Secrets of Tech’s Top CEOs | Gokul Rajaram on Google, Facebook & Square

0:00 this unpopular take is meant for one person Gokul rajara so Gokul has this post on titles not mattering and I could not disagree more and this is Gokul rajaram who is wrong just to be very clear for people who are watching this episode oh my God okay I just Goku is so nice I want to get him to fight and get him to come on our show he refused to come on our show maybe this will get him

0:18 to come on our show only few people in Silicon Valley who go on first name basis where you don't need the last names Goku is one of them many of these companies are toy projects I mean when I think of what all four companies I worked there Google started as a Stanford research thing no intention of a company Facebook started as a Harvard thing notion of being a company I think Paul PG is probably right in some ways

0:35 but again I don't agree in the absolute theory of the founder s just had a beautiful understanding of products in J where Larry was a technologist technologist shamat before her had been calling for several months to join Facebook I kept saying no no no no no no do das still I think would have the same interview question for everyone they would give you $100 and say acquire as many customers as you can in one day the

0:57 true genius of good Founders say when to shift into micromanagement and went to delegate when there were crisis Mark Zuckerberg got directly involved Hands-On and micromanaged the hell out of it ladies and gentlemen we have a treat today somebody who is on the Mount Rushmore of Silicon Valley in fact you know he kind of there's a little statue of him above on top of all the other Silicon Valley Mount Rushmore imposters I was trying to figure out how to

1:27 introduce this person because is in one way I think he has had the ideal career in Silicon Valley you know and it still keeps going strong he has done it all he's founded companies he's been an angel investor across a bunch of interesting companies that you would have probably heard of he has worked in some of the most iconic tech companies of the last 15 years he has been in all sorts of situations taking companies public you know when you have these

1:56 lifetime achievement awards at the Academy Awards like this is the kind of resume to speak about but more than that this person is a dear friend and and it's we've always kind of tried to get him to come on the show and he's finally finally relented after a lot of blackmail from us so on that note Gokul rajaram thank you so much for coming on the show thank you thank you so excited to have you you know all the accomplishments

2:22 including like you know board roles board member but I think for us the most impactful has been you know we are in a few WhatsApp groups together we love hearing from Goku and also I think every time we have at least for me over the last few years and gok doesn't even know this but when I have this like inflection point in my career like Goku's probably one of the first person I think of like I have to call them I

2:46 have to go figure out what I should do with my life with my career and he's always been there he'll always whether it is South Indian restaurants in the Bay Area or you know whether I should like take a specific role at a specific company he's always come in with the right advice for us so thank you Gokul for being on the show but by the way I swear we did not prep for prep for this

3:05 particular bit but Ary stole exactly the line I was going to use up next which is when I think about the last few jobs changes that I've had Gokul has actually been the person I've called every single time and gok so so here's a conversation I have on my iCloud notes it is from October 3rd 2017 I've written down notes from it says gokal advice okay and this is because I was contemplating taking a job at Twitter

3:35 and it was a big step up I was going to run a large organization and I was going to work for somebody that you work for and there's a bunch of good stuff in there but you know the thing which really stands out to me is you basically said make every change you want in the people changes in the first 30 to 45 days and just get on with it because people are going to judge you very very

3:54 quickly and there's a bunch of other good stuff in there so anyway Goku thank you you are so spot on but you know maybe what it's one interesting place to start because you and I have and Ary have worked for some of the most interesting Founders in Silicon Valley and one of the topics of the hour thanks to Paul Graham is the so-called founder mode where some that you be work for has come up now one of the ways I want to

4:19 ask you about it is because what is your reaction to founder mode but also what is your reaction to fder mode in terms of you being an executive who has worked for them in close capacity and L large organizations for them well first of all thank you for having me it's like I said it's I just love chatting with both of you and speaking with both of you and it's a treat for me to be here so I

4:40 think founder board is a great one because as as we worked we worked for executives and leaders or Founders I said who who basically if you look at founder mode what's the definition it's I think of it as being closely involved or directly involved and keeping a tight grip on the company even as a startup grows management mode may be the opposite of funder mode and that's basically hire good people let them do their jobs and get out of the

5:05 way I think like with everything in life I don't think there's a black or white I think it's gray I think for example at Facebook when there were crisis Mark Zuckerberg got directly involved Hands-On and micromanaged the hell out of it they we were out of Crisis I remember when the launch of Google Plus happened this was in 2010 or 2011 I think there was a lockdown basically at at Facebook where the whole company shut down for several

5:32 weeks and Mark micromanaged a set of things that Facebook had launched before he allowed the company to get out lockdown basically he was the PM for the whole Pro consumer product at that point but on the other side for most of the companies life while I worked there Mark basically delegated to us you me Ary chery others and we ran different parts of the product and we did our work so I think the true genius of good

5:57 Founders is when to shift into microman management and went to delegate and and and I think you you can't always run the company in one mode or the other you just switch between modes but I think it's knowing when to Jack the same way I think Jack dorsy at Twitter and square he micromanaged a hell out of certain things that he cared deeply about cash app for example he was embedded with the team on a daily basis for the first six

6:20 months or maybe a year but then once once he figured out it was working he slowly receded and let the team do their thing so I I think it's everything in life there's gray there's there's no black how much of this the founder mode you know the current topic dour it's taken you know the Twitter universe by storm everyone's talking about it especially you're seeing a lot of Founders talk about it how much of it do

6:46 you think realistically is about not having the right execs in the right place and and these are not bad Executives by any means but not having wartime Executives during the wartime of the company or vice versa right like you just have probably the right not the right fit how much of it is that versus you know what you seem to say is you know for six months or a particular time frame yes you can get into this like

7:12 quote unquote founder mode micromanage and then pull back but a lot of the the arguments on on Twitter and everywhere else seems to be this is how founder should be micromanagement is a very good thing and I wonder just question I had is on how much of it is just not having the right people to delegate things to I think you're right if if you think of what I always think of life or things in terms of decision trees I

7:32 think if you look at the top order bit it is when to switch into management founder mode and when to be in management mode I think those that's the when but then for it to be successful if the founder switches in the founder mode and it's not the right time to switch or their skills are not suited to driving that particular problem it's going to fail similarly like you pointed out in management mode you switch into

7:52 management mode but if your team is not the right fit if your team is they're not the right fit for the job either they bu the wrong people or they at the wrong stage maybe you hire too many late stage exacts and maybe what a mid-stage environment or if the context is evolving while the leadership mode say liid for example you know if the company's going through transition and you don't have the right skill sets to

8:14 manage to that it will fail so I think there is a when and then there is what does it take for each mode to be successful I I think each of them can fail you could switch correctly but still you were not have the right people the right context etc for it to succeed I think one of the reasons I think this has got a lot of people so pissed off and you could disagree with this

8:31 entire framing I think there's one Camp which believes that over the last four or five or maybe more years that there has been a rise in the PMC the middle management the exec player at various tech companies and just with the US of acronym who may not understand what it takes to run companies especially through hard times there's another school of thought which maybe thinks that that there is almost a obsession with a great man Theory but applied to

9:01 technology that Founders and CEOs are the only people that matter as opposed to any team member below them so when Paul Graham for example wrote that piece which kind of sparked all off he basically says and I I might be misquoting that lot of the management that comes from large companies are very very good professional Liars I think he might have said exactly words to that extent I'm kind of curious to get your reaction to that because I think you are

9:23 right in terms of people know when to step back and step out but was there an explosion of middle management and upper management who know know to do the job are founders right in trying to step back in and do are they right do do it in every single domain even when they might be familiar with it this I'm trying to get you to offer some spicy takes over here gok I think I I don't like Absolut statements what I disagree

9:47 I think Paul PG is probably right in some ways but again these absolute statements are serve no good because they I think influence impressionable Founders to be have a certain way all the time the reality is I I can't imagine Facebook being built the way it was without Cheryl Sandberg being a close parter to Mark I just cannot I think she was as critical to that face of Facebook so as Mark was and and so on

