Caterina Fake: Lessons from Flickr, Kickstarter, Etsy, and Much More – The Tim Ferriss Show

Check out The Tim Ferriss Show Episode Page & Show Notes

Key Takeaways

  • Embrace your different background and use it to your advantage
  • Often, more than anything, TIMING is what makes a company successful
  • The highest quality of living comes from being the master of your own time
  • Caterina has quite the unique schedule:
    • She gets up every night between 2-5 AM to get some deep, focused work done – without the use of a computer or the internet
  • Caterina has a notebook she keeps next to her computer which says “WNO” on the cover
    • This stands for “When Next Online”
    • In it, she keeps a running list of the things she needs to do when she next plans to use the internet
  • So much of the time we would normally spend with ourselves, our dreams, and our thoughts is vanishing – it’s filled up constantly with stimulation, entertainment, and our compulsion to be online 
    • “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 and you have to protect, make time for, and recognize as important”
  • Caterina recalls a quote from Charles Darwin
    • “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.”
  • Automate your decisions where possible
  • On depression and hard times:
    • You are NOT alone
    • “Those periods are very formative. They are very important. You go back to them, those moments when you’re at your worst, and look back at the path you took out of them. The ability to emerge from them and keep going in spite of them are some of the most meaningful parts of life. Your strength comes from that.”

Books, Poems, and Other Relevant Mentions

Intro

Caterina’s Last Name – Fake

  • Caterina has had flights canceled in the past by airlines (specifically KLM and Northwest) due to her last name
    • She no longer uses these airlines
  • For the first two years of Facebook’s existence, she was unable to make an account

Embrace Your Different Background

  • From the age of 10, Caterina knew she wanted to be a writer/artist
  • She graduated from Vassar College with a degree in English literature
  • “I really think that people who come from outside the [tech] industry have a superpower that people who have lived within the industry their whole lives don’t have”
    • Why? – You’re able to see things in a different way
      • “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”
    • Caterina has always encouraged entrepreneurs and others who are interested in entering the tech industry to really emphasize the parts of themselves that are different from mainstream expectations
    • “Coming from a different direction is almost always an advantage”

Flickr

  • The company actually resulted out of a quick pivot, after Caterina and her team were unable to get funding for a game they were building (she doesn’t really expand on this)
    • “Flickr was kind of a Hail Mary that we were able to turn into a very successful business”
      • What made it a successful pivot/Hail Mary?
        • They received a startup grant from the Canadian government – this is what enabled Flickr to get off the ground
  • Another tidbit about Flickr
    • Caterina and her team used to comment on the photos of many, many users
      • Why? – To set an example for the community, and stimulate use of the site
        • “The team was strong participants in the community as it was being built, and I really am a big believer in this”
        • In a way, the Caterina and her team dictated what the practices were for the community, how everyone behaved, and how people responded to other’s photos
        • This reminds Tim how in the early days of Airbnb, the founders knowingly did things that couldn’t possibly scale in order to help the company grow (like going to visit people who hosted their home on Airbnb to get feedback – explained more in these Podcast Notes)

Timing is Everything

  • “When you look back at something that’s been successful, there’s a tendency for some entrepreneurs to attribute it to some action that they took”
    • But it often just comes down to luck
    • With Flickr – “We had invented this at exactly the right time…it just was an unstoppable juggernaut because of the time in which it was invented”
    • Often, more than anything, TIMING is what makes a company successful
  • “With Yes VC, we’re always looking for companies that have timed it just right, and are part of a movement”
    • When you have that movement behind you – there’s some kind of cultural change that people want, and something people believe very strongly in – This makes it SOOOO much easier to get ahead
      • People are more inclined to want the product/service and talk about it as it’s already part of a flow that’s moving forward

