Ep. #29, Game Theory with Leslie Fine

Rachel Chalmers: Today, I am delighted to have Leslie Fine, on the show. Leslie is one of two managing partners at Enjoy The Work, a unique startup advisory firm that helps founders become great CEOs.

She holds a PhD in game theory and behavioral economics from Caltech, which shapes her strategic approach to leadership and decision making. A seasoned startup veteran, Leslie founded led four startups before joining Salesforce as VP of product where she launched the company's first AI product.

In 2019, she left Salesforce to help run Enjoy The Work, a firm that has supported over 165 startup CEOs on their journey to becoming better leaders. Leslie, thanks so much for joining the show.

Leslie Fine: Oh, it's such a pleasure. Thanks for having me.

Rachel: Let's talk about game theory and behavioral economics. How, if at all, have they informed the decisions you've made in your career?

Leslie: Yeah, and I thank you for this question because I hadn't given it a lot of intentional thought until you posed that.

You know, my first exposure to game theory after deciding it sounded like a neat thing to study, was through a man named Peter Ordeshook at Caltech. This is a professor whose side hustle was writing constitutions for newly formed Eastern Bloc countries.

Rachel: Wow.

Leslie: And yeah. It was a good side gig. On the first day of my very first game theory class, he said, "You're all about to go insane." And then he went on to explain that the definition of insanity is seeing the same thing everybody else does, but seeing it completely differently.

And that's what game theory has done. It's rewired my brain to see the world as a game, to see everything, whether it's cooperative or competitive, as a dynamic between people who are maximizing something.

I then went on to study something called Mechanism Design. Are you familiar with that?

Rachel: I am not.

Leslie: So you are, but just not by that name. Mechanism design builds on game theory. And takes the idea that people act strategically in their own best interest and then uses that to shape the rules of the game itself, so that when people interact with it, what's good for the system happens. Right?

This could be anything from how entry to an event is conducted to how taxation works, to how performance reviews in your company work.

Rachel: I can see how this informs Constitution design.

Leslie: Oh, absolutely. And auction design and politics and so many things.

Rachel: You're aligning the incentives to get the outcomes that you want.

Leslie: Exactly. And you know, in short, don't hate to play. I hate the game. People are just doing what they think is right. And what I don't want people to think 'cause when I say self-interest, that sounds selfish.

I think one of the cool things that's happened in economics in the last 20, 30 years now is that we've realized that the notion of rationality doesn't mean economically maximizing in a monetary sense. It can include altruism. But we are all maximizing something.

Rachel: Yep.

Leslie: So I think there's two ways in which that's informed my current work. One is the way I think about organizational design. So, you know, the structure, the incentives, the autonomy that CEOs create within their culture drive the company.

You and I both know that the people don't work at startups for the salaries, the benefits or the great hours. They work at them to achieve autonomy, mastery, purpose. We want to know the rules of the game so that we can maximize how well we perform in it. And so bringing that mechanism design thought to how you think about your culture has made me realize culture's not a nice-to-have. It is essential to maximizing the outcome.

What game theory forces you to do is think and decision trees. And what that means, and this is where my product background, I spent a long time as a product leader and my game theory background kind of come together, is that it means you're always working backwards from something and then you're working your way up the decision tree and the probabilities and how you can affect that.

And so when I work with founders, one of the first things I ask them is, what are you working backwards from? Because every company is working towards one of four possible objectives. They're either working backwards from a fundraise and exit profitability, or God forbid, a wind down.

And once you have agreed, which one of these are we working backwards from right now, now we can start talking about what needs to be true today in order to get us here. And that drives your roadmap.

It drives your milestones, it drives your goal, it drives the game that we were just talking about. And it lets you align whatever it is you're working on today with the long-term goal you're working backwards from.

Rachel: You're right, I did know this by another name. I counsel a lot of founders who have never raised any venture yet to think really hard about whether they ever want to do raise venture.

And we talk about, you know, you have a profitable business, which is a nice lifestyle business, and you can have a really happy life that way. As soon as you raise venture, you are optimizing for an exit. And that's a different path.

