coming from a perspective of wanting to make their fund successful. And you might think, oh, well, they're investment in us.

If we're successful, they'll be successful. So we're all winning. But remember that a VC has 30 investments across their portfolio, and the way their portfolio construction works is, they want 23 of those companies to die. They want four of those to break even or make a little bit of money, and they want three to be huge winners.

And to say that again, they want 66%, 70% of their portfolio to die trying to be a unicorn. Um, and I am not diversified. I have one business, and I don't want to take a 70% chance that my business is gonna die. I want to take a, you know, 90% chance that it's going to be moderately successful to maybe a unicorn.

Um, and yeah, I'm not here to build a small business. Like, you know, I'm a first-time founder. I'm very lucky in that I don't have, uh, not yet at least like kids, you know, a house, a mortgage, I'm not in debt. Like, you know, I can take risks.

Um, so I am taking a big risk. Um, but I'm not gonna drive myself off the edge of a cliff the way that I think a lot of VCs will push you to. Um, and so in the analogy that we're talking about, you know, they're expecting a sprint race and, and I'm expecting an endurance race. And, um, you just have to have an honest conversation with your VC about what that looks like.

And I think they've helped me see that I'm not running an ultra-ultramarathon, maybe it's just a marathon, but also it's not a, I'm just trying to use the analogy, It's not a sprint. It's, you know, it's some sort of distance. Um, and we're five and a half years in, and I am really grateful to my VCs who came in early where we had our Series A preempted, uh, for three and a half years. We pivoted around.

Um, you know, we had a lot of skepticism. A lot of our VCs their patience was tried as they were like, we put a lot of money into you. Like, you know, where's your revenue? And we're like, oh, we have to get revenue.

Like, that's weird. Um, I, I'm saying this in the revenue remagined podcast. Yeah. I mean, for us, revenue reimagined in the early days was no revenue.

That, that, that was the reimagined part. Um, but eventually we figured it out and I think, um, as I, you know, we're, we're in a very great and lucky position that the last two years, we went zero to one million in ARR and then one to three, so we just tripled this past year, which was exciting. Um, and we've finally figured it out. And, uh, I recently posted this on LinkedIn that Warmly is the classic overnight success story, if overnight means 1861 days.

Um, because it's been, it's been five and a half years and, uh, you know, I, I think that's classic. That's classic. Like, people don't realize that they're like, oh, you guys like all of a sudden became, you know, a success and you're like, yeah, after like I did like blood, sweat, and tears on this thing. Yeah.

So, let, let's, let's talk about that for a second though, because I've been following Warmly for a long time. Um, I 1,000, 675 days. Not, not quite that long, but long. And the product today is not what the product started out with, um, or what the product iterated to or what the product iterated to after that.

Um, how did you get Max from where you were to where you are now, while at the same time, for lack of a better terms, keeping the VCs off your back, right? Because again, like, give me that revenue, or you're out. And you're not out, you're still there, you made some great pivots. I'd love to hear a little bit about that.

Yeah, so, uh, I think keeping in mind that like every pivot we were learning, like if I were to draw a graph of like time and learning, it's a ultra crazy graph up into the right, right? Like we we have this coolest curve imaginable. It's not revenue, it's learnings, that's up into the right from day one. Um, my revenue curve stays incredibly flat for a very long time and then pops up.

Um, and then my like just product trajectory curve is just all over the place. Ups and downs, pivot turns, backwards, forwards. I mean, we have tried B to C, B to B to C, B to B, we've tried PLG, we've tried SMB sales, mid-market sales, enterprise sales, um, just any just sideways, you know, thing you can imagine like we we've gone after, um, and failed at all of them, um, and really just tried to find a path in the space. And, um, one of my favorite phrases by Eric Tornberg, the founder of On Deck, was, uh, the idea maze.

