Timestamped Overview

00:00 Joining eBay transformed my leadership approach entirely.

04:32 Relationships significantly shaped my career trajectory.

08:36 Focus on purpose, not outcome, for impactful leadership.

14:14 Joined StockX, aligned with founders’ original vision.

19:04 Continuous personal development and effective leadership focus.

21:22 Last five years challenging, unique, yet constructive.

25:10 Mountains symbolize challenge, motivation, and perspective cycles.

31:16 Early paper route instilled lifelong purpose and responsibility.

34:50 “Free” bracelet inspired personal and professional transformation.

38:12 Annapurna: Adventure, sacrifice, and summiting life’s challenges.

39:39 Succession planning and embracing new opportunities.

44:12 Choose to be a sail, not cork.

 

Full Transcript

Darren [00:00:02]:

Hi, everyone. Welcome back to one of one. I’m your host, Darren Gold. My guest today is Scott Cutler. Scott began his career as a lawyer and investment banker, was a senior executive at the New York Stock Exchange, president of Stubhub, head of Americas for eBay, and now CEO of Stockx. In our conversation, we talk about the importance of genuine relationship and leading. We discussed the incredible complexity of being a CEO over the last five years and Scott’s practices for sustaining focus and energy, including the importance of physical conditioning, Scott’s unique perspective on time management, the importance of having a morning ritual, and his use of the mountains and the summit in particular as a guiding metaphor in his life and his leadership. Please enjoy my wonderful conversation with Scott Cutler. Scott, it’s so great to have you here. I’m so excited to be in this conversation with you. Thanks for being here.

 

Scott Cutler [00:01:06]:

It’s going to be incredible. I’m looking forward to this one.

 

Darren [00:01:08]:

There’s so many places we could start this, and I thought maybe the best place to start was the first time I met you. And if my memory serves me, it was June of 2015. It may have been the very first day on your new job as CEO of Stubhub. Oh, yes, right. It was at the eBay senior team offsite, three day off site. EBay had just spun off PayPal, and of course, eBay at the time owned Stubhub. And I think it was your first day on the job. And I noticed there were a lot of things I noticed about you, but there were two that really stood out that I thought I’d just bring into the conversation. And maybe we’ll take that and pull on those threads. The first thing is, you were clearly wearing the coolest sneakers in the room, if I remember correctly. And the second is the degree of interest and engagement in the topics we were talking about, the topics of leadership and how you build an extraordinary leadership team. And then, of course, that led to a relationship where we’ve gotten to know each other a lot better. So I thought we might just start at that point and maybe from that point, look a little backwards and bring our audience into your trajectory. What brought you to that point? Your first, really CEO role at the time, and then we can sort of point forward from there.

 

Scott Cutler [00:02:25]:

Yeah. Wow. I totally forgot. But, yeah, I mean, that was. Boy, what a moment in time, joining eBay. I was obviously joining as the president of Stubhub, but was part of the eBay leadership team at that time. And that was my first opportunity to be a CEO. And I was coming from an environment where I had spent the last nine years at the New York Stock Exchange, and I’m sure we can talk about that. That was really my formative opportunity to be a leader. I was there for nine years. It was an incredible journey for me, for our company, for the markets overall. But when I was leaving that opportunity and going back to the west coast, which for me was home, because I had, I was really raised on the west coast, in Seattle, born in California. All of my career had really been in technology prior to being in New York. But I really, to that point, was largely more of a transactional type of leader. I mean, I was in transactions. I mean, it was winning business as an investment banker, I was prosecuting transactions as a lawyer at the New York Stock Exchange. You’re on Wall street, and here, going back to California as a CEO, really having to show up as a different type of individual, as a different type of leader, not the Wall street leader, but a more compassionate, more empathetic, more in touch leader, and thrust into that environment as a CEO. And so it really started to challenge my perspective of what did I want to be like as a CEO, and what are the things that I was going to need to change about myself, about my leadership style, about my leadership principles at a time of rebirth and recreation at eBay, as a marketplace, it was, we called it day one. It was day one of a new eBay that was split up. But what I remember the most is just the realization that I was going to have to be a different leader.

 

Darren [00:04:26]:

Yeah. And different in what sense? What did you discover about yourself? Or what did you already know that needed to change?

