Marc Andreessen: The 6 secrets of great timing

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When we started, I mean we really had nothing to go on. 'Cause nothing had been recorded for the show yet. Mm-hmm. There was no interviews or anything. So all we knew was that this was a show about

Founders and startups. Yeah, the first challenge was really just deciding on a tempo. Mm-hmm. Having not heard a single episode of the show that hadn't even been created yet, it was tricky to know how fast or how slow to make it, what kind of energy to give it and all that.

That's Brotherly Music Composers Ryan and Hayes Holliday. Together. They've created music for films, art installations, and live performances. Right now. They're talking about one piece of music you may know all too well.

Ryan is the music director for Wait What? The company that produces masters of scale. And together, he and Hayes composed the masters of scale theme. Like any good idea, it went through a number of iterations before it became the piece we all know and love. I mean our first experiments were were definitely pretty off.

I think we did a version that was I will be too slow. A version that was probably a bit too minimal. There may have been a version in there that was a bit sad. Maybe it was raining that day.

It wasn't just the tempo of the music they had to get right, but also the timing. So we had this list of all these great quotes from different founders. And it became obvious that

Just using their words and the company's sounds as kind of the DNA for this thing was the way to go. There are fires burning. So then it really just became a matter of fitting them all in and like building drama. Making it work timing wise.

Less like this. Music is an art. And in art, there are no wrong answers. Well

Mostly no wrong answers. We should release the version that's just four minutes of the word nutballs. Yeah. That doesn't exist. They could.

Don't dismiss this idea so quickly. Really is. Not balls.

As we know, Ryan and Hay's hard work paid off. And they created an iconic piece of music. that captures the energy of masters of scale. And to get that timing right. The tempo.

The beat. The quotes. Meant experimenting with many different approaches. And of all the entrepreneurial skills, timing. Is by far the hardest.

That's why I believe timing is an art with no single right approach. But infinite bad ones. You gotta have incredible talent at every position. It's like this huge push. There are fires burning when you're going out. Can you believe it? And then you go back to this is totally gonna be amazing. There are so many easy ways. I have no idea what to do. Sorry, we made a mistake. But you have to time it right. Oops. Working out of a free bedroom apartment. It just seems absolutely nutball. Ten years later, but well that's just how you do it. We haven't made it just how you do it.

This is masters of scale. I'm Reed Hoffman, co-founder of LinkedIn, partner at Graylock, and your host. And I believe Timing is an art.

With no single right approach. But infinite bad ones. Timing. Like time itself. Is hard to pin down.

It's easy to say if the timing of something was good or bad in retrospect. But a lot of the time when we're talking about bad timing We're talking about bad luck. Timing is of vital importance to any business. When to launch that first product.

When to ramp up scale. When to make the move into a new market. When to pivot. Getting the timing wrong on any of these can have a catastrophic effect on your business. Getting it right will give you a key opportunity.

To get to scale ahead of your competitors. Because of this, we talk about speed a lot on Masters of Scale. But when a topic is as vital as this one, you need to be reminded of it over and over, and you need to update your learnings to stay ahead of the competition. So what are the things to bear in mind? What are the signs that the time for your idea has passed?

Or has yet to come. Or is indeed. Right this second. I wanted to talk to Mark Andreessen about this because as an early internet founder and iconic venture capitalist, he has thought deeply about the role timing plays in a startup success. Mark moved.

To Silicon Valley in nineteen ninety two, having already created Mosaic, the web browser that laid the template. For the way that we use the internet. He went on to create Netscape Navigator. Which at its peak was used by nine out of ten internet users.

It's IPO in nineteen ninety five. heralded the start of the dot com boom. before it sold to AOL in nineteen ninety eight. For ten billion dollars. In two thousand and nine, Mark co-founded V C firm Andreessen Horowitz.

He's a self described optimist. When it comes to tech. But he's also well versed in how timing can make or break a company. or even an entire sector. Mark and I have been good friends for years.

When we sat down to record an episode of Master the Scale. We ended up having a different style of conversation than you're used to hearing. It was less about a specific founding story or scale business. And more a free flowing conversation covering a lot of Mark's ideas on entrepreneurship. We spoke about many subjects.

But timing. And its central importance to success as an entrepreneur was the thread that kept weaving itself through the conversation. That's why this is different than a classic episode of Masters of Scale. We've broken down some of these deep learnings about timing into six insights on why speed is king. In addition to my conversation with Mark, you'll hear relevant examples from previous guests on master the scale and rapid response.