And he says, you know, you're lost in the Minotaur's maze, and it's gonna take a long time to get out. And you're gonna sound like kind of a crazy person because one week you're gonna be talking about this one idea and the next week this other idea. And, uh, you kinda just have to like navigate it all. And, and I have a couple of like classic tips that I give first-time founders for how to navigate the idea maze and, and figure out the space you want to be in.

Um, Warmly, because we're warm and we want to be about connection, we, we've always been in this space of helping connect sales and marketing people to their best customers. So we've always been in the revenue space. Um, but yeah, we pivoted a whole bunch of times. I mean, the very first idea for Warmly, this is not a joke, was Tinder for co-founders.

So my problem was, I couldn't find a co-founder. And so, uh, and I was the CTO to start, built this swipy app where it was like, you know, do you want to be my co-founder? You know, left swipe, right swipe. Um, and it's a terrible idea for so many reasons.

Uh, but it got my co-founders and I to quick Google and start the business. So it was a, a good leap of faith. Um, and knowing what I know now, that's the dumbest idea in the world. No one should ever start up that.

Uh, but at least I was too naive then to, to really know that. So I left my, you know, my, my cushy job to start this thing. Um, and then it snowballed from there and, and we just, we I can tell you the next seven pivots, but, uh, long and the short of it is we tried to figure out what's the best way to connect people. And it turns out that finding more warm leads for sales people, uh, is something they'll pay money for.

And I think it's a, I think it's important for a lot of people that are potentially listening to this is and I would say this as I learned through my sales, um, leadership journey is I would always ask the founder when I do an interview, how many pivots do you have left with the funding that you have? Because the problem is you're gonna have some pivots and if you don't know how many pivots you have left, like you're gonna end up committing, you know, you're gonna die somewhere along that line because what ends up happening a lot of times is and Adam can probably vouch for this as well, you get brought in to like one or two pivots left and then it's like, shit, I don't have enough time to pivot or they think they think, hey, you've done sales before at other companies and you've been successful, so you can come in and it's like, then you look at what's the pipeline look like? What are the conversion rates? What are the, you know, all these metrics that you're running and you're like, I can't get there in six months.

Like, it's gonna take us six months to just build that foundational piece to get you to 25% conversion rate from uh, from demo to, to close. And like, they don't understand that. For, for kind of my founding sales and, and marketing leaders out there who like to come in at the really early stages and get involved with the company. I think you're asking a very important question, uh, here, which is that you should be asking, you know, how much runway do you guys have yet left and, and where are you in your product market fit journey?

And, and being savvy because a lot of founders will be like, oh, we've figured it out, we know everything, we have these great customers. It's like, no, like they haven't figured it out, and that's okay. Uh, but it is important to talk through basically how many pivots left do we have. Um, and knowing that if you only have one bullet left in the chamber, maybe that's okay, and maybe you're willing to take that risk tolerance.

But coach that founder to say, please don't try to pivot us halfway through when things aren't looking good. This is like, you know, do or die and so we're really gonna like push it and push through. Um, and, you know, some of the best companies in the world have been founded with one bullet left in the chamber. And honestly, one of my VCs once told me, you know, I'm, I'm bummed you guys have as much money as you do because it doesn't make you as, as hungry as you could be.

Cause, you know, if you're on your last leg, like, uh, you're come heller high water, you're, you're trying your hardest. Yeah. I've heard that. It, it's funny, like you you you talked about product market fit, and sadly, the majority of founders that I've spoken with, um, long before revenue reimagined, um, they all think they have product market fit.

Yeah. Um, but they, they really don't. From the eyes of a founder who has not had product market fit, um, and who now clearly has product market fit. How would you describe product market fit?

Because it means so many different things to so many different people. I'll give this credit to uh, our CTR investor James Currier, who describes product market fit as somebody taking their two fingers and shoving them up your nostrils and yanking you forward. And if you aren't being yanked forward with two fingers in your nostrils, you don't have it. And it's some version of like, you know, if you know you know and if you don't know, you don't have it.

