In short
Lenny's Podcast: Product | Growth | Career
Episode
Pattern Breakers: How to find a breakthrough startup idea | Mike Maples, Jr.
Guest
- Mike Maples, Jr.: Founding Partner at Floodgate, early-stage startup investor with successful bets on companies like Twitter, Lyft, Twitch, Okta, Rappi, and Applied Intuition.
Key Topics Discussed
- Three Elements of Breakthrough Startup Ideas:
- Inflections: External events that create potential for radical change.
- Examples: iPhone 4S for Lyft, improvement in smartphone cameras for Instagram.
- Categories: Technological, Regulatory, and Belief changes.
- Insights: Non-obvious truths about harnessing inflections.
- Importance of being non-consensus and right.
- Power of surprises, exemplified by Chegg’s pricing strategy.
- Founder-Future Fit: Match between a founder's traits and the future they're building for.
- Importance of authenticity and living in the future.
- Pattern-Breaking Actions:
- Movements: Leveraging a grievance of a minority against a majority.
- Examples: Lyft’s ride-sharing movement, Airbnb’s "live like a local" ethos.
- Storytelling: Crafting a compelling narrative that resonates with early adopters.
- Framework: World that is vs. World that could be (inspired by Nancy Duarte’s storytelling principles).
- Disagreeableness: Willingness to be non-conformist and pursue an idea despite skepticism.
- Importance of being able to withstand being disliked and criticized.
- Applying Principles Within Companies:
- Pattern-breaking ideas require different leadership, risk profiles, and go-to-market strategies.
- Importance of creating autonomous teams to foster innovation (e.g., Skunk Works at Lockheed).
- Strategies such as investing in projects with asymmetric upsides and treating them as separate entities within larger companies.
Key Insights and Advice
- Mindset for Breakthroughs: Embrace surprises and non-consensus ideas. Live in the future to notice what's missing and build intuition about new markets.
- Startups vs. Corporates: Startups win by denying the present rules and proposing a radically different future. Corporates often fail in innovation by trying to integrate new ideas into existing structures.
- Persistence and Authenticity: Successful founders are often those who pursue ideas with personal passion and authenticity, even when faced with widespread skepticism.
Practical Advice for Aspiring Founders
- Get Out of the Present: Engage with cutting-edge technologies and future-forward thinkers.
- Identify Lighthouse Customers: Work with future-oriented customers who can guide product development.
- Force a Choice, Not a Comparison: Create unique value propositions that compel certain customers, rather than competing on traditional metrics.
Resources and Further Reading
- Books Mentioned:
- "Top Five Regrets of the Dying" by Bronnie Ware
- "Chase, Chance, and Creativity" by James Austin
- "The Laws of Human Nature" by Robert Greene
- "Resonate" by Nancy Duarte
- Pattern Breakers: Why Some Start-Ups Change the Future by Mike Maples, Jr.
Where to Find More
- Mike Maples, Jr.:
- [Substack](https://greatness.substack.com/)
- [LinkedIn](https://www.linkedin.com/in/maples/)
- [Floodgate](https://www.floodgate.com/)
- Lenny Rachitsky:
- [Lenny's Newsletter](https://www.lennysnewsletter.com)
- [Twitter](https://twitter.com/lennysan)
- [LinkedIn](https://www.linkedin.com/in/lennyrachitsky/)
Episode Highlights
- The episode provides a deep dive into the patterns and principles behind breakthrough startup ideas, offering valuable insights for founders and corporate innovators alike. The discussion emphasizes the importance of living in the future, embracing non-conformity, and crafting movements to drive change.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Transcript
Automatic transcript. May contain errors.0:00You found that there's basically three elements of most breakthrough startup ideas. The three are inflections, insights, and then founder of FutureFid. Business is never a fair fight. What inflections let the founder do is wage asymmetric warfare on the press. You referenced this term that you use occasionally this earned secret. The way inventions happen is people get their hands dirty, being awake to the possibility that secrets are there. If you're living in the future and you notice what's missing, you're intuition about what to build is far more likely to be right. This connects with that staff that you shared that 80 % of your biggest returning investments came from a pivot.
0:35So startup never beats a big company by executing better. The way startups win is because it proposes a radically different future, disorienting incumbent, and chaotically moves people to that different future. The rock is the inflection, the slingshot is the insight that David Schutz at Goliath were looking to create the conditions where we're going to get to play an unfair game by unfair rules that favor us.
1:00Today my guest is Mike Maple's Jr. Mike is a legendary early stage startup investor, and with his firm Floodgate, which was founded over 20 years ago, was one of the earliest pioneers of seed stage investing as a category. He's made early bets on transformative companies like Twitter, Lyft, Twitch, Octa, Rappy, and Applied Intuition, and has been on the Forbes Midas list eight times. More recently, he's been spending a lot of his time researching where great startup ideas come from, and what separates the startups and founders that break through and change the world from those that don't go anywhere.
1:35After spending years reviewing his notes and decks from the thousands of startups that he's met with over the past two decades, he's uncovered three ways that breakthrough founders think differently and act differently. In her conversation, Mike shares what he's uncovered, along with the pitfalls that he's seen many founders and startups fall into, how to apply these pattern -breaking principles to large companies, and so much more, I've never seen anything like this sort of research done before on early stage investing and startups. And if you're a founder, a product builder, or an investor, this will change the way that you think about building successful products.
2:09Also, as an added bonus, Mike has offered listeners of this podcast a very cool offer. If you pre -order the book at www .patternbreakers .com slash Lenny, you will receive a second signed copy of the book for free. There are a limited number of copies available of this offer, so if you're interested, I'd encourage you to place your order. ASAP, the book is coming out July 9th, so if you take advantage of this offer, go to www .patternbreakers .com slash Lenny. With that, I bring you Mike Maple's Jr. Mike, thank you so much for being here and welcome to the podcast. Lenny, thanks for having me.
2:48It's absolutely an honor. It's my honor. What we're going to be talking about in our conversation today is how to come up with a startup idea and how to take the first few steps to make that idea real. You have a book coming out that is exactly this, helping people understand to do this. It's called Patternbreakers. Why some startups change the future? Let me just ask a broad question. You're very busy, very successful investor. Why did you decide to write a book? Yeah, and like a lot of things in life, it was an outgrowth of an accident and an outgrowth of being down a certain rabbit hole. About 10 years ago, Twitch was acquired by Amazon for $970 million.
3:34We made something like 85 times our money. Normally, you'd think that's a really good thing. It was a good thing, but I had forgotten that I was even a shareholder. I had to go to my LPs and I had to explain to them, hey, I'm sorry, I don't have this in my financial statements, but do you want me to restate them? They were all like, no, we're good. Just send us the money. Some of them even sent me like bottles of champagne and stuff and the good kind. I started to feel a little bit unsettled because how was I shareholder in Twitch? I invested in a company called Justin TV that had morphed into two companies.
4:12Social cam and Twitch and then Social cam got bought. I just thought that was the company. Then I looked at, I'd been investing for about 10 years. I noticed that 80 % of my exit profits had gone from Divit. I also noticed that all the ones that had seemed to do well didn't necessarily follow the best practices that everybody talked about. I didn't see the Twitter guys doing the business model canvas, for example. I didn't see the Justin TV team even as they morphed into Twitch being who I would hold up as the most functioning management team I ever saw. A lot of it was pretty crazy and wild and random.
4:54At the same time, I was helping founders shut down their companies and they had seemed to do all the right things. They'd done the business model canvas. They'd done customer development. They'd done all the things you're supposed to do, hired well. They would have been a Harvard Business School case study, except for the fact that they failed. The genesis of this project was really like, okay, should I just retire before I get exposed? Is this just all random? Am I just lucky? Or is there something else worth understanding? As I started to develop conviction about what those things were, I started to talk to people about a lot of people said, oh, you should write a book, founders ought to see this and be really valuable for their thought process and coming up with their startup ideas.
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8:21You've looked at what is the work that went into this? Yes. There's a movie that came out a few years ago called Train Spotting. There's these guys, these dorky old British guys and anorak coats who chart the coming's goings of trains. It's the most interesting thing in the world. They put it in their journals and everything. I'm that way when it comes to startups. I have a database of any startup where you would have made more than 100 on your first check. What I want to do is I want to get a time capsule for those startups. I want to understand what did it look like not after it succeeded, but what did it look like at precisely the time you would have needed to decide whether it was an interesting opportunity.
9:05I have the original pitch deck for what was at the time called Air Bed and Breakfast, which I foolishly passed on. You seem to have made a good career decision in joining. I have the pitch deck for Pinterest. I have the pitch deck for all of these that we either passed on or said yes to. The reason I want to do that is it's easy to misremember how things really happened. What I find is even the founders themselves. We have a tendency to remember knowing more than we really did at the time. I really wanted to do the best job I could of understanding exactly what it was like. What was the origin story of this idea?
9:51How did they come up with it? If they pivoted, what caused them to pivot? When did they first start to encounter success? What was the reason for that? All those things. I had to be really careful in the questions that I asked. For example, you don't ask why were you successful? Then they'll offer their reasons they thought they were successful. What you want to do is you want to say, I noticed here is the seed pitch deck and you called the product X. Now the product is called why? When did you make that change? Why did that happen? You're trying to do the very best you can of asking a very non -judgmental set of questions that are going to give you a non -judgmental set of answers so that you can be like a detective and get to the root cause of why these things took off.
10:37Incredible. I think what's also important is you have access to more data and more unique data than most other people because you invest so early stage. I think the other thing is I just have a pretty sympathico relationship with founders usually and so I can push for the real. I'm not going to share anything. You don't want me to share. I'm just trying to understand. When you have these informal relationships, that's the other thing I learned is you try not to show up in a conference room interviewing them like a normal interview. You try to glean these facts over time with informal discussions and in the midst of talking about other things as well.
11:22I think that that was part of what was really valuable about the exercise was the opportunity to get the unvarnished wild story of what really happened. Amazing. Let's get into it. Your book's basically broken up in two parts. How to come up with an idea and then the actions you need to get right to move forward an idea and you have a really cool way of framing how to do this and then we'll get into it but maybe frame these two parts real quick. Yeah, so I'll give it my best shot. I mean, the main thing is that business is never a fair fight. So the incumbents start out with an advantage and the default is they will maintain their advantage.
12:05And so the startup has to decide that it wants to fight unfair. And so how does a startup fight unfair? It has to harness a different set of powers than are obvious to most people, right? So for example, better doesn't matter when you're a startup because better is an extension of the present. Better is when you think the future will resemble the present but only be slightly different. The way startups win is by being radically different. A startup wins by avoiding the comparison trap entirely. So like when when lift launched ride sharing and then Uber closely followed right with Uber X nobody after riding ride share said, oh, how's that different from taxis?
12:52Right, it was just self evident how different it was. And so like that's what what we mean by forcing a choice and not a comparison. So the startup capitalist, it turns out as a different type of capitalist, right? A corporate capitalist makes money by persistently compounding makes money by extending their advantage makes money by having a moat makes money by doing things well over and over again in a compounding way. Startup has none of those things. There's nothing to compound. And so the way a startup wins is they just change the subject. They deny the premise of the rules and propose something completely different.
