Kevin Systrom — Tactics, Books, and the Path to a Billion Users (#369)

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“I think a big part of knowing that you’re right is working as hard as you can to prove that you’re wrong. And if you can’t, well, there’s only one option left, which is: you’re probably right.”
— Kevin Systrom

Kevin Systrom (@kevin) is an entrepreneur and the co-founder (with Mike Krieger) of Instagram. While at Instagram, Kevin served as the CEO, where he oversaw the company’s vision and strategy and daily operations. Under his leadership, Instagram grew to over one billion users and launched dozens of products including video, live, direct messaging, creative tools, Stories, and IGTV.

The company also grew to over 800 employees with a campus in Menlo Park, new offices in New York City, and a new headquarters in San Francisco.

Prior to founding Instagram, Kevin graduated from Stanford University with a BS in management science and engineering. Kevin currently lives in San Francisco with his wife and daughter.

Watch the interview on YouTube.

You can find the transcript of this episode here. Transcripts of all episodes can be found here.

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

#369: Kevin Systrom — Tactics, Books, and the Path to a Billion Users
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Want to hear an episode with someone else who lives by strong principles? — Listen to my conversation with Ray Dalio. We discuss how Ray thinks about investment decisions, the three books he would give to every graduating high school or college senior, how he might assess cryptocurrency, and much, much more (stream below or right-click here to download):


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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 Kevin Systrom:

Instagram

SHOW NOTES

  • The book Kevin has been gifting most frequently. [04:34]
  • Another book that helped Kevin in his early days of entrepreneurship that drove home the importance of doing the simple thing first. [06:31]
  • How has Kevin implemented the idea of doing the simple thing first in his own operations, and why is it so important? [08:03]
  • Instagram’s origin story as a check-in app called Burbn, and how Kevin and his co-founder Mike kept things simple even when it became clear they’d have to pivot their business model into something else. [11:56]
  • In the transition from Burbn to what would become Instagram, how did Kevin and Mike decide which features to keep and which ones to eliminate? [15:41]
  • How filters became part of Instagram’s big picture. [17:19]
  • What is Stanford’s Mayfield Fellows Program, what was the deciding factor that granted Kevin access to this exclusive curriculum, and what were the most important lessons he learned from the experience? [19:28]
  • What Kevin confirmed about his learning style from the Golden Personality Test that Ray Dalio has people take at Bridgewater. [22:07]
  • How Mortimer Adler recommends reading nonfiction books most effectively. [24:29]
  • A sampling of the kind of books currently occupying Kevin’s nightstand. [26:38]
  • What was Odeo, and what did Kevin learn during his internship there? [27:27]
  • From the time they worked together at Odeo, what does Kevin see as Evan Williams’ superpowers? [29:31]
  • An examination of some of the most successful pivots in recent history and why some entrepreneurs handle the process better than others. [32:44]
  • Is the ability to make the right call between pivoting or stopping a project altogether intrinsic, or something that can be trained? [36:50]
  • Someone needs to write a 10-volume set about the bad ideas of amazing people. It could be called There Is No Midas Touch. [38:10]
  • Approaches for getting honest feedback when it’s time to stress test — especially when people are wired to avoid conflict and might not want to hurt your feelings. [40:21]
  • Some honest — but difficult to acquire — feedback Kevin was grateful to get during his early days of stage presentation that helped him improve. [42:56]
  • Learning how to take honest feedback non-defensively may be the key to giving honest feedback without fear. [44:37]
  • What is a 360 interview, and what can it teach us? [45:12]
  • Disallowing seven on a one-to-10 scale when soliciting feedback is a good way to prompt honesty. [47:59]
  • Tough times Kevin has experienced on his entrepreneurial journey and how he’s bounced back. [49:16]
  • Selling Instagram for a billion dollars should have felt like winning, but Kevin explains why it was bittersweet at the time and how he responded to it all. [53:48]
  • The power of understanding your own motivators and what gets you out of bed in the morning, and how Kevin discovered he’s not actually as competitive as he’d always assumed. [57:42]
  • How did Kevin learn to manage, and why does he strongly support the idea of hiring up? [58:44]
  • Mr. Systrom elaborates on the meetings he and Mike would have specifically to get through decision-making bottlenecks and how this was inspired by Herbie from The Goal. [1:02:17]
  • How does Kevin choose the books he’s going to read? [1:07:42]
  • What Kevin gets most out of reading history books. [1:09:46]
  • Some of my recommended biographies and histories. [1:12:12]
  • Advice Kevin gives to entrepreneurs (and I give to aspiring authors) — that very few actually take. [1:13:41]
  • Other mistakes Kevin sees entrepreneurs and creators making often. [1:18:01]
  • What would Kevin’s billboard say? [1:20:29]
  • Parting thoughts. [1:22:43]