10:11 so forth I think similarly Google with Eric being there and Larry Sergey needing that mentorship to grow at Square it was Keith Rea along with Jack dorsy at door Dash it was Christopher P along with Tony Shu so every company I've been at I've seen that there has been a strong number two or number one prime which should call it who supplemented the founder I don't know airbnb's details but I bet the you know the other Founders or there were people

10:37 there without whom the company wouldn't have flourished yeah I don't agree in the absolute theory of the founder well absolute takes are very very good for getting reactions online re but okay so we might edit out the part where you didn't see absolute things and we'll just edit in the part where you say absolute things U okay but so you have been a consiliary a like a trusted exec to many of these books right jack mark because you built out

11:05 advertising at Facebook for many years in fact you know I just for a fun fact Gokul helped recruit me into the ads world at Facebook and then immediately after I joined he left so was in good hands with you joining so I BR this down we we didn't inser that Michael joined me like I took it personally I took it person like you know the week after I started Google was like I'm out right but but I want to get

11:27 to that later but I'm curious like if you look back upon these Executives that you work for and then also you before that you help build AdSense at Google and really I would say pioneered how a lot of monetization works on the internet let's walk through each of them right like Larry Sergey you know the senior Executives at Google they've been studying they've been talked about a lot what did You observe from them up close what were times when

11:54 you had interactions were able to influence them change their minds or they influenced you it was interesting I think Google was the seminal point in my life in some ways as a product person because it was the most fun I almost said the most fun I had because I was an icpm for half of my time at Google and I always feel being an individual contributor is when you really have your hands on the product as you start

12:16 becoming manager unfortunately you get one layer removed and I had the most fun when shipping products myself and in particular for Google AdSense Sergey was an executive sponsor in fact the idea came from him because he basic Al realized very quickly as soon as AdWords launched in 2002 he realized that hey just like AdWords is all about taking or AdWords or search is all about taking keywords and figuring out web pages that match the keywords we should do the

12:40 opposite we already basically taking web pages and figuring out the keywords that match them and finding ads and one of the most interesting lessons I had which I didn't internalize till a few years later was when he nixed something we had built for a long time he used to attend we were heading towards launch in I'm dating myself here in January of 20 in June of 20 3 when we were going to launch Google AdSense and it was March

13:02 and we had built the way AdSense worked as websites apply to be ad admitted to the AdSense program and that's what we built and we were building and so there was a big approval cue we had this Ops team that was ready to approve websites based on a long list of criteria and we basically were reviewing it and then Sergey walked in in into one of the meetings he he was attending he was like what's his approval queue it's done we

13:23 were we proudly said yeah we built this great queue to appr any website that comes in he's like why the hell do you you approve do you need to approve websites you're like what do you mean you know you can't let any website with NSFW or violent content all kinds of stuff get on to AdSense to Google to run our ads why not he asked what do you mean why not he's like look didn't you consider the fact that they could apply

13:45 as under a benevolent website and then after you approve them they can change the website content you're like no that's true and then he was like you know you what you guys are missing is the number one thing that the website cares about is making money fast the first thing they apply and I want to get them to see their dashboard immediately and see that they're making their first dollar first $2 within a few minutes they put the JavaScript on the website

14:10 it should show and what you're doing is you're saying okay now it's going to the approval queue and you might hear back who knows when you have them right then show them the money right then so I want you to kill the approval queue I was like what do you mean kill the approval queue yep kill the approval queue so that was I mean we killed the approval queue and and it worked because what happened is he actually said that Google

14:33 in general is built on this philosophy where even AdWords you could actually back in the day set up an ad with for a keyword and it would start running immediately because there was an instant psychic gratification to seeing your you would search for that keyword and see your ad and for the first 100 200 Impressions it would run and then it would go into an approval que to make sure there was no like you know copyright or other violations and the

14:56 same thing happened with that s once you get because the reality so I think it really solidified a key thing around product Le growth in mind is that you cannot have barriers to the aha moment as you guys know the AHA or the magic moment for any product is when the user gets hooked after a certain experience right in Uber it was watching the the driver come to you in door Dash it was when you get the first delivery every

15:18 and Facebook it was getting to 10 friends and so your new stre is populated so you cannot have any friction any barriers to get into the aha moment we never thought about it that way but that's basically Serge just had a beautiful understanding of products intuitively where Larry was a technologist technologist every feedback we got from him was why is this so small why aren't you thinking bigger why aren't you thinking bigger why aren't you thinking bigger well Sergey it was

15:43 all about the he really I mean he had just incredible product sensibility so I learned a lot from them in different ways but that magic moment thing was something that stuck with the because he killed a lot of work but he made the product significantly better as a result I'm curious how good Google was in that era because you were a little earlier in your career you know you were not the the the Mythic Legend only few people in

16:06 Silicon Valley who go on first name basis where you don't need the last names Goku is one of them somebody says two others names right but but thank you thank you and but you a little earlier walk me through how it was to interact with Larry and Sergey right like how was debating how was discussion did you feel like hey you know I could challenge them and how would you do it it was pretty amazing because it was lar in Serge for

16:28 many meetings and then Eric would join them for some meetings and so it was sometimes two and sometimes three people our VP of product Jonathan Rosenberg and then my direct boss Susan they were I mean generally I mean there was really no barrier between them between us and Larry Sergey just like in in the days of Facebook I think when I was there and you were there you could just directly go in and talk to Mark so they were

16:50 super accessible they were just sitting very similar to the setup that we had at Facebook you could just go and talk to them and what is crazy was that Sergey would sometimes be they had they had set up like bikes in one of the rooms there was a bike and ser would be biking and we would be presenting or talking and they they didn't like one thing I realized that you know I think leaders don't like formal presentations

17:13 good Founders because they realize that formal presentations I sometimes imprecise thinking so they really many times would okay stop this presentation let's just talk about what you're building so I I was kind of nervous initially because I was used to presenting formally and and then slowly I lost my fear because I realized that they truly want to just hear the unvarnished truth and they never shied away from tough tough news I mean that's the thing what they didn't like was like

17:41 give you giving good news and iter because you always initially I was trying to sugarcoat stuff for them then I realized that they were too smart to be bsed and you just give the bad news upfront the other thing I realized was that just like Mark they basically had the most risk tolerance of anyone in the room they were willing to risk it all amazing number of times and we all were much more risk ofs than them as Founders

18:05 and I think that's the thing about Greg Founders as the company kept growing they were willing to make massive bets and massive risks when they bought YouTube we were like oh my God this company there had no monetization it was under massive lawsuits from Wacom and they paid 1.65 billion to buy it and Google it was a good chunk of Google's market cap and you were like what the heck again and again they were willing to bet the farm on things that and

18:28 that's that's a Hallmark of great Founders I think that's founder mode to be honest more importantly than anything else in me where they're able to make I think that's a challenge that a CEO who's not a founder of faces that they don't have because they feel themselves beholding to shareholders well the founders like they remember it was nothing a few years ago and they're perfectly ready to roll the dice I think Elon does the same thing it's perfectly

18:51 to roll the dice again again and make company making or company destroying bets in crazy ways yeah I a couple of stories one Armstrong came on our podcast a little while ago and he talked about how coin base were through some really dark times during one of the crypto bear cycles and he talked about how he was he thought to himself you know what worst case I built a company from my myself in my laptop in my

19:16 bedroom before I can do it all over again and I just don't think even the best hired CEOs and there are some really good ones and I think sometimes in Silicon Valley on Twitter we tend to maybe maybe dis The Hired CEO even but even the best of them can't do that because they fundamentally haven't had experience just something unique there I want to talk about Mark and you to Facebook but you know one of the things

19:39 that always struck me about Mark Zuckerberg is when you are interacting with him I agree with you that he you could have very open conversation with him but I think the subtle interesting thing that he did and I don't think a lot of the others you know great CEOs sometimes do is he would tell you very very quickly where where he stood on the spectrum of the add you're talking about from all the way from I don't care what you're