13:34And that was the original notion behind pattern breaking was you want to have an idea that just radically breaks the pattern that can't be compared to anything that's come before. And that's when the startup has a chance to play offense. So coming back to the two parts are coming up with the idea and the actions that you got to take. So let's dive into coming up with an idea. And this is where I want to spend most of the time because I think this is where most people get it wrong or everything starts with the idea. So I think there's a lot of meat here. And what I love about your book is you have a very succinct limited number of things that you've uncovered that are elements across successful companies, pattern breaking companies.
14:14So within the idea bucket, you found that there's basically three elements of most breakthrough startup ideas. Can you share the three and then let's talk about each one? Yeah, the three are inflections insights. And then what I call founder future fit or another way I phrase it is, is this from the future. But those are the those are the main three things that I've observed tend to suggest breakthrough potential. And here's an important thing. You'll notice I didn't say the implementation, right? So one of the things that I learned is that if you have the right insight and we'll get to some of this, you have a first mover advantage into the future.
14:55And so a lot of times your first implementation won't be right. But if your insight is correct, you can navigate the implementation to the right implementation to get product market fit. And so, but what we need to understand is there need to be these underlying forces underneath the idea to give it the power to escape the gravitational pull of the present, right? That's what we want. We want a set of powers that we could adverb that make it worth pursuing and make it worth navigating the product to the ultimate plate. So let's talk about the first power. You call it inflections. What is an inflection?
15:30Why doesn't matter? What is an inflection look like? An inflection is an external event that creates the potential for radical change and how people think feel and act. Inflections happen external to any startup or any company for that matter. So we brought up a lift a little bit ago. So maybe we'll use them as an example. So the inflection that enabled lift was the iPhone 4S shipped with a GPS locator chip. And one of the things that that illustrates is, for example, Moore's law is not an inflection, you know, an improvement curve is not an inflection. An inflection, I'm a little persnickety about it's a turning point.
16:11And so, you know, in math, it's a turning point on a curve where the slope changes. But in tech startups, it's a point in time where something new gets introduced that creates new empowerment for the first time possible. And so, you know, people talk about timing and why now? Inflections for me were the unlock. You know, you could have, you could have had the idea for ride sharing before the iPhone 4S, but it wouldn't have mattered because the riders and the drivers wouldn't have been able to locate each other well enough. If you'd waited too long after the iPhone 4S, it would have been obvious.
16:46And so there was this window of time, this magical moment when a new type of empowerment was possible for the first time ever. And the companies that the founders who understood that were in a position to offer that kind of empowerment in the form of a radical product that changed the future to make it even more real for people. What are some other examples of inflections, either in the past and the present. Another example would be the cameras getting better on the smartphones, which enabled Instagram. So Instagram was at the convergence of a few inflections. First of all, there were smartphone adoptions, so they're just more of them.
17:24And so they crossed like 10 million smartphones. But then you had the cameras getting a lot better. You had more of them connected on Wi -Fi. You had the networks having better upload speed for smartphones. So all those factors converged and made it possible for Instagram to offer a product that was good enough to take most of your photos with. You know, you didn't start to think, oh, I need a digital camera, a separate from my smartphone. Now I can just use my smartphone everywhere I go. But Instagram could have come out in 2008. It probably wouldn't have worked. It probably wouldn't have worked to the extent that it did.
18:04It's window of timing was just right. What are some other examples? The locator chips in the smartphones powered other companies as well, powered DoorDash, Instacart. They had different insights, which we'll get to, right? But there were lots of different ways to harness that power. One thing I love about inflections and this kind of goes really old school is just because you have a power doesn't mean you know how to use it, right? So like the wheel was mounted horizontally for like 500 years before somebody mounted it vertically. So originally, people used the wheel to make pots. And that was a good innovation because it accelerated making pots.
18:49But then somebody decides to mount it vertically. And now they're now you're propelling wagons and you know, you just change transportation entirely. And so most people don't realize that the thing that's underneath us or the thing that's in our hands or the thing that's in our pocket might have a power that when unleash could change the future. And it's one of the very special things about founders that are great is they recognize they notice things that we don't know. All of us tend to just follow the patterns we've always followed because most of us tend to assume that tomorrow be similar to yesterday, but sometimes the founder will notice an inflection.
19:29And I find that kind of inspiring because inflections are all around us all the time, but most of us just don't just don't bother to look. You know, most of us are so busy going about our day to day that we don't notice the emergence of a new empowering thing right under our nose, right in our pockets, but some founders do. It makes me think about chat GPT when it came out. It was sitting on top of an existing model. And it just gave people a new interface to use it. And I'll send everyone crazy. They're like, oh my god, this is the future. But it was already there. It just you couldn't chat with it the way that people wanted to chat.
20:04Yeah, you know, like Michael Sailor once I was talking to him and he said, you know, the Romans could have invented the printing press a lot earlier. They had sandals that would make marks in the mud. You could have in theory drawn the connection between those marks in the mud, the ability to have movable type and letterpress, but nobody did, right? And so quite often, these inflections will go, they'll just go unrecognized for a while, but they're always there. Like they're always there. They're there. They're right now, you know, in the ambient atmosphere, there's somebody about to harness an inflection that most of us would just walk right by and never see.
20:44Wow. My mind is racing. What's out there right now? Obviously, AI is top of mind for a lot of people. I know you're stickler for what is an inflection? What does not do you consider AI in inflection? I would say that I would probably be a little more specific about it. So I might say that certain large language models are an inflection because like what when I think about an inflection and one of the one of the things I emphasize in the book is stress tests. So like it's funny. Founders never really come to me and say, hey, can you help me come up with a good idea? They would think they're weak sauce if they had to do that.
21:18So usually what's the more common occurrence is they'll say, I've got this idea. What do you think about it? And so what I can say to them is it's not my place to have an opinion, but like let me just ask you, does it embody one or more inflections? And if it does, there's a few, we could stress test that. We can say, what is the specific new thing that was just introduced? How does it empower people? How does it specifically empower specific people in specific ways? And under what conditions might that empowerment be realized and under what conditions might it not be? Because like nuclear power has existed for a long, long time, but we have it built in the nuclear power plants in 50 years.
21:59And so just because you have a power, it doesn't mean it's going to get used. It could get regulated out of existence. A customer's could decide they don't want it. And so we want to answer all three things. What's the specific new thing? What is the specific form of empowerment it offers into who? And under what are the empowerment conditions? So like with the flexion for lift, the inflection was the new thing was the iPhone for us with a GPS chip. The empowerment was you can locate anyone within one meter accuracy with an algorithm. And that's going to be pretty much anybody with a smartphone.
22:34And that's a lot of people. And you know, in order for this to be met, people are going to have to want to share their location information with applications. The government's going to have to not outlaw GPS chips. It phones, Apple's going to have to keep wanting to ship GPS chips and phones. And we felt like those were pretty reasonable bet, right? We felt like it's pretty likely those empowerment conditions. That's amazing. I was just going to ask for an example. You already provided one. What about in terms of Twitch? Was there was the inflection there? I think there were a couple at the first was the the shift towards user generated content and sort of internet celebrities.
23:13Justin Conne wanted to be an influencer before there was a term to describe it. Right? He was really built in the product that he wanted for himself. But you know, right before Twitch or right before Justin's TV, which was the original company, times person of the year had been you. And they had YouTube on the cover of the magazine. And so you had that was a major turning point in how entertainment was happening. But simultaneously broadband penetration had reached critical mass. You had the CDNs were getting really good. And we thought that they would get better. And so you know, you were in the situation where the conditions to live stream video for the first time broadly over the internet were being met.
23:57Whereas you know, you could you could have done that even two years before. Backed Kyle Vote had to invent some pretty miraculous stuff to even make it work when they did. But you could you could see how okay, once once video starts streaming on the internet in real time, that could be a thing, right? You could just see how that would be a thing if it if it worked. And so I'd say those are the inflect, you know, Airbnb company close to both of our hearts for different reasons. They benefited, I think, from a couple things. One was the proliferation of customer views online and people's trust of reviews as a substitute for trusting the brand of the hotel.
24:34But then also Facebook connect made it possible to pass people's profile information. And so the guest in the host didn't quite seem like as much of a stranger as they might have. And so there were a few things that that happened at the same time. And then the great financial crisis. And so you had people upside down on their houses needing to find some way to generate income. And so all of those things came together at the same time to help their Airbnb. The examples you shared are a good reminder that the inflection doesn't have to be technological. You shared a few of the categories of types of inflections.
25:07Can you just do it again? I love that question. I'm glad you reminded me, right? Because like, like, here's a really recent example when the laws were changed because of shelter in place for telemedicine visits, you know, it used to be illegal to do a telemedicine visit across state lines. But now all of a sudden with COVID and shelter at place, not only was it made legal, but it could even be reimbursed by the healthcare system. And so that's an inflection because it empowers patients to access more doctors and it empowers doctors to access more patients. And it also changes the delivery mechanism in an empowering way.
25:47And no event was at a technology change, right? That was a regulatory change that allowed technology to be empowering in new ways.
Read the full transcript
26:00But, in some specific ways, and there was a new set of empowerment conditions that ended up being made. And one of the things that we would ask at the time was, are they going to, you know, once COVID shelter at place goes away, are they going to revert back to the old laws? And if they did, that would have been a problem. And so that would be the empowerment condition. But, but, you know, it's a fairly robust way of stress testing any inflection right is to ask those three or four questions. So there's regulatory inflections, big changes in regulation. There's technological there's also, I think he's implied like an attitude like the way people see.
26:34Yeah, there can be a belief inflection. You know, so for example, during COVID, the amount of telemedicine visits exploded. And so as a result, there was a permanent change in people's belief about whether they would want to do a telemedicine visit. Before that, the technology was there, but a lot of people just didn't do it. The doctors didn't want to or decide to, the patients didn't want to decide to. But now all of a sudden, people were doing it. They're like, this is much better. Much rather do it this way than go visit the doctor and wait in line and all that stuff. For the doctors, like, I'd much rather do this than, you know, have these people backed up in my office.
27:11You know, I would argue that, you know, here we are doing a podcast on a video platform, right? Even though it's not Zoom, I would say that Zoom was another example. You know, the idea of people working from home a reasonable number a day is a week as a permanent condition. I think is another inflection that happened with COVID. And so are there's the three regulatory, technological and belief? Those are the main ones, you know, and I would say that in many ways, it's, you could say that from a macro point of view, it's two things. It's technology, changing, enablement, and it's people socially changing their beliefs and their patterns of behavior.
27:54And either one of those changes can be an inflection because either one of those changes can represent a turning point in one's capacity to change the future. Amazing. Okay. So we've talked about inflection. The next bucket is, in the next element of breaking through companies that you found is an insight. Talk about that. Yeah. So an insight, unlike an inflection, an insight does come from the founders. An insight, I like to say, is a non -obvious truth about how one or more inflections can be harnessed to change people's behavior. So if in the example that we gave earlier with lift, the inflection was the iPhone 4S, insight was, oh, that means you could do Airbnb for cars.
28:37And so you had to have some type of a creative insight to see that. Now, what was, you know, what was non -obvious about it or non -consensus about it? Who's going to want to get in a stranger's car? That's crazy, right? And thank God, I mean, if there's one piece of goodness about us passing on air bed and breakfast design, and, and and I were like, man, you know, nobody's going to want to stay in the stranger's house. That's crazy. And at the time, air bed and breakfast, the host of the guest state of the house at the same time, and the, you know, the host would beat pop tarts or something like that to the guest the next morning.
