#075: How Alex Song Built Proxima and Raised $12M Solving DTC’s Biggest Problem

If you really want to be world-class, I think you have to make these investments and shifts. And one thing that really helped me was just opening my mind to, to executive coaching and also therapy. There's so many other layers that power you through what we are all so focused on optimizing around, which is our careers and our achievements. And I think, you know, if you look at what we consist of, Physicality, our bodies, mind, our intelligence. But we also have this emotion, which we often have been told in business life, you just got to, like, put it in the closet and, like, don't let it out because emotion's bad. But there's also, you know, what I call this kind of spirituality, which, as I've gotten older, I understand it's not a religious thing, but there is some feeling of, like, greater purpose connection that it happens and it elates you and it makes you feel just so much more driven. And when things start to build, you get this momentum. You really lean into that power. And I think therapy, coaching, mindfulness retreats, a bunch of things that I've explored over this last, you know, 5 to 10 years have made me a better entrepreneur because it rounded me out to understand so many other parts of how to be world-class in managing people. I'm not world-class today, but I'm, I think I'm getting there.

Welcome back to Season 3, Episode 18 of the Turning Pro Podcast. Today we have Alex Song, who's the founder and CEO of Proxima. Thanks for joining us today, Alex.

My pleasure. Thanks for having me.

You still got the energy to build. I was reading a little bit about your background. It's like the amount of companies you've built and sold and some failed and some didn't, but you're, you're still going.

Why? A great question. I mean, I think for me, I'm addicted to the drive, to the grind. Um, I can never see myself just kind of sitting back on a beach doing nothing. I think the zero to one is super exciting. You know, you just kind of— you solve so many complicated problems that feel so insurmountable to maybe even me 10 years ago and a lot of people today. But once you've done it a few times, it's like, you know, climbing a big mountain, right? It's like the next mountain feels very doable if you have that one mountain under your belt. And it gets really addictive, right? I think I've had friends talk about marathons and triathlons in a very similar way. Like, I randomly got pushed into a triathlon by my friends 2 years ago, literally didn't train. They just kind of like gagged me and said, you're coming. And I'm like, okay, whatever. If I finish, that'll be remarkable enough. And then since then, having finished that race, I can do all sorts of random competitive events and just, I'm not scared about it. Right. So similar to your question, addicted to the drive, addicted to all the excitement that comes out of it, but also just feeling way more comfortable with the discomfort of building and being an entrepreneur.

Do you ever get used to the hour-to-hour, day-to-day, week-to-week whiplash of good things happening, bad things happening?

It's funny if you say used to it as in having this like non-reaction. Yeah, I guess I'm there as I think about it. I don't think about it honestly. What I've trained my brain to think, and I really encourage my team to think this way too, is like truly every problem is an opportunity. We signed up to build startups, which is literally foundationally a bag full of problems every day. And you just reach in and you pull one out and you hope that next day you have less problems. Or at least new problems to solve. I think having that energy, having that approach, you minimize the feeling of like good versus bad and you're more focused on like, okay, cool, this is what we do. We're going to train today. It's going to be hard. We're going to grind and then we're going to be better tomorrow. Right. And the more you can kind of remove the, the emotion out of it, I think the stronger you can sustain an ongoing effort to like keep wanting to come back for more.

My hunch is that as you've gone on this journey of building multiple companies, your ability to minimize the volatility and your emotional reactions to things gets like way smaller. So I think young founders, when something great happens, they're like a 9 or 10, and when something bad happens, they're like a 2 or 3. And what I've, what I've seen from founders who've been there before, it's like you find a really good way to stay between 4 and 6 all the time, no matter what, because you've seen worse days and you've seen better days. And I feel like that's a trait that you can't really learn any other way than with time and battle scars.

100%. And I think, look, I'm now 40-plus, right? Turning 40, turning 42 next month. So I think my first 10 years I was in finance, it just kicked my ass and gave me like this incredible threshold for pain and suffering. Having done investment banking at Goldman, then moving to their private equity group, then going to work for Bill Ackman. Like, intense. First 10 years of my whole career were just like getting the shit kicked out of me left and right, but then building this really strong tolerance for it. I would say years 30 to 40, I started to learn a bit more about like, how do you manage your emotional wellness, your mental well-being? Like, and suddenly what used to feel like, okay, I'm just at an 8 to 10 all the time, I was able to shift that down to a 4 to 6. So in one way, yeah, like for sure, I just got some sort of threshold for the pain and the challenge and developed more of a tolerance. But there was also a shift in the way I approached the challenges, the grind, the difficult moments to where I was able to restructure the way I felt emotionally and mentally when things went wrong that made it much easier to sustain longevity in this game, right? So now I've been an entrepreneur for, call it, almost a decade. Problems I thought in year one were like terrible, like, oh my God, we're so screwed. Like, life is over. My investors are going to kill me, are now like a Tuesday, right? So again, it's, it's adjusting this over time. And I think it's, it's really helpful to have that perspective and be able to say, all right, it isn't as bad as it might seem. It's going to be okay.

Are there specific actions you took or, I don't know, going to therapy or working with an executive coach that helped you get there? Or is part of it just like you just got to do it and it's reps and you kind of just get used to it?

For sure. I've gotten professional help. You know, I think someone once told me like, look, what you're trying to do, Alex, if you want to be successful in startups, is you want to be world-class in entrepreneurship and you want to be world-class at managing humans to build companies, right? Those are literally what you're focused on. And you look at anyone in the world that's world-class, whoever that might be— Roger Federer, Nadal, Djokovic— because we're during the US Open, they come to mind. They all have the best training in the world, right? You look at LeBron James—

you see the house— not to cut you off— do you see the house that Djokovic stays in for the US Open?

The one with all the crazy wellness, like all that stuff?

No, it's got, uh, 4 tennis courts. It's a house in like Jersey, I think, and it's got, uh, 3 outdoor courts, each different ground. One's clay, one's grass, whatever. And then it also has an indoor court.

