Please enjoy this transcript of another episode of the “Books I’ve Loved” series, in which I invite amazing past guests, close friends, and new faces to share their favorite books—the books that have influenced them, changed them, and transformed them for the better.
Cindy is a billion-dollar dealmaker, self-made entrepreneur, and tireless force of nature if you’re asking Fortune magazine. Prior to forming The Pink Ceiling (affectionately known as the Pinkbuator) to fund and foster female-led disruption in healthcare, Cindy built two pharmaceutical companies from scratch. As Founder and CEO of Sprout Pharmaceuticals, she created a new category of sexual wellness for women by taking on the FDA and winning the approval of the first and only pill for women’s libido, Addyi. Cindy sold that company for $1B and now invests in game-changing ideas that support her mission to put women on top.
Alexis is the co-founder of Reddit and Initialized Capital and the author of the bestselling book, Without Their Permission. Alexis has long advocated for the open internet, STEM education, and paid family leave. Alongside Garry Tan, he co-founded Initialized Capital—a seed-stage venture fund with over $500M under management and a portfolio with $36B in market value so far. After selling Reddit to Conde Nast, Alexis returned in 2014 as executive chairman to help lead the turnaround of the now independent company, which was last valued at $3B.
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Cindy Eckert: Hi, I’m Cindy Eckert, and I’m an entrepreneur who’s built and sold two successful pharmaceutical companies. I’m perhaps best known for my last, Sprout Pharmaceuticals, that broke through with the first and only FDA approved pill for women’s low libido. That’s right, I said low libido. I sold that business for a cool billion dollars up front and went on to put my money where my mouth is. So today I invest in other disruptive female founders and disruptive technologies in health inside of my Pinkubator. That’s right. I said pink. I had a little pink pill. I love pink, but perhaps the biggest twist and turn of my unconventional story is that the company that I sold for $1 billion, well, I got it back for nothing last year. So how does that happen? I fought to get it back, because the company I had sold it to never launched it, and that was not going to happen on my watch when we’d won one for women. Guys have had 26 options, I thought it was about damn time that women had one of their own.
So we went after getting it back. And I’m delighted to say we were successful in doing that and that the shareholders kept the billion. So now I’m on a mission to launch Addyi as well as many other firsts for women. But, I should say, of all the career highlights, maybe one of the top ones is being interviewed by Tim Ferris. So when he called and said, “All right Cindy, what are books you love?” I got to thinking, the first one that came to mind, no-brainer for me. Purple Cow by Seth Godin. It is such a good book. So what’s it about? Well, it’s right there in the title for you. There are tons of brown cows out there, but it takes a purple cow to grab your attention. And his book is a marketing book. It talks about the model of marketing. It talked about how the old model of marketing was the huge companies with giant budgets.
You’ve got to have the Superbowl ads—like, they were going to win. They were going to win through money and exposure, and how that model really has been disrupted and that we have these remarkable brands that attract remarkable to them. That’s the purple cow philosophy. So as I was reading it in the context of marketing, it really struck me, but isn’t that a philosophy with which to build a business? So I said I’ve built two companies. Dial back to my first one, Slate. And really purple cow, from a philosophical standpoint, the standing out in a sea of sameness, was so fundamental to the core of what I was trying to accomplish, that literally, if you go back and look at email signatures for people, instead of saying best regards, cheers, whatever your sign off is, many times, when you look at my original team that worked with me, the sign off is “moo.” Moo, because I talked about it so damn much, the purple cow philosophy.
How are we going to go out there and stand out in a sea of sameness? I’ve been in big environments. I was in those big environments, and I was successful, but totally uninspired. I was in environments that believed the only way to be successful was to homogenize, was to make us all brown cows, and we had to follow the certain way. And really the hunch was, when I started Slate, wait a minute, there are other people out there just like me. They’re in those environments. They are successful, because of their own drive and determination, but they’re not inspired, and they’re actually not tapping into this purple cow aspect of them that will make you remarkable. And so I hired against it. I fired against it. I incentivized, we dressed up at Halloween. Some of my employees came in dressed as purple cows. I mean, we really got it, because if you come into my office—let’s just say hiring, for example—by the time somebody gets to my desk and has been vetted by my team, they’re abundantly qualified to have the job.
