Which start-ups change the future?

Copy LinkIntroducing the idea of Pattern Breakers

MIKE MAPLES: Twitter started as Odeo. Lyft started as Zimride. Justin TV became Twitch. And I’d forgotten I was a shareholder in Twitch, and then it got acquired by Amazon for $970 million. And I’d noticed that 80 percent of my exit profits had come from pivots. 

REID HOFFMAN: Mike Maples Jr. has an iconic track record as a Silicon Valley investor. But he isn’t just content taking the wins as they come. He’s been on a quest recently — maybe endlessly — to explore why some start-ups change the future and others fizzle out.

MAPLES: I couldn’t explain why things were working and not working. You kind of misremember how it really happened. You can think you knew stuff you didn’t really know. And so the Genesis of the book was: I need to figure out if there’s something else going on here that I don’t understand. 

HOFFMAN: I’m Reid Hoffman, your host. 

As a veteran venture capitalist and co-founder of the seed start-up fund Floodgate, it’s been said Mike Maples Jr. has a “Midas Touch.” Think of a tech start-up that has reshaped your life in the last 20 years, and odds are he helped fund its early days. Now, he’s distilled lessons from decades of success into a new book. It’s called Pattern Breakers, and he joined me to share its insights for investors and entrepreneurs. 

Mike Maples, we’ve known each other so long that we’re leaving our walkers at the door and probably can’t remember exactly when that first Hobee’s breakfast was, but welcome to Masters of Scale.

MAPLES: Thanks. It has been a while. I think we outlasted Hobee’s or at least that one.

HOFFMAN: Mike and I first met at the Stanford outpost of diner chain, Hobee’s.

Copy LinkThe power of inflection points

HOFFMAN: Yes. We definitely outlasted that Hobee’s. Hopefully not all the Hobee’s, but I think we outlasted the one in town and country center. So let’s go into a little bit, this notion of an inflection point, the thought is, Hey, look, you can have good ideas, but if you’re going to create something that’s huge, you’re actually going to be identifying something that’s in an inflection point, and most often inflection points are talked about as technology, right? It’s like, it’s now AI. Give me some sense of how to think about technology inflection points. And then also how to think about other than technology inflection points.

MAPLES: Yeah. So, a big part of my theory is that the founders who have breakthrough start-ups, even if they change their idea, the idea embodies inflections. And the reason is that business is never a fair fight. The only question is who fights unfair. And so the default assumption is the incumbents will fight unfair.

The status quo has the advantage. And so the entrepreneur needs some mechanism to change the subject. You know, if your product can be compared to the incumbents, you lose. You want to force a choice and not a comparison. 

And inflections are the magical weapon that the founder has to do that. Right? 

An inflection would be like the iPhone 4S had a GPS locator chip in it that allowed people to locate people algorithmically for the first time. 

It’s a turning point either in a technology’s ability to empower in a new way for the first time, or it can be societal, right? So, for example, with COVID, it was against the law before shelter-in-place to do across state lines telemedicine visits. But, you know, with the shelter-in-place laws and with COVID, they passed new regulations that said that that’s okay.

So now all of a sudden the doctors and the patients had a reason to do something different. And ever since then, people’s attitudes towards telemedicine have permanently shifted, right?

And so you can’t unsee that once you’ve tried it. And so what you’re looking for is a turning point. That causes people to have the potential to think, feel, and act differently than ever before. And, you know, most people, when they talk about inflections, they talk about it in the negative sense. You know, Andy Grove used to talk about inflections as a threat to his core business.

But inflections are the weapon for the founder because they allow them to change the subject.

Copy LinkSeek ‘non-consensus’ insights

HOFFMAN: Yep. Another phrase that’s frequently bandied about in Silicon Valley is contrarian, but it’s right. And obviously, That’s also tied to identifying these inflection points, because it’s kind of like seeing a left where everyone else is going right, you know, kind of thing.

And that’s identifying an inflection point that’s particularly interesting. So say a little bit about how that contrarian but right also fits into identifying inflection. 

