Nate Bosshard: Algorithmic Immunity

Nate Bosshard is a visionary brand builder and entrepreneur who’s helped shape iconic companies like Burton, Tonal, and hims & hers through a rare blend of taste, intuition, and strategic insight.

Join us as we explore Nate’s perspective on what makes a brand truly resonate, from crafting emotional worlds to resisting the pull of algorithmic influence. He shares hard-earned lessons on launching category-defining products, building brands that move culture, & why taste might just be your most valuable asset.

Transcript

Intro: [00:00:00] From Silicon Valley, the heart of startup land, it's Getting2Alpha. The show about creating innovative, compelling experiences that people love. And now, here's your host, game designer, entrepreneur, and startup coach, Amy Jo Kim.

Amy: Nate Bosshard is an investor and entrepreneur who's known for building iconic brands at the intersection of design, culture, and technology. From Burton Snowboards to Tonal to Brand AI, he's helped shape powerful narratives that fuse emotional resonance with functional innovation.

Lately Nate's been exploring what he calls algorithmic immunity, a call to reclaim our personal taste and identity in an age dominated by AI driven feeds and homogenized digital experiences.

Nate: When you ask someone about your company or brand, they can describe it back to you in the way that hoped and wished [00:01:00] they would. That is the act of branding.

If you're too early, you're wrong. Timing is as important as literally anything else.

With ai, you can develop product faster, more efficiently, quicker, lower cost, but you still run up against the gravity of traditional go to market. And that is not being innovated by ai, unfortunately.

Amy: Join me as we dive into Nate's thoughts on branding self-expression, and why now, more than ever, we need to actively curate the influences that shape who we are. 

Welcome Nate to the Getting to Alpha podcast. 

Nate: Happy to be here. 

Amy: I'm very happy to talk to you. So you and I reconnected a few weeks ago when you wrote a post on algorithmic immunity and it really sparked my imagination and we talked about it, dove into it a bit. So I wanna start off by recapping that idea and having you explain to us what you mean by algorithmic immunity and how this concept [00:02:00] bubbled up for you in your life.

Nate: Sure. Well, I pride myself on having a diverse set of interests, pursuits, tastes both kind of professionally and personally. And they've been pretty consistent my whole life actually. And a lot of my journey was people being like, what I was into is weird. But I feel like I've been redeemed recently in a lot of different ways.

And I started to realize just through my friend group, my kind of outer network, my kids, that people stick with things less and less. And a lot of that is around the time and effort and work is required to develop your taste. And what I mean by taste is like pretty broad. I don't mean like taste like what you like to buy, like that's just one very small slice of it.

But taste around what drives you, what interests you, where you like to go, who you like to hang out with, what you like to read. I really like the things that kind of create your i your identity both inward and outward. And I started to realize that a lot of [00:03:00] that was being eroded by the way that people were consuming media.

And what I mean by that is that when you go from leaning in research,

Nate: that's a way to develop your taste versus, the way the algorithm likes to do it is just like all recommendation based, never ending scroll, never ending feed led by your lizard brain in a lot of ways, which sometimes isn't really what you want or think you should be spending your time on.

I think it starts to erode into degrade, a person's ability to identify what drives them, what interests they have, and so on and so forth. And so it was just this, I just coined that phrase as a overarching concept that I think some people found, it strike a chord and I think it's something that when you're aware of you start to think about it and try to establish ways to defend yourself from that.

Does that answer your question? 

Amy: Totally, yeah. We'll be digging more into that and some ideas adjacent to that shortly. So. You're really talking about, you're really talking about [00:04:00] taste, and part of why I invited you into this conversation and why I'm so fascinated with your point of view is you're a branding guy who works in tech and that's very different than myself who came up through engineering and design and really product.

You've got this extraordinary history working with and developing brands, which I really wanna dive into. But first of all, can you make the connections between taste and brand, like you've got this idea, we all develop our taste. It's really being shaped in some possibly not great ways by the algorithm.

How does that connect to what a brand is and how you, as a super experienced brand manager would go, would think about that? 

Nate: Yeah, I mean, I think the best brands. Evoke an ideal that is usually, in, in a well executed way, quietly [00:05:00] emotive. And I think when a brand presents, like a worldview, an experience, an idealized state, that creates a lot of emotional connection and those are the best brands.

Whether it's design, whether it's activity, whether it's fitness, whether it's fun, whether it is status, I think, the best brands create this world and they offer you a doorway into that. And then that ends up becoming, a part of your identity in some way, shape or form. Not for like sense nine toothpaste.