Um, but really I think it's, you know, you gotta break down product and market. Um, market's easier to figure out because, you know, you can basically understand is this a growing space? Are there competitors in there? One of the big things that I think a lot of people shy away from is they're like, oh, there's too many competitors in this space.

Hell yeah, this is a great space to be in. That means like this thing's working. It means a lot a lot of other idiots out there who've figured out all the problems before you got there so that you can be successful. And rarely ever is first to market the one who succeeds.

It's always mostly I think more like hardest working to market, which is like somebody who puts in the most time and grinds the hardest. But anyway, that aside, market's easier to figure out. Product's tough. And and I was actually a product manager at Google and so I thought that I was good at product.

I suck at product. I am not a product person. And one of my personal journeys and evolutions as a human was realizing that I'm a sales CEO and not a product CEO. And so I'm really happy that I delegated product to my other co-founders who are much better at product than I am.

But uh, I think I tried for a long time to just sort of go by my gut and be like, these are the features that are gonna win and, oh, if we just built this thing, then we're gonna be successful. But product fit in the product market fit typically is in the form of how simple can your product be, and can your customers describe what you're doing in a very easy way, and also, especially for B2B, um, I, I like the just the simple mark of if you had to get rid of 40% of your tech stack today, are we making it or not? Um, and that's just like a pretty easy barometer for like, you know, when things get hard, do I stick around? If you have the product part of product market fit, you're, you're sticking around with the budget gets cut.

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Like, and I'm sure you're seeing this a lot, like, how fast, so if I buy you today, how fast can I get the value? And so too many, we'll call them zombie tech companies now have built, call it, 75% of the tech. They overlap with other things, kind of like what you're saying like if if I got to get rid of, you know, 40% of my tech, are you guys still, are you guys still there? Is, do I derive value based on what we're selling, um, to make that, make that successful?

One one of the um, really good, uh, analogies here and again, I'll I'll quote James Currier, uh, who's our seed investor in FX. Um, when we were talking about what kind of product he wanted it to be, he said, there are two kinds of products. You're either a supermarket or you're lettuce. And bear with me for a second.

And the idea is that the supermarket is something you go to every week. You kind of have to go to the supermarket to get food. Now, you don't have to buy lettuce. You choose to buy lettuce because it's good for you.

But if that lettuce is brown or, or, you know, isn't there, you know, isn't looking good or it doesn't taste good one week, you're gonna go for something else instead. And the equivalent in product is basically like, you're essentially a system of record. You're, you're something that just kind of has to be there. Like you kind of need a CRM.

And whether your company is amazing or terrible, you still have to have a CRM. And if there's a bad quarter or a bad year, you're gonna keep your CRM. But if it's lettuce, you have to have fresh lettuce delivered every single week. Warmly is kind of both.

And I want to the things that we struggle with actually is this idea that we have to deliver fresh lettuce every single week. If there's a single week where I don't deliver you warm leads, you're gonna cut me, right? You're gonna say, well, you, why would I pay for this thing? I didn't, I didn't get, I didn't get the fresh lettuce.

Um, and so we have to kind of have this balance of like, and we're moving more toward being this orchestration platform where you set up all your workflows for your go-to-market motion, you connect a bunch of stuff, you like orchestrate these leads, et cetera. And by doing so, even if you have a bad month, you're still gonna keep Warmly because we're kind of this like core of your like revenue and go-to-market motion. Um, and so it's definitely better to be a grocery store than to be lettuce. It's often easier as a first-time founder or just any founder building a business for the first time to start with lettuce because you can basically find a quick hit feature that's just like, here's quick value, here's quick value, here's quick value.

But be careful because if you don't deliver quick value every single week, week over week, year after year, then you're gonna get cut. So I actually love that analogy. Um, candidly, I'm gonna steal it. Um, and he steals everything.

I'll I'll take credit for it. Yeah. I think I think the way it works is, I gave I gave the other guy credit for it. But if you take it, then I get credit for it.