20:04 working on and sure I'm going to indulge you please feel free go what go have fun go do it thank you for the status update all the way to other end of Spectrum which is there's a piece of paper in Delware which says I own this company and run this company so please do what I say right and there spectrums in between all the way from you I let you overule me but you better be really sure

20:24 all the way to I'm see you and I thought always Zak was very very good about telling you where he stood on that Spectrum so you knew even as maybe a intern or somebody new to the company you knew the framework of how to engage with him and I always think about that in terms of how to engage with somebody who might have a big power level disparity with you I think it's a good point to I I do I mean disagree that

20:49 other CE I think he was exceptional Larry and ser were also very good you knew exactly where you said I mean you can talk to anyone at Google there was I think the look I think the best to engage with all of these great Founders who want to hear the truth is just tell them the truth and be ready to I think the other one is you got to really hear and listen to their feedback one of the

21:08 best examples I think was the foundation of most of Facebook advertising is is something called custom audiences which you probably remember where yeah I think we and that actually came about to Mark he's a learning machine he's a learning machine what happened is Mark Pinkus at Zinga was one of our biggest aders at Facebook so Mark Pinkus is talking to to mark Berg and he was complaining about Facebook ads and saying why the hell can't I reach my customers because Zinga

21:35 was a very whale oriented company like most game companies are I want to reach these whales and Target them why can't reach them I know you have them and Mark Zuckerberg came to us and said why the hell can't you target his customers so that was the audient we were like oh okay he can Target their they can't Target their customers they just need to tell us who the customers are initially it was customer IDs and because Zinga

21:56 already knew the customer IDs because they were on the Facebook they were a Facebook app but then over time it was other ways to identify customers email addresses phone numbers Etc but that was the whole Genesis of customer audiences and now it's a foundation of all of Facebook ads and it also was copied by Google Twitter and everyone else and that was all because of Mark zaker when I first met him in 2008 he had no idea

22:17 about advertising because it a pure consumer company I met him in 2010 and 2011 again when we joined 2010 he had absorbed so much about advertising and the first year I felt his so he was a learning machine like no one else he just learned at a rate that was incredible so much so that his idea was what underlay what what Facebook ad was so but I think at the high so you got to listen to him I think we I

22:44 realized after that experience where I'm like he's not just saying it to say he truly means it and he actually said I want you to figure out a way and he would remember it he would remember it because he also had a great memory almost like it was incredible I don't know if you know it's it's like one of those what do you call it those camera like Memories he would remember the next time he saw me what do you

23:04 think because if you try to not if you like not address the feedback he gave you last time he would remember and he would bring it back to it I think that's the other thing that you just got to be straight up you can't hide you can't dissemble you can't BS them you got to just take their feedback and be direct and say Here's why it's not working and he would I forgot the I think there's

23:23 one or two times where I convinced him what he felt what he thought was incorrect but it was not my opinion ver say it was using facts using data and using using data that is the only way to convince them I think otherwise if it's their opinion versus yours guess what their opinion is going to win yeah every single time when there was a quarter and you had to make you know the revenue number for the quarter and maybe the

23:43 revenue was looking soft you're not want to make it the somebody you know working with de Winer who was CFO then or somebody Nar would pull out like a dock which would be like these are the lever we can pull to make the revenue up Susan Susan me who's now the CFO shout out who just sent me who just sent me a selfie from hro airport with her photo on it so thank you shout out Susan

24:06 right a favorite C for that and many other reasons but but back then and so we pull out this Doc and it would basically have and this it's been 11 years I'm sure nobody Facebook get mad people telling the story so and and and what the doc would have is all these ways where Facebook could make Revenue right it would have things like lower the auction floor it would have show more ads you know all these kinds of

24:27 Believers and somebody would rank it from most desirable in terms of experience or Revenue kind to least desirable and I remember one time you know I think somebody had proposed this get very deep in the weeds but that's what we do this podcast somebody had proposed like showing ads in between every 10 feed story post which was you know we would get ads every 10 feed and Zak came back very strongly and he said something like the extent of look folks

24:53 I don't trust your numbers on how people feel about sentiment how commercial Facebook is you guys show me these things but I don't trust that you guys are dialed into how people feel so two things one is since you I don't trust that I'm going to basically order you to go build out these Frameworks feel free to PE some some of these other levers and finally since I'm the final Arbiter of taste I'm just going to make

25:19 a quality Edition and I always think about that because he gave clear Direction he said these are the rules of the road this is where I'm going to make a Deion and to his credit he was was perfectly right Facebook was not tracking how people were feeling about how commercial Facebook getting and they actually went on built the all their entire sentiment framework so I I have many of these moment from zerber where like wow this is how you both have

25:41 strong opinions but you also give the rules of the road for your exact te okay but you know I I want to kind of get to your story because between Google and Facebook you know you went off and built a startup right like and so talk to us about chabbs you know talk to us about your story there and now looking back what you did right and what you might wanted and and also why I mean you had a really great stinted

26:05 Google you know and there are very few people I've seen who sort of have this like big company experience and Google at that time was not very big but still like very successful feather in your hat kind of thing and then going into the startup side of things so what was the motivation there and how was that whole experience of chabbs crazy enough I think I always like tell Founders that you should not use the same motivation that I had my motivation

26:30 was to start a company with my brother crazy enough he was getting his green card he was one of the best engineers and he still at Facebook after acquisition he's been there for 14 years now and I was like okay you know this is a chance because he was leaving he coming had been acquired by Cisco he was leaving that after his green card so it was I I think it was a wrong reason to start a company that's I had a lot of

26:51 fun but obviously I think you should only start a company when there's a problem and there's something you're trying to solve versus hey I want to start a company so I've had many people who worked with me for me Etc who' gone off I want to start a company with the buddy I'm like please don't make this mistake just because you your buddy is here and you're there you just want to join together and start a company that's

27:09 not that's not a reason so I think we we didn't have the right premise around which to start a company and therefore the other thing compounding it was the global financial crisis we started a company in the teeth of the GFC if you remember I mean we raced around was despite not having a good idea I mean I don't even remember what we pitched we pitched this NLP mishmash of things verticalized NLP of some kind to like

27:35 some of the top VC firms and I think they were already they they just wanted to put money in so we raed an uncapped convertible note I mean there was no saves back then UNCA note a few million dollars and then we had to turn away many people who are put willing to put money into an uncapped note and that that shows you how publishous that environment was in 2007 just before everything shut down nine months later

27:57 and so it's the worst to start a company when you're raising in a publishous environment your mental attitude is all about good times are going to last forever and then N9 months later everything comes crashing down but thank God that happened because if that hadn't happened we would have kept going maybe raising some more money because we we built a cons we built a consumer website back then there were no apps iPhone hadn't released yet and we basically got

28:19 some Revenue got to I think half a million or million ma through SEO and some other hacks and we were keeping on going but then everyone stopped giving you money and and basically I had to raise money from a hedge fund which was one of the most painful experiences because they put in structured things that I didn't even know existed and they but I had to get that and I I had to I basically floated the company for many

28:43 months with but by myself basically and and so when Facebook came Cheryl and chamad before her had been calling for several months to acquire acquire us basically because I'd worked with I knew chamat from before I'd worked chery to come join the ads team and I kept saying no no no no no no because to be honest because of shuis I think that's the other thing I think the number one lesson I have is number one mistake is I

29:08 would have accepted the face of gol for at least a year before I did and not wasted another year of my life and I think any of the founders now who basically are trying to make a go off it I think there is an opportunity cost to all of the things you're doing and you really need to know is there a there there if there's not a there there there's a huge oportunity because you're keeping on doing it hoping for something

29:29 to happen and that's what we were in the mod of we were growing it but it was clear there was not going to be a very big outcome and in the meantime we were losing people I think the thing that catalyzed me was when our one of our key Engineers told me that he was leaving to join Facebook and so I was like oh my God and then I was leaving the office that day and then I suddenly get a call

