Caterina Fake — The Outsider Who Built Giants (#360)

Optimal minimum temperature at this altitude.

I can run flat out for a half mile before my hands start shaking.

I'm a cybernetic organism living tissue over metal endoskeleton.

This episode of the Tim Ferriss show has brought you buy athletic greens.

I got us all the time.

If I could only take one supplement.

What would it be? The answer is inevitably athletic greens.

I view it as a lot of you now if you would as all in one nutritional insurance, I recommended it way back in 2010 in the 4-Hour Body and I did not get paid to do.

So, I've been using it since before that they use in a lot of ways I travel with it to avoid getting sick or to help mitigate the likelihood of getting sick.

I take it in the morning to ensure Optimal Performance and overall.

It covers my basis.

If I can't get what I need from Whole Food meals throughout the rest of the day and if you want to give athletic greens to try and they're offering a free 20-count travel pack for first time users.

I nearly always travel with at least three or four of these when does bad in other words if you buy athletic greens as a first time buyer you now get for a limited time and extra $79 in free product.

So check out the details at athletic greens.

Com.

Tim again, that's athletic greens.

Com Tim for your free travel pack with any purchase.

This episode of the Tim Ferriss show is brought to you by Uber which I use pretty much every day over makes getting around town and the world for that matter easier than ever before and now Uber is introducing Uber rewards a new Rewards program that helps keep Modern Life going so he knows already but I've used Uber thousands upon thousands of times since 2008 or 2009 when I first became an advisor and it was even just a prototype stage.

I've since you used it to save my skin in many countries where I don't even speak the language to help transport my dog around to save on delivery fees from Big Box retailers.

The list is really countless for the number and types of ways that I've made my life easier with the Uber as a company Uber has been doing a ton of really interesting great things in the past year Awards is going to make you love over even more.

It's a brilliant idea and you can earn points on rides and Uber Eats to earn points whether you're staying in Or going out and the more you use it the more you get and you unlock rewards such as Uber cash, which you can apply to rides or food orders.

There's a lot more than you unlock all sorts of new benefits of each membership level such as flexible cancellations with gold.

This means you get your cancellation fees refunded when you rebook within 15 minutes for a limited number of uses you get price protection with Platinum.

This means you get price protection on Uber acts between your two favorite places.

So you choose the two places you right between the most and drink busy hours when prices might be higher you'll be protected above a certain amount in either direction.

You might get complimentary surprise upgrades with diamond for instance.

This means that at no extra cost you request Uber X and you get upgraded to premium rights like black and there's a lot more priority support pretty pick up at airports getting access to highly rated drivers all the different levels and it goes on and on and on switch.

Check it out.

Com.

Examples the more you ride the more you eat the more you get so for the terms and to learn more about all the ways.

You can earn Uber rewards go to uber.

com rewards.

That's uber.

com rewards check out the program terms.

The details examples at uber.

com rewards chances.

Are you're already using Uber so you might as well often do this and get more out of it.

And if you're not these are all the more reason to install download and try it today.

Hello boys and girls, this is Tim Ferriss and welcome to another episode of the Tim Ferriss show where it is my job to interview an attempt to deconstruct world-class performers from all different fields ranging from business to military chest Sports everything in between.

And today.

My guest is Caterina fake at Katerina.

That's like it catering minus the G+ an a at Katerina on Twitter Caterina fake is a long time Silicon Valley Pioneer.

She's the co-founder of yes VCA precede and Seed stage fund investing and ideas that elevate our Collective humanity and we'll talk about what that means previously.

She worked at founder Collective is a Founder partner served as chair of etsy and was the co-founder of Flicker at flicker Katerina and her team introduced many of the Innovations news feeds hashtags followers likes and so on that have become commonplace online Katerina went on to found several more startups find Rihanna and become an active investor Advisory Board member helping to build companies like Etsy.

Kickstarter from their very Beginnings other Investments include Cloudera stack Overflow and Blue Bottle Coffee among many others.

Katarina is an early creator of online communities and a longtime advocate for the responsibility of entrepreneurs to the outcomes of their Technologies Katerina sits on the board of public goods the Sundance Institute in mcsweeney's.

She was given the Silicon Valley Visionary award in 2018 and has received two honorary doctorates one from the new school and the other from RISD.

She's also the host of the brand new podcast should this exists which asks the question what is technology doing to our Humanity should this exists can be found on Apple podcast wherever podcasts are found or at should this exists.

Com Katerina? Welcome to the show west it as a guest on the show and I am really so thrilled to finally have a chance to spend some time together because I feel like it's been many many years in the making.

And if I remember correctly when you first moved out to San Francisco and you and I had some kind of conversation or email exchange very early on so I was so impressed with at one point one of your responses because I asked if you would I think be a panelist or speaker set some conference might have been South by Southwest could have been another and you said I'm taking a year break from conferences and I was so impressed by the categorical decision to not do any speaking engagements that I made a mental note of that and there's so many places we can start but in the process of doing homework for this I found mention that I wanted to do a fact check on this of you having plane tickets automatically canceled and other issues related to your last name is that is that accurate did did those things actually happen? This is happened to me many times in fact And I discovered that it was actually the systems at KLM and Northwest that would throw my ticket out my last name being fake and I have missed flights and have spent way too many hours with customer service trying to fix this problem that I was unable for the first two years of Facebook to make an account there also and and probably all of my relatives do you use a workaround now to prevent these types of problems or is as it has just been resolved at this point.

It has been resolved by my not taking those Airlines.

Actually, you will see a flight, you know on KLM Northwest and will not take it.

I'm not even sure if these are lines are around anymore.

I think I'm not up to speed on the airlines.

Magazines in Airlines which go out of business faster, but despite these travel challenges you somehow managed to land in Silicon Valley and you're chatting before we started recording about your I think the term was stochastic path and the collect a background that you have but could you describe four people how you ended up in Silicon Valley.

Did you do Stanford MBA and study computer science before that and and it was it was the The Objective all along.