What I was looking for was purple cow characteristics. How did they stand out from everyone else? How were they remarkable in a way that was going to attract remarkable to them? And so those were really what I was torturing. Purple Cow, I believe is an outstanding read for everybody. Not only if you’re in marketing and you want to understand how the old rules don’t apply anymore, but really philosophically for how you embrace how you show up in this world. You know, I show up in pink, hot pink, to be exact, and that was born out of a reference, if I’m being quite honest, because people would pat me on the shoulder when I was trying to get the first ever pink pill approved for women. And the pink became a symbol, if you will, of what I was fighting for. I like pink, by the way.
I’ve always liked pink. I look back at childhood photos, I’m almost always in pink. And that was the signal to mean that you have to show up, really loudly, exactly as you are. And I will say though, despite my best efforts, Seth Godin has still not released the Pink Cow, but I’m counting on that coming out maybe 2020, Seth. I don’t know. Let’s look at it. So love Purple Cow, highly recommended.
Let’s talk about another book that I love, and Tim and I haven’t talked about it before, but I’ll bet you this one is on his list too, and that is A Curious Mind by Brian Grazer. And if you don’t know his name, I got to tell you, you definitely know his award-winning movies. I mean he’s worked with Tom Hanks on so many projects. He’s partnered with Ron Howard, these little names. And he’s had all of these—40 plus, I think, Academy Awards, he has won.
And A Curious Mind is about this one thing that has the ability to connect us all. And that is curiosity. And I cannot agree more enthusiastically with that concept, because if I think about all of the successful people I’ve had the privilege to meet over the years, I do feel like that’s it. They are wired with curiosity to the core. And in his book, Brian, in a curious mind, he talks about, really, techniques in which you can cultivate your own curiosity. So he gives very practical tips. But one of his is that he schedules a curiosity conversation with somebody he doesn’t know, who’s outside of his own discipline, and he really sits down. As a discipline, on his calendar, he puts aside time really for a curiosity endeavor, because he knows that when he sits down and learns from others, he can apply that to what he’s doing.
And I think that’s it. The hallmark of the best, and most successful entrepreneurs is that they are almost insatiably curious. It allows them the ability to not only be constantly learning and applying those new lessons, but open-minded enough to be able to do that. Because I got to tell you, it is not a straight line to success, and if you’re not open-minded enough to listen, and make the turn slightly to the left or slightly to the right, you’ll never get there. It inspired in me a lot of thinking about, why did I become an entrepreneur and what laid the foundation for that, maybe very early on in a way that I wasn’t even conscious of. And what I think in that regard is my parents cultivated my curiosity. And I have two big brothers, we laugh about this, we share this story and this is when we were little, and we would go to our parents for help with homework.
You know you want the leg up, you want the quick fix and the answer, regardless of the question. It could have been a math question, it could be an English question. When we asked them the question, they would reply with the same four words. And they were, “What do you think?” It was infuriating, by the way, at the time in which you just wanted the assist from your parents, make it a little bit simpler, but really what they were doing, and I give them a lot of credit for this—I think sometimes they genuinely were just tired—but I think at the core of it, the “What do you think?” was cultivating curiosity, and that curiosity showed up in this way. So if they weren’t going to give me the answer, I was going to have to be willing to go and ask others and get their point of view.
