Skip to Content

Scale yourself first, and then your business


Before you can help others grow, you must be equipped to take care of yourself. This is far from a new concept for Alexi Robichaux and Prince Harry, BetterUp’s Chief Impact Officer. They both share stories — from their own lives and others’ — that exemplify the value in adopting the right mindset for growth.

“It’s incredible how with a little coaching, you can unlock creativity and energy in someone.”

— Alexi Robichaux
About the guest:

Alexi Robichaux is the co-founder and CEO of the coaching platform BetterUp. He was previously the Director of Product Management at VMware. Alexi is also the Chairman of Youth Leadership America, a nonprofit organization that he co-founded in 2003.

About the host:

Reid Hoffman is the host of Masters of Scale. A Silicon Valley entrepreneur and investor, he’s known for his spot-on insights on how to scale a startup. He’s a partner at Greylock and co-founder of LinkedIn, and co-author of the best-selling Blitzscaling and The Startup of You.

In order to scale your business, you must first scale yourself. Which means, adopting the right mindset — or rather, a series of mindsets — for growth.

Transcript of Masters of Scale: Scale yourself first, and then your business

Chapter 1: The Invictus Games

PRINCE HARRY: We were down in this tiny little military barracks room, almost like a cell. The guy who had the injury, he was physically shaking. He was unable to look me in the eye. He was very visibly suffering, and he had what was called PTSD that rolls off the tongue for everybody. 

REID HOFFMAN: That is the unmistakable voice of the Duke of Sussex — you probably know him as Prince Harry. And the story he’s telling, set in a dingy barracks room, captures an under-told part of his service with the British Armed Forces.

PRINCE HARRY: I was going to a barracks in London, and as part of their personnel recovery unit, I was doing interviews, kind of, or just meetings with individuals who were suffering, mostly from psychological injuries that had either come from a physical injury or otherwise.

Listening to their stories, I started to realize parts of my own story were being mirrored or reflected in that.

HOFFMAN: Prince Harry has been a longtime advocate of mental health awareness — in part, because of events he and his family have weathered under an intense public spotlight.

His advocacy led him to many conversations with soldiers suffering from Post-Traumatic Stress Disorder. But that particular soldier he’s been telling us about had a surprise in store for Prince Harry when they met a second time. 

PRINCE HARRY: It was maybe four months later or six months later after he came back from a ski trip, had basically almost completely healed him. He came back, and he was a different person, it was like I was speaking to his twin brother. But it wasn’t, it was the same guy.

HOFFMAN: It seems incredible that such a dramatic change could happen because of a ski trip. And in fact, there probably was a lot of work and healing that happened around that event. But something about that trip had kickstarted the change. 

PRINCE HARRY: That’s the power of sport. It literally has the ability to completely transform an individual.

HOFFMAN: Watching this transformation put one very important thought into Prince Harry’s mind. 

PRINCE HARRY: Why do we keep calling it PTSD? Why do we keep calling it a disorder? If you’re going to turn around to someone and label them with a disorder, that’s them screwed for the rest of their life. Why are we not calling it PTSI? It should be an injury. And if you’re telling someone that they’ve got an injury, then guess what they’re going to do? They’re going to try and get better.

HOFFMAN: What Prince Harry’s describing is more than just a shift in language. He’s talking about a shift in mindset. This simple word change from ‘disorder’ to ‘injury’ can change everything about a patient’s journey. And he wanted to help others make that shift.

That’s why in 2014 he founded the Invictus Games, an international sporting event for wounded servicemen and women. Some service members compete with physical scars. Almost all carry scars that are mental.

PRINCE HARRY: For me, part of the organizing of Invictus was an opportunity to use my influence, my platform, and my convening ability to be able to find a cure for not just the individual but the families as well.

We had thousands of emails that came in. People literally saying, “I’ve had a broken back for three years. I haven’t been able to get off the sofa until I just saw a double amputee run the 100 meters. So thank you for the inspiration. I’m now getting up off my sofa, and I’m now going to, like, smash life.”

HOFFMAN: The Invictus Games carry a powerful message — to grow, you must first adopt the right mindset. And that’s not just true for athletes. It’s true for everyone including entrepreneurs. 

That’s why I believe that in order to scale your business, you must first scale yourself. Which means, adopting the right mindset — or rather, a series of mindsets — for growth. 