How did it how did it come to be? That's actually not my path Stanford MBA.

However, what happened was I was living in New York and had spent the summer in Arkansas rock climbing and was big into rock climbing and had Hooked up with a group of people there and we are on our way to Nepal to do a big climb.

And so I showed up at my sister's apartment in San Francisco.

She had moved their first time from the East Coast originally and I had my my ice pick in my crampons on my backpack full of deer and was planning on doing a big climb in the Himalayas.

So she being my older sister put me up for a couple weeks in her house and there was visiting her on the way out to Asia.

But what happened was my trip was delayed because I'm one of our one of our kind of had climbers had had become injured and then the trip was delayed and delayed and then finally it was Avalanche season.

It was no longer possible for us to do the to do the Trek through the Himalayas.

And so I ended up staying in my sister spare bedroom.

At the time San Francisco was cheap enough that people had spare bedrooms.

And so I just stayed and my delightful sister who I love dearly and S has always taken care of me throughout my life her little sister shows up and you know, six months into my stay there Katerina, you might want to think about getting a job.

So just being 1994 the most interesting thing that was going on at the time in San Francisco was the internet and so I got started then as a web designer.

And did you have a design background at the what's flashback six months? So you're landing in San Francisco on route to this climbing Expedition at that point in time.

What did you think you were going to do when you grew up? So to speak or over the that the following 5 to 10 years.

Did you have do you have an idea of where you thought you were going it prior to the internet entrant entering the picture around is in art and literature mostly and from the age of I would say probably about 10 or 11.

I had decided that I was going to be an artist and a writer and I had studied I actually gone there was an art school dropout.

I graduated from Vassar with a degree in English literature and I had to apply to grad school at Berkeley before this whole internet thing happened and was planning on getting a PhD in Renaissance literature.

That was really my true love.

I've always loved poetry and The internet which I've always had an interest in and had had a computer and had been hacking around with it since I was young was another alternate path that I took so I had actually, you know, I'd had been very interested in head.

There are a bunch of professors that I went and interviewed with it at Berkeley Renaissance literature was my great love Do you think that your background which is in some respects very I suppose a typical for someone who ends up in Tech did you feel that say literature has provided you with with some type of advantage or contacts or perspective or other aspects of your background that ended up really assisting you with the with operating in the tech World in investing in Tech world.

Do you feel like those things have been in any way in advantage? I really think that people come from outside of the industry have a superpower that people who have lived within the industry.

Their whole lives were have spent all of their time in that.

Mindset it just give you a superpower does give you an ability outside of to be able to see things in a different way.

And if you look at all of the companies that I've been involved with and the Investments that I've made they are companies that emphasize creativity communication connection collaboration and community and and a lot of that comes from this background in Humanities that I that I have.

I really am a big believer in people's creativity flourishing when they come at things from a different direction and see things in a different way.

And in many ways, I've always encouraged entrepreneurs and investors and people who are interested in entering technology to come at it from a different field and really emphasize those parts of themselves that are different from the mainstream expectation of who you're supposed to be and what you're supposed to Oh where you're supposed to go to school coming from a different direction is almost always an advantage coming from corrupted climbing Expedition as you did six months or so after letting in San Francisco, then being encouraged.

Sounds like very gently and understand understandingly by your sister to to go to consider getting a job What did the what did the subsequent 12 months or so look like for you when you when you stepped into that world? This was a very early stage in the internet and there were no manuals or guides our blog posts or anything like that to help you shape your approach to do the industry.

And so you had to make it up yourself.

It was a very small community of people that were interested in the web at that time.

They were all centered down in South Park which we at that time called multimedia Gulch which is kind of a funny terminology.

It was very early stages.

And so I had to teach myself HTML I had to figure out how to design for the internet and it was a very experimental DIY self education at the time getting getting involved in that at that very early stage was just so it was such a small community that I just happened to be really lucky that my friend.

My friend's roommate actually worked at one of the very first web companies and was able to teach me HTML and where did where did and when did flicker enter the scene where the the embryonic stages of Slicker? When did that come onto the radar? Well that happened.

It's interesting because we were actually in the process of building something different when flicker came about we everybody calls it pivoting these days but it was it was a pivot and came out of it and unsuccessful game.

It was also built during the lull after the.

com boom.

There was the.

com bust in mm.

2001-2002 is when it was when things were actually looking very bad for technology and Technology businesses and startups and the ability to get funding we are unable to get funding for the game that we are working on and so wicker was a kind of a Hail Mary that we were able to turn into a very successful business and then let into the whole Web 2.

0 era social media as we know it now, although when we conceived of it, it was not social media.

It was an online community successful Hail Mary and we survey the landscape of Hail Marys and the entrepreneurial World.

A lot of them don't work out and a lot of these Hail Marys don't work out the assertive can a death knell last gasps for breath as funding is running out often those do not work out but some do and there are some examples of these these pivots whether it's Twitter or Flickr others that did work out the can you discern what? Perhaps the ingredients were that made it a successful to it / Hail Mary.

Is there a particular way you guys thought about it anything at all that that you that you might attribute the success to? you know, it's funny because there's a conversation I once had with another investor who said that there's some entrepreneurs that are just so bullheaded and stubborn and they won't quit that companies really go out of business when the founder just quits when they stopped when they like I can't take it anymore and when I was But I was so, you know kind of in the valley.

I saw several examples of this.

I was I was dating F Williams the Twitter founder at the time.

And when it was a cut it was an amazing thing to see actually because I've had completely run out of cash.

This is the story of startups everywhere your it's a race against the bank account really and had nothing left when he was starting blogger, but he just kept on going it was it was a miracle it was it was amazing to watch.

He was eventually somebody was eventually acquired blogger was eventually acquired by Google Google web public.

He then had more cash was able to start the obvious Corp which then incubated Twitter and having seen that right first-hand close up that kind of willful determination.

I see that again and again and when you see things like the pivot that we went through.

