#21: Alexi Robichaux, BetterUp

Welcome to From Startup to Grownup, the podcast. My name is Alisa Cohn. I'm an executive coach, an angel investor, and the author of From Startup to Grownup. Each week I talk to founders, creators, advisors, investors, and builders of all kinds about their insights and experiences in going from startup to grownup. This is episode number 21, and I'm completely excited to welcome Alexi Robichaud to the show. Alexei is the co-founder and CEO of BetterUp, which is a platform that provides coaching of all kinds to the employees of companies like Google, SAP, WarnerMedia, Bain, companies like that. Alexei and I talk about so many things. We talk about the early days when he had to deal with what he calls a cacophony of pain and misery and what a visit to a group of Navy SEALs taught him about how to run his company. We talk about his hard-won lessons about how to manage people. Why it took him 2 years to hire a CRO, the frameworks he's used to scale the business, and the mentors he's had to help him learn them. Now, I just wanna mention that BetterUp is a platform that provides coaching. Alexi is himself very into coaching, and I am of course a coach. So we do talk about coaching, but mostly we talk about it in the context of building the business and building his skills as a leader. In any case, This is a wonderful episode, super value-packed, so you're gonna wanna take notes. Please enjoy my incredible conversation with Alexi Robichaud. Alexi, welcome to the show. I'm so happy to have you.

I'm delighted and honored to be here. Thanks so much, Alisa Cohn, for having me.

I'm so excited to talk to you. You know, I love the founding story of BetterUp, so I'd love you to start there and to share with us kind of the founding story, how you came up with the idea of BetterUp and how you turned it into a company.

Sure, um, thanks for the opportunity to share. Well, uh, the story I guess comes out of myself and my amazing co-founder Eddie's personal experience. Um, we through a set of events found ourselves as young professionals coaching and mentoring high school students after school, and I had actually helped start that organization when I was in high school. Some buddies had recruited me into that, and that ignited in me this passion for helping people even at a very young age build really meaningful Productive Lives, uh, and Eddie had come across the organization through his sister, his little sister actually, going through the program in high school serendipitously. And Eddie and I had been acquaintances and, and friends at USC and reconnected around that. And so we were both young professionals. He was in management consulting, I was at a startup that got acquired by a large tech company, going through that integration. But nights and weekends we were coaching these high school students. And in my own personal experience, I pretty quickly went from helping to run product at a small startup to being an executive at a Fortune 500 company, um, integrating multiple units, being one of the heads of product there. And I would say in retrospect, like, significantly in some areas underskilled to the role, but, you know, was kind of on this, like, I was probably 25, 26, like this hotshot young executive track, and all tied in on flying business class, meeting the world's greatest CIOs and CTOs, and I essentially burnt myself out. You know, I was unhappy with the way things were going at work. I blamed the environment. I blamed the, you know, the integration, the lack of strategy. And when I, you know, I think finally got some coaching uninvitedly through a friend who did a really caring intervention, I realized like, this is really about me and I'm not being who I am and who I value. I'm not doing what I care about, which is helping these kids after school. And I've gotten all wrapped up in these kind of like inauthentic hopes and dreams around being a hotshot executive, which was like never— I wanted to be like a constitutional lawyer as a kid, was never even like something in my head. I have just absorbed that from the environment. And meanwhile, Eddie was going through his own journey of being overwhelmed and being stressed out in some of these, you know, management consulting, then private equity. And, and so it really centered around this realization that like we needed help, I needed help, and I'd I spend my time with Eddie after school and weekends doing these summer camps for inner city youth in the Bay Area as well. And I kept coming to this idea of like, they have a better support structure than Eddie and I. They have Eddie and I, which for them, you know, is great. You're 16, 17 trying to apply for your first job and someone who is a management consultant, private equity person coaching you on your resume and interview, life-changing. And who was us for us? And that was the start of BetterUp. And I authentically didn't have an answer. I just didn't know. Who I was supposed to go talk to. And so that started a journey of about 9 months of me trying to find help. And that took me through therapy, coaching, life coaching, executive coaching, Landmark Forum, the Camino de Santiago in Spain, and reading a ton of positive psych, you know, Adam Grant, Angela Duckworth, kind of workplace enlightened positive organizational behavior. And I was just, I guess the word was like frustrated as I discovered that actually science knew so much of this for 30 years, but I had never been told so many of these things. And there were people out there like you who knew this and helped people do this, and I didn't know they existed. And that was the seed of BetterUp, of like, how do we find people and get them in the palms of young— we thought it would be for young professionals like Eddie or I, young professionals worldwide to help on everything from managing our psychology to our mental fitness, to yes, leadership and tactical job skills as well. And so Eddie and I got really high conviction around, we can kind of supercharge what we're doing for these high schoolers honor this integration of this is both self-actualization, this is also leadership development, and it is also mental fitness all in one fell swoop, and really create what we, we still believe and we're building is the first real brand focused on helping adults self-actualize and realize their full potential for that entire journey of their adult development. And so fast forward 9 years, we're still not bankrupt and we're doing it.

Amazing.

Fingers crossed.

Fingers crossed. You're after one foot in front of the other. I love it. Wait, I had never heard that story. I have to ask you, I'd never heard the you had gotten a loving intervention from a friend, like that you were being burned out. You were sort of also taken away by the trappings of this success. Tell me about that intervention. Who was it?

It was my friend Michelle, who's a therapist by training, but she had joined the startup before me to pay her way through her therapy grad school as the EA of the CEO. And she stayed on the ride through the integration. She's now, I mean, she actually went to become one of the first BetterUp coaches and really was the prototype of BetterUp coaches in many ways. How do we not just take executive coaches from the business world, but how do we take clinicians who have a different skillset and make them relevant to the business world because so much of what underpins our leadership performance is actually our own wellbeing. And so we'll probably get to that later. But she really just one day like pulled me aside and was just very gently and sweetly in her way, like, "You don't seem like you've been yourself lately," and just really checked in. And I don't know why it just hit me like a ton of bricks. And she was right. I had hypervigilance. I took tests and I tested positive for PTSD and I had never been to combat. I had night sweats, night terrors, hypervigilance. Loud noises would upset me, like telltale signs. And I just kind of blamed everyone but myself and just was like, they're all the problem. You know, when they change their lives and they start doing their job right, then I will be okay. And I don't know why. Maybe it was just the, the, the, the, the sincerity and genuineness with which she did it.. But it really recentered. Now I have the language. It put the locus control back on me, the agency of like, am I okay? And I realized really fundamentally I was miserable. I was not okay. I was upset. I was resentful. I was not doing well. I was not flourishing to use, you know, Seligman's work. Using Corey Key's work, I was clearly languishing. I didn't have a, like a true clinical diagnosis. I don't think I actually had PTSD. But I certainly was not thriving. And, uh, I realized that it's not about changing my environment. That's what I thought. It's actually I need to change me. Like, I, I— there's a lot of problems, but I am the biggest problem that I can solve. And that kind of started me on the journey of how do I go do that.

Yeah. Oh my God. Well, we're definitely going to get there in terms of locus of control and the journey of a startup founder and how much, you know, on the one hand you were burned out when you're working for someone else, but now you've taken on the hardest job there is, really. But I want to actually ask you about a story that you told me when I was interviewing for my book, um, From Startup to Grownup. You told me about you and your co-founder Eddie Medina going to visit Navy SEALs and what you found out. Basically, the question is, why didn't you quit? I love that. Can you tell us that story about seeing the Navy SEALs and what you— what insight you had?