 

Scott Cutler [00:04:32]:

I think when I think about some of the things that I’ve been challenged to grow as a leader, one of them has really been on the relationship side. Now, on the one hand, and maybe we’ll talk about this, a thread through my entire career has really been the ability to maintain, develop, extend, build relationships with the people that I’ve worked with. And so if you look at the six different chapters of my career, I still maintain and have relationships with a lot of, if not most of the people that I’ve worked with in all of those different chapters. And every chapter, new chapter was opened up. And this is true of every single one was opened up through a previous relationship that I had developed and fostered and built. And it led to something further down the road that I would have never known of. A door opening. Stubhub the door opening actually happened. Maybe it was a year or two before that, and then the CEO of eBay that I worked with, Devin Wenig. Before Devin had joined eBay, he was actually at Thompson, Reuters and at the NYSE. They were one of our biggest clients. And so he was not only the president of that, but he was also overseeing the relationship with the NYC. And I developed a relationship with Devin. I never would have thought that ultimately at one point in time it would lead to a completely different trajectory in my career, but in fact it did because of a relationship that was built in a different context in a different time. And then probably somewhat serendipitously, a door opened and I’m going through a door, but probably with somebody that I had already known before.

 

Darren [00:06:22]:

Yeah. So I was getting a sense, though that there was something about relationships, that there was an extra, extra gear to those relationships that you might have discovered.

 

Scott Cutler [00:06:30]:

Yeah. Thanks for the prompt. So, again, while investing in those relationships was always part of who I was being in relationship. And maybe this is the thing, being in relationship with the people that I worked with was and has become a philosophy that now I’ve embraced in now multiple different instances. And the being in relationship, and learned a lot from tream in this regard, but is a clear understanding of myself where I need to develop personally, really having empathy for the other person in the relationship, and then a shared context of where we are and that the center of that is really being in relationship. And so opening that up for my leadership teams has really been one of the practices to do that has really been as part of our leadership team meetings, weekly check ins, where we’re checking on what’s going on in our personal lives. It was really a way to unlock that being in relationship or being in empathy with the people that I’ve worked around. And it was a practice that I had never experienced before that, before that time. And what it really allowed for me is just to understand much deeper the people that I was working with in a different context. And it’s not like that wasn’t. It was ignored before, but it was just intentionally cracked open as a way to more efficiently operate in a shared context, to say, we know each other, we trust each other, and let’s move faster together because we know the circumstances in which were operating at that moment. I guess being in relationship was the thing that was shifting for me.

 

Darren [00:08:13]:

Yeah. So you’re at Stubhub. This is your first essentially CEO role. One of the things that I think has been a pattern when you’ve come new into companies is you’ve seen a high point of leverage, a change that could be made that only maybe somebody with an outside perspective can see. I think that might have happened at the New York Stock Exchange, happened at Stubhub. Can you talk a little bit about that if I’m getting it right?

 

Scott Cutler [00:08:36]:

Yeah, I think there’s so many books that are well written around 30, 60, 90 days. But one of the, I think the most important things early on in leadership is to be able to have an impactful change or an impactful perspective that you can put into practice right away after you’ve had a chance to absorb and to listen. And at Stubhub, it was largely just a change in the way that prices were displayed to consumers. And it was more of an observation that I had at that point in time, because Stubhub, and probably everybody knows what it is, but it’s a marketplace. But the sellers on that marketplace list their tickets on multiple different channels or different platforms. The winning platform, typically for the consumer, is the one that at the right time, is at the lowest price. And that was how the New York Stock Exchange operated. By definition, price time priority in terms of how orders are matched in the market. And so I knew that technologically and how the markets operated. But coming into a new marketplace at this observation about the importance of pricing and timing for transactions like that in competitive environments. And so it was a change that was very obvious to me, but it was also a philosophy that was part of a marketing campaign at the time. It was part of a cultural philosophy at Stubhub. And so part of that had to be broken apart, culturally, broken apart with a team. And it required for me, daily stand ups with key leaders to implement this change. Now. It had a tremendous impact on the business. He was the second learning. It had tremendous impact on the financial results for the company. But I quickly learned that while those financial outcomes were great, there was an aspect of how it was done that people didnt necessarily feel or leaders didnt necessarily feel, that it was an empowered way of getting to the decision. Now, it ultimately is probably the right decision, but the how to get there in terms of empowering and then realizing that for most people in a company, financial results don’t really matter. It’s the why you’re doing something that matters even more. And afterwards, I kept on saying, wow, look at all this great success that we’ve accomplished. And people are like, yeah, it doesn’t matter to me. And so that really led me more down the path of, how do you open up culture? The why, what is the purpose of what you’re doing? Connecting that to the business outcome is a much more powerful leadership approach than focused on the outcome itself. It’s the input that drives the output. Another learning, kind of going through that as a first time CEO.

