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The super{set} CEO

October 10, 2022
Written By
October 10, 2022
Episode 23
46:16
Written By

Tom and Vivek describe what the ideal CEO looks like in the early stage, why great product people aren’t necessarily going to make great CEOs, and what the division of labor looks like between the CEO and the rest of the early team. They then bring on special guest Dane E. Holmes from super{set} company Eskalera to hear about his decision to join a super{set} company and his lessons for early-stage leadership.

At super{set}, the money from our venture fund exists exclusively to fund the companies emerging from our studio at inception and give the early team the time and focus to build. At inception, the last thing we want is the wrong CEO showing up, kicking up dust with too much certainty: the art in our model is finding the right CEO at the right time.

The average CEO isn’t suited for the early stage - the soul-crushing ambiguity, the need for collaboration and humility rather than go-it-alone decisiveness. At super{set}, we look for CEOs that can simultaneously scale up and scale down, that can see the big picture while also tackling the point-to-point challenges, all while being the face of company culture and talent recruitment. 

This role isn’t for everyone, but what the super{set} team brings is the companionship of those that have done it before and been in the lonely shoes of the CEO. As special guest Dane E. Holmes from super{set} company Eskalera says, “Being a CEO is hard and lonely, doing it with other people who've done it makes it a little bit better. It's still very lonely, it's still very lonely, I wouldn't go to happy, I would say, but better.”

Transcript

Welcome to The Closed Session; how to get paid in Silicon Valley, with your host, Tom Chavez, and Vivek Vaidya.

Tom Chavez: Welcome, everybody. This is episode five, season three of The Closed Session. My name is Tom Chavez.

Vivek Vaidya: And I'm Vivek Vaidya. It's been five episodes Tom.

Tom: We are rolling deep.

Vivek: I Know.

Tom: Now, it's a bummer because the prior episodes we had some video, and then we haven't had video in the last couple of episodes because our man, Steve, is away for a little bit. But we'll be back on video because I'm already getting crazy texts and slacks from people, I need to see Vivek's beautiful mug.

Vivek: Of Course. And I thought we would be on video again today, so I got a haircut like last time.

Tom: You got another super cut haircut?

Vivek: Mm-hmm.

Tom: I love that.

Vivek: See.

Tom: 27 bucks, you just walk in. But have you figured out what your... Because we talked about that the other day?

Vivek: Oh, yeah. Here we go.

Tom: The lady at the super cut asked you your...

Vivek: For my number.

Tom: Your number, and you don't even know your... After all these years, you think of going to super cuts, you would think an Indian man would know his number.

Vivek: No. See that's the thing, when you get haircuts in India, first, you go to the barber and you tell the barber, I like it short on the sides and back and heavy on the top, and the barber just knows what to do.

Tom: Okay.

Vivek:Because they use scissors, they don't use the machines like over here.

Tom: We're not in India anymore.

Vivek: I know. I know, more's the pity.

Tom: We're in the United States of America, you got to do it our way.

Vivek: I know. I know.

Tom: I think we talked about it and I suggested a number of-

Vivek: So, here's what happened-

Tom: I suggested five.

Vivek: Here's what happened, so I said, I want six, and she said six is not short, five is short, okay?

Tom: Yeah.

Vivek: So I said, what is the longest short number you have?

Tom: The longest short number? Because you studied a lot of math.

Vivek: Yes.

Tom: There're long short numbers.

Vivek: Yes. She said five. Okay, let's do five.

Tom: All right. Well, I think it looks magnificent. Whoa, was that your little device?

Vivek: That was my little device.

Tom: That was all the way live, that's how people know this is not faked or deep faked or like this not even live.

Vivek: We're recording live.

Tom: All right. Turn off your ringer.

Vivek: Yes.

The super{set} CEO

Tom: Okay. So, today we're going to talk about CEOs. And in the past we've talked about crafting, not critiquing, and setting the soil conditions for companies in super{set} to really, really take off. We've talked in the past about how our first hire is a product co-founder.

Vivek: Correct.

Tom: And we're looking for grit, humility, organized thinking, clock speed, we covered all of those elements. But it's not necessarily to bring in a CEO too early. Let me say this, I've been a CEO and I've screwed up a lot of stuff, and the problem with CEOs frequently is the wrong CEOs show up with a ton of certainty, and a lot of bluster, and they're kicking up all kinds of dust, they're a tornado of... Sometimes it's useful, more often than not it's not that useful. And so the art of it is finding the right CEO at the right time. At these companies at formation are really just a state of mind, there's all this stuff, this barn raising kinds of things that need to happen. And so what we wanted to cover today is the idea, the topic of the right CEO at the right time. And so let's jump in, shall we?

Vivek: Yeah, let's do that. I think it's important to recognize or talk about at the early stage, why companies that we build don't need a CEO.

Tom: At the earliest stage.