29:13We're like, you know, this is right around the time, we like the Craigslist killings and stuff. We're like, this is just scary, you know, kind of crazy. You know, couch surfing is a service, you know, but by the time we saw what was Zimrite at the time, what became left, and and I were much more prepared to believe that insight than we would have been, right? Because we'd foolishly passed on Airbnb. So that's a really important aspect of insights, right? So the insight needs to leverage inflections, but this is the subtle part that needs to be non -consensus and right, not just right. So in the world of opportunities, if you're right and consensus, you still don't do that well.
29:57And an idea that is right, but consensus has a couple problems to it. One is if it's consensus, it's probably not radical enough. Because, you know, when you think about it, human beings are conditioned to like things. And so if everybody likes your startup idea, it means it's too similar to what they already know and what they're familiar with, which means it's probably too similar to the consensus. It's too similar to the incumbents. And so the best startup ideas have this trait where most people don't like it or are even hostile to it or just kind of meh about it. But some subset of people are just like, oh my god, where have you been on my life?
30:39This is amazing. I love this. You know, they fall irrationally in love with the idea. And so most of the great startups that I've seen have that attribute to them. And the reason is that a great startup unlike a conventional company that proposes the futures and extension of the present. So the normal company's forecast, they say, I'm going to look forward from the present and forward project what the future will be. Great founders, pattern breakers, backcasts, they say, it's a given that the future has to be radically different for me to be a big winner. And so I'm going to look for radically different futures and work backwards from those radically different futures.
31:23And so the radically different future comes from that thinking different, thinking non -consensus. And then it's the different actions that get you to say, okay, now I'm out in this different future. But right now I'm all alone in this different future. I have to get people to come join me in that different future. And I have to find people who are ready to move with me to that different future. And that's where the pattern breaking actions come in. And like not everybody's going to move it first. And so I can't waste my time with people who won't move. I can't waste any urge of energy on anybody other than those ready to move or about to and then I need to co -create the future with those early believers.
32:01And so great startups happen when a subset of people in this world buy into the founders insight and then move with them to co -create that future. And then eventually what was a heresy becomes the conventional wisdom is more and more people start to realize the advantage. So many threads I want to follow here. One is the Airbnb story. Interestingly enough, I had Jessica Livingston on the podcast recently. And you probably know this, but Paul Graham and her did not like the Airbnb idea. They all like, this is a terrible idea. This we're just we're going to assume they will change the idea, but we love the founders.
32:34We're going to take a bet on it. So I was introduced to the guys by Michael Sybil from who was one of the co -fathers of Justin TV Twitch. And Michael introduced me to Brian Chesky before they applied to Y -combinator. So like Michael's like, they're not even close to ready to apply to Y -C. But like, you know, he thought that I was maybe would think that it was the right kind of crazy. I get pitched by a lot of like a, you know, I'm not very off put by crazy ideas. I could see why. So it was a and the meeting was totally discobobulated, right? So roomful cereal boxes. I'm like, what's up with this?
33:10Why is there cereal here? And then he can't get the product to work. So we're like 20 and I'm like, okay, that's okay. Let's just look at the slides. And he goes, well, Michael Sybil told me that you don't like slides. You like demos. I was like, that's true, but not working. So we're like 20 minutes into this meeting in a roomful cereal box. It's just looking at each other. And, and, you know, you can't win them all, right? You would sub you loose some. I wouldn't blame myself if I were you. Here's the other thing that's hilarious about Airbnb. So like, they do this thing because they can't pay their rent.
33:43They put up this WordPress site to pay for their rent because there's a design conference in San Francisco. In the case of the pandemic, they wanted to do a startup together, but like never occurred to them at first that air, air bed and breakfast was like the startup idea. They're like, we just need to use that to make money so we can go do a real startup. And so that's the irony too, right? Is it that, you know, you look back on it and almost smile at the fact that they didn't, they didn't know what they even had it first. You know, it was almost an accident. There's a lesson there of like, you find something that works.
34:17And even if you don't think it's a big idea, don't take that for granted. I very agree. And the other thing, the other great lesson is you don't want your initial startup bets to be too big to fail. Right? You want, you want ideas that are small enough to fail a lot because you know, you don't want to be attached to success. You want to be able to just try things and play with stuff and tinker with things because you don't really know where the fractal of new insight is going to reveal itself. And so you know, there is a little bit of play to this that I think is pretty important. Do you remember what's what some of the ideas they're brainstorming by the way?
34:56I don't. I don't. I don't. I'm longer if they even they do. Right? Yeah, probably not. Probably not. The Airbnb story, right? And your book. I feel like them failing in your demo help prepare them for YC. And that's what help them get in. So I think that you're a big part of their story. And to make it even more painful, like I'm in the book, right? Somebody, somebody called my wife Julie the other day and said, is that your husband in the Airbnb story? And we get the we get the book and there's a chapter and it talks about how hard it was to raise money. And they weren't dissing on me as a dumb VC.
35:27They were like, you know, look how bad we were at presenting this at first. Right? It was just a complete catastrophe presentation. But that's another good lesson for me too. I learned a very permanent lesson from that, which is just because the presentation is good or bad. It has nothing to do with whether you should desperately invest or not. Sometimes you have to be awake to the possibility of what it's going to be, regardless of how messed up the presentation is. What was their evaluation at that point? Oh, God. This hurts to. I think he offered me a chance to invest it at $1 .5 million valuation.
36:06But now there are a hundred billion dollar business. Oh, yeah, I would have made like 6 ,000 times of money or something like that. Okay. Great. Thank God. I said yes to Twitter and just D .V. And, you know, we said yes to lift an off deck. If we'd seen all of those and passed on all of them, I'd be apoplectic. I think that's what's interesting about your stage of investing is you you just need a couple to work out for you to wait. Yeah, that's right. And by the way, it's true when you're a founder too. If you do this right, you only have to be right once. Right. And so that's that's really important.
36:44Coming back to the insights lesson, one thing that you brought up when we were chatting about this is the importance of being surprised in the power of surprises. Can you talk a bit about that? Yeah. So, so there's a couple of things about insights that I think are really important. And this is one of them. I believe that there can't be a recipe for breakthrough. So, you know, and why is that? Well, recipes exist for things that have already been discovered. So, if I give you a recipe for making your cake, somebody has probably made that cake, right, before the exact way they're defining it. And so, breakthroughs, though, by definition, haven't happened yet.
37:22They haven't been discovered, right? The general theory of relativity had to be discovered by Einstein, right? And the, you know, the idea for ridesharing had to be discovered by the ridesharing companies or Airbnb by by Chesky and Nate, those guys. And so, what you want to adopt is the right mindset. And how do you adopt the right mindset? You, you interact with new technologies at the cutting edge, but you actively savor surprises. And when you think about it, when you think about it through the lens of a breakthrough and what we just said, it makes sense because if you want to find a breakthrough, you want to be surprised.
38:01You want to discover the undiscovered. You want to know something you didn't know before. Because if all you do is an experiment that proves that validates what you think, you didn't really learn anything when you think about it. You know, you just doubled down on your existing understanding or opinion. I learned this lesson from Scott Cook, who was the fatter of into it. Whenever he would be presented a new product, people would present the idea to him. And he would say, what were your three biggest surprises as you were coming up with this plan? And what he would find is quite often they couldn't name any.
38:38And he felt like when people can't name the surprises they came up with, they're too brain -locked on what they want. They have the agenda they have, they want validation rather than truth seeking. And so like if you're an authentic truth seeker, you're always hoping to be surprised and you think of surprises a gift because you think, well, maybe I encounter that surprise for anybody ever has. And so that's kind of what we mean. And you want to construct your experiments so that you're in a position to be surprised. So a good example would have been what the guys at Cheg did. So Cheg was wanting to see if people would do textbook rattles.
39:18So they created a fake site called textbook flicks. But here's where a small and I use were were very savvy rather than just test whether people would rent a hundred dollar textbook for $35. They tested an arbitrary set of prices all the way up to $75. And so they had the demand preference curve at different prices. And textbook flicks wasn't a real site. So you'd get to the shopping cart. It would give you a 404 error. But we could tell that people wanted to rent textbooks. And the surprise was that they would rent them for more than we thought we thought we need to get at least 35. But some students were well to base 75.
39:55And so that understanding was huge. If we'd only done an experiment to validate the hypothesis of yes, will they rent it for 35. Our pricing model would have been totally different from oh wow. And when you think about it, it makes sense like the student didn't want to keep the textbook, you know, econ 101. I'm going to give it back anyway. So 75 bucks is less than 100. I can buy beer with the extra money. So that would be an example of the surprise. But most of the startups that have had great outcomes, I find there was a kind of a surprise like that, right? You know, being non -consensus is not the same as being contrarian.
40:34You know, being contrarian is another form of conformity because it's still relative to somebody else. Most of the great founders, I see the almost -fuel guilty that they found this secret. But they earned the secret by tinkering with the future and noticing surprises and having their noticing filter tuned to like volume 11, where most of us wouldn't notice it. Most of us would just pass the secret right by because we're looking to validate what we think is already true. You referenced this term that is also one I love that you use occasionally this earned secret. Can you talk a bit about that?
41:09It's basically the same idea that you uncovered something by trying things that no one else has seen yet. Is that the general idea? So to me, secrets are earned. Like a lot of people I think have the wrong idea of what vision is. Like a lot of people tend to think visionaries, it's like they have a special pair of binocular and they can look out farther than the rest of us can. But in my experience, that's not how inventions really happen. The way inventions happen is people get their hands dirty and they learn about what's missing in the future because they're getting their hands dirty with what's new about it.
41:47And so they earn the secret by going down this rabbit hole of exploring something at the cutting edge for its own sake and they become like just like I'm a train spotter for startups, they become a train spotter for this new thing that they're excited about. And you know, they frustrate the people around them. They'll be at a party and everybody's talking about the basketball game and the Celtics against the Mavs and somehow that reminds them of the fact that they wanted test prices for textbook rounds. And it's like, but they're that interest is the last thing they think about when they go to bed.
42:21The first thing they think about when they wake up. And so that's where I find most of the really great darn secrets come from. They're earned in this sense that you earn them by getting your hands dirty and you earn them by being awake to the possibility that secrets are there that just most people aren't looking. This connects with that statue shared that 80 % of your biggest returning investments came from a pivot. It all connects where you just try and stuff, you're learning, seeing things people haven't tried and that's right. You know, and in the early days of product market fit, I like to say we want to answer a very simple but profound question.
42:56What can we uniquely offer that people are desperate for? And if we have an insight, that makes us unique. Now, if a customer doesn't like your idea, a couple of things could be true. One is your insight could be wrong. Your insight's wrong. You don't have a startup, right? You should just stop. The other thing though that could be true is your implementation is wrong. So like you had the right insight. So like Achta, at first they wanted to do cloud systems management. They thought that they needed to do problem resolution. But when they showed it to customers, they were kind of meh about it.
43:32And they said, well, what, you know, why are you meh about this? And they said, well, it's not a top priority. They said, what is your top priority? They said identity management. So they had the right insight, which was customers would struggle to manage cloud services. But they had the wrong implementation of the insight. So then they came back with identity management at work. So, you know, if somebody doesn't like your idea, if they're not desperate for it, either the insights wrong, the implementations wrong, or you could be talking to the wrong customer, right? Like some, some people that ought to talk to wanted to integrate it with on -prem software.