That's I'll call that like a very functional brand, but great product if you're. If your gums are eroding. But you know, like the North Face or a Burton Snowboards where I used to work or maybe in luxury brands, right? With which evoke an ideal as well. And they, they create like emotional permission for you to associate yourself with that.

And then I think through that, a lot of discovery can occur as well. And then you start to pull on threads and learn things about yourself. 

Amy: How do you do that? How do you take something which never starts off that way, presumably and create a world around that? You've [00:06:00] probably done that several times.

Nate: Yeah, I mean, I've had the great fortune of working with brands that are very easy to tell stories around. So, my first job, that I ever had was at Burton Snowboards, and that was actually like, I. The only thing I cared about from the time I was in high school to the time I graduated from college to the day that I started working there, is I wanted to do everything I could possibly do to get a job there, because all I cared about was snowboarding.

The ideal, the lifestyle around it, the experience of it, the kind of camaraderie that you get from it, being in the outdoors, feeling in a flow state, all those sort of things. And so tie that in with what is like a, at that time, like a pretty subversive, counterculture, irreverent community. It wasn't mainstream.

You had a lot of different things you could build around. And it was super fun. And so I think that concept was very helpful for me as I continued on with my career because I had you know what I would say, like the most, like [00:07:00] fertile, soil to, to grow and learn from, around true kind of fundamentals of community brand building culture.

Health fitness, wellness com, all those things. And then every brand wants to have some version of that, some thread of that, can they have them all at once? Very hard.

Amy: Okay. So, and I'll say 

Nate: one more thing. Yeah. And I think like the best brands can articulate, I'm being very simplistic, obviously, like there's a lot of nuance, everything I'm saying, but just for general broad strokes, like the best brands have a, an emotional benefit to the consumer and a functional benefit to the consumer.

And they both serve different purposes in how and when a person wants to associate themselves with you. And there's times and places for each of those. And the best brands can pulley, lever, ebb and flow, depending on the medium. The time of year, the format, the platform the channel, all those sort of things.

But you're always like using those two levers to tell the right story at the right time. 

Amy: Wow. Can you give me an example that's really [00:08:00] fascinating? 

Nate: Using like the Burton example or just in general? Sure. A I mean, I it's like very easy. Let's just take like a $700 Goretex jacket.

Okay. Functionally it's going to keep you very dry and very warm emotionally. You look sick wearing it, you look cool, you feel good, and you also know it's going to perform. So like that would be like a very like basic example. And you get, you can take that through to automotive, you can take that through to luxury.

There's always some functional aspect most of the time to the thing that's like high price point. And so that's what I mean, it's like feature benefit. What's the emotional benefit? What's the functional benefit? How do I weave those stories together? 

Amy: Right. And it's contextualized with creating a world.

Nate: Yeah. I think you always want to begin that, to use like a marketing, example, if you're doing like a seasonal kind of marketing plan, you want to start from the customer. Who are they? What do they care about? What's happening in their life? What's happening in the macro, what's happening in the [00:09:00] micro, who, who do they associate with?

Who do they look up to? Who do they care about? And then you work backwards from that. I think like you always have to start with audience and language also, before you go into visual development, for example. And then you've got obviously like business goals, product goals, new things. You wanna launch initiatives and you have to then wrap it around, that customer in a lot of ways.

And so it's as much like tactical as it is psychological

Amy: right. 

Nate: Yeah. 

Amy: What techniques do you use or have you used to shape and test language with the customer? 

Nate: In the early part of my career let's just call it like the, there's three chapters in my career. There's like the kind of action sports outdoor period of my career.

Then there's like the working inside tech companies. And then there's my current role in investing in incubating companies. In the first half of my career, it was all just gut. Like you didn't deserve to have the job you had unless you had essentially like a like a medium, like style pipeline to the customer.

I buy medium like a [00:10:00] fortune teller. Like you have to know the customer, right? And so you've done whatever it takes internally to build that trust. And people just used to just believe what you felt was true. Very little customer research in those days. Like you just had a gut instinct and usually it was correct.

I think as my career evolved and especially in the advent of like channel and paid marketing and essentially like social media, paid marketing, SEO you have, you had a much more

Nate: of a pallet to test things. There. There was, back in the day, like the channels you had, you shipped them and that you better hope they were good 'cause you didn't have the opportunity to like ab test or iterate unless it was like your own website.

And so then that evolved obviously, but a lot of times then in like phase two, you still would be operating under your, on your gut, but then you would do research to validate that. That was like the other methodology as I matured and, started working in different, what I call like technology focused organizations.

