Fit Happens: The Executive Search Podcast

Jason Baumgarten\
\[0:00:00\]\
I'm Jason Baumgarten and you're listening to Fit Happens, the podcast where top leaders, investors and board directors share the stories, surprises and hard earned lessons behind finding the right fit. Let's get into it. We're here today with my fabulous guest, Laela Sturdy. And I'll let her do the introduction. But delighted to be here with another episode of Fit Happens where we talk about at the most foundational level, that there's no such thing as a universally awesome leader, but that instead it's the context that matters, that the right person in the right role at the right time makes amazing things happen. And what we all can learn about that individually in our careers and as leaders and as investors. So, Laela, tell us a little bit about who you are. What do you do?

Laela Sturdy\
\[0:00:48\]\
Absolutely. Well, Jason, it's so good to see you. Thank you so much for having me on the podcast. So my name is Laela Sturdy. I'm the managing partner at CapitalG. CapitalG is Alphabet's growth investment fund. So our mission is to invest in generational technology companies that are remaking how we live and work. Companies like CrowdStrike, Duolingo, UiPath, Lovable, and a bunch of other amazing companies we've had the great privilege to just sort of work closely with over the years. At CapitalG, we make pretty significant concentrated financial investments. So we have the privilege of often joining the board or board observer and working closely with these teams over many years. And as a person, I live with my wife and three kids in San Francisco and love the Golden State Valkyries.

Jason Baumgarten\
\[0:01:37\]\
And how long have you been at CapitalG?

Laela Sturdy\
\[0:01:39\]\
Been at CapitalG, 13 years. I have been at Alphabet and Google for 20 years. So I've been in tech for a long time and yeah, had the good fortune to work with amazing people inside of Google and Alphabet and then way far beyond in all of these incredible companies we've partnered with.

Jason Baumgarten\
\[0:01:58\]\
Oh, it's so much fun. I'd love to start with maybe an easy question, maybe not, which is when you look back at all the leaders you've backed or some that maybe you have not backed, can you think of examples where this holds, where somebody was exceptional but they just weren't in the right context for them? And then on the flip side, somebody where you're like, oh my God, the context was just so perfect for that person in that moment, you know, does it resonate? Does this idea that fit matters resonate or is this just this? There's just perfect people out there that everything they touch works and the rest of us should quit our day jobs.

Laela Sturdy\
\[0:02:33\]\
I absolutely think the idea that context matters sort of resonates. The example that's most glaring to me is the growth rate of a company. I think that's a context where I've seen exceptional leaders who were maybe in larger, slower growing companies that had a huge enormous global impact transition into hyper growth early days mode where it wasn't about running or operating — it was about building and adjusting quickly and making rapid fire decisions, sometimes with data, sometimes without. So that's a thing in the world that I do working with hyper growth startups who because we invest at the growth stage, they're companies that have product market fit but are typically growing 100% plus — in the AI world, now growing 300 or 400% plus — and so just need to move at an entirely different speed. And that is the biggest context failure honestly that I've seen and sometimes fantastic fit. But whenever I interview an exec or talk with people about career paths, I ask them to really think about how rapidly the organizations that they were leading or a part of were changing and how much do they like change and how much are they looking for more stability versus more uncertainty, more risk versus — you know, there's different things and one is not good or bad. But I think really understanding yourself as a leader and then really understanding the leaders that you're looking to bring onto a team with that backdrop is critically important.

Jason Baumgarten\
\[0:04:12\]\
And it's interesting because most founders, I mean some have had other professional careers, but there's scores of founders whose former job was being a student, being unemployed, being a customer support tech. They don't exactly have experience to grow fast, not like they grew some other company quickly. And now they're applying those lessons and experience. So when you think about the context that makes a lot of founders successful and we'll just pick on this one area of hyper growth. Is it like a huge tolerance for risk? Is it that they are just so deep on that particular topic that they've got, you know, they've developed some early instincts. What do you think allows somebody to be good at hyper growth specifically? I know we're generalizing, but it's always good to spend a little minute on this.

Laela Sturdy\
\[0:05:00\]\
Absolutely. To me, if I had to pick one thing, it would be the pace of learning for a founder. So you know, we have founders across the board. Some have been super experienced. As you said, this is their second or third company or they come from the industry. But most, this is their first company, they wouldn't necessarily be hired to be the CEO of the entity that they're now running. The founders that I've seen be most successful have enormous confidence, intuition, credibility, and the thing they're really good at, you know. Luis Von Ahn is on the board of Duolingo for 10 years. He is an incredible product person. His product instincts are just unbelievable. Daniel at UiPath has incredible global ambition. He just grew up in Romania, had experience working in lots of different countries. He really understood the need to build a global strategy early and get out there and sort of make decisions. So they have these certain areas, they're really spiky and they're very different across founders and CEOs. But the consistent thing that I see to make a great leader is that they are really eager to learn. And every conversation they have with someone, you can tell — whether it's you talking to them on the weekly meeting that I have with a lot of CEOs I work with, or I introduce them to a new person that leads some function — they're wanting to know that person, but also learn something coming out of it, have their view shifted, increase their capability in something they don't know at all. Such that when you meet that founder, when I first make an investment, that same person a year later is an incredibly different CEO because they have learned and changed so much. And to me, that's the critical thing that's needed to evolve as rapidly as you have to evolve as a CEO of a rapidly growing company.

