Sharing the triumphs, trials, and invaluable lessons of being a founder with Shane Mac

Transcript

[Music] we are incredibly fortunate um to have Shane Mack co-founder of xmt joining us today I very intentionally used the word fortunate because it has this really sincere sense of both luck and gratitude um for those of you who don't know Shane has like this incredible wealth of entrepreneurial experience uh to draw from but Shane is also like one of the most introspective people that you will ever meet um and so we're I I and we are very lucky and grateful and therefore fortunate to have you with us today um

you know those two things that I just mentioned wealth of entrepreneurial experience um deeply introspective like it comes to fruition in this coalescing of like remarkably personal stories about life and relationship building and business and so everyone please join me in welcoming Shane Mack to CSX London thank you all I'm really glad to be here um I want to copy out what I'm about to say is not just lip service because we're on the stage um sure but uh you have this profound ability to really not only recognize but appreciate these moments where your perspective like totally changes and I realize walking around London and yesterday

together you have like this little slight tell when those things happen because you will slow down look me right in the eyes and be like and that is literally everything and so I wanted to um I wanted to ask you about the moment of everything that led to you being here as the founder of a decentralized messaging protocol and maybe starting with your experience in Twitter what a small question uh and I don't I um I'm really Greatful to be here and I'll try to start this off in the beginning just in showing my arc and I think when you say Twitter you know I was in a little town in the middle of Illinois there were 800 people in my town and I went to Western Illinois

which is a state school That No One Ever Knows or cares about and I was messing around on the internet in 2005 and Facebook came to our college and at the time I was actually in a band I was playing music and I was emailing a lot of people to book shows and I was trying to get a photo to show up on top of email and and at this era of the internet it was really creepy to tie together your online Persona from LinkedIn to Facebook to Google searches you kind of felt like you had different silos you didn't think offline and online could be discovered and it was really weird and so aggregating an email address to a Facebook photo felt really creepy at the time and then Twitter happened and for me I I saw Twitter and I thought I can text anyone in the world

and I felt like I grew up in in a little tiny town I was always on the internet messing around and in chat rooms and it was this group of developers that were so passionate about an open protocol to build communication and it was all based on SMS Twitter didn't start on the web it started as an SMS protocol and for me just to be able to throw ideas out and I started throwing ideas out of hey what if I put a Twitter photo on top of my Gmail uh address and next to my Facebook photo and I was teaching myself how to code and I was working on that I get this random tweet one day from Jin pits I'll never forget it and I was like is this online dating like I I didn't really know like what was going on I'd never met anyone off the internet and

she's like hey my boss really loves what you're building and she's like would you want to meet him so the long story short I meet this guy ta mccan he ends up being a legend in Seattle he was the like founder of building uh exchange at Microsoft he was the head of Outlook and he was building a new startup called mindbox which was about news search based on the Inbox and he goes I think social data on top of email will make people smarter in the future and this is actually a big idea and uh you know I want to understand what you're doing so we talked a lot I flew out to Seattle I met him and you know we spent time for three months talking about social data email Etc and I was just really passionate about the social internet I didn't know what a startup was I didn't

know Venture Capital was I didn't know what any of the stuff was um I was a QuickBooks manager of the local theater in my hometown and just you know basically faking doing QuickBooks all day uh and at the time he was like I'll pay you more than you make now I'll give you some percentage of this company and we should go do a startup so it became just.com we were one of the first API Partners ever with Twitter we were polling social data created a social address book became the fastest growing social address book I think ever went to zero to 100 million people in under two years and in the ' 0809 era of social it was like what can we do with all this social data and as a developer on top of social data it was so INSP iring and at the moment of that

part of our career it was what can we do with all this data Zuckerberg was like do whatever you want with Facebook data and Jack was like we're going to be an open platform and we're going to help people and you can do whatever you want you can use all this and show us what you can do and we'll be great partners and we're going to commit to you and developers first and developers developers developers and all this stuff and we grew it and we got acquired for $50 million in 20110 by blackberry and I got to go work on BBM and everything started changing messaging started locking down messaging started growing social started growing and my next company was called assist which was um about business messaging and chatbots and we were the first API partner to ever launch on Facebook Messenger 2014 Zuckerberg demoed 1-800

Flowers you'd never have to talk to a human and we were the powering chatot platform of that but over that whole era I became obsessed with messaging and I was always a Dev platform on top of the protocol and I never realized it because I just stumbled into it but I realized that my entire relationship for 15 years of Technology was built on fighting these platforms who told us one thing and [ __ ] us over once they changed their mind on it and my whole career was getting rugged the Twitter API changed we $700,000 a month bill came the Facebook API changed we lost all of our Partnerships the V2 of the Twitter GM changed we couldn't do broadcast anymore the entire Fortune 500 who Ed our platform no longer could reach everyone on Twitter and my whole career was being their best partner and

getting screwed over by them it was this LoveHate relationship because they also built our business and we had like very lucky outcomes and for me when Matt came to me my co-founder and we were just exploring identity on xmt and what happened was Robert Lesnar came to us from compound and he's like I have 11 billion in a smart contract I know every single person's address I can't message 95% of them because I have no other way to reach them than their wallet address why can't I send them a secure message and that was the light bulb moment 2019 D5 summer 2020 and then creators started happening and nfts and then Mike shenoda from Lincoln Park was like why can't I have a blockchain that is all my audience and I can own my audience and then why can't I just message them and I