 

Darren [00:11:33]:

Yeah, great learning. I imagine it’s repeated itself in the last eight or nine years. Exactly. But I’m really curious about this phenomenon of fresh perspective. Gordon Moore and Andy Grove had this famous story when they first decided to exit the memory business. They said, what would a new CEO do if they came in and we got fired? And the lore is that they walked out of the building, came back in and made the courageous decision at the time. Courageous decision. Now, quite obvious in retrospect, to exit the memory business. You’ve done that. The New York Stock Exchange, you’ve done that at Stubhub, I imagine when you came to Stockx, which we’ll get to in a moment, and it’s easier to do in those first few months, how do you sustain that sort of fresh, disruptive, kind of innovative, courageous thinking year, two years, three years into the business?

 

Scott Cutler [00:12:24]:

I think it’s harder the longer that you’ve been anywhere, to be truthful. And I do think that this is probably why CEO’s turn over every four or five years. And I don’t know is if that’s the timeframe, so to speak. I guess what allows a new leader to come in with a fresh perspective is they’re not burdened down by the way of doing or that’s how we do it, so therefore it can’t be changed. You’ve got no emotional tie to either the strategy or the decisions that led you there. And so you’re able to be fresh in your perspectives coming in. And so to me, probably the unlock is one can’t be set in their ways nor their strategies. And so being able to step back and really be clear, what are those things or those philosophies that are holding you back? That could be constraints for the next layer of growth and getting into a mindset or in a place and a safe place to be able to challenge the status quo. And I think that is something that is probably a great practice as a leader to stay freshen because you can very easily get caught in the trap of, hey, we’ve had success and we’ve had success doing it this way, and then get quickly trapped into, oh, that is the only way.

 

Darren [00:13:48]:

Yeah, well, maybe we can use that as the segue, because I think you’re right at that mark. Now, five year mark as CEO of Stockx, if I’m correct, and I’m curious to hear how you got to that role. And in many ways, as I know, sort of like it was tailor made for you. So I’d love to hear also just the combination of experiences that made you the natural choice for really leading that company at scale.

 

Scott Cutler [00:14:14]:

So I’ve told this story so many times, but I was obviously not the founder of Stockx. We’ve had incredible founders of Stockx who had a big vision, and part of that early vision was so married to my background, which was they were going to create a new commerce marketplace based on the principles of the New York Stock Exchange, Stubhub and eBay. Not so famously, but I reached out to Josh Luber, who was the then CEO of Stockx, and literally on day one and said, there’s one person in the world who knows what you’re talking about. That was really the serendipitous moment that led me to Stockex. And so I had now a perspective across multiple marketplaces, and lots of different elements of those marketplaces were pulled together uniquely into the model of what Stockx has ultimately become. Kind of like the New York Stock Exchange having a bid ask real time marketplace, kind of like Stubhub in terms of the organization, the structure of the marketplace, seeking to have partners in the industry, kind of like eBay in terms of connecting buyers and sellers on a platform, but in a very particular vertical market. And so I was uniquely positioned to have that perspective at the time. And I will say five years, five and a half years into the journey, what I really try to go back to, and it really was the purpose, another purpose of me joining Stockx was I really came in with not only the commitment, but the desire to really partner with the founders and ultimately develop, mentor, and hopefully my successor is the founder of one of the founders of Stockx. But to be able to go on a leadership journey with them, where I still feel as though, while I may have way more time and experience as being a CEO, I still feel like I’m really going back to the original vision of the founders of the company, that ethos of what it means to be a founder, and coming back to that as a true north for me to remind me as to what the purpose is. And that, I think, is a very big difference between a professional manager CEO and a founder, where the founder created that vision out of nothing. And there’s an incredible power that’s associated with that creation that I think founders can uniquely have. And so for me, it’s actually been, I’ve gone back to that anchor a lot with. With Greg Schwartz, who’s a president coo of Stockx. And we constantly kind of go back to that, to sit there and say, what is it about that original vision that we still have yet to accomplish? And I still think we still feel like there’s a lot more to go.

