Welcome to Remarkable People. We’re on a mission to make you remarkable. Helping me in this episode is Mike Maples Jr.
Mike is a venture capitalist whose unconventional wisdom has led him to invest early in companies that transformed their industries.
As co-founder of Floodgate, Mike has developed a unique lens for spotting revolutionary companies before they become obvious wins. His portfolio speaks volumes – early investments in Twitter, Twitch, and Okta – but it’s his misses, particularly passing on Airbnb, that shaped his most valuable insights about innovation.
At the heart of our discussion was a counterintuitive truth: the best startup ideas often appear wrong until they’re proven unquestionably right. Mike articulates this through his concept of “inflection points” – those pivotal moments when technological or social shifts create opportunities for entirely new business categories.
Take Airbnb, which Mike initially passed on. The conventional wisdom said no one would want to stay in a stranger’s home. But that wisdom failed to account for how social networks and digital reputation systems would fundamentally change how we trust one another. It’s this kind of insight – seeing how inflection points reshape what’s possible – that separates truly transformative companies from merely good ones.
Throughout our conversation, Mike emphasized that startup success isn’t about building something marginally better than what exists. Instead, it’s about harnessing these inflection points to “change the subject” entirely – creating new categories where old rules don’t apply.
For founders and investors alike, this episode offers a masterclass in thinking differently about innovation and value creation in the startup world. Whether you’re building a company or investing in the next generation of entrepreneurs, Mike’s framework for evaluating opportunities will transform how you think about what’s possible.
Please enjoy this remarkable episode, Mike Maples Jr.: Inflection Points and Startup Success.
If you enjoyed this episode of the Remarkable People podcast, please leave a rating, write a review, and subscribe. Thank you!
Transcript of Guy Kawasaki’s Remarkable People podcast with Mike Maples Jr.: Inflection Points and Startup Success.
Guy Kawasaki:
Hello. I'm Guy Kawasaki. This is the Remarkable People Podcast, and we're in the business of helping you become remarkable.
We scour the globe for the most remarkable people, and we found a remarkable person named, Mike Maples Jr.
In the prelude we were just discussing, he and I go way back. In college he read my books, which is kind of a disturbing thing when people tell you that they read your book in college and now they're way out of college.
Anyway, he is a venture capitalist today. He's the co-founder of a leading Silicon Valley seed fund called Floodgate, and he has invested in companies like Twitter, and Twitch, and Okta. He's really one of the pioneers of seed capital in the mid 2000's.
With no further ado, Mike Maples Jr. welcome to Remarkable People.
Mike Maples Jr.:
Hey. Thanks Guy. I've been looking forward to this. I think I've probably known you much longer than you've known me because I've got to know you somewhat through your books when I was in college.
Guy Kawasaki:
Wow. Like I said, that's kind of a double-edged sword. Well, as long as you don't think that I wrote Rich Dad, Poor Dad, I call that a win, so I'm easy to please that way, Mike.
Mike Maples Jr.:
Yeah. I mean the ones I really remember in my formative years were The Macintosh Way, and then the other one was Selling The Dream.
I think in Selling the Dream, I was actually at Kepler's Bookstore when you launched it. I probably have a signed copy. One of the aspects of it I remember is I think it had the Macintosh product introduction plan in it.
Guy Kawasaki:
Yes. In the back.
Mike Maples Jr.:
At the time, I was a young product manager at Silicon Graphics, and you didn't really get trained in marketing back in those days. Everything I knew about marketing, it was just what I read in marketing books.
That was an actual introduction plan. I was like, "Hey, man, I could really learn something from this." Then reading your books led me to Regis McKenna and some of his work. I always thought that he had some really good ideas around relationship marketing and how do you evangelize ideas.
Yeah. I feel like I've probably known you, hopefully I don't seem like a stalker, but yeah. I've known you since you were CEO of ACIUS.
Guy Kawasaki:
Wow. Man, you're going back. You're going back so far. I was young.
I loved your book and I see so much stuff that I agree with in your book and let's start with something very basic. Your book is all about getting these inflections and getting insights from the inflections and turning it into ideas.
Let's start with a definition to help everybody. What exactly do you consider an inflection?
Mike Maples Jr.:
Yeah. An inflection is a change event that's actually external to a startup or any business for that matter. It allows a startup capitalist to compete by changing the subject.
What I like to say is that in startups better doesn't matter because business is never a fair fight. If you're a startup, you have to have some form of weapons to wage asymmetric warfare on the present. You have to turn the incumbents greatest perceived strengths into their biggest weaknesses.
The way entrepreneurs do that is they harness inflections. They use inflections to bend the arc of the present to a radically different future. By doing that, they deny the premise of the rules of competition. They show up seemingly out of left field, and now all of a sudden they disorient the incumbent.
