Kevin Systrom (@kevin) is an entrepreneur and the co-founder 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.

Please enjoy!

Intro [00:00]
The book Kevin gifted most frequently [01:16]
A book that helped Kevin in his early days [03:03]
Doing the simple thing first [04:02]
Instagram’s origin story [08:09]
How Kevin and Mike decided which features to keep or eliminate [09:42]
How filters became part of Instagram’s big picture [13:37]
Important lessons from Stanford’s Mayfield Fellows Program [15:16]
Insights from the Golden Personality Test [19:16]
How Mortimer Adler recommends reading nonfiction books [21:00]
A sampling of the kind of books currently occupying Kevin’s nightstand [23:08]
The precursor to Twitter (Odeo) and what Kevin did there [23:58]
Evan Williams’ superpowers [26:01]
Some of the most successful pivots in recent history [28:51]
Can you train to make the right call to pivot? [33:20]
How to get honest feedback [36:51]
Some honest feedback Kevin was grateful to get [38:44]
What is a 360 interview, and what can it teach us? [41:36]
Disallowing seven on a one-to-10 scale [44:29]
How Kevin has bounced back from tough times [45:46]
Selling Instagram for $1B—not everything you'd think it would be [51:06]
The power of understanding your own motivators [53:06]
How did Kevin learn to manage? [55:12]
On getting through decision-making bottlenecks [58:45]
How does Kevin choose the books he’s going to read? [1:04:17]
What Kevin gets most out of reading history books [1:06:14]
Some of my recommended biographies and histories [1:08:40]
Advice Kevin gives to entrepreneurs that very few actually take [1:10:09]
Other mistakes Kevin sees entrepreneurs and creators making [1:14:29]
What would Kevin’s billboard say? [1:16:58]
Parting thoughts [1:21:32]

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And for people who don't know Kevin, allow me to introduce Kevin.

Systrom, at Kevin, on Instagram, is an entrepreneur and co-founder of Instagram.

While at Instagram, Kevin served as the CEO, where he oversaw the company's vision and strategy and daily operations.

That is a whole lot, which we will talk about.

Under his leadership, Instagram grew to over 1 billion users, that's with a B, and launched dozens of products, including video, live, direct messaging, creative tools, stories, and IGTV.

The company also grew to more than 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 He currently lives in San Francisco with his wife and daughter.

So we've spent a little bit of time together.

We have a little bit of time, fortunately not 3 minutes on morning television to explore all sorts of things.

And I thought we could start with 1 since you seem to read not just why a widely, but intelligently and we'll hopefully get into that.

Are there any particular books that you have gifted often to other people?

I give kids books, but the 1 I give people that are trying to learn actively is Principles by Ray Dalio.

Gave me the PDF and I like skimmed over it.

And they were like, no, I seriously think you're going to love this.

And for some reason I didn't get around to it for maybe a year and a half.

And then I read the actual book and I was blown away.

It's both a guide to life, a guide to business, and also, I think, an insight into Ray and someone who's built an amazing business.

If you guys listening don't know what he does, he runs a hedge fund called Bridgewater.

And He's so much more than just a finance thinker.

So I give that a lot because I think it's a great guide to life.

And for those people who are wondering, just, just how many commas are involved in Bridgewater capital.

I think they have $160 billion under management, something along those lines a little bit.

And, he has a lot of very, in some respects, controversial and unusual practices within Bridgewater, like recording meetings and so on and allowing all employees to have access to the minutes and so on of such meetings.

Are there any other books that helped you in the early days from an entrepreneurial standpoint or that you found inspiring?

Early on, we read, Mike and I both read the Lean Startup, I think it's called Lean Startup Method or Lean Startup, can't remember.

I remember very early on, I went to 1 of his book talks.

I was 1 of 13 people sitting in this little room in Palo Alto.

And I was like a super fan, still am actually.

And so I don't know that I read the entire thing, but the principles from Lean Startup I still apply today.

1 of which is like do the simple thing first.

And that was our number 1 value at a, well, actually community first was our number 1 value at Instagram.

And still to this day, I come back to that.

So if I were reading 2 books, I'd probably read those 2 books.

And if we look at do the simple thing first, from a practical standpoint, could you give us an example?

And I love that you brought up Eric, because I remember also

But I remember I'm just going to start naming people he's a great guy.