Vivek: At the earlier stage, because if you think about what a CEO does at the early stage, there is definitely product stuff, because it's all about building product, and we've talked about how we think about building products, message market fit, talking to customers, all of that stuff. Sure, that CEO does that, but everybody does that in the company, and you don't need to have a CEO title to do that. I think the other thing that CEOs do at this early stages is fundraising, and we account for that with our model, right?

Tom: Right. Because look, I mean, that's one of the things we've talked about, I've said CEOs running up and down Sandhill at that earliest stage, peddling idle PowerPoint with unverifiable claims, any hour you spend doing that is an hour not spent on more important things.

Vivek: Correct.

Tom: Right. So the premise for super{set} is to have a fund that exists purely and exclusively to support those companies at formation, we don't chase or look at other things. So, it reminds people of VC, and we always have to deflate people's expectations, we're like, wait a minute, I'm glad you have a thing, but we're not for you.

Vivek: Correct.

Tom: The money exists, again, exclusively to support our company's information. So, that frees up a lot of time and creates space for teams or at least age teams to go and get it right. Now, look, I think that there are, we're talking out of both sides of our mouth here because great CEOs are so necessary. And I think that the way Silicon Valley has conceptualized them frequently is not fungible, but I can go out to market and find a great tech CEO to operate and lead an early stage company, and I violently disagree. What's your mindset on that?

Vivek: I think the first thing I will say is that at the early stage, and especially for tech companies, CEOs need to be product-focused because especially the early stages, it's all about the product. And the market oftentimes confuses, oh yeah, we'll in somebody else, because it's just about selling, it's not about selling at all actually. At the early stage or even beyond you can hire great salespeople to come in and sell your product, but you need to focus on the more important things, like message market fit, and product market fit, and then staging and sequencing the company, et cetera.

Tom: And in our last podcast we talked about the dome of the temple, that longer arc, so you have to begin with the end in mind. And the right CEO isn't going to be out there just peddling individual features and functions in a product, but mapping speaking authoritatively to all of the ground level capabilities of the product but in a way that maps convincingly to that longer arc we talked.

Vivek: That aspirational inspirational vision for the company.

Tom: So, it's the whole enchilada. And at this early stage look, it requires a lot of patience and delayed gratification. And I think one of the things I've seen is that most CEOs are too impatient to deal with the soul sucking drudgery, and crippling ambiguity that comes with this early stage.

Vivek: And there's also the question of ego because CEOs, people who have that mindset come in, I want to make some decisions, I want to be the one who decides everything. And at early stage, it's not about that at all, it's about collaboration and sitting together at the kitchen table, blueprinting asking each other questions. As we said on the last podcast, I say it, you say it, there's a lot of that, which requires a certain amount of humility that outside CEOs oftentimes don't have.

Tom: That's right. Look, we're going to have a guest join us in a bit who is the exception that proves that general rule we're talking about. And here we are again, somebody who can scale up, scale down, be able to see the whole picture, be patient enough to deal with the early stage point to point challenges, right?

Vivek: Correct.

Tom: And in addition to all of the team building and core leadership aspects that come with the job.

Vivek: Correct. 

Tom: So, we've spent so much time talking about product here, and I worry at various moments that maybe we overdo it because there are different spectrums, different swim lanes, and great product people aren't really necessarily going to make for great CEOs.

Vivek: That's right.

What We Look for in a CEO

Tom: How do you think about that division of labor? This is a tricky question, how do you think about what a CEO does when he or she does it well, versus all of the product leadership that we've talked about? How are those roles different? How do they intertwine?

Vivek: I think, again, the answer evolves over time as the company matures, but even at the earlier stages there is a lot of dividing and conquering going on. So, if you're a team of two or three people as co-founders trying to build a company, designing product, what have you, you still have to pay attention to the recruiting dimension. And yes, everybody participates in the process of recruiting, but somebody has to be the front man or front woman for this recruiting process, somebody has to be the face of the company, and oftentimes that is the CEO. And so that's thing one, the second thing is culture. The CEO, of course, everybody informs and participates in building creating culture in the company, but somebody has to lead the effort, just like the product leader is responsible for leading discussions, organizing conversations around the product strategy, same thing with culture and recruiting when it comes to CEO.

Tom: And it is remarkable to me how many tech CEOs first, just don't have any respect to regard for that, and I mean, and how many of them just totally suck at it, if I'm speaking politely, we're going to come back to that when our guest arrives. Because look, you and I have both learned a long hard way, what's Drucker's line? Culture, eat strategy for breakfast, I mean-

Vivek: All day long, yes.

Tom: You can have a kick product, you can have a money making machine, but if people aren't engaged, inspired, involved in the way that, as you're pointing out, a CEO needs to drive, and the long arc these companies don't really... By the way, in that moment, let's look at Microsoft as a quick example.

Vivek: Yes.

Tom: Because we were both there.

