ABOUT THIS EPISODE

"Write an interesting story, not a perfect story." — Drew Houston

Drew Houston (@DrewHouston) is co-founder and CEO of Dropbox. Since founding the company in 2007 with Arash Ferdowsi, Drew has led the company's growth from a simple idea to a service used by 500 million people around the world.

Drew received his bachelor's degree in Electrical Engineering and Computer Science from MIT in 2006. After graduating, he turned his frustration with carrying USB drives and emailing files to himself into a demo for what became Dropbox. Today Dropbox is one of the world's leading business collaboration platforms, with 11 million paying subscribers and 1,800 employees across 12 global offices.

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TRANSCRIPT

00:00:00optimal minimum altitude I can run flat out for a half mile before my hands start shaking
00:00:12I'm a cybernetic organism living tissue over metal endoskeleton
00:00:23this episode is brought to you by 99designs where do you need a logo custom website app book cover or anything else 99designs was created to make great design accessible to everyone that's you and to make the process as easy as possible I've used 99designs for years now I've used them for book covers some mock-ups for the 4-Hour Body which went on to become the number one York Times bestseller illustrations of all different types for the multi-volume The Tao of Seneca what you can check out and other graphic design projects for a long time now and I've been very impressed by the quality of their designers and illustrators and you don't have to take my word for it you should check out some of my projects at 99designs.com for Tim I really encourage you to take a look because you will be impressed 99designs.com forward slash Tim fights has free Lanes experts in more than 90 design categories in their platform let you work directly with one designer that you choose if you like their stuff which is what I did for the top Seneca or you can get Concepts from multiple designers and then
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00:02:03this episode is brought to you by wordpress.com I love WordPress I have used it for so many years it's my go-to platform for blogging and creating websites I use wordpress.com for everything every day for my site to not block is built on it the websites for my books include tools of Titans tribe of mentors all in wordpress.com and the founder of my close friends has appeared on the show many times to search Matt mullenweg tequila Ferris for quite an exciting time whether you're looking to create a personal blog Business site or both you can make a really big impact right out of the box when you build on wordpress.com and you'll be in good company it's used by the New York or Jay Z Beyonce 538 TechCrunch Ted CNN time just to name a handful and one of my friends at Google shall remain nameless has told me that we're press.com offers the best out-of-the-box SEO
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00:04:03brand new website check it out
00:04:09hello boys and girls this is Tim Ferriss and welcome to another episode of the Tim Ferriss show where it is my job to deconstruct world-class performers people who are exceptionally good at what they do to tease out the routines habits favorite books and so on that you can hopefully test and apply to your own lives and my guess today is none other than true Houston Houston at Drew Houston on Twitter and Ellsworth he's the co-founder and CEO of Dropbox since starting the company in 2007 with a rush for Dosey Drew is the company's growth from a simple idea to a service used by 500 million people around the world let that number sink in Jersey if his bachelor's degree in electrical engineering and computer science from MIT in 2006 that place after graduating he turned his frustration with caring USB drives an e-mail files to himself into a demo for what then became Dropbox Dropbox business class with 11 million paying subscribers and 18 + employees
00:05:08August 12th Global offices Drew welcome to the show thank you you know I wanted to have an excuse to ask you for your life story in all these details because we've known each other quite a while but it's super weird to sit down with a glass of wine at dinner table or something like that and just start asking you for your doctor evil story so this is this is a fun opportunity for me to take me to start with the backstory that I do not know that is your childhood and you can just Begin by telling us how you describe yourself as a kid and let's just call it going to 3.6 grade or anytime really what type of kid were you
00:06:05first I was
00:06:08exactly that kid who is on computers so we my parents I remembered just like like totally into my living room and seeing is glowing orb and all these buttons in those are two things I really likes when I was 3 I guess still do so for sure I was I was super interested in computers and technology and started out by playing computer or video games basically that was like the first interest and then I wanted to make my own computer games I thought that my career was going to be starting a computer game company and I thought that was that there would be nothing better than that and I was like it outside I learn programming at an early age
00:07:00I grew up in just outside of Boston so I grew up in New England and then on my way to MIT really likes math science so kind of Central casting in terms of being a computer science student then I got my first career was babysitting but then I discovered that you could be paid to program and then that caused a bit of a career shift which we can talk about as much as I enjoyed the babysitting lifesite Rebox an hour or eat some Pringles watch some HBO it's not that bad but the program is even better anyway
00:07:46so what button in middle school and high school I ended up getting a bunch of programming internships or or or summer jobs at what were star-batt startups basically one of them was remote almost over local but then that got me on a path of upstarting companies and ending involved in startups but it was probably the two biggest when it comes to drop box and everything that kind of followed after 4 for my child who is a happy childhood lots of
00:08:22still pretty balanced but I did like programming and Engineering was for sure my first my first love and extroverted kid played Sports kind of kept yourself at recess what was what what does somebody looking in from the outside. How would your 3rd grade teacher describe you and that capacity reclusive I had a really great group of friends and I wasn't counting the soccer team either I think I did I did academic Academic Decathlon which is fascinating thing that it exists but you know more of a mess than an athlete
00:09:15I thought I was I was not like a super social but I had a good group of friends and and then for sure is I went in the college I became a lot more social and just curious about humans and human behavior but but otherwise I think people would like I would have been known in class as always doing it earlier that I think they're like they're super lives in your box I think I was like most likely to start a company near yeah this is I was doing homework for this week I always enjoy doing when it's it's someone because I'm an Explorer bit so I came across this line
00:10:08the described folding chair on top of fraternity at MIT and that you would go up there with piles of books and read these books so I could you play sus when that was in your undergrad career ends how you chose the books of why you did that
00:10:27yeah so I was about my junior year of undergrad I took a leave of absence because I had an idea for a startup that I wanted to pursue this I took a year off to do that what I noticed was that the this was back in 2004 so the movie 21 and the SAT was changing IRS I start an online SAT prep company and maybe because what the opportunity was the SAT was changing in 2004 or 2005 from 1600 points to 2400 points so suddenly all the course material overnight was going to be Obsolete and so I saw an opportunity to maybe develop not just a course for the new SAT but an online course and I teamed up with a former teacher for my high school who had his own little cottage SAT prep company out of my cave we come together we can put the thing online and will be on an even playing field because you know all those 100 page books that have been printed about it are now Obsolete and
00:11:27who really wants to go to some classroom at 8 in the morning on Saturday anyway like we can build a much better experience if we do it online so I was really excited about starting a company and we jumped into it and I think we we met in a Chili's in like we're planning world domination and like figuring out how do you incorporate a company in does really great introduction to the world of starting companies and then it was also the more I learned about mechanics of starting company in the more I realize I didn't know about business and I knew a lot about an engineering programming and then I worked at startups but when it came to one of those kind of there was a frog
00:12:22Beyond just going to product and so is it going to need I know like sales and marketing and and strategy like these are all things and all I know is I don't know a lot about them so I had to hide the scientific method of I just was like I was going to go on Amazon type in sales by the top three or four books and just do that for every like category book recommendations from one of the founders I want to companies where I work as well but it was great company gave me motivation to really learn stuff because I think a lot of times when you're reading it can just be like entertainment read the book knowledge or actually starting a company then you really have an excuse to internalize really study the material so it's a big difference
00:13:22okay here's all the stuff that I don't know and
00:13:28and then reading some me a good way to get me introduced to all these topics and all of that may be the first instance of that was when
00:13:38went through my high school and I was there a lot of great books that you read as part of your high school curriculum but then I stumbled across the book emotional intelligence by Daniel goleman
00:13:52and I was like oh my God likes this is just like spit that means nonfiction but it it's it spelled out something that was I just didn't know you could kind of break down in a logical way and suddenly I have is understanding about the world that I didn't have before and so that was important because it serves it was one of the bunch of early examples that anything is trainable and in and it got me a pasta developing what we now call a growth mindset and realizing it's possible to learn about these things that you do or where you have no experience or where it's easy to be like oh I don't know about that around I'm just to the engineer I'm not a business person and kind of shatter that misconception do you think that's