I remember going also to, I think, some hotel conference room, probably in Palo Alto, when he was initially testing out the material that later became the book in these workshops.

Yeah, talking about avatars and all sorts of different things.

Doing the simple thing first, the scope of your responsibilities at Instagram, at least Reading even just your bio kind of makes my head spin to imagine what is involved and how easily distracted you could become What what are some examples or any examples of doing the simple thing first putting that into practice

Yeah, the first thing The first thing I'll say about doing the simple thing first is people love to make their lives more difficult than it needs to be.

It's like you talk to people who are saving for retirement and you don't have to go figure out a hedging strategy, right?

Like for currencies to save for retirement.

Turns out just like generally putting in a mutual fund is like not a bad idea.

And the returns you get for ever more complex strategies either in life or finance, they're like, it's harder to eke out the incremental value.

And I think what I found in a startup is when you're small and you're 2 people, it's me and Mike, we're coding late into the night.

Like you don't have time to make things complex.

And what ends up happening is you over optimize.

So you might think you know how it's going to break.

So you end up trying to build a bunch of things before it breaks And then it breaks in a different way.

And you're like, why did I spend all that time on that fix when actually I needed to be doing something else?

I think it's true in business, it's true in finance.

Early on, maybe the best example at Instagram was we were, here's the layman's term version, we were on 1 computer basically, 1 server, and we had enough space to store the data on that 1 server and Instagram became popular, right?

And it turns out all the data couldn't fit on 1 server anymore.

And we were like, this is a novel problem.

Let's figure out how to split it among 2 servers or 3 servers or 4.

And instead of just like writing a single file that said like, hey listen if your user ID is you know even you're on this server and if it's odd you're on that server, which would have sharded the data across 2 servers very well and deterministically.

1 ended up happening was we threw everything out.

We were like, you know what, let's adopt this crazy new technology that does auto sharding.

It was fancy and had all these bells and whistles.

I won't name it because I don't want to throw them under the bus.

But we spent, I don't know, 4 months trying to rewrite our system to be on this new database.

And eventually, after crashing a bunch of times and us having issues with it, we were about to run out of space, and Mike was like, screw it.

And he literally spent maybe 2 hours in the afternoon writing that file that we should have written to begin with, and it all just worked.

So I'm oversimplifying things a little bit for effect, but that's basically what happened.

And I still think about that story to this day in terms of an executive making a decision with his co-founder about what to do.

And it's amazing to me how many people think the quality of their management, they think is judged based on the complexity of their decisions or the outcomes.

And it turns out actually the right thing to do is sometimes the simplest and it's the most effective.

So I live that as a value both in life, finance, and at work as well.

So I'm going to rewind the clock a little bit because I think this segues.

Yes, we can and we can slice and dice, but this will be like watching the movie Memento.

It's basically usually what it's like when I do an interview.

I would love to talk about and we won't spend a ton of time on this because as we chatted before recording, I think you've talked about the origin story of Instagram a lot, but for people who don't have any context, I think it's worth diving into a little bit.

Doing the simple thing first makes me think of a common problem that I see in startups and in software development of any type really, which is feature creep.

And these products that start off with a focus, lose focus.

And it seems to me that you effectively did the opposite in some ways for the creation of Instagram.

Could you give people a little bit of background on how Instagram came to be?

And you can tackle that short version, medium sized, however you like.

Well, first of all, I'm happy to talk about where Instagram came from.

I just, it's such an interesting story in my life and that I've talked about it a bunch of times, but I forget that it's actually super interesting to hear for people who might've signed up for Instagram a couple years ago think it's been around forever, right?

But also I think it has some interesting lessons.

So I'll combine both talking about the origin story, but also how we kept it simple.

Instagram came out of 1, wanting to be my own boss.

And I remember telling at the time my mom, I was like, hey, I'm gonna go do this thing.

And she was like, what about health insurance?

I was like, oh, what about health insurance?

So my point is I was a little naive, but I wanted to do my own thing.

And I had a bunch of different ideas, 1 of which was a terrible idea for a check-in app.

Actually, it wasn't terrible, but at the time, there were a bunch of check-in apps and we're sitting in Austin right now, South by Southwest, you know, zoom back 678 years ago, it was all about Gowalla and 4 square, right?

So I had to have my version and it wasn't bad, but it wasn't good either.

