OPERATORS: Alexi Robichaux (BetterUp) on Learning to Fire Yourself as a Founder

by Joseph Bien-Kahn in

When VMware bought Socialcast, an enterprise social networking startup, Alexi Robichaux became the head of product for VMware’s social enterprise division. He was an executive at a cloud computing giant in his mid-20s. From the outside, it seemed like he had it all. But inside, Robichaux was struggling and he burnt out after 20 months. He had some money from the acquisition, so he spent some time on a “spirit quest” of sorts, searching for why it hadn’t worked out and what he really wanted from a career.

In 2013, Robichaux founded BetterUp, a mobile-coaching service meant to impart some of the wisdom he found onto employees and managers who want professional and personal coaching to better succeed in their careers and in their lives. He’d been a part of the rat race that so many fall into, but was fortunate enough to have the chance to get out; his goal with BetterUp was to create a tool for those who don’t have the cushion to take a step away from their careers. He started BetterUp to help employees find purpose and passion at work.

Robichaux is a font of knowledge when it comes to professional growth and mental health, but he’s also an expert on how to transition from founder to manager and back again. He struggled with his first transition, but at BetterUp, he and his co-founder Eduardo Medina created a system all their own. We called Robichaux to learn more about why he started BetterUp and also how he and Medina learned that firing themselves was the key to building their company.

What sparked the idea for BetterUp?

It really came out of my own experience. I had been fortunate enough to actually discover mentorship and leadership coaching through some nonprofit work that I was exposed to when I was in high school. And that really ignited in me the passion to help people realize their potential. I was a coder and so I was working on the website for the organization, and also continuing to just build and code things in my free time. Eventually, I fell in love with this idea of helping people build their lives and build better lives through developing these skills. And so, as I went through my career, I continued to volunteer at the nonprofit coaching and mentoring high school students after school and found my way to tech professionally, in my day job so to speak. The two had always kind of stayed pretty disconnected. It never really occurred to me that I could meaningfully connect the two.

I was fortunate enough to go and do a startup, Socialcast, where we were one of the first generation of enterprise social networking. I was inspired by some of the themes from the other side of my life related to helping people realize their potential and building better cultures and developmental driven organizations, and was fortunate enough to go through an acquisition by VMware. I became a very young executive at VMware. I was 25 or 26, and, essentially, I just burnt myself out. It was an experience of a lifetime, but I only stayed there for right around 18 months. During that time, I got great visibility to the C suites at some of the Fortune 100 companies and learned a ton, but also realized that I hadn't set the right boundaries and wasn't balancing my life in a meaningful way. Essentially, I realized I needed to go somewhere else.

So, I left and had some time, and I went back and was mentoring the students. I kept coming back to this idea of like, wow, they have me helping them through their life’s big moments: their first job interview or a breakup or their essay for college admission or whatever it may be. And with what I was going through, I felt really distraught, I felt like I had failed, I felt really just bummed out and I didn't have anyone to support me other than my friends or I could call my mom or something like that. I kept coming to this idea of like: ‘Who helps me?’ I'm a little older. I have more economic means. But what do I do? Do I go to therapy? Do I go to a life coach? An executive coach? I really didn't know. And so that started me in about a nine-month journey to find help.

I was hurting on the inside and really frustrated and I tried it all, from therapy to life coaching to executive coaching to the Camino de Santiago in Spain to the Landmark Forum in LA to reading literally hundreds of journal articles and scores of books on everything from positive psychology to leadership to work psychology to clinical psych. Eventually, I really fell in love with an approach of coaching people based on evidence-based psychology from things like positive psychology, sports psychology, and neuroscience. That was the seed of the idea of BetterUp. It was like, ‘Wow, had I had this just a few months ago when I was at VMware, I would have had a different outcome, my team would have had a different outcome.’ There had been bad attrition after I left. If I had a better grasp of myself and my ambitions, it would have been better for me, better for my team, and better for the company. It would have been a true win, win, win, win situation. It was kind of like what I'm doing with these kids, but there should be a way we could do this that's more scalable. I don't know that I would want the coaching to be in person as much; virtual would be more accommodating to my lifestyle. And so that was the start and the seeds of the idea of what eventually became BetterUp.

That's fascinating. So much of what people face, especially founders, is the idea that there are just too many plates to keep in the air. Excuse the mixed metaphor, but there is this sense of almost drowning. Was that the feeling you were having at VMware?

Yeah, I think that's right. We live in a hectic world. Obviously, we're in a really hectic moment in history right now and everything's in flux and a lot of people are hurting worldwide. It's easy to lose who you are in it. I know, for me, I had become someone who I really didn't want to be. I had convinced myself that all these things that I don't believe actually matter mattered to me at the time, whether it was a promotion or my career or being on the fast track and being a young hotshot executive. And those weren't really who I was as a person. They're not who most of us are as people; we're all deeper and more profound than that. But to your point, I just kind of lost my way in the flurry of activity in the hyper Silicon Valley and the “success” that I was experiencing. And, at the end of the day, it was deeply exhausting.