Vivek: Great example.

Tom: Right. Before Satya arrived, and I know I'm mythologizing the guy a little bit here, but you could see a company at scale just withering on the vine.

Vivek: Crumbling.

Tom: And then you have this guy Satya comes on in and just breathes life as far as we can tell into every nook. And we were talking to somebody from Microsoft a couple of weeks ago who was reporting from the ground, this is employee 195,262, from that employee's vantage point, this company is on the move. So, it reminds me of Kissinger's statement once about, yes, there are geopolitical forces, and social economic events, and so on, but people can make all the difference. And here the CEO shows up and can breathe life into a company, as Satya has at Microsoft. In the early stage, the CEO gives the count, paints the vision, and it is so critical, it's hard work. And when you see it screwed up as many times as I think we do, you get even higher regard for how important.

Vivek: I think we should clarify one thing that when we talk about early stage at super{set}, we say, oh, we don't look for a CEO, that doesn't mean that we don't there is nobody paying attention to these aspects of culture or recruiting, et cetera, we are the CEO, and by we, I mean, super{set}. And so we create the right division of labor with our product co-founders that we bring on board, and with this division of labor that everybody contributes their bit to the overall mission and vision of the company.

Tom: That's right. Well, so I had mentioned something before I want to come back to it in this context because the Silicon Valley framework around this, around the fungible CEO is you go out to market once you have a thing, and it's just chunking along, and I am going to speak garishly about percentages and such so if everybody wants to kick me into the table too bad, I'm saying it. There was this, this benchmark of 6 or 7% of the company for a CEO to come on in, take the reins and do the thing.

Tom: All right, that was the market price. It's probably teetered around some of that, I'm sure Sloman got something more at snowflake, whatever, or maybe not, I don't even know, but that was the market price. What we're talking about here is a totally different species because it is not for a company that is just Primordial soup with nothing going, but it's not a company that is in that strike zone and just chucking along where the CEO comes in. And by the way, the principal job of that CEO at that stage typically is just not screw it up.

Vivek: Yep.

Tom: Right. There's still a lot of wood to chop. And so what we're talking about here, and it's important because I see a lot of other venture studios being too greed, what we're talking about is equitizing the entire team including the CEO at a level that makes it worth their while. If you found the right person, no one is going to quit, and we're not talking about small potatoes here, it's got to be a meaningful slug of the company because they're going to do a tremendous amount of work to take that company up the hill and all the way to the moon.

Vivek: Actually, I was having a conversation with a VC friend of mine the other day about our model, and so the usual questions came up, how do you incentivize people? And oh, it's not going to work for external people coming in. And when I explained how the equitization of CEOs and these part co-founders work, they were like, wow, no one's done that before.

Tom: That is correct.

Vivek: Are you sure you guys do that?

Tom: Yeah.

Vivek: Yes we do.

Tom: Are you sure you got those numbers right?

Vivek: Yeah.

Tom: No, I'm pretty sure. I mean, and that's a conversation actually, I just had with one of the investors who's looking at one of our projects, and there's this concern about, well, what's going to happen if you or Vivek get hit by a bus, or you're not here to do the thing? And I just had to courteously remind this person, and this is a nice lead in to the introduction of our guest, have you seen our record? Because it's not happy talk, we're actually doing it.

Vivek: Yep.

Tom: So, with that, I think it's a very good time to bring in our guest.

Vivek: Let's do it.

Tom: Shall we do it?

Vivek: Let's do it.

Special Guest: Eskalera CEO Dane Holmes

Tom: Okay. Ladies-

Vivek: Drum roll please.

Tom: Right. We're going to have them add a drum roll, this is the part where they add the drum roll in post-production.

Vivek: Okay. I don't have to [inaudible 00:15:19].

Tom: There's the drum roll. Ladies and gentlemen, it is my great privilege to introduce Dane Holmes to The Closed Session Podcast. Dane is the CEO of Eskalera. And Dane, welcome.

Vivek: Welcome, Dane.

Dane: Yes. Thanks for inviting me to the party.

Tom: And it is a party, it's a lot of nonsense.

Vivek: As you will soon find out.

Tom: It's a lot of Tom Foolery and just utter nonsense. Dane, it is great to have you with us here. We were talking a lot about you, your ears must have been burning because look, we're examining the role of the CEO in an early stage context, like the ones we create over here at super{set}. And we want to be able to speak plainly with you about the whole journey. You're going to get grumpy at me now but I got to say it, so Dane comes to us from Goldman Sachs, where he was on the management committee of Goldman Sachs, which he's in the inner sanctum, forget the inner sanctum, he's in the star chamber, and a long very successful career on Wall Street in various roles at Goldman Sachs before finally taking the reins as head of human capital management, which is Goldman's way of saying chief people officer, right?

Dane: Correct.