Jason Baumgarten\
\[0:06:44\]\
Yeah, it's almost like because the context is changing so quickly, the key skill is learning to adapt. It's a great insight. I want to talk about how it feels to have good fit. So, you know, we often talk about being in flow or being in the zone. You were a former athlete, so I suspect you know what it feels like to be totally in the zone. It's actually a recent study about does time actually slow down? It turns out it doesn't, but our brain remembers things differently. So has that manifested in your career? Like, have you had those in the flow moments?

Laela Sturdy\
\[0:07:19\]\
Absolutely. I mean, and you hit the nail on the head, Jason. I fell in love with basketball when I was about 10 years old and I was very fortunate to play on amazing teams throughout growing up. And I played college basketball at Harvard, which was amazing. And so I very much had that feeling through sports of the flow that comes from intense hard work, preparation, and then being in a game with teammates going after a common goal and that sort of out of body experience. So you know, I have that to chase my entire life and we all know that you don't want to chase that through youth sports with your kids. So for me, you know, work has been a passion and it's one of the reasons that I love venture capital and I love being with these high growth companies and the industry that I worked with is because it is all about going after these really ambitious, lofty goals. It's around building amazing teams in real time and taking risk. Like I think to experience flow, in my view there has to be something really hard about it. There has to be something where you're really reaching for something that's non-obvious that you're going to win. Like it's not fun to play in a basketball game when you blow out your opponents. It's fun to win by one, like at the buzzer, you know, preferably. And I think that's what startups allow — is you to have a landscape where nothing is guaranteed. There's a ton of intensity, it requires a ton of preparation. It requires people and teams to come together. So I've had — I mean you can tell the similarities — I think in that I still get together with my college teammates and we talk about the good old days and I still get together with, you know, the teams of companies that I invested in their Series B and they're now public and we talk about the good old days. You know, remember when we almost went bankrupt or this went wrong or that happened and we pulled together in this way or that way. To me that's flow as a working adult. So I think it absolutely for me is essential to find the joy and the reward in kind of doing what I do.

Jason Baumgarten\
\[0:09:23\]\
It's so fun to hear you're so successful and so awesome and yet I know everybody has this thing where they're like, oh, that job or that project that was such a bad fit, I can't believe I did that, or thank God I got out of it. If you look back at your own career in a moment of vulnerability, is there some project or team or job that you had where you were like, God, it wasn't that I'm not fabulous, but that was such a good example of being just a bad fit for me personally — and more importantly than what it was. What'd you learn from that?

Laela Sturdy\
\[0:09:53\]\
Yeah, absolutely. So early in my career I worked in consulting for a couple of years, so that's sort of what comes to mind. And I loved the people I worked with when I worked in consulting. Actually just back in New York at one of my close friends' 50th birthday where we were celebrating. We started together at the firm 25 plus years ago. So it was amazing, amazing people. And we worked really hard, we worked on hard problems. So that aspect was a good fit. But what I realized early was kind of two things. Number one, I did not like client services. I really wanted to be on the team. I just wanted to have more skin in the game. I also realized then that I really wanted to work in tech because not just I love technology, but I love the pace of change. So again, that to me was older industries that were established where there was a lot of sort of waiting, structure, certainty you have to perform. But it was just, it wasn't a good fit for me. I learned that and I also learned, you know, this concept of 80/20 and the concept of really thinking critically about hypotheses and what you thought the right answer was sort of using quick data intuition to be like, this is my answer in sort of an 80/20 way, which I'm sure most people have heard. That way you don't boil the ocean, you try to quickly come to sort of points of view. And I loved that as a concept. That was like a really cool concept in consulting. But I found actually the process to deliver to a client is you had to be super buttoned up and like cross every T and dot every I. And all these hundreds of slides, it

Jason Baumgarten\
\[0:11:28\]\
was 99:1, not 80:20.

Laela Sturdy\
\[0:11:30\]\
Yeah, I'm like, let's go, we need to move a little faster. So that was eye opening for me in terms of again, if you talk about the concept of fit, that's when I really realized, you know, I need to be in a place where things need to move way too fast for everything to be completely buttoned up. And I knew that I had to find a way to get into tech and from tech. Like I worked at Google during the hyper growth years and then was able to, you know, spend the last 13 years building out CapitalG. And that has been an incredible fit for me that I would not have known with such precision if I didn't spend a couple years deep into the night building slides.

Jason Baumgarten\
\[0:12:09\]\
We share that experience so I can identify. There's been a lot of studies on — and maybe even going back to consulting days — consulting teams spent so much time getting the team right at the early days, which is always funny because they sometimes don't know what the team's work streams will be before setting the team up. But there's been a number of studies that suggest that one of the number one differentiators of great leaders or managers is actually their ability to get the right people in the right jobs. You know, it's not about getting A players, it's actually about getting them in the right spots. And so I'm curious, as you've seen companies evolve, what advice do you give founders or any leader about getting people in the right jobs for them, for the company?