Amy: Right. So let's weave these threads together [00:11:00] and talk about tonal from your lens as this longtime brand expert. And this is in phase two or maybe three of your career. 

Nate: Yeah, it was like the back half of phase two. I guess I would, how would describe 

Amy: that? 

Nate: So 

Amy: how did that first get sparked? What were you seeing in the world?

What were you experiencing that made you, I mean, it's a lot to found and get a company started. Well, I didn't invent the 

Nate: technology just to be explicitly clear. That was like Ali Orti. And I met Ali when I was working at Khosla Ventures, so I did do a pit stop between

Nate: helping start tonal. And then my Operation Pro, I did two years at Khosla Ventures between my time at Nest and Tonal. And I had a whatever reputation around being someone that could like translate consumer storytelling to technology products.

And Ali, I met he was pitching, like essentially a pre-seed investment. He had a very rudimentary prototype [00:12:00] built. And I just really appreciated his story. Like he actually has maybe the best founding story that I've ever heard complete, authenticity where he was overweight and he was an engineer and he had some, had some moderate success.

And he realized that the only way that he could transform his body and like. Reclaim it was through strength training. And then he went on this long journey, had that light bulb moment that can I turn gravity into electricity? And then, that was how it began.

And then I continued to work with him and help him as a coline. I ultimately he convinced me to join him. And at that Oh, so 

Amy: So he pulled you out of Csla? 

Nate: Yeah. 

Amy: Oh yeah. Yeah. That's interesting. 

Nate: Yeah. I was really excited about that opportunity because I felt like it was category defining, like he had invented a piece of essentially science fiction, like a true innovation, like patented one of one discovery around this type of methodology where you could essentially like use electricity and then compress everything in a weight room to this small little form factor that you mount on your [00:13:00] wall.

There just was this secular trend around health and wellness that I felt was just barely getting started. And you have to remember, like Peloton, it was still pretty early. Like they hadn't, they weren't like pre predestined, in 2015 or whenever that was.

And so it was really like the honor of my career to be able to take, all these technology and actually create a brand from scratch like that. I think for any marketer, like you have, like your primary mode is shepherding a brand, right? And protecting it, the brand pre-exists. But being able to create something from scratch, like from the name to how it looks, to how you talk about it, to how it visually is presented, like that's I think like the honor of any marketer's career and it's a very rare opportunity.

And so that was like very exciting to me. 

Amy: Was that the first brand from Scratch opportunity you had? 

Nate: I had launched sub-brands

Nate: inside, like Burton Snowboards in the North face. But nothing like de novo now. That was like a really fun experience. 

Amy: Okay.

So how did you talk about the [00:14:00] functionality and then the emotions with tonal? And also did that change? Did you start thinking about it a certain way and then learn that it was actually something else? Or were your initial instincts just right on how did that out? I mean, there was 

Nate: really like two or three core benefits, and I have to like, go back to my notes, but let's start with the consumer.

We isolated it down to three consumer types. People who wanted external who are motivated externally. So how I look in a bathing suit. Being complimented on how fit I look, that there was people who were internally motivated. So I want to just beat my next metric. I don't care about like other people telling me how I'm doing.

I'm really like looking at my metrics and can I make myself like 1% better every day? So like the internal motivators. And there was this third group that was like, I need motivation. And the product had, benefits for each of those types of people. And ultimately, like what are the biggest points of [00:15:00] friction to staying fit is the convenience aspect.

A being able to go somewhere and get your workout in. With regards to strength training, I think cardio is really easy 'cause everybody knows how to run. But to strength train properly, it requires form and technique and programming and sequencing of exercises. And then the types of, sets you're doing and the volume and then how you're doing over time and what you should be eating.

It's like very high cognitive load. So our kind of core benefit was, it's convenient, it's got the entire gym on your wall. It takes a cognitive load out of strength training, which is highly intimidating for people. It basically tells you what to do and exactly how much weight to lift.

And then ultimately, like the externally motivating results is like if you follow a along, like you're gonna look better and then you're gonna feel better. And I think we've seen that, especially in the last 10 years. There's I don't, I mean, incredible price elasticity around people's willingness to invest in their health and fitness and wellness.

And so that was like the other, that was like the other trend. I think that was part of that, that, 'cause the product [00:16:00] was very considered, purchased quite, quite a high price point, and it was a completely new form factor. It was like science fiction, it was like an invention. So there's a lot of like product marketing work to be done there.

It's not an impulse of purchase, that people needed to touch it. So, there's a lot of like ramp up there. 

Amy: How did the pandemic impact that business? 

