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Mike Maples Jr is the co-founder of the Venture uh Capital firm Floodgate he's written a new book pattern breaker is
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why some startups change the future and let me say I was just telling Scott a second ago you're one of my favorite
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people to talk to because you're so smart you always given me good insights and although at the same time with many
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VCS it's a low bar um so uh but I've always appreciated your insights it was always different and unusual so let's
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just get into it just for people don't know you were an early investor you've always been a very earli investor in
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Twitter uh when it was Odio twitchyt and many others what exactly defines a founder or company as a pattern breaker
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I mean that's why why' you call your book pattern Breakers now I I'll give an example that's not even in the startup
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realm but it would be a pattern breaking example of recent times the Tesla cyber
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truck now you may like it you may dislike it when I saw it announce I thought he might be joking right like I
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I was like is he really going to ship that thing but nobody when they see a cyber truck ever says well so how does
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that compareed to an 150 so Elon kind of says live in my future or don't but you
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have to choose uh so pattern breaker is the idea was that we tend to operate according to consistent patterns and
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that's actually not a bad thing that helped helped us avoid saber-tooth tigers or it helps us fit in socially in
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communities and stuff but but pattern break pattern matching uh creates a bias as well it causes you to not not see
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other other opportunities this is a quote from you the right amount of disagree ableness can be a Founders Ally
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in developing breakthrough ideas now at the same time it can lead to toxicity you mentioned Elon he was he was very
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disagreeable but it's morphed into toxicity now right in a way that's everything is disagreeable right talk
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about that balance because I agree with you you know I I think I'm a disagreeable person I think it's one of
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the reason I'm successful because I disagree no but I go I'm like I want to do podcast now 10 years ago this is what
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I even though and a lot of people said no anything don't say anything sh sh sh shush um but we talk about this
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disagreeableness and when it becomes kind of you know I was right before and you'll see that I'm right again because
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it's not always the case for sure yeah so um so I'm going to tread carefully on this question because uh my uh you know
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I'm I'm a little bit more positive on Elon than you might be yes I know that um so so like the way is VC looking for
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his next deal what what VC out there with a fund open is critical of Elon Musk okay well let me so I haven't
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invested I'm sure your fondness for him is is is genuine anyways go ahead so so let me just let me just kind of descri
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like one of the things that I try to do and and you know there are trade-offs to
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it is I try to keep my tribal affiliation small so because like Elon contains multi multitudes sure does and
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and you know like if you look at um at at Nasa versus SpaceX to to to launch a kilogram
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uh SpaceX can do it for a 20th of the price right and and so I say okay I'm pretty interested in that right like I I
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like I'm I'm I'm glad that that that part of him exists in the world and then when I look at um when I when I look at
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what he's done you know to enable starlink over the Ukraine and so there there's like there's things about him I
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wouldn't do those things but but I try to I try to kind of separate you know the things that he does are really
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positive uh and and not try to like paint him with one single negative or positive brush I think that people are
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just complicated and especially people who change the future and so I'm I'm a little bit more more sympathetic to him
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than you might be I mean I understand complicated means having 12 kids and living with none of them and and and
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demonizing trans get he's complex yeah but but like what I'm what I'm saying is like I'm not just a shill for Elon right
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I haven't invested in his startups I'm not like I'm I'm not trying to say I'm not trying to be tribal about it right
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you have a very calat attitude Mark Mark benov has the same one here's the only thing I would say about the cutting
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prices he was allowed to blow up Rockets NASA isn't like so he can be more disagreeable and risk-taking then you
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know what I mean it's very easy to figure out the way to do it if you're allowed to blow things up and and so I
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think and by the way I think that's good I think we need more of that right like
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so you know but NASA can't so attacking NASA NASA actually can't blow things up but but I'm not attacking him I'm just
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saying a pattern breaker changes the you're acknowledging the truth he can put into space for less money than
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anyone else it's in I'm saying that all things being equal I like it and so so the the thing that Elon brings that I
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think we need in you know an ingredient in this recipe is he builds things right
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like when he says he's going to blast Rockets into outer space he does and when he says he's going to make an
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electric car work that's interesting and awesome he does and you know I got a lot
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of time for people like that in this Society um let me ask you I'm going to switch you from this just for a minute
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but there's so many AI startups now we just talked about what was going on at open Ai and we thought losing money all
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the mishas it doesn't matter this is a world changing company right it's been doing astonishing things ultimately it
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probably will settle itself out but what would you what would get you to invest in one and what are you interested in
