So, this is your first CEO gig — is it exactly how you imagined?
I struggle a bit to describe what I’m experiencing. I’ve been in the valley a long time. I’ve had some wins and some losses. Not to be Rumsfeldian, but being a CEO is nothing like I imagined and exactly as I’d imagined. The job is way bigger than I anticipated for a couple of reasons. One, we’re a small venture funded startup, so the CEO has to cover multiple areas. For me, right now, it’s literally three jobs in one. Second, in a small flat team, there’s as much coaching as I can handle — you know I love coaching, but there isn’t an hour in a given day where I’m not coaching someone up. And, I know from our shared experience that the emotional swings of startups is intense. But, I didn’t understand the stamina I’d need to develop for this seat. I feel fatigued a lot.
How are you dealing with the fatigue?
Plant-based protein, more-frequent, less-intense exercise and long stretches without alcohol — like weeks or months. I won’t lie, it’s not fun, but that’s the only way to create more stamina on less sleep. I miss steak and red wine. But, losing weight doesn’t suck.
What has been the hardest part so far?
Three things that I think I dismissed a little too casually before joining methinks as the CEO. First, the context shifting in a given day is ridiculous. It’s exhausting. I don’t know if it’s the sleep deprivation or focus required to dive deep wherever decisions need to be made — and, at this stage, it’s nearly every single hour.
Second, I work for everyone. I knew this would be an adjustment, and I knew I would have to adopt a service-oriented mindset even more. But, what I didn’t understand is the delta between a collaborative mindset one needs as a VP and C-level versus the selflessness of a startup CEO gig — particularly the founder-friendly CEO position. I’m not in a situation where I’m replacing a founder or trying to kick-save a business on behalf of investors. This is a situation where the founders and I are friends, former colleagues, and I am trying to help them realize their dream. I’ve got to keep the founders happy, talk them through difficult decisions where outcomes are indefinite. I’m constantly framing for decisions — even the product and technology decisions I’m not necessarily going to make, I’m framing.
Third, the total lack of feedback is hard to interpret. As a CEO, there’s all kinds of power and social dynamics at play that inhibit CEO’s from getting feedback. Looking back on my career, I understand why I have the love and appreciation of guys like Michael Cerda, Jon Niermann, Michael Bayer — I could give them feedback and talk through difficult decisions, discover outcomes and offer critical insights. They loved that someone was helping them get better. And, at other times, I struggled to work with first-time CEOs because they didn’t have the confidence in their own capabilities — they were caught up in perceptions of the position, struggled to get comfortable and let their guard down. For reasons I understand — Korean cultural reasons — it’s hard for many methinks employees to give me feedback, or “think out loud” in a meeting. The best thing that happens in the US office — the time I can get someone to engage in a healthy discussion, entertain different or alternative arguments.
What are your challenges right now?
At a personal level, it’s about volume — the volume of patience and empathy needed is immense. Bad things happen to good people. Just in the last three months, three really talented marketing team members have had to deal with serious personal issues. I’m talking about really serious things. It’s hard not to take on some additional anxiety when you care about those people. Plus, I have two teenagers at home, so I need to have patience and empathy for them too. As a result, when I discover that busted sprinkler head at 11pm, I go all Clark Griswold in Christmas Vacation, you know, when he can’t figure out why the Christmas lights won’t come on. I’m the maniac spewing curse words in their front yard. That’s me sometimes. But, mostly, I’m too exhausted to “Clark.” Instead, I tend to pace around the house, muttering, turning off lights, locking doors, putting caps on tubes of toothpaste — my kids think I’ve totally lost my mind. But, yeah, I have to work on mustering patience, particularly when I’m low on sleep.
At a business level, it’s the usual stuff, figuring out marketing channels, pricing scrutiny, International expansion — being global is a challenge for the moment, these tariffs are wreaking havoc in the currency valuations. We have operations, customers and investment overseas, so our bookings fluctuate in value. That’s something I didn’t expect having to deal with, but it impacts every business in the world when the two largest economies are threatening each other with trade sanctions.
Wow. Okay, let’s get out of that dark place. I saw you hired Kris Jacob, what’s the reunion been like?