Nate: I left right at the beginning of the pandemic, but I think every pandemic business they had a sugar high that then if you didn't manage properly came with some downside challenges.

And I don't wanna get too much into it, but a lot of businesses I think face that, where they like ramped up really quickly and then that kind of pandemic bubble burst and interest rates changed. There was obviously like that economic period, in 20 22, 20 23 that like, I think brought a lot of people down to earth.

And so, I will say I still believe, and I think the data proves that it is one of the best consumer electronics products we have launched in the last 10 years. It's got some of the best retention [00:17:00] of any product. On the market. And if you talk to any person who has it, like they're effusively in love with that product.

But you know, consumer hardware is really hard. It requires a lot of capital, especially at that price point. And so, is a non-trivial business to run. And a lot of the scaling of that company, I was not there for that. I was there in the zero to 1.5 period. But that pandemic kind of scale period.

I, I wasn't at the company at that point, so I can't kinda officially speak to it. 

Amy: But your point about the pandemic dynamics and the cheap interest rates and the sugar high, I immediately think of five businesses in my circle, of course, who have that same effect. And so you describe it, Nate, I know you've been told this before, but you really have a way with words like there's a lot of.

Clarity and specificity in the way you use language, which I think really reflects branding and marketing and just how much of that is weaving a world with [00:18:00] language? 

Nate: Yeah, I mean, I think the best marketers are also students of history and students of people, and that's where I think, having a really wide aperture is helpful.

Like where you have a lot of experiences, you have a lot of interests. You've tried a lot of things. You have like weird histories in your life that you maybe you're embarrassed to admit you did, but like that builds, I think that builds like a pretty high level of consumer empathy and awareness, both culturally and functionally.

I think the best marketers like view a lot of that. Yeah. And I've had the luxury of working across a pretty like wide spectrum of consumer brands. So I've touched a couple different, rails across a consumer's kind of journey. 

Amy: So a lot of people in my audience are very technical founders, people working in tech who aren't necessarily familiar with branding.

Yeah. So if you're gonna give the straightforward, what is branding from your point of view and why is it important? 

Nate: Brand is how [00:19:00] people 

describe you. If you have done a good job, when you ask someone about your company or brand, they can describe it back to you in the way that you want, you hoped and wished they would.

That is the act of branding. Yeah. In my opinion. And so, you have to essentially let the bird fly outta the nest and you just like hope that you've fed it properly. Then when the world interacts with it, they see and have internalized the same things that you've attempted to communicate.

Amy: In my world, I think of that as a clear mental model. 'cause that springs out of a clear mental model tonal peloton for weightlifting done. Right. It's, I understand it. Yeah. That was part of what's so brilliant about that product. That was, we

Nate: We were a little like resistant to make that analogy, but that was the Oh, really?

Well, because I think we felt like our product was way more technical than Right Peloton and way more nuanced and had way more kind of features and benefits. But that's a great example of [00:20:00] we couldn't control that. They were ahead of us. They were scaling much faster than us at the time, and so you had to just accept that, but you had to do your best to create really clear differences.

But I. That was the simplest analogy that we couldn't control. So there's also macro factors, that sometimes are outta your control, like that one that you just used. But yeah. 

Amy: Right. Well that's actually why one of the techniques I use a lot is to come up with language and then run it by your exact target audience and see what they think, like before you launch a product or a whole campaign.

Nate: Totally. And that's like in, segmentation studies, especially if you don't have the luxury of launching in public and iterating quickly you do need to do that for sure. 

Amy: So tell us about brand ai, which is pretty exciting. 

Nate: Sure. Let's see here. So the brand, like a. I'm talking like again in [00:21:00] very broad strokes, so, you can pick apart my generalizations, but a brand leader in an organization, sits in my opinion at, in the center of the wheel in a lot of ways because everybody cares about branding.

The executive team, the product team, the sales team, customer service, everybody within marketing channel partners, engineering. That is the genesa quo. That is the DNA that permeates throughout the entire organization. And it's in theory the least commoditized thing if you do it right, it's like the last thing to be commoditized in a business.

And yet it is historically been a very qualitative very services based practice. And there's been virtually no software I. Because usually the branding process is, a brand team working with an internal external creative partner, maybe some ex internal external research resources.

And then you've got, all these different seasonal product initiatives and you try to pull that in, [00:22:00] identify, what your business goals are, and then you basically need to create like an expression of that out to the customer that hits on all those goals. And hopefully it, it drives the narrative forward.

And that has been a very manual services based process. And so, as someone who's, worked with agencies, hired agencies, worked with internal creative agencies, there's a lot to love about that process. And then there's a lot of opportunity to improve it. And when Chat, GPT-3 came out, so I guess that was like fall of 22, loosely right around that period, like end of 22, early 23.