Airbnb did this in hospitality, and Twitter did this in blogging and communication, but nobody ever, when they saw Airbnb said, how does that compare to Four Seasons? Nobody, when they saw Twitter said, how does that compare to WordPress? It stood alone as an entirely new thing.
I like to say better doesn't matter when you're a startup because if you're better, then the customer's going to have an alternative to your startup. Why would they pick your product when you're 80 percent likely to go out of business?
They're only going to pick your product if it can't be reconciled with anything they've ever seen before. If they say, oh my gosh, where have you been all my life? The way that the founder achieves that goal is they harness inflections. They use the power of inflections to offer something that would seem unthinkable before the inflection happened.
Guy Kawasaki:
But Mike, do inflections cause companies to succeed or do companies cause inflections to succeed? Which way does it flow?
Mike Maples Jr.:
Yeah.
I like that question, and it is one of these kind of recursively existential questions too. The way I internalized it was I was like, "Okay, what should founders care about?"
What I thought was, okay, founders need some type of a power to change the subject. When I think about an inflection, whether the founder caused it or leveraged it, what matters, I think from the founder point of view is three things.
One is just what is the specific empowerment? Does it offer something that can provide a TenX benefit or something radically unique that's never been seen before? Or is it just an API call that got added to Stripe's API list?
A good example of an inflection would've been, that was empowering was the iPhone 4s had a GPS chip in it. You could have had the idea for ride-sharing before the iPhone 4s, but it wouldn't have mattered because you couldn't have implemented a system that embodied that idea.
Now all of a sudden you have a GPS chip in the phone, you can locate riders and drivers with an algorithm. That's an example of something very empowering.
The second thing we want to see in an inflection is who does it empower? Who cares? In the case of the iPhone 4s, a lot of people care because a lot of people have smartphones. The potential surface area of the empowerment is very high because if you believe that smartphones will keep happening and they'll keep having GPS chips in them, then potentially that's hundreds of millions if not billions of people someday.
Then the third aspect of the inflection is I call it the empowerment conditions. We've had nuclear power since the 1940s, but we haven't built a nuclear power plant in the United States since the 1970s. Just because you have a power doesn't mean you're going to use it or be allowed to use it. There might be political factors. There might be trust factors. There could be a lot of reasons that people don't decide to adopt it.
Those are the three things I look for. What's the magnitude of the empowerment? Who does it empower? Under what conditions will people decide to take advantage of it, and under what conditions will they decide not to?
If you can get all three of those things going your way as a founder now it's kind of like a rock in David's slingshot against Goliath. Now, you have something that you can bring to the party that changes the subject.
Guy Kawasaki:
When I read your book and I read that concept, I thought to myself, oh my God. This is such a high fence. In a sense you're saying that every successful startup either caused or significantly jumped on an inflection.
I got to tell you; I see a lot of startups that I would hardly affiliate them with truly an inflection.
Mike Maples Jr.:
Yeah.
Guy Kawasaki:
Are you that tough?
If somebody shows up at Floodgate and they just have something better, better, do you just throw them out the door?
Mike Maples Jr.:
Well, I don't throw them out the door, I wish them well, but what I say to them is, "Look, do you want to pursue an idea that has outlier, unbounded upside potential or not?" If you're not harnessing an inflection in your startup idea, you're competing in somebody else's sandbox.
The mistake most startups make is they say, "I want to go after big market." That makes sense on the purpose because big markets have lots of customers and revenue, but the problem is that the founder often unwittingly buys into a context which is the market as it's defined as the market.
If the market's already defined, then somebody's defined it. That person has the advantage over you because they get to define the discussion that occurs, and they already have the advantages of the incumbency.
Therefore, it's like if you're competing over territory that's a tiny little municipality in an already discovered city. You you're not going to have as big of an upside as if you're Lewis and Clark mapping the Louisiana Purchase territory and discovering the undiscovered land.
I'm not interested in the total existing or total available market. I'm interested in the total future market. I'm interested in a product that defines a future market because it harnesses these inflections.
I just say to a founder, "Hey, look, I'm not for everybody, but that's what I'm in it for. I'm trying to find startups that harness these inflections in unconventional ways to create a product that radically changes how people think, feel, and act." To me, that's where the startup wins is when they do that.
There's two ways to look at the future. Do you believe it's going to be a new and improved version of the present, in which case the incumbents are going to usually win that? Or do you believe that the future's not going to be able to be reconciled with the present, in which case the startup can win?
By the way, you work for a guy who was the master at this, and he did it even in a big company. Steve Jobs, when he comes back to Apple, everybody says, "Hey, you should license the Mac OS and run it on Intel, and you should have a clone market just like Microsoft and IBM do," and all this stuff. Jobs didn't do that.