have to worry about Ever Getting rugged by these platforms and for me it led to here I met Matt on Twitter back in the day we lived next to each other in San Francisco for 10 years both of us built the first kind of social companies his was called social thing ours was called gist pulling social data out but both of us had spent our whole careers basically getting rugged by web2 social and for me to build a platform where thousands of developers can build on a permissionless protocol can build on an open messaging Network that can last forever because a company doesn't own it is the thing that drives me every single day because actually you can build more meaningful companies you can think longer term you can understand the rules because they're in code and they're actually out there public and to not have to trust me is to

be able to trust us and for me that that drives me so deeply because I spent so long not being able to ever trust but wanting to trust and it wasn't their fault the only business model of social networks was attention and the only business model was arbitraging the app and just cutting out the developers and it just played out over and over and over and over and over again and I think to this day if you can't see it in the protocol and someone's telling you to trust us you shouldn't the uh I told you you would want to wake up for this right like uh if you're not ready to run through a brick wall like I don't know what's wrong with you um but not my hearts racing I yeah I'm like I'm ready to go we'll get back to XMP and on many

measures or metrics um xmt is a success in trending the right direction and but I think for and you have such a you know again this like wealth of Entre entrepreneurial background to pull from and I think for this group in particular um it would be really beneficial to start with something that didn't work and that's zly um and for anyone who doesn't know Shane is a prolific writer and we can we're going to get into that as well but you have a blog post called the best way to kill your startup and what I learned doing just that um so I want to kind of talk about zar and hope that you can um you know walk a little bit through you know the blog post and and unpack some of what you learned killing zly yeah in between assist and uh gist is the one I always like oh I

didn't even forgot about that one uh there was a three-year period where I was the head of product and founding team of the thing called zarle and you know it's funny people say to me xmt is successful XMP is not successful yet we have a lot going for us we've had over 100 million DM in the protocol we've had a ton of spam hit us though we have major Partners we have 1.9 million identities activated on the network across DNS and foraster and lens and all of the things made it we have not had a killer use case that millions of people are going to use in love we have not found the group experience that's really an economy running in groups we're not there yet um we just have a lot of early momentum we've raised $50 million which plays into I think a lot of the story I

learned in Zari Zari was a local Marketplace and at the time this is 20 2010 so this is Uber Postmates Airbnb all that era we're all in the same little three block radius of San Francisco I live down there Logan from lift's my friend it was called Zim ride pivoted to lift boom lift and all of the sudden we were the local Marketplace that wasn't going to be verticalized it was you could ask for anything you could ask for a ride you could ask for a coffee delivered you could ask for a dog walker you could ask for a baker and it was a reverse Craigslist we raised 35 million in under probably 18 months we raised 25 of it in under like 6 months it launched at a random hack of on at uh startup La it was like a crazy thing and then a weekend we actually built a

product we had a killer CTO I and he's still my best friend he lives in Nashville with me actually and we built this product and you could just say hey I'd pay $500 to rent someone's Lamborghini out front it would ping everyone in the room and everyone in the room be like all right that's my Lamborghini boom made 500 bucks and the demos were so magical that it was a drug and it led us to the wrong path and what happened was we went horizontal not vertical and the biggest thing that happened was our egos our lack of self-awareness and our inability to actually think smaller to go bigger and at the time I didn't know I'd never really done a Marketplace I didn't really have the Silicon Valley experience I didn't understand consumer technology at that level and I was

wondering I thought about this the other day like why did the same investors who won in the first wave win again in the second wave it's because they knew this secret and we would sit in the office and I remember this guy Alex sharp he said one day ha we're not going to be a dog walking app we can do dog walking and a lot more and I'll never forget it and he tweeted you could go find this tweet today his name is AJ sharp search this Postmates he tweeted at the Postmates founder Bastion and he said ha you're just going to deliver coffees yeah good luck with that vertical and I don't know how much Postmates sold more sold for but I will tell you it was more than us I remember that because internally our arrogance was sitting there being like we're not

just a vertical app we're bigger we're better and you know what VC's bought that [ __ ] we were down there in Silicon Valley and I watched this guy B he's fantastic friend of mind this guy I mean if he was if he was a t evangelist preacher we would be bigger than Joel um and he was pitching and he believed in it and he was like we're creating a new economy this is a new economy it's a local economy it's a reverse Craigslist it's this this this this this but the product only kind of worked it worked 50% of the time we were arbitraging it a lot of it manually behind the scenes we had a whole team on Craigslist arbitraging Craigslist but that's what Airbnb was doing so that kind of works but we were across so many verticals that everyone was arguing about what the

right vertical should be I remember the day when me Whitman walked in the room the CEO of eBay and she's like this reminds me of eBay every time we added another category to eBay we made more money we shouldn't be a vertical company we need to make sure we can you know go to more verticals and she was awesome but also her experience was built on web one right and you got be careful who you listen to and or take their advice and then think about the customer what is actually changing and what was changing is that we couldn't have picked a small enough vertical to build a great experience around and once we nailed that we maybe could have got lucky enough to build something else but it turns out Wag the Dog walking app is A5 billion doll

company we couldn't have pick a small enough vertical the reason is is because the community you build the suppliers you build the the evangelism you build the way it spreads Word of Mouth the product experience I mean wag is amazing you know why because when your dog goes on a walk you can see where it shits I'm not kidding it like and to build that Nuance of product that map where you can see oh took a pee took a poop how many long wow and then the community around it if the Market's big enough dogs people like underestimated animals the Airbnb for dogs also a billion dollar company they all merg Rover but the key Insight was our ego to and our pride to want to think more horizontal and bigger was the thing that actually that's not what any of the