I was playing with it, and I had this pretty clear epiphany. I'm like, well, this is the worst it's going to ever be, and holy shit, this is gonna completely transform marketing. And I had this premise that like, wow, like brand marketing now actually has software. And so I worked, we essentially incubated that in partnership with [00:23:00] another founder who is a longtime friend and creative collaborative of mine outside of our fund.

And we work on that internally and then essentially spun it out. And what brand AI ultimately is attempting to be is, an operating system that your brand can live within. Usually your brand sits in like a two dimensional PDF. It's not interactive, it's not responsive, it's not deployable.

It's not interoperable. You not 

Amy: What's a PF? 

Nate: Like a PDF document. Oh, pdf DF Yeah, like a brand standards document with like copy and design guidelines. I got it. It's just like a very static thing. And then the brand manager, spends like half their job, like socializing that brand through the organiz, and I'm talking about like large scale organizations.

There's different use cases for this product, but imagine a large scaled organization who is global and has touchpoints everywhere and has a lot of brand risk if things go out that are wrong. And the brand manager spends a, like half their job socializing the brand with people who touch it and then policing it.

And we felt like there, and then there's obviously the whole like agency development process, [00:24:00] which, I always felt could be improved, could be, could be, could have more efficiency in and around that. And so yeah, we built this product. We preceded it through our fund and had a, have a full-time team working on it.

We went out and raised external capital last year, about $6 million. And we have a bunch of, fortune 500 companies using it right now. And it's super exciting. And, I just felt like this was a great opportunity. Timing, really important here to give brand marketers, a product that they've never had.

Essentially give them like a Jarvis suit, to use like a Marvel comics analogy. Improve efficiency, reduce brand risk, create better connectivity throughout the organization to let other people interact with the brand. And so that's like high level what the product is. 

Amy: You posted an amazing story along with a screenshot from brand AI about a Nike campaign.

Nate: Yeah. 

Amy: Which that was a little, 

Nate: that, that was a little an, that was a little [00:25:00] antagonistic. But the point remains that culture moves faster than we can manage today. The amount of brand touchpoints that a brand used to have, which was like print tv out home, maybe some direct mail now has exploded into a hundred different touchpoints that are m moving a million miles an hour.

And if you were a very large scaled brand, you have a lot of people using it. And so the more people you have using and interacting and deploying with your brand, there's more brand risk. And what's crazy is that you can decimate brand value instantly today in the era of social media. And so one of the core products we built was essentially like a brand compliance tool that allows, anybody in an organization to check their work against, to make sure that whatever they're putting out there might not have some like thing they hadn't thought about. Or maybe in a different country, people would find that offensive.

Or maybe there's something [00:26:00] happening like right now today that would imply that you're being insensitive by putting this creative out. And so it's essentially an insurance tool that's one part of what the product does. It's, it is what a brand manager used to do where you would create your seasonal bank of assets, you would hand them off to everybody in the organization, and then those team members would come back to you and ask for creative approval on the asset and that, and then that brand used to live inside of you.

And now we've taken that and we've put that into this dynamic piece of software that anybody can check work against. And it sounds very simplistic, but we're taking so much data. Both internal documentation and then tons of external, what I'll call just like listening devices across culture, across all these different channels, and then making sure that, we're triangulating and giving you the best feedback on the risk of your product.

Amy: So listening devices, basically scraping the data, 

Nate: Like scraping the data like in the world. I'm not gonna reveal how we do it, but Right. We are [00:27:00] pulling from a lot of really important places that are ha, that are like instant in real time. And then creating weights against what your brain's trying to communicate and then put that decision back into the hands of the marketer or the channel partner that's trying to put this creative out and just surfacing to them any potential risk or brand damage that could occur if they were to put this creative out.

So when you imagine you're like a, a brand like Nike, like you've got brand managers in every country. You're doing national, state level campaigns, regional campaigns, global campaigns. There's a lot of people touching your assets and putting them out there. I mean, you saw what happened at Bud Light, a couple years ago.

I mean, that's a great example of a regional social media manager creating like $10 billion and just destroying $10 billion of brand value. I guarantee you that nobody in the like central marketing team saw that creative, right. And that's like the canonical example.

But literally every week there's someone stepping on a rake to use like a Bugs Bunny analogy, right? That's a great analogy. Or Elmer Fudd, I can't [00:28:00] remember. Whoever, whoever steps on that rake. I think it's more Elmer Fudd. But anyway. 