Jobs always found a way to change the subject. With the iPod, he found this inflection in the sense of a tiny little hard disk that he could put into a music player. With the iPhone, he waited until the technology was ready, that the touchscreen was good enough, and that the power in the phone was good enough that he could put Mac OS in a phone device.
Jobs never competed by being better at something. He always competed by showing up with something radically different and helping the rest of us understand what was important about it. He did that by harnessing inflections. He just naturally knew how to do that because he knew that was his weapon to sort of change the discussion.
Guy Kawasaki:
Let's talk about what I consider maybe the biggest inflection certainly in my career, and I might argue in the history of mankind, which is artificial intelligence.
It seems to me that I use ChatGPT, I use Claude, I use Perplexity, I use four or five LLMs. For the life of me, I cannot tell you why I use one over the other.
If you were to talk to the CEO of Claude or Perplexity and you would tell them like, listen, you're just doing something better. Maybe your model is better or something, but you are not fundamentally changing.
How does Perplexity or Claude compete against Gemini in Google? I just don't see how they differentiate.
Mike Maples Jr.:
Yeah. It's interesting, and I love this question because it highlights a real challenge I think right now, which is, yes, you want an inflection, but you also want to have an insight, and it's not enough to just have a powerful idea. If a whole bunch of other people have that same powerful idea, then the opportunity gets somewhat competed away.
You want to be non-consensus and right. If we go back to the example of Lyft, and then we can relate it to AI I suppose. The iPhone 4s had an inflection in terms of empowering people to locate riders and drivers, but the founders of Lyft and Uber had to have the insight that, oh, that means you could create a transportation network that has network effects. That's where the creativity of the founder comes in.
Now it's obvious. Now people are ride-sharing of course, but at the time it seemed crazy. Who's going to get in a stranger's car? Nobody's going to do that. That's crazy. Just like who's going to stay in a stranger's house? That's crazy.
Most of the great startups, they have to have an insight because if human beings are conditioned to things, and so if everybody likes your idea, it's too similar to what they already know, which means it's too much of an incremental improvement. It's too much competing on better versus different.
The best startup ideas I've seen have this quality of most people don't like it at first or don't think it's going to work, or they think it's irrelevant, but there's a small subset of people who are like, "Oh my gosh. Where have you been all my life? I've seen the light. This is amazing."
You want that. You want to be non-consensus and right. It's not enough just to be right. You have to be non-consensus and right.
Back to Perplexity and Claude and these guys, I don't really think of them as startups in the way that maybe you and I think of startups. The way I think of Perplexity and those guys is I think of them more as small versions of big companies. If I think about those companies, they're not really trying to in a capital efficient way, create some asymmetrically radically difference.
They're partnering with the big tech companies to create scalable technology. I think it just happens to be that right now, small versions of big tech companies, but I don't think of ChatGPT and Claude and those guys as startup capitalists. I think of them as probably someday a large division of a big tech company. We just don't know which one yet.
Guy Kawasaki:
In a sense, even though what they do is so exciting, it sounds kind of boring when you put it that way.
Mike Maples Jr.:
I think what they're doing is great. I just don't think of them as startup people in the same way that I thought of the Lyft guys or the Twitter folks.
I think of them as more back in the day when you'd have these joint ventures between IBM and Apple or when you'd have big companies spinning off divisions and stuff like that. I think of it as more like that than I think of it as classic startup capitalism.
Guy Kawasaki:
With all this talk about the entrepreneurs, the true entrepreneurs who are creating or writing this inflection point, I guess my big question for you, Mike, is how do you separate the nutcases from the pattern breakers?
At the time you hear some of these pitches, you must think these people are nuts. Then five years later you say, oh, they were so right.
How do you figure that out? Who are the nutcases and who are the breakers?
Mike Maples Jr.:
Yeah, and it's funny, some books are born of experience, and competence, and expertise. This book that I wrote started more out of embarrassment.
I had passed on Air Bed and Breakfast, which became Airbnb, and I would've made thousands of times my money if I'd done it. Then I noticed that 80 percent of my exit profits had come from pivots. Twitter had started as a podcasting company called Odeo. Twitch had started out as a terrible idea called Justin.tv.
I'm looking at this and I'm like, what business am I even in here? What am I doing? Am I just throwing darts? Should I just retire before I get exposed? What I started to realize was that these startup ideas that were working, they were harnessing inflections and they were non-consensus and right.
Now, here's the tricky part, and it gets to your question, I think, which is when you're non-consensus and right, you don't know that you're right at first. You only know that you're non-consensus. If you knew you were right, it would be too obvious.
The less obvious it is, the less you can know for sure that you're right. On some level, you have to try the idea. You have to decide, I don't know if I'm 100 percent right yet, but this is a non-consensus area that's worth pursuing. It's worth my energy and time to figure out. If I'm not 100 percent I might pivot.