MAPLES: Yeah. So here’s why I like the word non-consensus better than I like the word contrarian. Contrarian is contrary to something. And so most people who say I’m a contrarian, I view them as a different type of conformist because they’re still reacting relative to how other people act.

It’s kind of like if I paint my hair purple and say, aren’t I cool now? Uh, I guess but like if I’m doing it just to get attention, I’m not really being innovative.

I’m defining myself relative to the other. And so what I like about non-consensus is most of the really great start-up ideas, when I talk to the founders after the fact, they almost feel guilty that they had a non-consensus insight. They came about it honestly. 

Non-consensus is: It’s independence of thought and mind; it’s pursuing something at the edge for its own sake because it’s interesting to you, because you’re obsessed by it, and you’re trying to open new fractals of knowledge that have never been opened before.

And so the other part of it that I find is non-consensus is: People often tend to say to these founders, why are you wasting your time pursuing this idea you’re so obsessed about? There’s no obvious return in it. But by definition, every breakthrough is undiscovered. It hasn’t happened yet. And so we can only discover breakthroughs if we explore the unexplored, right?

And so that’s the other part of non-consensus is the willingness to go down a rabbit hole of what you’re interested in for its own sake. And in doing so, you learn secrets about the future, right? Whereas I find a lot of people just want to be disagreeable for its own sake. That’s not what I’m getting at here.

HOFFMAN: 100%. The contrarian that’s interesting is when you go against a body of expertise, and you say, I think differently than this body of expertise for the following reason, which is essentially the non-consensus.

MAPLES: Yeah. And you’ve always been really good about this when you’ve talked about what a great founder does, right? So I’ve heard you talk before where you say, ‘look, when you have an idea, you want to have a smart person push back on your idea, and you want to seek out disagreement with your idea.’ But it’s not disagreement that’s valid because of who’s disagreeing. It’s disagreement because your vantage point on the future is better informed.

Copy LinkStress-testing inflection points

HOFFMAN: Yes, exactly. So give a little bit more about quality recognition of good inflection points. When do you know you’ve got one?

MAPLES: The term that I settled on was the stress test. And so I thought, okay, I could stress test an idea for the power of its inflections and the power of its insight.

So with a stress test, I can say, there’s some things that we need to answer here. The first is: What is the specific new thing? Let’s say somebody comes to me and says, ‘AI is a revolution. It’s going to change the world.’ I’m like, okay, I agree. What’s the specific new thing that’s an inflection? And they might say ‘LLMs,’ and I’ll say what specific LLM? When was it introduced?

Why is it not going to be leapfrogged next week, next month? So the first thing you want to know is what was the specific new thing? Was it a new law that was passed to enable telemedicine visits? Was it a new chip that was embedded in the iPhone?

Those would be examples. Then the second thing I ask in the stress test is why is it radically empowering and who benefits from the empowerment? So like in the case of GPS chips in the smartphone, a whole lot of people are going to have smartphones. And anybody who wants to be located potentially would benefit from that empowerment in real-time.

And then there’s a third question I ask, what are the empowerment conditions? So if the government outlaws GPS locator chips in smartphones, the empowerment will not be unlocked. And the more willing you are to stress test the idea, the more likely you are to get the timing right. Because timing may be the biggest risk of them all. And so by pinpointing that inflection and pinpointing the turning point, you massively improve your odds of being right about the future and your ability to change it.

Copy LinkFinding your big idea amidst an inflection point

HOFFMAN: Yep. I completely agree, obviously. And this is one of the reasons why I was excited to invite you on to do the podcast. So one of the things I think may be a useful thing to cover is how do you keep processing information? Like what sources of information? How do you think about it to kind of have your inflection theory current and accurate? What do you do? What do you think entrepreneurs should do? You know, what do you read? Who do you talk to? That kind of stuff.

MAPLES: Yeah. So in this way, I’m a little bit like a train spotter, but for start-ups. So we, at Floodgate, have this database of start-ups where you would have made more than 100X on your first check. And what we do is we create a time capsule. So we’ll say, okay, what did Shopify look like at the time you would have had to decide to do a seed round?