Uh. But I think it holds very true. Um, at the end of the day, the number one thing we hear from people now that they're concerned with is, is top of funnel and how do you build pipeline? And like, sure, you you might have a a shitty quarter, but are are we bringing in the leads that we could identify the leads?

Maybe you need to change your messaging, maybe you need to change your process. But at the end of the day, are we getting you the information you need so that you can act on it? Yep. Um, Max, you you compete against some of the, I'll say most well-known names out there.

I don't want to say biggest, I'll say well-known. Uh, people who are prolific on LinkedIn. Um, I believe I read the other day that you actually met in real life with one of your biggest competitors. Um, why such a competitive space with people who are so prolific, um, in in their brands?

Um, so it's something funny to me because about like a year and a half ago, we decided that we'd go pretty hardcore on a LinkedIn social strategy and just being very vocal about what we do. And we're taking a unique approach. I think we we I do the my going clear thing, so I basically transparently share all of our metrics and numbers on LinkedIn and share what I'm learning because I want other people to grow from that. And not other people in our space do that, but they do post on LinkedIn all the time.

But I think it just, um, what I don't know what it is, but it's some sort of like, everyone, everyone caught the bug of I think we can make money on LinkedIn and so let's all go into it. So I think that our space in particular, mainly because the number one place that sales and go-to-market people hang out is LinkedIn, um, all started going pretty deep on it. I think I've been surprised at the number of personality, um, kind of founder types, uh, that have emerged. Like I think that, uh, by nature, like often a lot of founders aren't very like, you know, kind of forward in their brand and their presence and try to hog the spotlight because they're more like maybe like geeky, right?

But, um, actually, you know what, okay, I'm gonna, I'm gonna change for a second. Here's here's my hypothesis. I don't know if this is true. My hypothesis is that the founders of the 2010s were more product nerds because like technology was really important.

But now that technology is ubiquitous and we have AI and automation, and it's really easy to build tech. I actually think that sales-focused founders are coming out of the woodwork and sales and go-to-market kind of like more, um, social type founders are coming out of the woodwork in the 2020s that are here to take advantage of the ease of creating, um, software, uh, and their strong suit is something that's yet to be seen, which is just an absolute dagger of, you know, an ability to crush it on the sales and marketing side. Uh, so that's my hypothesis, uh, as to why that we might be seeing that. Um, but otherwise I would just say we're in one of the hottest spaces in our in our in revenue technology and I think that, um, if you're starting out today, why wouldn't you build in the, uh, the the Red Hot Ocean of, you know, where where things are frothy and where people are putting money toward?

Um, yeah, I think like every batch of every, every YC batch, I look at the lists of companies and there's like six companies whose tagline is literally our tagline. Uh, and they're like doing exactly what we're doing. And, yeah, I mean, you know, it's, it's getting easier and easier to get started, Um, which is maybe good for the world but bad for sort of competitive advantages and motes in in in starting companies. Um, and so where are you gonna win?

Well, you're gonna win on brand, uh, which means I can kinda understand why some of these people are trying to build and develop their brand. Um, and you'll win on just hustle and hard work. Um, so yeah, I'm, I'm in a very crowded space. A lot of those people are also posting on LinkedIn.

I respect them. I read all their stuff. I have follow on their things. Um, and yeah, it's my morning coffee and I wake up in the morning, I roll out of bed and look at what freaking Adam Robinson's posted next.

And it's like, damn it, you know, I should have posted something like that. And, uh, yeah, I want to be friends with them too because, I don't know, I I'm one of those like rocking chair people where it's like, when I sit back in my rocking chair and I'm like 100 years old, maybe 150 if we can live, live that long with all the advancements in, in uh, health stuff. But, um, I want to look back and like be kind of amused that like I went to war with, you know, against some of these great people that I respect and admire and, um, feel like it was it was a fight worth fighting because it was like, it was fun in the arena. I'm, I'm with you, man.