44:07And in that case, their opinions are relevant because they're not an innovative customer. They're not living in future. They're not going to give you product requirement ideas that are additive to your strategy. And so, you know, you want to be right insight, right inflections, right implementation, right early believers that you're talking to as you iterate towards product market. And if you're not succeeding at product market fit, then it's one of those, one or more of those variables is of working. I think this might be a good time to remind people that you don't need to have every one of these for your business to potentially be a huge success.
44:44It's more that the more you have, the more likely it is that you will find something massive. Is that right? That's right. And it's like what this is the hard part about the non -consensus at right is you don't know for sure that you're right at first. You only know that you're non -consensus. And so you have to be willing to risk being wrong to be spectacularly right. And so what you're trying to do though is pursue opportunities where the odds are massively in your favor. And so like I kind of return back to businesses never fair fight. And so if I'm a founder, there's a set there's a universe of ideas I can pursue.
45:20The mistake that a lot of founders make and it's very understandable. They say I want to go after big market opportunities. So they analyze big markets. They find to unserve customers with unmet needs in under -addressed markets. So then they go build a product to go solve that problem. And that's very appealing because it seems obvious and the dots connect forward in an obvious way. But unwittingly it buys into a context. It buys into the current definition of the market, which was already set by the incumbents. And so what you instead want to do is pursue a slightly more ambiguous opportunity.
45:58But one that harnesses these powers, one's where you look at the inflection, you say, wow, that's really powerful. You look at the insight, you say, yeah, I know that this is going to be in the future. I know that this is where things are going to be radically different someday. I would rather have those things present and be willing to pivot the product than not have those things and have a much clearer idea of what the product should. Funny enough, one of my biggest investment successes did exactly what you're saying you shouldn't do, which is they looked at a huge market with a bad incumbent and built something better and it's working.
46:33But I think, again, it's not that you can't win that way. Your point and your research shows that your chances are a lot higher doing something totally different. That's right. And I would bet that this company, I don't know enough about it. I don't know what it is, right? But it wouldn't surprise me if they harnessed inflections in some way that was disorienting to the incumbent. It wouldn't surprise me if they found a way to use it, flexions to fight an unfair bite. What I try to do with the insights is I realized there was a theory behind it, like a theory is not a recipe at explanation. And what inflections let the founder do is wage asymmetric warfare on the press.
47:10And the insight is like the vessel that they use, right? It's kind of like the rock is the inflection, the slingshot is the insight that they shoot at David or David shoots at the lieth. Right? And so that's what we're looking for. We're looking to create the conditions where we're going to get to play an unfair game by unfair rule favor us. Great segue to the third bucket, the third element of breakthrough companies future founder fit. What is that? Yeah, so this is one of my favorites. So a lot of times people will say what makes a great founder. And there are some common traits, right? Passion for the idea, persistence, resilience, you know, all of all these things, right?
47:53That people talk about passion for the users. But what I find is that there's no canonical best founder, right? So Mark Andreessen started Netscape as a programmer making minimum wage at the University of Illinois. And everybody thought the digital highway at the time was going to come from time Warner or from Microsoft network or from the US government. Nobody thought that some kid was going to do it from the bottoms up. But it turns out that Mark was tinkering with a set of inflections around the worldwide web. And you know, right around that time, Microsoft introduced a better version of Windows and right around that time, the Pentium processor came out.
48:33So there were, you know, more more people like graphical user interface computers at the very time that browsing started to happen. But let's take another company more recent applied intuition makes simulation software for autonomous vehicles. If you're going to sell a giant contract to the CEO of a car company, he needs to look at you across the table and think these guys can do the job, right? So, you know, Cascer and Peter had been, they'd grown up in Detroit and Michigan. They had worked at car companies in the past in the big three. And then they worked inside a Google at Waymo and Google Maps.
49:13And so and they'd had a successful startup before. And so if you looked what what is a team from central casting to do this, it would be them. And so what what I mean by founder future fit is there's a set of traits that a founder can have that make them ideally suited to a certain type of future. Sometimes they're really young first time founder Mark Zuckerberg, Bill Gates, Paul Allen, you know, we just gave the example of of Mark and recent in that case usually they're at the cutting edge of a new technology. And they have a beginner's mind and they aren't even encumbered by the old way of looking things.
49:51It's like the entire world lives in Cartesian coordinates and they discover polar coordinates. And they don't even have to translate between the two because they never understood Cartesian coordinates. And so in that case, their knowledge about the future is more valuable to success than their knowledge is business people. But in the case of like applied intuition, if you're selling very large contracts enterprise customers, they need to believe that you could do the job. If you're often you're doing identity management for cloud customers, they're going to trust Todd McKinnon from Salesforce way before they're going to trust a college dropout to do that job.
50:29And so I like to say founder future Fed is, you know, who knows the most about this future? Who has the most intrinsic motivation to pursue it? Who has the best network and keep the best company in that ecosystem of the future? You know, those are the types of things, you know, founders that show up differently on those dimensions usually do better because they're more likely to understand what to build in the first place. And they're more likely to convince early believers to believe in their ideas in the first place. So it's not that these people have some vision of the future that is more accurate or more incredible than everyone else.
51:11It's that they're background and even the way they look matches the problem that they're going after. So in the supply of intuition case, you're saying like the founders look like people that CEO of GM would be like, I trust these people to build this thing for me. Yeah, I like to, you know, Louis Pasteur once said, chance favors the prepared mind. And when I started working on this book for the first time, I really understood what he meant, right? Like chance favors the prepared mind because a prepared mind attracts luck. A prepared mind is better positioned to notice a breakthrough than other minds.
51:50And a prepared mind sees the breakthrough, sees around the corner because they're thinking about the subject all the time. And so like most people think that the way you come up with good startup ideas is try to think of startup. And I like to say no, that's exactly wrong. What you do to come up with great startup ideas is you live in the future and you notice what's missing in the future. And it's like, it's it's axiomatic. If you're living in the future, there will be unbuilt missing things because if it was all built, you'd be living in the present. And so if you're if you're living in the future and you notice what's missing, you're intuition about what to build is far more likely to be right.
52:31So like, you know, Andres and didn't do the mosaic browser because he thought there was a market for browsers or the he didn't even know about a digital highway. He was trying to make the internet immediately more useful for him and his team and his intuition about what to build was very good because he was building the thing he wanted that was missing in the world. You know, in the case of Opta, they knew all the early Salesforce customers, but the but the principle still applies, right? Those customers weren't equal. You know, they were light house customers kind of like when I was at Silicon graphics, I didn't spend time with normal movie studios.
53:07I spent time with industrial light magic because I thought if we solve their problem, they're going to take us to the promised land, right? All the stuff we build for industrial light magic will be the stuff that everybody wants some day. And so like not all customers are equal. You want to find customers that live in the future. I love this point. Justin TV is another great example. This were just assumed the future. Everyone's going to be watching each other's reality shows. He built his own backpack with a camera in a site just to stream. So yeah, and and the Justin TV examples are great when too because right in Justin TV, he built the thing that he wished he had, even though it was a terrible idea.
53:43But it embodied attributes and embody these inflections and these insights that led them ultimately to Twitch. Ironically, Justin's second company, Atrium, most people thought that that made sense. Automating legal tasks and, you know, Justin's a great founder, but Justin just didn't like the legal field. He had no passion for either. When he started Atrium, his passion was to be a higher status founder. And I've got a podcast with him recently where he talks about this, where he's like, I wanted to be as big as Patrick Collison and Brian Cheskey and Drew Houston. But it turns out that's not a very good reason to start a company, right?
54:24Like founder future fit is ultimately about authenticity. And it's about who is the most authentically matched for that different radical future. And that whoever that team is has a really big head start in getting product market. And you know, product market fit is the game right? Whoever gets it versus wins. This episode is brought to you by Weptflow. We're all friends here, so let's be real for a second. We all know that your website shouldn't be a static asset. It should be a dynamic part of your strategy that drives conversions. That's business 101. But here's a number for you. 54 % of leaders say web updates take too long.
55:03That's over half of you listening right now. That's where Weptflow comes in. Their visual first platform allows you to build, launch, and optimize web pages fast. That means you can set ambitious business goals and your site can rise to the challenge. Learn how teams like Dropbox, Ideo, and Orange Theory trust Weptflow to achieve their most ambitious goals today at weptflow .com. Okay, so there's inflections, there's insights, there's future founder fit to make this super real for say a product manager sitting at a company right now. I want to start a startup or someone just starting to ideate on ideas.
55:42What are some things that you recommend they start to do this week next month to start to find a big idea or to start an idea? There doesn't have to be a big idea. An idea that'll take up somewhere. The number one thing I like to say is get out of the present. And so like what what you know, people talk about getting out of the building and of course we should. But getting out of the present is a little bit more subtle than that, right? So William Gibson was right. You know, when he said the future is already here, it's just not evenly distributed. So most great startup ideas come from a future that exists right now today.
56:21And so when I like to say to people, and this is a question that I always ask when I'm pitched, is this from the future? And you know, and then some people will say to me like, hey, I have a mental health startup. Mental health is a huge problem. It needs to be solved. And I'll say, why is your idea from the future? Well, in the future, I believe mental health needs to be solved. I'm like, that's not what I'm asking. I'm asking what part of the future have you been living in that gives you the right to have an opinion about the future? So right, I like to say if you're not living in the future, you don't your opinion about it is at ballot.
56:57It's kind of like saying, I think customer will do X and you've never talked to a customer. I'm like, okay, your opinion is interesting, but irrelevant. And so the only relevant future, the only relevant opinions about the future come from people who are living in it. And coming from people who understand what's new about it in a very visceral way. And you know, there are people who do a good job of this, right? Like Maddie Hall, who started living carbon. She was working at Zenefit. And at first, she tried to think of a startup. And she had ideas that weren't that good. She had a laser tag idea, a few other things.
57:32But then she decided to go follow Sam Altman for a year, be as chief of staff. And Sam Altman visits the future multiple times a day with people. And so that's what led her to this idea that for living carbon, which does genetically modify trees. But I mean, couldn't be farther away from Zenefit, right? But like she saw, Microsoft was about to spend a lot of money, but other companies about to spend a lot of money on carbon takeout. She saw that the genetic engineering technology was getting good enough that you could engineer these trees. She married the inflections with the need. And then off she went, but she was, you know, basically sampling a lot of different futures until she found one that she liked.
58:15I love that example because it makes it very real. What living in the future looks like. So one is spend time with people that are very far along on some edge of technology or the way people behave. Another you shared is a work with a company like say, uh, they work with a silicon graphics. Yeah. That's like magic. That was magic. Yeah. Yeah. So McCracken had a term for it that I've always liked, uh, lighthouse customers. And so like the lighthouse has this light that shines out and unabskures the fog and not all customers are equal. And some customers are living in the future. And those customers are gold.
58:53And those customers will, if you solve their needs, take you to the promised lane. And so like, so yeah, you can, you can, you can build what's missing for yourself, like Andrew Sondid or Zuckerberg or Steve Wasmianck or Bill Gates, or you can build something for lighthouse customers. You have a good relationship with. Or if you can do neither of those things, the number one question I get asked is, hey, that's great. If you live at a supercomputer lab or if you, you know, uh, were selling the dust relight or magic or like all the sales horse, because I'm not one of those. I'm a second year student at Stanford Business School.
