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

“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.

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


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…


  • Connect with Kevin Systrom:



  • 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]