I mean we were little bit living on, you know cup noodles and not getting paid and the only guy that we Getting paid with the guy who had three kids on our team and we were we talked about fumes.

We were really driving on fumes and then and then a miracle happened what happened was we had submitted an application to the Canadian government liquor was started in Vancouver Canada and We have been rejected actually for this for this funding for our startup game never ending and we had apparently check the little box that said resubmit next year because what happened was we were truly going out of business.

I think we had taken money from our friends and family and all of that money had had had been spent and remember this it was it was December 23rd.

It was 2 days before Christmas a letter arrived saying congratulations.

We are giving you this grant the start of France and it came out of nowhere really, I mean we didn't have enough money.

We had like maybe a month or two left to pay are front-end engineer and that was an end to this came out of nowhere and that was what enabled quicker to get off the ground.

So yeah, it was it was you know, Where's the Super Scrappy operation? This is days before like AWS, and we just didn't have a lot of cash and literally the The servers were in a colocation center and we literally had the phone number of the woman who worked down accustomed to it.

Call us up and say hey your new server has arrived from Austin, Texas Dell has sent you the new server.

We would rush down there plug-in our new server at the Coalition Center and load up the software and keep going.

It was just it was a super sketchy.

Foundation on which all of the stuff was built some luck involved with the checking of this box at the but there were I would imagine also some some good and probably some bad decisions that were made but probably some good decisions that were made that in retrospect contributed to what flicker then became.

I was wondering if if we we could explore one that I have just here under the through exploratory bullets, which talks about You and I think it's George Oates spending 24 hours a day 7 days a week reading every single person who came to the site.

Is that is that is that true? Is that something you guys did surf manually greeting everyone to came to the site in an effort to build community or what was the rationale behind that if that's true? Yeah.

I mean, I think that's to some degree true.

We had I remember I looked back in the first three months of flicker the team each had posted something like 50 posts a day in the forums on people's photographs and Had really been very strong participants in the community as it was being built and I really am a big believer in this actually write an article for wired.

It went I'm talking about how if you read the Bible there's Abraham begat me know someone said we got so and so big at so and so and it goes on for pages and pages and I really do believe that the entrepreneur is the is the Abraham of the company is so therefore is dictating what the practices are of the community how everybody behaves how people respond to other people's photos.

All of those things.

I think are are basically how communities are built and staying involved in being involved in having that conversation and being live in that conversation.

All the time is a really important part of building an online community and all of this went off the rails a bit when online community was renamed and repackaged as social media because What became a media platform in which people's attention to be sold? And as we later discovered people's data could be harvested and also sold and that's a very different way of building something then building a community from the ground up, which is I think what we are trying to do.

And so I think the community even now has been acquired by SmugMug.

It's it's got a new life ahead of it.

That's really the foundation of why it was such a strong community and how even after the Yahoo acquisition and many years later continue to be a very strong community in a bottle of community online.

It also strikes me how how many companies that later become very reviewed is very large like Airbnb in the in the beginning of this also reminds me of this whether it's Tina Brian or were Joe gebbia.

I know better talk about the early days of Airbnb.

It was highly highly manual and they would do things that didn't scale very deliberately until they had to create a system for it.

But in the beginning it was really really high touch to build that community in the very early days and it's see it seems to be something that is sometimes missed by entrepreneurs Who start something and beginning on day one want to scale it to a million users are 10 million users or however many million users.

Are there any other decisions or behavior is best practices that you had in those early days? Do you think we're we're critically important? What's your door or mistakes? Either one? Yeah, I mean, I mean it's funny because when you look back at something that has been successful, I think there's a tendency among entrepreneurs to attribute it to some action that they took Shand is that we were extraordinary lucky we had we had invented this at exactly the right time and what it happened was all of these things were converging at the same time Friendster had come out and gotten people accustomed to the idea of having a profile of themselves online and more than half of the households in America had Broadband for the first time more than half of the phones were being shipped with a camera on them.

It was just an Unstoppable Juggernaut because of the time in which it was invented.

Right part of that was being smart and addressing that market but a lot of it was also I think we are extremely lucky and well-positioned to be taking advantage of all of these flows of information and Bill gross who started idea lab and has been the progenitor of I don't know 500 companies many many companies.

He looked at the successive.

What are those businesses in a many of them succeeded many of them failed and tried to figure out what it was about the companies that succeeded that help them to succeed and he looked at the team execution the financing the market they were addressing the timing all of the things that potentially contribute to a startup success and what he discovered was that more than anything timing timing was the thing that made this company successful and I think that if this it happened 10 years before a ten years after even five years before five years after it wouldn't have had the same momentum as it does now and I look at this as an investor now with the SVC my my investment firm are always looking for companies that have timed it just right that have found found a parade in front of it that have are part of a movement because when you have that kind of movement behind you, there's some kind of cultural change that's happening there something that people believe very strongly and there's a change that Society wants It makes it so much easier to to get ahead people people are more inclined to want the product or the service.

They're more inclined to talk about it.

It's starting.

It's it's already in a in a in a flow.

That's moving forward.

How do you actually maybe we can look at this in a specific examples to let steak? And in this may not be an example of this but it it could be if we look at Kickstarter.

I'll see you when you were the first investor in Kickstarter or what overest and I actually invested in it when it was still a PowerPoint deck.

It was it was not built yet and Perry and UNC and it was it was actually brought to me by Sunny Bates who I think remains on the board now, it was so clear that that Had to happen and it was it was something that you should have felt in the culture.

Something that you felt around conversations that were happening online.

And this was a possibility that needed to bear fruit.

It was it was it was very it was very clear and I think a lot of the things if you look at for simple Etsy Etsy was at the Forefront of the DIY handmade movement.

It was a kind of a rebellion against big box retail and a return to the marketplace which has always been a very person-to-person community-oriented place.

I've traveled in for example in a child in Syria and went to those suk's the big Market places in Aleppo which have now been destroyed tragically and all of them.