Investing

  • Caterina was an early investor in Kickstarter
    • She actually invested when it was still in the “slide deck phase”
      • “It was so clear that it HAD to happen. It was something that you felt in the culture and something you felt around conversations that were happening online. It was a possibility that needed to bear fruit.”
  • Caterina once served as Chair of Etsy
    • Etsy was like a return to the idea of a marketplace – like souqs in Syria, or those night markets throughout Asia
      • “The genesis of markets was really about sitting down, having a cup of tea, and negotiating for your rug” – Etsy mimicked this
  • With investing – “My differences helped me”
    • On Etsy – “My humanities background where I had spent a lot of time studying culture, society, and people, and what was happening around me, and human interactions, all of that gave me a special view into that world that somehow other people weren’t seeing”
      • It was outside of the standard pattern recognition of Silicon Valley
    • “A LOT of the investments I’ve made have fallen outside of the typical pattern recognition that everyone takes advantage of in order to spot success”

How can someone else develop this different lens on culture, society, and people?

  • Caterina has recommended the book The Innovator’s Dilemma in the past
    • Drew Houston, the founder of Dropbox, also recommend this book in these Podcast Notes
  • She also recommends the book How Buildings Learn by Stewart Brand
    • On her website, Caterina has a quote about the book – “From this book, I’ve learned to look at time and technology differently, and to think about how time is cooked into everything we do today”

Time is All We’ve Got

  • “When you really look at it, from the 30,000 foot view, time is all we’ve got”
    • “Time management is possibly the thing I’ve done best in my life in terms of generating the kind of life I wanted to live”
    • “One of the reasons I’m an entrepreneur and have always worked for myself is so I could manage my own time”
    • “I’ve always thought that the highest quality of living really comes from being the master of your own time….deciding where you want to go in the morning and what you want to do…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 8am or 10pm”

Caterina’s Unique Schedule

  • She likes to wake up between 2 AM and 5 AM to do 3 hours of work, then goes back to sleep
    • But not on the computer – she writes everything on paper
    • “I do my best thinking, and writing, and ideation during those hours in the middle of the night”
    • Caterina calls this 3 hour block “magical” – as there are no interruptions 
  • What does she work on during this block?
    • Currently, she’s working on a book
    • In the past, she’s written poetry
    • Other times she just journals
    • And then sometimes she works on big problems – the creativity based work
  • “Preserving that flow state in your head, and the ability of yourself to think and wonder and ideate is so precious and should be defended ferociously at all costs”
    • “I see the time management part of our lives as being the crucial thing to defend our space, our happiness, and our individual lives”

Removing the Noise in Life

  • Check out DF Tube (Distraction Free Tube) a plugin you can use to clean up Youtube
    • It removes recommendations, crap on the sidebar, and unnecessary commentary etc.
  • Caterina is an investor in Public Goods
    • They send you 1 shampoo, 1 conditioner, and 1 dish soap to your house every X number of days, so you’re not constantly confronted with the paradox of choice – which many people want to reduce
      • Think about it – “You walk into a grocery store and you’re confronted with 108 different types of toothpaste”

Time Management

  • In the past, Caterina scheduled time to answer/write emails
    • Usually 10:30 AM – 12 PM in the morning, and 4:30-6 PM in the evening
    • She would consciously remain offline between those times
      • “To be super disciplined about the time you spend online is really important”
  • Caterina has a notebook she keeps next to her computer which says “WNO” on the cover
    • This stands for “When Next Online” – she keeps a running list of the things she needs to do when she next plans to use the internet
      • So many of the things we do online are such a TIME SUCK and take us away from the lives we truly want to live

Poetry and the Inner Life

  • Some of Caterina’s favorite poets – Wallace Stevens, Shakespeare, Emily Dickinson, and W.H. Auden
  • Caterina also writes poetry – why? 
    • “It seems to be an external expression of an internal state”
    • “It’s the recognition of, and the valuing of, the inner life”
      • So much of the time we would normally spend with ourselves, our dreams, and our thoughts is vanishing – it’s filled up constantly with stimulation, entertainment, and our compulsion to be online
      • “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 and you have to protect, make time for, and recognize as important”
  • On memorizing poetry
    • “I have, for a long time since my early teens, decided I would memorize poetry as a way of making the beauty of thought and language a part of me”
      • So Caterina started memorizing poetry as a way to bring it into her unconscious so this beauty would always be with her
    • “I can recover a lot of this poetry at times when it’s needed – when I’m going through some kind of crisis or difficult time or depression or some bad state. Suddenly, some oracle from deep in the unconscious will come out….and you’ll then know what to do”
      • Tim has noticed something similar:
        • Over the past few years, he’s begun to read “easily digestible” poetry by people like Rumi
        • He’s noticed how the pieces stick and he’s able to recall them when needed
  • What poets does Caterina recommend people start with?
    • “There’s no one poet for everybody”
    • The best way to start – go to poetry.org, and just start digging around and find what you love
  • Caterina recalls a quote from Charles Darwin
    • “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.”
  • On writing poetry
    • “100% of the poetry I write remains just for me”
      • “It’s so valuable to me, that in some ways, if it were to escape out into the world it would lose some of its power”