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especially considering all the competition now there is a lot of open AI Google Microsoft anthropic it goes on
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and on and on yeah I haven't done a whole lot of AI investing no um it's uh so we've we've
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had a couple of ones that have been good so um applied intuition uh is a company
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that helps with autonomous vehicles and um EVS uh but it's enterprise software uh you know really large contracts uh
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and then I invested in uh trip Adler's new company the guy from script uh it's called created by created by humans and
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it's trying to trying to let creators create licensing deals with the llm companies um open AI is really not my
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kind of investment um I I mean I wish them very well along with uh anthropic and all these other guys but my my
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business is hard but not complicated um I'm wrong 85% of the time and when I'm airnb Airbnb correct yeah when and when
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I'm right I have to be spectacularly right and so I'm really good if 5% of my investments I make 100x on the first
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check and another 10% or so I make more than 20x on the first check I don't see a path to doing that investing in open
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AI right now or X not a venture investment you're a venture investor it's no longer exactly exactly and and
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by the way a lot of people who call themselves Venture investors in today's world are are unrecognizable to me I
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just mentioned Airbnb you had talked about it that you you you passed on this stup talk so yeah um talk about what why
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you did that and what do you look for when you make those misses like how do you as an investor when you everyone's
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going to I can think of a dozen different people who Miss whether it's Instagram or or whatever yeah so first
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of all it's helpful to just consider the backdrop that these startups are wild in
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the early days like people talk about startups the wrong way it's like trying to spot a beaked VCH in the galopagos
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islands with a super long beak that has an Adaptive advantage that allows it to survive in a new way but like you've
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never seen one before but it's wild right it's like a mutation so so with with Airbnb the prior week we'd been
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pitched by a company called Mojo mix that makes let you pick cereal online and it'll assemble it and ship you in a
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box and my partner an said this is dumb why are we talking to these people this isn't even what we invest in and I was
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like okay that's fair I tend to be The Optimist and tends to be the skeptic you know when we look at this stuff so then
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um week later we go in a conference room it's airbed and breakfast this is a year
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before they'd applied to YC and and and Ann looks at me all these cereal boxes like what the hell another cereal
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company and I kind of look back at her like no it's airbed and breakfast I don't know what what's this cereal about
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so I asked him and he says we're funding the company by selling cereal boxes and
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so I was like okay so Obama O's and Captain McCain Crunch and then and then I say okay well what does air bed and
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breakfast do and he says well uh our advisor says that you like demos and not slides I said that's right so he fires
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up the the product and he can't get it to work and so I'm like okay that's cool we we'll do let's just go to the slides
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he's like well I didn't bring any so we're like 20 minutes into this meeting full of cereal boxes in a conference
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room and I still have no idea what air bed breakfast does we're just kind of kind of looking at each other in in this
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room and and so but you know he he I knew even at the time that he had this certain xfactor but I I let myself get
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preoccupied I thought somebody's going to get murdered in one of these things cuz you you know at the time it was
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barely more than a WordPress site you know you you invite a guest to your house or apartment and then you serve
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them poptarts the next morning they sleep on an air mattress and I was just like this is just crazy you know and um
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fortunately because an and I had stupidly passed on this company when Lyft says hey we're going to do this
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ride sharing thing and or you know people are like our strangers going to want to get in a stranger's car an and I
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are like hey we'll take a walk on that wild side you know I can see it happening so um but with Airbnb it was
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just it just it was just such a discombobulated meeting and the idea was so crazy and you had couchsurfing.com
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which was free and it was going nowhere and I just I just wasn't awake enough I just my mind was not open and awake
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enough to the possibility of what it could be right um and you got as a venture you have to do that you have to
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sort of yeah and and and I and I I told myself I'm G to learn as much as I can from that mistake and never repeat that
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mistake because like in in corporate capitalism you know Buffett would say rule number one don't lose money rule
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number two don't forget rule number one in my business rule number one is don't pass on Airbnb because I would have made
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6,000 times my money if I'd say it it I could have made no good investment the rest of my entire career would still
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been really good so um so I spent a lot of time really understanding what I got wrong and and you know another good
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lesson in that is quite often the best seed opportunities don't present well and it it's it's incumbent on you to be
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awake to what it could be rather than oh the entrepreneur didn't present well I'm
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I'm out you know often happens which often Happ maybe more often than not Mike thank you so much what a thoughtful
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um uh discussion thank you and again the book is pattern Breakers why some startups change the future