That was the kind of the one of the most ancient marketplaces in the real people who would is like a Caravan Surrey people would bring their camels and you know, kind of Medieval times and informal Market there and you could see that that was the Genesis of you talk about the Genesis of Airbnb were flicker.

All those other companies at Genesis of markets was really sitting down having a cup of tea and negotiating for your rug and Etsy had that right as he had that and Kickstarter had that is very kind of person to person experiences that were manifested in places like Etsy and Kickstarter and Flicker and a lot of these products at the very outset and I think that that's another thing that happened at the very beginning of Airbnb.

It was very much about people coming together in a very essential and human way and that was what set those companies on such a strong Foundation.

And what did you what in what did you see that other people didn't see or what an able due to see what you saw that got you to.

Yes with say Kickstarter.

Or at sea or other examples that that might come to mind because a lot of these companies that are name brand.

Now, I faced a lot of rejection and a lot of nose and people didn't get it even including people that most folks would consider quite smart.

It's true for Airbnb Uber turn down by five hundred people on AngelList when it went out and what did you see that other people miss or to do it.

Did you have Is that could be in the in the in the companies themselves were in the founders or anything else? What what what did you see that that got you to? Yes, because because I've started starting to run myself and you but a lot of Founders will come in and they'll all very high percentage will claim that they found that parade right there in front of these three converging trends that are inevitably going to sweep the world.

How do you how do you how do you end up picking wedding on the ride horses? Like we were saying earlier my difference helped me.

I'm also a woman in a male-dominated industry.

I'm a mom.

I have this many things about me that are non-typical and when I was when I first saw at see it was as beautiful thing.

I actually took it to read half man who had invested in my first company Flicker and a bunch of other people in the valley and they kind of lifted their eyebrows and said, okay, so let me get this straight.

This is a bunch of women mostly knitting sweaters and selling it to each other and it said exactly don't you see the opportunity here coming from Humanity's background where I had spent a lot of time studying culture and society and people and what was happening around me and human interactions and how the culture was changing gave me a special.

into into that world that was missing that somehow other people weren't seeing that was non-typical was outside of the pattern recognition of Silicon Valley and a lot of the Investments that I have made have fallen outside of the typical pattern recognition that everybody takes advantage of in order to spot 6s.

And I think I've always had I've always had that my partners at founder Collective.

You should tell me this all the time.

I would bring in Deals.

They say that your deals don't look like anybody else is still very different.

The people that you're backing the people that you consider as potential entrepreneurs fall far outside of what is typically understood in the valley as a typical investment and they said this to me kind of over and over again.

Like wow, where did you find these folks? What's the time? They found me and I think part of the reason that we started yes VC and we wanted to start a brand new firm was because we saw that there is a sea-change happening in technology and that people that were non-typical people that didn't fit this the typical pattern of an of an entrepreneur as defined by the valley cult.

We're now liberated from a lot of prejudices that they've been working against before and if there had been an investor in 2004 when I was raising money for flicker that looks like me I would have gone straight to her.

But there just weren't that many and so I think things have changed a lot and non-typical investors people from outside of Of of the valley people that are in different regions people of color women.

I think there's so much more opportunity right now for those kinds of businesses to flourish and are being given a voice and when all those companies were where started it was actually much harder.

To find people who understood those business models those Founders and there are in teaching.

So let's talk about a typical and you as a typical investor for a second because I this is part of the reason I was so excited to talk and I'd love to chat about a bit more about the few things.

You mentioned.

She mentions your familiarity with culture Society people and then whatever was 5 or 10 minutes ago.

We talked a little bit about timing and so the question that jumped in my mind and this is going to be a bit of a long question.

So bear with me was how could someone who wants to cultivate that type of weirdness go about developing a bit a better perspective or different lens on Cultural Society people and changes that end up getting in some ways represented by these fantastic opportunities like Kickstarter or Etsy.

I've read in the doing homework for this interview that you've recommended for entrepreneurs.

Books like the innovator's Dilemma, but I also read on your site Katarina.

Net a paragraph.

You think you'll recognize this is from 2018, but, not Stewart Brands work and and I'll just read this cuz pretty short sew through Stewart Branch work beginning with how buildings learn one of my favorite books of bread sees in his work with the long now Foundation.

I learned to look at time differently and technology different Lane to think about.

How time is cooking to everything we do today, especially as regards the ephemeral nature of all the time spent on computers in an online media.

So I'm curious if seis how buildings learn or Stewart Brands work would be something that you would recommend people were coming out of Morrissey should have CS or pretty typical Silicon Valley back on if they wanted to develop some of the perspective that you have.

Are there any resources or books or warm ways that you would suggest people exploring? I love that you brought this up Tim because part of the reason I was super excited to talk to you about this is because I think you and I share an obsession with time and your books are the four hour work week the 4-Hour Body all of these things having to do with time managing your time thinking about time and when you really look at it from the 35 thousand foot view time is all we've got and I have been a time time management is possibly the thing that I've done most in my life in terms of generating the kind of life that I have wanted to lead and that comes from it went way back back to when I was young and I was actually forbidden by the dean at my school from taking any classes before noon because I'm just one of those people I work really well at night.

I'm a night owl and I could not make it to my classes in the morning.

I actually failed photography class because it was at 8 a.

m.

I couldn't do it and I honestly believe that one of the reasons I'm an entrepreneur and I have always worked for myself is so that I can manage my own time and have always thought that the highest quality of living the highest standard of living really comes from being the master of your own time deciding where you want to go in the morning what she wanted to do and that that is so important and knowing that when you have the energy to put into your work you can do that whether or not it happens at 8 a.

m.

Or if it happens at 10 p.

m.

And actually gave her an interview business week once about my peculiar schedule in that I wake up in the middle of the night between 2 and 5 in the morning and I do 3 hours of work.

I don't turn on the computer.

I I write everything on on paper.

I do my best thinking and writing and ideation during those hours in the middle of the night going to go back to sleep and get up and carry on with my day.

But without that that kind of pocket of time where I'm uninterrupted said, I'm offline.