Chapter 2: Adopt the right mindset: scale yourself first

HOFFMAN: I’m Reid Hoffman, co-founder of LinkedIn, partner at Greylock, and your host. And I believe that in order to scale your business, you must first scale yourself. Which means, adopting the right mindset — or rather, a series of mindsets — for growth. 

Think of the last time you were on a commercial airplane.

FLIGHT ATTENDANT: Good afternoon, passengers, and welcome aboard Scale Air’s flight 314 to San Francisco. 

HOFFMAN: Now think of that safety demonstration you definitely didn’t pay enough attention to. 

FLIGHT ATTENDANT: The emergency exits are located in the front, middle, and rear of the aircraft. If you’re sitting…

HOFFMAN: In those instructions, there’s one piece of advice that may have stuck with you.

FLIGHT ATTENDANT: In the event that we lose cabin pressure, the panel above your seat will open, and an oxygen mask will drop down. Be sure to put on your own mask before assisting others. 

HOFFMAN: Exactly! “Put on your own oxygen mask first.” That may have sounded callous the first time you heard it. But it makes sense! Before you can help others, you must be equipped to make sure you won’t collapse halfway through the task.

And this isn’t just good advice for frequent fliers. It’s for entrepreneurs as well. Because becoming an entrepreneur requires cultivating a mindset for scale. It means thinking clearly and acting fast, even when you’re hurtling toward disaster. It also means challenging yourself to think in contrarian ways.

This mindset doesn’t always come naturally. And when you’re constantly challenged to think counterintuitively, it can be overwhelming. You have days when your goals aren’t clear, and your challenges seem insurmountable. That’s when the best thing you can do as a leader is reconnect with your own purpose. You have to find ways to put on your own oxygen mask first.

I wanted to talk to Alexi Robichaux about this because as the co-founder and CEO of BetterUp, Alexi talks about this need all the time.

BetterUp is a platform that lets businesses provide employees with virtual coaching.

And if “virtual coaching” sounds like an army of holographic Dr. Freuds, don’t worry. These are human coaches … a lot of them. Since their founding in 2013, BetterUp has grown the world’s largest virtual network of coaches — over 3,000 and counting. They work in 46 languages, across more than 90 countries. Their enterprise clients range from Google, to Starbucks, to NASA. 

And in 2021, they even added a high-profile Chief Impact Officer — you’ve already heard from him. (Yes, it’s Prince Harry! And I’ll be talking to him again, later in the show.) 

Chapter 3: Be an infinite learner

Alexi started cultivating his own entrepreneurial mindset back in high school.

ROBICHAUX: I had a buddy, John Nguyen. And we went to a lot of these leadership conferences. And Johncame to myself and some other student leaders and said, “Hey, we go to these leadership conferences. And it’s a bunch of old people telling us how to be leaders and they’re like retired senators. And they talk about stuff, they’re like … I don’t even know, do I wear a tie? How do I shake someone’s hand? This is so disconnected from what we actually struggle with.”

HOFFMAN: This was a prescient observation from Alexi’s friend. When you’re first starting out in a new field, you do wonder about the basics. Every business professional has some version of this.

Not only are there things you don’t know yet … there are things you don’t know you don’t know. These are the “unknown unknowns” of building scale. 

An essential scale mindset is one built around infinite learning. It welcomes beginner questions, and a beginner’s receptiveness to new information and new patterns. 

This is exactly the kind of mindset that guided Alexi. He ended up being so inspired by his friend’s leadership club, he became a co-founder. They called it Youth Leadership Anaheim, or YLA.

ROBICHAUX: We regularly met with members of the city council. The mayor became a mentor. You’re 16, 17, that was a big deal. Disney was a sponsor because they were in Anaheim. Hilton was a sponsor. So it was a huge experience.

HOFFMAN: Having that early foundation in entrepreneurship helped propel Alexi through college and into the professional world. In fact, Disney is exactly where he started his career, as a young executive. 

ROBICHAUX: I think it was a true gift in retrospect to have started my career at one of the best-run companies in the world. And I find many people in the start-up community have never had that gift. And so you’re building towards a mess. And all early start-ups are a mess, but you do actually eventually want a well-run company. And so I almost got to do it backwards. 