59:31I'm a product manager, company ex. I'm, you know, whatever the case may be, that's where the Maddie Hall examples really powerful because Maddie proactively got out of the present in a very intentional way. So I love, for example, uh, as a case study. What signs tell you that a company is one of these lighthouse companies living in the future person is just like you just feel it like they're so far ahead of everyone else. You usually it has to do with how tech forward they are. You know, there was, there was a time when a lot of people didn't think the cloud was going to be a thing because it was insecure.
1:00:05And I'm not going to host my important data and let somebody else have it. But there were a set of customers who were really excited about the cloud and they tended to adopt certain kinds of products. When I used to work in client server startups, you knew that the early adopters were people who are using like relational database servers and scalable front end programming, uh, interfaces and things like that, you know, we're trying to have distributed apps that they would roll out. You know, you could, you could tell who was trying to play offense with the new trends. Awesome. Okay. Before we move on into actions, is there anything else you think might be useful to share in terms of helping people come up with an idea, find a great idea.
1:00:48The number one thing about the ideas goes back to not playing the comparison game. So the thing that I see people underestimate when they come up with ideas is the threshold of desperation required in the customer, right? So like, like, um, if we want to solve problems for desperate people and it's like, if we have powerful inflections that really empower and we have something unique, there should be somebody who is irresistibly drawn to that empowerment. They should say, oh my god, this is incredible. This is a game changer. I can't unsee that. Why is that important? I like to say that if a customer has the ability to do something other than what you do to solve their problem, they won't be crazy enough to do business with a startup, right?
1:01:41So customer has to be so desperate that when they see what you have, they're like, I've got to have it. And so I like to say you want to force a choice in not a comparison. If everybody's selling apples, I can't be a ten done better apple. I want to be the world's first banana. And I want to say to people, you may not want bananas. You may not like them. You may not may not value the advantage of bananas. But if you value bananas, I'm the only person that's got and it's like, you know, come to PAPA, right? And so that's like an insight feels like that. And in the early days, don't spend any of your time with people who love apples because you're not going to convince them and they're going to waste your time.
1:02:23What you want to do is find everybody in the world who values the advantages of bananas as soon as possible, not wasting any time on the people who don't. And so I'd say that that kind of wraps up the idea of insights. Is it like, we want to force a choice in not a comparison? You know, nobody looks at the Tesla Cybertruck and says, oh, yeah, well, how does that compare to Ford F -150? And you may hate the Cybertruck. You may think it's stupid, but nobody is neutral about the Cybertruck, right? That's you want to have a product that people can't be neutral about, but that the people who have magnetized positively to it just can't imagine a world without.
1:03:03I love that. And going back to your banana example, you want just a few people to be just like, I need that banana no matter how much you're charging. That's right. And even if it's halfway right, even it's like, you know, because that's the other thing, right? They need to be willing to tolerate the fact that you can't execute very well, because like, how could a startup execute really well? They have no resources. And so like the only chance for a startup to win is to win on a playing field where better does it matter, where execution isn't as important as God, I have that thing. I'll take any version of it you give me because I am desperate for it.
1:03:42Speaking of execution, it gets like way to the second part of the chat, which is basically you look into what do the most successful companies and founders do differently. And you also found three core things that they all do and many of them do. Movements, storytelling, disagreeableness. Let's talk about each one. Pick whichever one you want to start with. Yeah. So, so, you know, we've talked about thinking different, but it's like the problem though is that, you know, asking people to abandon the familiar for an uncertain tomorrow is a provocative act. All startups are fundamentally disagreeable.
1:04:21There are disagreement with how things are done. There are disagreement with the pattern of what is. And so, we need as founders to persuade others to change their habits with our pattern breaking actions. And so, what the pattern breaking founder does is they create a stark dichotomy between the world that is in the world that could be. And they create an irresistible desire on the part of early believers to move to that different future with them. And so, you know, I like to say there are three aspects to acting different, right? One is movements, the other storytelling, and the other is a disagreeableness.
1:04:59And so, like the movement piece is the front and center piece because like most people when they think of movements, they think of it as more like social movements, like civil rights movement, Martin Luther King, or they think of, you know, there's artistic movements like Cubism and Picasso. But like fundamentally, a movement is a different way of developing a market than how most marketing people think about developing market. Most people, when they think about marketing, they think, okay, I've got to set a target, I've got to set a program, I've got inbound and outbound, I've got, you know, these things I need to do.
1:05:33What a movement does is it it leverages a grievance of a minority against the tyranny of a majority. And it takes that and animates it in a way that those early believers are emotionally committed to moving. So like early customers are not animated by pragmatism, they're animated by belief. Early customers, early employees, early investors, don't decide to go into business with you because of the practical reasons that you unlock. They do it for aesthetic reasons. They do it because they believe what you believe. And so a movement is basically a set of people with the same belief moving together to a different future.
1:06:22And when you think about it, it's equally the same right for the civil rights movement. And a movement is a way to crystallize the choice. Like if you're, if you believe in civil rights, you can't be half in on that. You either believe that that it should be about the content of people's character or not their skin color. You can't be sort of not racist, right? You either believe or you don't believe. And you know, the people who followed Martin Luther King bought into the aesthetically better future that his movement promised. And it turns out, and I don't mean to equate, that was a pretty important movement, right?
1:06:59There's like some movements are more frivolous, you know, like say an artistic movement. But the notion is similar in that there's a set of early believers who believe they've been enlightened about something that the rest of the world doesn't get yet. And they think that the startup founder is sort of like the prime mover of that movement. And then what happens is that startup markets happen because the movements accumulate and accelerate and more and more people join them. And what was once heresy becomes the accepted conventional wisdom. And now the company's no longer a startup, it's company.
1:07:34And now all of a sudden it is a valid market and all of a sudden they're the status quo and they got to watch out for the next set of disruptors. So the movement is the first key thing I think in all of this. Is there an example? Lift obviously comes to mind with this. The big mustache is just this is the future. Yeah, ride sharing, ride sharing was a movement. And you know, in in my early days starting floodgate with Anne, we thought that seed investing was a movement. And so we thought that there was going to be a day where seed funds would be a permanent feature of the venture landscape. But people didn't believe that in the late 2000s.
1:08:09And so we're like not enough that we just succeed and invest in good companies. We need to get the best LPs in the world to buy into this, right? We need to get Phil Horsley at Orsley Bridge and Dave Swenson at Yale and people who you know are respected in the ecosystem to say, yeah, I buy into that. And so it was really important to us to get the right early believers in our movement. You know, Judith Elcia weather gauge and just started a new firm. One of my favorite examples is actually an old one Clarence Bird's Eye. So you know, you go into the supermarket and there's frozen food aisle. Well, Clarence Bird's Eye discovered how to flash freeze food when he was up in the Arctic looking at Eskimos.
1:08:53And they were flash freezing their fish and he wondered, could you do it for other things? And he found out you could recruit the vegetables. But like, it wasn't enough to just flash freeze the fish or the fruits or the vegetables. You had to convince the trains to have a refrigerated car. You had to convince the supermarket to have a refrigerated aisle. And so he had to start a movement where a whole lot of people simultaneously believed in this idea of being able to eat food in a more convenient way, not always in season, not always grown locally from where you were. And so all movements have that characteristic where you're, you know, you kind of start with a higher purpose and then you move people to that different future.
1:09:34I'm trying to think about what are current movements that are happening when that might be a movement is with LLMs, just this bet that transformers are the future of how this is going to work that just more compute if the answer versus trying to find something else. That's how right? Another one that I really like is Tesla. So like Tesla's mission says, accelerate the world's transition to sustainable energy. They don't even say they're a car company. So like Tesla doesn't say, here's why we're better than Ford and Toyota. And this is really important, right? Because the great movements do appeal to a higher purpose.
1:10:12They don't say I'm better, I'm better than company at, you know, I may, this I try harder than hurt. They appeal to a more aesthetically higher purpose future. And then they show that this startup is the vehicle for that movement to be actualized, which is kind of a good segue to storytelling. One other quick example, I'm thinking about linear is kind of pushing this movement of craft and design and experience matters and be to be software. And you shouldn't settle for something that you don't love very much. So and you know what, Chesky, this was, I don't think he even knew he was fully doing this at the time.
1:10:47But Chesky did this brilliantly with Airbnb. So he created a movement around living like a local. And so the other thing that a movement does is it turns the greatest strength of the status quo into its biggest weakness. And so like Brian never said hotels suck, you know, death to the four season. He just said, hey, look, you know, when you go to Paris, you have a choice. You can, you can hang out in the four seasons and it's going to be just like the four seasons everywhere else in the world. It'll be in the middle of the town or you can live in Paris like a Parisian. And he's like, I don't have to say that the four seasons is bad for you to decide to choose me.
1:11:26And oh, by the way, if you want to stay in the same kind of hotel everywhere you go, I'm not for you. But so like now let's say you're four seasons, your whole business is predicated on doing a good job of having a common experience that people could accept and that they're used to and that they expect. And so now you've taken all of the stuff that you invested decades in and turned it into something you have to apologize for all of a sudden. And so, so like the great startups, they create movements not so much by criticizing the incumbent, but by showing the weakness in the strength of the income.
1:12:01And then just saying to the customer, hey, look, you decide it's not up to me to decide what's bad about four seasons up to you to decide whether you value my difference or not. That reminds me of counter positioning for Hamilton Hamilton, Helmer seven powers book. 100 % So to make it even more practical for people, they're like, oh, I need to come up with a movement for my startup. That's why things aren't working. It sounds like it's kind of a here's how we want the future to look and why we're doing this. And then it's a combination of marketing, positioning, messaging, repeating it, social media.
1:12:33Imagine is that is that roughly how to think about? Oh, but but I would also say that it's about storytelling. And so like storytelling, there is a science to storytelling. And so like, for example, you know, the heroes and journey, you have somebody in the world that is the hero. Let's say Luke Skywalker on Tatooine, Dusty Planet, he's bored out of his mind. And then a mentor shows up and offers them a call to adventure. Obi -Wan Kenobi. And at first, they resist the call. But then something bad happens, you know, in this case, Luke's like, hey, I can't I can't come with you. I got chores to do for Aunt Baroo and Uncle Owen.
1:13:15But then he comes back to his place and it's all burned down. The stormtroopers killed his aunt and uncle. So then he accepts the call. The mentor has a tool and a magic. In this case, it was a lightsaber was the tool or the magic was the force. And they need those things because the hero has to have a reason to credibly believe that they can beat the bad guy. Right. It's a then they then what happens is you you you find co conspirators along the way. Han Solo, Chewy, you know, ultimately princess. You you rescuer, you blow up the death star, you beat the empire and then emerge transformed. They even get medals at the end of the movie, right?
1:13:58Now it turns out that the exact same thing applies for startups. So like if we take the lift example, let's just say I'm a rider. In the past, the world that is taxi suckers, I can't even get one. And when I get one, it's gross. It smells bad and it's late and it won't take my credit cards. I have to have cash that can't rely on them to get me there. I guess my alternative is a park. You can't ever get parking people break into your car. That's the world that is. Logan and John would call engage in a call to adventure. Try this ride sharing app. It shows cars on map. You know where they are all the time.