Leslie: Yeah, people tend to think, and I see this all the time, even in later stage founders, that fundraising is a goal. Man, you just sold your com part of your company for probably less than it was worth, at least in your estimation of your outcome.

And so I counsel them instead to think of it as that is fuel. And the fuel is only useful if you understand that it's sufficient to get you to the next waste station for your rocket ship.

I confuse founders all the time by like, let's say they're a seed founder about to raise their A. One of the first questions I ask is, what do you think needs to be true to raise your series B? Assuming we're working backwards through that. And they're like, "Why the fuck are you asking me that right now?" I was like, "Cool."

Rachel: Because investors are thinking about it.

Leslie: Right. Are you putting enough fuel in your ship? And all of that is that work backwards mentality that I don't even realize I'm doing anymore and it was just beat into me by four years at Caltech.

Rachel: Tell us about the AI product that you shipped at Salesforce.

Leslie: Yeah, that was a really fun time at Salesforce. I joined in 2015. The four years speaking of rocket ships, the four years I was at Salesforce, we went from like 14,000 employees to 60,000 employees. Very dynamic time.

And I started as the VP of product where we called it data and analytics at the time. We didn't even call it AI, and I was in Marketing Cloud. And the reason Marketing Cloud made sense is frankly, they had the most data.

At the time, and I'm sure it's order magnitude more now, Salesforce sent 2 billion emails every single day on behalf of its customers.

Rachel: That's a lot of emails. I think they're sending them to me.

Leslie: Yeah, they are. You're welcome. The fact that they're arriving to you at the right time is my fault and I'm sorry. Yeah, each of those emails has dozens of pieces of metadata and so it's like a really deep pool to play in.

And we had just brought in house an amazing team from LinkedIn to sort of be the nucleus of what became Salesforce Einstein. And the data science and engineering team I got to play with.

We learned a lot about simplicity versus precision in that work. The first thing we built were propensity scores. And I know a lot of your audience will be familiar with the idea of a propensity score. It's not a probability. And I'll get to why that's important in a minute. It's how likely is someone to belong to a group that is likely to take an action, right?

It's one step disintermediated from a probability. But that's what we were building. We were building a propensity for someone to click on an email to make a purchase, to unsubscribe, and we would publish that.

And our customers are like, "Cool, you know, Rachel has a 75% probability of unsubscribing." And they're like, "Oh, that's not quite true." And I got super hung up on the fact that that wasn't quite true as opposed to simplifying so that the average person could take an action on it. And the fact that I was right didn't matter.

So that was lesson one. And we eventually wound up building it as sort of a set of speedometer like dials. It made it much easier for marketers to actually act on the data.

The second thing we shipped wasn't AI at all. It wasn't machine learning at all. It was counting at scale. But man, this was another lesson in impact over fanciness.

We built a product called Send Time Optimization. And all this did very fancy name was it ingested all of your behaviors about when you tend to open emails and built a 24-hour histogram for the marketer.

So when they sent their batch email, it dropped into each individual's email the hour that they were most likely to check their email because we look at the things at the top of our inbox more.

Rachel: Yeah, it's true.

Leslie: It's counting at scale.

Rachel: Right.

Leslie: It's not AI, but these were the two sort of gateway drugs into building more sophisticated AI products at Salesforce. And we got way fancier over time.

And are now, you know, they're doing some really true deep AI and we hired a ton of amazing talent into Salesforce, which is actually how I wound up doing what I do today. If you know your Salesforce history, we got deeply acquisitive in like the 2017 to '19 timeframe.

Rachel: Oh yeah.

Leslie: I became very involved in the data and product side of M&A, wound up as the sort of concierge for one of the larger deals we did a company called Krux. And that experience reminded me how much I was aligned with the entrepreneurial journey.

Rachel: Right.

Leslie: And I wanted to support that world, but man, I didn't want to start another company. It's terrible. You all are really brave. And I wasn't excited about the venture side of the table, just not who I am.

And I decided what I wanted to do was make the journey a little less lonely and leverage the mistakes I'd made and call them wisdom. And so that's how I wound up doing what I do.