HOFFMAN: This is an interesting perspective. On the one hand, the rule book for becoming a successful executive can sometimes vary from the rule book for becoming a successful entrepreneur. Certain corporate environments are notoriously conservative and can even present headwinds for entrepreneurial thinking.

But, if you go in with the learning mindset we were just talking about, why not take lessons from a world-class, scaled organization? 

ROBICHAUX: I got to see what a well-run company with predictable growth year over year looks like, but I was in Walt Disney parks and resorts. And our investment timelines were like two decades when you’re building a theme park. And as a 23-year-old it was like, “Wow, I will have to be here 20 years to see this idea pay off.”

Chapter 4: The startup of you: find your mission

HOFFMAN: This moment of self-discovery was important. 

Whether you’re building your first company or trying to spark change inside an organization, you’re on a personal scale journey growing what I call, the Startup of You. (In fact, I wrote a book about it of the same name — now with a tenth anniversary edition!) 

This personal scale is rooted in finding your mission, not just a desire to get to the next rung of the ladder. 

As a 23-year-old, Alexi was on the executive track at a Fortune 100 company. But he recognized in himself that this might not be the track he wanted. 

So he left Disney for Silicon Valley, and joined a young microblogging start-up as an early employee. Its name was SocialCast.

ROBICHAUX: I met the founder, Tim Young, who was this extraordinary visionary. Even just the pace at which he hired and made decisions, I was like, “This is where I want to be.” 

HOFFMAN: Not only was SocialCast exactly what he’d hoped, they were soon acquired by VMWare. And Alexi found himself serendipitously flung several notches up a new corporate ladder. He was suddenly managing large teams of people at the age of 26.

Chapter 5: Absence of self-care will break you

But remember, a scale mindset is actually not a single mindset at all. It’s more like a series of mindsets that let you scale first your understanding, then your abilities. And the acquisition forced the pace of Alexi’s learning to speed way up. 

HOFFMAN: You then take on a much larger kind of job and a responsibility there, but you have a bit of a crisis moment.

ROBICHAUX: With the benefit of hindsight, I would say I was my own crisis.

It’s so weird in retrospect, but my goal was to be the youngest executive at that Fortune 500 company.

And that resulted in me setting poor boundaries. That resulted in me being the guy who had a reputation for, “I’ll fly to Munich tonight, just let me know, let’s go do this. I’ll do whatever it takes.” And essentially I burnt myself out.

I was waking up with night terrors routinely. I couldn’t sleep through the night. I took a PTSD test, and I tested positive for post traumatic stress.

HOFFMAN: This experience may sound achingly familiar. Entrepreneurial culture can be notoriously full-tilt. Hitting or missing a launch window can mean the difference between massive scale, and total ruin. So many of us trick ourselves into thinking a relentless pace is right for us indefinitely. 

ROBICHAUX: I don’t drink, I don’t smoke. I swam like every other day then. And my blood pressure was like, I think they’ve changed the definition, now it would have been hypertension. And the doctors were puzzled. They’re like, “The only thing that can be causing this is stress.”

HOFFMAN: When Alexi finally went to the doctor, he learned the hard way that working to the point of exhaustion was not sustainable … and was actually antithetical to the scale mindset. It’s applying yesterday’s tactics to today’s much larger challenges. And it had given Alexi PTSD.

ROBICHAUX: And I’ve obviously never been in the military, never been in combat. I don’t have any of the normal triggers, but I was experiencing so much of similar symptoms. 

HOFFMAN: If you think back to Prince Harry’s story about the soldier with PTSD, you’ll recall how mental and physical stressors intertwine. And while working in the safety of your office doesn’t compare to being a soldier in the line of fire, your body doesn’t always know that.  

So scaling your workload without also scaling a corresponding mindset of self-care will break you down as surely as any other machine. 

Not only does mental stress seep into the physical… you don’t always notice it happening. Burnout is often less like a raging wildfire, and more like a slowly heating pot of water. If you’re in that pot, you may not notice the water warming until it’s at a boiling point. 

Alexi didn’t notice the extent to which this was happening to him until a friend and co-worker called it out. She was working at VMWare, and happened to be a therapist by training. Her name was Michelle.

ROBICHAUX: She told me something that really just crushed me actually in a good way because I knew she cared so much about me. She was just like, “I’ve been watching you, and you’re not you, and you’re not the same Alexi.”