I'm free and liberated in a way that you just don't get during the work day.

It's it's a magical it's a magical time.

Side so many questions, this is great.

This is great.

So I was going to ask you about this waking up between 2 and 5 a.

m.

I didn't realize that you went back to sleep.

So this I've been reading up explain why maybe another time but on the history of lucid dreaming and it appears that biphasic sleeping or people can a wake up and have have a first sleep wake up and then go back to bed at various points in history has been quite common.

It's not something that I've done a whole lot of but could you give us an example of what you might work on on paper in those three hours? So you wake up at some point between 2 and 5 a.

m.

Specifically, what do you then do is it something that you've already planted at the top of a piece of paper as a prompt and you know, you're going to work on a specific problem.

Is it like long hair and stream-of-consciousness? What do you do during this handful of hours? I have done it really depends.

Sometimes I wake up and I I I've always written books.

So I have I've been working on a book now for the past three months a new book.

I write sometimes poetry.

I sometimes just open up my journal and start writing.

I can be working on a big problem The Five-Year Plan for my startup or something like that any kind of big picture thinking any kind of thinking that involves creativity intuition.

All of that the kind of the right brain and not the left brain and I've studied all of these people have come across these articles.

There was an article that was recently sent to me that was about the some extra forget his name, but he was an AI Guru.

I think he's from Cambridge and the thing that I did not manage to read the whole article because I got stuck on the very first half where it describes how this Cambridge AI genius woke up and he didn't communicate with anybody until noon and that he managed to have a relationship with his family and they had developed a language of Grunts and smiled so that he didn't have to his thoughts didn't get interrupted.

And then when he finally went to work around noon, he had one meeting.

And I was like, oh my God, this is a master of time management and preserving that flow state in your head and preserving the ability of yourself to think and wonder and ideate is so precious and should be defended ferociously at all costs and I've always felt that way.

I've always had this this very I call it like cognitive dispense really powerful cognitive defense and this it's interesting because this also shows up in some of the Investments that we made for what am I serious about cultural movements right now is that there's a very strong desire to simplify your life for being constantly bombarded with information with marketing with new products and you walk into A grocery store and you're confronted with a hundred and eight different kinds of toothpaste given moment of the day.

And one of the Investments that we've made us as company called public goods, which basically gives you one shampoo.

Wen conditioner one dish soap and sent it to your house and so you're not confronted with all of this.

Paradox of choice right which which which actually people want to reduce some people want to constantly reduce the amount of stimulation so that they can focus and so that they can live a more deep and fulfilled life and I really think that in our our society today you need to pick, you know your podcast and hopefully my podcast and eliminate all the others.

If you see what I'm saying, you have to you have to focus in and narrow down and eliminate a lot of the noise in your life as much as possible to free difficult thing to do and so I see the time management part of our Lives as being just a crucial thing to to defend our our space our happiness and our individual lives.

I was looking at your site earlier today and found a an example of removing noise and it was still example but might be a jumping-off point for exploring other examples.

This is a DF tube that is distraction-free to which is a plug-in that you use to clean up YouTube removes the recommendations on the sidebar the crap on the homepage inane commentary poof.

That's so I made a note to use that myself.

Are there other tools any other tools or Books that you found helpful or approaches that you believe very strongly in them in the ud the waking up should have in the witching hour and and working for a few hours without a screen is I think it's great example other than you have the very tactical can I micro to or like something like this extension other other other things that come to mind that the youth found or find particularly helpful? When I am at my most flourishing and productive self, I'm actually online a lot less and there's now all of these tools screen time on Apple on the Apple phone and all of these things that that I think or are great and during the periods in which I think I most most flourishing was productive.

What I'm doing is I'm going online.

I did I did this for as long as I can and I I fall out of the practice.

Occasionally, but I always try to get back his I would schedule a time to do my email in the morning.

10:00 10:30 to 12 or something like this and then again in the evening 4:30 to 6.

And I would be offline as much as I could during the times in between now a lot of us have work that we need to do and and things we need to do online.

But to be super disciplined about the time that you spend online I think is is really important and I've always done this and I have a a kind of a notebook that I keep.

Next to my computer and it says wno on the cover, which says when next withstands Berwyn next online and you just write a list and it says, you know, I need to email my accountant.

I need to look up what the name of Bob Dylan's second album was I need to go fix this misinformation on this Wikipedia page.

Whatever.

The thing is that you have these urges during the course of the day to go online and then the next thing you know, 3 hours have passed and you're watching.

Unboxing videos on YouTube right? I think that you need to just get on top of that.

I think it's a really important thing that you can that you can do.

This is this is a kind of a major thing.

I fall out of this all the time.

I am, you know, you see me watching unboxing videos on YouTube all the time and constantly bring yourself back to that and realize how much of a Time suck that isn't it can be and realize also that it's it's that kind of activity.

That's that's taking you away from a life fully lived.

I remember reading an article on quora where somebody said I want to be an entrepreneur as successful as Steve Jobs and Elon Musk.

How do I do that? Right many people would like to know the answer to that question.

And one of the respondents was Justine musk Elon Musk sex ex-wife, what are the things that she wonderful because like she knows firsthand actually what it takes to become we're to be Elon Musk and she responded to the first of all Elon Musk would never be asking this question in a Korra Forum because it's true.

He was he was off building.

PayPal is building Tesla was off doing that and not wondering how if you seen him saying it wasn't kind of reading forums endlessly about about that but was was out instantiating those ideas and that that really stuck with me because I think it's true.

You can spend a lot of time and preparation and I think that's good to add to an extent to a degree but really really living it really being in it.

I think is the most important thing.

shh it's so I always have to reel myself in in a sense because I love reading and reading is a very socially acceptable form of procrastinating.

So I'm certainly guilty of that at times but the summer Kathy Sierra long time ago said to me yet or she might have been in a presentation she gave but I was sitting in the audience about fixing on just in time information not just in case information and that really struck with me stuck with the excuse me to have a tendency to is Trump trying to stockpile information in case the 1% chance that I need a b and c in the next 6 months, but it's not a very big.

