Aug 17, 2017 ยท 15 minutes

In case you missed it, last month we launched the first of a six-part podcast series: “Beyond the Series B: How the Giants of Silicon Valley Made It.”  

We’re busy working on the final edits for episode number two: “Jumping off a cliff and assembling an airplane on the way down.”

Our first episode was about “luck”-- whether founders make their own luck, or are hostages to luck. We explored also when what seems like bad luck, turns out to be extremely good luck, and vice versa. We featured interviews with Elon Musk, Marc Andreessen, Reid Hoffman, Ann Miura-Ko, Brian Chesky, Brian Chesky, and Stewart Butterfield in this jam-packed 45 minute episode.

But believe it or not, that was just a fraction of the conversations in the Pando interview vault that wrestle with the topic of luck.

Here are the partial transcripts of a few of my other favorites that we just couldn’t quite fit.

From our interview with PayPal, Glow, and Affirm co-founder Max Levchin….

Sarah Lacy: Let's fast-forward to you moving to Silicon Valley. You were at University of Illinois. Netscape had come out of Mosaic during the time you were there for computer engineering. You knew you wanted to come to Silicon Valley.

Max Levchin: Yep. That was pretty awesome. That was probably the greatest luck I've ever had in my...That's actually not true. I've been crazy lucky a million different ways. I have to routinely thank whatever is watching over my particular luck.

One of the luckier things that has happened is I got accepted to University of Illinois. I really wanted to go to MIT. This is actually a funny story.

I was in high school. I went to a pretty crappy inter city high school in Chicago. This is continual entertainment at the expense of my naiveté and lack of English education. I went to my high school college center counselor. I said, "I really want to get into MTI. You have to get me into MTI."

She's like, "What the hell is MTI?" I said, "Massachusetts Technological Institute. It is great. It has the best computers." She's like, "OK, I'll try...It does not exist." I said, "What are you talking about? I read about it."

I went to this amazing show when I was a kid called Computers In The USA. It was actually in Kiev back in the Soviet days. It was basically just a giant promo for Apple. It was freaking amazing.

I went home and I was like, "Alright. The one thing I picked up from this is the really, really cutting-edge stuff happens at MIT." Except it was all translated and in Russian it was MTI.

I begged and pleaded to get me into MTI and finally, she was like, "I got nothing. MTI, I don't know but there's a thing called Illinois Institute of Technology." Which should have been my clue, but I was like, "IIT, MTI, no. OK."

She was like, "Well, that's the safety school for people who apply to University of Illinois at Urbana-Champaign." I was like, "Oh. What is that?" She was like, "It's a good computer science school. Maybe you could get in there. I don't know. Your English skills are pretty shitty, but your math is great."

To my great luck, I applied after the deadline and because this woman who at the time I thought was not on my side at all because she said, "Oh, crap. The application deadline has passed, we can't do this." [Then] she's like, "You could probably apply as an international student, they wouldn't be able to tell the difference because you're like...Your 'fro, your accent."

She applied for me as an international student. I got in and the cut-off was later. I got in by the skin of my teeth to U of I and got on campus a year or something later.

It was 1993, this is right after Mosaic 0.5 or 0.7 came out. As soon as I saw it I was just like, "Whoa. Oh, my God, the world is completely different."

I remember looking into a box outside. Champaign is very cold in the winter and very hot in the summer. It's very bright in the summer. It was the Quad Day, which is when all the student clubs bring out their wares and try to impress incoming freshman, try to get them into clubs.

The club I wanted to get into was Special Interest Group for Computer Science and Special Interest Group for Computer Graphics which is the graph part of ACM which is used for computing machinery, which I became super involved with and spent four years of college very, very happily connected to.

My first experience looking at Mosaic was actually looking into a big cardboard box, because it was so bright and the screens were so crappy that you really couldn't see anything unless you surrounded yourself with darkness.

I was peering into this box and I was like, "What is that? It's going like this." He was like, "That's Mosaic, NCSA makes it." Out of that, I met Marc and all the characters. That was super amazing. Then, by '97 when I was graduating, basically if you were a good student in computer science you were figuring out the cheapest apartments in Palo Alto.

That was it. I was like, "Just got to find a way." Between freshman and the time I actually got into a truck and drove to Palo Alto I had started and failed at four startups. I was full on startup material. I was like, "Just go to Palo Alto."