And it was just, hit me like a ton of bricks, of, “She’s right. I forgot to be me. I forgot to be the guy who coaches people after school and mentors and the person who builds cool stuff. It was a big moment of I guess what we call here at BetterUp now a micro epiphany. She was a coach at that moment.

HOFFMAN: So what did you do with the micro epiphany? What decision, what life change course did that take?

ROBICHAUX: Yes. So typical type A personality. I said, “Well, I probably should leave this place, and go start my own company.” 

HOFFMAN: For anyone who needs it spelled out, this does NOT count as self-care.

ROBICHAUX: I took a big two weeks off so I could rest and recharge and then try to start a company that did not work out very quickly. And then I was really dejected. 

Chapter 6: Observe others’ mindset to see yours more clearly

HOFFMAN: The details of Alexi’s short-lived company are perhaps best lost to history. The important part is what this experience did to Alexi’s mindset. 

ROBICHAUX: I was like, “Wow, what have I done? I left this executive job. I tried to do something, it didn’t work out.” And I didn’t have to work immediately, which was a blessing, a gift, a privilege. But it was actually more like an existential curse at the moment because it’s like, “Now I can sit around all day and sleep late and mope,” which is what I was doing. And so the only thing that gave me joy was I had a ton of time to go coach these kids after school.

HOFFMAN: By ‘kids,’ Alexi means the kids of Youth Leadership Anaheim — now called Youth Leadership America. This is the same mentorship organization he’d helped found 10 years before. 

ROBICHAUX: I was like, “Let me lean into the one thing that’s always been there for me as a source of joy.” And so I started to lean in…

HOFFMAN: As Alexi leaned in, he made two surprising discoveries. Here’s the first:

ROBICHAUX: The incidents of mental health were so much different than when we started this organization. We were bringing in therapists, we were on suicide watches, tragically. It was just like a different ball game.

HOFFMAN: The kids Alexi was now coaching weren’t asking him whether they should wear a tie. They needed help to, in some cases, stay alive.

But even as he noticed this drastic shift in teens’ mental health picture, he also noticed something about his own. This was his second discovery.

ROBICHAUX: I was going through my own languishing and mental health challenges. It was kind of this meta moment of self-awareness when I was like, “These kids have a better ecosystem of support. My ecosystem is: sleep till noon, make myself some Costco pasta with those pre-cooked sausages, call my mom while she’s at work, and rinse and repeat.”

I got to a point where I’m like, “I just want to do something to tackle this problem I’m experiencing in me and in these kids. And if that’s starting a company, then so be it. If that’s joining something, so be it. If that’s just doing this nonprofit and making that my full-time job, so be it.”

HOFFMAN: As low as he felt, Alexi learned something critical in this moment. Observing the mindsets of others can help you see your own more clearly. It gives you the perspective to judge whether you’re truly ready to attack your next scale idea. 

Chapter 7:  In order to scale, you have to do things that don’t scale

HOFFMAN: Part of the entrepreneurial journey is, your first idea isn’t usually the idea that gets you to scale. And so when was it like, “Okay, I’m going to go do the start-up again?”

ROBICHAUX: It was about a nine-month process.

HOFFMAN: In those nine months, Alexi reconnected with another board member of Youth Leadership America, Eddie Medina. And he pitched Eddie a devilishly simple idea. 

ROBICHAUX: The actual first idea was, “Let me take my friend Michelle,” who’s a therapist by training but has business context. She changed my life with one conversation. “Let me take that, and let me do what we did with these kids, but digitize and scale that as a platform.”

HOFFMAN: Alexi wanted to scale coaching as a way to help others cultivate a mindset for success. And Eddie was all in. 

ROBICHAUX: We thought it was just for millennials. For every millennial in the workforce, every millennial who’s self-employed, every millennial would buy this. And we thought it would be direct-to-consumer. LinkedIn was a big inspiration there. It may one day have a B2B, but let’s just go to the prosumer and have them buy Michelle on a phone to help change our lives.

HOFFMAN: But short of cloning Alexi’s friend Michelle, they weren’t sure how this could scale. 

ROBICHAUX: Eddie and I, having too many Excel skills, convinced ourselves it was a terrible business. There was a human in the loop, the margins were terrible, it would never… I’m not joking, we basically convinced ourselves out of what BetterUp is today.