Wow.

And it's some like, I don't know, rich hedge fund guy or something who owns the property, and Djokovic stays there for the duration of the US Open.

That's commitment, right? He's just like, he's living tennis like every freaking day and And that's the kind of thing like where if you really want to be world-class, I think you have to make these investments and shifts. And one thing that really helped me was just opening my mind to executive coaching and also therapy, right? I remember, pretty personal note, but I think I'm— we're at a good place now. We could talk about it. My sister's a life coach. She used to be in VC. She was Forbes 30 Under 30, Yale undergrad, Harvard Business School. And suddenly after this incredible career, She's like, I want to be a life coach. And I'm like, what? That's crazy. You're on this incredible trajectory. She's like, no, you know what? I like helping people. And I think the best part of my job as a venture capitalist is coaching and supporting entrepreneurs to be successful. I'm like, okay, great. I was kind of dismissive of it. And then she pushed me. She's like, look, why are you scared of having therapy or coaching? And I'm like, I'm not scared of it, but like, I just don't think I need it. I think I'm pretty high performing. I've done pretty well. And I'll tell you, once I opened my mind initially just to prove her wrong that I didn't need it, but I took the, I took the intros and I had the, the conversations. Wow. There's so many other layers that power you through what we are all so focused on optimizing around, which is our careers and our achievements. And I think, you know, if you look at what we consist of, physicality, our bodies, mind, our intelligence, but we also have this emotion, which we often have been told in business life, you just gotta like put it in the closet and like, don't let it out because emotion's bad. But there's also, you know, what I call this kind of spirituality, which is, as I've gotten older, I understand it's not a religious thing, but there is some feeling of like greater purpose connection that it happens and it elates you and it makes you feel just so much more driven and when things start to build, you get this momentum, you really lean into that power. And I think therapy, coaching, mindfulness retreats, a bunch of things that I've explored over this last 5 to 10 years have made me a better entrepreneur because it rounded me out to understand so many other parts of how to be world-class in managing people. I'm not world-class today, but I think I'm getting there.

You mentioned earlier on, I think in the first response, that you didn't want to go sit on a beach somewhere and that this is really kind of your calling and your craft that you really got obsessed with and that you really enjoy and fulfills you. I'm curious, was that learning— did you always just know that's not for me, or did you experience that, like maybe made a bit of money, took a couple months sabbatical, and then realized, oh, this is actually not for me, this is not fulfilling?

So I grew up with a father who was a serial entrepreneur. I'm first generation. He emigrated to the States in the '80s. He was part of like the semiconductor rush. Silicon Valley was like coming over and like, you know, building microprocessors and soldering motherboards, all that stuff. I literally saw that growing up. And he then tried to build multiple companies and it was a grind for him. And in relation to your question, we never took a family vacation to a beach until I was 16. So I literally was like, that was just not something we did. So I had this idea of like, okay, cool, you're gonna work hard and then you get to go on beach vacations, right? It's like, that's literally how it computed for me as I was a child. And then as I got older through my early 20s till, you know, almost 30, I was in like high-flying finance. I was making over 7 figures. I'm like, okay, I'm doing the thing. I'm in New York City. I'm, you know, whatever. I was a finance bro, whatever you want to call it. But I was like, okay, cool. Now I get to take the vacations. I get to do this thing. And I did take a sabbatical after my first 10 years in finance. And yeah, I enjoyed it. I saw a lot of places that I'd only read about or heard about, and it was great. But at some point I was just itching to do more stuff. It just wasn't what was satisfying me. And I actually went on this really interesting journey of just learning things, and in particular, learning sports, learning things that, like, for example, I got super into surfing. I got really into kitesurfing as well. And it's like, okay, to do that, I get to travel and go to these different places. But as you do these things and you start to, like, have the downtime to just think about, like, where does your mind go, where does your heart actually want to spend its energy? I wanted to build, like I could tell, like I had seen so much entrepreneurial energy through my life that if I didn't go embark upon that myself, I would regret it forever. So then I piled myself into like doing this analysis over like, and I was a finance guy, so I did this like detailed analysis of all these different opportunities, categories, industries. And that's how I landed on actually building a holding company of direct-to-consumer brands.

What would you— I'm curious to know, like, how you think about boundaries as you've gone on this journey, because I, I feel like younger entrepreneurs are way worse at having boundaries because the world is ending every single day.

Sure. Look, when I was in finance, there was no boundary. You, like, literally had to make a reason very clear if you wanted to take a day off, and if you weren't, like, like getting married or attending someone's funeral, it was like frowned upon, right? So it's like there basically were no boundaries. It was just like your time is invested into making money for the company and therefore you getting rewarded. I think as I got older, in particular when I went through COVID, I started to really open up my mind around like personal versus work-life balance. I never thought about work-life balance. I just thought about work hard, play hard. And when the harder you play, then that's your personal time. And like, there you go, you had it, get back to work. During COVID the world stopped, right? And like the way you spent your time and the way that your team spent their time became very divergent, right? Like some people were very scared about meeting in person. Some people didn't want to do certain things. And quite honestly, you also had this moment of like the great resignation shortly after we couldn't afford to not respect boundaries because we needed to retain talent. And it really opened my mind up, plus the personal work that I was doing, to understand like, oh, here's what people care about, here's what they need, here's what their families need, their responsibilities. So I would say at this stage of my career, I am way more empathetic to boundaries. That being said, transparency and communication are key. Like, that's how you get comfortable and that's how you trust people to set healthy boundaries.

What about even for you on a personal level though?