And if you want to hear the complete interviews with every guest on today's episode, then become a member at masterthe scale dot com slash membership. And now. Onto our first insight. Number one.

Timing is the riskiest thing an entrepreneur will face. So my belief has always been that timing is the major variable. It's the major form of entrepreneurial risk in the tech industry. And I think maybe by a wide margin. We were having some technical difficulties during the recording of this interview, so we'll repeat the learning. Mark just shared with us back to you. Timing

І за майже формріал риск. There are of course many, many other risks. Financing. Failure to hire. Building the wrong partnerships.

Getting crushed by a competitor. But if you drew up a pie chart. These would be a small sliver compared to timing. But what does Bad timing even mean.

For Mark. It's all about the market's readiness for what you've created. The big risk in my experience is literally you build the thing and then it just doesn't take because the market's just not ready. And the reason I'm so confident in that point of view is because I have so much experience with basically things that were tried once and then five years later again, and then five years later again, and then five years later again, and then they work. What I wanna emphasize here is your amazing idea is only as good as your timing.

When Mark arrived in Silicon Valley in nineteen ninety three, it felt like the timing was off for everyone. I just remember like the place feeling dead and Part of it was a physical thing, which was empty office complexes and just a general sense of, you know, kind of physical collapse malaise. There was this overwhelming belief in the late 80s, early nineties in the press and in the intellectual circles and political circles that Japan was going to own the future of technology. There were still spurts of innovation, but they didn't take hold.

The ideas weren't bad. But the ecosystem wasn't too much of a malaise to support them. It was even harder. For good ideas to get off the ground.

Ідея це в спровен'я. There were people, including Apple, trying to build the equivalent of the iPhone and the iPad in the late eighties, early nineties. Probably the hottest start up in the valley when I arrived was a company called General Magic that was basically building the iPhone essentially twenty years before the Apple iPhone came out. And by the way, they actually like shipped it. They actually got it to work and they shipped it and it was just like a complete flop. If you aren't familiar with the general magic story, it's a classic case study of a great idea. That was ahead of its time. And so like that was sort of obviously a good idea. It just took another 20 years to get to it. And so I've just now seen so many times.

that people just need to take swings at these things over a twenty or thirty or forty year period until they get them to work. And so The good news is most of these things happen. The bad news is many attempts fail because quite literally they were just too early. A lot of timing. Rest on whether there is an ecosystem to support your product. The classic example is how many internet services never made it because the bandwidth wasn't there.

Of course, this is easy to see in hindsight. But gauging in real time if the ecosystem is ready. Is the hard. May be impossible. Part.

Because one of the defining things about all truly great ideas Is that no one knew they needed it in their lives. Until it appeared. Entrepreneurs are visionaries and optimists. Which make it especially hard to judge if the time is right for your idea.

Timing is your biggest risk. But it is also in some ways unavoidable because entrepreneurs have to live in the future. They have a vision of the world that doesn't yet exist. But the refusal to live in the past. Can in fact be an advantage.

Which brings me to our next insight. Number two. To time things right. A bit of ignorance might help.

You have to live in the future, you have to extrapolate forward. But yet we have this just incredible track record of these very sharp entrepreneurs being, you know, early too early over and over again. And so basically they're kind of caught in the mouth of that fundamental tension. If you're well versed in the history of some of these failures. The danger is you might think the idea itself is flawed.

Generally, when somebody fails once at something, they'll never try it again. And so kind of the twist on this is it's not like it's the same founder or the same team trying time after time after time to get the thing right for the most part. It's almost always new teams. And in fact, one of the things that's really funny that you probably have experienced in your investing career is Often the new teams, including the ones that finally get it right, often they're not even aware of the history. Yes. this happens all the time I'll be meeting with you know a group of 25 year olds or whatever and it's like they'll be pitching some idea to me and literally in my head I can basically name the companies five years ago, 10 years ago 15 25 years ago that tried the thing and failed. I used to ask well are you aware of all these previous attempts and half the time they say no what were those? You know, or they would just roll their eyes, being like, Well obviously those guys are stupid, like or they would have gotten it to work.