Yeah, so we started working on kind of the stuff of BetterUp early. You're kind of like, you have the general point of view and vision, you know. We knew there'd be a human expert, a coach, or a therapist involved. We're still figuring all that out. And we were talking to one gentleman who John Seely Brown, who was an early advisor, believed in us when almost no one else did. Investor. He had run Xerox PARC back in the day, Amazon board member at the time. And he was like, you know, he said it as like an offhanded comment. He's like, you know who you should really talk to is like the US Navy SEALs. He's like, I, I, you know, they, they, they have some of the best sports psychology. So much of what you're saying is actually sports psychology applied to, you know, like traditional white-collar knowledge work, right? And so he's like, it just occurs to me you should maybe go talk to some elite performers and understand their psychology and how sustainably do that? I was like, okay. And then Eddie and I thought of a buddy who went to USC with us, who Eddie's childhood best friend happened to become his wife, who also went to USC with us. And so he was an officer in the Navy SEALs, Larson Jensen. We called Larson up and he's like, he totally got it. He's also a two-time Olympic medalist, so he's like a superhuman. And so he's like, yeah, like, let's come down here. I can pull some of the guys together. They all happen to be guys at that point in time, and we'll do a focus group like they'll spend the day with you. You just got to go to Costco and buy like a ton of liquor. Like, I'm just telling you, that's probably your payment. Like, do we need to pay them for their time? He's like, no, no, no, we'll do it at my house. Make it fun. Like, just bring a bunch of good snacks and something to drink. They'll be good to go. Right. So we go to Costco, we do that. We go to Coronado down in San Diego. And yeah, you know, you're looking at these guys and they're not like— they're not who you archetypically would think would be a Navy SEAL. They're not all the biggest. I mean, they're all in great shape, right? But they're not like The Rock. You know, and so they're much leaner, maybe a little more lean muscle, very athletic build. And so we're going around and I don't know how it came up. At one point we just asked like, hey, BUD/S is one of the hardest things a human can do. It's notorious for that. Why did you make it? We're trying to get to their psychology and someone else didn't. And, you know, it was weird because the question puzzled and confounded them. Like we almost saw a deer in a headlight stare from many of them. It was like, what do you mean? And it was like, no, like This is really hard to do. Like, I forgot what it is, like 1% make it through. It's very low matriculation. Why did you make it through? Why are we here? And you started with a bunch of guys who aren't here. Why? And to a man, it was like, because we chose to be here. And it was like, what? And I mean, Eddie and I still talk about, I mean, we're talking about it now. We still talk about this day. It was like, okay, unpack that. What do you mean you chose to be here? Now remember back to me, little weakling Alexi, I'm not choosing anything. My culture's chosen for me. My aspirations were chosen for me, right? Like, my frustrations have been foisted on me, right? And so you see this other side of this powerful— we chose not— and it's like, break it down. And essentially it goes like this: you have two choices when you go into BUD/S. You can ring the bell, or you can be willing to die in the water. And you're just like, whoa. And essentially they all had a story, very personal. My dad was a SEAL. I looked him in the eyes and said, like, I'm not ringing the bell or I'm not coming home. Or the guy who mentored me, you know, whatever it may be, someone in their life where it was like, we're choosing, we've made this choice and it is a choice, right, for us to do that. And if that means I got sick, one of them had gotten sick, I have to redo it. I redo it till I do it right. And so Eddie and I left that and we're like, of course, these are life and death consequences, right? Startups are not like— your startup may die, but they are not truly life or death consequences. But what Eddie and I took away from that is like, You know, failure is a choice in many ways. Sometimes things happen to us, but if we stop, that's failure. If we just keep doing this— we called ourselves the cockroaches of Silicon Valley— then we can never fail, right? And so our choice is to— we choose to fail by agreeing to stop. And we just committed that we were never going to fail because we would never stop. And that, in retrospect, was probably a dumb decision. There were so many cases where we should have stopped Yeah, but at this point, whatever, it's working out for us. And so we're happy about it. But to be fair, we never after that point had a conversation about quitting. And there are so many times I'm like, we really should have. But it's just like we put that out of our brain, what we learned from them, we put it out of our brain and it's just like a door closed and we never— it never revisited, which opened up so many other doors of things we could solve or things we could do. Even when everything seemed against us, we could still not ring the bell. We could still go do this or that.

Right. And just to clarify, when you ring the bell, they come and get you and they give you hot coffee and take you out of the water and they put a warm towel around you and you're done and comfortable, but you don't get to be a Navy SEAL.

And they taunt you, right? From my understanding, I've never done this, but they'll taunt you, right? It's like, do you want to ring the bell? This is, right? And so it's really interesting because you have to, by design, it's a really powerful principle. They don't quit, they don't pull you out of the water and say you're done. No, no, no, no. They'll leave you and they'll let you and your boat crew will help you. Not, you know, but like, they make you choose to quit. It's not that you're eliminated, it's that you eliminate yourself, which is like— you think about it, you think it's like you're pulled out, you're disqualified. No, no, no, you actually choose to quit. By default, you're there, is my understanding. And so I think it's obviously— it's, it's extreme, extreme ownership. We're talking about the US Navy SEALs, right? Not applicable to so many areas of our life. They're in their own league and they're doing things most of us fortunately never have to brave. But what is applicable to our life is this idea of we have a choicefulness in everything we do. And that's where our humanity lives in honoring that choicefulness.

Yeah, I love it. And, you know, you just said, and I wanted to explore with you, you had so many times that you should have given up. Could you share a few times where you should have given up and what that, what that was like, what specific examples were, and then what the thought process was in the sense you didn't give up?

Yeah, and I mean, I guess now we can say, well, we shouldn't have given up, right? Because things are, you know, we're still here. But yeah, it would have objectively seemed that we should have given up. I mean, I think early on, like, we were, you know, we had this big audacious vision and this pretty, I would say at the time, precocious point of view, is that like, hey, there's a bunch of false dichotomies in the world related to mental health, illness versus creating healthfulness. That's a false dichotomy. You know, leadership versus wellbeing or false dichotomy, right? And there's a reason these all exist. But actually what we want is people— what I wanted, what Eddie wanted, what people who use BetterUp world over now want— they want that integrated experience where they're really optimized. And this was 2013. You can imagine, like, people were still wrapping their head around meditation for the most part. And so we're on the scene and it was a rough first 2 years. I mean, I think one of the early experiences was like, we just— I failed just horribly at funding the company, which is one of your most important jobs as a CEO. Um, I think, you know, we got rejected 76 times in our seed round.

76 times?

Yeah, between like angels and institutions. Um, and it was like 18 months. I mean, it, it, it was brutal. And like, you know, some would have said that's feedback from investors that you don't have a business. Like, there's nothing here. And I think that would have been a really rational place to walk away, and no one would have blamed us. It's not like you've got— you know, I coach entrepreneurs now, it's crushing even your first rejection. Ah, it's like, no, no, no, give it like another 75 goes, then we can talk about it, right? And there's some founders who have that number in hundreds, right, by the way. So, um, I think that would have been a first jumping-off point where people would have said, job well done, you gave it your all. That's a rational, reasonable number above which you should probably, you know, take that as a good sample. Size and take the feedback from the universe. But I think for Eddie and I, we were just— I don't know if we have compromised risk-reward centers or what. We were just like, hey, like, they're not right. Like, the reasons they're telling us are wrong. It's not that we just insist we're right. It's that their reasons are wrong. They actually don't understand what we're saying, which maybe means we're communicating it wrong. But like, they're actually wrong. And it's hard. Eddie and I are not like big ego in that way. Like, we don't— everyone hurt. Everyone, we're like, wow, are they right? We were probably down for 2 or 3 days, like, they're right, they're so right. And then we go back there, we're like, no, you know what, they're kind of right. There is something they said that is right. These are smart people. They're not objectively wrong, but they are wrong about the thesis being wrong. Like, yeah, that business model isn't going to scale, or yeah, that's going to be really tough. So that's right. And that may be enough for them to want to pass, but that's not enough for us to go pass. We're not passing over that because like we still think there's enough correctness in this point of view. We'll figure it out. So I, I mean, I can, I have 9 years of them, but I would say that was probably a pretty seminal, we could have or should have walked away moment.

I can imagine. What about some others later in the game, sort of like 3 years in or 5 years in?

Yeah. So I think they get less frequent in some ways, right? Like you get more steam and momentum behind the business and it's a little bit more like, you know, I think we early on, we, we, so we, we start as direct-to-consumer, prosumer. I mean, it was college students and, uh, employees. Became clear that didn't work, you know, and I think that could have been another point. This is probably 2 to 3 years in, and then I'll get to 5 years where it was like, hey, you don't have a business. Like, people are using your product, they're hiding in their car at lunch to go do it. You know, Ryan, our CTO, joined in the condition we would never sell to enterprises. We had been in enterprise software together. We were like, they won't honor the data privacy, they'll be trying to spy on their people. And so that was one where we were pretty crushed. We're like, that's our business. And it took a lot of us thinking from first principles and unwrapping, like, why do you think that will happen in the enterprise? If you could prove to yourself they wouldn't do that, wouldn't it be better? They'd be being paid for, they'd be sanctioned at work, they wouldn't be hiding in their cars. Yeah. Um, but that was a point where that was a big business model change. Uh, it would have been very rational to be like, let's go find the next consumer version of this and see what consumers will pay for at a lower price point. Maybe we'll put some audio clips on an app that's free or something like that. You know, like, we had a lot of ideas. There were a lot of ideas starting to crop up around then, but we really said like, no, I think instead of like quitting, I think what we need to do is really go eat some crow here, have a nice bowl of crow, swallow our pride. Yeah, think from first principles and follow the water over the rocks where people are using the product. And so that was one. Then I think fast forward, you know, this isn't like quitting quitting, but it would be failure to us, you know, once we started to get steam, we had a lot of opportunities to be acquired. I mean, you know, big companies need innovative teams, and so you get, you get the emails from people's corporate dev, you get the notes from CEOs. And, you know, for us, we just never even entertained the conversation. Just like, we're not here for that, we're here to partner. Like, we've decided, and from day one, BetterUp is going to be an independent company or it's not going to exist. That's always been the case. And if we were just trying to make a buck, then, you know, we could have made a buck. And it's, it's scary because at some point you get to this valuation price where those options aren't options anymore. You're too expensive. And now it's like, if you— we were never holding on, so it didn't matter to us. Again, compromise risk-reward center, entrepreneur's greatest gift. Um, so we, we were just like, doesn't matter to us. But like, for investors, and our investors were like, that can be a scary moment because it's like, I don't have that salvage value anymore. I'm not getting a 5x return, I'm getting a 500x return or zero return. And I think for Eddie and I, it was like, what? That's always what the game we were playing, and our early investors and All of our investors, we've ensured they're aligned to that. But that's a classic moment to walk away in a way and walk away with a win.