00:14:42you were open to all these different categories of learning because of the necessity of you starting the company the reason I asked that is that it's it's not across the board but on some people with engineering chops have seem to have learned or intrinsic disdain for sales marketing is different bits and pieces of businesses that are a little softer let's say let's quantifiable in some respects was it was it simply the motivation in buildings company we had to write a rather wear all those hats that going to drove you into these different categories or were you in trinsic Lee using that word quite a bit but interested in learning more about these different buckets through these different books
00:15:28I think it's certainly starting the company made it a necessity and created a lot a lot of additional motivation but the experience of I also found these other topics just as interesting as as the engineering and I think it's an engineer's start off by being dismissive or defensive about the technology is all that matters or if it doesn't have a triple and a girl in Greek letters it doesn't count and I think it's just crazy huge blind spot for people post because it makes the most effective but it's also I'd like the stuff is it is actually really interesting and at that I got having experiences like that and it was just one example by took a class on negotiation
00:16:17and a mighty which sort of open my eyes a notch further on this kind of thing where I'm like a negotiation I go to that class I don't know a lot about it I'm like literally yells louder lies more smack the table harder I guess that's what makes you a good negotiator and then this class like I mean those those are tactics but like the classes has these Frameworks to wear like a pig's more people thought about this and they broke me down and you and it turns out that there's a whole process of I'm covering Mutual interests and figuring out what your Leverage is near best alternate spelling it out in a way where I was like actually this is a lot more straightforward than some of the theoretical math classes I'm I'm I have to take and it's a lot more applicable to my daily life and so I started to I really appreciated like learning a little bit about a lot of different disciplines and in just
00:17:17bring up the folding chair on my roof was the first thing that came to mind as far as how I can actually do that were there any other books besides emotional intelligence during that. That really had an impact on you yes I did not negotiate some classes but call getting to yes which is about principal negotiation and I still think about a lot of those while I still think about and apply a lot of those Concepts today and that's the sad part of it was just like kind of doing a random walk on Amazon but I also became friends with the founders of the companies where I worked and I went it during lunch breaks or another time bye. Go like chasing down and Bug them and ask him questions about like how do you start a company like the only book recommendations making that I taking advantage of being the bright-eyed bushy-tailed intern and shaking down my boss or my mentor my the Sounder or my meds
00:18:17best fruit for a nice and so two of the books that we're really instrumental the first one is innovator's dilemma by Clay Christensen it's a book about how businesses get disrupted and and want to be a lot of those teams are why startups can succeed and Thrive even when they were big competitors who you would think we're just wipe them out and so how that Cycle Works and is about crossing the chasm is another classic marketing technology marketing asking how to how do you how do technology products make their way from early adopters to the mainstream
00:18:53and if you find yourself revisiting those books or were they appointed time during that rooftop Amazon education. I meant to say I say that there are a lot of you read a lot of books not all of them are as good as the innovator's Dilemma but then yeah it also helps to revisit some of the classics are good examples so so yeah I do again
00:19:234021 and you never had a real job
00:19:26you know you're reading this book and you sort of get a general sense for things but do you know you don't really deeply understand the concepts and then coming back five years later 10 years later you can really absorb a lot more than material so I do I sign out of books in general and then when I'm reading a book while triaging like a case of something I need to study is it something that's like interesting or is it at that I might even know something about or is it just fun and if you study it if I'm like I need to study this book then I approach a pretty differently than if it's just like entertainment and for those people who haven't read getting to yes when you were leading into that with some of the concepts from the class I thought to myself I bet that was part of the class or one of the books you read Because you see you had best alternative and there's a charm I do recommend also people vs battle best alternative to negotiate
00:20:26important concept to grasp and there's another book that I'm ever going to people I think it was written later by one of the coop called getting past no go together really really nicely if you were teaching books for a little bit if you were teaching
00:20:49freshman class or senior class undergrad to let's just say smart but non-technical people and you were a signing books to read and they can be part of the class or things could be read in advance if you were to pick I'm just pointing this out of thin air but three to five books that would be to the core of your reading list do any come to mind that we haven't talked about the subject of the class for starting a company
00:21:30and or evolving from being an engineer to being a business person I have a few but I got a handful of of books that I really love and Concepts I still that I use and think about every day so I find my two favorites are high output management by Andy Grove with Andy Grove was the CEO of Intel which was kind of the Google of its time back in the to go back in the 80s and early 90s so he is Andy was an engineer when the founding engineers and then Rosa rancid and tell him became CEO so he he slid his past and and when I read about that or I heard about this book has the best book on management ever written and I agree and it just breaks down all the
00:22:22mechanic service
00:22:25okay how do you run a team how do you break down a goal into into subgoals how do you just sits at 101 at of of running a team in and running an organization and a focus on output and results in how do you measure people in just a lot a lot of things that you nuts and bolts things that you challenges that you encounter when you're when you're running a team on whether that's a company or a team within a company effective executive which does a great by Peter Drucker and Central
00:22:57core that book is really bad people it's very easy to mistake effort for Effectiveness there a lot different phrases for this like to confuse motion for progress or what but it's really about that idea so how do you how do you know if you're being effective what practices practices that you can adopt that
00:23:23that make you more effective and then how do you avoid the sand traps of things that feel productive barn but aren't actually and how do you Dice X unpack the case where we all have the same number of hours in a day but some of us seem to accomplish a lot more than others the why is that and what can you do instead so the effective executive is it covers a lot of ground that that's not that those two I think of his kind of textbooks like you want to study them you want to take notes you want to really chew on Imperial I think about starting a company at some more of the favorite book that's more about the experience of running a company is Ben Horowitz this book hard thing about hard things which is kind of shows you what kind of a mess and Adventure on the crazy highs and lows of of
00:24:14what the human experiences and actually having to do this and then I probably do not and get a little more philosophical so couple favorite books are poor Charlie's almanack by Charlie Munger so Charlie Munger is Warren Buffett's long time business partner and one of this book is really interesting because want one of the things about being a CEO or taking on big responsibility for anything is you have to make a lot of decisions about a lot of different things and do it quickly and be right and so how do you be right about tons of different things but you don't have a lot of life experience like how you trained up that skill quickly I mean that's really called wisdom or judgment and so the rest is a growing wisdom aggro judgement quickly I'm poor Charlie's almanack music is a great example of books so it talks about how I'm actually a lot of what you need to know
00:25:13to be successful in life conceptually you learn it in middle school and high school you just don't apply it or you don't really internalized Concepts and she argues that a lot of really wise and Effective People
00:25:30developer basically build a catalog of mental models wear and Concepts weather that's something from and basically assemble all the best ideas and then figure out how do you apply them in life and so for example of the concept of liking and leverage that that might be a concept that can be applied in all kinds of different situations or comparative advantage economics or know where you need to go you can go on about that these different but then figuring out how do you internalize I'm so well that you're able to figure out kids disease or what matters in these situations and then and then how you avoid avoid terrible decisions but that really how do you build a nothing to get enough of these because of the latticework how you build enough of a network of these metal models so you know which ones to apply when in that you find yourself most of time to go to make good quick decisions
00:26:30and then I'm also on the philosophical front so Zen and the Art of Motorcycle Maintenance. That's like the only things I can't be fit into an algorithm or or or you know that I don't have to have some kind of like mathematical rigor and the Art of Motorcycle Maintenance is about that like just a question but then you have the whole world can't be boiled down to a formula and they both exist and they are both useful in different cases but they don't tend to get along and so how do you like so so what's up with that and then it's a really great book about developing an appreciation for