29:50 from chery again on my cell she said this time Gokul I'm not going to take no for an answer I'm like guess what you know let's talk because I knew that I as soon as this person left a company it would be a because you were a small company 10 people it would be a quick Cascade and then Facebook was the one company that was hiring in basically everyone go to Facebook and then what do we have left so thankfully we we we were

30:11 able to we had some batner and we were able to use that to negotiate hard and get a good deal what was most interesting was Juan Smith was the VP of Corp dev then and we basically got into big discussion on what the value of Facebook would be this is before the Yuri Miller around where Yuri was buying secondary at 10 or 12 billion this was prior to that Facebook's value that it's kind of unclear what it value that it

30:30 was somewhere in the single digit billions something like that and so we somehow we were like look Facebook can become a $20 billion company in in the next five years okay and one was like no 30 billion so we finally converged to okay if they enter China they can get to 30 or 40 billion so we basically did all the valuation and how much how many shares it got based on Facebook being a $40 billion company after China China

30:53 will add another 10 billion of course China never happened and so it just shows you how we all underestimate these things right yes and just we underestimate how compound even at Google I still remember sitting with David Tacker I don't know if you know David terer he was a good friend he was G loock then I think he's back at Google Now David and I were sitting after a year after the IP and saying wow Google

31:13 has a 20 billion I think you know I don't know how much longer it can go man I think we should like think of selling shares a bunch of us used to get and so it just boggles them and both companies seeing them at 10 or 20 billion and now at 1 point something trillion or two trilon trillion or 3 trillion so I I was going to ask you this a little later but maybe this is the right time okay this

31:32 happened in 2008 if you had to Overlay that incident that time frame to now right like a lot of companies especially in the AI World being able to raise at let's just call it very very Hefty valuations what advice do you have for Founders now who raise Capital like should they be going off and taking offer from the 2024 version of shle first of all forget what you raised figure out what the company is going on

31:58 a go forward basis so I think too many folks have too much attachment to what they've raised now there might be some situations where you can't get out of it and your founder and your investors control the company but in most part you can actually do a down down and so on so first and foremost the path you are on does it lead somewhere and by somewhere I mean does it lead to a meaningful company in some way shape or form and

32:20 you've got to be honest and I think you've got to have a have a moment with your advisers you've got to sit down and understand if it doesn't then you got find the best s for the company if it does then take a down drawn take whatever Capital you need to get there because don't let you know don't let the sins of the past hold you hostage when you're building a good company in fact I read this survey a few a few months

32:42 couple of quarters ago that companies that took a dowr their employees are the happiest and the founders are the happiest why because they know that now the companies were fairly valued they're not worried about oh this Damascus SW is going to fall and kill me in some ways now they know that it's going to grow and they know that okay now we've set a real clear lower bound and it's going to grow from there and you get all that

33:04 crap off the table so I would say take a but first and foremost is this a is this a battle worth fighting for the next few years if it's not old take the best exit possible and and be part of a bigger platform because I do think the power law holds true even more true today than it ever has been a smaller and smaller number of companies are going to be the bigger winners because especially on the

33:25 Enterprise side even on the consumer side yeah there is something I heard called foru now which is fear of messing up instead of fear of missing out where where cxos want to consolidate stuff into one platform or a few things they don't want to buy new software they just want to mess up and so they're opting for the safe Choice they're opting for service now or Salesforce or whatever the big platforms are it's harder and harder for individual and similarly for

33:48 consumers I don't want another app how many apps do you do you download I mean yeah maybe we do because we're investors but as consumers you add and delete apps like like candy in some I feel there's only a few apps that get most attention look at apps I'm sure you've seen this right if you look at the apps that go in and out lensa Ai and so on they are there for like a few weeks after they

34:09 got enduring top 10 apps are our old old companies yeah I mean this was something you know since sham had asked this I sort of wanted to ask in a much more broader length right like you're seeing this AI wave so and and Goku like you're right in the middle of it I've seen a lot of like you talking about it on on X on link L everywhere else I'm curious to get your take on in this world of AI

34:34 companies AI native startups what is the implication for these early stage Founders what do you see happening for the incumbents the big companies and what do you think is going to happen for you know VC's investors who are sort of betting in this space like I'm trying to kind of figure out like this all round lens on what happens from here on in this whole wave of company started about 12 15ish months ago we don't know what

35:03 what what this bubble's like when it's going to pop what that's going to look like but what's your take on all of these you know set of individual customers as such I have a very strong take one okay Foundation mods are going to converge around four or five companies and I think there's no more opportunity for New Foundation mods to be built in a general Foundation WS rebuilt I think it's going to be yes they might be built but they will be

35:26 swallowed up just like direct AI basically the models have been swallowed up by Google and now the company is a consumer company building on top of others models that's that's going to happen more and more it's going to be four or five survivors again as a chip player I'm an invest in a company called Gro we'll see if they really supplant Nvidia there might be some competitor I'm not quing for and talk about it application there is where most of the

35:46 action is going to lie I think for us investors and there I strongly believe in the vertical edition of everything what I mean by that is that I don't believe that horizontal apps especially new apps are going to win at all in any way shape or form new apps for example I'll tell you I think customer service customer service AI is the number one use case outs of engineering AI within large companies today but there's like

36:08 15 or 20 customer service AI companies including s your firm has led rounds they're all doing a few million Revenue but I know incumbents now which are about 5 10 years old they were customer service SAS companies they have now released their customer service AI product these that AI product is doing more Revenue than all of these startups combined within a year why they have the data they have the customers they just migrated them it is so easy to build

36:31 these things now that if two kids in YC can build it telling you these companies can just as easily build it and so I mean what I mean by that is there is enough horizontal incumbents who are aggressive and who understand exactly what AI the threat that AI votes for them that is too hard to be horizontal Company by horizontal I mean taking on a function like customer service or or accounting which QuickBooks I'm certain is building QuickBooks and we'll see how

36:57 or net Suite or whatever the case is or even engineering we'll see engineering is of course its own Battleground instead I think you're going to see verticalization by that I mean like I saw a company that was doing content management For Real Estate not for real estate construction because turns out cont manager construction is a very very specific thing where you're managing rfps and proposals and all of that stuff similarly CRM for lawyers I think you're going to see many more

37:25 Niche companies like that that take a horizontal and append a vertical to it and go deep in and don't just build an app but go all the way down and own end to endend that whole process where they and I think that's that's the future of the industry and that's the kind of things I want to bet on where you go deep in a vertical I think I don't believe in horizontal startups I mean obviously there'll be some that win most are going

37:47 to be most are going to either die or be swallowed up I don't believe in functional companies at all functional app companies at the early stage at this point I hate to say it I mean they're great companies but I think they just pH two instead I believe in the more Niche the vertical the better for me I am just going Niche and deep vertical even for horizontals I want a vertical slice of horizontal that's what I want and then

38:09 what do you see on the consumer side of things as such even harder to bet even harder to bet like I said lensa AI I mean they were great apps I mean a bunch of these apps but they were there for you know I I think consumer have lost a lot of money trying to better out series a and seed companies till something gets to I mean we shouldn't even get out of bed till something gets it to 10 million

38:30 Maus and maybe even 100 million Maus because that's a price of Entry I on the board of Pinterest with is 500 million Maus and 500 million Maus is like when you start entering even there look at meta right how big is that right and and so I mean the the the scale needed to get to these things is I I will never forget yikyak okay if I don't know if oh yes yes yes there are couple there are a

38:53 couple of variations but you probably the original College Anonymous posting one yeah diak similarly our our yeah exactly diak was funded by seoa I remember very well talking to them in 2014 or 15 they were riding high they had raised the SE around I don't know why I got connected to them didn't invest for some reason a year later we bought their assets at square and they became the Square Atlanta office that's that's that's it you know

39:19 I don't know what happened between the rounding at and then BEC the Square Atlanta office one or between one and two years that's what happened so theous it so fast in consumer so fast well I think there's a few things happening one is the incumbents are very very smart and they know how to adapt two things like if you have a new ux metaphor Instagram is going to stick it on the top of their app almost immediately