HOFFMAN: If you’re a regular Masters of Scale listener, this moment might sound familiar. Because one of our founding beliefs is that in order to scale, you have to do things that won’t scale. In fact, it was the topic of our very first episode in 2017 with Brian Chesky of AirBnB. Unfortunately for Alexi and Eddie, this was 2013, so we couldn’t yet share that advice. 

ROBICHAUX: We built the world’s worst app, Duolingo for life skills. Just pause and visualize the terrible UX of doing a Duolingo experience for negotiation. “What is your BATNA? Fill…” It was terrible. 

HOFFMAN: That does sound pretty far from Alexi’s first idea and the mission that helped him break the cycle of Costco pasta and despair.  

But the co-founders of BetterUp wouldn’t be the first to talk themselves out of a good idea. 

HOFFMAN: Many startups have elements like this. PayPal did. We originally thought we were going to be a bank, and then it was like, “Oh my God, we’re going to go out of business. Well, shoot, people are using us for payments, we’ll become a master merchant.” And we got like two months.

ROBICHAUX: I never knew that.

HOFFMAN: Yeah, we got two months to do it, otherwise we’re dead.


HOFFMAN: Right. So this is actually not an atypical entrepreneurial experience.

ROBICHAUX: Well, that makes me feel a lot better.

HOFFMAN: So go in a little bit, “We’re going to do this great economic model of a platform that’s a marketplace that’s consumer education. Oh, shit, we don’t have buy-side demand, it’s not working.”


HOFFMAN: “Okay. We’re going to do this, and this is our hail Mary.” What was that thinking, moment, action?

ROBICHAUX: I was loaning Eddie money. We were trying to liquidate 401(k)s. And we’re both 26, 27. We didn’t have giant 401(k)s. We were living off 0% interest credit cards. They were very plentiful circa 2013, if you remember.

We basically had lost our first engineer. He had to go get a real job. And I actually remember the conversation. I remember telling Eddie like, “Hey, man, remember when we first started, we built two decks?” And they both had the same pieces. They always had three Cs of BetterUp, coaching, content, and community.

And we went with the content and community as the better economic model and upsell to coaching. I was like, “Man, I mean, we could just fire up Google Hangouts and like a paywall, and just start video chatting. And I mean, give it a shot. We got a little money to run Facebook ads. And so we’re like, “Okay, let’s just try it.”

Chapter 8: Be flexible and responsive to your customers

HOFFMAN: As Hail Marys go, this is a good one. For a moment, they abandoned building an app, and instead offered customers one-on-one video sessions with a qualified coach. And one of their first coaches? Yep — Alexi’s friend Michelle. Desperation, as it does for many entrepreneurs, had forced them into a mindset of bold action. So, did their Hail Mary work?

ROBICHAUX: Night and day difference. 

Eddie and I are not marketers. We were the matching algorithm. We were having a conversation with every one of our users out of necessity, and we were hearing what they wanted, and it validated what we always thought they wanted. And then they’d go talk to these coaches, and we were like, “We never got this when we showed them our Duolingo thing. They didn’t even use it. This is amazing. They’re actually having real life-changing conversations in their first experience.” So, that was like, “Okay, wow, we stumbled upon this somehow.”

HOFFMAN: They may have stumbled upon how to build their minimum viable product. But I’d argue they didn’t actually stumble into their core concept at all. Because it’s actually the concept they started with. 

Their journey away from that first concept and back might have been painful. But it was also how they came to recognize which part of their idea had value. This mindset of flexibility and responsiveness to the customer is occasionally borne of desperation, but that’s OK. However you come to it, it’s one of the most important mindsets you’ll need to get to scale.

Coming up. we’ll hear how this new scale mindset helped BetterUp on the next phase of their journey. And there’s more coming from BetterUp’s Chief Impact Officer, Prince Harry. 

PRINCE HARRY: You talk about it here in California, “I’ll get my therapist to call your therapist.” Whereas in the UK it’s like, “Therapist? What therapist? Whose therapist? I don’t have a therapist. No, I definitely don’t, I’ve never spoken to a therapist.” So in different parts of the world, it’s very different.  