I’d argue that wasn’t Levchin’s luckiest break. He likely would have found a way to Palo Alto anyway in the dot com bubble. Few stories of entrepreneurial luck can compare to the time he almost lost his foot around the time of the Chernobyl disaster:

Max Levchin: [My mother] was one of the very first people in Kiev to see that food coming out of northern Ukraine was badly contaminated, bad in the fact that every fire brigade and every ambulance was just streaming out of the city going north the entire day and night after the accident.

Something big had happened, but the government was like, "Oh, nothing to see here. No worries. The Soviet Labor Day is coming up so get ready for the big parade!" It was a terrible idea because there was a big rain, and [it] was one of the very first acid rains.

Anyway, my parents figured out something happened. They stole me out of a hospital without getting doctor's permission. They threw me onto a train and sent me about 1,000 miles south to Crimea.

I got off a train and this is the cool story. By then, it's been 48 hours since the accident. By then the word spread. [There were] these makeshift Soviet police doctor ambulance type set ups that would screen people coming off the trains from the North. Parents were putting kids in trains saying, "Get the hell out, kid. Get the hell out of..." whatever the northern cities [they were in].

It was mid '80s in Soviet Union. No one had any freaking clue what this means, radiation. I grew up in a family of physicists. They were like, "Oh, shit. We're measuring these things in microfarad. That is not good."

I came off the train with my mom. There's a dude with big Geiger counter like a stick. He's literally going up and down. “Alright, it's cool. It's cool.” He got to me and like [beeping sounds]. Nobody seems to care except for my mom who was like, "Oh, no. Something is wrong."

This pantomime ensues where they keep on switching to a lower resolution, because the thing is beeping too frequently, which means it's picking up too many particles per second. At some point the guy with the stick goes, "It's in his leg and we maybe have to cut it." This is one of these things I probably would never forget.

My mom to her great credit said, "Try it again with his shoes off." It turned out that I stepped on a rose thorn while I was escaping the hospital. The rose thorn managed to pick up enough of the acid rain fall-out to trigger a radioactivity.

Anyway, it was pretty terrifying, but it was definitely one of these bright childhood memories where I almost lost my leg to a crazy guy with a Geiger counter. I don't think anybody else has one of those…


Here’s a less dramatic, more common story from our interview with AngelList’s Naval Ravikant. I laughed re-reading this transcript at the real talk about just how hard it is to succeed and how anyone who complains about it should cram it…

Naval Ravikant: One of the things I don't like about this whole culture here is, what makes Silicon Valley great is it's a meritocracy, and I almost feel like a schmuck sitting up here talking to you because I think you guys have just as many interesting things to say back to me.

I've failed more than I've succeeded. Everyone's journey is unique and interesting, and it is a meritocracy, and there is a lot of luck involved too. Some people win and they get to sit up on the stage and talk about how they're photo uploading app got sold for a billion dollars and yours went out of business.

[Instagram’s Kevin Systrom] did an amazing job and he did incredibly hard things. Not to take away anything from him, but there were a dozen guys who came before him who did incredibly hard things in the same space whose timing was just pre-iPhone, and there are a dozen people who will come later and do innovations, because they're post Instagram they don't get that same outcome.

Timing matters an enormous amount. Who you work with...If you were PayPal in the early days and ended up in the PayPal Mafia you did incredibly well. There is a lot of luck involved whole system.

Sarah Lacy: How do you feel about where luck ends and begins, and where skill ends and begins? I think this is something people have a lot of angst over in the Valley, and I think they have angst if they've failed, but they have more angst if they've succeeded.

NR: Success doesn't bring that much angst. That sounds like something successful people say to make it sound like their lives are hard.

SL: You know people who've sold their company for a lot of money, and then they go into this pit of depression. Look, you don’t have to feel sorry for them, but it's very real thing.

NR: They need to be slapped upside the head. That's just idiotic. There is no question that you are better off than you were before you sold the company for a zillion dollars.

You are in a plateau, optimal situation, and if you don't believe that then give your money away, trade it off to somebody else. I reject those viewpoints that fly in the face of common sense. We are here to succeed, and if you succeed, you've won, and it's great, and you should enjoy it. If it makes you more miserable then there is something deeply, deeply wrong with you.

SL: When you say you're here to succeed, what do you mean by that? Is it about money? What is the goal for you?

NR: Money, for a lot of people, ends up being their score card. I was at an event before speaking at Berkeley, and there were about 300 people in the room.

A lot of them were mentors, and entrepreneurs, and investors, and some very successful people. I said, "How many of you in this room have started a company?" A lot of hands go up. Then, "How many of you have sold a company?" Some of the hands go down.