Amy: Who does step on that rake? 

Well, we will figure it out and put a meme into, I mean, stepping on 

Nate: a rake, slipping on a banana peel, 

Amy: but yeah, it's same 

Nate: analogy. 

Amy: Yeah. And it's really fascinating to look at this through your eyes, through a brand expert and you just flow with it. It's like you live and breathe it. 

Nate: Well, yeah, I mean, we, the team, all three of us came from this background and have a lot of nuance.

Nuance and a lot of history. Like amongst the founding team, we'd worked inside large brands, we'd worked inside agencies, we'd deployed huge amounts of budget. Like we were building a product for ourselves, essentially. And that's, I think, ultimately like the best product you could build is if you're building something for yourself.

Right. And hopefully what you're building for yourself has a lot of crossover appeal to other people, in your peer group. Right. But that was the core origin of it. Yeah. 

Amy: So how long have you been running brand ai? Now I'm 

Nate: not the [00:29:00] CEO. I'm a full-time, working inside offline ventures, which is, we're on fund two.

Fund one was a hundred million dollars fund two's $110 million. We've got great LPs and endowments that have given us their capital. And all of our partners are

Nate: former entrepreneurs in some way, shape or form. And we are, exclusively focused on early stage investing and we wanted to have our cake needed two.

And so our capital structure is that 20% of our time, investible capital we can allocate towards starting companies. 

Amy: So like a venture studio model?

Yeah. Sort of like a venture studio inside the fund? 

Nate: Correct. 

Amy: Okay. Got it. 

Nate: Yeah, that's how I would describe it. There's some nuances with how we do things.

But that. Originated out of that model. Yeah. You are such 

Amy: an entrepreneur, you just can't not 

Nate: Yeah. I think I consider myself a creative person and

Nate: I think when you have an idea that you don't pursue that's always should I [00:30:00] 

Hunter: should have 

Nate: probably done something with that, so it's like, how do you like reduce your re your kind of creative regret? It's a complete luxury and like I pinch myself every day that I get to do what I do. But yeah, I mean that, that process was like, I had an idea, it was very early and unstructured. I reached out to a very close friend of mine who I really trusted and knew to be, more creative and more product than me. And we just spent like months just like jamming on this idea, fucking around with product. And he took that and ran with it. And obviously I'm one of the co-founders and work with him on it. But he's all, all in, right. Eight hours, 80 hours a week on it.

And, he's probably the best person that I could ask for working on it. And now we're closing like contracts, which is like really exciting that like our thesis is proving to be true.

Amy: Love it. Well there's definitely, but here's the 

Nate: thing with ai, like you can develop product faster, more efficiently, quicker, lower cost, but you still run up against the gravity of [00:31:00] traditional go to market.

And that is not being innovated by I ai, unfortunately. And so, getting people to consider something still is the old fashioned way. 

Amy: Right. So there's so many things you're bringing up and I know folks are gonna have questions as well. I have just a few more. Sure. You're pulling on a thread in several of these stories, which I think is it's not a recipe, but it's a heuristic in that, you like with brand AI and also with Burton, the book ending these stories.

Yeah. Both of those, you are really going into something where you have pretty deep domain expertise, knowledge and passion. It's and that as an investor, I imagine you probably look for that as well. Ollie's another good example, right? So sometimes I work with people and they wanna do something, but they just don't have domain expertise.

Right. And so how do you, I get, it's not a [00:32:00] rule, right? So I do make an exception, but how do you think about, I feel like there's a thread there that's Well, you're bringing up about entrepreneurship. 

Nate: Yeah. I mean, you're bringing up like the missionary versus mercenary type of entrepreneur. Sure. And I think both can be successful.

You can have this mercenary entrepreneur who sees a business model, whole, and they just they are driven by like dissecting and attacking that thing. And maybe they don't even care emotionally about the thing they're working on. And that's okay. You can be either one of those people.

I personally like can't I just as a human, like I have to care about something. Like I'm pretty idealistic in that way. And so, I'm drawn to more missionary entrepreneurs, but I've worked with mercenary entrepreneurs who've done really good. And there's no right or wrong way to that.

But from a personal

Nate: product development standpoint, like I've been teaching myself to code. 'cause all these these new AI coding tools are just like completely insane. Where now you can actually build your idea like very quickly. [00:33:00] Yep. And I've been working on something that's like very personal to me and I probably would only be working on something like that, that I care, I'm building a product for myself, which is inherently emotional and personal and more of a missionary approach.