Routines and Decision Making

  • A quote from W.H. Auden – “Routine in an intelligent man is a sign of ambition”
  • Caterina will often find a dish she likes at a restaurant and ALWAYS order it
    • “The burden of decision making will wear you down, and the fewer decisions that you make, the better decisions that you can, and the more energy you have left for the important decisions in your life”
  • “Building these defaults into your life are super important for the things you don’t want to think about anymore, whether it’s what you eat, what you wear…things you’re less invested in, so that when you’re in your flow state you have the ability to make 1,000 decisions”

Depression and The Shadow

  • As a teen, Caterina describes herself as “quite depressed” – never quite wanting to get out of bed and expose herself to the world
    • “I think that it’s part of a fully lived life to go through these periods of deep unhappiness, dissatisfaction, questioning, and despair”
  • Advice
    • To be able to acknowledge and accept the shadow in yourself, accept the shadow in other people
      • “We all have this idea of other people as being more rich, successful, beautiful, and happy” – But it’s just not true
      • At times – it seems as if the world all around us is full of delight, success, and happiness that’s unavailable to us
      • Related to this – Check out Sonnet 29: When, in Disgrace with Fortune and Men’s Eyes by Shakespeare 
    • Find your close friends – and really be honest with them about how you’re feeling
      • “When people are depressed, they’re also in some ways ashamed of it” – This makes it feel very isolating
      • We tend to feel we’ll be judged and bad things could happen as a result of revealing the troubled parts of ourselves
      • As Rumi has said“Cry out in your weakness, because there are helpers in the world who will rush to save anyone who cries out” 
        • “This is a very useful poem for people who are suffering”
    • “When you address your suffering to others, you’ll find that this suffering is universal. We all go through moments of dignity, depression, unhappiness, and failure. Anybody who’s pretending that they don’t….it’s just not true.”

Does Caterina have any favorite failures?

  • Specifically her bouts with depression as a teen
    • “Those periods are very formative. They are very important. You go back to them, those moments when you’re at your worst, and look back at the path you took out of them. The ability to emerge from them and keep going in spite of them are some of the most meaningful parts of life. Your strength comes from that.”
    • “The fullness of your humanity is emerging from those depths”
    • “To appreciate those periods, and not just struggle to ignore or eliminate them from your life, is one of the healthiest things you can do”

Are there any books or other works that Caterina would recommend for people who want to cultivate a more constant optimism?

Books and Reading

What books has Caterina gifted the most?

In a world of so many options, why has Caterina decided to start a podcast?

  • “There’s a super important conversation going on in technology, in the culture in which we live, which needs to be had”
    • “We’ve seen what damage technology can potentially do to our humanity, and it was time for this podcast to come into being” – “This is a conversation that NEEDS to be emphasized”
  • Caterina loved the experience of being on Reid Hoffman’s Masters of Scale
  • What’s the structure of her new podcast?
    • In each episode, Caterina finds and interviews an entrepreneur building an interesting technology (some have to do with artificial intelligence, gene editing, and neuroscientific supplements) and then brings in people (psychologists, sociologists, or historians) who have different perspectives on the technology and how it might impact humanity
      • “Then we have a conversation with the entrepreneur about the potential outcomes, utopian or dystopian, of the technology and how to steer it towards its best possible future”

What would Caterina’s billboard say?

  • “Be kind”

Random

These notes were edited by RoRoPa Editing Services

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