That I rolling brashness can be the antidote. To this fear of repeating past failures. As far as I can tell, there's actually very little benefit in even being aware of the history. And in fact, being aware of the history might actually be a negative, right? Because the world does change. Like the conditions on the ground do change. The markets actually do become ready for new things at a certain point. The technology really does reach the point where something is really going to work, right? Whatever are the other preconditions of success, they do happen. Most of these things do end up working. It's good to learn from the past. It's bad.

To be deterred by it. This is something that BuzzFeed co-founder and CEO Jonah Paretti talked about in a 2021 Episode of Master the Scale Rapid Response. The episode was titled How Buzzfeed bounced back.

Here's Jonah talking about when the first wave of the Covid pandemic hit. The challenge is that the past is not really a great guide of what things are gonna be like in the future, right? So the start of the pandemic The entire company was in crisis mode, there was urgent goals, urgent changes, things that had to be done. Then later in the pandemic You had some of the excitement of getting through the worst of it and the business improving.

And then throughout this you start to have burnout and people feeling like they're not getting that, especially more extroverted people, they're not getting that. energy they get from being with their peers and being with colleagues and then how do you manage that? And we did things like adding a monthly mental health day and encouraging people to take time off. And then What we're heading into now is also unprecedented. So you can't just look at the past and figure it out, which is a more hybrid model.

where you may have people coming into the office two or three days a week. I think if there's any lessons from all of this, it's that whether it's the digital economy or whether it's unexpected things like a pandemic. You just have to be able to build a company that is so adaptable and dynamic and can change and shift. in order to navigate this economy and I feel like That's just been a a huge lesson from this and watching the team navigate through these challenges and do things they just didn't imagine they could have even possibly done. You know, just like March, April, May of last year thinking, Oh my God, are we gonna be able to make payroll to having

hundreds of millions of cash on the balance sheet and acquisitions and the ability to go public. And so it makes me really proud of the team and Makes me just realise that you have to build this resiliency into the company and the culture in order to operate in this world that we're in because it's amazing how quickly things move. As Jonah highlights, wildly improbable. or even impossible to predict situations will occur.

And there's nothing wrong in looking back to the past for inspiration. But we also need to build the ability and agility into our organizations. To adapt to novel situations. When it comes to launching a new product or service, ask yourself. Is there a fundamental problem with this idea?

Or Is there a mismatch in timing? Here's Mark again. There's always this question in my mind of whether you even want negative lessons from the past because they might just mislead you in a negative way, where the right thing to do might just be to ignore all that and just try to like do the new thing clean and then a fair amount of time it just works. And so I think this might be the kind of most magical aspect of entrepreneurial judgment, and I'm honestly not sure how to coach people on it.

Yeah, I have exactly the same like point of view. And by the way, I also resemble some of the failures. Like I missed square and stripe because I had the experience with PayPal and Oh yeah, this is really hard and difficult and da da da and you're like, Oops right you know, as an investor. The joke that I tell within Greylock is Actually, in fact, I'm not our payments expert, I'm our payments idiot.

Who We'll pass on the things that we should be thinking about in terms of the future of this. Another thing I'm known for is my passion for harnessing the power of network effects. This is something that Mark also understands deeply. Which brings us to our next insight.

Number three. Leverage your network. To create the right timing. There's this combination of psychology and sociology, but psychology is individual. So it's like is the individual customer, you know, unit of one gonna buy this thing.

And then there's the sociological component, which is maybe even more important, which is is there going to be a large group of people who are going to do this because they're literally feeding off of each other, right? You know, they're watching each other's decision making process. And of course, this is incredibly important, obviously, for anything that involves network effects where you actually need where N of one doesn't help you, right? You need a million or something. Understanding how network effects can be harnessed. can let you make it the right time for your product. The best entrepreneurs, they've got theories, they've got frameworks, they've got plans, got some way to get to market and so forth. And that's all important. But I think they also need like a very deep intuitive sense of the market. And I think again, that's a hard thing to teach. It might be hard to teach, but it's seen time and time again in almost every industry.

Hollywood is an industry in which timing is crucial. But complicated by many factors. Not least the sheer volume of unproduced scripts. It's a problem that Franklin Leonard set out to fix as a junior executive in Hollywood. Tasked with sifting through hundreds of scripts.

I sort of said, You know what, let me try to take a systemic approach to solving the problem of finding good screenplays. I literally went through my calendar. And I made a list of everyone I had had breakfast, lunch, dinner, or drinks with. If they had a job similar to mine, I sent them an email anonymously and said, Send me a list of your ten favorite unproduced screenplays. In exchange, I'll I'll share with you the combined list. I think the first list was ninety three votes. Very small data set, right? Ran the votes through a pivot table, output it to PowerPoint, slapped a quasi-subversive name on it, and sent it out anonymously.