39:45 and so is every other platform that's number one second is I do think there's a little bit of customer consumer exhaustion over trying these things and bringing your friend graph to these things Nikita Byer had this great point about as you get older you really don't want to invite your friends to new things and and there's only so many apps that you want to invite people to and iOS and apple have made it harder and harder and harder to invite people

40:12 to essentially social experiences and that's gotten really really hard and but I do think look there are some promising spaces I would say AI friendship is very interesting it's weird and raw and some of it is maybe not something you can open up in your screen in the work context but you know there's something interesting there because people are actually interacting these things for human huge amounts of time but you're right it's absolutely it's kind of a weird space

40:41 for consumer though of course A friend of mine will point out that only fans might be the best consumer app company of all time just that you know obviously they not be investable for all the obvious reasons I want to ask you maybe a flip side of what you talked about in terms of the fundraising for AI companies and and also fundraising and your ra funding and you kind of just floating around which is in 2020 2021

41:09 the zerp era so to speak there were a lot of companies which raised very very quickly growth arounds and you know build sizable businesses especially in the SAS sector I would say some of the companies have large amounts of money but they're not exactly growing at the way that they could there's a lot of haziness over what is your path to an exit thanks to you know all the blockers with IPOs and acquisition out there now

41:34 I want to make it a little bit focused on the individual which is you and I probably know a lot of people or get asked advice from a lot of people on carers right but the specific scenario I want to put to you put to you something like this you are age early 30s mid-30s perhaps right you are a director of product or director of engineering at a CDC s company raised a lot of money at

41:59 like maybe a billion billion plus million minus cir 2021 it's growing but kind of flat you know you're kind of getting up there you're getting oart but you know you just you're just kind of floating now usually around that age and the point your career people have you know they they have like one of three choices they really want to think about one is I'll stick this out I I've been here for two three years I have an

42:21 organization I'm respected I like it here right let's just kind of see where this is going even though the growth might have flattened out option two I'm getting a bit older right if I if I going to do a startup now is the time because if I get older and you know I have kids or life experience come by or whatever I may lose the optionality to do a startup you want to do a startup or

42:39 join a very very early stage one now is the time number three is let me play it safe let me go join join a Fang company you know make a million or two in rsus immedately liquid you know help pay for my down payment in San Francisco right but I probably had variation of this conversation where help people talk through these questions and I'm sure you probably had words of these conversations now of course it is a very individual

43:06 preference you can say well kind of depends what you want but I see lot of people like I don't know what I want because I'm kind of stuck what what is your advice because I know you probably had these conversations with people and what is your advice to folks who are in this situation it's a great question all of us have you know faced it and have had convers with people who faced it first I would eliminate option number

43:22 two I think joining a super research company tantamount to basically being a found yourself I feel it's basically taking the same amount of risk as the founders but with you know 100 the reward if you like the idea you should just probably create a better version of the idea but in general I think you shouldn't join a very early stage company I I don't think the RIS reward is worth it you should first of all you should figure out what your

43:45 situation at this company the objective two objective things to look at are one how's the company doing and then how's your career at the company doing and both matter if the company is actually not going to go anywhere then the reality is and you need to again have the same conversation that your CEO is probably having with the board if this company is not growing at a rate that that makes you confident that there's going to be an exit and you

44:07 already spent two and a half years that means you have two and a half years of equity vested and you have you know a bunch of things you accomplished I think it's time to leave second if the company is doing well but your career has flatlined and your learnings are Flatline that's the other reason to leave where you basically feel like you are basically layered above and below there's you're not really growing as a person as a leader you're not really

44:30 accomplishing anything that's another reason to leave I I do feel like regardless of the company if you don't feel personally personal growth you should leave and then the question is where should you go I think at that point I think then I think you should only go to a Fang personally I feel if you have not had a brand a good brand on your resume because the reality is this company you know it's probably one of

44:52 100 companies and no one really knows what they're do most likely and it's very hard for people to understand are you good or not so I know many people who needed that credibility of working at real scale and they went back slightly later because they worked at a bunch of startups and they said you know what 10 years of my life I've just worked at startups that have not gone anywhere that are moderate exits let me

45:12 go and get myself credentialed and work with the great Network at a Microsoft or at a Google or at a Facebook something like that so typically you you advise people to start earlier at these companies and then join younger companies but people have gone midcareer in the to them but if already if you already worked at a couple of these companies and you already have the credibility of having done well there I would go for a midstage company I would

45:36 always choose a mid-stage company and I feel someone said this I think who said this in general you can think of life as having 10 shs of four years each assume you say for four years of a company and you work for 40 years four years each 10 shs basically if you are a good learning if you're good at learning you start getting better and better identifying what are the characters of a good company a good founder and a good role

45:59 that matches what you do and I think I have to assume that a smart person after doing playing the same thing at joining M Stage Company three or four times will hit the jackpot both in terms of the role and in terms of the company for me I I worked at a failed Optical networking company when I join left the valley or when I came to the valley that was my first job and second job was

46:20 Google and third was chabs fourth was Facebook so it's it's basically getting get better and better identi Ying I've seen this time and again maybe you fail your first company join fails you join a second company you don't make the same mistake of choose the company and then you maybe it still fails almost certainly if you're smart the third company will succeed and will do well but I am all about mid-stage companies I think midstage companies offer the best

46:45 risk reward they offer growth but they also offer like lower downside and they offer the opportunity to have impact and growth with Good Financial upset we all join mid-stage companies I think you know sham when you join Twitter or Facebook both of them were midstage companies and midstage for me maybe they were slightly later but midstage me is around 500 to a th000 it's like oh my God that's a lot of people but reality is great companies

47:09 are 5,000 10,000 people 500 people is still I think 500 people is still a little bit early maybe you join between 100 and 500 but I would never join a 50% company unless it was WhatsApp or something where they can scale Infinity without without adding people well I think I mean it's hard to tell these things ahead of time I do think there is a version of this which is really playing out right now for a lot of

47:30 people because a lot of folks raise a lot of capital about roughly 20 enough three years ago and they all have a lot of money left and they have sizable business but they're not growing and I do think there's a set of people who are you know directors VPS and are like okay how long do I wait do I take a shot at it now it's interesting that you say that option one building a startup is

47:55 not for someone because I do think because I think for a lot of people if you are part of Silicon Valley and you hear the lore you hear the stories of the Jacks and The Elon and the marks and the lates and the serges it is very hard to not aspire to that status but you need to have a specific idea you need to have a you know you need to have a problem that is so like that is like

48:22 basically yeah exactly like if you think about how both square and Twitter started right yeah many of these companies are toy projects I mean when I think about all four companies I worked at Google started as a Stanford research thing no intention of being a company Facebook started as a hardware thing nor should I bring a company Square started as this very specific problem that Jack and Jim had where they built this thing and it became a company do das started

48:45 as a Stanford you know class project I think if you try to explicitly engineer a company by reading about a trend on Tech crunch I think those are hard to pull off I can I can I disagree with you there right like what is what is the company let's think about the two large foundational model companies at the moment right open Ai and anthropic the origin story of one is you basically get a bunch of people with Sam and Elon and

49:09 look there are like end versions of the audience but they had a big Vision right they wanted to solve AI they didn't actually read about a trend it was before it became fashionable and that's the thing right it was before there's no there's no Tech crunch article on AI like Al probably scoffed at it when they started in 2017 people were like oh yeah this even even you know I know so many phds who were like we all did computer

49:27 science AI was a fail thing neural networks were fail they started then and so it was being nonconformist unfortunately what happens is most PMS are conformists so they'll Out start a company based on what they're Tech crunch I think you actually that's the real truth unless you have some deep faith and belief outside of I just want to be a Founder like the problem you're trying to solve is I want to be a Founder so that's the problem you know

49:50 you need to sell something else and it has to come from within you almost in some sort of like a spiritual ideological way and that I think is going to motivate you I see this even even when I was starting companies right like sometimes you just see like really bad advice being given around right and it's like part of it is you have to start companies in the hot teams in the hot topics like that's like you know