investors want they want you to actually win with real stats and real growth and make it work and it's not actually from going broad it's from actually going less and then if that doesn't work switch the switch the vertical or maybe you need a bigger vertical but adapt from there but the bloat we got like the the experience you got from Uber and the map and the car and the driver and the rating and the pass rides and the the badges you get are so related to rides that it made rides magical but us trying to do rides and Postmates and wag and cakes made our experience mediocre or bad and to me we didn't have the self-awareness to sit in there and say is this not working why is this not working actually only 43% of the time do

we actually get it fulfilled and it's because we manually have 100 people in the Philippines reaching out on Craigslist doing this thing and it's not real time and it kind of works and it kind of is just like but we could always justify it and we did so much justifying and I think the lesson in it is it came from our insecurity and our ability not to look at the team and say I don't actually know if this is working yet but we believe in it we can work on this if we think smaller if we get more focused if we do less and actually feel if it's working is it working is it not and if it's not had I said it's not working but that's fine we can make this work we would have won but I didn't and three years in what happened was every

employee we had 45 employees sitting in Min Plaza Downtown San Francisco all the money in the world fancy ass office Jack dorsy lives next door were so successful we were like wow we live above mint Plaza we can get amazing coffee whatever we want Lunes you know the most successful thing we ever built was Blue Bottle cam looking down out of our office at the [ __ ] coffee shop literally and like a whole all if we would have if that would have been an investment like special purpose vehicle from that camera every single person in that four block radius Ed Blue Bottle Cam and loves Zar for the camera yeah no one [ __ ] used Zar people just used it to know if there's a line of blue bottle we would invested in square and Lyft and Uber and Twitter and we would have been

I would not be here um and what's fascinating about it though is had I just been okay saying I I don't know and I actually I do know this I don't think it's working yet the team is more motivated and holding that secret and thinking you can't share when it's not working or asking those questions together is the thing that ultimately leads to the culture you don't want when you think you're protecting the people but the truth is you don't want the people early stage that you have to protect and get getting that wrong is really tricky uh I think that that lesson is something I deeply think about even xtp when you say we've been we're successful I'm like we're not like we have a lot of good things going for us it works I use it every day we're not a

billion dollar company like WhatsApp we're not a a user company like we're not there yet yeah but we have a lot of great things happening subscribes working Jamie uses it lots of developers use it coin sure well I think but not not yet what's interesting about the the way that this conversation has kind of shaped around zarli and you again I've said this in the beginning like deeply introspective um and so you have another blog post that's called how I'm lying to myself and so for again like I think this is so valuable for the audience to hear like that blog post really dives into the mechanics of like how do you fix those things like how do you become more honest how do you talk about the hard things um so in the blog post um how am I lying to myself there's like

different examples and I'll just give you one as kind of like a prompt here because I think it's really applicable to uh everyone out out in the audience building and the LIE is if we push harder we will get there there's another one our culture is struggling because of X there's another one if we just add more we'll find what works which I think is potentially you know reminiscent of Zar um how are you keeping yourself grounded every day with this concept of you know I'm not going to lie to myself about these anymore I'm going to be upfront with these like how does that come to fruition for you whether it's in your personal life whether it's at xtp today how are you continuing to like Institute that yeah I think the the tricky thing

about lying is that we all do it but we actually believe that we don't and we think that we're um aware of it when we do and actually the the worst lies are the ones you can't hear and so being able to create space that allows you to listen and there's tactics on figuring it out so look at your last investor update and look at what you didn't say and then ask yourself what did I not say what am I scared to say what do I think if I actually told them that it wouldn't probably it might be uh really scary to say or you're really worried that they might actually uh not invest or whatever right and I think figuring out what those are for you and how to

understand that leads to something that I say which is like if you want to go into a VC pitch meeting and you don't want to get shot then just commit suicide and I don't mean actually commit suicide but but if you start the meeting with the thing that you're so scared to talk about take um user growth if you don't have user growth start the meeting in that area and say you then own the story listen we don't we don't have we're not focused on growth we're focused on retention if we have a leaky bucket then it doesn't even matter if we have growth and all we're doing is product and just trying to iterate on product and this is a thing I would love your feedback on and you can lead the conversation there and build honesty around them and you you have that

authenticity from the conversation and then you end the meeting on a high versus ignore that and at the end of the meeting you get shot and then the meeting ends on the you're like you know how's growth and if you can look at and be more introspective and figure out like how we lie to ourselves and lies may be an extreme word but you know the more work you do the more you realize that like that's how we deceive ourselves and you learn to ask questions of like how is it not working how how does the team perceive me right and at when I was at Zar like I learned that they thought we were so confident and full of [ __ ] and really what I deeply thought was I was protecting them and I didn't want to share that like we were running out of money and I didn't want

to share that we were burning so much and I just kept talking about the use cases that were working while being deeply scared that we weren't and I just leaned into the thing on the other side while then being confident on the mission where we're going how to focus what what can we control what are our weekly rituals and you can control the ways in which you ship the ways in which you analyze things and the way that which you create a space to ask honest questions I don't know I think there's a lot of different things in that but just the language and the questions by which you can ask yourself or create space to listen uh it's hard to do it actually it's so easy to just go scroll another tweet and scroll another feed and talk to your talk talk talk I've never