1:14:35They come within five minutes, fist bump the driver. Now this was where the genius of the pink mustache came in. So the pink mustache honored the fact that a lot of times people resist the call. It's scary to get in a stranger's car. So the pink mustache made it seem a little bit less scary. When you see these cars drive around in San Francisco, you're like, what's up with that pink mustache and you're talking to your friend. They say, oh, it's this new thing called lift. It's pretty cool. You know, it's an app if you see it. And so Logan and John did among the best I've ever seen at honoring the fact that people might resist the call.
1:15:12But then part of the story is languaging. This was the genius of Twitter. They didn't call it micro -blogs, right? They created a metaphor around tweeting birds. You know, the Tesla was this way. Right? It wouldn't have survived a comparison with a Porsche 911. It just seats were as good. The radio was as good. But Elon was telling the story about a different future. And when you bought the Tesla Roadster, you weren't buying it for practical reasons. You were buying it for aesthetic reasons. You were buying it because you thought that that future was something you wanted to be so the storytelling primitive ends up working spectacularly well for startups, right?
1:15:50We need to describe the world that is. We need to describe the world that could be, which is that different future. We need to understand and this is important, right? That your job is the founder is to be Obi -Wan, not Lou. So the founder sometimes make a mistake of thinking that they're the hero, but they're not. The early believers are the heroes. And it's the job of the founder to tell a story. That emotes early believers to want to move with them and co -create the future with them. And like the story you tell an employee is different from the story you tell an investor is different from the story you tell a customer.
1:16:27Because all of them have a different idea of what their heroes do. You know, if you're an investor, maybe your idea being a hero is to make a hundred times your money and be on some fancy list and make money for your LPs. If you're an early customer, maybe you're a hero by solving an important business problem and getting recognized for it in your company. If you're an early employee, maybe you want to work on something you're excited about with really awesome people that don't waste your time with politics and bureaucracy, right? And all of those are different journeys. All of those are different transformational ways to self -actualize.
1:17:02And we have to we have to meet those people where they are and give them a reason to want to come with us to the world it could be. I had Nancy Duarte in the podcast. She is one of the most famous presentation designers and she had exactly the same advice when you're trying to tell a story. You basically bounce back between the world that is the world that could be what is what could be what is what could be and just kind of keep going back and forth. 100 % in the fact Nancy is the person who helped me understand this better than any single person. So so Nancy would show me how Steve Jobs's iPhone watch speech.
1:17:37She'd be like, okay, well, now notice what he does. He shows how bad phones suck now. They have styluses, they have keyboards. And then he talks about what could be you could combine an internet communicator, you could combine an iPod. And he goes back and forth between how bad the current state of things is how it should be, how bad it is, how it should be introducing the iPhone, how bad it was, how awesome it's going to be, how awesome it is. Like when you look at his speech, he's masterful at toggling. And by the way, the same is Truvee Blinken with the Gettysburg address. Horse four and seven years ago, new nation, now we're in a civil war.
1:18:20You know, we need to preserve what we stand for as a country. We need to go win this war. But he kind of goes back and forth, drawing attention between what has happened in the world that was and the world that could be something that I was thinking as you were talking was I've seen too many founders spend so much time crafting this amazing story and vision of their product. And they have this really cool blog post and big idea. But nobody really cares about their product yet. Give you any advice of just like just make sure you're building something people want above above all else. And the story is a layer on top of that.
1:18:55So many startups. I see the first slide is like we're at me AI software. We're located in San Francisco. We're funded by X and Y VCs. That's not storytelling because you're talking about yourself, right? Like, and if you're trying to make the person in the audience, the hero, they don't care about you yet. They care about how you're going to make them a hero. And so like when you when you kind of say, okay, if I'm pitching VCs, what I really need to do is help them understand why they'll be a hero if they invested my company, according to what makes them feel heroic. What you present is different.
1:19:36But like what what a lot of startup presentations do is they take their sales pitch and they re -host it for every other audience. They re -host it for the investors and for employees and all that. And that's wrong because what you're doing is you're talking about yourself to different people. But what you want to do is describe the world that could be the stakes that are involved. And then each of those individual audiences, you want to meet them where they live in the world that is and show them how they can engage in a transformational journey to the world it could be. And also show your amazing stats and backgrounds and market size and all that stuff.
1:20:19Yeah, although it's it's funny, you know, I've found that investors are the same. Investors, ultimately they believe or they don't believe. You know, a lot of times this is the other thing I see happen is the poor founder will get advice from 20 different people about their pitch deck. And a lot of the people giving them advice are not believers in that different future. They're giving generic startup advice or they'll they'll go pitch a bunch of firms and they didn't they didn't consider who's prepared to possibly believe who isn't. And so then they then they get objections to their pitch for people who aren't going to believe anyway.
1:20:53And then they try to have a slide to meet that objection. And before you know it, you have what I call a franken day. And so you have this huge gigantic presentation trying to anticipate every objection. And the person who was ready to believe you in the first place doesn't know what you were trying to say because you obscured it with all this other stuff. And so I find that just like with an insight, it's okay if most investors don't like your idea what you want to find is the ones who are prepared to move with you and make sure they absolutely know why they should. That's to me, that's the ideal pitch deck.
1:21:28I love this advice. And just to be clear, this is like pre -seed and precede before there's a lot of traction, a lot of data. Exactly. So what's your advice to a founder that's trying to iterate on their on their deck as it just like don't show it to too many people as it stick to your guns? Okay, here'd be my succinct advice. Another matter is about a million details. Slide one, slide one, you say what you do as if I literally know nothing. So it's not where Airbnb were a marketplace for unused residential housing space. Bad. But you'll get advice that says to do that because VCs think marketplaces are hot.
1:22:05Residential real estate's big. What you should instead say is something like where Airbnb will let you rent an extra room in your house. Because now is the VC, I'm like, oh, I know what you do. And there are a lot of pitches I'm 10, 15 minutes in and I'm trying to understand what they do, but I don't know. So if you just say, here's what we do. And then the second thing that I say to people is I think your second slide ought to be here's the thing we know that's not obvious. So like when I was raising fund one for floodgate, I would go to LP and say, we believe that there's a gap between angels and VCs.
1:22:44The VCs are riding five million dollar checks, angels, $250 ,000. We believe that 500 ,000 is the new five million because of lean startups. We believe that there will be a new type of category funds called Z funds. Now, if you don't believe that, nothing else I'm about to say is going to make any sense to you know, I can just give you your time back because like it's not, but then once if they did believe that or they were in a position to lean forward. Now when they start mentioning my competitors, I say, okay, well, recall Peter Fenton works at benchmark. He's not going to compete with me because why would Peter Fenton leave benchmark to start seed fund doesn't make sense.
1:23:22The only people are going to try to compete with me from the big funds or people who aren't performing. But if you if you set the context of what your insight is, you can always come back to it when they bring up competitors, you can always come back to it when they bring up objections. And you could say, Hey, remember, like I'm just telling you, we need to agree on this insight for this slide three is what if any proof points do we have? Do any customers? Do we have great founders? You know, is there something happened already that should cause you to believe that my insight is vowed? I love this.
1:24:02I love this tangent we went on. When we come back to the actions that you found the most successful startups end up taking. We've talked about movements. We've talked about storytelling. The third is my favorite. I'm excited to hear you talk about it, which is disagreeableness. What is that about? Earlier, I'd mentioned that you want to escape the comparison trap when you have your insight and when you have your idea in creating movements and telling stories, you want to break free from the conformity trap. We always are under pressure to conform in this world. And you know, people use the pressure of conformity to prevent us from exploring things outside of our limits.
1:24:45You know, like there's a there's a book that I love called Jonathan Living's A Seagull where there's a Seagull who wants to fly at infinite speed and all the other Seagulls are like, look, we're just destined to eat crap off the surface of the ocean. That's just what we are or seagulls. And he ends up getting banished from the flock because everybody thinks he's crazy. So to me, the great founders are kind of like Jonathan Living's A Seagull. They're willing to pursue something that they're obsessed with that they think has to happen in this world. And they're willing to sacrifice their status, you know, in the socio -economic sometimes dominance higher.
1:25:25Because fulfilling the mission is ultimately more important to them than fitting it. And you know, you can't stand out if you always fit in, right? You know, only people are different can really make a difference. And so that's kind of the mindset. So I like to say a startup is a fundamentally disagreeable act in birthplace. And there's going to be times you need to be disagreeable. And I've seen this time and again, you know, like I hear people say to me, I want to work with a founder who's coachable. I'm like, I, you know, I'm not really sure, you know, like it, sometimes I used to joke that when I would meet with F Williams, my whole job was to give him advice that he ignored.
1:26:04So I would say to him, I'd say, Hey, yeah, but I don't think you should raise that much money because I think you'll spend whatever you raise in 18 months to matter how much you raise. And he said, man, that's so you mean that startups almost always spend their money in 18 months, regardless of the amount. And I said, yeah, I call it Mike's law that almost always happens. I said, because once you have the money, all the pressure is on you to spend it. And so, so he's like, man, you know, that is a really good advice. I'd never thought of it that way before. That sounds right to me. Well, he proceeds to go raise the money.
1:26:37But like, you know, he did stuff that I didn't think he should do, but it worked. And I'd like to that. And like a lot of people would say, well, doesn't it bother you that he didn't listen to you that much? No, because he was disagreeable, right? And he was the right kind of disagreeable. You know, he didn't say, pal, I'm saying, I'd, you know, I'm not listening to you law, law, I'm covering my ears. He listened and he understood what I thought the truth was. He just believed a different truth than I did. And you know, that's fine. You know, my job is the investor is to just help them see what my perception of the truth is, honestly, right?
1:27:15And if they decide to go in a different direction, that's great. They're the founder. They're the genius. And so I find that and you know, all of them, not all of them, but a whole lot of them are more disagreeable than history lets on. You know, like my dad worked for Bill Gates when he was at Microsoft. Bill Gates is not a warm fuzzy dude. He was, he was tough, right? He was a hardass. But great people are inspired by hardasses. As long as the hardass like makes this, you know, you meld the steel in the heat of the flame of high standards. And you know, people, sometimes people can't work for Elon Musk for very long, but almost everybody I know is worth for him really respects it because he has high standards.
1:28:01And you know, he's not trying to win friends and influence people. He's tried to land on Mars. And if you're a land on Mars, you got to be disagreeable some of the time. So, you know, I just find that that is a trait that is under underappreciated and these great founders quite often. Which is a shared reminds me of a recent podcast episode of Jeffrey Feffer, which I know you listen to, not where he talks about the rules of power, how people acquire power. And the last rule is understand that once you have acquired power, what you did to get it will be forgiven, forgotten, or both. And so your Bill Gates example, I think is a good one or people look at on a such a night.
1:28:39Dude, when, as you said, he was not so nice. Well, the years the other thing, and by the way, I listened to that episode for the beginning to the end, right? And I thought it was fantastic because I was like, the next thing I want to do is go to Professor Feffer and say, can we cast these seven principles through a pattern breaking lens? Like, let's assume you're a startup capitalist, you're not at a company because, you know, changing the future requires you to acquire a different form of power than, you know, you would say in an organization. But as I was listening to it, I was like, these principles all apply to pattern breakers.
1:29:17And, and, you know, like all of them, every single one. And the other one, right, is that I think that he said, you know, not everybody's going to like you. And, you know, if you, you want to be like to get a dog, but if you want to, if you want power, there's certain things you're going to have to do and reconcile yourself with. And so acquisition of power, you know, acquisition of power has this notion of you've got to, you've got to wield the carrot and the stick. If all you do is wield the carrot, you won't create enough activation energy for people to move to that different future. Sometimes you do have to use the stick.