 

Darren [00:17:05]:

Yeah, it’s maybe no surprise we’re in this conversation. Paul Graham just penned the essay founder mode. It’s getting a lot of circulation, and it’s both the creative act of bringing something to life that a founder uniquely brings to the role, but also the energy of a founder. And there is a big debate going on, is, can that energy be replicated by what I would call more of a professional CEO? And what I’m hearing you say is that you’re, and maybe I’m putting words in your mouth, trying to integrate the very best of somebody that has the wisdom and experience with also the grounding in what the original vision was in the energy of Vander.

 

Scott Cutler [00:17:40]:

Yeah, what I would say, also say, I probably generally agree with that, although I guess what I would add to it, and I think about my own journey at Stockx. I was kind of there from the beginning in the sense that I had worked with the founders in kind of a quasi advisory relationship, and so I knew the journey from the very beginning. And so by the time that I had joined, there was so much connective tissue to that original story that it wasn’t brought in completely new. And at the same time, I look at even Stubhub when I joined, that was 17 years into its existence as a company, and yet there was still a whole new opportunity to unlock. But lo and behold, who owns StubHub now? One of the founders of Stubhub, who left when it was acquired by eBay, started another company, and then ultimately has brought it back together again, full circle. Super interesting story, I’m sure.

 

Darren [00:18:40]:

Yeah. Yeah, for sure. I want to get back to this question of your leadership, because I know you’ve been very intentional about crafting the kind of leader that you are, and I imagine you had a vision for what that might have looked like when you were taking the job first at StubHub. Bring us into your leadership philosophy or philosophies, and what’s unique about it. And where are you in that journey?

 

Scott Cutler [00:19:04]:

Well, I would hope that I’m on a continuum of that journey, which is a couple principles that I think are really important as leaders. One, going back to that principle of being in relationship, it really is, number one, first and foremost, a commitment to personal development. Which is you’re a CEO in development, always, always learning, always having to change, always having to evolve. And I think the thing that I brought in to myself, but also in the leadership circle, so to speak, is being able to show up with a greater level of vulnerability. And vulnerability and personal development are really go hand in hand, which is vulnerability, saying there is opportunity for me to improve, there’s opportunity for me to change, and then how do I actually be intentional and overt to say, hey, here are the things that I’m working on? And so personal development has been a key part, key pillar of what I believe is the leadership philosophy that I believe in so much. The second pillar has really been a commitment to being a great leader. Now being a great leader means that you can attract, you can retain, you can get great performance out of the people that you work with. And being great leader is not just a only contributor. You’ve got to be able to get people to take the hill with you, to follow you into challenging, uncertain, volatile times in a way that’s inspiring. Obviously, we can’t force people to do things. You have to lead people. And so being a great leader and what that means is something that I’m also focused on personally, but also with my leadership team and what I expect of the leaders that I work with. And the third is really producing results. And I think that’s really probably sometimes one of the more challenging aspects because we have lots of things that we don’t necessarily control about those results. We have macro environments, things that change. And yet, as a CEO, you really, there isn’t always an expectation that you are moving the company forward. So those, I think, are the three pillars that I am constantly working on as a leader and with my leadership team.

 

Darren [00:21:18]:

Where are you right now? What’s the thing you’re working on?

 

Scott Cutler [00:21:22]:

Oh, yeah. So I’d say it’s number three. We are in a very unique time. I feel as though it’s the most unique time in my career. I was at a dinner the other night in Silicon Valley with a bunch of investors and a couple of other CEO’s, research analysts. And I was sort of describing what I’ve seen in this consumer environment over the last five years. And it started with a pandemic that we had never gone through. It was fueled by a one time $10 trillion global stimulus that came into the global economy. That stimulus created inflation, created interest rates, created policies to then counteract that. And the pullback of a one time event into the marketplace created a couple of different things that now, I’ve learned a lot from which is one, people misread what that stimulus was for the world, misread it as an increase in demand or a shift in consumer behavior. And in fact, it was just a one time event. And now past it, we’re also making the same mistake as we’re comparing ourselves to the level of also a one time thing that came into the market, a level that we shouldn’t necessarily compare ourselves against. And so I think now with the benefit of time, it’s like, how do you work through that and then introduce into that as the CEO all of the social unrest, the global unrest, the political unrest, the requirement that you as a CEO show up in a very different way than you have before. Combine all of these elements and I really think, like the last five years have just been incredibly challenging to be a really successful CEO because of the tensions that you feel personally, the tensions that you feel for your people, the environment that you know that everybody is operating through, the real challenges that you have to stand up in front of the group and make sure you’re saying the right thing or not the wrong thing, and then how to produce results in the middle of that. It’s not just about the results, but you have to lead a company successfully through that environment. And so maybe we’re at the tail end of that, which I believe. But I think what I’m still trying to create my own narrative, like what has it been like for me as the last five years, personally give myself a chance to really understand how has this impacted me as a leader of these volatile, uncertain times and what do I want to take from that? That’s probably where I’m at right now is very reflective of where those last five years have been. Knowing that, I think we’re coming into environment, hey, we’re here today. Interest rates have come down for the first time in two years. This is probably a diff. We’re at a different part of the journey and different part of the innings in the game. I think it’s probably constructively more positive than it’s been in the last five years.

 

Darren [00:24:14]:

Yeah, hopefully today marks the point in time where we experience a different five years going forward. But I’m sure they’re going to be challenging, but in their own unique ways. And frankly, it’s the reason I started this podcast was, I do agree with you. The last five years have really tested CEO’s in their role. It is a unique role with incredible responsibility, enormous complexity, and I think it goes back to the three things that your most focus on personal development, becoming a great leader, and actually getting results. Those three things in combination have to be true. You’re no stranger to hardship and challenge. You’ve put yourself in challenging situations. You’re an extremist when it comes to sports and endurance and things like that. So I’m curious just to get that aspect of Scott revealed here and how that’s helped you over the last five years and what advice you’d give other leaders, other CEO’s when it comes to building the habits of endurance.

 

Scott Cutler [00:25:10]:

Yeah, so I think, as I think about this question, yeah, I do push myself. I push myself largely in the mountains. The mountains have been a source of inspiration, a source of challenge for me. I’ve told lots of different harrowing stories about surviving circumstances in the mountains. But in particular, I think it’s the summit that’s maybe the most important. And there’s a great quote, and I have it really memorized, but this is the quote, and I’ll pull from it, is that you cannot stay on the summit forever. You have to come down again. So why bother in the first place? Just this, and this is the important part of this quote. What is above knows what is below, but what is below does not know what is above. One climbs, one sees, one descends, one sees no longer, but one has seen. There is an art of conducting oneself in the lower regions by the memory of what one saw higher up. When one can no longer see, one can at least still know. And so when I think about what that means for me is that, yes, there have been moments of time where I’ve been on the summit or I’ve accomplished something, and it’s momentary. I mean, it lasts for just a nanosecond. Hey, you’ve accomplished it. The other side of that is typically a descent, but when you’ve climbed, you’ve actually seen what that was like. You remember that, and you remember it when you’re in the fog and when the trail is lost, but you have that memory of what it takes, when you could have much greater perspective. But you’re pushing again for that next summit. That philosophy of climbing summits, descending, knowing there’s another summit, is just, to me, that’s the cycle of the challenge that I put myself in physically, but also, I think, mentally as a CEO, to put myself constantly in that challenge of, hey, reaching that place, descending, and then going after it again. And to me, that’s highly motivating by what the challenge of what all of that represents symbolically, but also what I know what it takes in the heart, the lungs, the legs, the mind. To be able to do that.

 

Darren [00:27:33]:

Incredible. What an incredible quote. I’m gonna have to get that from you. What about on a more daily basis, do you have any daily rituals that you practice that are instrumental to who you are as a leader?

 

Scott Cutler [00:27:45]:

Yeah. So, I mean, again, in the same theme, I pretty much only run global businesses, and as a result, I’ve spent a lot of time on planes. I’ve spent a lot of time in different time zones. It’s very challenging and taxing physically, mentally, on the body. And so pretty much wherever I am in the morning, I am pushing myself physically. And I think it’s creating both the space for me to think because I also use that time to reset and to rethink. But it’s also preparing me physically for what it’s going to take to operate in really long day, typically long meetings, and then be able to go again. And to me, the power of this was not so recent. It was last quarter, but I really wanted to see our team in India. I had not been there before. I had been on the road for 15 weeks leading up to that trip, and I was going to go to India from Dubai, fly in at 01:00 meet at 01:00 a.m. stay all day, meet with the team for 12 hours of reviews, and then go back. And midway through that day, somebody asked me, like, how is it possible that you’re able to stay connected in this meeting? And I just said, I’ve trained for this day. I’ve trained for this moment, but be able to be dialed in in that moment for 12 hours, being tired mentally, physically. I don’t think I could do that if I really didn’t. Don’t spend time mentally and physically every day challenging myself in that way, because it’s a very taxing position, emotionally and physically, mentally, in the CEO position, I.