For me, I am very open about my failures today, my personal, you know, both professional and personal life. I'm very open about, um, and I think that just comes from growth and like feeling good about being vulnerable and seeing the other side of it. Um, I try to keep my family kind of on its own, kind of boundaries around that. I have a kid now. I got an almost 3-year-old. Crazy story. Born on my birthday 2 and a half years ago. So we're sharing a birthday in 25 days. That math was wrong. 2 years, 11 months ago, he was born. We're about to have shared birthday. It's September 28th. But I try to still sustain some boundaries around that just because it's so precious. And like, I don't want to influence, you know, my child in weird ways if it's like, oh, he's getting too exposed of like, I don't know, whatever it might be in the crazy streets of New York City, right? But outside of that, I think I'm more open than ever, like just giving a lot of my team insight into my personal life. And I also think truly in this generation that is currently coming to age in terms of their professional life, they want that. They want that connectivity. They wanna understand who I'm working for, how they spend their time. And that connectivity in a world where everyone is seeing more about people's personal lives, or at least the social media version of it, more than ever, it's really important for leadership in a company to be open to how you live, who you are, what you stand for more than ever.

I want to talk about leaders at your company. I feel like I'm only 2 and a half years into this and we've known each other for 6 or 7 months. And for the first couple of years, we didn't have an executive team. 6 to 12 months ago, we finally hired, you know, real VP of Ops, VP of Content, and CRO. And increasingly, I'm realizing at the advice of some executive coaches that a lot of my job is to build them up as people leaders. Talk to me about the importance of not only hiring leaders and executives, but how you see your role in building them up as leaders of their own teams, especially as Proximist is scaling.

So important, right? I think that as you scale, you're always looking for other leaders to help you in areas of expertise that you currently don't have, that you're craving and needing in your organization. But I came to this same, you know, mistake recently, right? We, we raised a Series A, raised $12 million earlier this year. I'm starting to hire more senior people that have expertise in things that I don't know much about. I'm no longer the smartest person in these areas of expertise. And I often am like, okay, great, run with it, handle it. But if I'm not staying as a constant, as an anchor, as a centering point of like strategy, vision, where are we headed, purpose, and then guiding the evolution of how that person puts their mark and footprint on an organization, it's not going to go well. And we've had that experience recently. And it's not to say I'm like, oh, I'm taking your toys away, right? That's not the attitude I come in with. But I come in with a much more like collaborative, let's be successful together. Let's spend the time, let's understand how to get alignment. And then as they start to excel and they're like really aligned with me and executing well, great, run as hard as and fast as you want to. But I'm here for you as a support system, as a sanity check, as someone that is going to continue to hold accountability because that's part of my responsibility. And more important than ever, I'm really focused on just KPIs and metrics where if you're doing the thing that we agree on is the thing you need to focus on and it's going in the right direction, awesome. I give you a lot more space to operate and execute. When you stop hitting those metrics or we're having some bad quarters, it happens. Don't be shocked when I lean back in and we start to figure these things out together.

How has your philosophy around identifying and bringing on elite talent evolved over the course of your career?

Really good question. So in the beginning, when I, let me go all the way back. So I leave finance. I think I'm so smart, you know, I'm like arrogant as hell. And I basically come in thinking like, oh, all these jobs, you know, they seem so easy. I'm like, I can do most of them, but I'll hire people that really do the things that I don't want to do.

Right.

So it's like, okay. I thought I could do Facebook media buying, for example, for a time. And I was like, ooh, but I really don't like staring at a screen, like clicking and setting up campaigns. Like, oh, just hire someone, right? Like, great, fill this in, get an agency, whatever it is. And that used to be something where I'm like, okay, get the best person in place and have them do the thing that I don't want to do so I can quote unquote stay in my zone of like genius or excellence. What I realize when you scale though, is that when you hire people that do things that you don't like to do, or that you do things that you don't understand how to do, such as computer coding, et cetera. I'm not a technical founder. And when I bring those people in, it's actually really hard for me to manage them because I don't actually understand what they're doing day to day. Right. And there's like so much more trust that has to happen. I have to get really, really accurate on the hiring. and when I don't hire accurately, which by the way, we all as business builders will unfortunately hire more often incorrectly than, than amazingly accurately. That's just the odds of what happens. When that keeps happening, you now are surrounding yourself with more and more challenges from a management standpoint of things that you don't understand. So I've now taken this adage quite seriously, which is when asked, should you hire people that do things that you do well or do things that you don't do well? I actually flipped it and I started hiring people where they do things I already do well because I can onboard them super efficiently. I can figure out very quickly, are they good or not good at the job? I can figure it out during the interview pretty much based on the questions that I ask. But if I'm like talking about, hey, your service— serverless architecture for your AWS setup on Databricks and how that's gonna move the, the, you know, the ETL motion around our data. Like, I mean, I kind of know, but I don't really know, right? So it's like, that's where I need to spend more time and get more hands-on, bringing in advisors, consultants to make sure I get those hires correctly. But when it comes to something I know how to do, which is generally more on business development, operations, commercials, finance, those sides, those sides of the business, I fire quick, I hire quickly and accurately and I fire very quickly and accurately because I just know it so much better.

As you think about kind of the state of early stage B2B go-to-market, this is something that we're both pretty heavily involved in. Pre-seed, seed, it seems to be a lot of hand-to-hand combat, hopefully some referrals, hopefully some benevolent network introductions and probably some targeted BD on your end. Obviously raising a $12 million round. Now you're looking towards repeatable acquisition vehicles. Could be growth, BD, sales, marketing, whatever it is. So walk me through that transition there from what you did in the early days of Proxima to, okay, we have capital to deploy. What are the channels we can repeatedly deploy into?