I was fortunate enough to have a little money from the acquisition that I could not work and take time and go on a spirit quest and find myself. But most people don't have that, right? That was the inspiration for BetterUp. Most of us are going to have to do this within our normal life, while staying at our real job. We're not going to do it unless we have someone who helps us see that and really leads us back to ourselves and our values and works as a partner to make sure that we're finding ourselves and not betraying ourselves in our work.

What's fascinating to me is that you're coming at this from the mentality and mental health side, but I think a lot of the stuff you're saying resonates with what Hari and Adam talk about with AbstractOps: how do we create a tool that allows founders and early employees to focus on the things that they're actually passionate about? How do you turn the faucet down slightly to create space to think about the things that are important?

Yeah, I think there's a lot of similarity. It's the same mechanism in many ways, right? It's about a value system. What do you prioritize? What do you care about? What are you uniquely good at? I think those happen on an internal level in your own personal professional growth and journey, and that same thing has to happen at an organizational level as a founder. I would actually argue that in some ways the speed at which you do that personally as a founder, especially in the early days, is the rate limiter or the accelerator on the speed to which your organization will do that.

What is a lesson you wish you knew when you were a first-time, early-20s founder that you think could actually have had a tangible effect on your company and your career?

I mean, there's so much. There's so much. [laughs] 

One thing I wish I would have known is there's really no rules. We spend so much of our life being trained to follow the procedure or the rule. Write a five paragraph essay and make sure that the thesis is in the last sentence of the first paragraph. That's a heuristic. That's a rule of thumb. Generally, that will get you a good essay, right? But as a startup, you're actually not interested in "generally"; you're interested in the "exceptional," by definition. And when you're dealing with the exceptional, there are literally no rules. That goes to negotiating term sheets, to how you should organize your company, and on and on. I would say you definitely want to learn from best practices, but our business was so unique early on, we over-emphasized how a traditional enterprise SaaS company was organized. And as much as that may have helped supercharge growth, it stunted growth in other areas. 

So, I think the biggest thing was kind of this gradual awakening, that myself and Eddie, my fantastic co-founder had, which was just: There are no rules. It’s important to state that in a very real sense, the only rules are what’s ethical or legal. We always should do the right thing, but, for example, convention is not a rule and you're in the business of innovation. So you can ask for that; someone's going to be the first founder to ask for that. Or you can change how your company organizes, even if no other company has ever done it that way. If that makes sense for your business, have the courage to do it. 

Obviously, when it comes to the product, you're doing something innovative and new, that's kind of obvious. That's why you're a business. But I think for us, one of the things we learned is the more innovative and new the business is, the more innovative and new your operations need to be. So, when you're starting to talk about operations, you need to have that same innovator's mindset of there's no rules. I'm going to think from first principles. I'm gonna throw a convention out the window when it doesn't make sense. When it does make sense, I'm going to learn from it, not reinvent the wheels. That mindset was huge and it took us a little while to get there.

Look, for some companies and some products the conventional way makes sense: your product's innovative, but your go-to-market's the exact same as Salesforce? So, yeah, just use the Salesforce’s playbook and distribution, and don't spend a lot of energy thinking there. What I find though, is that for many products, especially as more growth is driven by the product itself, you're seeing operations need to become more tied into the value chain itself and become more innovative.

Something that's fascinating to me is diving into the  moment when a founder becomes a boss. Do you remember that moment and what that felt like and any, do you have any helpful tips to navigate in it?

Yeah, it happened pretty early for us, probably a year or so in our journey. I had already been in management — I had already managed teams — so management wasn't new to me as a function. Although, obviously I wasn't the most experienced manager in the world and was still new in my journey as a manager. But for a lot of founders that is the first time they're going to manage and, in fact, for my cofounder, it really was his first formal management role. It is a big transition.

A framing that was really helpful for me was just reminding myself that as a founder, you want to be firing yourself from as much of the role and responsibility as you can. But you have to responsibly fire yourself. So, when you're hiring your team, your job is to empower them and enable them and get them running and humming at lightspeed as fast as possible, so that you can stop doing that function and go focus somewhere else. What Eddie and I did that worked well for us early on is we were really explicit in all the things we were doing as a founder. As the founder, you should be able to list out all the sub-functions you're doing. By being able to catalog that, and even audit ourselves and give the sub-functions names and label them, it was really easier for us to be able to figure out who we need to be hiring when. ‘Okay, so this function you can keep doing for now, Eddie, but, you know, this one we need to fire you from and hire someone else who's a professional or hire someone who's junior and scrappy wants to figure it out.’ 

Just having that nomenclature and that explicit architecture about, ‘What are all the roles you do as a founder?’ is so important, because there are so many roles and most of us never take the time to sit down and just write them out. Take the time to ask: ‘What are the five or six major things I do every day?’ when there’s only two or three people in your company. As you do that, what you're actually doing is creating opportunity for Person Three and Person Four and Person Five and up to Person Whatever Hundred to really have a meaty role in the company, and to feel that they have autonomy and agency to solve a part of the business where you're not looming over them or stepping on their toes. And it all works.

So, that was one big part of the transition that I've heard a few investors and mentors talk about, but I haven't heard publicly as much as you’d expect given how critical it is to threading the needle. And to be clear, I certainly didn't thread the needle perfectly myself.