What was the pitch like then? What was the momentum of the business then? What inflections were discernible then? And, you know, what we’re trying to do with that is, first of all, to figure out, is this theory a hoax, and is it screwed up, and can we falsify it? But the other thing that’s important is, just because you have an explanation for how something happens, it doesn’t mean that the signals are still easy to detect at the time, right?

So inflections might be harder to detect than authenticity of the founder to the future that they’re pursuing. I tend to believe that for the most part. And so then you say, okay, well, when we were looking at Shopify, or if you’re looking at Zoom, or if you were looking at Twitter in the early days or Lyft or whatever company, Airbnb, what is the signal that was really most knowable at the time?

So that’s, that’s for investors. I think that for founders, it’s more about, um, I’m pursuing something I think is interesting. How do I protect the ideas that seem dumb but might be good, or at least worth pursuing more, and how do I eliminate ideas that sound plausibly good that aren’t that good?

HOFFMAN:  So you’ve done this detailed analysis about what are the things that you would learn from seed investments, you know, in a whole wide variety of interesting things. What are those tips that you might offer without asking too much secret sauce from one VC to another?

MAPLES: Yeah. So yeah, it’s interesting. So I’d say that the first thing that I’ve noticed is that you can’t get too attached to the product for what it is. And so time and again, the product that ends up winning is not the product that you see when you’re doing a seed investment. Yeah, that was true of Twitter. It was true of Twitch. It was true of Lyft. So I’d say that the first major secret that I learned is that a great founder with a great insight that harnesses inflections has a first-mover advantage into the future. And even if they’re wrong about their initial implementation, they have the opportunity because they’re learning from other people in the future, to navigate the insight to the right product idea. And so time and again, I’ve seen that happen. And a good founder will figure out how to do that. And so where does that lead you? It leads you down a path of saying: what matters more is, are they a more authentic fit to the future that they’re pursuing?

You know, are they more likely to notice things that others won’t notice? Are they more likely to persuade people to be early believers in what they’re doing? Those things matter more than. The features and benefits. And are they landing right now with the product? That’s different in later stages. But I think in the early stage, in the seed stage before there’s any data, I think you’re investing in two things, the power of the insight and the capabilities of the founders and the authentic fit that they have to that future.

Copy LinkThe power of living in the future

HOFFMAN: Yeah, but one of the things you’re reminding me of, you may know this quote from one of my favorite science fiction authors, William Gibson, is: ‘the future is already here. It’s just unevenly distributed.’ And obviously you partially see that that insight is you’re looking for the founder that’s on the insight of the future is already here, just unevenly distributed.

MAPLES: I 100 percent agree. And so I look at it like there’s a bell curve of where people live. Most people live in the present, you know, and then some people live in the past, right? Some people live in the future. And metaphorically, I think what happens is when you’re living in the future, you’re at the extreme end of the bell curve, and these inflections come over like an event horizon, and you see them first. And so you’re more likely to stumble into some fundamental insight about the impact of those inflections. And so that’s what I find is, like, most people have the wrong idea about what vision is. They think vision is having better binoculars and seeing farther, right? But it’s more like I’m getting my hands dirty and what’s new about the future. I’m living in the future before other people do. And this is why I called the book Pattern Breakers — like, I see firsthand the new ways of thinking, feeling, and acting afforded by these inflections that will allow me to convert the prior pattern of doing things into a new pattern.

HOFFMAN: One of the funny things is you and I both know a bunch of VCs in Silicon Valley who are like, I’m a pattern matcher, you know, and I actually prefer your jujitsu, having turned to pattern breaker, because I think that’s part of living in the future. Say a little bit of more about the kind of pattern matchers and pattern breakers as a mindset. What does adopting the mindset look like?

MAPLES: Yeah, so the human mind is a pattern-matching system. And it’s a good thing that it is because it’s the thing that told us when you hear a saber tooth tiger roar to run the other way, or when it’s really cold outside, get inside the cave.