Rachel: I mean, you're right, the founder journey is brutal and at both Heavybit and Generationship were investing in technical founders. And there's this enormous learning curve from great technical founder to genuine leader of an organization.

What do you see as those stepping stones? What do people have to learn as they make that transition?

Leslie: Yeah, you know, if you ask someone what makes a great founder? Well, Rachel, what do you think makes a great founder?

Rachel: What a good question. Turning the tables on me on my own podcast, this is outrageous. That's the kind of moxie I look for in a great founder. I do think I spent a lot of time looking for founder market fit.

I think great founders are people who have the potential to be the world expert in a particular customer problem. I also look for charisma.

I'm looking for people who can have a contrarian point of view, also defend it in the marketplace of ideas. People who can get up on a stage and be interesting and provocative and thoughtful. So those are two of the traits.

Leslie: Yeah, I couldn't have planted that better. Being a founder of state of mind, you just said it, right? Charisma, seeing the world in a different way. It's about seeing a white space in the world and like relentlessly pursuing it. It's willing something to existence that didn't exist before.

Now, man, being a CEO is an entirely different game, right? It's a set of learned skills. If you've met a great CEO and I know you have like, they can manage a board, they can operate a company using a financial model, they can scale a culture that people want to belong to and they can run a great fucking meeting, and a number of other skills, right?

But we have this Superman myth that just because you can will something to an existence, you can know how to run a company and that's just not true.

Being a founder's a gift and being a CEO is simply a craft and you can learn it.

So, I mean, that's how you think about it generally. And then, you know, as I was preparing to chat with you, I was thinking about where I see the failure modes for technical founders in particular.

Rachel: Yeah.

Leslie: So we have this playful way of categorizing CEOs at enjoy the work. There's a bunch of archetypes. And the one that I think I see most often for technical founders is what we call the robot CEO.

This is the founder who believes that emotions shouldn't exist in a startup. They think they can surgically cut out inconvenient emotions and keep everything else running smoothly. But here's the reality. Emotions are messy. Humans have emotions. Startups need humans. Therefore, startups are messy.

If we ask people to bring all of their emotion and all of their passion and all of who they are to work, but only in ways that don't create emotional friction, we're asking them to be this sort of half sterile robot, and that's going to create a cauldron that is going to explode. It just doesn't work. People are messy.

Rachel: That's a generative idea in so many ways. I mean, I'm obviously familiar with the robot CEOs and I think this is where you get these billboards that we're seeing in San Francisco, which say, "stop hiring humans."

And it's like, fine, you can staff your startup entirely with AI agents, but guess what? If you want to sell stuff, you're going to have to at some, point sell to a human. So even if you can like create your startup entirely full of robots, it must function in a messy human world.

Leslie: Yeah, you know, the stop hiring humans, and I know we'll talk more about, you know, the panacea of AI in a minute. The phrase I use when I'm talking to my founders about where to not hire humans is if you would ever in the past have filled in "what I need is a team of," then that's an interesting place.

Oh, I need a team of BDRs, I need a team of JavaScript engineers. Cool. But early days in startups are not those, right? These are generative humans. And it kind of dovetails nicely into another failure mode I see for technical founders, if you'll indulge me.

Rachel: Of course.

Leslie: And I was guilty of this, being a relatively technical founder. Many of us view anything outside of the tech and product corner of the company, in particular, sales and marketing, as fluff. That anybody can do, that doesn't have any science.

Go-to market is a science. And the technical CEOs that can take what they think of as rigor and apply it there will do well. And the ones who dismiss it and dismiss the people they put in those chairs will fail over and over again and they'll just keep hiring and firing people in sales and marketing because it doesn't land for them.

But if you can make the shift to the fit fact that this is a rigorous science, technical founders can do really well at go to market. Because if you give them the recipe, "Hey, can you take the time to crisply define your ideal customer profile, your ICP? Can you write down exactly the problem it solves from them and what their alternatives are and build a positioning statement?"

"Can you clearly define the stages in your go-to-market motion and the exit criteria? And can you design rigorous experiments and hypotheses and test them?"

Early go-to market is a science, and if technical founders can stop dismissing it, I think that they could actually be great at it.