00:27:24attributes are developing both your left and right brain you know how to use that analogy I think is really important if you're if you're running a team or growing company because there's a lot of stuff for it's a lot about technique and data and and insert a lot of things like strategy or the engineering are kind of fall into these if this and that kind of reasoning but then a lot of the hard part of the job is right about people and and what motivates people how do you paint a vision of the world that's exciting for people how do you build good relationships how do you develop products with taste those are things that are not going to be where you're not able to reach as much into the city in the more rational in early kind of engineering bag of tricks so I think developing both of those developing besides your brain or developing an appreciation for for both
00:28:24this is really valuable maybe one more principles by by Ray dalio who was I know it's a recent guests I think Scott just really concise and good thoughts for like how do you sort of approach all the porch life so it's a mix of a different kind of things that have like more instructional books like more philosophical books more story in history kind of books that I want to take your class was pretty good number one consider me pre-registered or I want to make a couple of comments on these books because
00:29:10I have very fond of all of these books and stopped outside of a couple of notes because they tie together also really nicely so high output management by Grove was out of print at one point and then became so popular in Silicon Valley that a new edition was printed and the Ford I believe was from Ben Horowitz who wrote the another book that you had mentioned you know that you was at the hard thing about hard things right and Ben Horowitz if Andreessen Horowitz and many other things prior to that said that book and there's course selection bias here since I have a limited data set but the startups that I've been involved with that have done best have could have returned the fund many many many times over almost without exception have all red high output management and have a copy of it in their offices. That's
00:30:09I'm successful CEOs who also have that book but nonetheless the effective executive actually going to leave that one for last support Charlie's almanack is a great book and I want underscore something that you said someone passing or which is really important and I know you know which is the avoiding of making really bad mistakes and one thing that Munger emphasizes a lot in the right hand of Warren Buffett and Warren Buffett I guess the study of staff at the best 60-second mind he's ever met and I'm going to butcher this I'm sure but it's something that I think of a lot because I have some tenancies that are unhelpful in trying to be really smart and come up with clever Solutions and I said revisit this quote somebody could find them the right version but it's Munger who says and it's amazing how successful you can be, if you just consistently avoid being stupid versus trying to
00:31:09outsmart everybody I think a lot about that because it's so true it's like if you just come watch your chips and know you're down side and don't makes you consistently make rational decisions with these lattice word sinistra sticks that you mention super super helpful and the effective executive back to you for a second and you mention nuts and bolts the effective executive I've read probably 10 or 12 times I love this book and it's it's very short to it's easy to read and you mentioned that some nuts and bolts so I'm going to use this at and then will probably jump around you if I'm remembering correctly have a label in your email called OPP could you explain four people
00:32:05what this means
00:32:07yes so orig I think originally well it was good for other people's problems
00:32:16although I have made it a little nicer later other people's priorities and because I have a vendetta against email which we can we can we can dig into but I have this experience experience like I'm going to deal with this thing plow through hundreds of emails and your reward is more emails okay keep saying I'm like waiting then what are these things like what am I doing and then you realized it like you're just basically checking off items on other people's to do list where there's there's in the abstract there's nothing wrong with that and supporting to be helpful and we all
00:33:09or have been helped by and help other people but you can end up in a situation where you're basically your to-do list is a composite of other people's to do in your calendar and your email can I send reflects and and tying it says another one of the most important concept as Focus everybody understands like a focus here but there are so many forces it was something people love the idea focus and and when it was interesting just go back to Warren Buffett and Bill Gates citizen interview documentary which is great but anyway they say is the interview was interviewing both Warren and Bill and is like most successful
00:34:09set focus and so if we all in this life seems so obvious we don't know why Focus is going to be told by Focus is important but then one of the things that the effective executive highlights is there so many like a default for anything is to unfocus you and that's true of your inbox or inbox is not prioritize it just kind of like you busy all this request that are other people's priorities if you're working within an organization pretty much everybody will be pulling on you too kind of feed the beast of the organization and soak beans very hard to do a few things well and so am is a lot of great things about that book but I do have an opp folder which I try to keep more find ways to be helpful
00:35:09I'm can help me respond to it to to those those kinds of requests soon as the opp folder it's not this is not necessarily a black hole it's not an indefinite archive necessarily but it's when I'll get around to do you have a set schedule for looking in the opp folder having other people do that for you and I'm in and one of the criteria is it that anything that doesn't come from say a direct report or an investor or a family member goes into OPP or what are the guidelines call even when I'm when I help so I'm not great at responding to these things so it might be if it's not a priority then I'll try to respond
00:35:56and days but sometime this week sometime this month sometimes sometimes I'll give you a good response that's like you still need this but I think it's as if it is something from a personal relationship with the other factors but I know and where I where I personally would be really helpful and they have done their homework and it's like a first pass filters like that I'd say there is no commandment from God that you have to respond to every email you receive so that if it's like a cold email if it's like some some some but I don't know where it's like a sales thing or whatever I just said then it just goes into black hole or if it's something like that you know there's a lot of
00:36:56structurally hey I need it I need a mentor or how do I raise money or you can tell by the question I guess the person many if not most the request will be something where the person to do a little bit of homework and get a good answer and that's troubling because first you try to help people with those kind of things you like to do this thing and then you don't hear back from them and it turns out they just never followed up or just didn't do it and so have to get burned by spending a lot of time trying to be helpful to people who don't do their homework who don't help themselves you realize that's like not how you want to spend your life so you have to keep keep that budget of your time constrained to something small or at least of a smaller bed you should at least be mindful of it a lot of people just and find themselves hopelessly busy and on
00:37:56treadmill responding to other people's things on your to-do list right thing you said about people doing their homework reminded me of this quote from Maria Popova who writes brain pickings which is a some credible site millions and millions of readers and really long form smart writing and at some time I think she changed it to be a little bit more I may be sunny seeming but she had a quote I'm pretty sure on her Facebook page as the graphic as the header at one point it said if you haven't done or if someone hasn't done the homework to determine whether it's a fit or not it doesn't warrant the energy to explain why doesn't fit or something like that which I think is a great Commandments at work for guideline to use because so much of it when you reinforce that type of behavior
00:38:56will they just come back people tend to come back with equally nebulous or on vol 3 questions do you have any other best practices or dues are due not when it comes to to manage an email
00:39:10for not using you know I try not to use a lot of email because off and if it's is good for quick discreet tasks where you're pulling someone out by not doing them but if you're trying to think it's also useful to be like for broadcast like if you have something if you have some long form written direction that you want to give a group of people then then it then that's good use of it but often when people get in these long email threads it's often time it says it's fine and indulgent to get into these big like a flame Wars the best way to talk to them in person and if you getting a lot of little request it's better to dispatch him up and have some kind of weekly Cadence where you can deal with a lot of quick request without having the overhead of
00:40:10email and I think these are all kind of example of a lot of different forces that can take away the kind of shatter your attention or take your time I think one of the most valuable Concepts from the effective executive is is measuring your time and understanding where your time goes and it is kind of shocking and hilarious but really tragic that we all think we know exactly where our time goes but then when you measure it you're not usually just like slightly wrong you're like totally upside down so this is a really valuable exercise for anyone but remember the first time I did this house like I probably what would I find my time on
00:41:10an accident that the inventory like I was feeling like no time on those things I was spending other was a lot of money to sit like following up on favors or speaking engagements that they really do anything for the company in but it just might you what you find is you write on your priorities and you look at your time and you find the things that really Miss Matched and so any mechanism you can