Yeah, it was called Bourbon and B-U-R-B-N.

I still, I think I own the domain name somewhere, but anyway, what happened?

I left my job and I happened to be able to raise money for it.

And I'm not sure how or why, but checking apps were all the rage, so we raised some money.

It was a couple well-known firms in the valley.

And I had just enough money to work on it.

And I met my co-founder, Mike, at the time.

Cause I'm like, I'm technical, but not like, you know, I'm not a true engineer in the sense, like I didn't study it formally.

So I met Mike and he was 1 of the power users of bourbon.

And he was like, yeah, this will be super fun.

We worked on bourbon for maybe 3 months and it was clear.

And this is where keeping it simple comes in.

We actually got to the idea for Instagram by taking away features from bourbon, not by changing at all.

So a bunch of the features of bourbon, 1, you could check in at a place, but 2, you could add a photo of what you were doing at that place.

So you and I were out to drink somewhere.

I could post a photo of the beer I'm having or the cocktail or whatever.

And it turns out people kind of liked the check-ins.

They thought it was pretty lame because it was a me-too thing, but they loved showing people what they were doing.

They loved taking a picture of the bar, the restaurant, whatever.

And we realized to keep it simple, we were going to have to cut every other feature of bourbon, which we did.

Because we made a list and we asked ourselves what exists in the world?

Meaning, You look out in the world and you say, what opportunity is there to fill?

If stuff doesn't exist, and it's a problem that can be solved, AKA like the experience sucks, then that's what you should go do.

There were a lot of check-in apps, there were a lot of planners and meetup things and group chat things, But there was no solution for posting great photos to like lots of friends all at once.

So we made the list, we crossed off the things we thought were pretty boring, or just there was no opportunity in them.

And we circled the photos thing because we saw the confluence of both mobile phones being pervasive.

Like again, go back in the day, not everyone had an iPhone.

Like maybe the iPhone had been out for a couple of years at that point, 2007, 8, right?

So we knew that cameras were going to be pervasive in people's pockets, that people were gonna be carrying these camera phones, you know, wherever they went.

But we didn't know if it would be successful or not to capitalize on that.

But it was the only thing that looked like a greenfield opportunity.

So we got to the idea by cutting everything away from Bourbon, circling the 1 thing that we felt like was the biggest opportunity because it didn't exist yet, and it was a big need.

And we built the first version of Instagram.

Note, by the way, the first version of Instagram did not have filters.

And people forget the only reason Instagram worked early on was because of the filters.

And filters came about because I was on this walk with my wife.

I had been working on bourbon for a while.

And we were taking this walk along the beach and I was like, Oh, so you're excited about this new app we're building.

She was like, yeah, but I don't think I'm going to use it because my photos aren't that good.

It's like okay, well, why don't you think your photos are good and she's like well, all your friends, you know you post these amazing photos and they're all like filtered and stuff and I was like oh, that's because they use filters and she goes oh, well, you should probably add filters.

I went straight to the room and I just like got on my laptop and I made the first filter, which was X-Pro2.

This is a long way of saying, we cut features, we focused on what we thought the world needed.

And then we got to the heart of the issue of why people wouldn't use it because people didn't feel comfortable sharing their photos.

By solving those things right in a row and keeping it uber simple.

I mean, even that first filter could have been written in OpenGL and could have been a lot faster.

You tap on that filter, it took like 3 seconds to show you the filter.

Now, you mentioned Eric Ries, his book is as perhaps 1 of the influences.

I'd like to look at or dig for lessons learned, best practices observed, anything at all that you took away or very difficult times, anything from a few previous experiences.

So we'll go back to the Mayfield Fellows Program.

Was there anything in that program that you found particularly useful?

And then the next that I'll hit, so we could certainly do them in order or not, would be Odeo.

Okay, so biggest lessons- And What is the Mayfield Fellows Program?

Yeah, Mayfield Fellows Program, it's a program at Stanford where they take, I think they still take

a year, 12 typically graduate students, although I snuck in and I'll explain that in a second, who are interested in entrepreneurship and they focus on what is called an entrepreneurship education.

So they do 3 months of case studies, kind of like going to Harvard Business School, but case studies on just entrepreneurship.

Then 3 months you spend at a real startup getting real experience.

And then you come back and the last 3 months, so it's a year long program, meaning 3 quarters of the school year, you come back and you debrief on your own experience And you actually write basically a case on your experience over the summer.