And went on vacation. checked my email at the hotel business center a weekend and it had been forwarded back to me seventy five times. When I got back to Los Angeles, I'd go to Industry events. Oh, where this thing, the blacklist, the scripts on it are really good. Where did it come from? I get a phone call from an agent who was pitching me on a client. Hey, I have this new client. I love his script. I'm pretty sure Leo's gonna want to do it as his next movie. I already sent it to Brad Pitts Company, so you should probably read it tonight, right? The standard agent C Spiel. But this one ended differently.

Look and don't tell anybody. I have it on really good authority that this is gonna be the number one script on next year's blacklist. And I remember sitting in my office on sunset. And looking out the window, trying to process what this guy had just said, because I had made the blacklist. It's a survey. So the notion of

I have on good authority that this is gonna be number one is just a Bold face lie. Right. But it was also a simultaneous realization that wait a minute, this thing that I created just to find good scripts for myself apparently has more value than I anticipated. Because if this agent is out here calling random people, And for all he knows, I am a random person.

Sane. This trip's going to be number one. That must mean that being number one has a great deal of value. And if that's true. There may be other things that are true about the forces that the thing is set into motion.

The blacklist. soon became a vital barometer. Of the hottest unproduced scripts in Hollywood. And a clear example. of how you can build a network that creates the precise timing you need to scale.

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Creative planning where wealth works together. Learn more at creative planning dot com slash masters of scale. Hey listeners, Bob here. If you listen to Rapid Response on Masters of Scale, you may be missing half the show. Because every Friday we release a second rapid response exclusively in the Rapid Response feed. The guests and topics are just as compelling and timely from Ford's CEO to NASA's administrator to the lessons from The Devil Wears Prada. It takes about 10 seconds to find, just search rapid response wherever you listen to podcasts and hit follow to make sure you never miss an episode.

I hope to see you there. Humans will never be more intelligent than AI. There can be two types of companies. Those are great at AI and those that went out of business because they weren't. How do we build a future?

That is human centered. I'm Rana El Kalyubi. And on my podcast Pioneers of AI, we answer that question and so many more. As an AI scientist, entrepreneur, and investor, I know what it takes to build AI that works for everyone. Every week, I sit down with the pioneers shaping our future. And we take you behind the scenes of the AI that's transforming our lives.

Find pioneers of AI wherever you tune in. We're back. With Mark Andreessen. Venture capitalist at Andreessen Horowitz and co founder of Netscape. If you're enjoying this episode and want to share it with friends, send them the link.

Masterscale.com Slash Andreessen. That's A N D R D E Double S.

Yeah. And you can hear my complete interview with Mark by becoming a Master of Scale member at masterscale.com. Slash membership. We're talking timing this episode. And right now.

It's time for our fourth insight from Mark. Number four. If you wait until your idea is hot. You've waited.

Too late. This is fundamental to Marx unified theory of entrepreneurship. And it's also at the core of how Andrees and Horowitz operates. One of Mark's partners there, Chris Dixon. Articulated this way.

So what Chris basically says this in the venture business or in the tech startup community in general, we're in the business of basically doing the good ideas that look like bad ideas. So we're in the business of doing the good ideas because obviously like being the business of doing the the actual bad ideas, it's a bad idea. So we we are trying to back the good ideas, build the good ideas. But the thing with good ideas is that if they were obviously good ideas to the world at large, they would already have been done. You could go up with like a thousand examples just here's an obviously good idea, right? An obviously good idea is a smartphone whose battery lasts fifty percent longer. Right. Like that's obviously a good idea because who hasn't gotten annoyed at the end of day when they run out of charge. And it's like, okay, that's like an obviously good idea, but guess what? Apple knows that's an obviously good idea. Right. And guess what? They're doing it. You as a startup try to do that, like you're in a great deal of trouble. So the obviously good ideas are off the table. And so that means that we basically have to fish for good ideas in the giant pond of ideas that look like bad ideas.