Sure. I mean, we're going through right now in a big way. And look, in the beginning, it's all hustle, right? It's just like, you know, you're leveraging every relationship you have. You're calling in every favor you possibly can call upon, and you're just trying to turn a dollar into as many dollars as possible day in, day out. And the more that you can do without actual cost of acquisition or investment, the better off you're going to be. Now, I think there's this balance, right? Which we're now a Series A-backed business. We raise a ton of money. We're supposed to show up in this like, oh, you know, you're center stage at the conference. You got the big booth. But like, that's a trap in my view because there's some level of that is like you're just fulfilling your ego, right? You're just trying to satisfy your need to show up and be like, look, we're big, we're amazing. But the truth is ROI is more important than ever because it's so competitive today. Every brand out there is being just inundated with like every possible offer for every B2B solution that, you know, they could possibly, they're like, they're swimming in it. They're getting invited to these like dinners and like race car driving experiences and like hot air balloon. I don't know. I've heard some crazy stuff and I'm just like, no, you, you gotta just really focus on the best channels that are most scalable, that are most repeatable, and then lock those in. And if those are profitable, then start making bets on other channels. Go a little bigger here, try this location here, you know, whatever geography you haven't tapped into yet. And it's honestly not that different from how you build a direct-to-consumer brand, right? Like you gotta figure out Meta, you gotta figure out your UGC. Now you gotta figure out, you know, if you're on Amazon, you gotta figure out Amazon, Google search. It's like you have this core playbook. Okay, great. These are optimized, they're profitable, hopefully giving you cash. Go take a bet on TikTok. Go try some outdoor ads. Like, but don't do it until you get the core things correct, because otherwise, how are you sustaining your business? Right? It's like that kind of mindset. I learned a lot from that, and I think that's helped guide me as I think about marketing and scaling Proxima.

I think something you've done that's really admirable that I don't think a lot of people can do is go from the brand side to the software side. I think there's people who always talk about doing— they're doing one and then they talk about doing the other, where it's like the grass is always greener on the other side. It's like you talk to a SaaS founder It's like, why didn't I just start a brand? And then you have a brand founder who's like, I should have just started a software company. I'm curious, having been on both sides of the coin, what is your perspective on it?

I love that you bring this up because I have a friend, my only friend, crazy enough, he went from software to consumer brand, has a, has a strong AI component to it. So not completely just consumer products, but like it's not an easy transition, right? And I think I was struggling with it for quite some time. I think what helped me in, in my journey from consumer to SaaS and data intelligence founder is the fact that the problem I'm solving was always one of my biggest problems as a D2C founder, which was customer acquisition. It's, it's literally the lifeblood of your existence. Your, your LTV to CAC, that little ratio that gets thrown around in every board meeting and every deck, it actually is super important. And it's a never-ending battle to try to optimize it as a, as a D2C founder or operator. What I saw when I moved over was like, okay, I'm actually trying to build something that helps me help my brands. Like that was the, the first iteration. I wasn't setting out to build a B2B software initially. I just wanted to build something that made me have a technology advantage And what I did was I created this data intelligence solution that brought the data of brands together so that we could actually power targeted customer acquisition better than we could do on our own. So strength in numbers, right? We did this over and over again. The reason why I had a competitive advantage is that rather than being a B2B sales guy saying, hey yo, if you gimme your data, I'll give you some CAC. Reduction, it was like, hey, I have 3 brands. If you pull the data with me, I'll give you access to all my data. We're never gonna target directly. You get to control it yourself through your channels. But that combined data signal is just so much smarter. Then suddenly we're doing that since 2016. Suddenly iOS hits in 2021, April 2021. Suddenly all the data I have is super valuable because 60% of people are opting out of having their data on their mobile devices go back to Meta, Google, Snapchat, et cetera. All the places where the customer acquisition's happening. My 70 million US-based shopper personas were like, I literally can see what they're buying, how much they're spending across all these different categories, has super powerful signal to give you better targeting. And then that's when I realized, oh shit, this could be its own standalone business. Put it into a business we now know as Proxima, and very fortunately got the Series A round locked up just this past year after being founded just 2 years before that. So I wouldn't say it's easy. I would actually say for me it was like an 8-year journey to get there, and it was very reliant on the fact that I was solving such an important pain point that I lived with for so long that I could actually get the execution correct.

What was that conversation with your co-founder on the brand holding company when you're like, this thing needs to live on its own?

Always challenging, right? Because when you, when you have divergent ideas around how you want to spend your time, you know, you're going to have some hard, hard conversations. I think for me, we have built so much trust through the years having built this business together, having built and sold a business together, and also having him be a meaningful equity partner in Proxima, right? So he feels good. He's not day-to-day at all. He's still a confidant and advisor, someone I look to for advice because he's super smart and just has really great perspective. But he's also at a point after we had the exit, he's doing a lot of work still on Finn, our pet brand. And he loves this new role that he has where he's advising a lot of different companies, some of which are, you know, multi-series-backed VC companies now that he was very early on. And then very fortunate for me, we continue to invest together. Now that we've had a little success and we had an exit, we have this fund that we invest out of, just him and I together, equal partners in it. And we source deals and we just love working with founders, right? Like sharing our knowledge, sharing our experience. And we deploy, you know, meaningfully for, for two guys just working on the side, like real checks. And I think that's a great evolution of our relationship and how we stay today, just amazing partners and friends.

What are you most excited about right now in the ecosystem from an investment perspective?

I will not say AI, I promise.

Thank you. We don't have to end the episode.

I love consumer. I know it's crazy, right? Because look, consumers had a really tough run. A lot of people today that used to feel like the capital markets were available to them or the venture markets were available to them, they can't find funding. It's completely dried up. But it's almost like, you know, when there's so much negativity about something, and you could find the good businesses and take a contrarian view, there's a ton of opportunity, right? And there's this segment of the business today that like, they probably raised a lot of money at a really high valuation. They're trying to raise more money now, but because of how high the valuation is, the existing investors are like not happy that this is probably going to be a down round. They're not profitable yet, but they have like built the brand. They have, you know, they're over 8 figures and they're just not raising capital, right? It's just, it's really hard out there. I love talking to these opportunities because if they're close to break even or on their way to profitability, but all those great things, there's real business opportunity just from an investment perspective. It may not be the huge like IPO that some of these businesses have pursued and arguably incorrectly, right? Like no offense to the Caspers and the Warby Parkers and you know, the bigger businesses, like they, they did what they had to do given how much money they had taken on and they had to, to pursue this like massive outcome to generate the returns that their investors expected. But for this new crop, like, hey, you don't have to be a half a billion dollar brand. You can get to $50 to $100 million of enterprise value and like, that's an awesome outcome. Right. I think there's an incredible opportunity in this segment, which I spent a lot more time thinking and evaluating through. And that to me is a, is a real ripe area of opportunity that today I think is just being overlooked.