You ever see that video where some random guy describes how Navy SEALs make personnel decisions? No (RBH shakes head)? Okay, find it online, but the summary is this — when analyzing how Navy SEALs make personnel decisions, there’s an institutional recognition that skills and character are frequently in bisecting axis. If you were going to do a regression analysis of personnel, all Navy SEALs are going to be graphed in the upper right quadrant — likely two standard deviations from the mean average. Within that “outlier” subset, personnel decisions will favor the more trustworthy grouping of personnel. This is where I leave the military metaphor behind because I don’t want to compare startups, or what Kris and I do, to anything so serious as military action. And, neither one of us would compare ourselves to SEALs. But, applying the same sort of graphing of people in my network, KJ is definitely two SDs from the mean, and someone that I have trusted with my personal outcome in the past. As you well know, I worked for him for years, and I briefly worked for Philip too, so this whole situation is special in that way. I trust these people.
Tell me about the young people in the office? Are you having trouble connecting with them?
Somewhat, yes. For the first time in my career, I am. And, it’s really odd. There have been a number of cringey moments where age and perspective inhibit some basic, unimportant conversations in light-hearted social moments. Nothing offensive mind you, just, well, we’re old now — there’s no easy way to put it. I’m learning to live way outside of my comfort zone. But, yeah, it’s pretty jarring for me. True or not, I felt like a cool older brother for the last ten years. I had more time to mentor and help younger people along. And, now, I’m the squinty guy the young people slow talk when replying to my questions. And, I can identify with their feelings. Thankfully, I don’t have much of an ego anymore. And, that slow talk doesn’t last long — my questions are still incisive and valuable.
What is the thing you do most? What is the thing you like doing the most?
I spend an inordinate amount of time writing and editing. My founders aren’t native English speakers. My growth and rev-ops guy is French. My video marketing specialist is from Brazil. Our US design resource is great on marketing copy, and our social director, whom you know, is near masterful in 140 characters, but he’s not a generalist in copy — at least not yet. So, yeah, I’m editing everything right now. But, it feels good — I feel like I’m a brand manager, and I’m at home with that responsibility. I didn’t think I’d be okay with this, but it’s a regular tangible contribution, something that’s visible versus the other, more critical aspects of the job that are hidden from engineers, marketers, sales staff.
But, copy is not the thing I like doing the most. I love telling the origin story to investors, press, partners, big customers that need reassurances. Our origin story is damn near a fairytale. I can’t believe no one in the press has written it up yet. It’s a beautiful story, everyone that hears it connects with our founders and product.
What is the single most underrated piece of experience that you’ve leaned on since becoming CEO?
It’s experience at Goldman Sachs – career-changing. But, I can’t talk about it because the firm is so secretive. Outside of that, Vevo was so instructive about the media industry — how media giants works, how they think about tech as the enemy, art as a commodity. Over the years I was there, we cooked up so many great products that the management just didn’t understand. The commercial team understood what Growth and Product were doing, and the A&R teams understood, but I really got an understanding of the difference between the media giants and media startups. Oddly, it gave me the right perspective for succeeding at Loop, and even GS, to a certain extent. My mentoring time — the structured relationships with the Thiel Fellowship foundation, TechStars, are always learning experiences. So too are the less-structured mentoring instances, like my loose affiliation with the 1517 Fund community, where I worked with well over a dozen startups last fall. But, overwhelmingly, I am shaped by my time at Stanford, where I continue to stay active and involved.
I know you played baseball as a catcher all the way through college. I would imagine that field general mentality comes into play quite a bit.
I love that term — “Field General.” If you’re an observer of the game, it looks like that — the catcher is so involved, calling all the defensive plays, directing traffic, coordinating with the bench. But, the demands are much more like the realities of CEO — catchers are communications hubs, they are communicating with everyone — keeping several streams of communications going on while performing. In any given inning, a catcher is telling pitchers where they’re missing, where their technique is off, and what the hitters are doing and expecting, and then there’s the conversation with infielders — telling them where to cheat ground defensively and what the pitching approach will be from frame-to-frame. And, then there’s the coaches, who are analogous to a BOD — they’re watching what’s going on, but you have to deal with their anxiety, give them reality checks on their bias and convince them of what you’re seeing from behind the dish. Catchers are more like pro golf caddies because the mental aspects of the game require very high EQ, incredible communications skills. It’s not general like. But, I think the catchers make the real transition to Generals — team Managers, Head Coaches and General Managers. A quick look at MLB managers will confirm that observation. I know a few, played with and against them.
What is your favorite aspect of the job?