Tom: So, an incredible ride. And I want to flash back Dane to that dinner we had in Manhattan a long, long time ago, where I think because I was the CEO of Eskalera, we had maybe two or three customers at the time we'd built the early product, and of course, I'm trying to get Goldman Sachs to sign on as a customer, you were on the other side of the table, these funny times. And then I remember we had a steak dinner at a fancy place in Manhattan, and you mentioned that you were wondering about whatever was next.

Dane: Yep, correct. It was, it's funny to go back there, God, a lot has happened since then. But I was in the standard position of trying to decide did I want to learn something else having spent almost 30 years on Wall Street. I was thinking Hey, there's another big world out there, the tech world being one of them, do I want to lean into that and experience that? And knowing that you had so much experience in it, I was going out to dinner thinking you were going to help me figure out what other big tech company that was recruiting to me I was going to go to. And I don't think we made it to appetizers before you said that's a bunch of Tom Foolery, and there's a way better idea for you, should come over and work with, and we should build this company Eskalera.

Dane: And I was like, well, this is a different formula. And I'll never forget, I went back and spoke to my wife, and she's like, oh, how was your dinner with Tom? Did he help you figure out which of these tech companies you should really prioritize? And I said, no, he came up with option B. And so here we are. So, be careful about going to dinner with the really smart people, that's the-

Vivek: That's the gist of it.

Dane: That's the gist.

Tom: Well, and I think I do remember when you were at dinner and you had to step away to take a call briefly, I put something in your martini.

Dane: There you go. There you go.

Tom: I've been feeling bad about that, I feel like I should have told you that long ago, but the truth comes out now.

Dane: Hey, I've been trying to avoid roofied my whole life, I should have known it was a tech entrepreneur that would do it to me.

Tom: So look, you as you were saying, I remember you had some big jobs in fronted positions, and you were on the cusp, and so obviously you have some chromosomal imbalance that made you decide to go and do this thing at Eskalera. Can you talk more about how and why you made that decision?

Dane: Yeah. There was two things that one, so one was some self introspection on my part, which I'll talk about in the second was something that you said that I've like utilize and at this point almost claim it as my own. The self-reflection component of it was whenever presented with a problem or situation that you hadn't previously thought about, I go immediately to frameworks. So, I had to put a pro and con framework in place right away because my head was exploding. And so part of that framework had in it what did I want for myself as an individual? What did I want for the others I was going to work with? What environment did I want to have? And then the last was, what impact in the world did you want to have with that? So, those three layers.

Dane: And I started listing it out and what was scary about it was I was going down this other path that was scoring very poorly on that framework. And I was going down this path, it was scoring very high on this under this framework. But I don't know that I would've created the framework if I hadn't been presented with the challenge. And I think this faces a lot of people where they're on a path and they just stay on their path, and do they really take the step back and say, okay, I might like where I'm headed, but is this where I want to hit? Is this my optimized direction? From that perspective, the opportunity through all three of those lenses with Eskalera was just ticking the boxes, which was great.

Dane: The second version of it was something you said to me, and you said, Hey, do you want to be all hat and no cattle? And that was a very probing question because of course when you live in corporate America and you grind your way up the corporate ladder, and I'm sure this exists in small company context too, you acquire a lot of hat, the hat gets bigger, you put a feather in it, it's got some turquoise banding on it, I mean, and you start to say, Dane, that's a nice hat. But at some point you can also say, but my ability to affect change, my ability to make decisions, my ability to create the culture that I want, no cattle man, I'm a cowboy with a sweet hat, sweet setup-

Tom: Big old lasso whipping around in the air all day long.

Dane: Exactly right. Everybody, when you walk in a room, they say, look at his hat. But your ability to actually do the to say, no, I got a 100,000 steer cattle and I'm a real cowboy, is harder. And so that stuck with me, and I just said, no. And also from my makeup, I cared less about the hat, I acquired the hat, but it honestly didn't mean that much to me, but the cattle mattered a lot. And so that started part of the formula, and boom, next thing we're here.

Tom: Crazy.

Vivek: So, when you first heard about super{set} and the model, what were your first thoughts like?

Dane: Thank God.

Vivek: Yeah?

Dane: Yeah. Because one thing that I've tried to embrace the whole time is a little bit of humility. I think I came onto Wall Street in 1992 where all of the captains of industry got destroyed. So, I had this benefit of entering in a down cycle. And I just remember that the people that I was interviewing in 1991, by the time I arrived in 1992 were fired.

Tom: Wow.

Dane: I had a lot of humility around it. And so I came, to continue the cowboy hat analogy, I might have had the big hat, but I came and I said to myself very clearly, I've never done a startup before, I've never been a startup CEO, this isn't something that I've actually done, it's something that I feel like I have the potentially be successful at, but Hey, you leave me alone with a glass of Bourbon, I can come up with a couple of dozen things that I'm not good at. And so the concept of having people who've done it before who are aligned with you, fully aligned, not like I'm aligned in the economic component of what you're doing, I'm aligned in all aspects of what you're doing, and having them as a resource, I mean, in all frankness, I think if I didn't have it, I don't know if I would've done it because I wanted to be successful.

