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

“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 (Findery, Hunch) and became an active investor, advisor, and board member, helping to build companies like Etsy and Kickstarter from their beginnings. (Other investments include Stack Overflow, Cloudera, 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.

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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):

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 | Website | Twitter | Instagram

• Should This Exist? Podcast
• South by Southwest
• Stanford MBA
• Rock Climbing in Arkansas 101: Outdoor, Indoor, and Gear, Fayettechill
• Nepal Rock Climbing, Mountain Project
• U.S. Begins Privatizing Internet’s Operations by Peter H. Lewis, The New York Times
• Vassar College
• Renaissance and Early Modern Studies, UC Berkeley
• Making Sense of Multimedia Gulch by George Raine, SFGate
• HTML Tutorial: Learn HTML for Free, Codecademy
• Flickr
• Game Neverending, Codex Gamicus
• The Hail Mary Prayer, Loyola Press
• The Obvious Corp. Takes Backseat as Ev Williams, Biz Stone, and Jason Goldman Shift Focus to Individual Startups by Colleen Taylor, TechCrunch
• Twitter
• Google Buys Blogger Web Service by Neil McIntosh, The Guardian
• Amazon Web Services (AWS)
• Killing the Abraham by Caterina Fake, Wired
• The Bible
• SmugMug
• Airbnb
• Friendster
• Idealab
• Yes VC
• Kickstarter
• Etsy
• Souk of Aleppo, World Monuments Fund
• Oh the Agony! 150 of 165 Invited Investors Did Not Respond to Uber Investment Offer in 2010 by JD Alois, Crowdfund Insider
• Founder Collective
• The Innovator’s Dilemma: When New Technologies Cause Great Firms to Fail by Clayton M. Christensen
• How Buildings Learn: What Happens After They’re Built by Stewart Brand
• The Anthrobscene by Caterina Fake, Caterina.net
• Long Now Foundation
• The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich by Timothy Ferriss
• The 4 Hour Body: An Uncommon Guide to Rapid Fat Loss, Incredible Sex and Becoming Superhuman by Timothy Ferriss
• How to Modify Your Sleep Schedule for Maximum Efficiency by Caterina Fake, Bloomberg Businessweek
• The Genius Neuroscientist Who Might Hold the Key to True AI by Shaun Raviv, Wired
• Flow: The Psychology of Optimal Experience by Mihaly Csikszentmihalyi
• Public Goods
• DF Tube (Distraction Free for YouTube) for Chrome
• Apple Screen Time
• The Freewheelin’ Bob Dylan by Bob Dylan
• How Can I Be as Great as Bill Gates, Steve Jobs, Elon Musk or Sir Richard Branson?, Quora
• PayPal
• Tesla
• The Science of FOMO and What We’re Really Missing Out On by Nick Hobson, Psychology Today
• Eletelephony by Laura Elizabeth Richards
• The Good Order by David Brooks, The New York Times
• Social Peacocking and the Shadow by Caterina Fake, Caterina.net
• The Child and the Shadow by Ursula K. Le Guin
• Sonnet 29: When, in Disgrace with Fortune and Men’s Eyes by William Shakespeare, Poetry Foundation
• Cry Out in Your Weakness by Rumi, Zen of Water
• Humans of New York
• Labyrinths by Jorge Luis Borges
• Caterina at Goodreads
• The Odyssey by Homer with Emily Wilson
• A Tomb for Boris Davidovich by Danilo Kis
• Hannah Versus the Tree by Leland de la Durantaye
• Ethan Frome by Edith Wharton
• The White Goddess: A Historical Grammar of Poetic Myth by Robert Graves
• The Upanishads
• The Emigrants by W.G. Sebald
• Drawings and Observations by Louise Bourgeois
• The Principles of Uncertainty by Maira Kalman
• Letters of Note: An Eclectic Collection of Correspondence Deserving of a Wider Audience by Shaun Usher
• Masters of Scale
• CRISPR: A Game-Changing Genetic Engineering Technique by Ekaterina Pak, Harvard Medical School
• Fleurs du Mal/Flowers of Evil by Charles Baudelaire, FleursDuMal.org
• Frankenstein by Mary Wollstonecraft Shelley
• Fire and Ice by Robert Frost, Poetry Foundation
• Whole Earth Catalog
• The Woolly Mammoth Revival, Revive & Restore

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

• Ev Williams
• George Oates
• Brian Chesky
• Joe Gebbia
• Bill Gross
• Perry Chen
• Yancey Strickler
• Sunny Bates
• Reid Hoffman
• Stewart Brand
• Bob Dylan
• Steve Jobs
• Elon Musk
• Justine Musk
• Kathy Sierra
• Wallace Stevens
• William Shakespeare
• Emily Dickinson
• James Merrill
• W.H. Auden
• Charles Darwin
• Albert Einstein
• Carl Jung
• Ursula Le Guin
• Fred Rogers
• Hafez
• Jalal al-Din Rumi
• Brandon Stanton
• Seneca
• Jorge Luis Borges
• Paul Celan
• Natalie Shapero
• Brenda Shaughnessy
• Kahlil Gibran
• Homer
• Emily Wilson
• Danilo Kis
• Leland de la Durantaye
• Edith Wharton
• Robert Graves
• W.G. Sebald
• Louise Bourgeois
• Maira Kalman
• June Cohen
• James Bond
• Charles Baudelaire
• Victor Frankenstein
• Prometheus
• Robert Frost

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