Chapter 9: Create a place to flourish

HOFFMAN: We’re back with Alexi Robichaux — and Prince Harry — of BetterUp! If you’re enjoying this episode and want to share it with friends, send them to That’s A-L-E-X-I. And to hear our full conversation, become a Masters of Scale member at You’ll hear us talk about BetterUp’s quest for angel investors, after striking out with VC firms, including Greylock.

When we last heard from Alexi, he and his co-founder Eddie Medina had discovered the value of their core product — not a moment too soon! They’d tapped into an eager consumer base, and had direct conversations with their users. Most importantly, they had developed a more flexible and responsive mindset, which allowed them to make bold bets and take more daring leaps.

And here’s what they were building towards.

Alexi and Eddie saw BetterUp as no less than a human transformation company. They wanted to provide individuals not just with therapy, but with professional coaching informed by therapy’s best practices. In other words, the kind of coaching support Alexi had craved in his time of crisis.

ROBICHAUX: It started with myself, and I didn’t fit a model. The world as understood by the average person was black and white. It was like, “Do you go to therapy or do you not go to therapy?” And I went to therapy, and they were like, “You can be here. A general physician can create a fitness plan. I don’t know why you’d ask them to do that when there’s fitness trainers, but they can, they’re qualified to. A therapist can coach you.” But it was pretty clear I didn’t have a clinical diagnosis. I was dissatisfied with the binaryness of it. It’s like, well, what do I do then? I’m sometimes depressed, but I don’t have clinical depression.

And there wasn’t a place for me. There wasn’t a place, I would say, at an intervention level. The only intervention most people know of is something’s wrong up here, I go to therapy. But what if something’s not quite that wrong up there? And that actually, in its most basic sense, was the first aspiration of BetterUp. 

HOFFMAN: Alexi’s own experience was reflected back to him in BetterUp’s early users. And he and Eddie started to identify a market gap the size of a canyon. 

ROBICHAUX: What about everyone else who doesn’t have a clinical diagnosis, who can’t afford executive coaching because they’re not Sheryl Sandberg, they’re not these Bill Gates, they’re not these famous executives who have benefited from coaching, what do we do?

And the answer was, I would say the actual real behavioral answer is a lot of people go to therapy, and they get generalized anxiety diagnoses so they can stay there and bill it through insurance, but that didn’t feel like the right answer.

So that’s what we tried to create. This model that covers things from you may be languishing, but how do I actually get you to flourishing?

Chapter 10: Prioritize your users’ trust

HOFFMAN: Alexi and Eddie saw their customers were hungry for the answer to this question. When you’re running sprint after sprint, it’s easy to notice stress, or anxiety. But it’s harder to pick up on what might be missing. Like work-life balance, or even a sense of deep purpose. 

So to help their customers develop a mindset for flourishing, BetterUp started adding support systems.

ROBICHAUX: When we first started, you actually got two coaches. One was a therapist, like my friend, Michelle, who was coaching on mental fitness, and one was an executive coach, coaching on professional development. And the whole benefit of BetterUp was both sides.

Initially, I wanted to call the company Entourage because the whole idea was you all need an entourage of coaches. You need a professional coach. You need a sleep coach. You need a nutrition coach. You’re all rock stars, you deserve to have your team. 

HOFFMAN: But selling to individuals, it was tricky to make the economics of this method work. At one point, for pure resource allocation reasons, they had to scale down from two coaches to one. It was a painful step backward, away from the “entourage” mindset they were trying to cultivate.

But then, came another unexpected pivot, again prompted by BetterUp’s users. It starts with a promise Alexi had made when recruiting his chief technology officer Ryan Sonnek.

ROBICHAUX: So Ryan and I had been at VMware, enterprise of all enterprise. Ryan famously joined BetterUp on two conditions as our CTO. One, we would never sell to the enterprise. And two, he would never have to manage people. 

HOFFMAN: As CTO, Ryan was already managing people. But on the enterprise point, Alexi had kept his word. 

ROBICHAUX: I was like, “Ryan, why would we ever sell to enterprises?” They’re going to want the data, they’re going to spy on their employees. This is going to break — what I had learned from Disney is this concept of the experience economy, which is transformational experiences. And safety and trust are the bedrock of that.

And so we just thought we assumed a priori, like, you can’t have that in the enterprise. They won’t allow it. 