Rachel: This is what I tell people, business is an engineering problem. All of these are engineering problems and you can hack them. It's another reason why I actually genuinely like technical founders despite all of the problem areas that you've identified, is that once that switch does flip in their head, they outperform. They're very, very capable.

Leslie: Yeah, look, and everybody's greatest feature is also their greatest bug. So, you know, that's fine as long as you can kind of hack through how do you mitigate the bug and amplify the feature. It's all good.

Rachel: We have the strengths of our deficits and vice versa.

Leslie: Exactly.

Rachel: How does enjoy the work support your founders through that transition?

Leslie: Yeah, so quick aside about enjoy the work, I'm one of 11 partners. We've all built stuff, sold stuff, killed stuff. Most of us have been founders and CEOs ourselves. And so we are really acutely aware of that gap between being a founder and being a CEO.

All of our founders are venture stage. Sometime past the beginning glimmers of product market fit. There's somebody other than your mother who loves the thing that you're building and will pay for it all the way through to growth stage.

And what we do is first, we assess where the company is. We have this notion of company in rhythm. You've seen a company in rhythm, right? It's unmistakable. They have this ease, they can take a punch, they flow. And that's not magic. It's to your point earlier, engineering, right?

So we break rhythm down into roughly 10 components. Have you articulated your mission, vision, and values? And are they a part of your culture? Do you have a goal setting framework? I don't give a rat's ask which one you use, just use one.

Have you thought about your communication architecture? Do you have a financial plan that you actually use to run your business, not just that your bookkeeper owns? Do you have a hiring plan and a style of hiring that matches your culture and a financial plan? Yada, yada, yada, yada. I can go on and on.

So the first thing we do is kind of assess where they are against this and work to get them to, you know, at least a four or five out of five on our scale. The number of companies that come in like, "Yeah, I'm a four or five on anything." I'm like, "Let me see." They're like, "Shit, I'm a two."

So we do that and then, you know, as we're doing that, there's always the crisis du jour. So crises can come in both good and bad flavors. "Oh, I just got an inbound interest for M&A." "Oh, this giant company wants to partner with me and I haven't found product market fit yet." "Oh shit, I'm out of money sooner than I thought because of reasons."

There's always a reason. So we work with our companies every single week proactively to make sure they're in rhythm, help them see what's coming around the corner. We built a huge library of frameworks. So for most things that are coming, I'm like, "Here's a framework for that and notion, and then let's walk through it." And then we lean in heavy on the crisis du jour.

Rachel: It sounds really fun.

Leslie: Oh man, it is the best work I've ever done.

Rachel: Beyond external metrics, how do you know if a startup is running well? You know it when you see it, but what is that ease, that flow?

Leslie: Yeah, you know, and by external metrics, I'm thinking the lagging indicators that are in your board deck.

Rachel: Right.

Leslie: Some of what I was just talking about rhythm really comes into play when I meet with a founder and often, we'll meet with their extended leadership team as well.

If I were to, going back to game theory, if I were to lock everyone in a separate booth prisoner's dilemma style and say, "What are the top three things that are most important for the company right now?" I would get the same fucking answers. Right?

So the idea that we have clear alignment throughout the company makes a ton of sense. That when I look at their hiring practices, I see that there's a team doing the hiring.

When I dig into that team, I see that there's at least one person on it who only cares about what Amazon calls bar raisers or what I'll call a culture match. People who are just keeping the cultural walls of the company safe.

When I meet with those other team members and they use the word and the CEO uses the word "we" instead of "I" about talking about the company, this doesn't mean they're going to win in the market.

They could still not be building something that people want, but at least they're building the company that they need. As I think you know, more companies die by suicide than homicide?

Rachel: Yes. Yeah.

Leslie: So ensuring that the inner dynamics, that there isn't resentment with the board. The board plan, these companies are like, "I have a board plan, I have an internal plan." And okay, it's fine if they're a little bit different in ambition, but they are entirely different.

I'm like, "Oh, you all are fucked. First of all, you just can't hold that in your head. Second of all, you're lying to somebody."

Rachel: Yeah. Yep.

Leslie: So these are the kind of watch signs I look for.