I also think you have the benefit of not having LPs where you don't need to hit some like arbitrary return number.

Yeah.

Where you can actually just optimize for like probability of non-zero outcomes versus probability of like returning my fund 100 times over, whatever the metric is. And I think it, it allows you to invest in certain businesses where you're like, do I think this is a billion-dollar outcome? Not necessarily. But do I think this is going to zero? No.

Exactly. That's exactly right. And, and look, I love being in the game, right? Like, I'm a B2B founder that is also servicing this huge segment of direct-to-consumer e-commerce brands. And I think when I could be supportive, and a lot of these people raising money are my clients and I'm like in their data, I'm like looking at their metrics.

I'm like, he's got the best diligence vehicle of all.

I'm like, dude, your, your, your ROAS, your, your, your return on first, you know, on, on your customer, your new customer acquisition is amazing. It's like top quartile, top decile. And it's like, great, let me help you raise some money. I have a network. Let me put some money in. Like, I'm not saying it's easy because I know a lot of people are in this boat right now and it's hard out there. But I do think, you know, what my encouragement would be is like, the good businesses still have a valid reason to receive funding. It's a moment in time. There's too much of just putting like this big, you know, label on everything is bad and negative and going out of business. Like, stick with it, keep your chin up. And Come find me. We can have a conversation. Yeah.

It does seem like there's a new crop of consumer founders specifically that are kind of our age. We're 28, right? Yeah. That are kind of our age that started a couple years ago.

Yep.

That are incredibly capital efficient and just running like really impressive. Like Dan at Create, they just announced the round, of course. Um, Andrew from Moon Brew. Uh, Jolie obviously is more experienced, but it does seem like even though I'd say that's still the dominant headline of like e-commerce investing is dead. There's a lot of like impressive capital efficient founders building right now that are a couple of years in.

But I would say one of the things that makes me laugh about it is when you get caught up in like the DTC Twitter world or LinkedIn world, you almost believe that there's only like 50 brands on the planet because it's like the noise. There's so many businesses that you just like don't hear about that are crushing. Dude, I talked to a, I talked to a consumer investor, the consumer investor the other day. Who was just talking to me about one of their brands in their portfolio who could use some help with their website. And he sends it to me and they sell like umbrellas. And I'm like, okay, like cool, I guess. It's like, oh yeah, it's a husband and wife. They're gonna do $60 million this year in top line. And I was like, what the fuck? Like, but it's because you don't hear about them like screaming from the rooftops. So there are a ton of capital efficient businesses out there and ones that do really well. They're just not making noise. They're like moving in silence. So it's kind of on you to just sift through the noise and find those types of people, but they exist for sure.

And honestly, like, there is something about the way I was brought up in the finance world where I like this, this more low-key approach to building businesses, right? A lot of, because of social media today, there's a lot of like building in public and like a very, I don't wanna say beating on my chest, but very like, look at me, look at me, look at me. Like, good or bad. Look at me, look at me. That's fine. It works. And there's definitely a place for it. And I have friends that I really like and I find very endearing, but they're taking that route and that's cool. That's them. I think for me, like, you gotta find the balance that works for you. And to your point, you can be super successful and under the radar and it's totally great because at the end of the day, the results are what matter. Right? I think that's the big, the big focus for me of like, where do I wanna show up? Recently I definitely made a push on LinkedIn. I'm learning from guys like you, like it works, right? It's, it's business oriented. But then finding your voice, finding your balance. I think especially in this ecosystem today, you gotta figure that out because you can get pulled in so many directions so many quickly just because of all the other noise that's happening.

I'll caveat one thing though that I think the industry that you're going after or who your customer is makes that very different because it doesn't make sense for a consumer founder to be screaming LinkedIn because you're getting one customer to buy a $30 item.

Sure.

Like, I personally believe— I'm very loud on LinkedIn, I'm the first one to admit it— but I personally believe that any B2B founder that isn't doing it is doing themselves a disservice.

Sure.

Because when you think about time spent to potential outcome of it, because you have like real contract values and it only compounds, it seems like a no-brainer to me.

I agree with that. But I think even in that of like Having presence, the how can be very—

yeah, there's a, there's a wide spectrum of what your presence is, don't get me wrong.

Exactly.

But I think having no presence is really silly to me.

Completely agree.

Uh, because I think the other thing about it is that it compounds, right? Like, sure, does your personal brand benefit as a byproduct of like, watch me build my company? Of course, because there's people who are going to start to watch you, and then as a proxy, they're also seeing what you're doing with your business.

Sure.

But like, that just gives your business more leverage the further down that path that you go. But I think you hear this joke so often of like the loudest consumer brand founders are those where their consumer brands are struggling. And so now they're selling like courses and newsletters and whatever.

Sure.

Because they're trying to like generate dollars in their pocket. But for B2B, it's kind of like you're trying to sell a customer.

It's almost table stakes at this point. Yeah, exactly. If you're not doing it, it's like, what are you hiding?

Surprised if you're not doing it. Yeah. I want to talk about early days in finance and what you learned.

Please.

For, for context, we— Claire, who's our VP of Ops, I think you know. Yep. Did her first 2 years out of BC at Morgan Stanley. And I always thought I had like a grind work ethic, founder working all day. She came in and was just like out, like running rings around me. Like I'd get on at like 6:30. She's been on since 5:00 AM and just every day. And no like rushing, anxious energy, just focused.

Yeah.