learned anything by talking yeah well it's interesting so like one of the things that came what I just heard you kind of saying is um this concept of like through honesty you control not not only the narrative but the environment in which you're like operating and so I want to talk about another blog post so like there's a theme here as you can tell Shane is a prolific writer I highly encourage you to follow his his blog if you aren't already uh you tell this story about um about how language drastically changed one of like the most important Partnerships you've had and was with apple um the post is called the one question that almost killed our biggest deal with or our biggest partnership with with apple um can you talk a little little bit about the

audience for this concept of like change the question change the environment change the outcome totally so this one for me is everything because all of you are going to go build teams and you're all going to go build companies and you're going to go build culture and culture to me is the language and the rituals by which you do things that creates the space for others to know what to do that's it and I had used the wrong language my entire life until I met a guy named David marqu the Alex talked about him earlier the Navy Captain who was the head of the Navy he's actually been my coach for the last 10 years one of my best friends these days and I was lucky enough to have him join me for the largest uh launch we'd ever had at my last company which was a

messaging company that doing chat bots on messaging and it was with apple and all the executives from Apple flew out we were at the Philly Stadium and imagine the Philly Stadium every single seat in the stadium has a QR code this is 2018 so pre-co so everyone thought QR codes were Silly um but every seat had a QR code iMessage was opening up to brands for the first time ever and you could scan the QR code TP two Bud Lights and a Yingling and Order beer to your seat with Apple pay and fully reorder automatically with no human fully automated all in ey message and so it was actually it seems easy to do it took me about a year of planning to do this and there was another partner there I won't say their name be because they were not fun to work with um but they

didn't really do anything but they were like had to be part of the conversation because of the way that apple had set us all up and we were in the room and their technology started failing and I had told the team six months earlier imagine the live chat agent software fails because they want us to fa fa and build the same thing so that if at that moment that day when they say their [ __ ] doesn't work and this whole thing's at risk that we have an agent platform and this guy Carlo is's my favorite engineer about 11:00 a.m. I get this call hey Shane uh the live agent software isn't working the the connection doesn't work the bot doesn't actually work and it's blocking the whole this is six hours before we go live the whole Philly Stadium is lined with QR codes and the

Apple team has no idea and they're all out there Tim Cooks emailing like we love this use case you know and we're like what's about to happen and so I go Carlo did you build six months ago and I said imagine we get screwed here and build the backup plan did you build it and he goes he smokes a cigarette that got a true Italian he's Italian of course abasa and he turns it on and it it it actually looks better than theirs it has a full POS system and he's just smoking a cigarette and I was like hey Amanda we got to go train all of these all of these beer delivery people on the person here that's sending the orders hey b75 and they're just sending it from the back room beer out we had to train them how to use this software because they

were trained on this other software and this whole story's happening at the moment David flew in he's like I'm gonna fly in for this launch I'm G to record it I'm gonna put it in my book and I'm going to show how like great leadership leads to Great outcomes everything's no pressure everything's screwed nothing's working the whole thing's collapsing me and David haven't even talked he's sitting back there taking notes like this looks like a chaotic mess you know and I was like hey you want to go to lunch and I was like Amanda are you good she's like I'm good I'm good I'm like are you sure do you need me here right now like we're just going to train these agents it's an our new software whatever she's like yeah I got it cool so I go to lunch David and I sit down and I sit

down at lunch and David and I get a water and we're looking at the menu and Amanda calls me and I'm like oh man's call me I said hey what's up she's like Shane uh the live the the other live agent team is all like really mad and they're kind of like really pissed at us they think like we're trying to screw them over by replacing it with our software but like our stuff really works and they want to try to plug theirs back in and I was like tell them absolutely not and like just train on our agents do you know how to train on our agents you're like yeah yeah I know how to train on our agents like do can we do that yeah yeah do you need me there no um like I I'm telling you right now like if you need me there I will come back

right now I'm only 10 minutes from the stadium I'm like are you sure she's like yeah yeah we're good I said are you good and she's like yes and I hung up and David looks at me and he goes what' you do wrong this the silent Observer and I was like I mean I felt really empathetic I felt like she knows I'm really there with her I felt felt like I was really telling her like you know I'm the CEO and I'm listening and I can be there in a second he goes call her back and when you call her back say on a scale of one to five how much do you wish I was there she's like hey I'm like hey I just have a question real on a scale of one to five how much do you wish I was there five and I learned in that moment

that if you don't change the question and you don't change the environment you will get a different outcome and as you become leaders and as you become the people running your meetings and as you become the people running your companies our blind spots and our egos and our inability to ask binary questions and realize that the highest performers in the company the people at the highest performing level will always default to the less friction to the boss the less friction to the boss and so your best person Amanda she was the best person in the world she was so good at her job on a level that I would be like I trust man with anything and she couldn't tell me I need help until I created the environment for her to say it and you need to think about that and a trick to do this is to

never ask a binary question use the word how you can't ask a binary question if you start the sentence with how how could this go wrong how much would you like me to be there but if you say do you want me to be there she will say no and if you think about this in the language within everything you do you will get different outcomes to your meetings to your people to to your leadership to your feedback to your company and to the whole thing and had that collapsed and not went off it could have killed the whole company and that's the reason we got acquired everyone wanted to buy us after that moment it made the Apple earnings call Tim Cooks on the earnings call like we just launched it the Phillies business messaging is amazing Apple pay is awesome and the assist team just blah