How do you tell the difference? What's the right kind of crazy? What's the wrong kind of crazy? The question I like to ask is this from the future?
I think William Gibson, the Cyberpunk author was right when he said, "The future's already here. It's just not evenly distributed." For example, when Mark Andreessen worked on the Mosaic browser at the University of Illinois, he was in a supercomputer lab with a really fast network and powerful computers.
His idea of what networks were going to be was a better version of the future than Microsoft's top down, or AOL, or the US government, or AT&T, or Time Warner's view of a tops down network. I think that the way that a non-consensus idea is worth pursuing is the authenticity of the founder to that future that they're pursuing.
I think that if you're living in the future before other people and you're harnessing powerful inflections before other people, the odds that you're going to build the right thing are much higher to be correct. That your intuition about what to build is far more likely to be right.
That's what I really look for. Is I want to know, is this founder living in the future for the rest of us? Are they intrinsically motivated by that future? Are they just pursuing what they think is hot? Do they have insights about what to build because of authentic obsession with that future?
I believe that, that causes you to be more likely to build the right thing, but it also makes you more credible to early believers. It causes other people to say, "Hey, I agree. This Guy Kawasaki guy with this ACIUS relational database here. I think he's noticed something that others haven't noticed and I want to join that movement."
I remember this from when you were a founder. I think in your database at Fourth Dimension, tell me if I'm wrong about this, but your contacts, you would have a tag next to them. One of the tags was like, "True believer." Joe Lemont, my roommate college, you had tagged him as a true believer.
That's like these early startup markets are animated by belief, not utility. People buy from startups for aesthetic reasons, not practical reasons. They do it because they co-create the future with the founders. It's the early believers that do that with the founders and it's the belief in a different but aesthetically superior future that drives people to move the present to a different future together.
That's what I'm looking for. I want the idea that's non-consensus, but I want believe that the person comes by the idea honestly. That they come by it by authentically pursuing a future that I can get behind.
Guy Kawasaki:
Today in artificial intelligence, do you have any examples of this non-consensus kind of inflection idea?
Mike Maples Jr.:
Yeah. I'd say that AI has been really challenging for me because I see inflections every week, but now if somebody shows up and says, "I have this great idea," and I'm like, "I would totally use that product, but I don't know why there's not going to be ten just like it," which means it doesn't have enough of an insight. I'll give you an example of one that I think does.
I'm involved with this company called Applied Intuition, and they make autonomous vehicle simulation software and software-defined platforms for the car companies.
Let's say your General Motors or Porsche or you're one of these big car companies, Tesla has a software defined car, and you don't really know how to build it and you don't really know how the electric vehicles are more like a software platform architecture. Versus a supply chain with a bajillion suppliers that you've all done business with for fifty years.
Qasar Younis started this company with some friends of his from Google. They'd grown up in Detroit. Qasar had worked at General Motors after graduating from undergrad, then he went to Silicon Valley. Was at Google for a while. Worked on Google Maps team. Knew all the guys at Waymo.
He can go to the CEO of a company like Porsche and say, hey, if you want to have a software defined car, I'm your only path to getting there. You don't have the internal talent. I have the best developers in the world tackling this problem, and you can only get this talent if you do business with me.
Now, is Sam Altman going to release a new version of ChatGPT that does that? No, because he's not in the business of creating software defined cars. Those are examples of businesses I like because it involves deep technology, but it involves a multidisciplinary approach.
You have to not just be good at the AI, but you have to be able to speak the language of the car companies, and you have to be able to implement systems at Global Enterprise scale, and help the customer reach the promised land. It's very strategic to these car companies. They know they have to move in the direction of being a software defined car.
That's the kind of stuff I've been seeing lately that I get excited about.
Guy Kawasaki:
What if somebody says, there's only twenty-five major car companies in the world. How big is the market, Mike?
Mike Maples Jr.:
Yeah. In that case, you have to be able to get giant contracts. You have to have individual customers in the hundreds of millions of dollars to make that business work, but you can.
Bosch doesn't have that many customers in the car industry, but they probably do about fifty billion dollars a year selling to the car companies. If you become the complete answer to something that company cares about, you can do pretty well. Companies aren't just going to give a hundred million dollars to just some bozo, right?
They're not going to give you a giant contract unless they think you can really do the job and you're the only guy that can do it. You have to have a particular set of skills that people buy into or it's going to be hard.
Guy Kawasaki:
I don't want to really catalyze PTSD in you, but can you discuss the cases where you had a false positive? In other words that you thought someone was a pattern breaker, but after all didn't?
Mike Maples Jr.:
Oh, sure. In fact, it's most of the time.