But

Nate: I have no bias against mercenary entrepreneurs and I'm like, will happily invest in them. It just depends on what it is and 

Amy: Right. But if you're in an area that requires deep expertise and you don't have it, 

Nate: well, I think you can have technical expertise. And you can be smart enough to seek the domain expertise to augment your technical skill.

I think you can have founding teams that are a blend of all three of those characteristics, frankly. Right. Well, 

Amy: those are the ideal ones, right? Yeah, 

Nate: exactly. 

Amy: Yeah. Ex, so you were an advisor to HIMS and hers. 

Nate: Yeah. 

Amy: That's a really interesting company. 

Nate: It is very interesting. And Andrew is an absolute force of nature.

Amy: That's what it looks like. So what, how, what drew you to that and like what, how did that emerge into the [00:34:00] explosive growth they're having now? It also is amazingly branded, so 

Nate: Yeah. I mean that's, I can't, you've got a great 

Amy: lens. 

Nate: I can't take a ton of credit for the growth that we've seen and all that.

That's all Andrew. But I met Andrew when I was at Khosla Ventures. He had a company that he had started that was like a Dropbox competitor that didn't. Didn't work. And he reached out to me. This is like before the company really was founded and we were just like riffing on consumer.

And he had done a few tests. He had a product premise and in, in the, in that company, there was three things happening. Obviously timing is always the most important thing, but you had a bunch of like very profitable, like aesthetic drugs going off of patent.

So a lot of hair loss drugs, retile dysfunction, drugs going off patent. You had

Nate: a millennial customer who was open to be marketed to the way that I would say women have been marketed to for decades, but more, a more kind of emotionally aware customer. You had regulatory telehealth laws being loosened [00:35:00] and then you had, a lot of, digital channels that had not been fully saturated like they are now. So you had this perfect storm of consumer willingness to be marketed to and communicated to in a certain way. You had a regulatory framework that was being loosened. You had a product framework that was being loosened and you had a channel opportunity, and then you put that in the hands of someone like Andrew, who's just an absolute, 0.1%, entrepreneur.

And I really helped, in that pre-launch days, like putting the brands together, like the early kind of DNA of the brand, like helping him think through that. And so that's what I worked on, was building the brand with him in that very first pre-launch. How did 

Amy: you come to Hims and hers?

Nate: The name or just what? 

Amy: The name and the positioning. 

Nate: Cause it's really, 

Amy: again, it's strong, 

Nate: but it's again, it's functional and it's emotional. It's get these, like men up until that point probably were insecure talking about [00:36:00] self-care, insecure about losing their hair or whatever, sexual challenges they were having.

There was this openness. And then you had the like, convenience and efficiency of a telehealth service. And then, there's a lot of lifestyle opportunities in those products. 'cause they are very aesthetic products. Obviously the company's expanded so far beyond that at this point, but in the very early days.

And so the goal was again, it's have a really clear, precise, functional message, a really price clear emotional message. And then try to wrap it in like a brand essence that's memorable and simple and pithy and like I. Ownable. And I would argue that the HIMMS and hers brand really defined that like premium, mediocre, millennial, direct to consumer aesthetic that a million people copied.

I 

Amy: fucking love it. And to add to it and just bring it around to what you said earlier, all of that's embedded in these multiple inflections that were happening in the broader culture and regulatory environment. Timing that [00:37:00] piece is so 

Nate: important. I mean, you can have a, not the best team nail timing and win.

So timing, if you're too early, you're wrong. Right? So, timing is as important as literally anything else. And I, I think of culture as like this river moving really quickly and like the best entrepreneurs are able to I. Salmon, they're a bear. They like grab the salmon, out of it.

And like then they wrap up pro they, they create a product expression around that, right? And understanding what's happening in the world. And I, identifying a consumer paint or consumer opportunity and then wrapping that in a product, that's the magic of entrepreneurship.

At least consumer entrepreneurship. 

Amy: Love it. So you now are running fund two. You obviously talk to a lot of entrepreneurs. You're an entrepreneur yourself. You've been on so many different sides of these equations. What are some of the mistakes that you see entrepreneurs making, maybe around branding, maybe around something else [00:38:00] that you wish they wouldn't, but everybody has to learn?

What are some of those mistakes you just see over and over again that perhaps we could avoid? 

I. 

Nate: I mean, it's very category dependent. It's very technology dependent. I can't give you like a universal answer to that, but what I will say is that if you care about how you present yourself and your company like that goes a long way.

If you visually and verbally present yourself in a polished way, especially if you're like an early stage entrepreneur, you can smooth out a lot of the things that aren't working because at least you're, it looks like you really care about the craft of how you're presenting yourself.