PEOPLE MENTIONED

Posted on: April 25, 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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13 comments on “Kevin Systrom — Tactics, Books, and the Path to a Billion Users (#369)

  1. Concerning ALC… Well I personally would willfully change the darkness with your dreams. That is what I do. ALC just brings out what is there hiding.

    My best!

    David

    Like

  2. Fine, fine, fine…I’m going to follow your step-by-step instructions on how to write a best seller about how to break addiction!

    Like

  3. Regarding your now-abandoned ALC experiment, be very careful with cholinergic compounds. My Ph.D. project was based on inhibiting acetylcholinesterase, the enzyme responsible for breaking down the neurotransmitter, acetylcholine, in the brain. Inhibit the enzyme too well and the build up of the neurotransmitter will cause all sorts of havoc. But on the flip side people with Alzheimer’s disease have an acetylcholine deficiency (meaning the enzyme works too well). The concentration of acetylcholine in the brain at any given moment must be delicately balanced.

    Like

  4. I don’t know nearly as much about cholinergic system as other commentors but in my experience the only nootropic which I (and a few people from longecity) had serious physical side effects from was alpha-GPC which is an acetylcholine precursor.

    Like

  5. Hey Tim,
    What led you to your ALC experiment? For me, it was after reading Dr. Amen’s book. I have been taking it for awhile and have not had the same reaction as you. However, after reading some of the comments I think I will stop. Also, what are your thoughts on phosphatidyl choline and vincpocetine supplements for cognitive enhancement?

    Thanks for all the awesome things you do!

    Like

  6. Hey Tim, love the podcast. I thought you’d like to know that General Stanley McChrystal recently released a new book about leadership. Last week he discussed it on the Spycast podcast. He may be open to doing your podcast. I’ve read that he eats only 1 meal a day and sleeps only 4 hours a night. It would be very interesting to know how he maintains such self discipline. Thanks.

    Like

  7. Voice bits in my head from this podcast: ::Ideas are just that unless you Solve problems with your idea :: Weigh feedback wisely :: Do the math before setting your passion as your career with noise cancellers :: Intrinsic motivator ::

    You may do what you want with my feedback (wink wink) however, i feel uncomfortable watching you Tim and all your guests holding the microphone for that long, especially on those chairs and that room, perhaps a cozy setting would put my highly altruistic nature at peace. I got hooked to your shows when they were shot at your home (?) they were relaxed and were in sync to the genuineness you want to project.

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  8. Was Palahniuk religious? I never thought he was. Profound but not religious. The quote is very Christian. It embodies the Gospels in a nutshell. In addition it’s Kabbalistic in that it suggests God needs mans help to achieve Oneness or perfection. Tough to explain in a few words. But according to the Kabbalah as I learned it from Yalhak (recently deceased JewishAmerican scholarprophet) during the Big Bang or the Shattering of the Vessels God lost his oneness and is striving thru humanity to regain his Unity or Oneness. As a amateur student of religion this immediately caught my eye. Cheers, Tony

    Like

  9. My favorite take from this episode was How to Read a Book. This book is a must for any age. Wish I had read this before high school.

    I would love to hear Lauren Bath aka Australia’s First Professional Instagrammer as a guest.

    Like