My business is very strange. Warren Buffett, I've heard him say, "Rule number one, don't lose money. Rule number two, don't forget rule number one."
For me, rule number one is don't pass on Airbnb. If I'd been wrong about Airbnb, I could only lose 100 percent of my money, but if you're right, you can sometimes make a thousand times or more.
Buffett talks about his margin of safety. What I care about is my margin of asymmetric upside. I care about how big could it be in the rare event that it works.
I have this really weird way of coming up with an investment thesis. I'm like, "Okay. Given that it's 80 percent likely I'm wrong, how big does it need to be if I'm right?" If it can't be big enough, no matter what the odds are, I just can't invest in it because I have to get paid for the risk I take.
I'm taking crazy high risk. I'm like unlike say Buffett, who never wants to lose money I'm saying to myself, "Okay. Given that it's 80 percent likely I'm going to lose money in the 20 percent case, how big does it need to get?" Which is just a different way of showing up in the world. It's a different way of thinking about success.
I don't look at risk as the chance of success or failure. I think of risk through an expected value lens. I'm like, "Okay, in the 20 percent case, it's right. How big does it need to be a good expected value bet, even though it's risky?"
Guy Kawasaki:
What if at the moment of making an investment, it's really not an assessment of how big can something be because you don't know what this company's going to pivot to?
When you talk about Justin.tv you couldn't do an analysis of how big Justin.tv would be. When Justin.tv pivoted to Twitch, then you could, but that wasn't at the point of investment. How do you factor in the pivots?
Mike Maples Jr.:
Yeah, and so the way I do it is I like to say I don't want to study the total addressable market for the reason that you mentioned. What I believe is that companies that harness inflections define new markets. I can't size a future market. The future hasn't happened yet.
What I need to do is it reminds me in physics you have potential energy and mechanical energy. What I'm looking for is a future potential market. I believe that big future potential markets happen from powerful inflections.
The more powerful the inflection is, the more capacity it has to change the future and the more capacity it has to impact the future in a broad way. What I do is I take a leap of faith. I say, "Based upon this inflection, based upon this insight and based on the founders authentic match to the future they're pursuing, I think the odds are in my favor."
I don't have to know exactly how the dots will connect. I only have to think that the odds are highly probable that the founder will find a way to connect those dots. I love this Job saying, "You can only connect the dots looking backwards," and I think that's what he was getting at.
You're pursuing opportunities that are ambiguous, but that doesn't mean they're not a risk worth taking. If you're betting on the founders ability to navigate their insight to the right product proposition.
The example that you gave with Twitch, Justin.tv's a terrible idea, but they navigated the idea to Twitch, which was a great idea. The inflections, the underlying inflections were always there from the very beginning.
Guy Kawasaki:
Now what about false negatives where you turned down somebody, they turned out great. What have you learned about why you made false negative decisions?
Mike Maples Jr.:
Yeah. To me, those are the biggest errors in my business. Passing on Air Bed and Breakfast at the time was a terrible idea. I've passed on other good ones too. We passed on Pinterest early. We passed on a company called Anaplan. Passed on Figma.
Whenever we pass on these, in fact, whether I saw them or not, I keep this database of, I call them a hundred bagger startups. I have this list of little over a hundred companies and I study them. I create a time capsule of what it looked like at the seed round.
I have the seed deck from Pinterest, and Dropbox, and Airbnb, and all these companies. I look at it and I say to myself, "Okay, where was the signal? What was the thing that would've told you to say yes? And why did I have a failure of imagination and say no?"
With Airbnb, my failure of imagination was I thought people aren't going to want to stay in a stranger's house. That's crazy, right? It was around the time that Craigslist killer. I was like, somebody's going to get killed in one of these things.
It was a screwed up meeting. Brian couldn't get the site to work in our meeting. He had a room full of cereal boxes. He was trying to sell me Obama O's and Captain McCain Crunch. That's the other thing I learned is sometimes the pitch doesn't go well, but that doesn't mean it's not going to succeed. I try to go back in time.
The other thing I've learned Guy, is that even the founders misremember how it happened a lot of the times. When it works, everybody remembers the stuff they knew and the good decisions they made, but a lot of times they know things that weren't so at the time.
You have to be almost like Joe Colombo detective. You do a forensic analysis of what it looked like at the time. Then you got to ask yourself, do any of the frameworks that we use to evaluate these things, would they have been useful here? Would they have caused us to say yes? Or are we just breathing our own fumes? Do we believe a bunch of stuff about what's true in the world that just isn't true or doesn't capture the reality of this situation?
That's what I try to do. I try to go back in time and really understand it. There's a lot of things you can do to understand it. You can look at the initial seed pitch deck and you can say, is that what the product ended up being? Or did it end up being something different? How long did it take for them to get to a million revenue, ten million, a hundred million in revenue?