 

Darren [00:29:29]:

Want to ask a tactical question around that, because the response I typically get for those that want to invest in their physical vitality is, I just don’t have enough time. How do you, and I know the same is true for you. That excuse is ready for you to use. How do you prioritize? How do you create time?

 

Scott Cutler [00:29:46]:

We all have as much time as one another. We all make different choices with what we’re going to do with that time. And so it’s simply a matter of choice. But I will say, for me, that choice comes with a sacrifice. And to me, it’s now really no longer a sacrifice. It’s almost always been part of my life. But I think if I didn’t have that morning sequence, the morning, and this is typically a time where nobody else is up, nobody else is there to disturb me, that’s my time. If I said to myself, hey, midday is going to be the time that I’m going to go work out, no, never. It would not be possible. At the end of the day. Couldn’t be possible. But for me, that first choice of what I’m going to do when I’m going to wake up is my choice to make. That’s the only space that I’ve found, at least for me, where at least I have the least number of distractions at that moment in time. That’s a time that I can choose where I want to spend it. Whether that’s through meditation or prayer or physical activity or getting centered, that is my time.

 

Darren [00:30:52]:

I want to rewind the clock, maybe all the way back to young Scott. And as you know, I’m a big believer in our own self mastery and understanding where we came from and really understanding how our formative experience has shaped us. I’m curious to know who the young Scott was, how you were shaped, and what has been the implications for you as you lead your life, as you lead others.

 

Scott Cutler [00:31:16]:

I was with my brother this last weekend, and he’s a head neck surgeon, I mean, effectively a neurosurgeon. And we were asking ourselves this question, and I look up to my brother a lot, but, you know, I think both of us actually, when we were young, we had paper routes and we had to get up early in the morning. We had purpose, we had to be up early in the morning. And maybe that was like a farmer growing up on the farm and having to milk the cows, but we had responsibility every day to deliver the paper. It’s unfortunate, that’s probably not part of very many youth experiences today, but there wasn’t, even on a holiday, there wasn’t that opportunity to say, I’m going to take this day off. It was every single day. And I think the power of that one thing early in my life, and that was I had that paper out from, I don’t know, it was like second or third, maybe not fourth grade through as a senior in high school. So a long period of time, it was just then the rest of my life, I’ve been a morning person and a person with incredible purpose. When I wake up or responsibility, there’s a blessing and curse associated with that, and the blessing has been that ability to fight through it. But also, I don’t know, when I just don’t sleep in, I’m up and ready to go without an alarm pretty much every day. So I have that. Hold on a second. What am I missing out on if I’m not awake early?

 

Darren [00:32:44]:

Yeah, you mentioned your brother, and there was a spark that I saw in your eyes when you said that. And I know how important family is to you and has been to you. I’m wondering if you could just comment on that aspect of your life, because as CEO’s, we are not only managing and leading the businesses, we’re playing a part in leading our families and our communities and just expand the circle of concern a little bit and bring us into that part of you.

 

Scott Cutler [00:33:07]:

Yeah. So my parents, incredible, incredible parents. Great examples to me. Six kids, so not easy, certainly probably being parents of six kids, three boys, three girls. We were a rowdy bunch, I would say, but a really close unit. A lot of inspiration from my mom and my dad in different ways. My dad, in one respect, followed his dad, which was, he was just incredibly dedicated to his work. And so my dad wanted to actually have a lot greater connection with the family, do great activities. And so part of being in the mountains and the outdoors, I would just give credit to my dad of wanting to really create great connections with his kids. And then my mom was more a quiet, soft lady, but with very high expectations. And those expectations were such that the Ralph Waldo Emerson quote about persistence was on our refrigerator. A little magnet on the refrigerator, just a reminder every single day to persist in the things that you’re doing, and which is also a quote that stayed with me for my entire life. And so I think my parents definitely shaped who I ultimately would become, but probably the things that were then probably important pillars for me as a father, as a dad, as a human being.