blah blah and and that was a moment of the company and we were three hours away from that probably kind of blowing up and I'll never forget that moment and David marquay asked me to write for his book and actually he got the best story ever which is that story right and so the story in the book is about using the word how and not asking binary questions and that if you change the question and you change the environment you will change the outcome and if you're not aware of it and you're not sitting there thinking about it or asking it in different ways I think about it in every single meeting I'm in and it leads to relationships and Trust at an executive level that I've never had and that's what you need to do within your

companies and that's what we all have to do if you want to have a self-aware honest and a company that is able to see the problems for what they are and not [ __ ] around and actually flex and act like we don't need to help each other I want to definitely take questions so Shane is uh has very kindly flown here from Nashville he is here with us so definitely use your time with him uh the one of the stories you I talked about you uh I think transparency was a a theme and I just want to know how you feel about transpar Arcy in the way you conduct yourself uh in what way personally professionally investors like what context professionally I think uh H do you find do are you completely transparent when you're talking with

people or do you hold some amount back for negotiation purposes how do you think about that even it all depends on who you're talking to my goal is to be open and transparent with everyone in the right moment and let me break them down because I think they're very different you have internal culture right you have Partnerships you have investors and if we just look at like that or Partners right uh for like the public stuff we're very open we're an open protocol and we try to be as transparent as possible and write publicly and vulnerably I think vulnerability leads to kind of feeling transparent there's always things we're not saying right it's how you say it that actually leads to feeling like you're transparent um and I think just the ritual by which you communicate is

important so I always think of setting the expectation of when I'll communicate so that people feel that I'm being transparent and I learned this the hard way in the past because too transparent can be chaotic when I was I'll be transparent I'll share everything I scared the [ __ ] out of my team because I was cha chaos right versus actually what we do now this is our 147th week at XMP the day I started the company I told Matt here's what we're going to do every Tuesday at 10:30 a.m. we're going to write a dispatch it's going to be an intro for me or you and we're going to do it every other week so we hold each other accountable we're never going to miss a week it's going to say this week last week in key decisions and everyone can look forward to our communication

weekly and then we can be as open as we want in that email and the Cadence of which that is we've never missed a week we're 147 weeks in and it drives a weekly ritual of execution at our company that we work in week everything week Sprints week thinking week planning like that's how we think um and that leads to them feeling like we're very open like we're very open in that I'm very vulnerable in all hands if I've had to fire people we had to group layoffs I've gotten team wrong I had to change the strategy but those strategy moments I think I'm fully open at exec with everything and I let them know that everything I say is not a decision it should lead to the next meeting where we have the conversation but we should keep exec conversations tight until we know how to

communicate it in a clear manner to the company and compounding Clarity is the thing I look for now because I used to create compounding chaos and Rapid Fire communication of openness is actually chaotic can't comprehend it it's hard to think even if it's well- intended and so a ritual for your partners that is set a ritual for your team that is set and then be chaotic with your most trusted Partners on the exec level that can help you be more clear to always think about how to then go out with it and then publicly like mystery makes history so you know hide some [ __ ] and drop some [ __ ] so my thing is I'm like I come from a very technical background as well and you know being a first-time founder I feel

like there are other people like me who don't understand or know the language with which you are communicating to us right now where you are using excellent terminology uh almost like I was trying to be jarg no no no not jargon effective terms of business that I have never had to encounter before listen to your heart well that's a good one I like that one I'm just kidding like like what what would be an example of that um for instance when talking to investors and they start asking questions about your valuation structure and funding and things that you haven't yourself been educated and you're not considered about you need to be able to you know transparently but also not give transparently communicate with them but not give away the game do you know what I mean it's I know this is a very open

question but it is very much what is the most effective way for us to learn like that those terms those business things uh hopefully reading a lot of books but you know I'll take whatever you can give me do you mean around like the the actual fundamentals of of venture starting a company raising money absolutely yeah um well there's a lot of VCS in here I don't I know right they're really good at talking like this let me answer it in just a general term and just you can tell me if it's [ __ ] or not okay I think that being a firsttime Founder is awesome and there's a lot of hijacks the second time that you're like God I wasted so much time having to learn that you're just going to have to learn that there's books there's mentors like that's all the general advice I would say that

there's a thing you can do that is the greatest leverage in the world that actually allows you to learn at the same time and that is a philosophy I call doubt is your greatest leverage so if I'm in a VC meeting and we're arguing they're they're choosing yes or no not because of your valuation they're choosing yes or no and VCS are binary once they choose yes then we're just debating a bunch of [ __ ] right so your belief in yourself your belief in your mission and then your ability to not say [ __ ] you don't know about right like oh I was thinking you know we're doing about three on a 12 and you just make [ __ ] up don't do that unless you've already thought about it

you've planned it out that's two years in the bank and actually you're there and I wanted to dute 10% whatever but you could also say you know I I'm trying to think about as a first-time founder like how do I only dilute 10% at this level like look at our product traction look how far it's going like and go get some other BC conversations happening and ask them to help you think about it that's what they do for a living and actually the doubt is authentic and you're asking them for input without saying anything and at least in that moment because it is all Nuance at this stage right some I walk in I'm like listen we're raising 10 on a 50 and you're like all right you know like great but if you don't really know it and you haven't done that work and

it's early learn the signals by using doubt as a way to actually get leverage and doubt is the greatest way to let someone else help you and it's not a bad thing and I think if it's if it's authen if it's authentically done because you actually don't know not like manipulating it I think it can be really valuable that's great right yeah I mean I think it also lends to your comments about and your blog post about how am I lying to myself right like totally um that open and honest conversation with yourself about where your knowledge is and asking these types of questions in it open for him and now you know having the subsequent conversations to go fill that knowledge Gap because the great VCS like an Andrew this level of VC wants to help and they know what they're doing