00:41:44to the first understand where your time goes and then make sure your priorities actually match it and then at the end of the day it's actually what you want to do and then just understand that you're going to tend it and then they also want to offset the tendency for to be in this permanent reactive State whether that's cuz you're getting emails that are other people's request or your calendar says one thing usually when you your stupid ass gets too long you just try to you too sore to do things randomly or just do whatever the last thing you just respond to whatever showed up most recently in her inbox or what blank that you or what yelled at you loudest in the last you know our and that's not a snot effective compare to having sending your own priorities and measuring yourself against them and separate topic but I think technology needs to do a lot better job of helping us do that because it's really hard and then
00:42:44is your organization the fires will get done with first and that's that's not a bad thing or that that's like necessary you can't not put out the fire within the important stuff I'd say Eisenhower had this work vs. The Matrix there an urgent that you just eliminating stuff is not important not urgent but but really the biggest priority crisis of prioritization is like how do you make sure that you do that you out a lot time the important not urgent stuff because important energy stuff will get taken care of
00:43:26but then you end up with a lot of stuff that's not important at Aurora Urgent not important or not important I origin and you really want Olympic cut those down as much as possible because otherwise allow the fire is if you actually a root cause analysis is why was the fire in the first place we kind of climate ladder a couple of runs like why did this happen why this happened or why is having cuz that why did that happen cuz of that you find that just a little bit of planning would have would have eliminated the need to find that fire and so he put it in a really easy to spend your days kind of doing the equivalent of paying paying down a lot of like high interest credit card debt with your time by just doing siding all these fires and not actually putting them out at the route so something I do on that front now is this concept called no meeting Wednesday which I think is popular around the valley I may be original Facebook I'm not sure but we certainly half-heartedly adopted that and I half heartedly about that for a while
00:44:26I remember there is a slight I really want to do this cuz there's all this planning and like all these things that are important that they were the cost of me not creating Clarity for my team is super high and I sat down with my assistant at the time and I was like hey I need like a please don't schedule stuff on Wednesday like it's really important that I work on this particular project and you know it's just not going to get done unless there's some almost have like a full day or like many hours of them and rip the time and she's like but she's like what blah blah blah has this and it's important and Blah Blah's this and it's important in blood why's this is important and I'm like there will never be a day where there isn't something quote important and so it's dawned on me and this is all important like is it the but it's not and and so
00:45:21I was like look just I really want it if it is important just scheduled on Saturday I'll come in the office I'll do all those things and then miraculously those things kind of ended up doing themselves and adopting no meeting Wednesday was really transformative in terms of of actually being able to think and make progress on the most important things otherwise you just you lift up your head and you find my 6 months to pass on some important important priority of yours and there's been no progress so think about how do you develop systems and how do you build in time for reflection in an elbow at the time for for you to think and set Direction I think it says probably want this one the biggest mistakes that people make him one of the concepts from effective executive is like a lot of that stuff
00:46:09only makes proud that doesn't does that stuff doesn't make progress with a half-hour slot in a meeting of 10 10 hours of half hour meetings like you there's a minimum Quantum of time for deep side or the work that you need and so effective executive about your time and Effectiveness and in disambiguation busyness from Effectiveness and then the concept of Leverage and I open Management in a focus on output so those those 2 books have pretty much cuz actually everything you need but then implementing it in practice is a lot harder yeah we're going to talk about the practice at all. The first is the Eisenhower Matrix I think I might be referred to as which would you can look up on their own time but the the correlating
00:47:09some respects to be exercise that I think Drucker brings up in the effective executive is the jar or mason jar and if people can visualize a straight if you have a mason jar and next to the Mason jar you have a handful of large rocks that can fit into the jar then you have a bunch of smaller Pebbles and then you have a pile of sand all of which is come out of the jar if you put in the big rocks first your most critical tasks which may or may not be urgent then you can fit in the Pebbles and then you can fit in the sand and you scroll the top and it's nice and neat but if you put in the sand first the whole thing falls apart you cannot take the same volume of rocks and Pebbles and sand and get it into the jar and I would you put visually from from your standpoint is very easy to understand and the time audit though as you described as
00:48:09so important for people to do because very often even your calendar is not a good reflection of how you in fact spend your time and if you look at the say self-reporting in dietary studies where their observational when people are going home and then coming back and Reporting every two weeks if you add you ask people to estimate their caloric consumption it's almost always like 30 to 40% off but it's not a small difference and I think the same thing happens with time really really routinely
00:48:44big blocks of time actually you know what I'm going to get any recommendation then I'm going to come back to this name which of course you're very very familiar with but really want to also get a teaser for what you'll read more about the effective executive if there's an essay I might be getting it at the headline slightly off but you'll be able to find it make your schedule manager schedule yet by by Paul Graham legendary PG we're going to come back to is a good place to start but I want to rewind the clock for a second and ask you why did you stop the SAT online prep company
00:49:19so I started the SAT prep coming in 2004 and then I went back to school to finish my undergrad and then
00:49:30a couple things happen so I was still as I did after graduation I start working as an engineer at a network security company and I also Moonlighting on the S on actually at the SAT prep company but I found myself in a situation where is like it was just like harder and harder to make progress on the SAT for a company and I wasn't really sure what was going on because
00:49:56I just felt like it was just it took more and more willpower to like pedal I don't know where or when we're not there just yet but over time it took a lot more willpower to work on it and so I found myself procrastinating with all these like side projects and all this is burn out and say positive things that burn out but sometimes I can steer the positive attention to things that are more worthwhile but then I was worried cuz I'm like oh my God I'm like so unproductive and this like guilt I was raised Catholic so I just Catholic guilt is like not and I'm not working hard enough this company's not successful and I found my thought I died and just like totally not helpful
00:50:56not capable of working hard what's wrong with me but one good news I started working on this like poker bought that started and ended play with real money like I do I got past the security on the poker Client List Gen 6 so I figure out how to make all that work and then watch the time I Frankenstein moment as the thought comes to life and starts playing on real poker tables and so this idea that you can't poker boss was like totally false but I was possessed it was like where you when was the bot was Frankenstein's monster winning Frankenstein was like not to not too smart and gets confused because it has there's some like obscure multiple split pot or something that I just didn't write the code to handle that situation so the thing crashes and fold your Aces and you're like okay awesome this is what a eye looks like
00:51:56it was scaring my family because I was what I was living in Boston but then we have a little Summer Place in New Hampshire and I was like my family like to come up this weekend we're all going to be at the lake am I okay and then I get to the lake and I'm start on packing my trunk and I've had like three monitors and like always computers and I'm like I'm just like a little cottage on the pond is not set up for to be like mission control so putting monitor is on the stove or like what are you doing there cuz I used to be having all these side projects I hope it's not illegal just
00:52:43unfortunately outside product had to stop because of that and like the token Falls unsexy became like went from like kind of borderline to like very illegal to do online poker so that that project ended but so what's that about going to Dubai and so that was a release and then nothing but then it kind of does a sounding story of Dropbox was why I had to use for getting my thumb drive and going on the Chinatown Bus what y'all get to but but before that I would I kept having these problems working with my co-founder because are collaborating with him cuz we didn't have an off at what we bootstrap the company so we didn't raise any money that's in
00:53:43we don't have an office we didn't work out of the same place we had we didn't have servers we have anything so we would just like email stuff back and forth and I had to work on multiple computer so I kept carrying around this thumb drive and having these elaborate scripts that would back up are the SAT prep company coming to all of our files to a server and then eventually I was like alright well I want to go that I graduated from college about 2006 late 2006 a lot of my friends had live in New York