So we are wired to match patterns, and we’re also wired to match patterns because they help us fit into society, and they help us advance in society when we get good grades or achieve things or achieve status.

So pattern matching isn’t bad. The problem, though, is that it introduces a bias. And so, you don’t see the thing right in front of you. Most people, when they saw the iPhone 4S, didn’t realize that the thing in their hand or in their pockets could change the future, but the Lyft guys and the Uber guys did.

And so the pattern breaker says: If I’m an entrepreneur and I want to create a breakthrough, I have to break the pattern because humans are creatures of habit, and humans who are creatures of habit are going to consume from the incumbents, and they’re going to buy into the rules of the incumbency.

And so I have to break the pattern in order to escape the gravitational pull of the present, right? And so, I like to say great start-ups have to force a choice and not a comparison.

If everybody likes your start-up idea, that means it’s too much like what’s already there, which means it’s not radical enough. And so you want an idea that polarizes people that’s terrible; to most people, are not so good, but a few people are like, ‘Oh my God, where have you been all my life? This is amazing.’ And so to me, that’s what a pattern-breaking idea feels like.

Copy LinkCreate a movement around your idea

HOFFMAN: So, we also have this notion of movement versus go-to market. Say a little bit about that.

MAPLES: Yeah, so, one thing I noticed. And I wish I could say that this was smart. It’s more trial and error. And it’s like, why didn’t we say yes to that start-up? Let’s go back and see what we missed, right? 

And so what a lot of these founders do is they don’t market their start-up in a traditional marketing sense.

What I find is that the great start-ups very often are more like social movements. So if you look at a movement, typically, a movement has a minority of people who feel a sense of grievance with the status quo majority. And that minority of people wants to change the future. And they don’t want to change the future just for utility reasons or for business reasons. They want to feel a sense of transformation in their own lives and in society. 

Movements have this quality where you find early believers. Those early believers start to accumulate. But those early believers co-create the future with the founder of the movement.

And so for example, Airbnb, which I foolishly passed on, I noticed that Airbnb was a movement. Because a movement takes the greatest perceived strengths as a status quo into weaknesses, i’s a judo trick, right? So Four Seasons is the same in Paris as in Austin, Texas, as in San Francisco.

If you want to have that awesome experience that they bragged about for decades, great. But when you’re in Paris, wouldn’t you rather live in a 17th-century bungalow on the left bank for the same price? And when you’re in Austin, wouldn’t you rather live like a Texan? 

Rather than say Four Seasons hotels suck, they say, ‘hey, you have a choice.’ You can’t compare Airbnb with Four Seasons. It forces a choice and not a comparison, but like either live in the future we’re describing or don’t, and it’s like that was the brilliance of Airbnb, and I started to realize time and again a lot of these start-ups were movements.

HOFFMAN: Still to come, I talk with Mike about why he thinks AI is more than an inflection point — it’s a sea change.

[AD BReAK]

HOFFMAN: Welcome back to Masters of Scale. You can find this interview and more on the Masters of Scale YouTube channel.

Copy LinkWhy start-ups are poised to disrupt in this AI inflection point

So obviously, one of the things that’s all the rage these days, in Silicon Valley is artificial intelligence. There isn’t, I don’t think, a start-up that’s being pitched these days that doesn’t say ‘we’re the AI for…’ And, you know, it could be as absurd as ‘we’re the AI for reinventing ice cream.’  What do you make of the current AI tsunami? 

MAPLES: So occasionally you get something even bigger than an inflection. I call it a sea change. And when you and I were young, the first sea change in our lifetime was probably, I call it, the era of mass computation.

You wanted a computer on every desk at every home, hopefully running Microsoft software if you were Bill Gates. So then, in the early 90s, you have this era of mass connectivity. And rather than a computer on every desk in every home, you’re trying to connect all the nodes in the world, and you’re trying to create network effects between them, and you’re trying to capture their attention.

And so now, I think that we’re heading into the era of mass cognition.