The classic moment when you could M&A, you were saying, get acquired. And yeah, and you just had decided, no, we're not doing that. That's not what we're in this for.

It was one of the first conversations Eddie and I had.

Yeah.

I mean, I had been through a not— not— I mean, the acquirer was very gracious, but it wasn't a great integration of the strategy. And I just— it's not why we built BetterUp. I mean, and I respect entrepreneurs, by the way. I don't say that moralistically or normatively. Like, I think what's important is you and your co-founder are clear about this and you're on the same page. There you can start a company to make money. This is capitalism. That's a valid reason to start a company. You can start a company because you want to control something forever. That's also kind of a weird reason, but a valid reason to start a company. For us, we wanted to, to use the Steve Jobs quote, make a dent in the world and prove to ourselves that that can be done and then do something beautiful with that. And we made really darn sure that we both believe that in our heart of hearts. And it helps you. It's almost like a horse with blinders. It just makes you go faster cuz you don't have to entertain all that other junk.

Mm. That's right. It kind of gives you this north star, this point of focus. Yeah. Yeah. That's great. You know, you, you keep talking about 9 years and I know that you've been around for 9 years and you've been the CEO for 9 years. And you also just talked about the fact that you're, you know, your first job as CEO was to, you know, fund the company. And that took a little while to get there. I'm just curious, how did you view your role as CEO and the kind of the first year or two?

Yeah, I mean, I think I had been around startups long— like, I, I knew there was a multi-stage to CEO, and I think, you know, I— Eddie did too in, in his role. And, um, so I, I, I— but I'll— so I don't think we were surprised by the change, right? I think, you know, growing into that change is a whole different story. But yeah, look, in the early days, um, everyone in the team, which was Eddie and I, the entire team, everyone in the team, and then Ryan, who was moonlighting before we could afford to pay him um, your job is to build. You're a maker first, right? And that job, in a very simple way, you go from maker to manager over time, right? Like, that would be the most simplistic evolution of that. Um, and so early on, your job is to find product-market fit, build something people want, uh, and create something that's going to set up a company for enduring, you know, differentiation, moats, all these things. So you're wearing an architect hat, you're wearing an engineer hat, you're wearing this coach hat, you're wearing a plethora of hats, but they're really focused on And in my mental model, they're really focused on like, can I find a really, really, really big vein of gold that we can mine for 100 years? You know, and you can find other veins along the way, by the way, but the bigger you find that first vein, the better you set this company up for success. And a big key part of that as an early-stage startup at any stage is financing that, right? So you have to have that vision. You have to have that point of view. I would say even before the vision, you need a unique point of view of the world. The vision ladders into that. Then you need to— you need the right people. That's, that's usually more important. You're not paying people. So do you have the right people? Then it's like, yeah, do you have the oxygen? Do you have the time? You're really buying time, not money. Money is just a heuristic to get time. What you actually need is time. You need time to go mine, time to go really like, is that where the vein is? How big is it? How rich is it? Let's start chipping away at it. The way you do that in our economy is you compensate people for their time, which means you then need money. But I think it is important. Really what you need is time. And so that's the, that's the early job. Now, those dimensions honestly don't change as you get bigger. They just become more scaled, harder, and you delegate and empower more to help you. And there's some new ones that get added. But early on, you know, I was the product manager, like I was building product all day, talking to users, doing support tickets with Eddie, like drawing interfaces, like doing whatever it took to bring this product vision to life.

So, I mean, I get that. That's— and I love how you sort of say that that is almost a similar job then as you grow and now 9 years later. But describe the differences and the nuances. Then I also want to double-click on what it's like to empower people because when you're doing everything yourself, you know what's going on. When you have to empower and delegate, you no longer know what's going on. And definitely things are going wrong. So that's really hard too. But start with maybe telling us what— how you see the job today, especially the nuances that you have that are different.

Yeah, I think just picking up, I mean, what's constant, although the directness of it changes, to your point, is learning. Your real job at all these stages, in my opinion, is to learn. You're trying to create a learning machine and a learning culture. It's easy when there's 2 or 3 people. You don't need— there's not like a new work stream to learn, right? It's just like learning happens metabolically. You're 3 people. Ryan was never co-located with us, so 3 people remotely working together. You're learning, learning, learning. That's still actually your job. You read The Fifth Discipline, Peter Senge, Peter Drucker, any of the— I guess they're all named Peter, but whatever. You read any of these folks, that's still the job, right? When you're a massive company, it's just harder to do because there's more people involved and the challenges are so much bigger than any one person can do. And so at that scale, how the job changes is it becomes about building these systems and practices that still help you learn faster than competition, faster than a market if you want to be an innovator and stay at the forefront of your user, learning what they need, learning how you can help them, helping them sometimes. We are big adherents of Blue Ocean. You're actually helping your non-customer understand that they could even use it, right? So you're learning, you're helping them learn. You're like meta-learning, right? And so, okay, that's a lot of people become involved. So it goes from like, you don't need to manage to do that. You do it yourself to now you are not directly— I mean, I like to still talk to customers, but you become more indirect and your job becomes to architect and set and systematize and put those wheels in place and really make sure you have the right resources, the right teams, the right roles, responsibilities to do that. And so it becomes, you know, less of you being the player in the field and more you on the coach on the sideline to eventually you the owner of the franchise to eventually like you maybe you're running the NFL, right? To use that analogy.

How have you personally handled that? Like what? I guess I'm so curious, like How have you personally grown to be that person who can then be the, you know, the owner of the franchise or the, you know, the, the, the whole, the CEO of the whole thing as compared to the doer or the manager of just 5 people?

Yeah. I mean, I think, um, I mean, time will tell is the honest answer, right? I'm, I'm still here. We'll see what's best for the company in the next 40, 50 years. Right. But, um, it is true as a founder, you're the rate limiter of your company's growth. Through your own personal growth. And for me, the mechanisms of doing that has been kind of viewing myself as clichély as it is, is like a little plant. And like, does my little plant have the, have the right stuff? And what do little plants need? Well, I need some soil, I need some water, I need some butt kicking, AKA husbandry and trimming, pruning now and then, and crafting an ecosystem to do that. You can't do that alone. And I think if Eddie and I did anything well, because we got kicked in the teeth so much at the beginning, it created like a fever pitch of desperation. We were always convinced we were doing everything wrong because everything— everyone was telling us we were doing everything wrong and we didn't want to give up. But we didn't maybe have the— I don't know. I don't think it's hubris, but we didn't have that confidence that like, no, we're right, this is the right way. And so that resulted in us trying to learn from people. And so early on, we were— we probably had like— I remember being criticized for how many advisors we had early on. People are like, that's like a negative correlation. When I see stars with a ton of advisors, I see founders who like are just talkers and blah, you know, whatever, bad VC heuristics. Um, but that's really helped us. That's been this like watering, pruning through all these years. I mean, I, I'm talking to an advisor or a board member or an investor more than one a day on average.

Still, even now.

On average. Yeah. I mean, that's who just called me, one of our board members, not about anything, just to, just to chat and check in. We were texting about something earlier, like, and. That's part of the job as a CEO. Like, that is— Eddie doesn't have to do that as much. He still does it, but like, I do that most as CEO. Um, I would not be able to grow the business if I wasn't learning from people who have been at the stage ahead of us or have coached people the stage ahead of us. It's, it's in that sense, it's kind of not rocket science. It's like, people are like, how do you grow with it? It's like, you dig in roots, you dump water every day, you make sure you get sunshine and you prune. And It's not about you. It's actually about are you creating the system around you to give you that feedback, that accountability, that butt kicking if you need it, but also to help you look ahead and to help validate you. And so for me, it's been about these systems, advisors, scientific advisors separately from corporate advisors because we care so much about the science. Board members make sure they have enough context on the business to actually keep you accountable. Embrace that. Don't be scared of that, right? Other investors writ large. Who are subject matter experts in domains you care about, whether those your domain or not, where you can pull their knowledge, right? Coaches. I, I recently dropped down to 2. I for years had 3 coaches. It got just too much to manage with 3. But at a personal level, are you doing that? Are you hiring people that you respect as experts that you want to learn from them? And like when you Tetris all that together, it feels like it's hard not to learn. Because you're just constantly— no, honestly, like you're just constantly being shown that like you're incomplete and that's an okay start, but that's not going to get you there. And it's, it's, I don't know, I think it's super fun. It's, it's super fun and it's inspiring and allows you to hopefully go within and inspire your team more and elevate their thinking.

You know what I appreciate about the way you just— and I want to talk about specifically some of your advisors and your coaches, but like, I appreciate the way you just articulated that. It's like the love of the game. Like you have to love learning. Because otherwise you're just not going to embrace the learning and therefore you're not going to grow. But like, you're like, I love the learning. It's fun to learn.