00:54:19can I like you got to come out it's a lot of fun here in those come out for the weekend and I'm I have a dilemma cuz I need to get some stuff done for my company but I also want to go to New York and I'm like maybe if I take the Chinatown Bus or if I ride the bus I can get I can have four and a half hours each elaborate rationalizations we we come up with and sound like a green light to go to New York then I get on the bus and I forgot my sunrise
00:54:53so crack problem like I hate me oh my God I cannot deal with this problem I like I'm so sick of like what is the question for which there there's no question Force that's the right answer I like the physical equivalent of that like taking an envelope putting something in it putting your own name in the to and from putting in the mailbox and getting back this is what we do to like manage our files
00:55:39so I am on the bus I open up the editor and started writing some code in Python that they said it was a seed that sprouted into Dropbox but I totally possessed for that problem because I'm an engineer engineer by up bringing my favorite classes to school other than some of the stuff we talked about was more like to algorithms distributed systems you know and I found myself at a Crossroads I love standardized test as much as any human possibly can I guess but it was as a couple things happen so 1 is I like pause I'm like okay I'm working on this company
00:56:22I'm kind of burning out part of why is because I thought about going to even if all of my dreams come true in like everything we hope for happens with this SAT prep company then I'm like then what then what and I'm like a mighty king of SAT prep help with these things in the end but I'm like that's not what I wanted to do I'm just picturing this kind of like cardboard crown and I'm only if everything goes well I need to do something out and so I ended up with these side projects and then found myself getting totally obsessed with the first the poker Bop attend even more so with Dropbox and so sometimes it's hard that you don't like how you deal with burnout how do you know if you doing right thing like these are really hard questions I mean for me sort of listening sometimes a lot of procrastination is unhealthy but sometimes
00:57:23that little voice is leading you in a much better Direction so I want to search I want to bring this back to the... That I left after Paul Graham we can certainly go in any possible Direction you want to take it but I don't know Paul Graham
00:57:42if you could maybe could describe Paul Graham certainly is close to a demigod as one can probably get among many many Silicon Valley who is Paul Graham what is y combinator and can you describe your first meeting of pogrom
00:58:04yes sir Paul Graham is best known as the is one of the founders of a y combinator so they are witches an incubator for startups they and they were our First Investors and and they all send us in a lot of great companies including me on Airbnb stripe-a-lot on and Paul was before starting my commentator he had written themselves. Com calm and sold it and then he had a lot of really provocative and insightful essays on on startups
00:58:45that attended a big following and he was also one of the Creator's or lease is very early in the conversation around using Bayesian methods using his kind of math to do spam filtering so he's also one of the originals are one of the Architects or at least involved in that community of people who have figure out how to get rid of spam actually how I first heard about him but then he started writing my startups and then ran this experiment that became y combinator but it was actually called the summer Founders program and I was digging through some old emails about it because I knew this was the precursor y combinator I applied with my SAT prep company to that and was rejected but then managed to go into work I'll need a couple years later so so I guess the first virtual meeting of applying to be funded didn't go well the first in-person meeting was probably
00:59:45why didn't why did the virtual meeting go well it was like a college application for the summer time does programmer to be supposedly was like the same thing as y combinator like you got a little bit of money in and I'll come together I'm busy but I can get in and out of super disappointed that I didn't go well and then put a couple years later I want to apply again with Dropbox
01:00:18this is getting out a little bit but
01:00:22I had so I had the idea for Dropbox I'm sorry working on it and I want to do I see because a good friend of mine or four for many reasons but another friend of mine this guy Adam Smith's no relation friends from college in 2006 and had an awesome experience I had like a front-row seat to that and so much fun having another company just in like a much faster trajectory because of icy and I'm kind of like oh my God I want something like that but then I have so I start thinking about applying for IC with Dropbox and one of the good things about coming from college admissions is easier to learn how these admissions process is work and ycee was not really that different a lot of people applying for a few spots and so in addition to getting the scores in the grades and everything when things you can do is try to stand out and do something kind of unique and so I'm like
01:01:22alright well maybe to get and help me get it if I see I'll try to put a video out about how Dropbox works and Y combinator also had there they just started this new this new site called Hacker News which is kind of like Reddit first start of news
01:01:42and I and I'm like what is I mean I thought all day I think he probably does what most of us do which is just hit Refresh on a car sound like maybe I can put a video on Hacker News maybe I can get an emissions here gets all the attention and then go from there so I made an end to the concept from a book that I had read on that roof called guerrilla marketing which is like how do you get attention and you and users for your product if you have no Jay Conrad Levinson Levinson or something like that the attack of pretty video on Hacker News or creating a viral videos
01:02:35and I want to see that was planted by reading guerilla marketing and soda but I made a screencast like a 3-minute demo of how Dropbox Works cuz I wasn't ready to ship the code but I wanted some feedback and I wanted to get an Icee and I video both got me into y c and I got me a co-founder but I didn't know that at the time so I'm coming back to so then what happened with this meeting with Paul so I put the video on hacker Hacker News for multiple days too long time and then I'm like okay this is so far the plan seems to be working and I'm just like keep hitting Refresh on my inbox and then maybe I wonder if Paul has seen it and then hey looks pretty cool you need a co-founder
01:03:29cuz I didn't get the special at the time they didn't like single Founders applying and I didn't have a co-founder yet this is this is before I meant a rush so I was like oh God because the project agree with him the only problem was the application deadline was had already passed I already applied and the interviews were in like 2 weeks
01:03:52yes I need a co-founder in 2 weeks which is hey I know you're not dating anyone but you need to get married by 8 and so a Clarity ensued but but then I was like I flew to San Francisco trying to shake the trees for any co-founder candidates I hadn't thought of it because for one reason or another all of my close friends and people that would have been the the folks that I would have leaned on like the timing wasn't good they didn't want to do it whatever else and so but I found another friend of mine was actually getting managed to get a friend of mine interested on San Francisco but he's like okay I'm interested I don't know but I want to know if she thinks before I make a decision
01:04:39sound like okay great and I'm like it's a Tuesday my flight is it to stay at like 1 p.m. my flight back to Boston leaves at like 10 or 11 so I'm like oh actually wait this is why she has its dinners on Tuesdays maybe drive down to Mountain View and it's like pitch Paul maybe that way
01:05:05so I can get to the car I like flight on 101 and like the plan was like I see I went in the office it was as expected people just chilling. There's some down time and so
01:05:27and so I go like knock on like I go I go to Paul's office and sure enough he's in there in a minute I just want to show you some music Mountain busy
01:05:41and I'm like okay luckily but I'm coming I can almost see your screen I know you're just like every four years Leary Hacker News right now it's not actually busy but it's like awkward so I step outside and I talked to Jessica who wasn't his is partnered at in co-founding YC together and in his wife and I talked to Jessica McCabe look Jessica isn't it I'm really sorry to bother you guys I just have a co-founder who is like looking for some feedback from Paul it to make his co-founder decision and I guess I'll be back in like 4 hours and I swear I'll die won't take more in 60 seconds of Paul's time do you think it's okay if I go in there
01:06:27and she's always a true of course I can no problem like I was not doing anything just like just
01:06:36so I go back in there
01:06:39and it's like
01:06:43detonation it's like I said like 3 words and Paul's like now he's like I'm not going to see your stupid demo the whole reason we the application process is so that Randy was like you and bother us it's like now please look cute and so this is not going to be good I like those ruff-ruff return to San Francisco situation did not work out what I did I did meet with the dean of admissions he just thinks I'm an asshole but it's good training this is like the new normal if you're starting a company
01:07:38let me just hit pause for one second what were you what were you saying to yourself on the way back and was the self talk on the plane ride back I was like I have I could not have like F this up any worse if I had tried
01:08:00if I just like
01:08:02hadn't like
01:08:05maximally pissed off Paul
01:08:09anyway not have no co-founder noyc and probably no company and I like 2 weeks left till like resolve this may or maybe a week left her a lot of time so is that yeah I was like I don't really see how this all kind of lives happily ever after
01:08:32but my account of shaking the trees in San Francisco did help so I met it turned out I think I'll go vote first Club season MIT student he dropped out here he had just dropped out to do Justin TV which became twitch and then Kyle then later started Cruise which did great schism, how has done well and then I was complaining to Kyle and like I like I need a co-founder I do know is there anyone you recommend and he he recommended me to turn down. Kyle and Josh were for me and said he's going into his garage and then a day or two later I got the senior undergrad at MIT computer science student and he was like Hey I.