50:14 General sort of if you talk to a bunch of folks there like what you read on Tech Branch what other people are getting funded on those are the things that you should start which you know to me those are never true like look at like the Ubers and the door Dash door Dash was actually in my batch of Y combinator and they were so different from everybody else who had come on board and you know I at that point I

50:38 remember even they through the application process and interviews people were like apparently they wanted delivered food to Suburban areas like this just seems like such a joke and so a lot of these ideas stand out as just like absurd and ridiculous because it's just stands out so differently from what is consensus and what is the theme right now the other thing I see with Founders is it's it's a problem that they deeply have and they deeply solve

51:02 there are always exceptions where I've seen a couple of companies where the founders would just be like we looked at all the problems that are sort of interesting and we just a tested a bunch of websites a bunch of ideas and we came up with this thing very very rarely I've seen that work but more often than not it's this like sort of this nagging pain this problem that they just can't like forget about all consuming it's like this thing that they

51:28 would like if you sit with them for dinner lunch whatever this is the only thing they want to talk about and it's like sort of annoying right and these are the people who like build that and figure it out because you're going to have these huge ups and downs through the the the stage multiple stages of the startup building side of things and these like the belief in the Pro solving the problem is a thing that Tides them

51:49 over that makes them feel like they can go do and to me that is truly the founder mode side of things right it's like no matter whether there's a recession or your first employee quit or whatever happens you're going to have to like see it through because how can you not it's the Brian quote that sham had earlier right the founder mode that's a Founder mode statement yeah I will go back to sitting on a laptop if that's

52:10 what it takes because I believe in this so much yeah yeah but I'm going to still build this company all over again if it comes to that yeah yeah okay I'm going to do something I'm going to screen share and play you a video and and get your take on it this unpopular take is meant for one person Gokul rajar okay so when you see for the viewers to see this episode right like make sure to

52:32 tag him and to make sure he sees it he's a good friend of mine so which is why I have to call him out when he's completely wrong and so Goku has this post on titles not mattering and I could not disagree more titles not mattering is one of these things that people tell you to make you feel good about yourself and them so Gokul St and this is Gokul rajaram who is wrong just to be very clear for

53:02 people are watching this episode oh my God okay I just go is so nice I want to get him to fight and get him to come on our show he refuses to come on our show maybe this will get him to come on our show before we get into fistic cups over here gok summarize maybe your Tweet storm on titles and I can tell you how wrong you are no but it's not even just a tweet storm this is you post this

53:20 every few years I've in the history of no you've written about it there's a medium post about it you write about this every few years look I think again I don't want to be absolutist but my take is that Founders should not award titles too quickly in particular VP and directed titles should be should be avoided being awarded for as long as possible as long as possible the earlier you introduce them in your company's life the more pain you're going to have

53:47 in fending of people who basically aspire to just be a VP director and you're going to get everyone trying to basically aspire to be the a VP of director every every possible opportuni so I think VPN director has the ban of startups well I would say okay I think the framing I would give you is well let me give you a situation then if you are let us say a senior person and you're joining a startup and the

54:12 founder says you know what I followed Gokul rajaram on Twitter he posts this post on title not mattering so I'm just going to call you engineer right and you just left Google or Facebook and you at a D2 but those of you who know what that means you know you're like a senior level director whatever and I'm just going to call you engineer because because of Goku's post right if you were that person right would you negotiate a

54:38 title or not and I want to make a followup point because I agree with you that Founders should resist title inflation but I kind of want to disagree with you on how titles provide legibility within the organization I think I've actually had the situation because there are enough startups now who have adopted this now at employee number 200 or 500 you might actually have some hierarchy and maybe you have a director title or something like that

55:02 but I think you get away with lead and head off for a very long time I think lead and head off was the two titles I said they basically allow you to articulate people's roles better so you could say it's a product lead or maybe head of product but basically don't give a director and I've seen if that here's the deal if as a Founder I see you negotiating and saying that's the only thing that matters impa I had a

55:26 company which someone from Google tried to negotiate they they negotiated the com got to the right com negotiated the scope got to the right scope and then said that they were a group product manager at Google and they were only going to join where if they got director title and the company said no and they joined they joined because the reality is no one else see the reality is you you cannot have other people as soon as

55:48 someone else has a title of director at your company that opens the door for everyone to negotiate why does it only stop at group product manager and the senior product manager also say I want to direct your title and then you open up so I do think I think it's easily possible to draw the line and to and to basically say let's let's think about what matters to the company scope and impact it's not title it's scope and

56:09 impact if your title if your role can represent scope and impact well I I have seen the difference going from companies with with no titles to companies with titles and the difference is is profound and and how people behave what they optimize for and what they what they advocate for for themselves I want to disagree with your framing which is from the point of view of the founder right I'm more interested from the point of view of the industry and

56:32 maybe the person asking for the title in the first place because my push back would be across industry you made an earlier point about how you want to get the brand on your LinkedIn profile right like you want to get you know one of these iconic companies in there because it tells people okay even if you had a couple of Misses you're still cable enough to hang with the big you know the top tier people and I would say if

56:54 you're not part of one of those Elite companies and and every 2 three years those Elite company Silicon Valley changes titles are the way everyone else in Silicon Valley is going to judge you and they think about it if if if if you meet a VP product from one of these SAS companies that you mentioned are you really going to look at the title you're going to go three levels deep and understand what the hell did they

57:16 actually do because VP product at a no-name company that you've never heard of you don't you can't actually calibrate how many people do they actually lead manage what what is the scope scale of the revenue of the product that how many customers did you get all of those things you actually will instantly I will disregard the title for sure at Google face yeah well well sorry but I would say the counter point is if this you know let's call it

57:42 this you know the SAS company which has done well but maybe not doing the super well now if that person was just a regular product manager with no title they would probably not show up on most recruiter screens they would probably have a much harder the counterfactual would not be that life is easier the counterfactual would be the life is harder like for example I think you and I can you know I have been lots of

58:02 situations where somebody would be like oh that person is a staff engineer right like and if that person is a staff engineer it has a certain level of credibility and respect we're going to take them very seriously I think the new Trend Goku I'm curious to get your take on it is for fan companies to award CEO titles like that's interesting new trend and for a lot of other companies to start awarding distinguished fellows which is

58:26 another interesting new thread but I do think president president titles also oh yeah that's right that's right yeah we see a lot of those yeah I I think this one I'm deliberately similar to Paul Graham I I'm deliberately taking a more auth or more hardcode view with titles because I think we need because it's so easy to give in fact one of Ben hov's amazing post is about titles and how it's something you should give I

58:50 think both Mark and Ben strongly believe in giving titles as a as a negotiating lever because it's an easy L to give and I think someone because they're so influential I think people I do think you need to have a Counterpoint so Founders know there is another way of doing things and maybe you land somewhere in the middle look I'm not saying no titles forever I'm not saying that at some point you will need to have

59:10 titles I'm just saying defer titles for as long as possible it don't don't give tit in your first when I see a slide Deck with the first four employees being CEO CPO CTO cro there's only four people in the company because you know it's the four College room colle roommates or you know the four Founders who given this a title I'm like what are you the cxo of I will this AR and I uses line a lot

59:35 which is from succession where you know kulen will say he' be like I'm Co whenever there's operating I'm chiefing it right like and you know we use this line a lot by PP by the way by petp is if you are a sub 10 person company the CEO should not have a chief of staff right like I I I I I don't know what staff you're chiefing you know I don't know what you're doing but the CEO should not have a

60:04 chief of staff and I'm surprising every once every year or two I'll run into this company and empirically and maybe one of them will turn to amazing company but empirically those things haven't tend to work out and I'm trying to draw some correlation know that but yeah if there there is a c that person better be chiefing something important Amen to that I think I I think a bunch of Founders are looking this going holy I have to make a bunch of changes