Laela Sturdy\
\[0:12:55\]\
Well, let me say as a preface, one of the things I really believe in from a leadership and team building perspective is in the concept of spikiness. And this isn't perfect for every business. Sometimes you need much more well rounded leaders in different circumstances. I'll tell you, in building a venture capital team, I think this idea of spikiness is super, super important. And you know, when I think of building out the partners on my team, like having one person who literally, universally everyone's like, this is the smartest person I've ever met. Like just intellectual spikiness. It could look at any situation and be able to frame an investment thesis in 30 seconds or less with a way that just blows everyone out of the water. You know, another person who literally is a founder whisperer, you put in front of that person and regardless of who it is, they leave just being like, I absolutely need that person on my board. Those are two examples, you know, three or four other key capabilities I think to be a great, great venture capitalist, super hard to find the absolute world class. And even one of those things, if you try to package everybody into everything, it just becomes impossible, right? We can't all shoot threes like Steph Curry. Sorry, you got a basketball player on your podcast. The basketball analogies. I'll try to bring others up, but I believe in that really deeply because I think that that is what creates a fantastic team and that is what creates the real — I also love the concept, you know, know what to shoot for. You see someone making 50% of the threes they shoot, you know what the benchmark is, right? Even if you're the top rebounder. Like, it's just really good to see true excellence in all these different formats. So I say that as a backdrop because that's what I think about when you ask — is, you know, of course getting people in the right roles matters, but you also have to be honest with do you really, truly need whatever the spiky skill is or a really incredible thing that person is bringing? If not, you have to be honest with yourself that maybe the organizational fit isn't there, but if there is a spiky attribute that they bring that is absolutely critical to the business success then I deeply believe in this context, you know, you don't want the world's founder whisperer never having external meetings — get that person in the right role, to state the obvious. But it also sometimes can be a trap for people. Not being honest on evaluating talent is sort of this concept. So I think it's a both and.

Jason Baumgarten\
\[0:15:15\]\
Yeah, I love that because the two things we always talk to people about is one, what are the critical roles? Like what are the critical things you have to get done? What's critical path? Because you can't get equal talent everywhere in any organization, you always have scarce resources. Even the most high profile, high growth companies have scarce attention, scarce resources. So the first thing is like, what are the jobs or tasks within those jobs that are really critical? And then the second is being really honest about what they need to be good at. And I think it's hard, especially for people who haven't done those jobs. We've all recruited for people who do things we don't know how to do. And so you get to that point where you're like, I need the world's best customer service executive. But I've never run a customer service function. So what do people do? They add everything into the job description and say, I need great. I'm like, great at what? Because you know, you can take anything from finance to sales to product and say what within that are they really great at? What is that spikiness? So I think getting crisp on the spikiness — one is like, how good does that need to be? How spiky? And then the second is, are you even selecting the right spike? I've watched so many founders and CEOs say I need a great fill in the blank executive or board member. And then they really do it through addition, not prioritization because everyone tells them what a great X looks like and they don't have the lived experience to be able to differentiate, you know, a CFO who's good at FP&A versus Treasury versus tax versus risk versus compliance versus managing LPs in the board. And they select the wrong person. It's great to hear you talk about that.

Laela Sturdy\
\[0:16:48\]\
The great disappointment of life, Jason. If we could only have it all.

Jason Baumgarten\
\[0:16:53\]\
Well, it's, you know, I always love it when you start recruiting with a board and you're like, what are you looking for? And they're like, I'd like somebody who's done this and that and the other and you get done and you're like, are you all aligned? Yes, we're aligned. We need 48 points in this person. And you're like, okay, if you only had three, what would you pick? And then they're all misaligned.

Laela Sturdy\
\[0:17:08\]\
Yeah, yeah.

Jason Baumgarten\
\[0:17:09\]\
But it's very natural when you have different stakeholders. Even when a CEO is doing the hiring and it's a single hiring decision, often they're syndicating with their team and saying to their head of people, what do you think we need? And their head of sales, what do you think we need? And you get back and you're like, that doesn't exist in reality. There's no magic cloning process. Success can distort self awareness at times. And we've all worked with leaders who, you know, maybe don't quite see eye to eye with the world about what their fit is like, what their strengths are, what they're great at. It always reminds me of years and years ago. I met a Nobel laureate and he was holding court on a topic. I thought, God, he must have gotten his prize on this topic. And then I asked after the fact, somebody said he didn't know anything about that. He just now pontificates on everything because he's a Nobel laureate. And everyone sort of writes down what he says. And I'm like, but he knows about this other topic that's totally different. Why are we listening to him? And they said everyone just thinks he's now a universal expert. And so I love that this concept of learning and I think great CEOs of any size company are great learners. But how do you keep it real with people who are billionaires, super successful, at least billionaires on paper. How do you tell them, hey, you actually suck at that, you're not excelling over here. How do you hold the mirror up?