01:09:32Hacker News and Kyle said you're looking for a co-founder you know maybe we should talk
01:09:39and then it was kind of insane like we met in the student center maybe we got coffee one more time and then he drops out of school he's like a senior he drops time of the semester left two hours and then he need the two of us commit to like spending most of our waking lives together for the foreseeable future I don't think there was really understood that at the time fortunately it all has worked out great but so but Against All Odds by team up I think Paul forgot about his meeting with me or didn't like put the two together so we we did our interview and we were Milling around waiting for you in the morning
01:10:39we go get lunch we come back to the car our car got broken into on our laptops got stolen but fortunately all of her stuff was on Dropbox so we were like patient zero for all this and then we got the happy phone call from from Paul saying hey we want to find you guys and and I don't know why it was it was nuts I don't know if this is changed but for some. Of time I think it's probably still the case but but you could correct me if I'm wrong I mean Dropbox was Far and Away the most successful investment that y combinator had ever made what points did you go to go to Paul's office knock knock hey Paul like in Brackets now we're friends
01:11:39remember he came in Tuesday on a Tuesday not too long ago did you ever bring that up with him or did you learn about it through some other means I like to remind him about it every Cup every year to remember it he's like I was so awful at this app so that the mostly it's just they they both Paul and just go to turn like bright red and they don't like to talk about it which is like it why I like to keep poking at it every now and then it's it's all good he did tell you I was super obnoxious but name of the company it was wow so so just
01:12:31from day one you have the name that stock dropbox.com
01:12:38getting the dub dropbox.com domain name was oh my God that was a that was a journey
01:12:46so there was a crooked people run into this stuff I'm sure I'm sure we can I'm sure we can pull some lessons from him I remember get drop box actually the Behind the Music version of the story behind the name is also probably unintuitive or like not what you'd expect so high school and the answer is like basically he's a huge nerd who likes computer games and that's true one of the things we would do is we all bring our we would like and I would bring our computers to someone's house and we play games
01:13:38and back in the day these things are called Lan parties they are about schools account up and play play till sunrise and and and so on but we bring a bunch of people together in Austin someone doesn't have the the right Maps or the right patch for the right whatever and so we had a convention like you just create a folder called your Dropbox that's Sheridan writable by anyone and that's how we will exchange files so that people can play games and then it's Christmas 2006 I'm trying to come up with the name for Dropbox door didn't have a name then I the initial name I'd like some
01:14:26what the name for I was busy photoshopping a logo is it initial iteration of it was full door anywhere
01:14:34catchy catchy was which was probably the first indication that I had a brilliant future in marketing and after that sound like in Photoshop trying to make a logo for folder anywhere around the course there's a folder or something like totally a name and then I start running my folder anywhere.com was actually available so I was the proud owner of water anywhere that comes and I just searched and I found there's a coming of files anywhere
01:15:13and I was like no like I can't I bet it's like I can't now I can't even fold or anywhere in so I certify ma name talking to one of my friends from high school and I'm like God I don't want to call this thing
01:15:28folder anywhere is taking like maybe I should just maybe I should call Dropbox like from the from high school that are from Land parties and he's like okay whatever and then not available
01:15:50so we just live with get dropbox.com for I tried to you you can sometimes look up who owns a domain and contact them and so I tried actually did I imagine she give the guy a call and I'm a very dropbox.com you not using it and the guy was like for a project
01:16:15I'm like okay cool
01:16:18just February
01:16:20tell him 7 and then then we can we get to track to the whole getting into YC finding a co-founder all that doing what I see and then I Landon to make up move to San Francisco in September
01:16:33and I'm like we really need to get this domain name and unfortunately Russian I totally falling in love with it so I can we weren't really only had one plan by the way that's that's called a great show up at someone's house work so well the first time going to do it again so I lived in Pleasanton and to some extent and I'm like and I call him I'm like how's that project going cuz there's obviously no project and and he's just kind of being difficult and so I'm like I'm like okay God damn it we would get off the phone and I'm like Arash Licious like show up at this guy's house
01:17:30let's just see what happens so jump in another Zipcar we go to the drop to the go to the like the the corner store and get there like most expensive bottle of $20 champagne we could get the car and go to his house
01:17:48and it's like 9 at night so I just kind of shocks kind of the music like let us in we have a sweet we start talking he's like okay look you know we were doing and I would love it if it's true that you're not actually doing anything with the domain you know it will help us understand what you're trying to accomplish just like at least consider this alternative word and we use dropbox.com you know we got some really good folks who are excited about this and involves what s y, door we just got funding from Sequoia our first Venture Capital investor who was one of the best in the world and so relaxing
01:18:48all the time why they should be interested and you hold all your cards that I send nothing happens and that's what we experience over the last 7 months so we're like okay so like at least get to sketch out a case that a reasonable person would look at interested and so and then he's like cool it's interesting I got to talk to a friend and she wanted to touch base soon and I'm going to come like right it's like Friday I'm like what is like a Friday night I think and I might be back on Monday and I'm like holy shit we might actually be able to get this thing like this guy's been impenetrable and so difficult like we're both kind of in and just like this is such a positive thing
01:19:48so we go back on Monday and he's just like yep thought about it not interested thanks bye
01:19:56and we're likely is this for real but you just like totally wouldn't budge and so that was a much sadder drive back so then this guy for a couple years every year and then we launched drop out we put a wee wee on strap-on publicly and then all these confuse people start going to dropbox.com and and presume to start trying to get in there they wanted to get into the Beta so this is this is later in the air so there probably March 2008
01:20:45you were looking to get into the Dropbox beta and then he got here so he he that he kind of goes dark he puts a privacy Shield up on the domain then puts up an AdWords landing page so like dropbox.com like a like a like a Google AdSense for domains page which was a problem because then you're like oh my God now this guy is like totally cashing in like it's basically you go to Dollar Store, it was big is the average for all of our competitors and so I'm just thinking of like I'm like what the hell are we going to do about this like branding exercises that
01:21:36did did not go well I try to find an alternate name so
01:21:42I'm just like how my god look what what are we going to do and the answer was read the federal copyright and trademark and I beat him it was kind of an expert in cyber trademark law an armchair expert in the stuff and it turns out you can't just like get a domain from someone for no reason like you can't be like you're not using it so therefore it's mine anymore you could be like oh you're not using that lands give it to me but it is also illegal for someone to intentionally confuse
01:22:22could use customer can confuse your customer so I can't just like say that you know I can sell paper towel towel or I can't sell like Kleenex with 3 E's to confuse people or whatever problem and we had another hole Odyssey trying to get the Dropbox trademark which that's not as interesting but I might actually have the registered trademark either but he was not making money from infringing are common law trademark rights and so I'm working with this crazy trademark trademark and domain attorney and so we sue him for federal at 4 for trademark infringement and so that got his attention and we would not have done trying to push him around me is really a profit off of confusing or customer so we were for sure. On our high horse after that
01:23:22and I mean that was on a conical a whole experience but okay okay okay all this lawsuit you know I'll give you guys sure I'll sell you guys are dumb and I'm like okay well like we can offer you stock or can I just take cash so we paid him $300 and got the domain live like sending that first email from dropbox.com to Paul and Jessica was a huge Triumph
01:23:54but what's even if we offered him stock
01:24:01at that lake or otherwise I would have been at the scene around the most tourists like multiple hundreds of millions of dollars so that I think
01:24:15what you can take away from the Slick snow manual for the right wing it and there are a lot of things that are at the equivalent in today I'm just going to get in the Zipcar with a bottle of champagne and hoping for the best and and you know sometimes I get really good card sometimes I get really bad cards for you just got a kind of role of that and so between the domain HD 2000 Stephanie those are definitely memorable plants along the journey a bit before serve recording about the psychological aspects of Shay prepping for starting a company and I want to try that to a company you mentioned earlier which is read it and see if you mentioned that Hacker News assertive Reddit for the computer science / hacker subset rent and I remember having Alexis co-founder on this podcast