I mean, I've always loved learning and I love this Leonardo da Vinci quote, like, learning never exhausts the mind. Um, I think that, that to me is why I got into startups because they're these limitless platforms for human learning. And I mean, obviously this is kind of meta with our company, like, but you discover this huge part of yourself and you realize your full potential. So For me, this whole thing is an adventure. And like all adventures, there's some dark valleys you have to go through and there's some high mountains you have to climb. But like, if you don't love the thrill of the adventure, beware, right? Because like, this is not for the faint at heart. This is for people who really are cool confronting their greatest demons, their greatest weaknesses, and wanting to climb that mountain.

So tell me about— I'm going to ask you about maybe an example with one of your coaches and with one of your advisors or board members. So specifically, a kind of conversation or a little bit of the conversation you've had recently with an advisor or a board member where you learned something and then similarly with one of the coaches that you work with.

Yeah. Okay. I mean, I'm learning things all the time. So, here's one, you know, we're, we're going through this journey right now where we're, we're growing the business. We started with an initial product. It was a platform, but it's still like one SKU or, you know, one sales item. And we now have multiple products. They are, you know, they're on platform, they interlay, really 1 1 3, really powerful. That's a totally different commercial motion and sales motion. And look, the majority, just as a background why this is so important, the majority of our business is still threaded through a direct sales model, mainly to large enterprise. And so one thing we've been talking about as a board is like, you know, Do we have the right team in place to do that? And I think we do because we hired with that, right? But there were some hard conversations as I started to envision and see together with Eddie, this was the future to deliver on that point of view. There was some, you know, I think real feedback on, hey, I'm not sure these are— this person can operate in that world. And it's like, man, but I really like that person, right? Like that person really loves the values. They really love the mission. And, you know, and so that's what good boards will do. They'll keep you accountable. But it's like, hey, you have a blink here. Like, that's not aligned. You're saying you want to go here. This person's never gone there. They've never worked in a business that operates that way. You— oh, by the way, you haven't, which is fine because you're like driving this thing, but that means even more they need to be. And so, you know, I think that, that's, you know, we have a great team. We've, I think, really honored that feedback and incorporated over the past 18 months and who we've hired and who we built. But those are, you know, they're tough conversations where you, you can just dismiss it and be like, you're wrong, you're not here every day, you only check in blah, blah, blah. Or you can really say, you know what, you have this beautiful critical distance. You don't know how or care why the sausage is made. You just care if it tastes good. And I actually love that because like, you shouldn't have to care. Our customers don't care how or why or when the sausage is made. They just care that it tastes good. And so like, I'm going to honor your objectivity here and be like, huh, I don't have to go do exactly what you say. That's not what you even want. But I have to take the spirit of what you're saying and internalize that and ask myself, are they right? And if they're right, then like my duty as a CEO, my duty to the mission, certainly my fiduciary duty, but first and foremost to the mission, is to make sure I'm setting this mission up for success. And so, you know, I've had to go the other way where, you know, we had— funny, we are one of the few companies I know in Silicon Valley history to have a negative sales quarter. Don't— it's a— it's an amazing— you first get a zero and then you get a D book. That's how you do it. So painful. I mean, we were doing tens of millions of dollars in ARR when this happened. We have been switching out our sales teams, switching out marketing. Zero quarter, I was doing a new search for CRO. That search ended up taking 2 years. And for sure there were board members. Yeah, yeah, literally. Like, I mean, that is not exaggeration. I mean, multiple search firms. I had a reputation. No search firm wanted to work with me. I was the CEO who could never hire a CRO. And, you know, the board was actually quite split on it. We had some board members who were like, you just need to get the next resume that looks competent. And like, they weren't quite like, and hire this. Like, this is a you problem. You're being a picky pants, you're a little gun-shy after, you know, the last go-around. You need to like lean in here, learn from your mistakes, and hire someone. And I had a couple directors who— well, really just one— who were like, no, you need to stick to your guns. Like, you need— this is a high-quality bar. You want a certain type of enlightened sales leader who's going to be the brand incarnate, walk into that room and manifest it. And that's not every enterprise sales sales leader. Right? You have a very particular brand. You're not selling a database, right? No slight to anyone. It's different if you're selling a database than what we're selling. And, um, that was hard. Like, who do you listen to, you know? And, um, in my case, I, I, I held out, and I held— and it took 2 years. And we have the best sales leader in the world for what we're doing right now. And I think— I know they would all say, glad you did that, right? Glad you— glad you held out.

I have to stop you because you've got a bunch of people— you've got your own self-doubt because of course it's like very strange to take 2 years that you don't I hear about that. You've got recruiters not returning your calls, and you've got directors, your board directors, saying, "Hey, man, you got to be kidding me." So then you have one director saying, "Stick with your guns," and you have an internal compass, which is like, "We need the right person." I just want to know what that's like internally because that is very— that is like people say, "Oh, you got to make tough choices," but that's actually a very tough choice. What was that like for you?

Oh, it's terrible. I mean, you just feel like a loser. Like, people— by the way, like, your sales team hates you. I mean, who— they're like, this is a knucklehead CEO who's never led a sales team who's now internally leading this. Like, we know better than him. They probably did. But, you know, it's like, it— there's that whole internal angle of employees are unhappy, right? Employees in sales are like, we want a leader who knows what they're doing. Uh, employees outside of sales are like, It really sucks that we're doing our jobs well and then we have things like zero quarters, even though the product I just shipped is awesome because of— because Alexi can't go hire a head of sales, you know. So it's generally a cacophony of misery and self-doubt. Uh, and so it's, it's not a fun place to be, but, you know, it's kind of like a pain tolerance question of you have to do the perspective thinking of what will be worse. Like, and at some point actually in that 2 years, I did hire someone and ended up to not be a good fit. Very brief stint. And, you know, I, in retrospect, like, I shouldn't have made that hire. You know, I kind of— they weren't quite right. I knew it, but I, you know, wanted to believe it due to the pressure. And I recovered from that mistake very quickly. And there's some learning and self-awareness there. But it was super, super tough. You know, I mean, my, my wife was probably my greatest coach at that point because it's like you're venting, commiserating, whining, crying, everything, you know. As Ben Horowitz would say, you sleep like a baby, then you wake up every 2 hours and cry. So yeah, I mean, to answer your question, it's not fun. You just have to say, like, you know what's worse? Having the wrong head of sales and having to do this all again. And so like, that is actually worse.

Totally. That is a great story and a great example. Do you have an example of maybe a conversation you had with one of your coaches and what you got out of that specifically?

I thought I was being super empathetic to some of my direct reports, and I was getting really frustrated because I felt like they were taking advantage of my generosity. And like, I was giving them extra time to complete assignments. I was like being very explicit, putting things in writing. And, you know, generally I was just like, hey, I'm not seeing like the reliability, the follow-through, and it feels like they just kind of know that like I'm maybe not going to fire them. This is me talking to my coach, right? And the reason is because I think their heart's in the right place. I think they have the right raw materials. But yeah, they're not performing to the job to be done right now. And at the time, I didn't even have the sophistication of the job to be done framework, right? So I was just kind of like resentful, bitter about it. And the conversation and I think the feedback from the coach was a couple of things were happening there. A lot of things were happening. One, you know, I thought I was being empathetic, but actually I think the big reframe was, well, you're not being empathetic because you're managing these people the way you want to be managed, not the way they want to be managed. And empathy is understanding the other. And so like, have you really had a conversation with them about, here's what I need, like, what's an effective way for us to partner around that? Or you just say, hey, uh, newsflash, Alexi, you're an entrepreneur, you like very little management. Right? And you think by giving people that you're being generous and you're respecting their autonomy, but some of these folks may literally need you to check in once a week. It may be helpful for them. And you don't need to do that in like a micromanaging way. You need to like check in and ask and have a conversation. You can reflect, this is not working for me as your manager and as a business. The job to be done is not getting done. Um, so how can we constructively partner? What would work for you? I'm serving you as your leader. What would— but we're both serving the mission of this company. And as CEO, I am the arbitrator of performance of this company. So what, what would help serve you serving the mission and serving this business? And, you know, I really was in a mindset that like I was being taken advantage of, like my empathy was being taken advantage of. And what I realized is, no, actually, this is a surprise. This is a failure on your part of— you're actually not being empathetic. You're, you're doing what you would want. And we have the golden rule: do unto others as you would do. Actually, it's kind of like You know, the spirit of that is right, but it's like how you apply it. You have to go understand the other and ask what works for them. And I hadn't done that discovery, to use a sales term. I hadn't had that conversation. I was kind of doing an Alexi-sized approach to management fits all.

Well, and so then you were able to have the conversations with those people.