Laela Sturdy\
\[0:18:29\]\
Yeah, it's a great question. And I would add a complication to the founders and CEOs that I work with because they're all entrepreneurs. So they're all by definition have taken on missions that they weren't supposed to succeed on. They're taking on incumbents that nobody thought they could beat. They have, you know, if it was easier or obvious there would be a hundred people doing it, or much more than that. And so many of them have, understandably, a vantage point of like, I have to trust my intuition and gut that this can be done or it should be this way. And so it takes sort of an extraordinary person to keep the self awareness, to continue to trust what they are amazing at and the points of view that if everyone told them it can't be done, they would have stopped — and they were right and the world was wrong. And also hold that while holding up the ability to listen to others, take in feedback, be self aware. And I think what you see, what I have observed among successful people is that with time, people are intimidated to tell the super successful founders running these large companies, as you said, financially successful, most importantly business and technology, you know, they've had tons of it. So they start to doubt their own intuition on sort of questioning them. So my approach — I mean I love the human side of this job. I'm doing this because I love technology, I love businesses. It's really rewarding to bet on the small guys and have the chance that many of them become really successful. But I'm also really doing it for the people. So my sort of approach in this first of all is to have a very trusting relationship with the CEOs and the executive teams that I work with. I do a lot of self awareness work myself, so I try to model it right back at — hey, give me feedback as a board member, tell me what you think. I share my own sort of vulnerabilities and learnings as a leader. So first it's sort of normalizing that and then I think hard about like what are the points of influence that I think are really important. So whether it's feedback on as a board member, hey, I think there's this strategy element that you're not paying enough attention to and I think this is a really big issue. Or it's hey, like you're not tuned into this people thing on your team and I want you to really notice it and it has to do with the way that you interact. It's a personal sort of growth area. So I really like — first I try to not sweat the small stuff. Like I just in life give people a range of like, let's celebrate people for all the things they're good at and let's try to all know that most low side of some personality traits or decisions often has a high side. So I just sort of see life with that framework. So it means that by the time I'm coming with constructive feedback on something, I usually have the attention of people because I've sort of earned the relationship. I give them a lot of support and I'm really only going to bring and insist the things that I think are super important. And you know, I think that has worked relatively well for me. But I think I do observe the pattern of founders often not getting enough feedback — like they want more and the system around them is sort of set up to idealize them often more than it is to really constructively challenge them. So over the years there's, you know, different things that I've done — help founders find executive coaches, like really good boards that the founders trust are great ways to give the CEOs and founders a chance to be vulnerable and supported in a way that they often aren't.

Jason Baumgarten\
\[0:22:03\]\
It's a little off topic, but so important as we think about individual development and having a non performative space to get feedback and to get that perspective. Because CEOs, they have a boss and they don't have a boss, right. Everyone sort of says I want to be a CEO so I don't have a boss. And they realize they have a board. Founders are a little different because they often have control and they often have a little more veto power if they're really successful. So even the board becomes, you know, a little bit of — the board wants to be helpful but also doesn't want to get kicked off the board. So how do you create that safe space in that team? Right, because there's the operating team of the company, but then there's this unique team of the board. You know, how do you get people to kind of be in a good place when they get there?

Laela Sturdy\
\[0:22:50\]\
Yeah, look, I think there's a huge amount of variety and ultimately it comes down to the desire of the founder to really build a board team or not. You know, I really look at the founder CEO as sort of the leader of the board. And these hyper growth companies, again, like there's a whole different governance structure and public companies and in certain situations, depending on the governance there's hire and fire the CEO. But most of the time, the vast majority of it for the companies I work on, hyper growth successful startups, the board is literally a sounding board for hey, we're growing 100%, this is broken. We see this opportunity. Do you think we should expand to Europe now or in six months? Like how do we think about this competitive landscape? We have these three open roles. Can you help me figure that out? And I've seen a huge variance in different CEOs and founders on how they want to use that board. If they really see the board as a set of people that they can really trust and as partners. And again, no board is operating the company and if that's happening, everyone's in trouble. But I think most hyper growth founders want some sort of sounding board and they either get it on their board or some of them, if they don't have the right people on the board, will get it with other founders and they'll meet regularly on that. So there's an aspect of I think the business sounding board that is really important, like business questions, strategy, you know, competitive landscape, all that kind of stuff that they either have to get through our team on the board or they'll have to construct it elsewhere. And then I think probably a bit more nuanced and depends on the person is this notion of like how they're growing as a person and a leader and how they're constructing sort of a great team that I see boards getting less involved with. You know, at times they'll come and mediate certain executive things, try to be helpful, but I think it's only in really trusted partnerships where a board member can be that person to the CEO. And a lot of times it might be in conjunction with an executive coach. I mean, if you think about the Google, the famous days of like Bill Campbell in there as an executive whisperer, in some of the teams that I've worked with, we've had some great executive coaches that board members are trusted, part of that dialogue, as well as the executive team members, all with the sort of hope that this is an enormously challenging personal growth and leadership challenge, that most of these executives of successful companies scaling this quickly, moving this quickly, and it's a great way to get emotional support and emotional sounding board to, you know, keep growing as a person and to keep finding as much joy and meaning in this work as we can. Because if we're not able to do that, then all the hyper growth and work, I'm not sure it's worth it.

Jason Baumgarten\
\[0:25:35\]\
Yeah, these are hard jobs, as it turns out.