I think that’s the sea change. And so what I’ve been trying to figure out is, what are the types of units of cognition? You know, is it predictions? Is it classifying things? 

And so then you start to say, okay, in what cases does the incumbent have an advantage in that world? And in what case does the start-up have an advantage in that world?

I have to believe a start-up will have an advantage in that world because the next wave or the next sea change is always counter-positioned in some way to the prior one. And it’s the counter positioning that if people think about insights from technology, but it also matters for the business model. And it’s that counter-positioning that affords the opening, right?

For these new companies to come in and disrupt everything. Change the rules. And so that’s what I’ve been spending a lot of time on when it comes to AI.

HOFFMAN: I like your use of the word cognitive because part of how I’m trying to get people to wake up to this is I call it the cognitive industrial revolution.

Copy LinkWhat AI start-ups are struggling to prove right now

MAPLES: Yeah. I wish I had it all figured out, but the first thing I’ve noticed is the AI start-ups that pitch me. Much more often have inflections than insights. And so I get pitched by start-ups all the time where I’m like, I can totally see why people will want this.

I could totally see why it’s empowering. I would want to use it myself, but I don’t understand why Sam Altman’s not going to have a demo in 90 days that puts you out of business.

And so I’ve seen the AI start-ups struggle to articulate the fundamental insight that they have and the true advantage that they have that’s structural.

Copy LinkMike & Reid’s nonconcensus views when it comes to AI

HOFFMAN: What are some of what you would think of as your non-consensus views around the current AI tsunami? And I’ll share some too.

MAPLES: I’d say my biggest non-consensus view is just that I believe that start-ups are going to have a huge opportunity here. And I think a lot of people are saying that this is one of those waves where the incumbents have the upper hand.

This reminds me a lot of the early days of the internet. You know, you have companies that are overfunded that probably won’t succeed. You have sort of hype cycles, and pretty soon there’ll be some troughs of disillusionment.

I think we’re kind of in this five-year window where it’s not completely obvious where to play, just like it wasn’t completely obvious in the first five years of the internet, but all my instincts tell me that it’s going to be massive for start-ups. How could it not be?

HOFFMAN: Yeah, my instincts are the same. People say, well, it’s all about the size of the model you’re training. So it’ll be OpenAI, Google, Microsoft. You know, and that’s it. And you’re like, well, no, actually in fact, there’s going to be a lot more than just the size of the model you’re training. There’s distribution, there is, you know, taking risks. There’s new patterns of development. There’s all kinds of things which you’re looking for inflection points. I’d say my probably non-consensus point that I’d add to the one that you’ve mentioned, I’d say that people are not sufficiently generalizing from what these things are as language amplifiers.

And, they kind of say, ‘well, yeah, sure. It writes memos, responds to emails, you know, interesting questions about what happens with search, etc.’ But they’re not thinking about the other patterns of language. What does it mean for biology? There’s relatively few that are doing, you know, biology and medicine, drug discovery, that kind of stuff.

And a lot of people can put wrappers on GPT4. So, you know, that kind of rare uniqueness of the idea I think is still, what are the areas in which this language device can suddenly create magic in areas that are not obvious to us? That’s another one that I’ve been noodling.

MAPLES: So I’ll try one more on you because I’d love to get your take on this. So the other thing I’m very intrigued by is how powerful simulation could be. Now I’m starting to feel like anything that can be simulated in the digital domain will. And, you know, any problem that could be completely described and contained within a digital description will — playing chess, driving a car, and, and, you know, biology is kind of interesting. Biology is really complex, but if you got to a place where you could simulate cellular behavior or things like it, you could imagine the drug trials that you could run on virtual people, virtual cells and yeah, that doesn’t mean that it’s safe, but like you could save so much time and cost if you could simulate things better, if you could eliminate a lot of bad options and lean into good ones. So I’m really interested in that. 