60:28 overnight like before Monday morning I got to fire that Chief of Staff I got to change all these titles like all these things that I have to take away from this company it starts tonight okay so I want to you know it's because I this episode we kind of like you know we kind of interl through various parts of Goku's career because he really has you know really like like done it all and I want to you know

60:52 we talked about sort of the almost the unhappy case you're stuck you kind of figure out what you want to do I want to talk about a happy case and I want to go back in time this is I think 2 months after I joined Facebook because I know you left immediately after I joined you're doing really well I think this is this is shyam's therapy session like 11 years later he's trying to hold go accountable can I can I can I can I say

61:14 this because gok helps sell me into joining this ads World on Facebook you you had a great time didn't you you contributed so much it's great for Facebook great for you thank you yes I do agree and thank you because you know this also probably just means goal's like man all the Riff Raff is coming in I got to go like this is just not the place I swear like literally the first team meeting we had was Goku was

61:37 like I'm out my kudak was also amazing he taking over see you guys I'm like what right like but anyway so but I want to kind of go back to the time because and I didn't really know what was happening was Goku was really crushing it at Facebook he was running the ads product organization and Facebook ads at the time had really turn the corner we we knew we had something really really valuable it did not need my help but thank gole

62:03 for bringing me on so and and let's just say Goku's you know I just say with Goku probably you know if Goku kind of stayed at Facebook at the time you know you know had an amazing journey at Facebook you know probably made you know a bunch of money Facebook stock well all of that so you kind of had a good spot over there in terms s of like projected outcomes at where you were in your career but you choose to leave

62:27 Facebook and U and where you kind of known as the ads person across the industry and kind of take a risky bet and you go off to square now block and to run product and engineering and I hly go was a happy case because you are leaving something like a sure bet on the table carer reputation money to go to something which didn't seem as sure at the time so maybe walk us through the experience the thinking the interactions

62:55 and how you went about that it's funny because you know I think it's it's funny you bring it up because as I reflect I I realized that I always try to do this where I think U at Facebook my boss sorry at Google my boss F the first founder award were planning to be given in 2007 and she said I was a I was basically going to be one of the recipients of the founder award which is

63:19 a large stock Grant and I said please don't tell me what the amount is she like why because I plan to leave in months he's like no let me tell you then you won't leave I'm like if you tell me I might not leave but I want to leave and so in general I realized that I have to you know I I like going out in a good place where I don't want to be I I

63:39 don't actually follow football but John El went out when he won the second Super Bowl with the Broncos that's when he said he right after winning the Super Bowl he said he was going to retire and so I like I like you know I think you're kind to say that I think I was doing well I think it was it was a great at Facebook you're right that we have figured out thanks to a lot of work that

63:59 the mobile ads team did for app install ads and all the other stuff I think you could see the next few years being up and to the right and so I think you like I said my framework is always is the company doing well and am I doing well and I was doing well personally but I realized and I think this is one way I always say that the way the the inbound you're getting from recruiters and

64:19 others tell you how you're perceived in the market and I figured out that I was being perceived as an ads person through and through every role I got every inbound I got was to run ads at company X or company Y and I realized that I had done ads at Google and I run ads at Facebook and I felt that from a domain point of view I just wanted a change to do something completely different because I'd spent now you never done ads

64:43 before I'd done ads for many years at Google and so I I just wanted to do something different which would which would expand the set of things I was good at and then Square also offered the opportunity so it was something completely different than what I had done and it offers the opportunity to do something different on the functional side is not just running product it is running engineering and design so because of that reason I I was I

65:05 consider it super strongly and then I asked myself the question assum in two years Square goes to zero because like you said Facebook is going to I always say it's a good question to ask would would the opportunity of saying at Facebook have been better than opportunity at Square I would have said no because what would happen is square to zero I would still have been on the executive team of a company that that basically had reinvented and built some

65:29 very you know had built some revolutionary products had run product designer engineering this no title it was product enging and design lead but I also had the chance to be part of completely different network my network was all in the South Bay Mountain View and and Meno Park and so on the Square Network I had never been part of the San Francisco Network that you guys were part of I was so I felt that it would be

65:52 a different it would be a sea company a venol COA companies I never engage with them at in close proximity and and also Jack and and and the Twitter and square crowd so I felt from a network point of view from a domain point of view and from a functional point of view it would give me a completely new set of experiences and I think I always think of careers as being in you you are in

66:15 you are in like sewing mode where you SE the seeds and then in harvesting mode later on I felt that I was still in sewing mode where I was still laying the groundwork and I was not in Harvest mode if I was in Harvest mode I would just stayed on at Facebook and just rested invested or basically not rested invested but just done a great job at Facebook hopefully and and but I felt I was still sewing and when sewing you

66:37 want to build a diversity of experiences across domains functions networks Etc and you've got to keep doing that and I felt I was not going to do that another five minutes on Facebook you you talked about this as a regret minimization framework right and it's one of my favorite things because it's sort of applicable not just to career but to like life decisions as well where you look at it and say if I didn't say yes

67:01 to this would I regret this later and and you also think about you know downside protection like what's the worst case that can happen if you actually did this but what would the best case look like right if you said yes things were up to the right great if things went to okay but you'd still have this Foundation that you built on top of exactly and so go from there so that for me person personally has been

67:26 really helpful I want to talk about door Dash you know we briefly touched on just door Dash you know I love the founders the founding team was just extraordinarily good what you know when you joined you joined in 2019 why door Dash it's a very different bet I mean you done cavar at Square so you sort of known that area but there still door Dash is very different and how was it there like how was it you know processing their first

67:54 set of a like what was that whole experience like do Dash is a great example of what I call and you you know this because we're in the YC batch of where it's a great example I give to say please don't overbuild stuff the first version of door Dash was a website without any clickability there was a PDF on a website palal delivery.com and the first order all the orders could only be placed by phone you couldn't order and

68:18 Tony was a customer service person on the other side and he was an internet Square before that so he took a bunch of square readers from the square office and the first order was basically people paying with the he would basically pick up the order from the restaurant get the order pick it up you place the ordera pick it up and he would go there and take the order in person on a square reader so that was that was how he they

68:39 engaged demand without building any product I don't know what San and Andy Andy did initially but they basically put the PDF off or something but yeah I think they probably took phone orders but that's what I say I mean look that's that's how they gauged that there was demand for something that people were not able to order delivery it was all done with square leers no payment no stripe nothing and so that that philosophy has always been part of the

69:02 company and so to be honest caviar was a I knew the we knew at caviar when we were part of square in 2018 we were doing very very well I think we reached 500 million in gmv in 2018 or something but then we till then do das and caviar had operated in different geographies do das had been the burps cavier had been in the cities and we were like okay we but then I was I was working in San

69:28 Francisco we started seeing bus ads or door Dash in early 2019 because it just completed the SoftBank ground a billion dollars that's what I knew okay we when we went to square our you know basically our our peers and asked them for more budget Square as a public company they ain't any budget to do marketing for caviar and so we knew it was the beginning of a long Decline and end because awareness basically was was basically I think you know we ran a

69:54 process and thankfully we got offers from all our competitors we also knew there was some Game Theory because we knew Postmates good friend Bastian would also probably have to sell at some point because ultimately consolidation was going to happen so I wanted to get ahead in the process ahead of Bastian ahead of Postmates because whoever bought if someone bought Postmates that' be one less person to buy one less company to buy us and so we thankfully

70:18 got ahead and and I think door Dash I felt that and I was a key man in the deal so I had to go to Door Dash as part of it but I also felt that it was it was a job not completely done at caviar because I was not able to do what I wanted to do which is get to a scale Beyond a billion and do Dash just provided the I mean it was the best

70:39 decision I'm so happy ultimately Square had to make decision not me that do das should buy caviar I was I was involved in advocating for it the number one thing about this company is that I think Tony the CEO I personally think is the closest we have in the US related to Jeff Bezos he's the closest person we have to Jeff Bezos he's about 15 15 to 18 years younger than Bezos hopefully has another 15 18 years because the