Yeah. And it still didn't change it in most of the cases. So it didn't end up working out long term, but at least I was not frustrated and I was not resentful. Because then it was like, hey, I've asked you what works for you, right? Right. I've now done what works for you and it's still not working. It's truly not me, right? Because in my head I'm always trying to control the variables. Is this just me? Like, am I just managing this person poorly, to be fair to them, right? And you have— I think you have to ask that to have the honesty and the high ground when you have these performance— if it's just like you're not performing and I've never considered I may be contributing to that, that's really messed up.

And also then you have the clarity. Once you have that conversation with them, then it's like, "We also have an agreement, an explicit agreement." That's right. And that's so helpful because then it's like, "Oh, now it's not happening, but we already had a number of conversations where you made an explicit agreement, so now you can move on," as opposed to, "Oh, maybe it's me. I'm not sure." Yeah.

And it depersonalizes it because now it's very matter of fact. It's out in the open. And you're rooting for this person, which is the whole premise here. And why I felt so betrayed would be the word.

Hurt.

I felt betrayed because I'm like, I'm betting on you, and if I was just judging your performance, I wouldn't be betting on you. I'm actually betting on you despite you not performing, yet I'm getting like none, no, you know, no reciprocity on that good faith. That was the failure. And I think that's often overlooked, is like a lot of managers feel that way, right? And that was the second lesson. The second learning was, you know, that's about you, Alexi. Like, you feel betrayed because you aren't setting a boundary of performance. You're going beyond what actually you should be doing or tolerating. And then you do feel taken advantage of. And the way to solve that is you stop letting yourself get taken advantage of. You need to say, hey, there's a boundary at which, like, if the skill mismatch becomes so high, I will coach you once or twice. But then at some point I can't because then I can't take care of the other people on the team. Then I'm really actually suboptimizing myself as a CEO and I'm being a bad fiduciary of this company because I can't be propping you up. It robs you of the opportunity. It robs me of doing the rest of my job, which is thinking about the future, whatever else I may be doing. And the emotional clarity, though, is then you don't feel taken advantage of, right? Because you're like, actually, I— to use Adam Grant's work— I gave, but I was a bounded giver. I gave in a metered way. I didn't limitlessly give. You found the most successful people were not takers, they were givers who gave within boundaries. And so that was the lesson in the lesson there was this becomes so frustrating and mostly frothy for you, Alexi, because you feel betrayed. And that's a very basic emotion, but that's actually not them. They aren't trying to betray you. That's you betraying your own principles and boundaries.

I think it's so common to have to learn that kind of the hard way. And for yourself as a manager, as a growing manager, as a growing leader, have you then turned around and And have you seen that over and over in your managers who you've had to coach? Here's what I learned. Oh yeah. Here's how you need to think about it. Like, has that been— how has that played out then with coaching others?

I mean, it's a big part of my job. I spent 2 hours this morning with an onboarding class of all new executives at BetterUp, right? So Eddie and I still do this. We do manager training. We bring in other folks, great folks who, you know, actually know what they're talking about. But no, like we, we're really committed to this.

This.

I think it's one of the most important things you can do, is you're, you're, you're the chief anthropologist of your company as CEO. You set that culture, you set those behaviors. And even if you're not perfect, the intentionality you signal to people that I am taking this seriously, I'm invested in my growth, and I'm invested in your growth, signals that like, I expect you to be invested in your growth. And so, um, we're certainly not perfect at it, but yes, you almost can tell any new layer of management, there's like 4 or 5 of these common—

not—

I don't want to call them tropes because they're really raw for these folks that they suffer with. Ruinous empathy, these things we just talked around, not setting, not trusting or verifying or doing one out of proportion with the other, right? So absolutely, we— and because we're growing so fast, we're, you know, more than doubling our employee population every year. We always have a crop of hundreds at this point of new managers because we do like to promote from within. And so— it's a constant. It's not just me, I wouldn't scale, but it's a constant investment. And it is often coaching on, you know, this is a coach, everything's different, but there's often like 5 to 7 patterns that are like the Pareto principle, get 80% of the value.

Oh, totally true. Yeah, actually, I talk about that in my book, From Start-Up to Grown-Up, the notion of like, here's what you do as a manager, right? Give feedback and coaching, have the difficult conversations, learn to delegate, right? Delegate is a whole thing. It's not just abdicate. It's right. It's, it's a trust. And to your point about the distinction between trusting and clarifying and having accountability systems and, and applying your delegation to that person as opposed to, well, you should be able to do that, or not giving a senior task to a junior person, right? And, and then to your point, really how to manage people so they feel managed but not, um, don't be so overbearing.

Yeah, I mean, Liz Wiseman talks about this in Multipliers, right? It's like this balance you want to, you know, you can diminish, like, you, most of us accidentally diminish our team in some way, and it's not vindictive, it's not bad, it's— we're trying to help them, right? And by trying to help them, we, we actually remove the locus of control from them. We give them a pass through toleration that it's okay that you can't do this, uh, and we rob them of growth opportunities as a result. And really good high performers want the opposite of that. I want the opposite of that, right? Like, most people want the opposite of that. And but we, we do it from the best of intentions, in quotes. And so So we are constantly perfecting our own craft there, but trying to cascade and replay and share those mistakes for the next generation of leaders at BetterUp to hopefully not repeat.

Totally. And then let's go back to this notion of executives because the other— not want to say the other side of the coin, but an adjacent topic is you've got these great leaders, senior leaders, executives in the company, and they're fantastic and they were with you since the beginning or early days. And then the truth is that through no fault of them, like they're just not oriented to scale fast enough to where you need to be. Or they can scale all day long. What you need is someone who's done it for 20 years. And so, then you have to have the conversation with them that it's not going to work anymore. How do you think about that? What's an example of a difficult conversation you had to have? Yeah.

Well, first, maybe on the how I think about it, if I can. I got some coaching. I probably shouldn't say who, but this is one of the most iconic founder CEOs of enterprise company. And, um, you know, two frameworks he shared with me early in our journey which have been really helpful here is, you know, I was asking him what made his company so successful as he's had the benefit of reflecting on that. And he, he, he pointed to this point about upgrading the leadership team. He pretty much found a pretty direct correlation between the, um, speed at which they did that or the frequency at which they did that and the growth of the business. And he's noticed when companies are more reticent to do that, they stagnate growth. And the goal is not to be like, great, who do we go change today? That's just like scary, right? But really honoring, like, is this the right team to get to the next level? And usually when you're growing this fast, it doesn't mean people are losing their job. It just means they get to now learn from a rock star who's done the next journey. And, and I think if you're hiring really good people, they want that more than their ego. We all have our ego, but they'll swallow the pride and be like, I'd rather learn from Alisa because I'm not really ready to be that C-level person anymore at this stage, and that's a great once-in-a-lifetime opportunity to do that. And if they don't, then usually I find that it's like, awesome, like that, let's part ways because it's just not going to work out. We're not going to accommodate the company's growth to your ego, right? And so I think that was one. The other framework I intersect that with is there are some jobs where scale experience matters at this scale. There's some jobs where it actually is more still vision and intuition, and generally You know, roles related to product— and this was great coaching from this founder— roles related to product are often the scale matters less than the vision and the understanding, the radical understanding of the customer. But when you're talking about sales or operations, yeah, it's hard to know how to lead a 1,000-person sales team if you've never been in a 1,000-person sales org. There's just like a math equation to this. You don't have to be the person who led it, but you probably need to be on that train that rode it and saw it happen. And so So I'm constantly trying to interface and intersect those two frameworks as we think about our team. Uh, it starts though with a really clear-minded understanding of what is the job to be done at the next stage. And I think then an emotional KPI that one of my board members gave me early on, which I really, you know, did not like in the moment, which is, Alexi, are you pulling your team forward or are they pulling you? And if the answer is you're pulling your team forward, you have the wrong team. Right? Because we gave you— we're giving you millions of dollars for them to pull you forward because you've never done this before. So you're supposed to go hire experts who are supposed to bring your vision to life. You're not supposed to go do everything. That would make no sense. We would not give you money to do that. And they said this very nicely, but that was the subtext, right? And so they're really right. And in the moment it was like, oh no, I'm just helping them. But it's like, no, like your job is to be the visionary. That is your job. Your job then is to get that capital. Your job is to invest that capital in a way where people who are better at executing and delivering that vision that you can learn from are pulling you forward. That creates this synergy loop with your vision getting sharper and more real. And that feels emotionally— I coach managers on this all the time— just live with that feeling. Are you pulling these people or are they pulling you? And it should feel like I can barely keep up with this team. That's awesome. That's the feeling you want. And like, you go pull founders, like, for no one is that— it's always like, no, I'm pulling like half these folks, right? And so that's a real check. You've then got to go to those frameworks. Why is that? Have I upgraded the team? Or do I have the right scale factors? Starts with what is the job to be done? What would them pulling me look like? What would that emotionally feel like? Then ask myself, can I coach this person to get there? Or has the person— no, like, I just can't coach you from running a 100-person team to a 1,000-person team. In the timeline we need, which is, you know, next week. So not going to happen. Right. And so you then kind of can go through this decision triage.