they see deals all day every day there's no if you ever think you're gonna win a negotiation with the VC you're high like all they do is this and so actually ask them like you know meeting with J like ask them what is the best way to structure this what are the three different scenarios can I raise more than less like I don't I'm not really sure here um if you kind of have those relationships I wouldn't walk into a firsttime VC and it's the big pitch meeting and kind of maybe have that strategy but maybe you shouldn't be pitching at that meeting if you're kind of in that much doubt so that's kind of My Philosophy there I'm Lisa I'm from newor York I'm one of the founders of Rue yeah it's the recipes that get forked so you can remake and remix recipes as many times as possible so

that everyone in the world can get value from the recipes from one Central recipe nailed it I'm just kidding he listened to your elevator pitch it was great um a lot of the founders that go up on that stage uh at some point mention a mentor in their lives one maybe many you've done the same uh can you tell us a little bit about either the time in your life or the context that was happening around what that relationship looked like how it started was it something that you went out and sought was it someone that dropped into your lap what' you say that I didn't hear that of what moment uh when a mentor like a very important Mentor um when you started a relationship with a mentor who proved to be very important with you you know I would say Robert Stevens so Robert was

my co-founder of my last company uh but I'll share like what I learned there's two lessons I learned he was the founder of Geek Squad and you know and he built a multi-billion dollar company that I haven't done um and he was a SE o Best Buy for 10 years he became a mentor and I met him on Twitter cuz he was the CTO Best Buy and he literally was on Twitter all day and I was like how's this CTO Best Buy like just on Twitter um and I just messag him messaging to me has changed my life like the reason I I love messaging is actually everything in my life is happened from digital messaging since I was 13 years old on eBay and Robert I dm'd he was like I'm moving to San Francisco and I was already there and I said if I can help you let me know

and I started having dinner with him and his wife and he's like this brilliant thinker he's kind of like roll he's he thinks completely differently than everybody else he's like the wizard of us I would go to these big meetings and I would walk in and robbert never I mean probably just the joke of like you be CEO you like I'll just sit back here in the corner um and I'd go to these meetings and they'd be like I'd have all these Robert stories and Robert isms and they'd be like Can We Ever Meet the wizard I'm like probably not you know and like him being the wizard of O was actually the secret of it all but he's now my best friend in the world and I think two things happen you have a mentor who came in and he told me at the

time he said your ego is so big you need to stop saying I would say at the time messaging is the future of search and that ability to not have my pride run my life and run around chest pump chest in Silicon Valley VC speak changed everything because I would have failed assist had I kept doing that and I was saying messaging the future search where go he goes just by saying that you're actually telling the team we're not going to be able to deliver next week we can have a big external Vision he's not saying don't do that he's like but on a dayto let's talk about actually we're just going to make a chat bot via 23232 book a haircut at Great Clips and let's do it by next week and at the time the thing that you should

bet on this is like Chris Dixon everything starts out looking like a toy what that actually manifests as is you have to be confident building something that people think's a joke that's the hard part the hard part's not oh everything starts looking like a toy it's that when you're in it you're like I don't just want to be a meme platform I don't just want to be a dog walking app I and and Robert said to me we should kill all this live chat support we should kill this messaging app we should just build chat Bots and let's just be an automation platform and I was like chatbots that's a [ __ ] joke right now it's funny here we are 11 years later like yeah and somebody asked me today how' it feel to know that you guys built the first chat bot on messaging I said

it feels like I'm not a billionaire um and and he said that though and I remember the time he said that and a true mentor and I and what he gave me what a real Mentor gives you is the ability to not seek validation elsewhere and to believe in yourself on that thing and I everyone thought it was a joke our investors thought it was a joke you can go read the tech crunch article assist has no app and launches with 13 services on 23232 and VCS were like man you had the best designed app I'd ever seen you killed the app what are you doing like what and no one got it and that post Robert gave me that confidence literally the CEO of 1800 Flowers sell it I get a call he goes hey this is Chris mccan I'm the CEO of 100

flowers I'm like oh Chris what's up uh he's like I saw you integrated Flores one API Freer chatbot why did you not use 100 flowers I'm like well I don't know if you have an API he goes yeah we don't like well why are you calling he goes because I want you to build that chat bot for us and I was like at the time we weren't an Enterprise messaging platform yet we were trying to be consumer and that actually that moment Robert gave me that confidence to step off the ledge and put out something that's kind of a joke not a joke we integrated it he literally got his haircut at Great Clips still to the day he only does it because of the queuing system of efficiency and he'll get a shitty haircut because he can book it fast that's [ __ ] crazy like that's

how robotic he is and to the first thing he integrated was you could text cut it would text back here's the nearest three Great Clips 12 minutes 19 minutes 24 minutes You' say one and you would show up and your name was on the screen and it say Robert Stevens and he was like this is it this is the future this is chat Bots we don't even need to use the internet the [ __ ] website suck long story short the the CEO is like we'll pay you 100 Grand to build this chat bot because I want to build a messaging service where people don't have to call when 100 flowers at the same time Zuckerberg is planning to launch Facebook Messenger platform David Marcus calls hey we're thinking about flowers as a use case for messaging we saw this like thing you're doing do you have any

other partners and he thought we were using Flor one and I was like well actually the SE 100 FL he goes 100 flowers I think we could say on stage something cool about that and then we started working together nine months later Zuckerberg gets up on stage and says messenger is now open for business and he says and Zuckerberg calls 24 hours before the demo and says do you think the CEO of 100 flowers will care if I say because of Facebook Messenger you never have to call a phone number again and I was like his business is named a phone number um I don't know and called Chris mccan and Chris goes Shane my whole career is built on being first on the platform shift we were the first person to sell on a-800 number I was the first person to sell on comp served in