Is that a great used time you write poetry and correct me if I'm wrong here, but I have some of your favorite poets including Wallace Stevens Shakespeare Emily Dickinson.

Why do you write poetry? What do you get out of writing poetry? What does it do for you? It seems to be a kind of an external expression of an internal state.

It seems to be the recognition of and valuing of the inner life.

I read.

Something that somebody had written.

Let me let me try to figure out who it was.

I can't remember if it was it was something that I read just the other day.

That was was was worrying and was very concerned that our modern world made it impossible for people to have an inner life that the inner life was Vanishing from the world that our life was so much of the time that we would normally spend with ourselves with our dreams with our thoughts was Vanishing because it was being filled up constantly with stimulation entertainment.

And our compulsion to to be online and and and basically what I see is sort of security exploits of the brain that the internet has managed to insinuate into our lives and that poetry writing dreaming paying attention to those kinds of things and the cultivation of an inner life is something that you have to deliberately do that.

You have to protect in your in your life and make time for and recognized as important and frankly not do many things many of the opportunities that present themselves are just it's just terrible how much fomo is created by the internet.

It's it's it's endless and there's a thousand places that you and I could be right now at a thousand experiences that we could be having things that we could be doing.

And those of us who are like you like me like a lot of the listeners are optimists where possibilist for people who believe in you know, living life to the fullest and the internet, you know, kind of both cultivates that and makes those opportunities available to more and more people, hopefully and and yet Too much possibility as we've discovered shuts down and deprives us.

Fully lived experiences.

And so I mean it's interesting because poetry has always been part of my life.

I was a bit of a rebel as a kid and as a student and I've always had a very difficult relationship with institutions.

I think my kind of very anti-authoritarian nature is also one of the things that led me to be coming in an entrepreneur and I rebelled against these the structures and one of the very earliest instances of this was in first grade when all of the other kids were learning to read and I already knew how to read and I was basically becoming a break with trouble in the classroom for the teacher because I was like inpatient night.

I wanted to read and so I went to the library and I sat and I read poetry with the librarian.

Remember this I was I was I was in like five or six years old and I still remember some of those poems.

From when I was a kid and they were just there like kind of Rhymes remember? Once there was an elephant who tried to use the telephone.

Oh, no, I mean the elephone who tried to use the telephone Jeremy.

I am not certain quite that even though I've got it, right.

It seems somehow he got his trunk and Tangled in the telephone book the more he tried to get it free the louder Buzz to tell if he I fear I better drop the song of elephant and telephone.

It sounds it sounds like a great metaphor for what happens to brains when they encounter the internet for hours a day.

How on Earth do you remember that? That's incredible I have this is crazy memory and I have I have for a long time.

I think since I was in my early teens I decided that I would memorize poetry as a way of bringing the beauty of thought and language and I always felt that poetry was one of the highest achievements of human thought and beauty and a kind of an Embrace of the world.

And so I wanted it to be part of me.

And so I started memorizing poetry is a way of bringing it into my unconscious as a way of having it always with me from a very young age.

And so I started memorizing poetry.

as a bit of an eccentric teenager and I have a have a lot of that love of poetry but it's deep inside and I can recover a lot of this poetry at times when it's when it's needed when you're going through some kind of Crisis or difficult times were in a depression or like some kind of bad State you find yourself in suddenly some Oracle from deep in the unconscious will come out and Shakespeare will have said exactly the right thing and you'll then know what to do.

It's a kind of this amazing strategy that I've kind of trade with me my whole life for those people listening me who like me have minimal exposure to poetry or at some point.

We're introduced to the wrong poetry, which was just completely confusing and seemingly designed to remain abstract an obscure and confusing his other any poets.

Or collections you might recommend people start with if they wanted to dip their toe in the water of poetry the and that the best way to start is to just go to his poetry.

org.

It's it's just wonderful wonderful font of poetry and just start digging around and find what you love.

I mean you mentioned some of the ones that I love I love Wallace Stevens.

I love Emily Dickinson.

I love Shakespeare.

I wrote my thesis in college on James Merrill.

I love w h Auden it just goes on and on.

we could talk for hours about 4 hours about this but it's it's it's important that we do this.

I'm going to Tim if you don't mind dig up this quote from Charles Darwin.

There's this beautiful thing that he says, I think that this is a beautiful thing because he is a amazing.

He's an amazing scientist and he lived the life of the mind and Darwin's regret was that he had become he said a machine for grinding out facts and figures.

He had become a machine like in his thinking and he said later on in his life.

If I had to live my life over again.

I would make it a rule to read some poetry.

Listen to some music and see some painting or drawing at least once a week for perhaps the part of my brain now atrophied would then have been kept alive through life.

The loss of these tastes is a loss of happiness.

And I think it's very powerful coming from as great a scientist as Charles Darwin because we live and what I call the Technic we live in a world of mechanistic being and thought and Science and all of those Passions.

That throughout throughout, you know, since time immemorial has sustained Humanity.

are getting lost somehow or there their they're slipping away or their they're not part of our daily life.

And I think we have to deliberately put it back in and continually put it back in.

And make sure that we don't lose it.

Do you how much of the Poetry that you write for yourself is remains just for you and how much of it do you show to other people? I would say 100% of it is remains just for me.

I have it.

It's interesting because many people have asked me this over over the years because I've actually written a half a dozen novels.

I have written probably at this point two or three books of poetry if it were to being published for him, but I have somehow never let any of that out into the world and part of it is that it's such a precious part of me that I'm in some ways.

I have a very strong tendency and desire to be successful in the world and I read that it will be go out into the world and will be subject to the same.

Laws as have led to my success in business, which it's a very different thing and so it's funny because I I find it everyone's like, oh my gosh, this is crazy publish this when it's encountered and then I'm kind of like maybe but in the end.

It's so valuable to me.

That in some ways if it were to escape out into the world would lose some of its power.

