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

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Credit: Richard Morgenstein

“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 Fake

Caterina Fake (@caterina) is a long-time Silicon Valley pioneer. She is a co-founder of Yes VC, a pre-seed and seed-stage fund investing in ideas that elevate our collective humanity. Previously, she worked at Founder Collective as a founder partner, served as chair of Etsy, and was a co-founder of Flickr.

At Flickr, Caterina and her team introduced many of the innovations — newsfeeds, hashtags, “followers,” “likes” — that have become commonplace online. Caterina went on to found several more startups (FinderyHunch) and became an active investor, advisor, and board member, helping to build companies like Etsy and Kickstarter from their beginnings. (Other investments include Stack OverflowCloudera, and Blue Bottle Coffee.) Caterina is an early creator of online communities and a long-time advocate of the responsibility of entrepreneurs for the outcomes of their technologies.

Caterina sits on the board of Public Goods, the Sundance Institute, and McSweeney’s. She was given the Silicon Valley Visionaries award in 2018 and has received honorary doctorates from both the New School and the Rhode Island School of Design (RISD).

Caterina is also the host of the new podcast Should This Exist?, which asks the question, “What is technology doing to our humanity?” Should This Exist? can be listened to on Apple Podcasts, at shouldthisexist.com, or anywhere podcasts are found.

Please enjoy!

Listen to the episode on Apple Podcasts, Spotify, Stitcher, Overcast, Castbox, or on your favorite podcast platform.

#360: Caterina Fake — Lessons from Flickr, Kickstarter, Etsy, and Much More
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Want to hear an episode featuring another early Silicon Valley startup legend? — Listen to this episode featuring investor, Masters of Scale host, and LinkedIn co-founder Reid Hoffman, which features the 10 commandments of startup success. (Stream below or right-click here to download):

#248: The 10 Commandments of Startup Success with Reid Hoffman
Download


This podcast is brought to you by Athletic GreensI get asked all the time, “If you could only use one supplement, what would it be?” My answer is, inevitably, Athletic Greens. It is my all-in-one nutritional insurance. I recommended it in The 4-Hour Body and did not get paid to do so. As a listener of The Tim Ferriss Show, you’ll get a free 20-count travel pack (valued at $79) with your first order at athleticgreens.com/tim.


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QUESTION(S) OF THE DAY: What was your favorite quote or lesson from this episode? Please let me know in the comments.

Scroll below for links and show notes…

SELECTED LINKS FROM THE EPISODE

  • Connect with Caterina Fake:

 Should This Exist? Podcast | WebsiteTwitter | Instagram

Here’s the follow-up from Caterina with additional poetry and prose recommendations:

Some poets I mentioned on the podcast were Wallace Stevens and Emily Dickinson. Get their Collected Poems (The Collected Poems of Wallace Stevens | The Collected Poems of Emily Dickinson), and three great poems of Stevens’ are Arrival at the Waldorf, Emperor of Ice-Cream, and Thirteen Ways of Looking at a Blackbird. Greatest Hits is often a good way to get going.

There’s a lot of awful stuff out there. Even poets hate poetry. So stick to the well-trodden path when you’re just starting out. Get yourself an anthology and read as much as you can stand. But when you find something that moves you get some more. Go for The Norton Anthology of Modern and Contemporary Poetry (Volume 1 | Volume 2) or surf around Poets.org.

Some fiction recommendations: Growth of the Soil by Knut Hamsun. A Thousand Autumns of Jacob de Zoet by David Mitchell. Labyrinths by Jorge Luis Borges. The Tiger’s Wife by Tea Obreht

I read a ton of non-fiction too, but your prior guests have certainly recommended dozens of books everyone’s still getting caught up on, so I’ll refrain. But I was really taken with Svetlana Alexievich’s Book Voices from Chernobyl. Unbelievable.