The problem with that is that most ideas that look like bad ideas are bad ideas. Yeah. Right. So part of what we do is basically fish through that pond. and trying to discard the bad ideas that are actually bad ideas and sort of uh you know pull out the apparently bad ideas that are actually good ideas. You have to be contrarian, right? You have to basically say, okay, all the experts say, or the entire press course says, or all of the university researchers say, or by the way, all the VCs say.

idea X is a bad idea, and you have to be able to like basically shed the social conformity aspects, you know, that are kind of so innate to how we behave. And you have to be able to look at it objectively as best you can and say, well, no, actually this one could actually be one of these good ideas. Look at the bad idea objectively. And you might actually find it's a good idea. For a useful example of this, here's Michael Seibel, Y Commander Managing Director, and Co-Founder of Justin TV. Which became Twitch.

We join Michael. As he recalls his partner Justin Conn pitching him. on the Justin TV concept. Justin Told me they were doing this over dinner with his dad in DC, and we both told him it was the dumbest idea we've ever heard in our lives.

Which I still believe to this day. That idea was Justin TV. The plan to live stream Justin's day to day life. twenty four seven with a webcam attached to Justin's head. Today this seems quaint, but in two thousand six this was brand new.

I think that in hindsight We always tell founders to start companies to solve personal problems. And back then he wanted to be an influencer and there were no influencer platforms. Twitter didn't exist like all the things that an influencer would just reach for. He didn't have and so

Almost incredibly he invented a platform that allowed himself to become an influencer. Note that Y C edict. That Michael mentioned. Why see he always tells founders to start companies to solve personal problems? It's invaluable advice.

By asking yourself Which problem is most personal to me, you're far more likely to hone in on a mission that you will have limitless drive to follow. And that's why even if that mission seems irrational compared to others you could be following. It really is the one that you should be following. The thing that kept on sticking in my mind was all of my other options

would be available in the future. Every other thing I was considering doing would be available, and this is the one thing that felt like it would never happen again. Helping my friend start a company. And something just told me do the thing you can never do again when you're twenty three and have nothing going on in your life. Seems like a good play. And it was.

And so I called them and I said, Uh yeah, uh I'm in. This last point for Michael is an important one to bear in mind. The timing needs to be right for you as well as your product. And for Michael With little to lose and a hunger for entrepreneurship.

the timing to jump abound an unproven idea like Justin TV. Was right. And very soon. Justin TV became the hottest startup. Generating feverish press coverage.

And spawning numerous imitators. And this also goes to the heart of another topic Mark and I talk about a lot. Which is the role heat plays in the world of startups. Who's hot? Who's not?

Who's good at finding the heat? Where will the next hot spot be? At any point in time, right, you or I could probably list here are the spaces that are hot and within that here are the companies that are hot. And then You know, you and I both probably know a bunch of entrepreneurs today who we think are very good, who are off pursuing some idea that's very hot hot. Yes. Right. And often it's not hot because part of it's just it's not whatever is the trend of the moment, but also in a lot of cases, it's not hot because literally somebody tried failed, or by the way, maybe an entire sector was tried and failed five or ten years earlier. It just was like total wreckage after the fact. And so a space goes from hot to cold when there's a whole run of failures. And then you get these really sharp entrepreneurs who are off pursuing what looks like some sort of

almost private muse kind of fishing in a space that you just know for a fact is just stone cold. And those entrepreneurs might have a real challenge because it can be very hard, right, for obvious reasons to raise money, you know, over time for those space is not hot because a lot of investors will just roll those spaces out, if even just to make their lives easier. And so one of the things I've really come to believe is you can't draw any conclusion in the moment about whether a space is hot. Yeah. And it goes hand in hand with what you said, which is like a hot space is probably going to overfund a category. There are probably going to be too many companies in the category. That's going to reduce the risk of a single big success. Conversely, a not hot space may simply be one that's gone fallow until the time is right, and maybe now the time is right. And then maybe the person doing the cold thing is gonna be the only person doing it. And maybe that's how you're gonna get the really big hit coming out the other side. And so in that sense, I think heat may just simply not be correlated. Yeah, to reinforce the point you just made. I was one of the earliest people that Elon talked to about SpaceX. And I laughed at him and of course there was a fool in the room, but just didn't happen to be him. And the contrarian thing was

Okay, you're gonna go build rockets when it's hardware, not software, when it's all locked up by arcane RFP processes from former Air Force colonels who go into defense contrasting companies and have it locked up, and you're gonna outcompete that with a better Rocket engine. Uh. Really? Right. And it turned out to be the answer was

Yes. All right. The only thing crazier than that, I mean the only thing just obviously dumber than that would be a new car company. That dumb idea, of course, became Tesla. It's an example of how predicting the future is an impossible game. But it's a game.