Copy Link“All professional activities will require an AI co-pilot”

HOFFMAN: One of the things that I believe with some vigor is that anything that we count as a professional activity today or yesterday will within three to five years, have an AI, you know, use the Microsoft language co-pilot. Because we as professionals always operate in language, whatever way that is, and you have a language accelerant in various ways.  But what do you think about that every single professional activity will have a cognitive amplifier, a co-pilot?

MAPLES: I agree with that, and it relates to this sea change idea. So when I think about an era of mass cognition, what if these cognitive agents number in the trillions? And what if now, like, okay, you’re answering your email, you have some ambient intelligence that knows, okay, if I get this Substack newsletter from this person, I like to read it, but I’d like you to go classify it, put it over here.

So I just don’t have to do any cognitive operations or load to do that. And so that’s kind of where I start to think about unbundling intelligence, right? You could say, human intelligence is a bundle of a lot of different types of intelligences in one person, but there’s no reason that you can’t unbundle those intelligences and have agentic behavior for those different types of things.

Now, if I want to market to Reid Hoffman, I’ve gotta market to Reid agents. I’ve gotta care what your agents think because they might be a gatekeeper, and I have to convince them that it’s in your interest to engage with me before you’re gonna engage with me, and all my instincts tell me something like that’ll happen.

That will be, you know, PR in the future will be: what does ChatGPT think about this? Right? Maybe it’s the most influential person in the world. And so I think that we’re gonna see more and more of that as well. 

Copy LinkLightning Round: Example of a big pivot?

HOFFMAN: Before I let Mike go, I had a few more questions for him — a sort of lightning round — that I hoped would give us some insights into how he works. 

Do you have a favorite specific example of a start-up that changed focus drastically?

MAPLES: Odeo. They started as a podcasting company a week after they announced that they were starting. Apple decides to give podcasting away on iTunes. Ev Williams tries to turn it into a business anyway, has a brave face, decides after a year and a half, he can’t make a go of it. And just totally by coincidence, Jack Dorsey is working on this thing that they’re going to call TWTTR or voicemail 2.0. 

HOFFMAN: Jack Dorsey was an engineer at Odeo … which became Twitter.

MAPLES: And the reason I like that example is you can’t really say that was a pivot based on learning from customers. That was just like trapping lightning in a bottle inside of a company that wasn’t working. And I can’t explain it any other way. So I like that example.

Copy LinkLightning Round: Books everyone should read?

HOFFMAN: Which is also one of the reasons I missed the early investment, because I didn’t invest in Odeo, but by the time they were going with Twitter, it was already gone, and I’d missed it. So what’s one book besides Pattern Breakers that you think everyone should read?

MAPLES: Oh, there’s so many, but okay. One would be The Top Five Regrets of the Dying by a woman named Bronnie Ware. She was an Australian hospice nurse, and she would spend time with people in the last 90 days of their life. And she asked, what are the things that you regret?

And she would have a chapter on the regret from the perspective of somebody who dealt with the regret. I wish I’d been more authentic. I wish I’d lived life according to my own terms. I wish I’d expressed my feelings more. I wish I hadn’t worked as hard. And then they would have the person who did the right version of that and, you know, came out on the other side of it.

And I find that it’s good every now and then, and I don’t mean to be morbid about it, but it’s good to remind yourself that it is going to end. And so, you know, when it ends, did you honor the gift of your time, and are you mindful about maybe the ways you’re not honoring the gift of your time?

And so I really, really appreciated that book a lot. That was a good one. The other one that I like is a totally different field: The Seven Powers by Hamilton Helmer. I think it’s one of the better books on competitive strategy that I’ve read. Everybody should read it. So I think it was good. The Art of Thought by Graham Wallace, the founder of the London School of Economics, written almost a hundred years ago, is a great book on understanding the mindset that the most creative people in history adopted.

So he studied people like Isaac Newton and Albert Einstein and Picasso and tried to understand, is there something these people do different from most people that causes them to come up with breakthroughs? And if I’d had more time with this book, that was the topic I was going to tackle, but I just decided I don’t have enough expertise.

I’m not a neuroscientist, right? I’m not, I’m not an acknowledged enough expert to really tackle it yet.