1993 and we're going to be the first person to sell on messenger and I don't care what he says and he came and he sat in the front row and we sat there together with Cheryl Samberg and Zuckerberg demoed it and literally it and then we became the largest Enterprise you know bot platform with uh Facebook for the next seven years I was CEO and Robert became one of my best friends and my true partner and I think the best mentors in life are the ones that become Partners it's hard to work with I'll be honest like working as a co-founder with Robert at the first few years when I was seeking validation from Robert is hard you're like trying to always ask him and he's like hey you're the CEO like you know figured out there was times when it was hard to deal with

that and then you know I think self-awareness honesty being vulnerable leads to being able to figure out how we're very different uh and now you know we're true I talk to them every day every time I get in the car I call Robert and we get to talk every day so my question is about writing um talk to me about your writing process and you know distilling down these big ideas and and putting them into something that you know people can reference and carry forward and you know revisit over time in what aspect like are you asking about the process the insecurity I go through before I publish the the the framework like I'm curious like what what would be most helpful to you yeah I I'm curious how like when you have an idea like you have the idea for something that's going

to turn into an essay right or maybe you don't right and it's really kind of an open question about you know your writing process and how you kind of approach getting like this thing on paper um yeah and and articulating what you might think want to it's a good question and I think I'm probably more of an artist and a creative in this sense and the business founder CEO of me has learned over time how to put a gate up to know how to contain this to be creative in an engine and then know when to publish and in the past I don't think I had that as much I would very much like would just completely write and hit publish uh which I talked like I think compounding chaos was the the thing I

used versus compounding Clarity um I'm way more of I have infinite thoughts my brain is just like a pinball machine I spend a lot of time trying to you know calm it down trying to be more present trying to listen to things I can't hear that's come over time and when I have these thoughts I always I have a note on my phone has thousands of titles and just Apple notes and there are moments when things hit me where all the dots connect and the way I think about writing is connecting disconnected dots and the stories that are interesting aren't like I don't the reason I tell stor is cuz if I came here and said like um you know like um I don't know whatever YC would say just generic advice like I

could come here and just talk about I could read Paul gr I always say like listen I can read the book you know this guy the worst VC I ever had in the world was terrible um and the reason he was terrible is because he was actually insecure himself and he really treated us like [ __ ] and one day he called our CEO and he's like I don't know if Shane should be the head of product he went to Western Illinois like [ __ ] Jes [ __ ] you right and he went to Stanford and he was at Kleiner and it was all this stuff you know anyone know Kleiner oh you do I I thought andreon kind of took the fire um and Kleiner was great like I actually love Kleiner Ilia and mimon I love them and it was a junior partner but the

reason it was bad is because when he would come in he would always say these book isms he'd be like oh this is what Amazon does I'm like listen dude I don't care what Amazon does because you've never worked at Amazon like I can read the book just tell me what book you need to buy to like do that um and so for me I try to write about the stories that connect dots that are disconnected because that's what makes them unique so when I think about writing I'm always trying to understand what are the things that I see in the world that don't seem connected that actually pull a story together and then I I I usually write in one sitting always on my phone I never write sitting at my desk I almost only write and I always set up the environment I always I'll I'll like

travel to a hotel I saw a hotel yesterday I'm going to go to tomorrow morning cuz the inside was beautiful and if I go sit there long enough in a notebook and just scribble I'll end up writing about a couple topics I'm thinking about right now and it'll all be on my phone it'll all come out at one time and then I I know not to hit publish and then the next three days for me are just like these manic editing Spirals and I get down to like just removing sentences and rereading it 100 times and just and I wrote one called how to build shitty products like eight years ago and people still internally reference it all the time and at the end of it it said hey like I I I want to show you this product it doesn't do much and I think people think that they need

to write for output versus impact they need to build product for output you're paid to do a job more work more features more stuff and actually internally my writing I try to show the lesser of it the Simplicity of it the editing of it and I talk about that with the team we do a thing on Friday it's called what's the smallest show in tell and then I always congratulate in our culture the smallest demo of the show and tell because you want people to share you want people to share the small things you want people to get over the insecurity of putting it out there um and so for me it's that box of creativity and finding the environment by which I know that the dots connect and usually it's spaces that I'm not usually in where I take ideas that I've actually been thinking about um and you

know I I throw and I throw [ __ ] on Twitter all the time and kind of just see what sticks that's what Twitter Twitter's always just been like a all right think I'm think about this one right now called blockchains are the future of communication I dropped it this morning Brian from here you like and I this already has tens of thousands of views and like 50 people have already retweeted like oh this and I've been testing this because I went to CNBC squawkbox two weeks ago for this talk uh for like a prep interview and all the things around messaging and blockchains and crypto and nfts and identity they don't give a [ __ ] about didn't care not one thing swap Bridge blah blah nothing and I said what if it could protect us from AI they're like that's a story they're like what do you have on that