 

Darren [00:34:33]:

What’s changed about you most?

 

Scott Cutler [00:34:36]:

Oh, boy. From when to when?

 

Darren [00:34:41]:

Let’s say your early adult years, when you thought you knew everything and life was going to go on forever and to where you are today. The last, call it a couple of decades.

 

Scott Cutler [00:34:50]:

Well, I mean, I think there was a particularly significant point in my life, actually. It was between eBay and Stockx, actually. And I was at a dinner down in LA hosted by Keith Farazzi, who wrote this book, never eat alone. And they had a guest there that was hand stamping bracelets with one word on it. And that one word was supposed to be your motivation. And the word that I chose was free. And so it was put on a bracelet for me that following weekend, someone very close to me took his own life, and it just rocked me still. I still think about it all of the time, but that notion of being free at that moment of time, I looked at that bracelet and it led to just some incredible changes for me personally and professionally that ended up opening door for stockx. At that time, I also took a board position with Brookfield, which has also been a really interesting part of my career. The work that I’ve done in suicide prevention took on a more personal meaning, which has been something that I’ve been involved with for now over 15 years. Led to a couple of years ago, my involvement in work around with vibrant emotional health, a nonprofit focused on suicide prevention, but the National Suicide Prevention Hotline. But that moment shook me and required me to think about what I needed to do to be more free to make the right choices, free in making a different set of decisions, a different set of priorities. And so that was, that was a very significant event in my more near adult life. And then the last six years.

 

Darren [00:36:33]:

Yeah. Was it the recognition of the fragility of life that really caused that? Or what was it about this tragedy?

 

Scott Cutler [00:36:39]:

It was that the importance of being in relationship with those closest around you, choosing to spend your time in pursuits that are positive and uplifting. Change your circumstances. If you don’t like what you’re currently in. Whole host of perspectives that when you have that perspective of you are free to choose, the circumstances that you’re in can change with a simple choice. Is that freedom to choose aspect that was really powerful for me at that moment in time. That led to more changes in my career. Now, I’ve changed a lot in my career. I’ve had multiple different careers, so I’ve never been afraid to make the choice. But at that point in time, it was a really significant set of choices and changes that I was about to make.

 

Darren [00:37:30]:

If you were to be given another bracelet today, six years later, what word would it have on it?

 

Scott Cutler [00:37:36]:

Come back to me on that one. Let me steal on that one for a minute.

 

Darren [00:37:39]:

Okay.

 

Scott Cutler [00:37:39]:

I had to think when I was originally posed that question, I spent like a half hour thinking of it. Come back to me. I don’t know what it would be. I’ll think about that.

 

Darren [00:37:50]:

If you come up with something, we’ll share it. We’ll do it afterwards. I know you’re a reader. Books, I know everybody’s usually interested in books, can have the power to change worldviews and reshape thinking and catalyze new ways of leading. Has there been a book that’s been instrumental to you, whether it’s in your role as CEO or in your life in general.

 

Scott Cutler [00:38:12]:

My favorite book, and I’ve read it multiple times, it was written by Maurice Herzog, and it’s called Annapurna. And it’s the first successful attempt of climbing Annapurna, a mountain that they knew existed but didn’t know where it was. And three quarters of the book was their search just to find the mountain before they could even climb it. And the chapters on climbing the mountain were relatively short. And the most interesting part of the book was after the mountain and all that they suffered as a result of throwing themselves, their lives at that quest. And there’s another great quote at the end of that book to the climber that really couldn’t climb anymore because of the injuries that he suffered. But it was essentially, are you going to climb Annapurna again? And the answer was, there are many annapurnas in the lives of men, which, again, probably the same symbol of the summits in our lives, the mountains in our lives, the different challenges that we likely are going to be faced with as individuals or as leaders.

 

Darren [00:39:22]:

This is a tough question, so you can answer it at any elevation, no pun intended, but what’s the next Annapurna for you? And it doesn’t have to be specific, but as you think about this next five years in your life, in your role as CEO, what shows up for you in that question?