01:25:15meeting really early on with an executive at Yahoo they're really excited they went in and they share their numbers in the executive said it was so insulting
01:25:32that Alexis took you are around in your I think it was and put it on the wall in the office to motivate right but that's possible right there are there are certainly people who crushed by that it could be the end and I don't remember exactly where this quote is from when this came out and how you what the self-talk was said they look at it there's an article being written about Dropbox and I think the quote was quotes fortunately the Dropbox Founders are too stupid to know everyone's already tried this and quote
01:26:16when did that happen how did you and anyone else involved
01:26:23respond to it
01:26:26yeah so that was very early I would say within the first year and probably the most what happens is you'll get I just thinking back to that first video that I thought it was positive people like I would do something like this it's good and it was really
01:26:50and I was really encouraging so I just saw on the one hand path of peanut gallery saying that the other half of saying like a listing all these reasons why it's been tried before and won't work that in the end even if it does work like Microsoft Google everybody's going to kill us and here's why it's never been a business in here all these other ones I have never seen
01:27:13I was like yeah you're probably right like I don't really see how we survive as they are in 2007 I don't see how we kind of make it threw me out to Mount Doom the two of us so and then invariably every investor we talked to was raised similar concerns so that the feedback is all pretty negative so
01:27:43it's easy to say like I'll just ignore it all but you can't have to be encouraging feedback and it sounds great you know and I knew that I needed it and then I wasn't like trying to create a billion dollar company I was trying to just like saw the problem so I think setting your sights slow in the beginning ironically can be helpful because you're not putting so much pressure on yourself I was like look at my shoulder it'll be one of this is just another side project in a number of side projects in like let me not suffocated by it putting all these crazy thing is pretty important even just having a video was a big milestone and lunch with pride of a does a big milestone and their bunch of Milestones but so is it a continuous process more than like I was just one moment in time
01:28:43but yeah there are people who are very good arguments about why this was going to be successful and that's why I think
01:28:52did you have to have alternate empathic skin and things can get that balance right because if you just have just ignore all of the feedback and then you're probably probably going to have some kind of blind spot and you're going to have to go to miss some important information so just because they came but but just because they came to that conclusion doesn't mean that there are some signs were all correct and that's why you also need to have enough sex again to know when to like when to be a little bit dismissive or not listen to everything
01:29:29and part of what helps with that is having convection and conduction that comes from being able to sing from first principles
01:29:37and pay less attention to people's conclusion let the outputs of people's conclusions as much as the inputs into those conclusions so what does that mean what people said that okay I can be successful because of people tried it a million times
01:29:53and that is that is true and anybody who did that sucks actually true it's not you can't debate that but I would have been true for mobile like every phone every mobile thing before the iPhone ready mobile software company of apps like was a total failure before the iPhone World changes suddenly it's the right time and so if you study history of Technology history business he realize what is not in it of itself causal so actually there are a lot of good ideas that are about ideas for a while because the timing is wrong but then the timing comes right because of some discontinuity in Tekken like then end
01:30:36books like the innovator's dilemma and others will illustrate that and so if you really understand these if you understand what is 54 missing the key from that. Just because something has happened before I like has failed before doesn't mean it will always stay on the future can still feel but but that kind of connection came from an understanding or of a beliefs and a friend of worldview and framework of like I hear so here's how I think business works for years how to think about an idea like cars so that said it's not as so I think I receive advice and how do you serve develop first principles thinking which we talked about but that doesn't make it feel any better you're going to stay out person that like you are stupid right here at Super ad hominem right
01:31:36I think you have to have a sense of like this is normal you just don't take it too personal the colonel of that's useful from it but not feel obligated to to accept the whole thing I think more broadly you just have to whether it's getting criticism or just a lot of the thing of I think with one of the harder things about running the company in general was I just remember being in the beginning being like Oh my God like all right now we like Sequoia has decided to invest in her come against the odds now Sequoia has decided to invest their their writing us a check for a million dollars
01:32:22I hope they realize that like I've never I've not ever like really done this before and like a god like that million-dollar it's great to kind of cash that check but home and they're going to be looking for that money back at some point like what are we going to do and so that's not it wasn't a lot of things going on in my head of the time but and then like oh my God how to successfully manage people really you know the idea of a hundred person company is like terrifying like I'm this treadmill just to go faster and faster until like I'm violently thrown off of it like how am I going to deal with that
01:33:03and also sounds like okay well I'll just build a company until it's like successful enough for makes enough money right is not to worry about money anymore and then I decide soon as I get to that I don't know this is like some kind of cereal my car as soon as I get to that level of success I'll just stop and like just I don't screw it up but then interesting ly that that goal post kept moving back and moving back in the movie about the money but you can read in the Y combinator application like us now public are we put that out there I'd like I went there are like I would if I had $1000000 after taxes after 6 months of work I'd consider that a pretty good deal so
01:33:47so people put more on there oh my God this is like I'm I screwed up your instincts will to be to run away from that feeling and what you need to learn to do is run towards it
01:34:08because that's just going to keep keep having to keep having to drive short this guy's house I don't know if I'm able to get arrested I don't know we're going to do it I don't think that's the best example things where it's like you just got to kind of figure it out and keep going and then one of the great things from that that been wrote in his book The hard thing about hard things is the CEO of managing your psychology
01:34:35the time because it's like Ray dalio's book he's like pain plus reflection equals progress people love the progress part are they love grows but they don't love the Pain part and they don't bother do the reflection part so so understanding that isn't in the understanding like depersonalized this is just like in the process of growth it will be painful or think of your journey as more of an adventure rather than like a final exam where you have to get everything right and you only got one shot I think that's this report and then second is all right you have to announce it is gross and pushing yourself but he also have to take care of yourself like it's fine ways to metabolize stress and avoid burnout and
01:35:35for some reason people just say they just to eat use the one to love like pushing themselves harder and then they break and you know you wouldn't do that to your car you wouldn't do that with like a musical instrument so why would you do that to yourself right so I'm just a just a buzzer is playing every time we stayed at the same hotel or been at the same events and I've gone to the gym I've almost always seen you in the gym seems like you have just as component of that a physical practice to care for the machine so to speak but it's really important enough so that you don't break down and so and then you gotta figure out what that is for you and I and I know that something you really care about and and
01:36:35something some kind of routine and stick to it but just a basics of the dumbest advice is like you're not sleeping or wearing like that successful people somehow work like 70 80 hour weeks and that's the norm there number problems with that first as I usually not true. It's usually more of an indication the person's either lack of awareness about where they spend their time or lack of Effectiveness they need it if there are only two on the shed is like work more hours because just think about that like in there. But if your only Advantage is like 20% more hours then he's merely very committed then you're not going to have outside results and you also mean
01:37:32I think this meme that people that successful people work hundred our weeks or something it is both false and super harmful most the most the most successful people I know actually work