Chapter 11: Be curious instead of self-critical

HOFFMAN: If you didn’t quite follow, Alexi and his team knew their product would break, if they broke their user’s trust. So they avoided designing a BetterUp product for enterprise. They’d learned the hard way not to prioritize a spreadsheet over the core user experience.

But then they learned something fascinating about how people were actually using their product. 

ROBICHAUX: We started to learn from our users this weird behavior where people would be like, “Hey, I’m going out to my car at lunch to do these coaching sessions.” And we’d be like, “Why? That’s really odd. Why don’t you just book a conference room?” And it’s like, “Well…” We’d hear things like, “I feel like I’m cheating.” It’s like, “Talk to us about it.”

It’s like, “Yeah, I’m the only person on my team who has this supercharged coach,” and, “I don’t want my manager to think I’m cheating or that I can’t do the job without the coach.” So I often joke that we’re the only company I know who went to the enterprise because it was a better user experience.

So meanwhile, in the back of my head, my now wife who worked at HR at Dell, had always been like, “Why don’t you guys just sell to companies? We’d all buy this in HR. This is awesome.” And we were like, “Nah, nah, nah, they won’t do it.” So to do it with integrity, we basically made a list of like, “Let’s be scientific about this. Why don’t we want to go to the enterprise? List out the things that would have to be true for us with integrity to go to the enterprise.” 

And then we just tried. We’re like, “Let’s see if we can go pitch 10 companies.” And those early companies were things like Deloitte, Facebook, they were gobbling this up, and they were like, “We don’t want that access to the data. We want our employees to change their lives. We want it to feel safe.” And so we realized we just had assumed a bunch of wrongheaded ideas. And when we actually went and talked to another set of users, the enterprise buyer, it was simpatico. Now it’s free for employees. How cool is that? They don’t even have to pay anymore. So it truly created a better unit of value for the end user, but also a unit of value for the enterprise. It was really powerful.

HOFFMAN: Notice how easily Alexi says those critical words.

ROBICHAUX: We realized we just had assumed a bunch of wrongheaded ideas.

HOFFMAN: This realization that they’d essentially built their business backward just rolled off his tongue. Why? Because by this point in BetterUp’s journey, they had all embraced a learning mindset. They had to — it was what kept them afloat every other time they’d been mistaken.  

This is one of the most critical mindsets to adopt along your scale journey. And it’s simply being able to be curious, instead of self-critical, when you’re wrong. As humans, we’re pretty hardwired to have an emotional response to our own mistakes. We get defensive, and often ashamed to boot. 

But the faster you can notice your own mistake and say, “Yep, my hypothesis was totally incorrect here,” the more time you give yourself to change course.

Chapter 12: You need to put your own oxygen mask on first, before you can assist others.

Once Alexi and his team saw just how powerful an enterprise version of their software could be, BetterUp unlocked dizzying new levels of scale. Because their business customers soon learned what BetterUp already knew. Employees who learn a healthy growth mindset help make the whole company better. 

ROBICHAUX: It’s hard to inspire when you yourself are not in a centered, focused place. We all know this in our own life. That’s why 25 year old executive Alexi wasn’t a great executive because I was hurting so much. You gotta put your own face mask on.

HOFFMAN: “You need to put your own oxygen mask on first, before you can assist others.” When founders, managers, and leaders are given the keys to mental fitness, they manage their teams in a much healthier way. 

Since unlocking this insight, BetterUp has embarked on several ambitious scale projects.  They’ve invested in a research and development arm called BetterUp Labs. During the pandemic, they started Project Galen, in which they donated free coaching to frontline healthcare workers, and later, to those struggling with the effects of racial injustice.

And, as you heard at the top of the show, they found a very impactful Chief Impact Officer. 

HOFFMAN: Next question, which is a question I’ve never asked before on Masters of Scale: How did Prince Harry get involved? And what’s it like working with a Royal?

ROBICHAUX: Yeah. So on the list of things I never thought I would do in this life, right?

We met him through a mutual friend, and he had told him about BetterUp. He had moved to Los Angeles famously, and he was, I think, looking for ways to give back and, I think, really resonated with our approach, was his approach, that it’s not about therapizing the world.

For most people, what they’re dealing with is normal human life, and they’re going to have these ups and downs. And what they need is resilience. What they need is mental fitness.