 

Scott Cutler [00:39:39]:

I think one of the things, and it’s not that it’s always pertinent, but I think one of the most important things that a CEO or responsibilities that a CEO has is to do your best to find your successor. And for me, that started in partnership with founders of Stockx, but really developing succession. And so I’ve spent a lot of time thinking about that, and I’ve spent a lot of time mentoring and partnering and developing those around me. But the idea of succession is always really important because really try to do your best to leave an organization better than when you found it, but also to be able to leave it in good hands. And so there will be a point in time where that torch, that baton will be handed over, and I’ll be a proud moment for me for what I’ve invested in that as a process. But it’s also, wouldn’t it be great as a leader that you had people around you that were focused on your success? And so I’ve tried to do that as a leader. And so whatever’s next, I don’t know. We’ll see what it could be. But I will say, what’s interesting is that I guess I don’t spend as much time thinking about what is going to be that next thing. I actually am more interested on that door that opens. And in every instance it has been a door that’s opened and it’s been very clear to me that I should go through it. And when I think about the power of transitions, and for me, that was lawyer to banker to NYSE to Stubhub to eBay to Stockx, at a certain point in time, a door opened and I was willing to go through it at that point in time and not look back. And that’s just been my journey, and that’s not everybody’s journey, but I’m excited about whatever door might open and what I would choose to go through in that.

 

Darren [00:41:42]:

Yeah, Joseph Jaworski refers to that as a cubic centimeter of chance. And what he’s trying to convey in that is it’s a small and fleeting door that opens or window that opens, and it’s those that are really attuned to those things and have a pattern and sort of repeated history of seeing them and jumping live pretty interesting lives. So I love that you’re sharing that. What incredible advice for listeners out there that oftentimes I think people are stuck on the sort of more linear, tactical what’s next? As opposed to how do I create the conditions where I’m going to notice opportunities that are right for me and be willing to have the courage to take them.

 

Scott Cutler [00:42:21]:

Yeah.

 

Darren [00:42:22]:

Yeah. So I’m curious, as we wrap Scott, this has been an amazing conversation. If there’s anything that we haven’t covered that you’d want to make sure you add or even just a summary or synthesis of some of the things that you have spoken about.

 

Scott Cutler [00:42:37]:

Yeah. Like I said, we’re in super interesting times, and I think what’s required of us right now is maybe greater than what it was before, but at the same time, it allows us to open ourselves up for potentially much more growth than, quite frankly, maybe we could have experienced before. And so I think for me, the theme that I am continuing to take through this, and we’ve certainly had plenty of opportunity to talk about it today, is to be open to that, crack open to that vulnerability and realize that in the most challenging of circumstances or, and of times, comes this incredible learning, this incredible opportunity that probably will only be realized in the retrospective, but it’s certainly happening to us right now. And so kind of giving yourself that moment to be appreciative and recognize that you’re going through it, but that’s okay. And not being so forced to say, what am I learning from that right now? I mean, that learning is going to come, but it’s going to come because I’m open to how it’s impacting me today.

 

Darren [00:43:47]:

Yeah. So I want to return to the bracelet and imagine that you haven’t come up with a word. I’m not going to force you to, of course, but I’m wondering if I could re ask the question and ask you if you could give that bracelet to maybe one of your children or to a young person out there entering the professional world, and you could put one word on it. Now, of course, it’s theirs to choose what word they want to put on, but if you were asked to put a. A word on there, what would you put on it?

 

Scott Cutler [00:44:12]:

You actually just said it. Choose. Someone gave me this analogy sometime before, but we can either be a cork or we can be a sail. A cork floats aimlessly in the ocean at the whims of the waves and the wind, and yet a sail can take that same waves and wind and harness it towards a direction again in the same circumstance. And so I guess when I say choose, choose to be a sail over a cork. But I think it’s really powerful when we realize that we do have that freedom to choose. We have that freedom of choice to be able to make, and that would be the word for sure.

 

Darren [00:44:59]:

This has been a great conversation. So grateful for you and for the time we’ve spent together. Thank you, Scott.

 

Scott Cutler [00:45:06]:

Thanks for your partnership. Darren means a lot to you.

 

Darren [00:45:08]:

Very welcome. You’re very welcome. I really love that conversation. What stood out most for me was Scott’s reminder of how much freedom and choice we have and how we live and lead. I look forward to being with you on the next episode of One of One. And until then, I hope you live and lead with courage, wisdom, and above all, with love.

 

One of One is produced by Erica Gerard and Podkit Productions. Music by John LaSala.