And so you can't hide behind a bad product. Right. Obviously. But I am always just drawn to and entrepreneurs, I really care about people being a student of history and not to not like them being dogmatic like about it, but more like. I've researched this space, I come from this space. I've here's all the things about why this hasn't worked [00:39:00] in the past or past companies that try to do this and why it didn't work and why the timing was wrong or the product was wrong.

Like all of that shows that you're a real student of what you're working on. And I'm very drawn to that. 'cause in the early stage, seed, pre-seed investing, like very rarely do you have a functioning live product. Sometimes you do. And so storytelling is like as important as what you've built today.

And then, communicating it to me in a way where I can pitch it back to you, like really easily. 

Amy: Yes. Coming full circle 

Nate: back to the branding, back to the branding concept. 

Amy: Right. 

Nate: But again, like everything I'm saying like loosely and can argue against what I said depending on what the thing is.

Amy: That makes sense. That's how I know you're an expert. 

Nate: Yeah. 

Amy: Right. But it sounds like a lot of it is a certain kind of awareness. Awareness of how you're presenting yourself, awareness of the dynamics going on in the world. Just having that awareness is sort of table stakes. 

Nate: Yeah. And then you've got a [00:40:00] really clear product expression that you're gonna wrap that insight around.

Amy: I have one last thing and I'm, this is a little provocative, but I'm hoping I get a really insightful answer. And I gotta say, Nate, I just thank you so much for sharing your point of view. It's incredibly illuminating for me and I think for everybody, but for me in particular, 

Nate: I appreciate that 

Amy: it just.

It's adjacent to and expands my own worldview. Right. So I've been struggling. I'm gonna be just upfront, I'm not a brand expert, but I'm a product designer and, care a lot about launching products in the world. I'm struggling to understand your description of brand io and I'm not the target audience, right?

Yeah. But you, but I wanna see if I can understand it better. So you say, well, it's a brand os and so do you mean by that we've built a platform and then there's these apps that run on [00:41:00] the platform? Is that what you mean by an os? Because brand os I have trouble just as a human understanding. Oh well. Who should I recommend that to or what is this?

Nate: Sure. I mean, I'll maybe be more specific. 

Amy: Yes, 

Nate: thank you. Brand sits at the center of most organizations and everybody needs to interact with the brand today. The way that people within an organization interact with the brand is usually through the bottleneck of the marketing team and it usually sits in like a 2D non-interactive document.

We've taken everything about your brand today, historically, future product marketing, business insights. We've put that into a simple interface that allows the brand team to easily interact with their brand, permission it out, permission it to other people in the department, 88 with it, build on it, build materials around it, and build compliance tools around it.

That allows your brand to be way more responsive to the world around it and way more reactive to the internal needs of your team.

Amy: Got it. So calling it an OS is arbitrary. 

Nate: It is, [00:42:00] but I mean, it is an operating system in a way because it. Connects to other parts of your internal software as well. 

Amy: So are brand managers your ICP ?

Nate: Brand team. So brand directors, CMOs

Nate: marketing program managers. There's a whole suite of people, but the way we articulate the pain points, which I haven't really, I'm not pitching to you like I would be pitching it to a marketing person are pretty clear and well understood and I think there's challenges of introducing a new piece of software, but then there's also opportunities 'cause you're hopefully defining the category to a certain degree.

Amy: So brand teams and people that work with them, 

Nate: which is the entire organization . 

Amy: It's a really exciting premise. And your example from the Nike ad was just, it made it crystal clear. Now I understand that's a small slice of the functionality. 

Nate: Totally. But that is, I would say that is the most acute red hot core a that a lot [00:43:00] of scaled brands feel.

And it's what keeps a lot of CMOs up at night because they worry that their brand is going to do something wrong, that destroys value. Right. And especially when touchpoints and channels and culture are moving so fast, it's like very hard to stay on top of that. And the only thing that can do that really is ai, right?

Which is, one of the most miraculous tools to find pattern from noise, par through large data, and then come and surface something that's like really precise to you, I think is, that's like the opportunity as well. 

Amy: Don't step on the rake. 

Nate: Don't slip on the rig, don't slip on the banana peel.

Amy: Right. All right. Thank you so much for dropping gems on us. Of course. This was so much fun. I hope you had a good time as well. 

Nate: Yeah, that's great. 

Outro: Thanks for listening to Getting2Alpha with Amy Jo Kim, the shows that help you innovate faster and smarter. Be sure to check out our website, getting2alpha.com. That's getting[number]2alpha.com for more great resources [00:44:00] and podcast episodes.