So then have you ever coached somebody to be that person who can pull you forward? Right. And that you saw the person wasn't doing that, you had the conversations or did some intervention and that person became that rock star. What was that like?

Yep. It's really cool. It's super fun to see. It usually starts with people who are eclectic learners, I find. They don't define their identity based on a functional role. And I think this is key. One thing that works against professional operating executives, I find they hit a self-sealing, let's call it that, where their identity becomes their limiter to growth. I am a for-hire enterprise CMO. I am a for-hire channel leader. But the reality is that doesn't mean anything. Like, what is a channel leader? It means literally nothing.? And they're gonna be like, no, you don't know. No, like truly every company channel means something else. So like a channel leader at our company may not really correlate that much with a channel leader somewhere else. We're being really— I mean, that's more than probably being like a paid penguin at our company or like a bowling alley attendant. Like, yeah, but like generally every company is a dynamic re-instantiation of a class, right? And so like You have this class to use object. Okay, you're— that changes it. And so what does it really mean? The people who don't get tied up on the identity, I find, and are like, you know what channel means at this company X? Whatever it takes to sell through a channel. That's what channel means here. When people can do that gymnastics, I find they, they're much more coachable and they're much more likely to share. When people are like, no, no, channel means this, we need to do it in this way. And I'm trying to conform the business to my zone of comfort and what I've done in the past, they're more likely to cap out. And it's subtle, right? It's very, very subtle. Most people don't even realize they're doing it. But you really got to start backwards from the market, the customer. What is it from their view, not what it is from your resume view.

But what I guess on the other side of that, certainly you just had moments where you just realize this person isn't going to make it or they have the agreement What does that conversation look like?

Yeah, I mean, I, you know, hopefully it's not like a ton of bricks because they, you've, you know, I think when it's done well and I've done it well and I've done it poorly, I think when it's done well, there's a, in a way there's, you're removing the suspense because there's individual items that it's been really clear on. Like, hey, we agree that was not done the way we need it. Maybe there were mitigating circumstances. We're organizing to win, showing up resources. Is, but it's this gradual understanding. And I think when it's done well, um, they tell you. You start to hear things like, hey, I may not be the right person for this role going forward for the company. And I've had, I've had more than one executive tell me that. And it's like, okay, you know, I've made the mistake of being like, no, no, of course you are. I think as I've made mistakes more, it's like, well, let's sit with that. Like, why do you think that? Let's really unpack. That's actually You know, maybe good self-awareness. Like, I think that's when it's done well and it's predicated on that feedback and that objective referencing to really objective performance where it's depersonalized. It's like, yeah, I'm missing goals or I can't hire fast enough. And like, at some point, whether it's this, this, or this, it doesn't matter. I get it. As CEO, like, you just need this done and that is not happening. It doesn't really matter why at some level.

So when you have to initiate that conversation and have that conversation, it's the same thing, right? You have the analytical framework of this is what's necessary. Hey, you're missing goals. I wish it weren't true, but it is true. We're gonna have to make a change. Is that pretty much how you do it?

Yeah, the one floor is if I have to do it like in one fell swoop. Again, this is my current thing. I haven't had to do this recently, which is great, but because I think I'm getting better at the coaching part and the hiring part, um, and it's hard just to put a pause of empathy. Like, it's hard. Like, you're putting yourself out of a job due to your own great performance in some ways, right? You're like, I helped this company grow exponentially I mean, it can feel really rotten to be on the receiving end. It's like, well, thanks for the thank you. You know, it's like— and, and then again, it usually doesn't have to go draconian things of like you're losing your job. But sometimes with really senior executives, there is no other role because they're like, I am— again, identity— I am a this, and there's only one this at every company, so I gotta leave. That's to my earlier point, it makes it harder to scale the company. If you're like, hey, I'm a business leader and I'll tackle any problem you give me, then there's usually a lot more utility to those folks. So But to your point, the one flourish I would add to what you said is I found it's helpful for people. It's helpful for yourself first and foremost to do this with integrity and clarity of mind to say, what does the future look like? Not— don't talk about their performance. What does the future look like? What does this function look like in 12 months, 24 months? If you're a C-level executive, your horizon is 2 to 3 years. You should be thinking and operating on. If you're CEO, it's a decade. If you're a VP, maybe a year, right? Like, Where are they altitude in the organization? What does that horizon look like from my vantage point as a CEO that I need? I'll— we need this change, we need this upgraded, we need to get out of this business. Then ask yourself, despite their performance, do I believe in this person's potential to do that? Of course, their performance is a feedback into how— and if the answer is they're grossly behind today, explain that. If the answer is like, look, there's been some trip-ups, but I think with coaching and support, they could get there. Maybe I'd have to switch this, I have to switch that. You have to decide with executive judgment, do you want to go down that route and play that game? And I've seen it work and I've been burned, right? Both made both mistakes or both ways. But I find when you start with that vision, it allows them to mind meld and it's like a safer conversation around, okay, Alisa, let's put our heads together. Like, do you agree with that vision? And maybe they're like, no, that vision's terrible. By the way, here's why. You should be like, okay, well, maybe I don't need to change this person because my vision's wrong. Wrong and they're actually right. What you often will find is you've talked to your board and you're like, yeah, that vision's right, and they'll be like, you know what, that vision is right. Then it's a pretty honest conversation. Do you think you're the best person to go do that?

That is great, although difficult. To your point about empathy, it's really hard. It just is.

It's so hard. You care so— I mean, these are— I was talking to someone today in an interview and she, she brought this up, you know, she's been at some high-scale companies and she was just saying how hard these conversations are, and we were comparing notes, and I was like, you know, it's, it's like you're with your brothers and sisters in arms, and then it's just like, you know, we got to let one of you go. It's real— it's really, really, really tough. And, and you try to celebrate that, you're trying to honor their legacies, their contribution, um, and you try to set them up for success. Because what you're really saying, if you believe in that vision, is you will not be successful here, right? And— or at least in this role. Hopefully maybe somewhere else at the company, at least in this role. And that actually is a kindness to them, right? This is Brené Brown, clarity is kind. Like, that's, that's a kindness to them to just stop beating around the bush, uh, and just let them know that. Then you can turn the conversation to where could you be successful here, right?

Totally. You know, you've talked a lot about— so you've talked about having a new executive team, which it sounds like it's working really well, and you've talked about doubling the company every year. So what I have found with my clients is that there's this the old-timers and the newcomers. And there's different like archaeological layers, right, of the old-timers and the newcomers and the old-timers. How have you— have you experienced that at BetterUp? And how have you thought about integrating newcomers, especially in light of what I know you consider to be a very distinctive and important culture?

Yeah, I love that metaphor, archaeological layers. That's really cool. Um, okay, so let me think about— so this is what's interesting. We talked about upgrading the team, but I, I do want to put this in proportion in case it's helpful for others. This isn't always as extreme or radical as it seems. Like, if I think about our 8 senior-most executives, 3 or 4 of them are still like old-timers or advisors who were involved, who got pulled in along the way. So like, the upgrade has not been like 100% switch out. The upgrade probably it hasn't been intentional in this way, but statistically it's probably been like every 18 months one is rotating on or off. And many are just rotating the layer below in the company, right, as, as they get layered. Some are rotating out of the organization for whatever reasons. So I do think that's, that's important, right? We have not— I mean, maybe I have a blinder here. I think the answer is we have encountered that less than many organizations. And I think if I could hypothesize as to why, there's maybe a twofold explanation. Um, we got a little bit of that a few years ago. Uh, like, you have to ask, why does that happen? Well, it's not the new timers. You just paid them a lot of money and invited them to come work here and create value. They're excited. Guess who's the problem? As a CEO, you should be very clear, it's the old-timers. It's what I call cultural nativism, right? Like, you can't allow it. And so we did have a little bit of that early on, um, but it was really a bunch of old-time low performers who were threatened and scared about their job. Right? And so, um, I think when we performance managed and did our jobs better as managers, magically the problem went away, right? And so that wasn't— that's in retrospect— that wasn't like the goal in doing that. I just, in retrospect, as you asked, my first impulse was like, we've never had that. I'm like, oh no, you know, there was that like 6-month period in 2000— was that '18-ish? I remember hearing a little of that. I also remember upgrading our performance management and it magically went away. So I think part of it is, you know, if we talk about these leaders who are here and still leading, it's a credit to You know, I'm onboarding a new C-level leader right now. She's like a month in her tenure, amazing leader, and she's just brimming with new ideas, right? This is why you hire these people. They're better than the average, better than you. But, and, you know, she's coming from a larger company. She's sending me some of her great ideas. Hey, I think in this function, and I'm just like, hey, go share it with your peer. And, you know, there's a little bit of like, I don't want to step on anyone's toe. Understandable. She's being super conscious and respectful. She goes and does that. Saying like authentically, wow, like that person is taking time on my calendar now. They actually are thanking me and they're changing their whole Q2 plan based on this idea. Right. And it's like, okay, that's not a credit to— like, yes, it's a credit to her in a way. So that's great. She's being an extreme owner. She's sharing that feedback. It's really culturally, to the heart of your question, a credit to that leader who says, I just want to service the mission and it's not about me or my plans. That when you find those people who then can pair that with the learning agility to stay, that's why a third or half of that leadership team have been here 4+ years because they are those people. And it requires a level of ego management, selflessness, and I think really an enthrallment with the mission, not just a general like, mental health is cool, we want to help people. Like, I like your mission. Who doesn't like our mission? Do you not want to help people? But more like this really intersects with my life's mission. And so like, I want to be on this bus, like, and I will give it my all. And ooh, that is like, that's what makes startups fun. I mean, I have been in literally numerous sales meetings at BetterUp where heads of sales are arguing over opportunities that they should live in other people's territories. I never had that at any other company. It was always like, stab in the back. That's my lead. No, it's like numerous occasions. And I've had other leaders who are new comment on this. Like, I've never seen this where it's like, It's like, you should take the opportunity. It would be in better service of the customer. No, you should take it. And it's like handing million-dollar deals over the fence because it's better for the customer. That's a testament to those leaders though. They create that culture and they're the— and then when you're the new person and you come in, wow, I'm invited to actually bring great ideas here.