SHOW NOTES

  • What are the unintentional consequences of having a real last name like “Fake?” [06:43]
  • How did Caterina wind up in Silicon Valley? [08:10]
  • What’s Caterina’s background, and what did she want to be when she grew up? [10:37]
  • How did Caterina leverage this atypical background as an advantage in the tech world of the mid-’90s? [12:00]
  • What did Caterina’s first year of working in tech look like? [13:58]
  • Flickr came about as a Hail Mary when an original project didn’t pan out. To what lucky break does she credit the successful pivot, and what other pivots did she witness at this time? [15:36]
  • How Caterina and her “Abraham” team at Flickr worked around the clock to build a solid community and company culture from the very beginning — before the idea of online community was repackaged and sold to the masses as social media. [21:35]
  • When looking at decisions, best practices, and informative mistakes made during these early days, Caterina isn’t above giving credit to lucky timing. [24:36]
  • Caterina talks about the solid foundation of human connection that attracted her investment in Kickstarter and Etsy. [28:30]
  • What has helped Caterina recognize anomalous patterns and “bet on the right horses,” so to speak? [31:05]
  • Caterina considers herself a night owl, but her approach to time management probably isn’t what you imagine. Here’s how she spends her most productive hours. [35:54]
  • Cognitive defense and the benefits of cultivating simplicity through time management. [43:36]
  • The most effective way Caterina cultivates this simplicity and overall productivity. [45:22]
  • What does Caterina get out of writing and reading poetry? [51:12]
  • Where might a novice find poetry that’s right for them? [57:15]
  • Does Caterina share the poetry she writes with other people, or is it strictly for her eyes only? [1:00:23]
  • What default routines help Caterina maintain structure with minimal decision-making effort? [1:02:29]
  • On accepting depression as part and parcel of the human experience without succumbing to the darker impulses it inspires. [1:05:50]
  • A Rumi resource for resisting the darkness. [1:13:10]
  • Memorable failures. [1:18:14]
  • Reading recommendations for people who want to cultivate a more constant optimism. [1:21:41]
  • What books does Caterina gift the most? [1:26:56]
  • What prompted Caterina to throw her hat into the podcasting ring with Should This Exist? and what can we expect from the format? [1:28:26]
  • What vigilance is required to ensure that emerging technologies are used for good rather than evil? [1:32:50]
  • Caterina gives us a peek into what we can expect from an upcoming Should This Exist? episode about gene-editing by CRISPR. [1:35:19]
  • What would Caterina’s billboard say? [1:39:50]
  • Parting thoughts. [1:41:41]

PEOPLE MENTIONED

Posted on: February 14, 2019.

Please check out Tribe of Mentors, my newest book, which shares short, tactical life advice from 100+ world-class performers. Many of the world's most famous entrepreneurs, athletes, investors, poker players, and artists are part of the book. The tips and strategies in Tribe of Mentors have already changed my life, and I hope the same for you. Click here for a sample chapter and full details. Roughly 90% of the guests have never appeared on my podcast.

Who was interviewed? Here's a very partial list: tech icons (founders of Facebook, Twitter, LinkedIn, Craigslist, Pinterest, Spotify, Salesforce, Dropbox, and more), Jimmy Fallon, Arianna Huffington, Brandon Stanton (Humans of New York), Lord Rabbi Jonathan Sacks, Ayaan Hirsi Ali, Ben Stiller, Maurice Ashley (first African-American Grandmaster of chess), Brené Brown (researcher and bestselling author), Rick Rubin (legendary music producer), Temple Grandin (animal behavior expert and autism activist), Franklin Leonard (The Black List), Dara Torres (12-time Olympic medalist in swimming), David Lynch (director), Kelly Slater (surfing legend), Bozoma Saint John (Beats/Apple/Uber), Lewis Cantley (famed cancer researcher), Maria Sharapova, Chris Anderson (curator of TED), Terry Crews, Greg Norman (golf icon), Vitalik Buterin (creator of Ethereum), and nearly 100 more. Check it all out by clicking here.