Tom: That's very meaningful Dane, to hear you say that. I mean, it is a ride or die situation, and we are proud. Look, I mean, it's tricky, it's not tricky actually, because you're the captain of the ship, and then when we fact that transition it's very clear, Dane is the man he's going to carry it forward, but please put us to work as you have, we stay close, and we don't want to be people who just show up at board meetings and critique your craftsmanship or ask you, why are the numbers as such as they are? Which are important questions.

Dane: A hundred percent.

Tom: But you got to be aligned, and in the foxhole, and feeling everything that's going on in the business.

Vivek: Yeah. I think one thing that I've really appreciated is that, because sometimes it's difficult for people in your position as the CEO of the company to really think about us as super{set} in like, they're on my board, are they actually going to roll up their sleeves and work with me? And also, am I comfortable disclosing all these challenges I'm having because they're on the board? So it's been actually from our perspective, very gratifying to see that trust has been established so that we can go in, and we can say, I'm putting off my board hat now, and I'm putting on my company builder hat now, and I'm going to work with you to solve these problems.

Tom: We do that a lot, and it sounds a little silly, but Vivek and I frequently stay like, okay, taking off my board hat, I'm taking off my boss hat, now I have my friend hat on. We just change hats all day long.

Dane: Yeah. And listen, I think the other big difference is frankly you've done it. So for you while I know there's this little bit of a change, my guess is also based on my experience, you can very quickly go into operator mode, you've been there, it's not some distant thought or some philosophy or some business school course you took, you're like, no, I remember that pain, I can actually go back and remember when I hit it, which is helpful. Vivek, you said something else there that I thought was really important, which was around trust. And I've always had this belief mechanism, a lot of people say, oh, you have to earn their trust. I've always thought of it as trust as a gift, and over time the gift is either confirmed as having been a good gift to give, or maybe a bad gift to have given.

Dane: And so I entered it with, I'm going to trust it as presented, and the beauty of it has been is every day that I come in, that's validated as having been a good gift to give. And so I would push other CEOs, I think sometimes this is their mistake. Being a CEO is hard and lonely, doing it with other people who've done it makes it a little bit better. It's still very lonely, it's still very lonely, I wouldn't go to happy, I would say, but better.

Tom: It's still going to be hard AF, but when you have people and thought partners you can confide in and talk to, by the way, that was my journey in my first company, it was so lonely. And so having true partners, true co-founders for real who are going to be there. And look, I mean, it is a delicate thing to say it, but I think I mean, I'm still operating and I'm still a CEO, I get a little seized up when I'm talking to investors and feeling like, oh, no, I don't know if I should really blurt all of that out, I don't know if I should be venting and saying what I really think. And that's just the nature of the beast, right?

Dane: A hundred percent. I mean, it's such a challenging thing, I think it applies to your team, I think it also applies to investors and other stakeholders that are involved, is this question that I think if you're being a thoughtful CEO, you're always debating, is sharing this information empowering, or distracting, or actually misdirecting? And some people be like, oh, just be fully transparent, no full transparency isn't always very helpful-

Tom: Got to be careful.

Dane: To everybody that's involved.

Tom: That's right.

Dane: And by the way, we've all seen our relationship where when you're in a good place in your marriage, they're like, you know it would've been helpful, honey, if you hadn't told me that, I actually didn't need to know, that wasn't helpful. Oh, men. And so I feel like when you're a CEO, the one thing you have is you have access to all information in many ways, and in some sense you're running a very complicated algorithm about how do you put that information out in a way that's useful?

Vivek: Yes.

Tom: Right.

Vivek: And I think that's what most CEOs struggle with, they either are on full transparency, which is not as you've said productive a lot of the times, or they are on very little transparency. You have to figure out-

Tom: Hide the ball with the board, don't say what's really going on, that's dangerous too.

Vivek: Correct. Not just with the board, but with the employees too.

Dane: A hundred percent.

Vivek: Because this information sharing has to transcend to employees as well. You give them the right amount of context and they do wonders, if you share too much, perhaps it gets counterproductive, you share too little, they're not able to do their jobs properly.

Dane: I often joke that anybody who says they want to be very transparent, their first speech around transparency should be, and to be clear, full transparency means I will tell you that I know things that I'm not going to tell you, I'm being transparent about that.

Tom: Meta transparency. Now, you're snapping me back, I remember my first company when I was a baby CEO and still learning so much, I remember walking through the office once and my face was low, and I think I literally had a stomach ache that day, and it just spiraled into this chatter all of a sudden about, oh my God, there's a layoff coming, I saw Tommy looked terrible. And it was my moment to learn like, wow, this is some heavy stuff here, and I got to really manage my aspect carefully. Speaking of like, not too much transparency and by the way, chin up if you have a stomach ache, maybe work from home that day, whatever, it's just emphasizing your pointing Dane, it's a lonely hard job and the stakes are high.