All day, all day, every single day. Doesn't, I think she's taken one sick day in like a year. And it's just a mentality. And she's never burned out. She's always on top of it. And I've just been so consistently impressed. And I know that's just a fraction of kind of the work ethic and as you mentioned, the pain tolerance that you learned.

Sure.

And so I'm curious, I wanna talk about those first 10 years. Like what was the first couple of getting used to that pain tolerance and then kind of leaning into it?

Happy to. I'll try not to have any PTSD. But look, I have a very, fond memory and perspective around the first 10 years in finance. And, but that being said, I sure as hell would not want to be there right now because what I believe to be so valuable about those experiences when you're young is it sets a foundation. It sets expectations of how you want to carry yourself, who you are, what you want to stand for, what your work ethic and integrity looks like. And if you don't get that embedded in you in a, in a younger time of your life, it's super hard to ingrain it later in life. So I know, like, even today, if I have this massive opportunity with some big enterprise customer tomorrow and I gotta pull an all-nighter to get that deal in by the morning in order to like meet their RFP requirements, I'll do it. Like, zero question in my mind. I've done it before, I'll do it now, right? And but do I want to do that as like a regular thing? Hell no. But that was a regular thing back in my finance days, right? Like, at Goldman, if I was getting out before 10 PM on a Friday, I was looking over my shoulder like I was escaping from a prison, right? It was just like, oh shit, I hope no one sees me. Like I would take the one exit that's like away from my boss's door and like there's no line of sight. 10 p.m. on a Friday, right? If I could get— my rule was if I could get home in time during the weekday to see the midnight broadcast of SportsCenter, I had, I had a good day. I was like, oh wow, like I had an easy day.

I just like hear these stories and it's— I do believe, I do believe that a lot of people struggle to empathize because you hear it, it's almost like that's hard to actually fathom. And then it's like until you're in that position, you can't relate. I would say my closest comparable to that, cuz I gave up my corporate job 12 hours before my first day and I never made it.

Oh wow.

Um, cause I was like, this just isn't for me. Like I, I went to a very corporate heavy, I went to Colgate University and it's like very much like go into banking or consulting.

Yeah.

And I got the job and I was like, wait a minute, I don't wanna do this.

Yeah.

That's all to say that I think the closest comparable you can get to finding someone that will give you the same level of like drive and competitiveness who didn't do the corporate thing is athletes. Agreed. Like, I didn't go into consulting, I didn't go into banking, but because I was a Division I hockey player and like grinded my entire life in that level of competitiveness, like, I'm going to beat you, I don't really care how it happens.

Exactly.

There's something to be said about that. You might not have the best— you might not have the same like technical skill set of like building a DCF at 2 o'clock in the morning or whatever. But I sure as hell know that based on my will to win, I will find a way to solve the problem. I just might go about solving it in a different way than the guy next to me.

And that's why I love hiring athletes that have performed at a high level, because that type of competitive mindset, that kind of willingness to suffer and endure in order for a bigger purpose— you cited winning, but other people cite financial outcomes, changing the station of life for their family, being able to do things for their parents, whatever it might be— that drive is so hard to learn later. In life. So if you can get it from being an athlete, you can get it from doing an investment banking program, you can do it from going to the military even, right? Like, just how do you want to win? What do you want to stand for? And how do you connect with a purpose and be willing to do the hard work? Not just talk about it, but like really do the hard work even when no one's recognizing it, no one's applauding you for it, but you're just driven to achieve the outcome. That's so powerful and so valuable. So to your friend, sounds like a really great hire. She's locked in on that. Like she's built it into her rhythm. That's what she stands for. And that's amazing. I will caveat on this side though. Even when you have someone that's just so steady like that, burnout is a real thing. I used to laugh and be like, burnout? Fucking losers. Yeah.

You're soft.

Yeah. You soft motherfucker. Like, no, I'm sorry. Like that's how I thought about this.

Yeah.

Yeah. But As I get older and I understand like there's bigger things in life, like as a 20-year-old that's like single in New York, you're like, yeah, like I don't have a lot of problems that I'm dealing with outside of work.

Like, what bar am I going to tonight?

Yeah, like, yeah, what bar? Like, okay, you know, whatever. I think it's a really good and healthy thing for me that I saw the other side of it. I felt aversion for it. I wouldn't say I had mental burnout or physical burnout, but I could feel that I was emotionally drained and almost numb. I had numbed myself to the point where, like, I wasn't feeling happiness. So, like, small side note, yeah, therapist taught me this: you have a spectrum of emotions. On one end, you might have anger, rage, all the sadness, which you consider bad, negative emotions. And if you think about it as a spectrum, you're blocking this side of experiencing it because you're scared of it, or you feel like some childhood angst associated with it. You just remove it from how you experience life. But it also means the mirror, the yin to the yang on the other side, happiness, jubilation, exuberance, like all these powerful, joyful feelings are harder for you to connect with. So I was having big wins. I was like, you know, having great financial outcomes. I'm like, Buying a car, I'm like, you know, things, whatever, things that I like, oh wow, one day if I could just do that, that'd be incredible. And it's just not, it's a nothing, right? It's just like, oh, oh well, or chase the next thing. So my version of it was really, really understanding that I had become almost emotionally bankrupt in some way. Like feeling things was not normal for me anymore. And it really helped me in my finance jobs where I was like, I can make really high-pressure decisions with a shit ton of money on the line and like not feel too negative about it. But on the flip side, in terms of personal growth, in terms of like things that are bigger, higher purpose, more meaning, I wasn't connecting to it, right? So just to watch out for me, for my own personal learnings, it's like, it's great to have that grind, that drive, like keep looking for that next mountain you want to summit. But hey, the mountains just get higher, right? At some point you, you're gonna look back and be like, where'd all the mountains go? And what do I have to show for it? And then that's gonna be a really empty moment that I have enough billionaire friends, celebrity friends, people that are super successful that I look up to and they're like, hey Alex, I've been at the top of the mountain. It's cool. I'm not saying don't go for it, but don't forget all these things that you want to carry alongside of you that are also important as well.