I'm like what if you have Network level consent what if and SMS actually can't protect themselves and as Bosco exponential there's no way to have proof of human in this entire world and if an immutable Ledger of identity can actually protect your inbox so nothing can get in it except a human if you want what if you could do that and they were like huh and I was like what if it exists today and I could show it to you like huh and and so and i' just been testing it that's a story I want to write you know what I mean and like I just kind of been throwing it out there and that's a very good example of speaking to your ICP right like Shane totally adapted everything that well not everything like cuz you know obviously you have a great mind for these things

but like right he reached for his typical tool and it wasn't going to work so he pivoted like that is what we all just talked about with the ICP I think the other secret I'll share with you is every time I publish an article I edit it publicly for the next [ __ ] four years and every time before you publish a book this is we teach a class at Georgetown and we we make the students publish a book they thought they were coming to an entrepreneurship class and we make them published authors and it changes their lives they get a job because of the book not because of the degree but everyone goes through the same doubt spiral right before they hit publish and it's just like launching a startup and it's just like writing a blog post and we're all like my parents

are going to read this it kind of sucks I've been working on this for a long time it's dog [ __ ] it actually isn't good anymore we literally every time I still do it every day and you never get over that and the the reason you can be a Founder the reason you can be an author is because you unlike most other people in the world will step off the ledge and that moment is the moment this is why business school is [ __ ] for becoming a Founder because you learn all these [ __ ] spreadsheets and [ __ ] sure that's how to optimize and actually business school people are great at growing your business but they don't learn how to deal with the vulnerability and the insecurity and the feeling of incompetence and your parents are like what have you been doing in the basement

for two years like is this real like I don't know like because they're actually validated by you working at Coke right or cat or Facebook they're like my son works at Facebook right that's what your parents want [ __ ] that you know my mom's been like I have no idea what my son does but he seems to be doing all right you know that's what she's been saying for 17 years now um and I think that's the difference that's what you don't learn and that skill is learned by that act and that's what actually putting yourself out there in that moment it's for the pitch for the writing for the book for whatever um and and it's never right and just edit forever and what you really learn is that no one [ __ ] cares about you at the end of the day like what you

actually learn in all this someone said the other day like um don't worry about impostor syndrome because everyone's too busy worrying about themselves like and like you're like yeah actually why do I think anyone cares about me yeah right and that actually there's a there's a thing called um insignificance theory that Tim Ferris kind of talks about a lot and I think it's in that if you realize that like I mean we're just a little rock in a big thing just floating here and we're all just you know oh [ __ ] worried we're all worried and so then you're kind of like who cares yeah and those posts the who cares you know I've had posts that had millions of views and changed my life co-founders workers till this day almost every single person we hire says I read Shane's writing and that's why I

want to work here and it's the ones that actually aren't great but they're vulnerable and real and honest and I still I still edit them I go back I change it and whatever again I already plugged it once but I highly recommend subscribing to Shane's blog and I don't write a lot I think to your point I'm not a oh yeah every Monday I publish that's just not my DNA some people can do that I'm I just I do it with the digest but the way I did that this is something for Founders if you don't send an investor update and you're like not accountable to it and you're actually not creating the story every week create this system by which you will so I told Matt at the beginning we're going to do it every other week so that I can yell at you and you can yell at me right and

it worked we haven't missed one week 147 weeks in and now we let our whole executive team do it so we have seven people on the exec team and I think that kind of system is how you keep yourself accountable if you do have to publish every week what are the two or three things that that you did that really got you to your series a that got you to the traction build something people can feel and if you can do it with someone in the industry that actually has you know the impact of like I mean a coinbase not everyone can but in this bace the bar is so [ __ ] low for Consumer experiences that are great build [ __ ] that people can use that is awesome that is simple we everything's there now from Smart wallets and the app ux and all this

stuff you want to raise round just build something that actually is usable like and I don't I mean that lightly cuz I actually believe this is my final I'll end on this [ __ ] rant the whole Space validating ourselves on fees and swapping fees and meme coins and all this stuff versus great products great experiences real networks growing with value and utility I think we've got lost and I think all the words and jargon of this space need to go swap Bridge L2 fees walled addresses seed phrases no one cares and I think the magic is actually the L2 of the future that wins or the L3 or at this point an L6 someone's going to build the Great consumer experience like a messaging

economy that drives micro economies that no one even has to know that that's happening and when I watch this on Converse there there an app on top of it's like the what's app for xtp it's a real simple app but he built the ability to send money usdc globally instantly for free cash app can't do it vinmo can't do it Apple pay can't do it the C pay across borders and what it was it's all built on crypto rails right but it's using bass at L2 it's using usdc as the token so it feels like dollars and it's what's interesting he uses privy as a login and all these things came together and it's the first time I experiened sending money globally for free where I never had to know anything about crypto and I truly believe that the future if we want this space to work has to be in

that vein and when you start building experiences that people love to use with all these Primitives smart wallets coming online account abstraction privy all this stuff that that will raise all the money in the next three to four years all this short-term fee abstraction if we get lost in like B pump and dump stuff again I mean I think there's a lot of cool Primitives I think it's interesting to watch the meme coins I think there's fascinating things happening of like social dynamics and incentives with tokens and all these incentives but I'm I think it's all going to die I think it's going to blow up we're in the same pump and dump cycle it's going to be this old hype people going to lose a bunch of money and I'm not here to lose everyone's money every three years and I think we all need to

like build better companies and actually build things of value build real networks and consumer experiences and quit this like short-term pump and dump game where people get [ __ ] over and we should build better companies and better cultures that are long-term thinking and Building Things of value and you will raise all the money if you do that that was awesome I need to stop I'm [ __ ] hyped uh everyone thanks thanks for shame with me yeah thank you m [Music]