What caused that? What kind of business model was it? What was the defensible moat that they created? You could start to look for the signals that would've clued you in that, hey, this is a bet we're taking.
Guy Kawasaki:
I have not done what you just described in any form as organized, or rational, or careful as you, but my conclusion, the more I am in Silicon Valley and around tech startups, my conclusion is coming to that the older I get, the less I know.
I could almost make the case that you should just invest in the stupidest things that come across your deck because that's the ones that's going to succeed. I cannot figure this out.
I would've never invested in, as you say, you're going to let a stranger stay in a house. You're going to let a stranger rent your car. You're going to let a stranger ride with you. You would get in a stranger's car, get in a stranger's house, you would take a stranger's tour or rental. I would do none of those and look at that. I'd be zero for three right there.
Mike Maples Jr.:
Yeah, it's tough. It's a humbling game for sure.
The other thing about it Guy is massive success is one Airbnb away. You get one of those every ten years, you're really good. It is a humbling game, but for me, it's just so darn interesting.
We know a whole lot about business now, but a hundred years ago there were no org charts, and there wasn't accounting, and there wasn't corporate strategy as we know it. There wasn't Michael Porter’s Five Forces. There wasn't any of this stuff. All that stuff had to be figured out. I think we're at the beginning of infinity of really understanding startup capitalism.
I just think a startup capitalist is a different type of capitalist. They don't create value by persistently compounding an advantage like a big company does. They create value by doing something radically different, and that's another way to show up in the world and be valuable.
I just think there's so much to learn about that. I think that just like there's a process for building a great company that's a growing concern, I think that there are processes and patterns that can be understood about what it takes to create a great startup that changes the future. There's so little that's known about it.
We're having this conversation right now. It seems kind of random. It seems like trying to predict the weather or something, but to me, that's what makes it so interesting. Is it's so hard to figure out that it's worth trying to figure out.
Guy Kawasaki:
I tell you, Mike, as I get older and older, my strategy is get lucky, but get lucky is not a good strategy.
Mike Maples Jr.:
That's pretty good sometimes.
Guy Kawasaki:
I'm going to take you down a rat hole and you can tell me; we don't want to go down this rat hole, but you have the data to know these people better than most people.
I look at the current Mark Andreessen, the current Elon Musk, the current Mark Zuckerberg, and I asked myself, what happens to these people?
These people started off trying to make the world a better place, democratizing, computing, freedom of information, all that, and now they turn into these MAGA people and you got any thoughts about what happens?
Is it age or is it when you start being worth a billion dollars or more or something just happens in you? What happens to these people?
Mike Maples Jr.:
Let's see. I'm going to tread carefully on the political questions.
Guy Kawasaki:
Why?
Mike Maples Jr.:
But I guess we could talk about it some.
One thing that I've observed in a lot of these folks is that they tend to be disagreeable. When you think about it, a startup is a fundamentally provocative act. It's a disagreement with the present.
You're showing up as a founder and you're saying, hey, the way you think the world is, I'm challenging that. The way you think the world is. That's not how it's going to be. It's not going to be about taxis anymore. It's going to be about ride-sharing. It's not going to be about cars with drivers. It's going to be autonomous vehicles. It's not going to be gas ice cars, it's going to be electric vehicles.
Yes. I am going to start a company that blasts rockets into outer space. Even though my competition is the US government and they have an infinite supply of money that they can print.
These people tend to be disagreeable and by that I don't just mean being a jerk. They tend to just be willing to disagree. Justin Conn, before he started Justin.tv, he started a calendaring company, and Google launches Google Calendar. Justin decides to sell the company on eBay.
I was like, I didn't even know it's possible to sell a company on eBay. Sold this thing for 250,000 dollars. Some of the disagreeableness is just the willingness to be unconventional in how you pursue your ideas and your mission.
I think that Elon is naturally disagreeable. There are aspects of disagreeableness that people don't like, but if you make the diamond not have the properties of the diamond, it won't cut glass anymore.
I think that most of these people who create these outlier results, they're not normal people and they're not normal in ways that change the world for the better. They're not normal in ways that some people may not like, but like Elon said on Saturday Night Live that time he said, "I blast rockets into outer space, and I'm trying to change humanity. Did you expect me to be a normal chill dude?" Well, he's just not going to be. That's not who he is.
I've kind of learned that these people don't end up fitting neatly into a box that you wish they would fit into. I imagine that you've known some founders. You knew Steve Jobs way better than I ever would've, but I imagine there were things that Steve did that probably maybe you wish he didn't do. Is what it is. It comes with a territory.
Guy Kawasaki:
Okay. That's one of the great mysteries to me about why have they taken this attitude, but we'll drop this subject now.