Some of the people I'm closest to are are direct competitors. Um, and there's times where we might not be the right fit and we'll send them business and vice versa. But at the end of the day, like there there's enough business out there that I don't need to be an ass to you just because you compete with me. Like, let's compete and may the best person win.

I mean, Dale and I started by us competing and my winning. I have to bring that up every chance I get. Um, but here we are. He dodged a bullet.

I will say I say it every time. Dale, you gotta, you gotta respond to that, man. Yeah, he just he outflanked me. Hey, look it, I'm, I'm not too proud to say he outflanked me.

I I was not getting out of bed. But you won in the long run. I was not getting out of bed and flying all the way out to where you needed to be. But, is it, is it like a a tortoise and the hare thing where like Adam came out fast, but, you know, the tortoise won in the long run?

Well, it's it's funny because I I still, I started doing fractional or like consulting like two years ago. And then like I was when, when after this whole incident happened, Adam, like it was the same thing, six months in, 11 million in Series A funding, you know, no product. 16, 16 million. Selling paper apps.

Literally selling paper apps. We'd go in, we'd go in and we'd be like, this isn't gonna make it. So I just told him like, you know, come like come outside and like do what you do best, but do it for more than one founder and that's kind of how how it all started off. But, um, one of the things that I've been curious about because I I I Melissa's a big, you know, we're friends with Melissa Gaglion and and I saw the video that you guys that the video you guys did in Tampa or wherever you guys did that video.

So I'm curious, like, where's the cowboy, the hat, the the whole process? Like give the give the audience a little bit of that the background. Yeah, I mean, I think it's an explicit conversation where we wanted to figure out what our brand was and kind of stick true to it. Um, I think that there's this, uh, kind of rebel spirit within Warmly of never giving up, of being a bit of the outsider, of kind of watching and waiting for a moment to strike.

Um, and I think everyone wants to root for an underdog story. And there's just something about cowboy energy that I think embodies that really well. Um, you know, the the cowboy thing was first brought on by our head of revenue, Keegan Otter, Um, who's dubbed himself the software cowboy, which I love. Uh, I grew up in Colorado.

Was that, was that pre-warmly or because of Warmly? So when we first joined, um, we said that we were going to be changing our names on LinkedIn to include a couple more words to just stand out like in the text. You know, some people put like an emoji or whatever. I lowercase my first, uh, letter and, uh, of my first and last name to kind of just throw people off a little bit.

Um, just because it stands out a little more. Yeah. So I changed my name on LinkedIn to, uh, Maximus Greenwald Sales Founder. Um, and then I needed to get verified and I knew that was gonna improve my stats.

And so I had to get, they were like, unless your ID says sales founder on it, you can't like have it. And I was like, oh, fine. So I like removed that. And so now I'm now I'm just Max Greenwald.

And then, uh, Keegan was able to get verified I think through his school ID or something. So he didn't need the, uh, it was okay if he had a longer name. So he made his the software cowboy and then it's, it's sort of stuck ever since. Uh, and then, uh, yeah, we were just looking for a social outing, uh, once when we were hanging out in person and there was a sort of a a place that did branded cowboy hats.

And so, uh, now every seller on the Warmly team has a branded cowboy hat. And, uh, it's just kind of our marker, I don't know. Uh, I think that like, you know, it's, it's the people who are our customers. You know, the the diffusion of innovation curve where you have your like early adopters and then you're like, you know, late majority or whatever.

So, I think we're still, we're exiting the early adopter phase, but I think our our early first couple hundred customers are these kind of rebel rebel Cowboys that are just like trying to cowboys and cow gals, um, who are just trying to, you know, change up how they do their go-to-market motion, think a little bit differently, lean more into automation and AI, um, bring a warmer way to sell. Uh, and so, yeah, I think it's just sort of our our ethos now that we're rolling with. I love it. Dale, I would pay anything to see you sport a cowboy hat.