Laela Sturdy\
\[0:25:38\]\
They are. They really are.

Jason Baumgarten\
\[0:25:39\]\
When you think about founders that I don't want to say failed, but we'll say did not meet the potential that you think they could have had based on product market fit, and we won't name any names. But you think about that potential and you look back and you say, why didn't they get there? Why didn't the company hit the home run when they had so much more potential? How much of that do you think comes back to leadership?

Laela Sturdy\
\[0:26:04\]\
Almost all of it. I mean, I would leave some amount to sort of customer obsession, paying attention to who's paying your bills and really listening and paying attention there. But one of the things that people ask me, like what are the criteria for investing in growth companies? One of the things I say is I look for founders that have been able to attract talent that they shouldn't have. Like at a certain point, it's like, you know Claire Johnson, when she's a COO of Stripe, like you're like, okay, that's an amazing company, she's an amazing executive. Like you can see why it would make sense for her to be there. But actually Patrick was able to pull her from Google in a huge job really early and she could have her choice on who she could work with amongst various companies and founders. So we were early investors in Stripe. So I like that example because I think the talent density at Stripe is one of the many reasons that they've been able to achieve what they've been able to achieve. And I think that fact — it's not hard to understand why people want to go to certain companies when it's so blatantly obvious to everyone. But when can you convince people and get really special talent that we all collectively know is really special talent? Before you should, before it's rational. And that's one factor that I look for in growth investing. But overall, as we know, like look, sometimes markets and product market fit and stuff, you know, sometimes amazing teams cannot find that. You phrase your question of, hey, when that really seemed like it was there or there was product market fit, but it never really materialized. Then almost always it's team. Could they find exceptional talent? Could the founder or CEO convince them to join and could they gel that team into a high performing team and create a great culture around that?

Jason Baumgarten\
\[0:27:47\]\
And we see this all the time. I think that the reality is that it's both. You know, people will say we have an amazing culture and we have an amazing employee proposition. I'm like, do you pay top of market? Yeah. I'm like, okay, well then you don't because you have to pay top of market. Almost by definition, if you have to kill yourself to attract people, it means that you are not actually as great a place to work as you think. So I have a lot of time for people who can get that exceptional person in the job before they're ready. Like before that makes sense where it's a little bit of an irrational leap of faith. I think that is great. And I do think — you know what's interesting, we used to run this exercise. People would always say, find me the executive. Fill in the blank of the amazing company, right? And I'd say, oh, okay. And we'd go and take that executive and we'd strip that last role off their resume and we'd show them the resume and you'd say, I don't want to hire this person. They seem like a loser. I'd say, that's the person you're after. They're just one job before they became great. Right. And I can think of so many examples in Silicon Valley in particular and in tech more broadly, where people that we now hold in enormous reverence, nobody would take a bet on, nobody would hire them. They were almost like the unemployable until they become untouchable in a positive way. How have you thought about that risk equation when you are taking swings not just on the founder, but when the founder says, I have this exceptional talent and you look at the paper and go, they didn't graduate from a good college. Their job seems so — so they — how have you learned to distinguish? I'll share a few of my tips, but I'd love to hear that because I see this risk aversion often avoiding the spikiness. Like we want the person who's so well rounded, they're not actually excellent at the thing you most need.

Laela Sturdy\
\[0:29:33\]\
I think that this is such a good question and by the way, I couldn't agree with you more. I'll tell you the reality of what I see is that these exceptional leaders, as you say, the ones that are untouchable, that every company is like, I want an X of this person. Right. Like, I think of the ones that were the early generation when I was operating at Google, I mentioned Claire — it's like Sheryl Sandberg, like a bunch of people that worked in that org. Yeah, those were resumes that wouldn't matter beforehand. And then a lot of people grabbed the Google diaspora, they went to the next. And we see that across the board — Slack, you know, bunch of Slack people going to OpenAI, all those kind of things. I think the reality is there are some exceptions, but most of the time the bets on unproven talent come in the early years of the company. And those unproven talents are the ones that, you know, first 30, 40, maybe 50 people in the company that keep getting into bigger and bigger roles. And because the founder knows the person, they are willing to bet on them. But each time and many times they'll recruit external talent thinking they're going to replace that person and that external talent ends up not working and that person gets fired and the internal talent sort of steps up and takes the role. I think the reality of that is that we know there is hard to identify talent out there because that's the example. You look inside every great company and go and look at every great company and the number of promote from within that have huge jobs. I'm thinking of Whatnot right now, which is the exceptional company that I'm on the board of — a live shopping marketplace — and some of the internal leaders that they've been able to promote are just fantastic and you see the pace of growth of these leaders. But I can look at it sort of across the board as well as bringing in external talent. But it's always that mix. I think the truth is it's really hard to get other external benchmarks when you're hiring without the founder having direct access — sort of working with someone to be able to get any signal from a resume — it would have to come from some sort of other signal that somebody they worked with saying hey, I know you've never heard of the brand on this resume but this is the best person I ever worked with. I often say to people that are doing coffee chats trying to get into stuff — I'm like if you're so great, find a way for people to see your work because you don't have any signal on your resume that is going to obviously break through in a certain way. I think it's hard to expect that people will make bets. That's why they use the signal mostly of roles at companies that they admire as the best signal. And as we know a lot of those execs don't end up working out. But I don't know what to say besides the advice I give those people who are execs is go to companies in their hyper growth years and if you're really good, myself and tons of the great people I work with at Google — we were so — like I would get a new job every six months during the hyper growth mode. You just got a new job, more people reporting to you, more responsibility every six months. And I see that inside my portfolio companies as well. Exceptional talent when you have product market fit — before typically those companies can recruit the fancy resumed people, it's just the people that are high performing that get more and more responsibilities. So I don't know, it's not a great answer but to me thank goodness we have startups because we're creating the next generation of the Claire Johnson's of the world and others because the founders that will make a bet on them see their work and they don't need to rely on resumes.