Yeah, that is magical. I'm totally inspired by that. But I think it's also just a testament to the culture and also a testament to who you're hiring. So, I guess I am interested in, you know, we talked about this when I interviewed for my book, From Startups to Growing Up, like 2 years ago, I think. It was probably about 2 years ago. And you told me about your cultural values. You talked about your balloons and how you made sure you integrated the values. What is the update on how you hire for culture at BetterUp? How have you improved in the past couple of years?

Yeah, I mean, we've just leaned into it more, honestly. So, we still do balloons. We're constantly retooling, retraining. Explain the balloons.

Explain balloons.

Okay, so Balloon, I got this idea. We called it Balloon because our original logo— I will be very— I got this great idea from Josh Reeves, who's a friend and the founder of Gusto. So I can take no credit for this. He trained a squad of early employees. Amazon has the Bar Raisers. In some ways it's similar. Like, you know, early on Reid Hoffman will say, Anil Bhusri will say, like, you should interview the first 500 employees between 250 or 500 employees. And Eddie and I committed to doing that. It's exhausting, but it's worth it. At some point you become a bottleneck. And so this balloon mechanism is a way to, uh, deputize a small group of cultural co-founders who are not interviewing for the job, nothing related to job skills. They're interviewing for mindsets, learning agility, and alignment around that mission. And, uh, by definition, they can't be from the function of the person. So functional bias— oh, they're a good engineer. No, this person's from comms. They don't know what a good engineer is by design. They just know is this person really fired up and like excited to come here and learn and grow and all the right things. So that's our balloon process. Every interview process, they're inserted. They have single veto power over the interview process. And so we've actually had that, and now we've added a bar raiser. So we still call it founder's interview, but it could be myself, Eddie, or we deputize a small group of early employees. Not that early, I mean, this is over like a 4-year span. Who we think are really good standard bearers of the cultures and the values. And what we've seen is, I think the culture is getting better in terms of closing the gap between how we show up every day, which is your culture, and the values we espouse. And one area of that where we've been really intentional, I think have made great progress, really the team's made it, is, you know, we were pretty squarely— I would pull some employees in their onboarding, like one month in, 2x2, Kim Scott, check where BetterUp is, Runa's Empathy, Radical Candor, you know, I, I don't even remember the other two because we were never there. And it was like 90% of people ruined his sympathy a month in, knew that about BetterUp. There's a bunch of nice people who aren't going to tell me— yeah, who aren't going to tell me that I'm going to get fired, right? And so actually, they probably won't even fire me. Like, that's how ruinously empathetic we were, right? And so, um, now when I do that, 90% radical candor, right? And that was a 4-year journey, and it involved a lot of tough conversations, a lot of tears, a lot of enablement, a lot of training, a lot of people people, Eddie and I hiring leaders who are better at this than us because we clearly weren't great at it. Eddie's better than me. I clearly was the problem. So hiring a lot of these people that we can learn from, what do these repertoires of skills where you can hold both and really provide that clarity in a kind way. A lot of coaching from Fred Kaufman around conscious business and, and trainings and enablement there. So I'll give that as an example. And then we've learned from that and we're able to then like, hey, how do you productize that in the hiring, training managers and item scales, situational interviews to do that.

That's great. I love the process. I love how process-oriented you are. I just talked to actually Paul English, the co-founder of Kayak. And his thing is that he wants to hire somebody, he wants to make an offer 7 days from the day he hears their name, which I love that.

Oh, wow. Good for him.

But what he said was fast does not mean sloppy. You know, pit crews for F1, for F1 racers have to be fast, but they can't be sloppy. So, you know, really requires process and, to your point, training and everyone knows how to do it and the right people in the right roles and all that kind of stuff. So, I'm really excited about what you're talking about. You know, you talked also about radical candor and runosopathy. One thing I would say about founder CEOs in particular is that it is hard to get your people to tell you the truth. Your board members may, your advisors may, that one kind friend of yours from VMware long ago, right, she may. But how do you get your rank-and-file employees and your executives to give you difficult feedback that makes your life better, even though it's hard to hear?

Yeah, I mean, I think, you know, I'll share what we try to do. Time will tell if we do it well. And just for the record, I'm terrible at processes, but I have a great co-founder who's awesome at it and hired people who are way better at it.

That's what matters.

So, yeah, exactly. Okay, so I think it's a combination. So, you know, I think you need some formal systems to do this, and we can talk about that. And I also think there's some cultural practices that can help this. I mean, the real technical answer is they strictly speaking don't need to tell you if you have a great cascade. If you go, you know, we're big fans of Roger Martin. If you read The Execution Trap, this is the job of middle management is to not just cascade down mandates. That's actually not the job. Cascade down commander's intent to use the military framework. Work, um, but cascade up operational field realities that you may be missing in the hopefully not ivory tower at the top. And so part of this is actually, I think we'll talk about maybe sometimes you need some ways to prop that up, but the actual healthy way, the metabolic way, the organic way, is have really good functional middle management. That's what good middle management does. It becomes an interface that bridges the power distance between, hey, I'm a frontline employee who may be 22 and this is my first job and you're a 1,000-person company, 10,000-person company, there's a CEO. And so what we found is all of our manager enablement is really centered around this philosophy from Roger Martin of the cascade. How are we cascading choice architectures and empowering people to make those decisions? And how are we cascading up feedback on those choice architectures in the operational realities? And, um, it's not perfect, but I think having the awareness and intentionality around it is key. One way to do that as a manager is in a way like require your direct reports. One way to evaluate your team, and I do this, is what is the level of insight and contribution they bring? Not just what they do. Like, do you learn about your business from these folks? If you're always telling them about your business, you have a problem. They're closer to your business. You're not your business. You're like at the top of the pyramid in most companies. Your business is the customer, right? So they should know more about your business in many senses. You should know more about where you want your business to go, maybe in the future, in the market, and maybe things like that. So I think it starts with managers really, in a sense, creating the space as well as role modeling the behavior of, I want to learn from you. Like, what have you been learning from your people that you can share with me? And it's easier to start that with the customer, but when you get that behavioral loop going, then that can be extended internally to the culture.

Mm-hmm. Right. And then people sort of begin to get in the habit of sharing things which are maybe insightful and then maybe controversial and maybe difficult then to hear.

Yeah, that's right. And then look, I think when you're growing fast, you probably need some, some safety release valves, right? So hey, we, we do ideas contests for best ideas, right? This is a way that there's like, get to the front line, they can get an idea visible to the CEO, right? We do a ton of spot bonuses for great work, right, where leaders can nominate for. So there's things like that, you know. We have things like this great product All Voices, right, where people can raise— I think it was intended more for whistleblowing, but you can use it for anything. So we have great ideas on where managers can improve, things like We're doing 360s. We're a big fan of those, right? So leaders and managers doing 360s— our own product has a developmental 360, but then also doing those formally too. So I think there are, you know, that's just— we don't live in an ideal world. That would be the idealized answer. But structurally, I was in a meeting— skip levels, not just 2 layers down, but 2 layers up, right? Like help people get visibility into what their boss's boss is focused on. That empowers them and that allows them to give that reverse mentorship and feedback. So So we're trying to up our game here. It just gets— you got to do it faster as you scale. But I think it's a combination of these cultural practices that you normalize by setting the tone at the top, but then because you're growing so fast, some of these structural safety valves to make sure you're not missing out on really good contribution and really good ideas at every level of the organization.

Yeah. Oh, that's so great. Now, throughout this whole conversation, you've talked a lot about different mentors and friends and, again, your board and your advisors and people around you, your network, basically. I guess I'm curious, like, when did you realize how important it was going to be for you as a founder CEO to build a strong network? And how did you go about— did it just happen organically or were you intentional about building it?