Um, all all over. I'll I'll leave my comment to myself. By the way, you you you I, uh, I travel a lot and this thing's tough to bring on an airplane. Um, because you can't you can't put it in a in a suitcase because it'll it'll get ruined.

Um, and then, you know, I'm like sitting there on the airplane and I can't lean back because it's like got this thing on it. So it's like on my lap or then I like put it in the overhead bin and then someone tries to like shove a backpack in there. And I'm like, no, no, I need it for my cowboy hat. Uh, and then, you know, we we have teams in Europe and in in Israel and Brazil and stuff and so, you know, I'll like touch down in in, you know, in like Tel Aviv, Israel or whatever and they'll be like, oh, haha, like American cowboy.

And I'll be like, how do you all? Um, so yeah. I love that. Max, with all the pivots you've made, um, and where you guys are now, looking back in hindsight's 2020.

But what would be what are your like the top two things that you look back and you're like, shit, should have done that differently? Yeah. Pretty much every pivot that we made, there's gone on to be a a huge company in that space who did great with it. And that's what's crazy to me, right?

Is like I thought when we pivoted, there's no way this is gonna work. And yet time and time again, you know, we were proven wrong. Except for Tinder for co-founders. No one's ever done that.

It's a shitty idea. I maintain, don't don't do it. Don't do it. Um, and so there's something about timing, which is out of your control.

Uh, there's something about grit and perseverance, which is in your control. Um, and I think that the hardest founder sort of problem is this pivot or persevere, right? Persevere means you just sit in your filth and you suck it up and you keep iterating and growing. And then pivot means you just thrash around until you get lucky and you jump on a gold mine.

Um, and I think that's just a really hard thing. So, uh, you know, when I look back, uh, I would probably just tell myself, whether you pivot or whether you persevere, you're believing in yourself and you're gonna make it. And and that is just sort of a self-confidence thing that, I mean, I remember weeks on end where I was just paralyzed with sort of this guilt and shame and anxiety. I had this like dry heaving problem, like every morning I'd wake up and the first thing I do is like run to the toilet and just like dry heave for a couple hours.

And I just like, I wasn't sure. Should I pivot or should I persevere? Why isn't it working? I thought I'd be Elon Musk by now.

Um, you know, but it's like two years in and like I haven't made a dollar for my company. Um, and so yeah, I think that, you know, lesson one is just more of a self-care one, which is just like believe in yourself, you're gonna figure it out, you'll keep iterating. Um, and as part of that also, telling yourself, it takes a long time to really understand your space. Now, I'm, I'm a product person coming into a sales and marketing world.

I didn't know anything about sales and marketing. So you have a leg up if you've like been an SDR or an AE or a head of sales before. But, um, it can take like two years to really deeply understand your space. Like, I remember the first time somebody told me what an SDR did.

And I was like, that's a real person. Like, what? Like, weird. Like, why would they do that?

Um, and then like, then but even a year later, I still didn't really get what it meant to be an SDR and so I started cold calling myself and then I'm like, okay, now I understand this stuff is. Uh, so it takes a while to understand your space. And understanding your space is very key to more quickly, you know, iterating through the cutting through the noise and bullshit to see if you can build something. Though being an outsider is good too, because being an outsider allows you to look at things differently.

Like I came in to sales and marketing and was like, why are we cold calling, you know, like why don't we just use the warm leads? Like you know what what's up with that? And so that like, you know, snowballs you into a new way if you can bring in that outside perspective. So it's pros and cons there.

Um, what's my second hindsight is 2020 lesson? Um, I think it's just it's probably like never stop taking customer calls or prospect calls. I think that oftentimes when things get hard or no one wants to buy, you retreat into your shell and you're like, well, I'll just like work on the product for a couple of weeks, or I'll just go get a a patent on my cool idea or I'll, uh, buy buy a latest domain name because .ai is hot.