Copy LinkLightning Round: Homework for entrepreneurs?

HOFFMAN: If you could give an entrepreneur who’s just getting started one piece of homework, what would it be?

MAPLES: Pursue ideas where you are intrinsically motivated for its own sake. Because the great ideas and the great breakthroughs can’t be planned.

Think about something that you’re obsessively interested in all the time at the frontiers of knowledge. And that’s the unlock for unlocking the fractal of new knowledge and insights. But there’s no recipe. There can’t be one. Don’t look for one because it’s wrong-headed to even ask for one.

Copy LinkLightning Round: Mike secret power?

HOFFMAN:  What is the habit that has helped you succeed the most?

MAPLES: Optimism. And it’s probably helped me fail the most in certain circumstances. But I would say that, like, I tend to show up in the world as an optimist, and I tend to show up thinking there’s always an answer, that every problem has a solution. There’s always a way through, you know, it’s only over when you decide to quit.

I’d say that’s important. The other one is a lesson I learned from my dad that I wish everybody had had the privilege of learning about, which is: do your best. And so, ‘do your best’ to many people is an aphorism. But what I’ve come to realize is there’s only one you, and everybody in the world has a set of comparative advantages because there’s only one you.

And so, ironically, the best way to compete is not to watch what everybody else does. It’s to understand how to show up in the world to be your best self. It’s to understand how to honor the gift of your time as only you can honor it. And so, if you do your best, you may not always be the best, but you couldn’t do any better.

HOFFMAN: Yep. Amen. And actually reminds me of why I wrote my first book, The Start-up of You.

MAPLES: Yes, exactly.

Copy LinkLightning Round: Who do you talk to when you’re stuck?

HOFFMAN: So when you’re feeling stuck about a big decision, who do you talk to?

MAPLES: Oh boy. It depends. I used to talk to my dad a lot. We haven’t caught up as much in recent years, but at Web 2.0, you were definitely high on the list. You know, there’s a coach that some people know about in Silicon Valley, Matt Mochary. And the thing he does so well is, he’ll sit you down, and you’ll talk about something, and he’ll highlight the issue that you know is the issue.

You need to get off this board, and I’m like, ‘ah, man, I don’t want to ask this founder. He’s going to feel bad, blah, blah, blah.’ And Matt will say to me, ‘okay, when we catch up again in a week from now, are you willing to commit to me that you’ll have talked to that CEO and asked if you can get off that board?’

And I know that when I talk to him next time, he’s going to kick my ass if I haven’t done something. And I know he’s right to, right? So I’m like, shit, I don’t want to have this conversation, but I feel even worse about being a wuss so that I have to explain to Mochary a bunch of excuses that he won’t even believe that he shouldn’t believe.

So Matt is really good at sort of getting you to do the thing that you just don’t want to do for whatever reason, but he just won’t, he just will not give you even an inch of latitude in not doing it.

Copy LinkLightning Round: How would you like AI to change your future?

HOFFMAN:  It’s essential to have people like that in life. So last question, how would you like AI to change your future?

MAPLES: I would like it to find a way to let me live longer. You know, I don’t want to live forever, necessarily, but there’s just so much to know and so many interesting things to do in life. And, you know, as I get a little bit older, I realize how many things in this life are going to be constrained from you to ever be able to really do.

And so, man, it would be nice to have just more time. to try more things, explore more careers, you know, just try on different ways of showing up in the world and maybe find other ways to help people or learn from people. So I’d say if it can do that, I’d be a fan.

HOFFMAN: Well, great answer, Mike, thank you for joining a Masters of scale. I always love talking with you.

MAPLES: Me too, Reid. 

HOFFMAN: Mike’s new book Pattern Breakers is truly a great read. I’ve always appreciated how he approaches investing with an optimism about the future. The life and outlook of Mike Maples Jr. demonstrate that no matter how much success you’ve had, there are always benefits when you interrogate your past experiences and learn from them. 

I’m Reid Hoffman, thanks for listening.