I think you just get caught up in it and you can wake up like years later and be like, holy shit, it kind of just passed you by and you don't think about it. For, for me, for better or for worse, we've had a couple of things happen within the business. Like we had one employee who overnight was in the ICU for 3 months, had a pacemaker put in.

Oh wow.

Very young, actually. And he was our first hire outside of our— like, out of— outside of myself and my co-founders. And when everything is going well and it's momentum and everyone's excited and then something like this happens, your first thought is, holy shit, like building a business, like, is trivial when you're sitting here thinking about, you know, what, what's tomorrow gonna look like as it relates to this person on a personal level, their family, their life, how it affects everyone else. And for better or for worse, it's been moments like that where it forces you to just like think inward and realize that like there will always be another business to build when you're ambitious and you're around abundance of opportunities. But being able to check in with yourself and recognize that you can enjoy steps along the way and like do other things to be present has been really important. I think a moment for me that was a big stepping stone, you know, because I'm a first-time founder, so like managing people for real, like this was the first time, uh, last week one of my direct reports who's been crushing it, like I've started to worry that he's gonna burn himself out. Like it's not me pushing him, I'm like, dude, you gotta slow down because this is like a marathon. I put a 4-hour block on his calendar on Friday afternoon and it said close your laptop and go sit in the grass. And I was like, get off your computer. Like, you're done for the— you're done for the week. Because he's, you know, he's pushing really hard.

Yeah.

And he didn't ask questions. And he actually— he went— he ran a half marathon. He like closed his computer and went, ran a half marathon. I was like, that—

I've like—

because I've seen these other— which is like crazy, but like, that just tells you the type of person.

Yeah.

But it's like, when I've seen these things happen with some of our other people, I realize that you have to look out for people even when they don't want to look out for themselves because they're so competitive and want to win.

Sure.

But if you don't check in along the way, like bad outcomes could happen.

I think that's really well said. I mean, I will touch on this point about like our professional lives versus like the heaviness of real life when we think outside of, of business. I had one of the hardest experiences I've ever had just as a human, but also as a CEO, which was we lost one of our team members during COVID She literally, God rest her soul, was one of the first—

I just got chills when you said that.

Yeah, literally. Imagine like one of the first few days in New York when like everything was happening at Central Park where like literally just bodies were piling up. I get this call that she had passed and she was like barely a year or two over 30. And it was the craziest thing. We're all on Zoom. With my team and to have to deliver that news and then really come together and grieve while we can't be in person was so hard. It was incredibly hard. And that was a really important moment for me that just helped me understand there's so much more to life and what we're doing. And also these humans, these team members that I'm taking responsibility for. There's such a deeper level of what I need to commit to them just by being in a business relationship with them, right? Like, there is real connective tissue that channels through what we do day to day. And look, not everyone needs to be like that, but that was an experience that I had that set me on this path where, like, when I think about purpose, when I think about mission, I think about my team in a really big way. I know that if my team's good and my team comes out and has great success, great outcomes, and their trajectory of whatever they want is better than it was before they work with me, I'm gonna be okay. Right? So if I focus on them and I focus on their outcomes, as well as focus on all the stakeholders and supporters of our business, that to me is a guiding light for me. And, and it really was that big. Really tragic moment for me that set me on that more understanding, comprehensive path of like all it is that I'm actually responsible for in life.

It's crazy because especially as a first-time founder, there's so many things that you can't plan for, right? Like you can't read a book about like, what do I do if this happens? And when it's just kind of you navigating the waters with, um, your co-founders, right? Like we had someone, I just told you this yesterday, it was like their first day on the job. They got a report that they have breast cancer, first day on the job. And I was like, we just went through this. Like, yeah, but it's you. This is what you sign up for when you want to build something and you want to take care of a team. And whether you like it or not, the extension of the team is their family. And it becomes this like thing that's a lot bigger than you, which I think is a driving force. And it's part of the reason that you will stay up till 4 o'clock in the morning to get the thing done because you know you're serving something bigger than yourself.

100%. And I would add to this, that's why I emphasize this connective emotional element of me being a CEO and founder. Like, I never really thought about how important it was to feel the empathy, connect to what's going on in your employees' lives, right? Like at Goldman Sachs, I was one of, I don't know, hundreds of thousands of employees. No one's talking to me about like how I feel on the weekends. Maybe I heard they're doing some stuff now. They're like trying to get— allegedly, allegedly, you know, like you can't sign on on a Saturday or like whatever they're doing. But at a company size of now, you know, we're 40 team members and growing. We're still small enough where I can really have that personal relationship. And it really matters to me, right? Like we probably overinvest compared to the average company around culture building, company activities. Both for remote as well as in-person. We do a bunch of like random stuff, trivia, escape the rooms, both, you know, for the hybrid teams. And, you know, just constantly trying to do things to the point where some feedback is like, guys, we do too much stuff. Like, it's like, I like you guys, but I don't need to do these things.

Can't make the pizza remotely with you.

Exactly. I mean, we literally were sending like cocktail kits to people that want to do like, you know, mixology class, but like again, trying to incorporate everyone to build that connective tissue. But it's also because I realize if you want to be successful in anything you want to do, it's the people that make that outcome possible. And the more that you can connect with those people, align with those people, and also really make those people feel appreciated, that you care about their outcomes and genuinely do care about those outcomes, the stronger you will be and the higher your likelihood will be of success. That's just how life works. We are humans. We like congregating with other humans. That's an important part of what we do. And I think as founders, that's a huge part of the learning curve, right? And, and the hard part is, you're right, you can't read a book about this. You can get some coaching about it. You can talk to other founders in almost like a AA self-help type environment, right? You can listen to podcasts like this. but really it's something where you just gotta get on the ground and have the experience, go through these hard moments, and then if you come out the other side, you're gonna just get better and better and better.

How do you think about, we talked about culture and people at the core of a business, and I think from our experience, momentum is easy when you're signing clients, things are going well.