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17 comments on “Caterina Fake — The Outsider Who Built Giants (#360)

    • Finished the episode, epic. One of the most elevated conversations I’ve heard on the podcast. And great time management tips, as a small aside. Thanks so very much for the quality you always bring and for all the amazing leads and links to follow from this post.

      Like

  1. Still Here
    by Langston Hughes
    I been scared and battered.

    My hopes the wind done scattered.

    Snow has friz me,
    Sun has baked me,

    Looks like between ’em they done
    Tried to make me

    Stop laughin’, stop lovin’, stop livin’–
    But I don’t care!
    I’m still here!

    Liked by 1 person

  2. Hello Tim, I read from Nigeria, West Africa. I do a 9-5 work, I enjoy your blog and writings and working creating an outsourcing website in Nigeria were people leaving in Diaspora can send errands to their loved ones at home, I will like to know what you think of that.
    Thank you.

    Like

  3. Great interviews with a fantastic guest. Only: you didn’t ask a single question about her fund! I wanted to know more about what kinds of projects and entrepreneurs they fund, what pre-seed funding is, how much funding they typically provide, what they want to see in a pitch, how many ideas they’re likely to fund, etc. Not discussing anything about Yes.vc was a huge missed opportunity.

    Like

  4. A book talking about embracing the shadow without falling into the pit of despair
    Dark Nights of the Soul: A Guide to Finding Your Way Through Life’s Ordeals Hardcover – May 3, 2004
    by Thomas Moore

    Like

  5. Thank you Tim for this particular guest and conversation. Although I am not your ‘demographic’ (mid-50’s white woman!) I have listened to the majority of your podcasts and learned something from every one. This was particularly refreshing as you did not go down the tired path of ‘how you got to your place in a male dominated world’. She instead focused on her unique abilities that lead to her success and then to my surprise the conversation went even deeper. I wish we had more conversations like this going on. This is a must listen for my 20 year old daughter. Thank you!

    Liked by 1 person

  6. Thanks for a great episode. I really enjoyed the conversation about timing being the key component for many successful companies. Question is how to identify these parades that are about to happen.

    Like

  7. Thank you Caterina and Tim for a great conversation. A hallmark of the wise in the midst of great achievement, is a humble hat tip to some luck and timing along the way. I have to have a second listen with my notebook to hand!

    Like

  8. How “inner life” doesn’t have a place on the internet. Very meaningful to me in this age of FB. As a 70 year old woman still energetic and a dreamer

    Like

  9. Caterina is amazing! one of my favourite interviews, it’s so fresh and deep on so many points.
    I’d like to know what Caterina thinks about the latest Flickr development. It seems that unfortunately they have stepped far away from the initial beautiful goal that was set in the beginning after the latest acquisition. Such a pity…

    Like

  10. Reminds me of this words from the great bass player Victor Wooten about creativity and inspiration! 🙂

    [Moderator: YouTube link to video “Victor Wooten on creativity” removed.]

    Like

  11. Caterina was really fascinating to listen to…I greatly appreciated her sharing Darwin’s quote about his atrophied creative muscles. I had never heard of her before, either! Love the discussion on time management as well. Thank you for researching so well before interviews, Tim!

    Like

  12. The happiest day in 7 years story is quite compelling and uplifting, and I had a similar experience this past week on Valentine’s day, corny, I know, but the fact is that it’s true. The more I thought and pondered on the periphery of me, what I was experiencing inside was reaffirming my state of well-being. That the sun was shining and warming the bodies near me while I enjoyed coffee on an outdoor terrace, I was enjoying sharing this space in time with these other four strangers and that all these factors that we were sharing were synchronizing us for bliss, for delight (I can’t use the word happiness, it doesn’t set what was occurring). And I did ask myself: Why am I so full of bliss? I’m certain that it was more than 10 seconds that I wished these strangers bliss.

    Like