You absolutely Have to keep playing. Which brings us to our fifth insight. Number five.

Always be future casting. A big factor in getting your timing right. is projecting the state of play at present. Into the future. And what that means for you.

Your competitors and your industry. One example Mark gives is video editing software. There's a whole UI for video editing that's of course become dominant for everything from major movies all the way to TikTok videos over the last thirty or four years with like the timeline and of the different edit tools and the effects tools and everything. And it's like I think AI driven video editing, like I don't think you have any of that stuff. Cause I think what you do is you basically just tell the computer, you know, give me a cut of my You know, dump in all the raw footage for my wedding. And you know, give me the you know, remains in the day cut or give me the blade runner cut. Right? Or give me the I don't know, you know, pick whatever aesthetic you want. Yeah, or even give me

halfway between remains the day. And And Blade Runner. And then you'll get something interesting. Yeah. Yeah, exactly. And then the computer basically does it, shows it to you, and you're like, Okay, well, that's a little bit dark. And then by the way, I think you know, maybe you know it feels like it's segment a little bit, but the music's feeling a bit more upbeat.

And the computer goes in click like war and gives you another cut. What can AI driven video editing do? In the fullness of time, right? It can learn from watching every Steven Spielberg movie and every David Fincher movie and every commercial. And the AI algorithm could watch every TV commercial ever made, could rank order them by like all those of commercial success, all the demographics, and then it could literally know how to cut the perfect commercial for any product, right before the editor even shows up, you know, to even take a look at the first cut. This is an example of the kind of future casting you can do. It's fun. You could end up with some wacky sci fi scenarios.

But With a few ideas. idea that you're gonna have any of the existing products actually make that jump over the next like twenty years I think is really small. We're guessing it happens faster. So we're anyway, we're backing a lot of companies to kind of have this mentality. You know, we may have the timing wrong, but I I tend to think this is gonna happen. Yeah, I totally agree. Th I always entertain when I'm asked the question I'm about to ask you, because I think being too definitive in predictions is always a a little bit of a fool's errand.

But what do you think is coming within the AI side Two years, five years, ten years. That people don't really see coming. Get in the habit of fantasizing about the future. At the very least, it will help spark new ideas and new mindsets.

And don't feel that your future casting needs to be as extreme as speculating about AI. Or flying cars. And it doesn't need to be on the scale of decades. The more specific you can make it to your venture, the more actionable it will be. This is a practice that Sarah Hirschland

CEO of the US Olympic and Paralympic Committee has cultivated. Here she is discussing it when she appeared on Rapid Response. My job is to listen, but to be effective in listening and learning things that are valuable to me in my role, I also have to ask really good questions. And so I try to go into those conversations and ask thoughtful questions that will allow them To share things with me.

that I can act on, right? That I can actually use in planning the organization in our strategic work. So at times I talk with athletes about the competitive support that they're getting. And the resources that they're getting. At times I talk with them about life transition. You know, one of the single most difficult things for elite athletes is that realization as you come into the recognition that you're

Special. You know, that you're better than most. Being in that place But then there is inevitably there's an off ramp of being an elite athlete. And so what does that look like and how does that transition happen? And what is the next phase in life? And how do we as an organization

Provide support and resources around that moment. For some it's very sudden, for others, it's years in the making. And that's a place where we've got a lot of work to do to really think about how to help support that. So I ask a lot of questions of athletes about their personal experiences in those ways. Asking questions of yourself and others is an essential part of refining your timing. But just as important. is being open to the answers you get.

Which brings us to our sixth and final insight. Number six. Get more. Not less.

Open minded. I think by any objective measure, like, you know, I've been on the leading edge of like a lot of things over time and I'm enthusiastically prone to ideas. Yeah, pro no technologies. And I have just routinely found that I have underestimated way too many of the things that turn out to be really big. Even if you have a track record of being open minded like Mark. There's always room to be more open minded.

And this is why it's important to proactively cultivate an open mind. Every time you embark on a new project. and at regular points within a project. This is something that President Barack Obama began doing early in his career. As he told us in part one.

of his two part appearance on Masters of Scale. When I moved to Chicago This is in nineteen eighty five. I had been inspired by the civil rights movement. And John Lewis and people like that.