Jason Baumgarten\
\[0:33:08\]\
It's so funny hearing you say that because the thing that I find so interesting is when somebody, a CEO or founder investor will say, this person's amazing, they did such a good job. And I'll interview them and then I'll talk to somebody else who goes, oh, that person's terrible. And so even two people who have worked with someone can have totally different appreciations for whether they're good, both generically and for a specific role. One of the things I've really tried to reinforce when people ask me — you know, I've done 1500 board and CEO recruitments, so I've seen this pattern over and over again of like, I'm going to be so risk averse when I make external decisions, but totally irresponsible when I make promotion decisions. So I always say three things. One is keep the score. Right? As a former athlete, you'll appreciate this. I'm like, you think you're good at hiring and promotion? Keep the score. Keep the score on the people you promoted or hired, did they work out and the ones you didn't — keep track of them. I said no. And then you went on to do great things. That's as important a signal as me saying yes to somebody who did okay, right? So that's one is like, keep your own score. And going back to this comment of know what you're good at. Are you a good talent spotter? Right. It's okay. I know a lot of CEOs who are amazing CEOs and they're just not very good at talent spotting. And I'm like, okay, but do someone on your team that can help you with that if that's not your skill. But you don't know if you're good at it till you keep the score. And I ask CEOs all the time, do you keep score? And they're like, oh yeah. I'll give you five examples of people who have done well. I'm like, you've hired a thousand people, you've hired 500 people. What happened to the people you said no to? Did they end up doing even better things? So one is keep the score. The second is take time. When I started in this business in the 90s, people used to do three hour interviews, they used to do working sessions, they used to do meals, they used to go on walks. Now it's like, well, I put you through a loop and everyone spent 30 minutes with you and then I'm going to make a decision and I'm like, it's the most important hire of your career at this moment. And you're basing it on an hour or two hours or an hour and a quick breakfast. I'm like, go deep, get to know them. And I think this is something where it diminishes the barrier between that internal person you know or the person from your past who you know and this person who's kind of scary to you because you don't know them. Get to know them. And by the way, like you may not hire them right away, you might hire them in six months, they may not want to come join you yet, but get to know them, like actually spend time with them. And I'm amazed at this delegation culture in recruiting that started to happen where it's like someone else's job. I'm like, no. When I think about the top executives in tech, the top executives in industrial companies, consumer companies, they spend a huge amount of their time personally recruiting. And it's not recruiting like the final interview. It's literally, oh, Jason introduced me to somebody and I'm now going to go on a two month adventure to fly to them, to take them to dinner to get them excited about our mission. And I do think when companies are going well, you also have the third risk which is you want people who want you, but the best people are busy, they don't know you even exist. And so how do you also de-bias from the person who wants you versus the person who's really busy but you actually want them. So those are some of the things I've often shared when people are like, oh well you know, what do we do about this? How do you get the exceptional person out there?

Laela Sturdy\
\[0:36:29\]\
I really resonate with a lot of what you said. And I think it's not all founders and CEOs that really believe in this idea. Everyone will say hey, it's super important to have a great team and that matters. But really internalized it and walk the walk with the amount of time they spend. And so I see a great deal of variety across that. And your two and three are also really interesting because some never confront that reality because the demand to work at their company is so high. But I also love your third point and I think it's very similar to investing actually. You know, you could spend all your time as an investor meeting the companies that inbound to you or you could be absolutely ruthless with your time and really just focus on the companies that you believe are the highest potential and where you run, and it's all outbound selling to them because they are so busy and have everyone knocking on their door. So I can resonate a lot with that.

Jason Baumgarten\
\[0:37:27\]\
Yeah, it's always interesting. When somebody's like, oh, I'm too busy to spend time recruiting, I'm like, you will always be too busy then, you'll never get capacity beyond yourself. What do you wish more leaders would ask themselves? But they never do or infrequently do.

Laela Sturdy\
\[0:37:43\]\
I mean for feedback in general, especially again, the trade offs in this hyper growth world. I love asking people like, what would you do differently? Like just some period of sort of, hey, look back on this time period. What would you do differently? I love your idea of tracking by the way, on the hiring side, again, to relate to investing. We do the same thing on investing because I think when people tend to look back in hindsight, their vision is always rosy. Like on the investing side to be like, oh yeah, somehow I thought every single investment that turned into a unicorn was a great idea and I would have avoided all the others. But if you really track — hey, would I have invested if I had the chance? You're humbled by just how hard it is at predicting the future. And I think to a certain extent hiring is similar. You can do things to make better decisions. As you said, you can spend a lot of time recruiting so you get the right top of the funnel. You can spend a lot of time with them and make the right decision. But every company and situation and context is different. So it's hard to perfectly predict who's going to succeed. And I think if you track, you learn more and more. So I think just self reflection in general, recording why you make a decision, making it, and then reflecting on what went well and what didn't go so well is an amazing tool as a human and as a leader.