And it's like, you're just working on shit that's not really moving the needle. Um, but you can move a lot faster if you're constantly on on the phone with with people. Um, prospects, customers, like I try to jump in on five customer calls a week. I try to jump in on five prospect calls a week.

I listen to, you know, um, our outreach Kai recording. I listen to our fathom CS recordings. Like, you just gotta hear the people talk. And like you get new ideas every single time.

Um, and you you'll always surprise yourself at what you can learn, um, but you just gotta keep that ear ear to the customer. I think that's one of the most important things like said in the podcast. Like, too many founders or revenue leaders or whoever it is, like they're like, I don't know whether they think they're too good for it or they think they don't have time. But back to the excusing, like, you gotta prioritize that.

Just like you would like training for a marathon, you gotta do the same thing. So, Yeah, here here you well said. And I think the the thing that I've realized is, um, as scope and complexity scales, you believe that you, whether you're a revenue leader or a marketing leader or whatever, you're you're trying to be a lot more strategic because you can't do everything, right? You used to be able to write every social post, you used to be able to review everything.

And then there's just so there's people, process, tools, you know, ads to manage, SEO to manage, like there's so much going on that you're like, okay, I need to be more strategic. And then you say, okay, well, if I'm being more strategic, I can't take these little meetings that are like not really gonna move the needle because they're not strategic. And so you take a step back and you're like, well, I just need to do things that scale. But like the classic founder lesson is do things that don't scale.

And part of that should be like three, you know, you know, prospect meetings a week, 25 cold call dials a day. Like, you know, these these don't scale. Like don't they're they're not. But they're interestingly, very strategic because it allows you to keep your ear to the ground to figure out what's going wrong within your org.

Um, and so, yeah, I I think that's a lesson for really anybody that, I didn't got to remind myself, which is like, yes, you can be very strategic in your role, while also being very on the ground and getting tactics done too. Yeah, I love that. I love that. 100%.

All right, let's, um, as we wrap it up here, let's move to some rapid fire. Um, ton of ton of cool knowledge dropped. Um, totally probably gonna post tomorrow about a supermarket or lettuce. Um, that that one's gonna stick with me.

Uh, all right, Max, early bird or night owl? Uh, it's supposed to be rapid fire, huh? Night owl. If you weren't in tech, uh, what like trade or uh, other industry would you be in?

I love Middle Eastern politics. I'd like to work for the UN and solve Israel-Gaza. Someone has to. That might, that might be the best answer we've gotten, um, so far.

That that that's a good one. Um, what's your favorite guilty pleasure snack? Ooh, uh, candied pineapple. Nice.

Yum. And the follow up on this question because I bet when you're doing ultramarathons, you're training really hard and you're watching your diet really closely. But when you get done, what's the first cheat meal you uh, you go hit? Oh, good one.

Chick-fil-A. Chick-fil-A, nice. Sandwich or nuggets? Always sandwich.

Spicy or regular? Regular. You go spicy? I do I I do go spicy.

Chick-fil-A does have the best milkshakes on the planet. I do go spicy. Oh, they're so good. They're so good.

Anyway, so, like, his spice is like, barbeque sauce. Okay, so that is not true, uh, at all. Let's go look at the hot ones tape we did. Yeah, stop.

Um, Max, what's the most used emoji in your, uh, in your work slack? I don't think you're gonna be surprised to hear that it's the cowboy emoji. You guys have the cowboy hat. I love it.

Awesome. Last one is wrap this up. Dream vacation destination. Ooh, uh, Iceland.

Iceland. Nice. Very cool. Very cool.

Max, thank you so much for joining. Uh, it was great to chat with you. Y'all, go check out Warmly. If you want to get those warm leads and actually convert them, Warmly.

ai. Check it out. We use it. Our customers use it.

Uh, it actually works, which is pretty damn cool. Great to be here. Thanks. Thanks, Adam.

Thanks, Dale.