Dane: Yeah. It's so funny. You tell me that story. I had one of those ones too when I was running investor relations at Goldman during the financial crisis.

Tom: That was an easy job.

Dane: Yeah. Yeah. It was-

Tom: That's totally a phone it in job.

Dane: It was totally, it was intense. But one of the parts, one of the things I'll never forget, and I kept this forever, so it's the middle of the crisis, I'm running investor relations, and I'm coming into the office, and I'm just doing what I would call my morning calculus; I got to do this, I got to do that, just literally running through everything that's got to happen over the next 18 hours or whatever. And I get back to my desk and I felt like energized, by the way it was a crazy mark, but I was in a good mood, I was like, we're getting stuff done. And my phone rings, my friend was like, Hey, Dane how are you doing? I was like, doing great, man, why are you calling me? He's like, I just wanted to check in because one of the guys who works for me was in the elevator with you when you were coming up and said, you look super like focused and intense, and they were freaked out, and was like, is everything okay with Dane?

Tom: Oh, boy.

Dane: I said, dude, I was doing my morning schedule run, that's what I was doing, everything's fine. But it made me realize, and from that moment on it was so funny, every time I got in the elevator regardless of what was happening in the outside world, I talked to everybody in the elevator, I pushed positive energy out. And you realized that's a huge part of it, that's a huge part of leading, it's just the energy you emit out.

Tom: Yeah. Well, speaking of trust and transparency, I'm going to share something here that I don't think I've ever told you.

Dane: Oh.

Tom: So when you were-

Dane: It doesn't involve my wife in any way, does it?

Tom: No, no, no.

Dane: Okay. Perfect. I just want to make sure.

Tom: This is all about Dane now.

Dane: Okay.

Tom: Easy. So, I remember when we were still sorting out whether or not you were going to join Eskalera, I had trial ballooned this with an investor mentor of mine, and I said, Hey, here's what I'm thinking. And this person came back with great certainty that only investors typically can muster and says, Tom, that is the craziest stupidest idea I've heard in years, you're going to get a Goldman Sachs guy to come in and lead an early stage company, are you high?

Dane: No.

Tom: What's the matter? So, it was set in that context. Now, he had good reasons because anybody looking at it-

Dane: I understand that thought process.

Tom: Right?

Dane: Yeah.

Tom: So, where I'm taking this now is, and I think I mentioned it before we brought you on, Dane Holmes is the exception that proves a general rule, but the question is, I mean, I got to believe that you have a lot of people from your old world who are looking at you with some degree of envy and wondering how did that guy do it? So, what advice would you give to them? And how do you make sense of this ridiculous leap? What are the things, you mentioned humility, so I'm going to say that, you don't show up and now it's what was behind that person's skepticism, like Goldman Sachs guy going to come down and live on the earth with mere mortals and not carry on with errors and all of the trappings and pop and circumstance that I think a lot of Goldman Sachs people carry on? So, you didn't bring any of that, but what other things as you reflect on the journey, what other things have made it possible for you?

Dane: Yeah. So I think it was a lot, I mean, first of all, I think you have to be honest with yourself about what you're giving up. And I'm a super optimistic person, so this also fits with me in this world because I think to be a startup CEO, you have to have pretty heavy doses of optimism, if you don't game over, just go back to the corporate world and never come back.

Tom: Dane, I said along the way without my optimism, I'd barely be 163 pounds of hype, that's it.

Dane: It is very true. But for me, I think some of it was an analysis around what problems did I want to have?

Tom: Yeah.

Dane: So, even though on the opposite side that sounded like a pessimistic approach, so the problem that I felt like I wanted to have was the problem around, Hey, I got to recruit more people, hey, I have to go out and raise money. The problems I didn't want to have is politics, I didn't want to have to overly deal with bureaucracy, I wanted to be able to get to decision making. I didn't want to feel like I had to ever compromise values for outcomes. In many ways, those were the other things, which I think sometimes when you operate in a big organization and you move up, and this is natural managing politics, bureaucracy, and trying to figure out how you can find the middle ground between operations and values, is what you do.

Tom: Right.

Dane: And so I just had gotten to the point where those weren't the problems I wanted to have.

Tom: Right. That's an interesting framework.

Vivek: I think one other thing that I would add from my perspective, one of the reasons why I think this has worked as well as it has, is you came in with a lot of passion for the problem and the product we were trying to build at Eskalera. Well, I think that's one of the things that might have been behind that skepticism is, well, they'll just come in as sales people.

Tom: Or functionaries [inaudible 00:35:02].