I was going to have to develop my own point of view and independent thinking along the way. And all of that cultivation of the approach of constant learning, the approach of forming your own opinions, the approach of realizing that it’s not going to be handed to you by someone all knowing above who’s going to pass down the perfect answer really is foundationally so very helpful to me as I’ve gone through my career, as I have built businesses from scratch, as I have sold them. The curiosity is what has kept me showing up for more. So if I’m thinking about two books that I truly love, and I couldn’t recommend them more highly, it would be Purple Cow from Seth Godin. For all of you listening, I hope you always show up as the purple cow and separate yourselves in the sea of sameness. Let’s be honest, there is a lot out there today. We get a lot of messages coming at us fast and furious. You got to stand out. And really the simplest way to stand out is to be authentically you. That separates you from everybody else.
And A Curious Mind by Brian Grazer. The curiosity factor is the difference between good and great. It will be the recipe in my mind for the most successful and, frankly, fulfilling life. Do yourself a favor and have a curiosity conversation. Put it on your calendar if that’s how you roll or just open up your mind to the thought that mentors don’t come just looking up. Mentors come to your left and your right every single day, and you should be challenging yourself to learn from them. Thanks so much for having me, Tim.
Alexis Ohanian: This is Alexis Ohanian, bestselling author, co-founder of Initialized Capital, an early stage venture firm, and Reddit. But today I’m here to talk about books I love, and shout out to my buddy Tim Ferriss for this really great idea and for inviting me to talk about it.
I have two books that I want to talk about today. One made a pretty big impact on my life at a pivotal moment. The other I just recently read and have been obsessed, obsessed with. First, Masters of Doom by David Kushner. Now, this book is about the founding story of id Software, and if you were like me, grew up playing video games, this company invented the genre of the first person shooter with a game called Wolfenstein 3D. And it was pretty special. I played a lot of video games as a kid and most of them were made by id.
But this book came into my life at a really important time because I was a student at the University of Virginia. I was actually on my way to becoming a lawyer. I had majored in history and business, and like any good history major was taking the LSAT. When I walked out, I walked out of that LSAT and I walked into a Waffle House because I was hungry. That was it. I just really wanted a waffle, and eating that waffle, I realized if I chose breakfast over the LSAT, I probably should not be a lawyer. So I went home and I started thinking about what I was going to do with my life since it obviously wasn’t the law. And this book, Masters of Doom had recently been recommended to me, and I dug in and found myself hearing the story of John Carmack and John Romero, the two founders of id and how they built this business, eating pizza, staying up late, writing code, and doing something they genuinely loved, and that somehow managed to be a video game empire. Really shaped an entire industry to this day. I mean, if you’re playing Call of Duty or Battlefield, you’re playing a game that is a sort of a relative, a great, great grandson or daughter of Wolfenstein 3D, which was the—really the first first-person shooter.
And so here were some random dudes, not unlike me and my co-founder who built something that changed an entire industry. That really crystallized for me what some really passionate founders who could write some code could do to change things, and this gave me the confidence to say, “You know what? They can do this. We can definitely do this.” And I convinced my roommate to start a company with me, and that company was called My Mobile Menu, MMM for short. It would let people skip lines by ordering food from their phones, but it was 2004, 2005, so there were no smart phones and it was a terrible idea. It was ahead of its time, and thankfully we got convinced to not pursue that idea by Y Combinator and instead started another company called Reddit.
So without a doubt, Reddit would not exist if it weren’t for Masters of Doom. Well, and also Waffle House, so thank you, Waffle House, but I can think of no better place to read Masters of Doom than your local Waffle House. There you go. That really just… it changed my life in so many ways and at the time felt so insignificant. It was just the right book at the right time, and I’ve gotten the chance to actually thank the author, David, for writing it because, really, Reddit would not exist if not for Masters of Doom. So there you go. It’s a great read, highly recommend it, and especially if you’re a gamer because these are the the forefathers of everything that we really know in gaming today.
The other book that I wanted to recommend is one that I actually read pretty recently for the first time, or if I’m being really honest with you, I listened to the audiobook. I still don’t really know how you’re supposed to describe that if you… Do you read an audiobook or do you listen to an audio book? I mean, I guess you really listen to it. It just feels, I don’t know, it feels less impressive when you’re like, “I just listened to this great audio book” rather than read. But anyway, consume your books however you like.