Rachel: And the thing about companies that are in flow, even if they don't succeed in the market, they throw off like a generation of incredibly talented engineers.

The number of Linden Lab veterans that I've invested in is statistically anomalous. And Linden wasn't a perfect company by any means, but it had a very specific culture that encouraged a kind of autonomy that has created more founders than you would think.

Leslie: Yeah, the one that comes to mind for me is, I don't know, you're probably too young to remember Plumtree.

Rachel: I remember Plumtree.

Leslie: The number of amazing people that were at Plumtree, Plumtree didn't do that great but my God, they spawned a generation.

Rachel: Yeah.

Leslie: The other thing that happens when a company is in rhythm is they don't lie to themselves when it isn't going well.

Rachel: Right.

Leslie: So we're often asking ourselves like, what is the impact that we have on companies? And as you know, especially with small end, that's kind of hard to measure. I can tell you it's profound.

But I'm looking for the data and what we notice is that when companies are doing things the way that we would like to see them do, we limit the downside. Because a company and rhythm doesn't lie to themselves about the amount of cash they have.

They've thought well ahead in infrastructure we call the Magic Box Paradigm borrowed liberally from a gentleman named Ezra Roizen and a book of the same name to think about strategic partnerships well before you need to land the plane.

They have a strategy that they're working back, "Okay, gosh, now we're working backwards from landing the plane. How are we going to do this well?" "Oh, we don't want to do that. How are we going to navigate an inside round?"

One of the places we lean in really heavily is the dynamics of fundraising. Another place where I think technical founders kind of fall down is they don't realize that fundraising is a discipline and a science. It is a funnel like any other. It is a dance like any other. And it requires a level of empathy for your side at the table that many especially first time founders lack.

Rachel: Yeah, I see the eyes bug out when I talk about investor empathy.

Leslie: There's this myth that, oh, you're just a rich person with a checkbook. I'm pretty sure you have a boss called an LP that you're responsible to?

Rachel: I have many bosses called LPs that I'm responsible to.

Leslie: Yeah, you sold them on a mandate, right?

Rachel: I did. I did. We have an LP agreement. It's signed in blood.

Leslie: Yeah, it turns out founders don't get that. That is one of the many ways in which a little wisdom can be repackaged and help them not make the same mistakes I did a long time ago.

Rachel: The whole program sounds like a set of checklists that help companies achieve psychological safety.

Leslie: Ooh, I like that. I think psychological safety is necessary but not sufficient. So yes, that is true and that is definitely the soft skills of the stuff that we lean on on. But there's also a number of functional skills.

You know, especially if you're technical founders, they have no fucking clue how or when to hire a CRO versus a VP of sales versus an AD. They probably can't spell BDR. So how do you do that? How do you evaluate that human? That's a set of skills that needs to be learned.

They've probably never done a strategic deal. Who are the players in the room and how does it work? What does procurement at enterprise software even look like?

Rachel: Who are stakeholders and why are they important?

Leslie: Why do we care that there's a champion versus an advocate? Oh, that's not the same as the buyer. There's a blocker in the way. That game, there's skills here that they need to learn.

Rachel: So obviously, all of these person-to-person functions are going to be replaced by AI. Right?

Leslie: Possibly.

Rachel: How should CEOs and other executives be thinking about the AI platform shift?

Leslie: Yeah, you know, I think that one of the key things to think about and this kind of feeds into, I'll talk my book a little bit, one of my portfolio companies Workhelix. You know, what Watson and Crick did for DNA, Workhelix is doing for companies, and I promise this relates to your question, I'll get there in a second.

In the age of AI, everyone's talking about jobs going away. And I think that's the wrong unit of measurement. Jobs are a collection of tasks. Tasks are going away or being augmented or transformed. So if we start to not think about our job, but the tasks that can be decomposed, then it becomes a more nuanced question.

And that's what Workhelix does. If they have this taxonomy of tasks and can go into any company and figure out like, oh, here's the task exposure you have and here are the tasks that can be replaced and here's how you can reconfigure your workhorse.