1:29:54And sometimes you have to realize that people are going to use your desire to fit in against you. They're going to say, oh, you can't do that. That's illegal or you can't do that. That's unethical or you can't do that. You're being some tech bro bad guy who's like, you know, a lot of what I find with the founders I work with, ironically, before they win, they, they have to have the courage to be just liked because people don't like their idea. They think it's stupid lonely. But then after they win, it's even worse because everybody says you cheated or you're a bad guy or you broke the rules or you're too powerful or who, who gave you the right to decide what the future should be.
1:30:31And so they just, they get criticized unfairly in the other direction after they succeed. But in the end, that's what it comes with the territory, right? It's kind of, you know, part of the job description unfortunate. Yeah. You long goes through a lot of that. Something, something I said you tweet recently along these same lines is that most successful companies, there's tons of chaos internally. And everyone's working at these companies like this plays a mess. How is this even working? But you're, you're finding is that that's very common and normal. Yeah, especially in startups. So there have been times when I've said things like execution doesn't matter.
1:31:06And, and people can misinterpret that. You know, so when I mean execution doesn't matter. I don't mean people shouldn't get things done or people shouldn't say what did you do this week. But when I think of execution in a corporate stance, like corporations in theory should always win. They have big management team. They have more experienced people. They have customer suppliers, partners, brand. So startup never beats a big company by executing better for the big company. Start up wins over the big company because it proposes a radically different future, disorienting incumbent, and sort of chaotically moves people to that different future.
1:31:46But like every startup I've ever seen on the inside was what? You know, it was like a capitalist mutation. It was like it was like trying to find a a beat bench in the Galapagos Islands that's never been discovered before. And it's all ambiguous all the time. And people are arguing about what the right direction is all the time. And people are, you know, it's just messy. But it's like, you know, movements are messy. And that's just kind of, you know, that's kind of what comes with the territory. Like friend friend of mine, Robin Roberts once said, you know, make your mess your message. It's so true.
1:32:24Oh man, that's so funny. I love it. I have a couple more questions before we wrap up. Before we leave the actions categories, there anything else you think is important to share any other lessons that we haven't touched on? I think Lenny, I don't know if you've consciously tried to do this or not, but on some level, you've created a movement, right? And like you have no one has ever engaged people with product management sensibilities the way you have. And, you know, like I go to your site, right? And you even have merch, right? For product managers. I'm like, and you know, I imagine the early posts that you wrote it probably felt kind of lonely.
1:33:01It's probably like, I wonder if anybody's even reading this stuff. But it's like, it starts to accumulate, right? More people start to read it. More people start to tell their friends about it. And now, all of a sudden, it kind of becomes a thing, right? And so, you know, in many ways Lenny's podcasts, Lenny's blog and Lenny's newsletter are all, you know, kind of examples of facets of this movement that you're creating. But your movement is not just about the stories you tell or the guess you have or the podcasts or the write -ups you have, you have a point of view, right? You have a point of view about the centrality of a product manager in companies and in businesses and in the future.
1:33:44And it's like honoring that the way Nike honors athletes. And it's like that, the point of view is the movement. Just like the point of view is the company when it's a startup. This point of view is the story. It's the place that people want to go that got animated by the beliefs that you shared. Fascinating. And flattered. I have no intention of starting a movement. I could see what you're saying. That sounds like a lot of stress. I think you already have whether whether you met two or not. I think you have. All right. Well, I do have swag. And if you're on YouTube, this is our best selling item.
1:34:21A hat that just says product manager. People love it. I have it in the background. Can I wear one if I'm still not one? Absolutely. You've been one. And so forever product manager. Get grandfathered in for my past forever. Forever PM. Okay. I just have one more question. And this is around your last chapter, which I think is going to be useful to a lot of people. Your last chapter is about how to apply a lot of these principles to working at a company. So you're not a founder. A lot of these principles still apply. What advice can you share for people say, PM instead of large company to help them find powder breaking ideas, big ideas within the company?
1:34:57Yeah. So the first the first thing I think is important to understand is that everything about a value delivery system when you're doing a power breaking idea is different from a normal idea. So like the mistake that most companies make is they say, I've got this new powder breaking idea. It needs to be a third of my business in 24 months or three years or whatever. Bad strategy, right? So like, let's take a company like say Apple when they did the iPhone. The iPhone was a whole new thing. It was driven by in this case Steve Jobs the founder. You couldn't reconcile it with the original business of the math and not really even the iPod.
1:35:40So you had to you had to treat it as a totally different thing. And that's really hard for companies. Like so companies make the mistake of engaging in a pattern breaking product, but they make it too visible or it's a career career limiting move if it fails. And you know pattern breaking products have different types of leadership, different types of go -to -market motion as we've described, different types of ideas, different risk profiles. So you're instead of saying this company or this business is too big to fail, I need to make small bets that can fail a lot. The same is true with mergers and acquisitions, right?
1:36:22So if I buy a company I need to ask, am I buying a pattern breaking company to break the pattern of my business and go in a radically new direction or am I buying a company that's an extension of my current business? Neither is wrong per se, but the way you think about risk varies enormously. And so so like some examples that I have in the book of good examples are the iPhone, Steve Jobs, AWS, but some people object to they say, okay, that's easy for the founders to do because they're founders of the company and that's Steve Jobs at Chip Asos. So the other example I like is Skunk World with Lockheed.
1:37:03And so when they created a fighter plane in a very short amount of time and that's how they did it, they they had an organization totally separate from the main organization, somebody with absolute power and tried to make it not visible, tried to make it be separate because when you make it visible you start to drift it back into the tractor beam of acting like a pattern matching corporation. You know, another good example back in the day was Don Estridge at IBM when they did the IBM BC, but it's almost always an autonomous business headed by Maverick and you're you're trying to do something discreetly different rather than a better version of what you've already done.
1:37:45This aligns very well with we had two recent podcast episodes talking to PMs at companies that are doing zero to one stuff, Mehika and Tangi and Tangi had a really interesting tidbit along the lines you just talked about where he set up his team in a totally different time zone so that people that wanted to bug them just were like sleeping during that time and they weren't even online so that they could just focus on the work they were doing and it worked out. I'm mostly through that episode and everything that I've listed do so far, I'm like, okay, that totally that totally jibes with what I've seen.
1:38:17You know, the other person has an interesting take on this is the node coat block. And so the node basically thinks that what company should do is take some portion of their profits and let's say 10 % of your profits and invest it in projects likely to fail but with wildly asymmetric upside if they succeed and then make them not visible to the mothership in the early in it. And so you know, you want to you want to it's your willingness to fail that lets you have breakthrough success. And you know, in any coin that says can't lose bad on one side of it might as well say can't win big on the other side.
1:38:56And so you have to, you know, it's your willingness to fail and it comes back to departing from the consensus, right? It's your willingness to fail that enables to success and every time you depart from the consensus, there's a chance you're wrong, you'll be wrong, you'll underperform the consensus. But it's your willingness to do that that lets you outperform it. But there's no short cuts, right? The coin that says can't lose says can't win on the other side and lose big says win big on the other. Mike, this episode is so full of nuggets tactical advice, amazing stories. Everything I was hoping would be before we get to a very exciting lighting round, is there anything else that you think might be useful to share with folks that are trying to start a company or already along with the company?
1:39:44Yeah, the one thing I would say is that it's a lonely existence and it's okay if most people don't like your idea. And it doesn't mean you're right, but sure as heck doesn't mean you're wrong either. And so, you know, there's not enough people in this world willing to stick their neck out for things that they believe that they see before the rest of us. And so just for what it's worth, if anybody in your audience of one of those people, you have just my utmost respect and affection. And I hope that, you know, in those times when it's tempting to not believe, you know, it comes with a territory every great founder is faced.
1:40:30And, you know, it doesn't make you wrong. Amazing. What an empowering, inspiring would end it. Mike, with that, we've reached our very exciting lighting round. Okay, here we go. Here we go. First question. What are two or three books that you've recommended most to other people? A book called The Five Regrets of the Dying, Top Five Regrets of the Dying by Bronny, where she was a hospice nurse and she would talk to people in the last 90 days of their lives. And, you know, and she would find out the things that they'd wish that they had done in their lives that they hadn't. And I always thought that that was a good, that that was a good book because it reminds you about what's important and it reminds you that it isn't going to last forever.
1:41:18It's someday will be the last day. There's another book that that I really like called Chase, Chance, and Creativity by a guy named James Austin. And I think that it's a good book because it talks about how certain people tend to attract luck more than others. And that actually that luck is created. You do make luck. And so like I'm just fascinated by this idea of luck and how it can be, how it can be harnessed. So I'd say those two, I mean, there's a whole bunch of them. You know, I've always liked all of Clay Christensen's books. The other one that I kind of liked is that I read recently by Robert Green, the laws of human nature.
1:42:03So I like that one a lot as well. And then Nancy Gourdte's book, Resonate, we talked about Nancy earlier. I like that book a lot. I'm buying that first one immediately. That sounds incredible. I need that book. Regrets of the dying. I found it on Amazon as you're talking. Yeah, buy it. Good, good, pick there. Okay, next question. Is there a favorite recent movie or TV show that you've really enjoyed? So I really liked that that the movie about Enzo Ferrari. And I just I have this huge affinity for 1960s cars. And the way that they replicated these 1960s for R .E .s, I just thought was magical.
1:42:43I thought to the guys that did the special effects and just the attention to detail, I thought was just extraordinary. I have not seen it. This is quick aside as I was buying this book. Your book was recommended on Amazon for me. Oh, good. Here we go. Good job, Amazon. I will point people to where to find it at the end of these series of questions. But next question, is there a favorite product that you have recently discovered that you really like? When I was young, I, before I got into computers, I had a job as a professional calligrapher. And so I really like using a calligraphy pens. And not long ago, I sort of discovered the world, it had been a long time since I'd reconnected with that hobby.
1:43:27I discovered the world of vintage fountain pen. So my favorite product of recent times is a, this will go everybody will be like, that sounds pre -acetaric, but it's a mock -blank 149 first generation celluloid pen. So it was like right after World War II, and it was the Germans kind of coming back saying, we've still got it. It was just a product for the ages. It has a flexible nib. They don't, fountain pens don't work the way they used to. They used to make flexible nibs that you could write the way scribes wrote like in the 1800s and stuff. But then people in the modern world break those nibs and they use ballpoint pens anyway.
1:44:10But like when I use these old flexible 19 from pens from 1900 to the 1940s, they're just magical. I mean, they're just nothing like there's nobody's ever been able to equal that experience in modern times. Well, I gotta try one of these pens. Yeah, I'll give you one of them so you can at least get a feel for it. Yeah. Wow. I'll give you a product management hat. I'll get a pen. A beautiful pen. I think I win in this exchange. A visit? Two more questions. Do you have a favorite life motto that you often repeat yourself, share with folks that you find useful to come back to? I learned it from my dad.
1:44:50It sounds simple but it's kind of profound. Do your best. And what he meant by that is he didn't mean be the best. He meant that life is a gift. You don't know how much time you're going to have. Every day is the gift of your time. And the best way to honor the gift of your time is to do your best. And there be times you won't be the best. But if all you did was the best, that's all you could do. And I remember one time, so I was a senior in high school. I've already gotten into Stanford. I'm totally psyched. I'm going to go last week of the semester of senior year. And I'm have a test the next day in English.