Kiana think that's very wise to protect that and I run tint after the after the first after my first book.

I have run into a lot about Nurse who talked about say taken.

Is a lifestyle business something they love doing in their spare time on say Saturday afternoon's going surfing something like that and turning it into a business and I'm always very hesitant to recommend that because if it's something that is this creative outlet that is pure innocence and gives them some reprieve from the expectations and pressures of the outside world.

It's very smart to keep that for yourself and you talked about very deliberately building these things into your life and you also mentioned a name and I might be pronouncing this correctly.

But wh Auden am I getting that right and there's a quote that I pulled up because I could only remember the first line but that.

I'd love to talk a little bit about your routines in the quote goes as follows routine in an intelligent man is a sign of ambition of courses plus everybody but routine and tells your man has a side of ambition of modern stoic knows that the surest way Discipline passion is to discipline time decide what you want or ought to during the day then always do it at exactly the same moment every day and passion will give you no trouble.

I've read that you very often will eat the same entree at certain restaurants.

If you decide you like something or other are their routines that are particular and particularly important to you aside from those.

We've already discussed anything that you make sure you do in the mornings or the you make sure you do and winding down or do you do once a month once a week once a quarter that any particular routines that help you? In structuring your life and in your time that you can.

They can think of.

I have a I have a very idiosyncratic schedule and the The reason for that is that I have you know, like you say I find I find nothing in the restaurant that I like and I always order a burger because it's been proven again and again that the burden of decision-making wears you down.

And that the fewer decisions that you make over the course of the day the better decisions that you can and then we're energy that you have left over for the important decisions in your life.

And so, you know famously Albert Einstein had one suit of what she had five different versions or something like this so he didn't have to think about what he's going to wear in the morning.

He you know, it's the same as if these these patterns if you figure out what it is that you're happy no longer making the decisions about his kind of one of the one of the principles behind public goods and it was coming that I mentioned earlier is that you don't have to think about what shampoo to buy you just have to think about it any more kind of check that box.

It's done you got a default and so building these defaults into your life.

Are super important things that you don't want to think about anymore and whether that be what you eat what you wear things that you're less invested in so that when you're in you don't like my my my Witching Hour, you know the hour of the wolf or whatever you call that when I'm in that state I can go wide right I can I can make a thousand decision as I can.

I have I have freedom to go into in a dark Corners that I haven't yet explored that I can can stink really broadly and be more creative and have dreams and you know kind of Revelations that are just not possible if you're kind of crowded into kind of tiny decisions all the time, but actually, let me take take a step back.

So you mentioned in passing something when we were discussing poetry and how certain poems or phrases would come to Find it that seemingly that the perfect moment when you needed them most.

And you mentioned depression very briefly is that that's certainly something I have some some personal experience with is that something that you also have personal experience with a depressed teenager Superbad.

Of my life when you know, I was in that kind of state that's familiar to a lot of depressed people where I just couldn't get out of bed in the morning and just wanted to stay there all day and was reluctant to expose myself to the world because I felt very vulnerable and needed to basically hide in my cave and I think you know many of us go through these.

I mean, I think it's kind of just common to The Human Experience at this be a estate and there's a reason for it.

I just I just like the Term depression because I think a lot of it is more.

Is better described as Melancholy or just spare or there's a older words that describe its sense of clinical to to talk about it and and in the terms of depression because I think that it's part of a fully live life.

To go through these periods of deep unhappiness and dissatisfaction and questioning and despair even and that without that you kind of if you live Always On the Sunny Side of Life I talk about this in an in kind of the jungian sense of of the Shadow, right? You constantly rejecting the shadow if you're constantly living life on the sunny side.

I mean, this is what happens on social media and this is why social media can be so diminishing of people's humanity is that people are always I caught social peacocking right? They're showing how great their life as they're showing all of their happy moments are showing all of their successes and not their failures all of their triumphs and not their doubts and Basically providing a highlights reel of their life in this is very damaging to to the psyche to people's Humanity of not acknowledging living and frankly giving time and space to those parts of yourself that are less Savory that are in a mistakes.

I see it all around and you know, you see it all around right? You kind of look at all of your happy successful friends.

On Facebook or Instagram or where have you you know, they're always going fabulous places and doing fabulous things.

But what about The shadow rate like what about the shadow? This is really wonderful essay, which I encourage everybody to read by the science fiction writer Ursula Le Guin about the shadow.

I talk about it.

There's a blog post on my website that's called social peacocking in the shadow and in it.

I link to a short story by Ursula Le Guin about the shadow, which I think is a very important part of people's Humanity, which somehow is not being given space online.

Do you suggest weather without you suggest you can either suggest or talk about your personal experience people accept the Shadow or work with it without falling into a a dangerously deeper extended state of despair.

The way to start out with that is to accept the shadow in other people because we have this idea of other people.

as being more Yeah, Rich successful, beautiful happy they're in a better relationship there.

You know, they have better teeth their hair thicker hair.

I don't know what that thing is some insecurities that we have we seeing others as as something that we don't don't have and there's a wonderful sonnet by Shakespeare on the subject.

I think it's on it.

What does that it's on at 29 by by Shakespeare? When in disgrace with fortune and men's eyes, I all alone beweep my Outcast State and trouble deaf heaven with my bootless cries and look upon myself and curse my fate wishing me like one more rich and hope featured like him like him with friends possessed Desiring.

This man's art and that man's scope with what I most enjoy contented least yet in these thoughts myself almost despising happily I think on the and then my state like to the Lark at break of day arising from Sullen Earth sings hymns at Heaven's Gate for thy Sweet Love remembered such wealth brings that then I scorn to change my state with Kings.

It's a beautiful and I think what it speaks to is the the kind of the envy In a wishing me like one more rich and hope you know featured like him like him with friends possessed and you see it all around you especially when you're in the state of despair and it seems as if the world all around you is full of delight and success and happiness.

That is somehow I'm available to you.

But with the sperm does is it happily I think on the right and often this is red.