So I want people to think in that lens, at least for the short term. There are a bunch of tasks that I do every day, Rachel, that can absolutely be replaced by an AI, but my job can't be.

So how can I decompose myself and think about where that can be replaced. And going to what I said earlier, if there's any place where I'm using the phrase, I just need a team of, that's the low-hanging fruit.

The number of companies, and I'm sure this is true for you right now, where five years ago, they would need 20 developers. They need three or four in one architect. I relate it to pre-AWS the amount of money needed to create a startup was massive 'cause you had to build a data center in your fucking closet.

Rachel: You had to buy a Sun E10K.

Leslie: Like so all of a sudden, your first half million dollars is out the door. Right now, I can buy compute for like $3. Great. Cool. It's the same thing, right?

Rachel: It is. It is.

Leslie: The amount of capital I need to experiment with something where I can throw, I just need a group of bodies has dropped like a stone. I also think if you think in terms of the theory of the firm, going back in my economics roots.

You know, companies exist to aggregate tasks to break down transaction costs between people. And as you bring more externalized bots on, you can start to deconstruct the firm and think of it as a smaller and smaller atomic unit.

Rachel: Obligatory shout out to Rosalind Franklin without whose x-ray Crystallography, Watson and Crick would not have won the Nobel Prize.

Leslie: Fair point, thank you.

Rachel: What are some other AI startups you're excited about other than Workhelix?

Leslie: So I really love, and look, I'm a product person, so I fall in and out of love with products on a daily basis. The other managing partner, Jonathan, will not really adopt a product until I continue to love it for at least a month. But the product du jour is something called Wispr Flow.

Rachel: Oh.

Leslie: Oh my God, I love Wispr Flow. You played with it?

Rachel: I have not.

Leslie: So what Wispr Flow does is the idea is really simple. It reprograms a key on your keyboard. For me, it's the function key 'cause I never use the function key, to be a voice recorder. And that's not that complicated. But what's amazing is how seamlessly they fit into the workflow.

So in any app, whether you're in Slack or an email or a Messenger or Google Docs, I don't care. You hit the function key or if you want it to be hold down, you hit function space and it records and it transcribes.

It also understands the context of the app you're using and the linguistic style you would use there. So the way it formats your transcription is far more formal in an email.

And it does things like if I say, "Hey, Rachel, there are three things I want to talk to you. Thing one, thing two, thing three." It's three things I want to talk to you, colon, bullet, one. So it tailors a formatting.

And what I love about Wispr Flow is kind of what I love about a lot of these products in general, it's not that technically complicated, right? They're using an off-the-shelf thing, but because they have figured out the flow of how I work, because some product person out there loved me enough to understand my workflow, it's now seamlessly part of my life.

Like AI doesn't have to be groundbreaking to have a massive impact. It has to meet people where they are so they can do what they do better.

So that's thing one. The other, I'll talk again from my book. I have this company, God, I love them. I love their culture. I love what they build. They're just amazing people. It's a company called Darrow. Darrow.ai. And what they've built, it's an Israeli company.

They've built a platform that uncovers hidden legal insights. So they take fragmented unstructured data and find pieces of the puzzle from all over the interwebs that add up to a litigable claim.

Rachel: Hmm.

Leslie: They started in privacy, they've moved into ERISA claims, environmental pollution claims. They're going into mass torts and what they do is they then package that up and go to law firms and say, they have a whole underwriting department. "Underwriting says this is a case and we'll sell it to you for X dollars and we'll keep a little bit of the tail."

And so what they're doing is finding entirely new legal insights that would've been impossible to uncover.

Rachel: Have you seen Better Call Saul?

Leslie: It is a little... Yeah, there's definitely some dark implications.

Rachel: Yeah, but Erin Brockovich as well. It's that kind of work.

Leslie: It is. And they are White hat men. Their mission statement for their company. I love it, it's just two words. It's, "Frictionless justice."

Rachel: Oh, that's beautiful.

Leslie: Is it like, I get goosebumps every time I say it. I love it. You know, so many other legal tech companies are about how do we make lawyers more efficient? And so I love that we're moving upstream to how do we discover wrongs that we can write.