1:45:28And my dad's like, Hey, how are you feeling about the test? I said, it doesn't really matter. I get to drop it. And I'm going to get an A in the class because I've got, you know, I've got, I've got the goods, right? I don't, I don't need to do well on it. And he looked so disappointed at me. And, and he was like, you know, it doesn't sound like you're doing your best. And what he was kind of getting at was that, you know, the people who achieve greatness, they think everything counts. So I always got a lot from that with him. And there, there be other times where I wouldn't do so well on something.
1:46:06And he would, he would say, well, you know, sometimes you make a careless mistake or, you know, but you did your best. That's all you could have done. And so like the idea of doing your best, I find it be very profound. And it causes you to realize that the best way to show up in the world is to be the best your best self. There's only one you in this world. And the more that you can show up as your best self, you'll be impossible to compete with. You won't feel the need to copy other folks. You won't need the view, the need to compare yourself to other people. You'll compare yourself instead to the idea of perfection itself.
1:46:42And, and whatever that means in terms of your own ability to do your best. So I've always, to me, that's probably the most important life lesson I've learned. Wow. As you said, very simple, but very powerful. It's powerful when you truly internalize it, right? When you, when you take it beyond an aphorism, it's very powerful. It reminds me of your partner Ann Marie Kose advice that she got from her dad, which is I think maybe the opposite that she shared on Tim Veris' podcast of just always do a world class job, but everything you do, you're doing a world class job. Yep. Amazing. Okay. I'm going to skip the last question just to end on that because those way too beautiful to solely with another question.
1:47:26So just to give folks a chance to figure out where to buy your book when it's available, how to find it, what they should know. Do share. Yes. I guess there's two main ways, right? There's a, well, we've got a sub stack of not everybody's got to buy books, right? So there's a, paddedbreakers .substack .com. And then I, you know, I have a site paddedbreakers .com, but you can also get the book on Amazon or, you know, anywhere. It's already available for pre -order it. Amazing. And I usually ask people how listeners can be useful to you. Imagine it's, check out the book, share what you've learned.
1:47:59My main goal is for the ideas to spread and to help people. And so, you know, hopefully, hopefully it will have achieved that goal. But just anything that people can do to help spread the ideas. And I'm looking at co -conspirators wanted. I love these episodes where somebody like you spends hundreds of thousands of hours analyzing data and history and startups and talking to founders and just synthesizing all the things you've learned into a couple hours. I love this. Thank you, Mike, so much for being here and for sharing all this wisdom of this. Hey, well, thanks, Lenny. It's honored to be on your show.
1:48:34And, you know, it's been fun to see you do so well. Thanks, Mike. It's an honor to have you on the show. And again, the book is called Patternbreakers. Why some startups change the future? Mike, thank you so much for being here. Okay. See you, Lenny. Thanks. Bye, everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at Lenny's Podcast .com.
1:49:09See you in the next episode.
From the publisher
Mike Maples, Jr. is a legendary early-stage startup investor and a co-founder and partner at Floodgate. He’s made early bets on transformative companies like Twitter, Lyft, Twitch, Okta, Rappi, and Applied Intuition and is one of the pioneers of seed-stage investing as a category. He’s been on the Forbes Midas List eight times and enjoys sharing the lessons he’s learned from his years studying iconic companies. In his new book, Pattern Breakers: Why Some Start-Ups Change the Future, co-authored with Peter Ziebelman, he discusses what he’s found separates startups and founders that break through and change the world from those that don’t. After spending years reviewing the notes and decks from the thousands of startups he’s known over the past two decades, he’s uncovered three ways that breakthrough founders think and act differently. In our conversation, Mike talks about:
• The three elements of breakthrough startup ideas
• Why you need to both think and act differently
• How to avoid the “comparison trap” and “conformity trap”
• The importance of movements, storytelling, and healthy disagreeableness in startup success
• How to apply pattern-breaking principles within large companies
• Mike’s one piece of advice for founders
• Much more
Pre-order Mike’s book here and get a second signed copy for free. Limited copies are available, so order ASAP: patternbreakers.com/lenny.
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Find the transcript at: https://www.lennysnewsletter.com/p/how-to-find-a-great-startup-idea-mike-maples-jr
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Where to find Mike Maples, Jr.:
• X: https://x.com/m2jr
• LinkedIn: https://www.linkedin.com/in/maples/
• Substack: https://greatness.substack.com/
• Website: https://www.floodgate.com/
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Mike’s background
(03:10) The inspiration behind Pattern Breakers
(08:09) Uncovering startup insights
(11:37) A quick summary of Pattern Breakers
(13:52) Coming up with an idea
(15:30) Inflections
(17:09) Examples of inflections
(28:10) Insights
(36:58) The power of surprises
(47:36) Founder-future fit
(55:33) Advice for aspiring founders
(56:41) Living in the future: valid opinions
(55:34) Case study: Maddie Hall and Living Carbon
(58:40) Identifying lighthouse customers
(01:00:53) The importance of desperation in customer needs
(01:03:57) Creating movements and storytelling
(01:24:22) The role of disagreeableness in startups
(01:34:42) Applying these principles within a company
(01:40:43) Lightning round
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Referenced:
• Pattern Breakers: Why Some Start-Ups Change the Future: https://www.amazon.com/Pattern-Breakers-Start-Ups-Change-Future/dp/1541704355
• Justin.tv: https://en.wikipedia.org/wiki/Justin.tv
• Airbnb’s CEO says a $40 cereal box changed the course of the multibillion-dollar company: https://fortune.com/2023/04/19/airbnb-ceo-cereal-box-investors-changed-everything-billion-dollar-company/
• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach
• The Unconventional Exit: How Justin Kan Sold His First Startup on eBay: https://medium.datadriveninvestor.com/the-unconventional-exit-how-justin-kan-sold-his-first-startup-on-ebay-4d705afe1354
• Kyle Vogt on LinkedIn: https://www.linkedin.com/in/kylevogt/
• The State of Telehealth Before and After the COVID-19 Pandemic: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9035352/
• The Craigslist Killers: https://www.gq.com/story/craigslist-killers
• The social radar: Y Combinator’s secret weapon | Jessica Livingston (co-founder of Y Combinator, author, podcast host): https://www.lennysnewsletter.com/p/the-social-radar-jessica-livingston
• Michael Seibel on LinkedIn: https://www.linkedin.com/in/mwseibel/
• The Airbnb Story: How Three Ordinary Guys Disrupted an Industry, Made Billions ... and Created Plenty of Controversy: https://www.amazon.com/Airbnb-Story-Ordinary-Disrupted-Controversy/dp/0544952669
• Scott Cook: https://www.forbes.com/profile/scott-cook/
• Chegg: https://www.chegg.com/
• Aayush Phumbhra on LinkedIn: https://www.linkedin.com/in/aayush/
• Osman Rashid on LinkedIn: https://www.linkedin.com/in/osmanrashid/
• Okta: https://www.okta.com/
• The Man Who Makes the Future: Wired Icon Marc Andreessen: https://www.wired.com/2012/04/ff-andreessen/
• Peter Ludwig on LinkedIn: https://www.linkedin.com/in/peterwludwig/
• Qasar Younis on LinkedIn: https://www.linkedin.com/in/qasar/
• Paul Allen’s website: https://paulallen.com/
• Louis Pasteur quote: https://www.forbes.com/quotes/6145/
• What was Atrium and why did it fail? https://www.failory.com/cemetery/atrium
• Patrick Collison on LinkedIn: https://www.linkedin.com/in/patrickcollison/
• Drew Houston on LinkedIn: https://www.linkedin.com/in/drewhouston/
• William Gibson’s quote: https://www.goodreads.com/quotes/681-the-future-is-already-here-it-s-just-not-evenly
• Maddie Hall on LinkedIn: https://www.linkedin.com/in/maddie-hall-76293135/
• Living Carbon: https://www.livingcarbon.com
• Zenefits (now Trinet): https://connect.trinet.com/
• Sam Altman on X: https://x.com/sama
• Steve Wozniak on LinkedIn: https://www.linkedin.com/in/wozniaksteve/
• Horsley Bridge Partners: https://www.horsleybridge.com/
• David Swensen: https://en.wikipedia.org/wiki/David_F._Swensen
• Judith Elsea on LinkedIn: https://www.linkedin.com/in/judithelsea/
• 7 Powers: The Foundations of Business Strategy: https://www.amazon.com/7-Powers-Foundations-Business-Strategy/dp/0998116319
• Business strategy with Hamilton Helmer (author of 7 Powers): https://www.lennysnewsletter.com/p/business-strategy-with-hamilton-helmer
• Lyft’s Focus on Community and the Story Behind the Pink Mustache: https://techcrunch.com/2012/09/17/lyfts-focus-on-community-and-the-story-behind-the-pink-mustache/
• Logan Green on LinkedIn: https://www.linkedin.com/in/logangreen/
• John Zimmer on LinkedIn: https://www.linkedin.com/in/johnzimmer11/
• Storytelling with Nancy Duarte: How to craft compelling presentations and tell a story that sticks: https://www.lennysnewsletter.com/p/storytelling-with-nancy-duarte-how
• Steve Jobs Introducing the iPhone at MacWorld 2007: https://www.youtube.com/watch?v=x7qPAY9JqE4
• Jonathan Livingston Seagull: https://www.amazon.com/Jonathan-Livingston-Seagull-Richard-Bach/dp/0743278909
• The paths to power: How to grow your influence and advance your career | Jeffrey Pfeffer (author of 7 Rules of Power, professor at Stanford GSB): https://www.lennysnewsletter.com/p/the-paths-to-power-jeffrey-pfeffer
• Robin Roberts on LinkedIn: https://www.linkedin.com/in/robin-roberts-393a934b/
• Skunkworks: https://www.lockheedmartin.com/en-us/who-we-are/business-areas/aeronautics/skunkworks.html
• Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma): https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor
• Hard-won lessons building 0 to 1 inside Atlassian | Tanguy Crusson (Head of Jira Product Discovery): https://www.lennysnewsletter.com/p/building-0-to-1-inside-atlassian-tanguy-crusson
• Figma: https://www.figma.com/
• Atlassian: https://www.atlassian.com/
• Vinod Khosla: https://www.khoslaventures.com/team/vinod-khosla/
• Top Five Regrets of the Dying: A Life Transformed by the Dearly Departing: https://www.amazon.com/Top-Five-Regrets-Dying-Transformed-ebook/dp/B07KNRLY1L
• Chase, Chance, and Creativity: The Lucky Art of Novelty: https://www.amazon.com/Chase-Chance-Creativity-Lucky-Novelty/dp/0262511355
• Clay Christensen’s books: https://www.amazon.com/stores/Clayton-M.-Christensen/author/B000APPD3Y
• Resonate: Present Visual Stories That Transform: https://www.amazon.com/Resonate-Present-Stories-Transform-Audiences/dp/0470632011
• Ferrari on Prime: https://www.amazon.com/Ferrari-Adam-Driver/dp/B0CNDBN672
• Montblanc fountain pens: https://www.montblanc.com/en-us
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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.
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Lenny may be an investor in the companies discussed.
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