Jason Baumgarten\
\[0:39:00\]\
Yes, may we all be more self reflective. I'd be curious. We haven't talked about AI and this is not an AI podcast, but I feel like we're in that moment in time where everything has to end with "and AI." And you and I both lived through the dot com bubble, so we both have that as a proxy of like these exceptional moments and disruptions in technology that end up being much bigger than the technology. I'd be curious, you know, how are you seeing how people are working as leaders changing in terms of their actual day to day?

Laela Sturdy\
\[0:39:33\]\
The amount of change in organizations that I've seen over the past year with AI-native companies kind of can't be overstated. And it's very related to my first point about growth stage investing in general, that you have to be super comfortable with change, but the speed required to execute and lead in these leading AI-native companies is like 100x anything we've ever seen. I mean it is really incredible. I mean I'll give you an example. I just led an investment in Lovable — a vibe coding platform. They grew — in the publicly released numbers, you know — 0 to 200 million in ARR in like eight months and are just off the charts. What's so interesting about a company like that is that the landscape is changing so rapidly around them. The velocity of the products that they're shipping and just this sheer scale. I mean you and I have been around a lot of businesses. Most — the amount of time that you take to get to 0 to 200, the people you would hire, all the processes and stuff — all of that has just collapsed in time. So it requires just a radically different way of thinking. Not just of organization building, but also I'm finding that the leaders of these companies also think about their product market fit and their differentiation as constantly evolving. Again, I think slower moving companies have like a thesis around moat they've built into it. They have some comfort of their market position. And I think AI-native companies understand that the world is moving around them. So they don't take any moat or positioning or anything for granted. And speed is the most important differentiation for the market leaders. So that's what I'm observing. And again that takes a totally different type of leader that can operate with that level of uncertainty, that level of discomfort, that level of like continuous need for speed and high performance. It's fascinating to see — I mean it's fascinating to see these sort of growth curves and evaluate investment decisions with them as backdrops and look at benchmarks and say this is totally different. And then it requires really different thinking on how you build a great organization, how you prioritize, how you think about what the critical factors are for sort of long term success.

Jason Baumgarten\
\[0:41:49\]\
So clearly speed, uncertainty, ambiguousness, all these things are very true. How does that for people who are sitting at, you know, a Fortune 100 company listening, going oh, I wonder what that day to day actually feels like. You've been inside a lot of these companies. What are some artifacts that you think feel different? You know, do they go from meeting to meeting, do they still have email?

Laela Sturdy\
\[0:42:12\]\
Do they less meetings? If there are meetings, they're very action oriented. So you're sort of like, okay, out of that we just get some feedback, we decide on these three things and it will be shipped. A lot more sort of vulnerability — I don't know how else to say it — across the board. There's not polish. There's like, okay, we need to move in this direction, we're going to ship. Also I would say from an employee, from a company structure perspective — these leading AI companies, people are much more technical. There's a bias towards sort of, even if they're not coders themselves, they now know how to use technical platforms at a level to be able to ship things. And then the marketing is very communicative and well — a lot more social. Like there's just an element of like, we're building this together as we move. There's going to be some mistakes, but there's also a constant reminder of the mission and how big this is. You see the AI labs doing the same thing. They're publishing what they're shipping, they're telling you what's coming. There's just this communication from a marketing perspective around really big things are happening and we are moving fast to lead in that way. And I see that sort of cascade throughout the organizations of companies that are going well. So it's real time decision making, it's asynchronous, much more open and transparent communication and it's a willingness — almost a necessity — of like, hey, we're going to make some mistakes, but

Jason Baumgarten\
\[0:43:32\]\
we're shipping quickly, going back to where we started. Do you think it's not 80/20 but like 60/40?

Laela Sturdy\
\[0:43:38\]\
I mean, who knows? I think what's so interesting about this is that so much of the future is being created that even the concept of 80/20 is like — I think, hey, we have to go and figure out the data and then make a thing. So much of this is about building the future that I don't even know if that's the right framework anymore. It's like, go create and let's see.

Jason Baumgarten\
\[0:44:01\]\
Yeah, that's so interesting. And then usage in the company. So this is something that we've been talking a lot about, is that, you know, if you want to understand AI as a leader, you've got to use AI as a leader. That's really hard in a lot of big companies because people have locked down IT environments. They have cybersecurity experts who are saying, please don't download every app under the sun. Sometimes people are setting up sandboxes and we're encouraging a lot of leaders to do this — to try vibe coding and to try platform models. Not just to do a search on an LLM and say I get AI, but to take it to the next level of, you know, autonomous help in your job. How much are these leaders as you watch them work using a plethora of other AI tools to be more productive themselves. Is that part of what's happening?