Vivek: Whereas, what we got with Dane was a lot of passion-

Tom: Acumen, and understanding in context from yeah-

Vivek: For the product. The problems and the product, the solutions needed to address those problems.

Tom: Well, and I've said it, and I'll say it one more time with Eskalera, Vivek and I have a lot of passion for the company, and that's why we got the ball rolling as we did. And there's zero question in my mind that Dane is a thousand times better equipped than I am to carry the company forward as CEO. So, it's acumen, and the passion, and the context, and it's these intangibles that investor couldn't perceive, and that we certainly felt like we saw. And then there's always a little bit of pixie dust and luck in, while I meant to start writing, you need all that to light up too.

Dane: Exactly. Although, I would like to use this particular conversation as the moment where we create some anagram like TDV or something like that. Because Dane at Eskalera has sprinkled us of common vacuum. The way I think about it and I think this is the super, I think this is the value, is that where can you come with whatever skills and passion you have? And I appreciate you saying that passion problem, I have deep passion for what we're doing, I think the world has to have this. I don't think this is a, should have, nice to have, it's just going to become existential if you don't have what we're trying to do.

Dane: But on top of it, I think it's fair to say that the Dane sitting here is a Dane sitting here as a result of having been able to marinate in this pond that is super{set}. And if I didn't have that, Dane's a little different. Dane sitting in his own little shared office space, trying to do this by himself, not the Dane we're talking about now, it's a different Dane. I still love him, but maybe some other people love him a little but that's the reality.

Tom: Beautiful.

Vivek: So, let's Get a little tactical.

Dane: Yeah.

Vivek: Right. What did you do when you first 100 days as CEO?

Dane: So it was interesting, so there was a couple of things because right after I started COVID hit, so it was a crazy-

Tom: Good timing.

Dane: Crazy, crazy moment. Exactly, right. So the first thing, there was really two strands that I was going down simultaneously. One strand was, I had to assess the team that you had already. It was like, I inherited this team, what are their motivations? I'm a huge believer that if you don't have alignment among your senior leadership team, it's like having mud in the gears. So, I feel like everybody was aligned, but everybody had a slightly different flavor of how they wanted it to be, and which is normal at the early stage. But I get everybody aligned to the singular vision in that, and we have a bunch of great strong personalities on the team, which is what I want, but that means a little bit more alignment management. That was one.

Dane: And the second thing was, do we have a product we can sell at a reasonable economic product? I love the product, but in the end you got to get out of your hype and you got to get into others and start thinking like, Hey, what per heads can we get? What contract can we get? What can we really do with it? And so that was the second thing. So, those were in the first 100 days. The back half of the 100 days, I would say, that was the first half, the back half was just clarity and a lot with working with you on the long-term vision.

Dane: Okay, this is step one, and we know we're aligned on step one, can we make sure we're aligned on step three, four, and five with the direction that we were going? And so we had obviously done a bunch of that conversation before I joined, but as you arrive and then you're like, okay, let's get back together and agree that this is what we will do now with full information, you have full information on me now, I have full information on you now, let's do a redo. That was the other thing.

Vivek: Because as you evolve that thinking you also have to enroll the other members of the founding team or the leadership team and bring them along with the evolution because at Eskalera, the other people on the leadership team were there before you came on board as well so how was that process?

Dane: Yeah, so I've used this analogy, I said, imagine that you're only allowed to have one child, but it's with eight parents, how would that feel from a navigational perspective?

Tom: Sure.

Dane: Because I know we're all married, we all have kids, we were navigating with our spouses around that, imagine you had seven others, that you had to navigate to, and then navigate them against each other and all that. So, I think that process it's once again, when I'm faced with difficult things I put in frameworks. There were two frameworks that I think were super positive for us, which was one as one, an agreement amongst all of us of what were the three things that were going to make us successful

Dane: So, that we could start saying, Hey, if it's not doing one of these three things, it's less important, it doesn't mean it's off the list, but it's less. And when you're starting a company, what's important feels like everything, you want to do everything. That was one. The second was how decisions were going to be made, and this was an interesting, but very positive one. I put out a nine square box that on one axis had level of agreement amongst the senior leadership team, and on the other axis was the impact on the business.

Dane: And I basically said, okay, at the bottom of it is largely agreeable, a lot of disagreement at the top end of the axis, the other one low impact on the company, high impact on the company. I said top right, not a lot of agreement, big impact on the company. We are a monarchy, I make the decision.

Tom: There you go.

Dane: Period. As you move down to lesser impact, more levels of agreement... By the way, bottom left box, I'm not even in that conversation, I have nothing to do with it, you guys will decide. In the middle, it'll be the people have the most to say, it'll be an oligarchy if you want to think about it that lightly, but that's how that's how it's going to work. And I think everybody got that. And once we got everybody on board that, Hey, that's how we're going to make decisions. And yeah, Dane's a CEO, you actually are going to give me all the realm to run when I'm in that lower section of the nine box grid, but as we move up-

Tom: Right.