It’s still the coaching. A lot of people don’t realize that I was a player and coach my senior year, the year my class went to the College World Series. Following that, I was then a player-coach overseas, and a bench coach at San Francisco State. I had other coaching opportunities, but since going into tech, I’ve found ways to continue coaching in the office. Not to brag, but best-selling authors and founders of unicorns still call me and we talk like a player and a coach. It’s nice.
What is an unexpected downside? Is there one?
Not really. I kinda knew what I was getting into. The time as COO at Loop was instructive. And, Jon’s encouragement was amazing. Niermann is a legend. A quiet, understated legend. When we started talking about me going to methinks — he was nothing but supportive. I love that guy. Seriously, like a big brother.
Are there leaders you look at and try to emulate? Those that encapsulate your values?
Jon, Michael Bayer, Raymie Stata — I think about those guys at least once a week. Like an average ballplayer, I borrow from nearly every great CEO I’ve worked for — I say nearly, because there are a few CEOs I barely worked with, so I can’t really borrow from them. But, the CEOs who I worked for who were crazy or struggling with addiction, going through personal issues, etc., I still managed to learn something from those people. And, that’s really important too. Because, if you want to succeed as a leader, you have to really like people. I know that sounds trite. But, honestly, one of the worst CEOs I ever worked for was a guy that didn’t like people. I guess he was really smart and had a great CV, but he was startlingly honest about how much he disliked people and their flaws. If you don’t like people — if you can’t engage people, and have a hard time finding empathy for all kinds of people, well, don’t ever try to be a CEO. I know that sounds kind of obvious. But, I think this is the one thing many CEOs don’t think about before they take the gig — do I like people enough to get invested in the people of this company? That’s a hard question for candidates to ask themselves.
Who was your childhood hero?
Jim Thorpe. You know I’m Native American. And, like most Native kids, I grew up with a book about Jim Thorpe — elders read it to me before I could read. The first few years of my life, my mother and I were effectively homeless, sheltered by friends and family throughout western Indian Reservations. I was always different from the other kids around me. I think the first pair of shoes I owned was at age 4 — a pair of cowboy boots I got in Oklahoma from a thrift store. Shortly thereafter, I moved to California to stay with my Aunt, and my attire was a difference that other kids ridiculed. For most of my formative years, I was socially different, awkward — looked different, poor, working hard to just be normal. I over-achieved, but, whether it was my race, my social status, I struggled to be accepted — you know this, we’ve talked about it before. But, one way I coped as a kid was by clinging to the stories of Native Americans who were success stories. Jim Thorpe was it man — not just for my generation but for the generation before too. Of course, the kids books didn’t share the whole, sad story of Jim’s life. But, the athletic exploits — amazing stuff. Later in life, I had heros in my own family — my Grandfather’s heroics in WWII, my great grandfather who drove a stagecoach, if you can believe that. But, as a child, it was Jim Thorpe and then Carlton Fisk when I started to play baseball. For guys my age and a bit older — nobody was more manly than “Pudge”. He had it all — the movie star looks, the size, athleticism, the awards and that awesome sense of pride, you know? Fisk looked like he’d rather eat his hat than endorse a hotel chain or have a TV talk show like Johnny Bench. His intensity and passion to compete, drop his glove and fight any Yankee, at any time — he inspired me to wear #27 straight up through college. I want to meet Fisk one day, just to shake his giant hands and tell him how much he meant to me.
Describe yourself in one word?
I really hate talking about myself. You know that. So, good question. I’ve worked hard at integrated thinking as a means of connecting more with people. It might have made me a little too self-conscious and analytical in choosing words. And, of course, this is where I want to digress into meanings and secondary definitions, but I won’t. My wife says I’m contemplative. My mother has said I’m introspective. Someone once described me as a “word-snob,” as a compliment which made me monosyllabic for a month. I’ve been called “woke” and “present” by younger people I mentor. I don’t think I’m all that sophisticated as those words feel, so I’ll go with “aware.” I think that’s fair and accurate. I’m immediately tempted to add “painfully.” Is that wrong?
About the interviewer:
Richard Brewer-Hay has 20 years experience in communications, marketing and production on behalf of some of the world’s most innovative companies, including Yahoo!, eBay, NEC, Microsoft, and StubHub. In November 2014, he joined Splunk to lead its social media efforts across the global organization. When not Splunking, RBH spends as much time as possible with his wife and two daughters – exploring the Bay Area. He also brews beer. In April 2010, his beer – “Imperial Jack,” named after his grandfather and brewed in collaboration with San Francisco’s 21st Amendment Brewery, was a Gold Medal winner at the World Beer Cup.