01:37:44hey there Crush X where they're super busy but they otherwise have a work week that looks more normal than not and so that that was something I didn't realize when I was when I was starting out, but the basics of sleep eating well self self care exercise putting it on your calendar not just wishful thinking and hoping it'll happen in the spare moments like if you can't see these things on your if you cancel your priorities in your calendar if you can see your gym time on the calendar it doesn't exist so
01:38:18can I think Alexa self-awareness metabolize stress and avoid burnout but I think they're taken care of the basic foundation and setting healthy boundaries is pretty important than having sustainable workload being willing to let it shine a hard on yourself and embracing that so for me it's been super helpful coaching meaning you have like an executive and really they give us a shot at some my friends have had spoken positively about it but it's little it's my first coaching experience 360 and then you sit down you do your review your results so sorry deposit 364
01:39:18no is where you have any Superior is Piers employees set her up when you get all this feedback from all these being everybody were closely work with so it's kind of overwhelming cuz you get a lot of it and it's not all good so yeah and actually to this day like opening those documents and like reading all the 360 two bags one of most painful it's like human experiences you can have but it's not funny it is at least not fun and it's not something I look forward to but it's important so because you need to know like it's much better just like know and they'll do something about it like I've been been been a great friend and mentor and he's like he was reflecting
01:40:16it's a blessing to find out about them
01:40:19sobering first page is usually like your of your strengths and I'm like okay he's like my coach was like you are really get you really really care about people you love building relationships and I'm okay hun that sounds that sounds good you really creative ideas all right I'm enjoying this coaching thing so far that the stuff is like so crazy I'm like
01:41:00and then flips the next page right now like his property opportunities for like you are really conflict avoidant make hard people decisions I hate people don't know what used to be like where they stand okay he's like you're unreliable you drop if you drop off your not paying enough attention to the things that are important than likely okay and he's like and you suck at planning people are confused about what to do and I'm I'm like okay and then he's like look okay you're good with people so and you like people to be happy so you avoid conflict you are creative you like me ideas so you don't you don't pay attention to the routine stuff you're comfortable with chaos so you don't plan
01:41:57like these drinks are all think they're going weaknesses in Disguise like so there's no one who's like 10 out of 10 on everything and that's that's why so it was a lot different philosophies on what you do with a feedback and play more effective executive tenants but other than that I think it's on all kinds of different dimensions valuable and talk about the Enneagram in your book and that's at system but then you read it and it's like reading a personality quiz on the Internet you sure if you remember he had some letters and just like some stuff but you don't actually do anything with it to be similar in terms of its own
01:42:57number for Sally types but it's much more to Siri about what kind of my motivate people want what motivates them and so is very loud like I do it Mighty I was I was super scared to go I was like that sounds like a cold and it kind of is but it's been very helpful both to do individually and with your team is it just you sort of what you learn is like I hear that you're my blind spots in Enneagram 7 these are like totally textbook strengths and weaknesses of a 7 that they like they like new things they like chaos but then they can become distracted and and you know that and I'm reliable conflict you always want to have an accurate map of like what you need to work on
01:43:49how are you how are you introduce to any Graham found her but then I was introduced to it through a guy named Gentry who who is the founder of mailbox who worked with us for awhile to four years ago I was like you're going to love this it's great that sounds super weird he's right side that says been super helpful
01:44:16awesome well I know you don't have a ton of time left and maybe sometime we'll do it I'll follow up with some wine and I'd love to talk to you more about your Cadence and someone with an executive coach maybe we get to it another time but I thought I thought we could wrap up with another thing that you mentioned in the book you know tribe of mentors but I'd love to hear you talk about it which is the tennis ball Circle in the number 30000 SQ tell us where this comes from and what that means 2013
01:44:54and I was like the whole premise for his son like I would it was kind of like I'm 30 I don't really like the promise of the Punta Canta what do I wish I'd known what would I tell my 23 year old self and if I could sort of send a cheat sheet back in time what would it have on it and what I would put on a little cheat sheet is a circle in the number 30000 so the tennis ball is really about finding that thing you can become obsessed with and so Dropbox or you can just of the side projects like the poker by like I am both most productive and happiest and most successful and not overlap something the world needs more value so don't sound alike find something that come from
01:45:54I had this like really lazy fat dog growing up who would but when you showed her food or you showed her tennis ball should be just you just like nuts and so you throw tennis ball for like ham running on Twigs or something like that like that ridiculous expression on your face and still kind of be so obsessed with something that you just don't care about anything else I did not overdo it but the point is I can find something that I just passionate about I like that just like I thought you can become obsessed with and then just really love it something you would do even if you weren't you know it even if your job then the circle
01:46:49concept is really there's a saying about a guy named Jim Rohn that your ear an average of The Five People You spend the most time with and I found out to be super trip so sudden and so then they choose choose wisely so the weather that's the literal five people you spend most time with the environment un so being going to a and so and I think that's been true for me I'm going to MIT really Tommy like what a good engineer looks like super capable but then also you got jealous and you like you know I want to be that good and see that kind of negative energy or so and that's not true either at school or Founders like friendly competition there or with my friends who are starting companies in San Francisco all of those contributed massively to
01:47:49I did to us just making it and then finally 30,000 is is is really about. Everybody lives on average humans live on average for the 30,000 days
01:48:01I was at first I was like okay yes this is like a clinical truth not terribly interesting cuz I think I just moved to San Francisco and as and I was just like I couldn't sleep so I was just like on the internet reading stuff and I've came to the came across that okay and I open the calculator and I'm like alright I'm 24 at the time 24 * 365 * 38000 days now
01:48:28so this idea of like life unfolding infinitely in front of you is actually not really true and so it's really important to not just make everyday count but also understand that like think of life more as an adventure or a story more than how you think about life as when you're graduating college which is like life up until you graduate college is just like a series of checking off boxes am I getting ready for stocks and performing in all of your worldly achievements can be our average into a GPA and so every mistake is like bring that number down in like it's something you have to like obsessed over and then college graduation the first day where that sound like you anymore you don't really have a GPA anymore you're not an average of all your successes and failures like you should change your mindset to life and also to think of it more so just making a story that's interesting not just not trying to be perfect because I think it's a trap that allow people fall into so
01:49:28what about if you were to play everything over again a hundred times who knows what would happen but if I could just hand back a cheat sheet that's what I would put on it that's how you put on a tennis ball Circle in the number 30000 Time ahead of you and I'm sure today is no exception so to let you get back to your day but Tiffany
01:49:56losing comments asks suggestions or anything else for people who are listen to this party comments before wrap up
01:50:08I would say so
01:50:13I think I just don't don't forget to have like don't forget to have fun in like I said I think it's the end of you want to have like that there's no session was avoiding failure and if you think of it more as aren't really that important it's more how you respond and even what you want to do is write an interesting story not like a perfect story
01:50:38yes yes and I mean that the first thing they do with I shouldn't say the so definitively but it's like a lot of screenwriters or experienced will the bull say you have to create characters
01:50:51the birth of the protagonist who on some level the audience really cares about and then torture them and then they come out the other side as well screenplay and you're part of the human condition it seems like that is going to be a component thank you so much for the time I always enjoy chatting hopefully we get to hang in person sometime soon but I appreciate you carving out as much time as he did to to share your stories to everybody for sure thanks a lot of fun and for everybody listening we will have links to all the books mentioned everything else that that the Drew may send our way as well which of the resources all the things that we discussed Hacker News Etc in the show us what you can find as always at 10. Blood for such podcast with all the other episodes and until next time thank you for listening
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