Sure.

And then in the low points, I've been doing this like 2 and a half years and we're very market correlated, right? People are getting funded, they wanna push go-to-market, Content's part of that. But there's also been a ton of slowdowns over the past 2 and a half years. Sure. Every few months it seems like there's another slowdown in seed or Series A. And those are the moments where it's like you hop on an all-team call, someone churned that morning and the week before you didn't sign any new business and there's misses here and misses there. But you gotta show up and try to keep up that momentum. How have you approached that over the past decade? Because I'm sure there's been slower points where you still have to show up and try to develop that momentum.

I think it starts with transparency, and it's really about building trust over time. We have had our highs and lows, even though we've only been around now almost just under 3 years. You know, it wasn't a guarantee we were going to get funded. Right. And I like, I put that on my back and I was like, I gotta go get this done. And thankfully, even though it was a very hard first half of 2024, we got the deal closed. We got $12 million in the bank and we were able to then execute for this next stage of our journey with a lot of confidence. However, one thing I went through, which relates to what you just said, is because I'm a solo founder and because I had to go raise that capital pretty much on my own with support of my team for sure. But like really it was me managing and owning that process. I got disconnected from a lot of the execution in the business. I was not as close to the commercial. I was not as close to some of the technology decisions we were making. And I just couldn't be because I had to go raise the money so that we can even have a future to like, that these decisions even matter. Right. Over the course of this year, it's been a really important effort for me to lean back in, get closer to what's going on, guide everything that we're doing towards a unified vision, and most importantly, communicate that vision harder and stronger than I ever have had to do. Because what happens is post-fundraise, you have all these ambitions, all these aspirations, and then you're like, oh shit, I gotta deliver on some really high financial expectations. Then I go into this little bit of like, I guess it's a little bit of a desperate, or a desperate experimental mindset of like, okay, I gotta fuck test this, I gotta try this. And next thing you know, anyone that doesn't understand why I'm thinking about what I'm thinking outside looking in just is like, whoa, Alex is all over the place. What are we focusing on? We look so diluted. Like, we have a small team and we're trying to do so many different things at once and it gets messy and people lose conviction that the vision makes sense. So I've been on literally like an internal campaigning parade, right? Like the presidential election's happening in November. I'm like literally like doing my own little CEO election. You know, like no one's running.

Who's the winner, Alex?

I'll vote for you. No one's running against me, but I am campaigning hard to keep my job effectively, right? Ben, and I jokingly say it, but I am quite serious in that I'm going team to team and being like, guys, I fucked up. I got away from it. It's understandable why, because we needed the money. So like, it's not like I was just completely just being irresponsible, but hey, I see where this went wrong. I see that some of you are frustrated. The lack of clarity and confusion in our roadmap and our vision, et cetera. But here I am again. Here's what we're doing. Here's how we're gonna do it. And here's the people we need to bring on in order to execute successfully. Here's what I need you guys to do. And literally, I kid you not, I'm like an internal campaign process right now. And the other thing that I would offer is it's never just one conversation. My almost 10 years of being a founder now, I have tried to communicate things as efficiently as possible. Forget it. I accept until I say the same message 7 times publicly to someone. Publicly is important because in a public environment, people can then be like, yeah, he said the thing. He said the thing. And then, oh yeah, I remember he said the thing 7 times. I am then now confident that it's stuck and there's clarity, and then people are ready to move forward and align with you on the plan.

This is, I think, the second podcast that I'm actually going to go in and listen back. Aaron at Hush was the other one.

That's— I appreciate it. That's big.

We're, we're 75 episodes in.

Yeah.

Number 2.

Everything you— the, especially the last couple minutes, I was like, I need to write that down. I'm like trying to drill it into my head.

Alex, you've been on a crazy journey over the last decade. Looking back at it, what would you say is the biggest turning pro moment you've had in your career?

Turning, turning pro, turning pro moment. The biggest one for me was accepting that my ego shouldn't drive my entrepreneurial endeavors. Because when I left finance, as I mentioned earlier, ego was through the roof. I'm like 20-something in New York City doing the New York nightlife. You know, all the, all this, all the silly stupid things that just inflate your ego. And then when it came to startups, my first iteration of it was building an incubator, a studio where I had a bunch of little companies running around, you know, begging me for my time, needing my resources, you know, coming and asking me for advice. And like, here I am, you know, in the corner office and like, okay, great. Like, I'll now, I'll see you now. Right. Like, completely structurally dumb, like was not a financially successful outcome either, but I built it around my ego. It just made me feel good. Like I had left this high-flying finance job and now here I am still feeling like I'm important. It was only until I checked that ego and did some real work to say, hey, you gotta be purpose-driven. You need to find mission. And conviction around things that are greater than just you. Yes, financial outcomes are important. Yes, achievement is important, but that purpose, that Simon Sinek start with why, right? Really going back, reading that book and saying, what is it for you? Aligning on that and then realizing what I really love doing is helping other businesses be successful because I struggled to do it myself in a big way. And if I can make other people more successful through my knowledge, through my relationships, and now through my technology, that's my purpose. That gets me super excited to get out of bed and do all sorts of crazy things into the late, late hours of the night. And that would be, if I were to look back in my big turning pro moment, that was what I would look at as a huge change in my trajectory and my ability to be successful and also recruit really talented people to align with that ultimately exponentially augment whatever it is you're trying to achieve.

Oh, mic drop.

Yeah, this was great. Can you talk to the camera on your left? Tell them where they can find you and Proxima.

Sure thing. So feel free to reach me on LinkedIn, Alex Song. On Twitter, @1alexjsong1. And Proxima.ai is my full-time business. Feel free to shoot me an email. I'm just alex@proxima.ai. Looking forward to hearing from you.

Hell yeah. Thanks for coming on, man. That's a wrap.

Thank you guys. That was fun. I really appreciate it.

That was good, man.

That was good time, man.