Laela Sturdy\
\[0:44:45\]\
All the best companies are doing that, I would say. And I think across — the AI-native companies in particular have a pride on like — top three OKR would be like, all of our processes have to be AI-native. And I think the whole belief on the future is that, you know, organizations, customer experiences, workflows will be totally different. So I think it is absolutely critical. And I mean I think the reality for incumbents is, with how fast this technology is changing, I think it is harder to innovate from a place of established workflows — changing when you have other organizations that are just sort of built natively in that way. And this is the reality of every sort of technology transformation — the disruptors have some chance and reason and there's some thesis behind why they can disrupt the incumbents who have so much embedded advantage. But I think the way that we work and being AI-native is going to be a huge part of the story for how the generations of companies that are being built now and will continue to be built really disrupt existing market structures.

Jason Baumgarten\
\[0:45:59\]\
Forget the tool for a minute. But what's something you have really changed how you do personally because of AI?

Laela Sturdy\
\[0:46:05\]\
Yeah, I mean what's amazing about what AI enables — as an investor we have this historical trove of information. We have all the investment memos that CapitalG has ever written. We have the data of how all our portfolio companies have performed. And the job of an investor is to look at for each new opportunity the data so far — the job of a growth investor — and you have some amount of data but a huge part is your intuition and your bet on what the future will look like. And it is amazing the tools that we've already built to be able to just ask questions — or hey, you know, did a company that had this type of net retention but this customer base, what can we learn from how other companies have scaled in the past? And of course you can't get too anchored on historical data, but you sure can ask more interesting questions and have that data at your fingertips. So we're just getting started. Like obviously the easy ones in investing are getting quick looks at companies and deep research type prompts and being able to pull public information. Those sort of workflows have been in place for a while and really do make the job easier. But the much more interesting ones are around proprietary data and being able to have more thoughtful analyses on sort of the drivers of business outperformance and seeing what we can learn from that.

Jason Baumgarten\
\[0:47:25\]\
Oh, it's fantastic to hear. All right, let's do a quick speed round. Couple of questions. Favorite recent book that made you really think.

Laela Sturdy\
\[0:47:33\]\
Got quite interested in the Enneagram recently. So I've read this book that a friend of mine who's like a researcher on the Enneagram — she's amazing — recommended. Called The Enneagram Guide to Waking Up by Beatrice Chestnut. And it's super interesting. You know, as a leader, it's fun for me to think about the context that I'm bringing, like what are my patterns and the way that I see the world, how does that color how I interpret, you know, an experience and the same for different people on my team. So that's been one that has really made me think about my own growth and my own sort of noticing the patterns I bring to different situations and then thinking about team dynamics both within my firm and the companies I work with and, you know, how the lens with which others are viewing the work world.

Jason Baumgarten\
\[0:48:20\]\
Totally common leadership advice you actually think is bad.

Laela Sturdy\
\[0:48:24\]\
So I would say everything has to be data driven. That's like a thing that you'll hear all the time. And I disagree. Some things need to be data driven and often data is a really important part in the decision making process. But most inventors of the future rely a lot more around intuition and seeing a world that the data cannot yet perfectly outline or map. And those are the people, especially in technology, that really build the future and build the biggest outcomes.

Jason Baumgarten\
\[0:48:57\]\
Yeah. In 2006 we all would have invested in ringtones if we were using data to predict the mobile web. What single piece of advice would you give a younger you?

Laela Sturdy\
\[0:49:06\]\
I would say find the most inspiring people you can and hang out with them as much as you can.

Jason Baumgarten\
\[0:49:13\]\
That's good. That's good. A hobby or activity you do today that you feel totally in the flow.

Laela Sturdy\
\[0:49:20\]\
Basketball. Sorry. It's been the same since I was 10 and I still play now — I play with my kids.

Jason Baumgarten\
\[0:49:25\]\
I know now I worry about getting hurt too much for some of those things. One tech related product or service that you are personally loving and enjoying in 2026.

Laela Sturdy\
\[0:49:33\]\
I'm also going to say Lovable. I think for a non-technical person — I'm not a coder — but the amount of things that I can build now on Lovable is so exciting and I think it really is amazing to be at the frontier of how we're reinventing software.

Jason Baumgarten\
\[0:49:49\]\
Is there something fun you've built you want to share?

Laela Sturdy\
\[0:49:52\]\
I mean it's more for us — it's been internal tooling within CapitalG that have helped us, like again the access to data, decision making dashboards, insights. I'm working on a screen time app for my kids which — I'm not sure they're excited about — but that helps them know, check off certain things to get incentives before they unlock gaming time. So it's fun to find both sort of personal use cases and then use cases as a leader that can transform how we operate.

Jason Baumgarten\
\[0:50:24\]\
Well Laela, that brings us to a wrap. Thank you for sharing your insights, your wisdom, your experience on Fit Happens and I hope you have a fantastic rest of your day.

Laela Sturdy\
\[0:50:33\]\
Thanks for having me Jason, it's always fun to chat with you and I enjoyed the discussion. So see you soon and take care of those fish.

Jason Baumgarten\
\[0:50:41\]\
See you soon.