Rachel: That's inspiring. What is some of your favorite sources for learning about AI?

Leslie: Yeah. You know, won't surprise you with the little bit that you know about me, but it's talking to people. It's also just lazy, like that them read all the things. And I get to talk to fascinating folks like you all day long.

As you learned with Wispr Flow, I care less about the cutting edge, coolest new LLM thing that has been built and more about how these are impacting our lives and solving problems and integrating and sort of meeting us where we are.

And so one of my standard prompts now is what's the most interesting AI tool you're using? So I did that at a dinner last week. And that's where I got Wispr Flow, I learned about NotebookLM and how a Stanford professor is using it to change the way he does research.

Circleback, which has become by far, my favorite meeting notes taker 'cause it understands business meetings. All of those I actively use and it's just from talking to other people. I think that the real innovation is making AI accessible, intuitive, valuable in the flow of everyday work. And so I get that by talking to other humans.

Rachel: Yeah. It's a tool. It's only interesting insofar as it helps humans do the work that they need to do.

Leslie: Yeah, it's like asking me where I learned about bulldozers. I don't know.

Rachel: From a toddler friend. If everything goes exactly how you'd like it to go for the next five years, what does the future look like?

Leslie: Oh gosh. I think you want me to answer that from an AI and technology perspective?

Rachel: I am very open in how I want people to answer this question. I think it says a lot about the guest, how they choose to take it.

Leslie: I'll give you three answers then. I'll do AI, my firm, and for me. I'm going to borrow liberally from a guy named Andy McAfee, who's written a bunch on this.

I think AI has the same potential to reshape the way we work that the industrial revolution did. Machines moved us away from repetitive manual labor so that we could work on other things. AI does that same thing for cognitive labor.

And as I mentioned, the outcome is in fewer jobs with fewer tasks. So we can focus on more creative, more purpose-driven work. So the idea of freeing us up to think about other things, and I know that feels scary, but I also believe we're going to find ways to fill our time and also, the deconstruction of the firm that we can do more with less.

That we do not have the same kind of friction and lock-in. That slows technological change because it's cheap and easy to spin things up will create companies that are leaner and more adaptive.

So for Enjoy The Work, I think we have, as all companies should, a kind of spiky point of view that's not fully adapted yet, that being a founder is not the same as a CEO. In the next five years, I hope that the way that we think about that becomes a common understanding and that investors will sort of encourage founders on the journey to CEO as opposed to browbeat or replace.

Rachel: Right.

Leslie: And see it as a craft that you master and that it's okay to get help in doing it.

Rachel: Yep.

Leslie: And then as a personal level, when you said five years, I have a senior in high school and I have one in college. So at five years, my youngest, God willing, will have finished college.

They'll be on their way to being happy, productive adults who are not draining my bank accounts. I'll be every bit as healthy as I am today, if not more so. And be able to do my work from anywhere in the world.

Rachel: That sounds amazing.

Leslie: I know, I'm pretty psyched.

Rachel: I mean, I'm really excited for being freed up from tasks because I have a sunny garden and a San Francisco public library card and I got a lot of reading to get through.

Leslie: Yeah, well maybe we'll get you a gardening robot.

Rachel: If you had a generation ship, a colony ship to Alpha Centauri, what would you call it?

Leslie: Yeah, I'm going to totally rip off a favorite show. I name it Serenity.

Rachel: Of course.

Leslie: Right? Not only to nod from the Starship Firefly where it's grit and charm, resilience and this sort of scrappy crew that found strength in each other and all that good stuff.

My LLC is called Iremia which is Greek for serenity. It's a word that captured something essential about how I aspire to show up. It is not easy for me. In fact, many years ago, a dear friend gave me a wish for that word. And it's something I've sort of held onto pretty tightly.

And that when I am at my most effective, it's because I am serene. It's when I can zoom out. It's when I'm thoughtful, it's when I'm present, it's when I'm in service to people. So that's what I'd send into the universe.

Rachel: That's your psychological safety right there, that's enjoying the work.

Leslie: Necessary but not sufficient.

Rachel: Leslie, it's been a joy to have you on the show. Thank you so much.

Leslie: Thank you.