"How many of you have sold it, and it was a profitable outcome. You made some money?" Some more hands go down. "How many of you built a product that was unique and new? You weren't just doing a variation of what already existed, but it was genuinely new?" More hands go down.

"How many of you managed to actually sell that product to customers, to end users, and get them to pay for it?" More hands go down. "In volume?" Nobody. The reality is that the history of Silicon Valley is maybe every decade 20 or 30 new great products get created, and the rest of us ride off their coat tails.

Including me for most of my career. We get lucky and we sell our companies to them, or we get unlucky and we don't.

SL: Or invest in them.

NR: Or we invest in them, or we get a job in those companies.

SL: Underwrite the right IPO.

NR: Or we underwrite the right IPO or whatever it is, but the set of actual things that are truly creative is very small. That is the ultimate goal.

That's why people look up to Elon Musk and Steve Jobs and Mark Zuckerberg, because they managed to create something brand-new, that did not exist before and spread it to the world in volume and get paid for it. It's a very, very, very hard thing.


Lastly, one of the greatest stories of serendipity, from our interview with Dustin Moskovitz, Facebook and Asana co-founder. His life could have been far different if he had wound up with a different freshman year roommate…


Sarah Lacy: How did you and Mark meet?

Dustin Moskovitz: This is an interesting story. Mark and I were pseudo-randomly paired together as roommates. Basically, what happened is when you're a freshman at Harvard, you're in the freshman dorms. You enter the lottery system to choose your house for the next three years. It's a big deal.

I ended up just choosing to block with my girlfriend at the time. She had a group of friends that she was blocking with. Sorry, my memory is actually a little faulty on this. I think what happened is I was in one blocking group and Mark was in another.

Basically, Billy, one of our roommates that doesn't often come up in the story, he was rooming with me. Chris Hughes was with Mark. They put us into a four-room suite. That's basically how we met. I literally met Mark the first day of sophomore year. The rest was just fate.

SL: What did you think of him when you first met him?

DM: When I first met him. He was definitely an interesting character. He had a ton of energy. It was the first day of school so he was really excited, of course.

One of the things that stands out in my mind, and actually, I think is the way David Kirkpatrick decided to open "The Facebook Effect," is the story about how he had this giant whiteboard with him, that I think was in his parents' van and was the very first thing he moved into the suite.

It must have been 4x10 feet or something like that in a very small college suite. We had a hallway connecting our bedrooms. This was the whole hallway.

We hit it off right away. He's very personable and easy to get along with. Yeah, it started off an exciting year.

SL: In the early days, when you guys first started working on this thing, were you thinking, "As soon as I get out of Harvard, I want to start a company?" Were you on that entrepreneur path?

Was it something you thought about? Or did it just happen?

DM: No. I don't think that would be an accurate way to describe me. I was on the business track in school. I was actually in Econ concentrator at Harvard. I was also involved in a lot of technology. I built some websites in high school. I always fantasized of something along the lines of being the business side of a technology company.

I don't think I ever really pictured it as founding a company, being the entrepreneur. That wasn't really in my mindset. It was much less popular at the time, in general. A lot less of that community was around.

I will say that was definitely the way Mark thought about things. He always had a couple of projects going on the side. Made quite a bit of money in high school, even doing large websites and things like that.

SL: Every time I've talked to you, going back to, I think around the Greylock/David Sze $500 million valuation deal, you've always been a big believer that Facebook would be a big company. Even when other people in the company were, "Jesus, there's no way in hell David Sze is ever going to get that money back."

How far back did that go?

DM: I think my belief was always quite large, but it got bigger over time. I was always one or two years ahead of everyone else. The first week of Facebook at Harvard was really quite incredible. It was just complete ubiquity, literally on every screen as you walked around. That gave me a lot of confidence and put the big idea in my head.

There's a passage in “The Facebook Effect” about Mark and I negotiating my compensation. I very distinctly remember saying something along the lines of, "I think if you give me one percent of this company, that would probably end up being well more than enough, but it wouldn't quite feel fair." We ended up coming up with something else.

I think that speaks to how I was valuing the company at day five.


A lot of this episode centers on how certain founders have exploited their “luck.” To take the most serendipitous example of the three, it’s easy to say if you’d been Mark Zuckerberg’s dorm-mate, you would be a billionaire today too. But it took a massive leap of faith for Moskovitz to leave Harvard and go-all-in on Facebook well before the consumer Internet was back and unicorns roamed the Valley.

Hear more of our examination of good luck, bad luck, and making your own luck on our podcast. Episode two is coming soon!