My junior year, I snuck in by like, I don't know.

I basically, I was like, hey, but like I founded this startup, not really a startup.

It was a website at the time that was like a competitor to Craigslist, but for Stanford students only.

And I prayed that they would take me because I was so excited about entrepreneurship and they let me in.

Years later, by the way, 1 of the people who ran the program, still runs the program, actually pulled me aside and was like, just so you know, we were barely about to let you in.

And she was like, but the thing that made the difference was that you were out there actually trying to start something.

And I guess lesson number 1 is like, never expect you're gonna get a no, like always put your name in, right?

Number 2 is actually do the thing, like actually start the startup.

Don't just like write articles about start it, do something.

But that was the Mayfield Fellows Program.

And maybe the last lesson on the Mayfield Fellows Program that I got from it was, there's nothing in the world that can substitute for real experience.

If you want to be a chef, working in a kitchen is the only way you're going to learn going to culinary school, whatever I'm sure is great.

But working in a kitchen is the way to do it.

If you want to be gosh, like a like a tech founder, right?

You gotta know what it feels like to put it all on the line, lose everything and then come back, right?

You can't learn about investing unless you invest.

It's like real experience is so much better than what's in a book.

That doesn't mean that books aren't helpful, but

Yeah, very hard to become a professional soccer player by reading books on the physics of soccer.

Although I gotta tell you, I took this personality test and the results came back, but 1 of the main takeaways was like, prefers learning by reading.

And I was reading my results to my family because I thought it would be entertaining.

And my mom was like, Oh my God, like I remember when you were a kid, you just read everything.

And my dad was like, yeah, like you said you were going to be interested in playing baseball.

So I was like, I bought a mitt for you and we were gonna go play catch.

And you're like, dad, I gotta go to the library.

So I literally went to the library, read about how to pitch and then played.

The name of the personality test or the assessment that you did?

It's a variant on the Myers-Briggs test, but it actually gives you very specific breakdowns of every dimension.

So for those of you listening that don't know the Myers-Briggs test, there are basically 4 main dimensions of the personality test.

And it tells you, for instance, whether you're more casual or if you're like very calculated and punctual, that kind of stuff.

I wanted to know more about what I was like.

I spoke with him and he was saying, yeah, everyone who joins Bridgewater, we give this personality test.

And my co-founder took it, a bunch of our senior execs took it.

And it was illuminating to learn, see on paper what you know in the back of your mind.

And then of course it helps you work with others.

But a big part of it was reading on paper what you're actually like and realizing, for instance, I do learn by reading.

So I'm not someone who likes to sit in a lecture hall, I wanna have the book.

So if I'm gonna learn something new, like the way to learn is not for me to go to like a conference, it's to like sit down with the best book possible.

Like if you took it, maybe you like learning some other way.

He used to know some acronyms on reading.

And I had found in some of the research for this conversation a mention of Mortimer Adler's How to Read a Book.

How weird is it that I'm like so into reading that I have to find a book that's how to read?

Basically the idea behind this book is, it's how to read a book most effectively.

Most people open the first page and they start with the first word and then they go until either that they get bored or they push through or whatever.

And the claim in the book is basically that that is not correct.

That instead what you should do is familiarize yourself with the structure of the book first.

So the most important, I would say his thesis is that the most important part of reading a book is to actually read the table of contents and familiarize yourself with like the major structure of the book and then familiarize yourself by skimming the book and figure out what the main arguments are.

In fact, 1 of the secrets that I love and I still do to this day is most authors in the last paragraph of every chapter, especially the last paragraph of the book, will not only summarize their main arguments but make the points they actually have been waiting to make the entire chapter.

And by reading just those paragraphs, you get a pretty good idea of what the book's about.

Then you go back and you read like you normally read, but with the context of knowing the overall arc of the story rather than guessing where it's going to go.

I don't recommend doing this with a thriller because you'll ruin your experience.

But with nonfiction, I think it's fantastic.

And by the way, for those of you Mortimer fans out there, I probably didn't do it justice, but go buy the

Go buy the book, which will encourage you to buy yet more books.

I have this, seriously, if I could show you my room right now, my bedside table is just stacked with books.

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Kevin Systrom — Tactics, Books, and the Path to a Billion Users | The Tim Ferriss Show