The second is Why We Sleep: The New Science of Sleep and Dreams by Matthew Walker. This was something that I had had recommended to me so many times. It was funny because I was in a new dad at the time. My daughter Olympia was born on September 1st, 2017, and this book must’ve come out around then or some point that year because I was getting it recommended to me all the time while I was unable to sleep because I had a newborn and I thought this is some delightful trolling, and like a lot of things, I kind of put it off and put it off and then finally I was like, “All right, all right. Let me check this thing out. Everyone keeps recommending it to me.”
And so I prioritized it in the Audible account, gave it a listen, and have not been able to stop thinking about it because, really, thanks to technology, we now can really start to understand this really important process that all living creatures need but we’ve never really been able to understand. We’ve been able to do so much research on so many other things that we humans need to survive except for sleep. But thanks to improvements in all kinds of technology, brain scanning and whatnot, and just years and years of research by neuroscientists like Matthew Walker, we’re now starting to understand just what sleep does and why it is so damn valuable and then also how we can better sort of orchestrate it in our lives.
I’ve been someone who is very fortunate as sort of genetically blessed, and thanks to my mom, I think, I’ve never had any trouble sleeping ever. I can sleep, knock on wood, anywhere. Right now in the middle of this podcast, if you said, “Alexis, I really need you to go to sleep,” I could go and curl up in a nice chair or ideally in a nice bed, but I could curl up in a nice chair and be out in probably 10 minutes. Most nights I would get probably six. Six hours of sleep was my goal, and if I got six I thought, “All right, great, let’s do it,” but I never really understood why any of that was important. And in fact, during my 20s and especially founding Reddit, I’d sleep even less. And I almost, I think, I relished it at the time because in some weird perverse way, I thought that that was like showing that I was more serious than anyone else about my startup, which was dumb in hindsight.
And really thanks to this book, I’ve started to understand just how damaging that was and lack of sleep is and just how important it is. Especially if you’re trying to do next-level-type work, how important it is to get rest and recovery. It may seem obvious to you, it definitely didn’t to me, but the recovery and rest is as, or more, important than the work one actually does. You don’t need to look much further than even professional athletes who have the most objectively hard and demanding sort of industries because there are winners and losers every day, and it’s all ranked and a fairly level playing field. And so we make up the wins and losses in business and the way we keep score, but in sport, it’s very objective and very clear, and so it should have been no surprise to me that sleep mattered because every one of the greatest athletes talk about the time that they spend recovering as being as important, or more so, than the time they spend at work.
And so it was a humbling thing to be listening to this and realizing just how dumb I had been for 15 or so years of my life where I was really almost always sacrificing sleep in the name of whatever else it was I was trying to do. I am a new parent now, and thankfully my daughter’s sleeping quite regularly because you’ll learn from the book it’s actually really important in child brain development, and I’m really trying to prioritize it now. I’m really going out of my way to get eight to nine hours of sleep every day almost no matter what, and I have found so many subtle improvements in my own life that have come from it, and I hope the longterm ones will add up, too. I won’t know. You have to check back in within a few years, but the research really is starting to help us understand just how important that time is and just how dangerous it is for us to be living our lives on not enough sleep. The author talks about everything from drowsy driving to the health impacts like the actual internal damage you’re causing in the longterm with consistent sleep deprivation.
And so these are two very different books. They are, I think, indirectly going to help you build billion dollar companies, which is the … that’s the business I’m in now, is to help founders build companies that are even bigger and better than Reddit, and I love that job. And so as an investor at Initialized, I get to give occasional pearls of wisdom to founders, and sometimes they come in the form of books. And these are two books that I found myself recommending quite a bit over the years, and so hopefully they’ll be helpful for you, too. Either way, whether you like them or you hate them, let me know. But those are Masters of Doom and Why We Sleep. So thanks for listening. It’s been a pleasure. I’ll see you on the internet.
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