I want to end up with just a quick series of questions. I'm assuming that many entrepreneurs are going to listen to this podcast and you're a legitimate successful VC. They probably would love to be in front of you. Just some quick questions. Very tactical and practical for an entrepreneur.
Question number one is how do people get to a VC? Do they send out 2,000 emails? How do people get to you?
Mike Maples Jr.:
The best way is to get a referral from somebody that we respect, and people tend to trivialize that discussion. People tend to say that just means that whoever has the best network wins, and there's going to be certain people who get excluded from being entrepreneurs. There's a reality Guy, which is if you're starting a startup, you have to convince people to join your movement.
If you're sitting out there in the future by yourself and nobody joins your movement, that future is not going to happen. To me, it's not a function of how well-connected you are. Getting an intro from someone I respect is a function of your ability to persuade somebody credible that your future matters and that other people are going to want to join you in that future.
Yes. Something could come over the transom, but how am I supposed to know? How am I supposed to know how good they are? I've got to find some way to validate that their ideas about the future make sense to credible people.
By the way, it doesn't have to be like Reid Hoffman or Mark Andreessen that makes the intro. It could be you're living in a certain future in synthetic bio, and it's a scientist who's very credible in that area. Is like, this is one of the most amazing things I've ever seen.
I just need some signal from the future that's valid. That validates the idea and the insight. I'd say that's the key thing.
If your insight is starting to get traction, that should be a solvable problem. There should always be somebody credible who embraces the idea. Who will make the intro. I'd say that's the primary thing that we look for.
Guy Kawasaki:
Okay. Next question. What do you want in the pitch? What's the content of the pitch?
Mike Maples Jr.:
Okay. Yeah.
I'll give some super tactical advice on that. All things being equal. I like to say slide number one, say what you do as if I know literally nothing.
You don't say, we're Airbnb. We're a marketplace for unused residential housing space. I don't know what that is. That's jibber jabber jargon.
What you want to say is something like, we're Airbnb. We let you rent an extra room in your house, and here's why that's important. A lot of times you'll get a pitch and you're ten slides in, I don't know what the startup does still. That's hard to process.
I'm sympathetic to founders on this front because they get advice. They get bad advice. They get advice that says millennials are a thing. Put that slide up front. Marketplaces are a thing. Talk about marketplaces, and I'm ten minutes in, I don't know what you do yet. Slide number one is what do we do as if I know nothing.
Slide number two is what do I know about the future that's not obvious? It's really your chance to convey the insight.
Slide number three is anything impressive that's happened so far objectively, customers, patents, letters of intent, just some proof that people in the world care about this thing and that they're joining the movement and signing up.
What I find is if the founder can get those three things quickly, ten minutes in, now the venture capitalist is leaning forward. Now, it's funny, I think we riffed on this earlier. What happens too often is founders get bad advice and so they create what I like to call a Franken Deck.
What happens is they'll pitch their advisor and the advisor wants the best for them. They'll say, hey, VCs love marketplaces because they have network effects. Don't say you rent an extra room in your house say, we're marketplace for residential real estate because marketplace hot network effect. Let's get the real estate big. Okay, put that in there. Then the founders say, "Oh yeah, you're right. Okay, I'll do that."
Then they'll say, "The other thing is this is an appealing service for millennials." So you should have a few slides up front that talk about the importance of millennials and handcrafted experiences, all that stuff. You haven't talked about the total available market yet. You ought to talk about that. You need a few slides on that. You need a few slides on the real estate market.
Guy Kawasaki:
You need AI in there too.
Mike Maples Jr.:
Today you'd say you need AI.
Then what happens is you go in with this deck of twenty slides and you pitch somebody, and the VC passes partly because they don't know what you do. Then they give a reason in their pass note for why they passed and it's like, oh man, there's another objection. I better have a slide that counters that objection.
Before you know it, you have thirty slides, each of which is designed to anticipate and counter an objection. What I like to say to founders is the only people that matter are the people who believe your insight.
If a VC doesn't believe your insight, they're not going to invest. There's no way to overcome their objection. They're not going to invest no matter what until it's proven.
What you want to find is the subset of people in this world who believe what you believe. That's true of customers, it's true of investors, true of early employees. Don't waste any urges of energy on anybody else.
The problem with the Franken Deck is the person who was ready to believe doesn't know what you do because they got confused by just how convoluted the pitch was. That person was going to be much more likely to say yes.
If you just show up and say, "We let you rent an extra room in your house, you're going to be able to do this because Facebook Connect. Let’s hosts and guests know who each other are, and people are used to online reviews, and everybody's connected, and millennials want these kind of experiences," and all that.
That's the conversation you need to have with the person who's prepared to believe and the person who's not prepared to believe doesn't matter because they're not going to do anything anyway. Their opinion doesn't matter either. This is the important point.