Last part first, we were intentional. Um, it also happened, you know, or through time organically. First part, I was a little precocious and fortunate. I mean, I learned, I would say, 7— when I was 17. Like my, my buddy who, who started the nonprofit where we're doing the afterschool coaching. I mean, John, he's a force of nature. I mean, he was being mentored by city council members, you know, Kiwanians, Rotarians. And I, you know, he kind of just pulled me into that loop and was mentoring me even though he was only a year older. He's one of the most significant mentors in my life. And I saw through him the way he was able to grow so fast. Was because he had all these beautiful inputs from, you know, elected officials, business owners, all this stuff. And so I think I was just through serendipity, really fortunate early on to see the power of mentorship and, and learn this little secret in life that, you know, people don't really bet on people who have the answers. Uh, people bet on people who have big dreams and the wherewithal to do whatever it takes. And there's a world of difference in there. And, you know, John and I and the group of us who built this nonprofit in high school, we didn't have any answers. We were like 17. We'd go pitch the city council dumb ideas all the time in retrospect. But like, people saw that and they bet on us because they're like, these kids want to go do something and help their community. And it doesn't matter if the idea is right. Like, who am I going to bet on? I'm going to bet on these annoying kids who keep showing up to every council member meeting, take our feedback, and then go get better. And that formula, I don't think changes when you're 30, when you're 40. It doesn't change when you're raising money. Like, the old adage is true. If you want money, ask for advice. If you want advice, ask for money. And I think there's a lot of truth in that. So when we built BetterUp, it was almost just like pathological that like that was kind of already my MO in life. In fact, one thing I regretted being an operating executive when I was going through this acquisition is I had winnowed just due to my time. And so a big goal in leaving was I need to get back to reconnect to that like root system and get those inputs. And I had made some bad decisions in life. I realized because I had cut myself off. I wasn't spending the time to get the investment. And so I think it was pretty organic is the answer. It, it, it started slowly and, and, you know, now it's to the point where I have to go look, we're probably 50+ formal advisors to BetterUp, well beyond that.

Wow. But you also have these other, you know, just friends and people in your life who, you know, you obviously are connected to, who I think are constant inputs to you, it seems like.

I think so. Yeah. Mentors, right? Like you kind of have, you know, whether it's the formal personal board of directors, you know, in your life, there's— you should, I think, know, like, who are the 2 or 3 people you call on any subject matter, and do the work to get the, to get the help. I, I'm, I'm a bit of a ruminator, so it's easy for me to just kind of wallow in self-pity and ruminate. But the reality is, a lot of these problems, people have solved who have already gone through them. And if you just pick up your phone and ask them, they're really— again, they're happy to bet on you, and they're happy to take the time All you have to show them is that they were heard and you actually did what they said. Like, maybe not in total, but you— like, at some point— I'm coaching Alisa Cohn. If she never changes her behaviors, I stop coaching her. It's a waste of my time if she's not paying me. If she's paying me, maybe it's great use of my time, but even if I have a lot of options, it's a bad use of my time as a paid coach, right? But when someone's mentoring you for free, what you— you don't owe them, but what they're going to be watching for is, does this young whippersnapper, or does this person who's more junior than me or new at this, do they incorporate what I'm telling them? And when they do, they're going to keep leaning in and investing. And you don't do it for that reason. Hopefully you do it because you learn, wow, they're right and they're sharing wisdom and I should be so like benefited to learn from it. Awesome. But I find that that's the formula.

So just a couple more questions, Alexi. What do you wish you had known earlier on your journey?

I think one thing I knew it, like I've been reading leadership stuff since again, I was like 16 or 17, but I didn't like, I knew it intellectually. I don't, some days I wonder, do I still know it in my bones? But it's like the job is to do what's right for the mission. And most people aren't gonna thank you for it. You know, and we have so many built in, at least I had so many built in heuristics and KPIs of success is approbation or approval, right? And the reality is those will deceive you because if you're doing something that's never been done before, people don't think it's going to be successful. So they're not going to approve of what you're doing. They're like, you may drive a car off a cliff. We're not going to approve of that. We don't know. So we're going to tell you like we're uncertain or we think it's a bad idea or all these things that tell you don't do it. And I think I, I think I always viewed that as mistake, instead like a flaw or a bug, not a feature of the journey. And I wish I would have took it more as, that's what it's supposed— that's actually doing it right. That's what it feels like. It's a function of the novelty of what you're doing, not of how poorly or well you're doing it. And don't get me wrong, it's not like anytime someone gives you bad feedback, you're like, that's because I'm so innovative. No, that's like a self-serving myth. But I over-rotate it on like Oh, okay, I must need to stop, or, oh, they, they, you know, I was too timid in retrospect. Um, and I think that in particular extended to people decision. I got some really good coaching from one of our advisors. I mean, it's good, you're gonna laugh when I tell you it, but he's like, um, do you, do, do you really expect like the people you have to let go to agree with you that you have to let them go? Because it feels like you're like waiting till they agree with you to make the decision. And yeah, let them know. And I was like, I actually was. I, for me, I'm a very rational person. I like to think I'm like, they should just come to this. And if they don't, maybe my conclusion's wrong. And he's like, think about that. Like the fact that they can't do like perform in the role probably means they're not appraising the data in the same way as you. So they're never going to come. If they do, that's a huge credit to their self-awareness. Awesome. But like that can't be your emotional standard or even your executive standards. You have to do what's right for the business. You have to be fair. You have to communicate with them. If they don't understand it, that's probably a feature, not a bug, you know? And I think you could say, hey, if I was, you know, the Dalai Lama of management, I'd lead them all and they'd all be like, thank you, Alexei, we're so thankful. And, you know, like maybe in a decade they feel that way. But for the most part, you know, most people in the moment just are mad at you, understandably, right? It would be inhumane to expect them to be something else. We're all humans, right? And so, and you might be wrong, but whether or not you're wrong, you still— it's your prerogative to make the decision, and you have to do it, and you have to learn to be wrong so you can get better next time. That's the sad cold truth of it, right? And so I wish I had known that it's leadership, it's not being liked. We have different words for it for a reason, and, um, you get more comfortable with it. But I think this is one of the biggest mistakes first-time managers make. They think their job is to get people to agree with them, and it's not. I'm not saying be a dictator. I'm not saying be a tyrant. You should do the work to find agreement, but that can't be your measure. Your measure has to be the soundness of the decision, or do you feel like this is what's best for the business? You should spend the time to bring people along, but when push comes— and usually for most decisions, you will find there's agreement, by the way, if you have a really good team and you're really communicating.. I've spent a lot of sad nights of my life trapped in the wrong paradigm. And I think BetterUp for me would've been a probably, you know, it's been the ride of a lifetime, but it probably would've been a more enjoyable experience in my own head had I learned that sooner.

Yeah. Very well said. And you're not alone. Very well said. That's a helpful paradigm for sure. Now, Alexi, last question. What advice do you have for other founders as they embark on their journey to grow into leaders?

I mean, it's kind of— I don't say this in a self-serving way because we don't really do a lot of this coaching, but like, get a coach. Like, I mean, I— you, you apparently can do this by yourself. I don't know how people do it. Like, there are single founders who don't have coaches who build great companies. They're clearly superhumans and better than me. But like, I, I couldn't do it without Eddie, and I certainly couldn't do it without coaching. I mean, I started this company out of my experience. I could barely do myself. You know, without coaching. So I think it's get a coach. Like, the job is really hard. There should be no pride or machismo in how you do it. It's really just like, if you do it, you like, you've done something that's so incredibly hard. I don't think Tom Brady is like, I won a Super Bowl without a coach. I'm the greatest Super Bowl winning guy because I don't have a coach. He's like, dude, I'll take all the coaches I need and I'm going to win more Super Bowls.

Goals.

Like, it's pretty simple. I, I don't think he prides himself— I don't know the guy, but I suspect he does. And I've never met an elite athlete— I've gotten to meet quite a few in going through this journey, um, that feel that way. And so I would say, like, get yourself a structural mechanism for that accountability, feedback, and support. And that could be a therapist, but, you know, I, I— and maybe it should be. I've used both at times. But for the leadership, the journey, I think a coach is the really the right formula for that. To focus on proactive, future-oriented behaviors and how you scale those in your organization. Every skill, every lesson you can honestly, like, learn on YouTube these days. That's not the hard part. The hard part is applying it with consistency and getting better at it. That is not a learning— I mean, it is learning, but it's not a knowledge transfer problem. It's a behavior change problem. And the intervention for behavior change is a coach, a personal trainer, something like that. It's not a textbook. And so we over-rotate on knowledge in the one area of our life which by definition relates to not books but people. And coaching is the right intervention to really get that out of the book and actually get you doing it day to day.

Absolutely. Alexi, what a joy. I can't even tell— it's a masterclass on leadership and on starting a— founding a startup and growing a startup. Thank you so much for joining me today.

Well, thank you for having me. This was a lot of fun.

Thanks for listening to From Startup to Grownup. If you like what you heard, give it a review on Apple Podcasts so other people can find it. And if you know of a founder or someone else who is meant to be on this podcast, drop me a line through my website, alisacohn.com.