Chapter 13: Get on the front foot and be proactive

HOFFMAN: This concept of ‘mental fitness’ as distinct from ‘mental health’ is what drew Prince Harry to the company. We’ll let him tell the story from his perspective. 

PRINCE HARRY: Look, I’ll be honest, I had no idea about BetterUp before I moved to the U.S. 

HOFFMAN: Prince Harry had spent years dedicated to the cause of improving mental health outcomes. But in the UK, in particular, it was sometimes an uphill battle. 

HOFFMAN: As a born and raised Californian myself, we would tell jokes. “Hey, my therapist will talk to your therapist” as a way of building a connection. I’m aware that that is a very Californian perspective.

PRINCE HARRY: You’re absolutely right, Reid, about the cultural differences, they’re immense. You talk about it here in California, “I’ll get my therapist to call your therapist.” Whereas in the UK it’s like, “Therapist? What therapist? Whose therapist? I don’t have a therapist. No, I definitely don’t, I’ve never spoken to a therapist.”

HOFFMAN: But now, he and his family have relocated to Southern California … you may have heard about that.

PRINCE HARRY: Through a few new contacts and a couple of people in the U.S., they made me aware of BetterUp. It was on a Zoom with Eddie and Alexi, and I’d heard their vision. It was like, “Wow, you guys are doing this. And not only are you doing it, you’ve been doing it for a few years, and you’re already at scale. This is really exciting because what we want to be able to do is turn the conversation from mental health, which is so much focused around mental illness, and change the dialogue and change a whole conversation to make it more around mental fitness.” I think that’s really where we’re headed now.

HOFFMAN: That shift in framing was key to Prince Harry’s decision to become BetterUp’s Chief Impact Officer.

PRINCE HARRY: The chief impact officer role for me at BetterUp is 100% about driving advocacy and awareness for mental fitness.

99.9% of people on planet Earth are suffering from some form of loss, trauma, or grief. It doesn’t matter what age you are, but the majority of us have experienced a lot of that in our younger years, therefore we’ve forgotten about it. Now, the body doesn’t forget, the body holds the score as we know. And therefore just as much as there’s a mental health aspect to it, there’s also the emotional aspect to it as well. And I think the more that we can talk about it, the more we understand it. The more we understand it, well, the more we understand each other.

HOFFMAN: Part of what I share with you and the entire BetterUp company is to have a shift in mindset, to realize that this is something that is a universal human condition and is a universal human condition that you can also play, not just to avoid losing but play to win. And improve.

PRINCE HARRY: Yeah. Rather than looking at going, “Yeah, exactly that, every single day I’m trying to survive,” or, “Every single day I’m trying to cope,” I think we need to completely change it. And that’s what I mean about the difference between mental health and mental fitness, is the mental fitness aspect is like, “I’m not going to wait for myself to be, either collapse on the floor or wait to have a nervous breakdown or burnout and then have to fall on my friends or then have to pay X amount of money or find the money to be able to afford professional help.” Mental fitness, as far as I understand it, is more a case of get on the front foot. What can you do to be proactive, to prevent the situation from happening?

Chapter 14: Change your own mindset first

HOFFMAN: Changing cultural attitudes on a global scale demands an impact officer with a global audience. And that’s the goal BetterUp has set for themselves. 

ROBICHAUX: We ended up with the Chief Impact Officer really focused on what we talked about, Reid. I’ve always said, Eddie’s always said, “The biggest thing we have to do has nothing to do with our business. Our business is rate limited and bound by this cultural concept of mental health.” If you’re LinkedIn or Google, the internet is the right limiter on your business. You need more people to have the internet. Well, what’s the internet for BetterUp? More people realizing that mental health is not an on or off switch, but it’s a spectrum. And so that is where that role is pointed.

HOFFMAN: BetterUp’s goal is to change everyone’s mindset around mental well-being. But before you can change the world’s mindset, you have to change your own.

I’m Reid Hoffman. Thank you for listening.

Masters of Scale’s mission is to democratize entrepreneurship. Launched in 2017 as a weekly podcast featuring Reid Hoffman, we’re now two weekly podcasts — Masters of Scale with Reid Hoffman, and Masters of Scale: Rapid Response, hosted by Bob Safian — as well as an award-winning daily learning app, a best-selling book, virtual and live events, and more, serving a global community of founders, funders, and leaders looking to innovate at scale.
Sign up for our weekly newsletter