The source of their objection doesn't matter because they're not going to join your movement. Only those who are prepared to join your movement have valid input about your strategy. That's really important I find. Is to say, hey, I'm only going to spend time with the people I think are ready to move with me, and I'm going to bias my feedback collection to what they say.
Guy Kawasaki:
I got to tell you, Mike, I got to believe that many entrepreneurs listening to this, their heads are basically exploding because they've been hammered, and I got to take feedback. I got to check off all the boxes and I got to do all this.
Basically you're saying you got them in three slides, and if you don't get them in three slides, you're never going to get them. Just cut your losses. Stop wasting time and go find somebody who does believe the three slides.
Mike Maples Jr.:
I think so and some people may disagree with me here, but when you think about it, it’s inspiring. When you realize that great ideas are usually disliked by most at first.
By the way, that's true of everything. That's true of Euclidean Geometry. Copernicus, when he says, "The sun is at the center, not the earth." Well, The Pope puts him under house arrest and says, "Hey, maybe you ought to change your opinion about that."
People, when Einstein proposed the General Theory of Relativity, they're like, "This guy sounds like he's smoking weed. That's one of the most abstract, crazy things I've ever heard." Most great ideas are heretical at first and actually, if most people don't like your startup idea, that's a positive sign.
If everybody likes your startup idea, it's too incremental. When you realize that it's inspiring, right? When you realize, hey, given that most people are going to dislike my idea, who cares about them. They don't matter. They're not creating the future. I am. I and my early believers are going to create the future. They're not going to have a say in it. I need to go find who those people are and not waste a single erg of energy on anybody who's not those people.
What we want to do is we want to find the people who say, oh my gosh. Where have you been all my life? This is amazing. I can't wait to join your call to adventure and go do this with you. That's what you're looking for.
The people who aren't ready to accept your call to adventure, their objections don't matter because they don't apply to your adventure. The only objections that matter are the objections from fellow believers because they help you see the future in a more clear way.
Guy Kawasaki:
Mike, I have more questions, but there's no question I'm going to ask that's going to elicit an answer that is a better way to end this podcast than what you just said.
Mike Maples Jr.:
Okay. I like it.
Guy Kawasaki:
I call this the casino theory, and I often apply it to surfing. I'll tell you the casino theory of surfing and podcasting.
Sometimes when you go to Las Vegas and you have fifty dollars in your pocket, you go to a casino and you bet it on blackjack, or craps, or whatever, and just magically you have 500 dollars. My casino theory is that most people have that 500 dollars and they keep playing until they lose it. If you are smart and you got lucky, you got 500 dollars you walk out, right? You quit gambling, you walk out with the 500.
The casino theory of surfing is after you caught a great wave, don't try to keep catching waves. You're just going to get disappointed. The casino theory of podcasting is when you had a great answer like that.
You don't ask more questions. You just quit now and you end the podcast because that was a great answer. All these entrepreneurs around the world, they're putting pieces of their brain back in their head because you just said something that's contrary to what they've heard for the last two years. That's the way to end this podcast, Mike.
Mike Maples Jr.:
All right. I appreciate your taking the time, Guy, and it is great to see you and congrats on all the success you've had in many types of ways and scenarios. You've been a polymath when it comes to the tech industry. It was great to see you.
Guy Kawasaki:
I wish I could say that I caused or really capitalized on inflections as much as some of the stories that you wrote about.
Actually, if I think about it, the start of my career, I got on the Macintosh inflection, and at the end of my career I got on the Canva inflection. I got to tell you, in both cases, I consider myself lucky, not smart.
Mike Maples Jr.:
Yeah and it's interesting, probably you don't want to sell past the order like what you said. You want to end on the right note, but the other thing about this surfing thing is if you go after the right waves, you only have to be right once.
That's the way I look at it is you want to pursue opportunities where you only have to be right once because you'll be spectacularly right. The only way to really lose in entrepreneurship is to lose your time pursuing something that you realize in hindsight wasn't worthy of your talent and time.
We want to go after ideas that are waves that are worth surfing because like you said, "If you catch the ideal wave, you did it."
Guy Kawasaki:
Thank you, Mike. That was just a remarkable interview.
I'm Guy Kawasaki. This is Remarkable People and all you entrepreneurs who just had all your myths exploded, I empathize with you, but better you hear it now from Guy and Mike than you hear it two years from now after all these rejections and disappointments.
That's how to be a remarkable entrepreneur. I want to thank the rest, the Remarkable People Team. That's of course Madisun Nuismer, producer, Tessa Nuismer, researcher, Luis Magaña, Fallon Yates, and Alexis Nishimura.
We are the Remarkable People Team, and we are hell bent for leather on a mission to make you remarkable.
Until next time, mahalo and aloha.
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