I was inspired by the notion of big movements as the most reliable means to bring about significant social change. I was inspired by Gandhi and solidarity in Poland and I thought that Electoral politics. Tended to be

Geared towards the status quo? that those who participated in it oftentimes weren't pushing for the kinds of changes that I wanted to see in the country. The young Barack Obama. Had come to Chicago.

Famously. As a community organizer. He was looking for a grand social movement of his own. But But there was no movement going on at the time.

This is right smack dab in the middle of the Reagan era. Sort of Gordon Gecko, Greed is good. America's back. And So there was a lot of skepticism at that point about social movements.

In terms of pure product market fit, it seemed like the timing was all wrong. There didn't seem to be much appetite for a new civil rights era. Or a war on poverty. At least. Not that this recent Harvard Law graduate could see.

When I first arrived, this older organizer asked me, All right, what do you think your plan is to bring about change? And I said, Well coming from an academic background. I've got all these ideas about how we can put people back to work and change policy on education and this and that and the other. He says, Yeah, that's fine, but I want you to spend the first month Just going

And talking to everybody you can meet in this community. And Then come back and tell me their stories. And I thought, Well, that doesn't sound very exciting, and that doesn't sound like I'm charging the ramparts and Changing the world.

But it probably ended up being the most important valuable lesson not just for organizing but for politics. Because For a month. I went around and all I did was just listen.

It might seem simple, but learning to listen is something every entrepreneur needs to do. You can't identify a launch window if you haven't even identified your mission. But listening to your customers, or in this case your community, can make that mission clear. I asked people about their families and the history of migration from the south to Chicago and what it was like when they first started working at a steel mill and What the church meant to them and

what their traditions were and what their hopes And fears were You discover that everybody's got a sacred story of their own. I'm a big believer in the power of people's stories as the thing that moves people to action. And I think that I ended up importing.

into my campaign work. Barack Obama Had come to Chicago looking for a movement. And on the surface, it seemed like he'd come too late. but the daily organizing practice of knocking on doors.

Listening to people's stories. And registering them to vote was actually sowing the seeds of a new movement that was just beginning. There's actually a parallel here in the startup world. As a strategic entrepreneur, you're not trying to get in at the peak of a trend. You're trying to be one to three years early, so you can have time to build toward it. So when the moment arrives, you already have momentum.

While everyone else scrambles to get up to speed. Like Obama. Mark makes keeping an open mind a priority. Especially in his approach to timing. of the big five personality traits is openness. And the thing with openness is it actually falls over time over your lifespan and all the testing will show you you just get less open, which maps to what kind of people experience, which is you know people who as they get older generally they won't listen to new music, you know, they won't buy new consumer products if everybody knows this. And so there's this natural inclination the longer you work, the more closed option new ideas you're gonna get. And so

I think there's something very necessarily self-conscious about the idea that you need to fight hard in the other direction. One is because you need to offset the fact that you're probably getting you know less open over time just naturally. And then the other is you were probably not sufficiently open enough to start with. One of the real dreams of my life was to meet somebody who's 80 and who's intensely curious. Yes. And I'm just like, wow, that's impressive. And that's what I want to be like. I often say that the greatest entrepreneurs function from within a reality distortion field.

Making the impossible seem possible, not just to themselves. But to those around them. Part of finding the right time to launch your product is making it the right time and bringing other people along with you. But the other key to developing your timing is maintaining your curiosity. And open mindedness.

The best way to do this is to be open to new experiences, new viewpoints, and be willing to entertain the notion of giving anything a shot. Because part of being close minded is to say, nope. Oh no. I'm good with what I got. And that's Living in the past.

Not The future. There is. No foolproof secret to timing. But your chances of getting your timing right.

will be immensely greater if you keep your optimistic mindset. Alive. If you succeed in this Then better futures are possible. I'm Reed Hoffman.

Thanks for listening. Masters of Scale is a Whitewater Original. Our executive producers are June Cohen and Darren Triff. Our senior producer, Jordan McLeod. Our supervising producer is Jave Punjabi. Our producers are Adam Skuse, Catherine Clark Gray, Hiley Bondi, Marie McCoy Thompson, and Christina Gonzalez. Our editor at large is Bob Safia. Our music director is Ryan Holliday. Original music and sound design by Eduardo Rivera. Audio Editing by Keith J. Nelson, Steven Davies, Andrew Naught, and Mike Gallagher. Mixing and Mastering by Brian Pugh.

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