Is it a love poem as a kind of a celebration of the relationship that Shakespeare is presumably and when he's writing all of these are all the sonnets, but when you really think about it, you know, mr.

Rogers famously says like to think about all of the people that loved you into being right those people are not necessarily your lover, but they're your mother there your sister there's that teacher that saw something in you that other people didn't see it's your friend and it's all around you.

I just have to do is kind of stop looking at those people that have the thing that you wished that you had and look to those people that saw that and you and realize that they're all around you.

So that's what that poem.

That's what that kind of does to me and I have you know, I kind of feel as if if you have all of these poems and kind of their deep inside you that they will come to you when you need them.

This is You make me make me sick a bit.

I haven't thought of it in those terms.

But only in the last few years.

I've started reading some very very easy to read very easily digested poetry by people like, you know, Hafiz and Sufi poetry Rumi as well and they do stick they really do stick and they seem to have a particular stickiness.

Greater stickiness then press more clinical nonfiction write something that is really artfully woven into beautiful language just has a higher stickiness Factor because these poems do come to mind at the right time.

Just never thought of it quite in the way that you're presenting it.

Do you do you or have you found anything else useful for? Embracing the shadow but not falling into a pit of despair or if you for or of or if you've run into entrepreneurs who are going through a pit of despair, which is certainly not uncommon.

Are there any particular recommendations that you've made her would be prone to make well, I think that when people are depressed or also in some ways ashamed of it and I think that's that's one of the things that makes it feel.

So isolating is that we feel that other people.

Will judge us that bad things could happen as a result of are revealing these these parts of ourselves that are so troubled are disappearing or unhappy or failing or unsuccessful and that we always feel as if we've got a present our best face to the world and in this can be one of the things that makes it impossible to get out of it.

And so what is the thing that's most important in especially in our world of diminished relationships with others is to constantly be in communication with others to know who our friends are to revive those lost friendships that we've had in the past that are very meaningful to us to resume our closeness to others and frankly to as roommate would say in one of his beautiful poems cry out in your weakness.

Of course, there's a poem for everything but this one is in a cry out in your weakness because there are helpers in the world who will rush to save anyone who cries out like Mercy itself.

They run towards the screaming and cannot be bought off.

And if you if you address your suffering to others you find that the suffering is universal that we all go through these moments of Shame and dignity depression and happiness failure and that anybody who's pretending that they don't It's just not true and you're crying out loud and weeping.

Remy says are great resources right give your weakness to one who helps a beautiful poem.

It's what I think of you if you search for it's like called cry out in your weakness and that is a very meaningful poem.

I think for people who are suffering because it's basically giving you permission, which I think a lot of people need to cry out in your weakness yeah, it's I really appreciate you being willing to talk about this and explored a bit because it is a constant like you said and it kind it's it's come up so many times in this podcast, whether it's with these the brutal stories of rejection that bread and standing of humans of New York is is telling or any number of not hundreds of examples that have come up.

It's like you said it's a it's an illusion and it and it really be crippling illusion when you're not only depressed but are ashamed of it feeling like you're somehow you deeply flawed because that's just not the case.

So I appreciate you being willing to to chat about this and Maybe we can make a sabbatical he continued on the shadow side for just a few more minutes and then we'll will shift gears.

But you have incredible memory you have incredible track record.

I think a lot of people listening or some people would certainly find that very intimidating which is part of the reason.

Also, I wanted to bring up the depression just to humanize the the profile a bit.

Are there any failures? We've talked a lot about successes and no names but are there any failures are apparent failures of yours that have set you up in some way for later success of any noteworthy failures that come to mind then if you don't like the word failure you could do something else, but I mean, it's It's perpetual.

It's hard to single out.

A single failure when looking at the you know, you kind of look back at your your miseries your failures the companies that didn't succeed the relationships that didn't succeed the great hope that you had in 04 this or that and kind of realize that you spent years and years working toward some kind of field projector a relationship that didn't work out her in a some some kind of trap that you fell into and you know, it was it was a struggle to Free Yourself.

It's funny because I think that my orientation.

as a Perpetual optimist leaves me with a a kind of a sense of Forward Motion from all of those things.

I mean, I do think you know, one of the things that we talked about was how when I was a teenager, I went through a very deep depression and a state of despair and Melancholy and periods are very formative.

They are very important you go back to them and those moments when you're at your worst at your weakest that you're at least successful at your kind of most alone and look back at the path that you took out of them and the ability to emerge from them and sit kind of keep going in spite of them are some of the most meaningful parts of your life is that you have you have really just reached the depths of Despair and then have kind of recovered from them and the importance that that gives you going forward and your strength comes from that right and if you're never tested and you're never in that kind of situation you got help you.

I'm it's not it's not a good state.

Write it.

It's a kind of the fullness of your humanity is kind of emerging from those steps.

I've always I've always kind of felt that and without that, you know without that experience when I was teenager without some of those experiences from my childhood without those experiences kind of like perpetually throughout life life cycles through highs and lows like that and and and to appreciate those periods and not to struggle to ignore them eliminate them from your life is I think one of the healthiest things that you can do And if your people listening who are willing to have that broad spectrum of experience, including the dark moments, but are listening with Envy to your talk of optimism.

Are there any any books any I know this is kind of a sad that the type of question that won't die for me, but are there any tools habits books anything that you would recommend people who want to cultivate a more constant optimism if it's if they might have been just beaten into cynicism by spending too much time on the Internet or what what what what whatever it might be.

What would you I mean, honestly, I think that a great deal of Of emphasis on long-form reading I think you and I both Embrace this and love books and love reading and you know, I know your uniform off Sophie and Seneca and I read young and poetry go long for I'm not short for him go deep right and not broad.

I think that this is actually a really important thing and you know, there's a dozen books.

Maybe we can I can even write a list of these and you can post it in the in the Heights.

Oh my gosh a list of a dozen or more books that have helped me throughout my life.

For sure 100% Yes, and yes, if you could mention any of them now, you don't have to mention all of them.

But I m