Vivek: I think that's a great framework.

Tom: That's a great framework, and that's great leadership. Because if you look at how these companies unfold, and there's a little bit of tension here because we are also talking about the humility, and the egolessness with which Dane shows up and which is necessary to make this leap, that feels like that's in conflict with the thing that Dane just said, but that is exactly the job. Abraham Lincoln said, and I quote this line, he had a team of rivals in his cabinet, and everybody with strong opinions, just like your team, and he would say, if this decision is to be made, I am certain, I must make it. Just a wonderfully calm way of putting everybody back up on their stools and claiming power, the way the job requires, you can't shy away from it.

Dane: A hundred percent. But on the lower end of the box, which by the way, I say, let's just be very clear too, if we were to put out a graph of the type of decisions made, they're going to cluster to the bottom left, we're not every day going to be facing some material company decision that we have massive disagreement on, that's the infrequent part of it.

Vivek: We're not doing something right.

Dane: Yeah, exactly right if you're there. But the other part of it that I also thought was so important, and I've said this a lot of times, there's many times when I'm making a decision and I actually believe my decision is better than the decision the person wants to make. Now, whether that's ego or actuality, but let's just suggest for a second, it's actually correct, my decision is slightly better, overruling them does still have a cost, of motivation, of empowerment.

Tom: 100%.

Dane: So, you have to always I think ask yourself at what cost am I willing to be a little more right?

Vivek: Oh, yeah. Trust me.

Tom: Well, and a good CEO picks his or her spots.

Dane: Yeah.

Tom: You got to pick your spots.

Vivek: That's been my journey actually, I know that the path you're on is going to lead you into the ditch, I'm going to let you do that, I'll pull you back at the right time, but if I don't let you do that, and I just override you, or overrule you over here, you won't have that learning. That's been a huge part of my journey as well is giving people the room to make mistakes even though you know that they are down a path that is going to lead to a mistake.

Dane: 100%. And then the even superhuman second step of that is when they're in the ditch, don't stand there, going in the ditch, right?

Tom: I told you so.

Vivek: Just like I told you so.

Tom: Yeah. Don't do that.

Dane: Go down in the ditch, and pull him out and be like, dude, did you see that deer run across the street and make you go on the ditch? It had nothing to do with you, it was just a random deer that did that.

Tom: Right.

Dane: That second part's hard too, but you got to get there.

Tom: Hey Dane, this has been a really fun insightful conversation. We probably need to wrap it up, but you're going to take us out now. So, we have a little kooky thing we do around here.

Dane: All right.

Tom: And you're going to play along.

Dane: All right.

Tom: All of our fans want to hear the totally unpaid for promotion. I'm going to put you on the spot now.

Dane: All right.

Tom: This is some brand, some things, anything you like, you get to pump it, boost it, and they get the halo benefits all on you.

Dane: All right. I got something.

Tom: All right. Okay.

Dane: So, I'm a man who likes spice in his food, or I could say I'm a man who likes food, and likes spice, I don't know, you put that either way you want. But so I am always trying hot sauce, and there's this hot sauce called Truff. I'm putting that shit on everything, anything and everything. I put it on Corn on the cob last night. So, if you're a hot sauce fan, Truff Hot Sauce.

Vivek: T-R-O-U-G-H? T-R-U-F-F?

Dane: No, it's T-R-U-F-F.

Vivek: F-F. Okay.

Dane: It's like a play on truffle short, but it is good.

Tom: Nice.

Dane: All right.

Tom: I'm going to go to Amazon and get some.

Dane: There you go.

Tom: I like my hot sauce too.

Dane: Yep.

Tom: Great hang, Dane. Thank you for joining us. This is a lot of fun.

Vivek: Yep, Thanks Dane.

Dane: Awesome. Happy to be here.

Vivek: And thank you everyone.

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The super{set} Entrepreneurial Guild

Has someone looking to make a key hire ever told you that they are after “coachability”? Take a look at the Google ngram for “coachability” — off like a rocket ship since the Dot Com bubble, and it’s not even a real word! Coaching is everywhere in Silicon Valley...

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How To Avoid Observability MELTdown

o11y - What is it? Why is it important? What are the tools you need? More importantly - how can you adopt an observability mindset? Habu Software Architect Siddharth Sharma reports from his session at super{summit} 2022.

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Lessons of Grit from my Immigrant Parents

This post was written by Ketch Solutions Engineer, Sahiti Surapaneni, as part of our #PassTheMic series.

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We don’t critique, we found and build.

The super{set} studio model for early-stage venture It is still early days for the startup studio model. We know this because at super{set} we still get questions from experienced operators and investors. One investor that we’ve known for years recently asked us: “you have a fund — aren’t you just a venture capital firm with a different label?”

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Founder and Father: A Balancing Act

Making It Work With Young Kids & Young Companies

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