71:05 level of operational rigor the company has is unmatched give give us an example like how give me give us may is an example I think I I learned that there was U there was a metric called missing and incorrect items which is what percent of your orders are missing or incorrect which means if an order Missing or incorrect that's a pretty bad customer EXP and it was a very small percentage it was like.1 or 2% but there was a team

71:32 with a GM which is a strategy and operations person and a PM and a ton of Engineers their only goal was to reduce this number every single day and so and it was a very small number so even reducing it was like very painful so it was like reducing it from. 21 to 0205 but they would just every every week they would send a weather report saying here's how much you reduce by here's an things are doing and so there

71:56 is infinite number of projects like that in the company where it's a small set of people taking a very small operational thing and just going deep down and just doing it and it is crazy I'm like and there is and Tony and a few others synchronize all these together and and just it is such a complex business because remember it's not a two-sided Marketplace it's a three-sided Marketplace it's a three side of mar that makes it infinitely more complex

72:22 with a fourth side which is the damn cities involved now cities right they have their own set of restrictions so what you can do in New York for the driver or Seattle for a driver is different what you can do is Austin for a driver a red State versus Blue State thing so it is a supremely comp I would strong just getting Ravi inukonda who's now the C CF of do Dash to to come and talk the other thing do das did was

72:44 hold Talent the Tony one of the things he's excellent at is go after undiscovered like Talent pools so for example most of the do das people didn't have any especially the operators they didn't have any experience at any company before or any of the like branded companies that we talked about they all were like division one athletes or basically launchers at door Dash and and Tony asked one of the things that I learned from Tony is that even most

73:13 leaders they talk a good game but they don't they can't do anything so do das still I think employe number 500 would have the same interview question for everyone which is towards the end they would give you $100 and say acquire as many customers as you can in one day or I think they would even give you a number acquire a thousand customers in one day with this $100 some people would just opt out of it they would say look I

73:37 can't do it or protest this thing this is I can't do this the best ones and no one ever even acquired close to a thousand no one but the best ones would take it break the problem down and try six different things have a hypothesis and that's what they want to see that you're Fearless you'll go out and try five six different things and you'll figure something out he what does you go I want to ask if do you remember

73:56 any of the interesting or good answers to that question I think one person went and stood outside gyms first and basically tried to do a partner they somehow managed in the day to partner with the local gym and basically gave coupons they created fake do Dash coupons and gave it to the do Dash was already giving $5 off they just made it into $5 off coupon and printed it out and gave it to people who entering the oh W I think I

74:20 misunderstood the question so you you had to actually do it it's not like a theoretical question you had to actually go you to go you had to go out and do it I love that I I love this so much I mean in my mind when you mentioned the question I was like I started thinking about ideas that I would like try out right like this is sort of it it's it's such a great question for like people who can who

74:40 love this sort of Scrappy operator type sort of I would say that any many many product roles now many roles have like projects or questions that you have to do you have to submit case yeah the best answers to every question I found across square and door Das compan that have seen this have been candidates who've gone out and interviewed real life customers right at Square we had a customer of Premium insights which is like we have a insights product should

75:06 we have a premium insights product if so why why not instead of saying yeah I think you should have premium insights product here why go and talk to 10 customers how hard is it go and talk to 10 10 Enterprise even 10 five Enterprises is not hard to get to right go and meet your buddies who are V engineering can't you just stop instantly it it it elevates what I think of you because now you framed everything

75:27 in the context of the customer versus my own opinion and so it's so easy to do to it I love it to customers yeah it's such a such a great question man at some point at some point I got I have to go steal this sort of interviewing for candidates like actually like a real you in the role where you can do it you should yeah I know this is so great this is awesome wow got them number one

75:53 question every role in my opinion should have a work work interview question cor Dev always had a question what's the number one company we should buy under the radar company don't give us standard example yeah engineering already has that because everyone has coding interviews I think we slowly started seeing that in other roles over time yeah it's since I haven't done a had a Facebook product interview for a while since I I can I can PR my favorite

76:16 interview question I used to ask back then which was I used to people would show up and we were interviewing for like product leaders it kind of somewhat senior product leaders I would say okay so name a interesting company in Silicon Valley you know which is not Facebook and they would usually come with something back then it would be say Tru or qu or Uber or some such thing i' be say great right like zck and the CEO

76:41 of the other company through Houston or Travis over went out had a drink and they say what we should merge forces right combine our companies and they but wait to do that we need to pick a product which shows off the Synergy of our companies work together and they appoint you and they give you six months and they give you a crack team of Engineers to go build something which makes tries to make this merger makes

77:03 sense so what do you do right and what I us lot this question like every single person would be like damn it I should have picked a different company to start up and but it was one of these interesting things where it was very clear there was no right or wrong answer and you're doing a lot of these interviews you just kind of bored you already to get some interesting discussion going back and forth as up

77:21 first and so it was that was kind of my go-to move oh yeah I love that question yeah I love that question you know we've sort of gone like full circle right I you know gok I think the thing I we like about this interview and this conversations we can ask you questions about founding companies we can ask you questions about middle management can ask you questions about m&a scaling acquisition you you know it's like this whole cycle of every

77:47 person at Silicon Valley who like sort of working in any capacity in Tech will sort of relate to this content here I like you know since we're getting to the end of this I like to wrap you know these conversations with this one question I like to ask which is if you're a Founder today you're just starting a company today what advice do you have for them could be in the context of this current Space Bubble

78:10 post bubble whatever from your own experience as founder what advice do you have for founder starting companies today keep the initial team very small till you prove out the hypothesis you have in other words regardless of the capital you've raised I think many strong Founders are able to raise quite a lot of capital but I think keep the initial team very very small and I I actually I read something that Max lein said at some point I think it actually

78:34 is very good for the initial five or 10 employees to actually be fairly fairly similar in their world homogeneous they think about it versus I I think it's because you just want to be fully focused on that one thing and not have anything that to disrupt that so I do think find your trusted in fact if you can't find eight or nine people to hire from your own network you're probably doing something wrong that's the other thing I'm like you need people

79:00 in that first nine or 10 people that you trust in fact I I I think that's and keep the team very small op operate the company in a set of hypothesis the first hypoth is are there is is this problem a paino that enough customers have second can I build a prop product to solve this paino third our customers so I think you need to pose the question answer the question and then maybe expand the number of people working on it you have

79:29 to structure the company a set of hypothesis I think don't over hire hiring should be AOG hiring or spending should be orthogonal to Capital rais I think especially now I think with thei companies right you can Sam Alman had said this in some talk it was I think it was sort of meant to be bombastic but I truly believe in it it said something like you can now see one person companies that have like billion dollar

79:51 outcomes or billion dollar you know Revenue and because of how much you can sort of push onto the AI layer and the AI stack you don't need as many people in the early stages of company building at least to be able to scale a business as such exactly right I like could but gok I just want to say this has been such a interesting conversation and Gokul is genuinely a dear friend even if I think his top

80:22 idea on titles is totally wrong but he is the person it's kind of funny because you saw AR and me individually talk about how every time we had career changes or we're not feeling good about where wewh Goku is the Godfather that we call upon you know and ask for advice and I know we not alone in doing this I know a lot of people look up to him a lot of people want him on this

80:46 their cap table in their boardrooms and Goku you're just the best you deserve just like Prince or share you deserve your one name moniker but this was so much fun and you know we should we should do a future version of this some other time too but no thank this is so much fun this is great this is fantastic well you guys I think as sham said arti both of you run these WhatsApp groups that I'm part of and

81:11 they are such a huge part of my life so I feel like you know I feel you yeah so many years I think freom just does this to like stir up like you know these like WhatsApp groups where he just has to like throw out the most controversial statements that's his job because he his job is to be the host in some ways right his job is to get the conversation flowing yeah that's a key requirement of one this is Manifesto for

81:37 running a group I remember that very well you need a host like sharti yeah yeah I mean just today Goku shared between Zach and Jack and Tony who is his favorite CEO but we will not talk about that here so on that note on that note C is a truly Delight thank you so so much one next time thanks man thank you thank you