The Masters of Scale origin story

RYAN HOLLADAY: When we started, I mean, we really had nothing to go on because nothing had been recorded for the show yet. There were no interviews or anything. So all we knew was that this was a show about founders and startups.

HAYS HOLLADAY: Yeah. The first challenge was really just deciding on a tempo, having not heard a single episode of the show that hadn’t even been created yet. It was tricky to know how fast, speed, or how slow to make it, what kind of energy to give it and all that.

REID HOFFMAN: That’s brotherly music composers Ryan and Hays Holladay. 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 WaitWhat, the company that produces Masters of Scale. And together, he and Hays 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.

RYAN HOLLADAY: I mean, our first experiments were definitely pretty off. I think we did a version that was probably too slow, a version that was probably a bit too minimal. 

I think there may have been a version in there that was a bit sad.

HAYS HOLLADAY: Maybe it was raining that day.

HOFFMAN: It wasn’t just the tempo of the music they had to get right, but also the timing of the different elements.

RYAN HOLLADAY: 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 sounds as, kind of, the DNA for this thing was the way to go. So then it really just became a matter of fitting them all in and building drama – making it work timing wise.

HOFFMAN: Music is an art. And in art, there are no wrong answers. Well, mostly no wrong answers:

RYAN HOLLADAY: We should release the version that’s just four minutes of the word nutballs.

HAYS HOLLADAY: That doesn’t exist.

RYAN HOLLADAY: It could. Don’t dismiss this idea so quickly.

HOFFMAN: Now that really is nutballs.

As we know, Ryan and Hays’ 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.

Theory: Timing is an art, with no single right approach

HOFFMAN: I’m Reid Hoffman, co-founder of LinkedIn, partner at Greylock, 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 Marc 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’s success.

Marc moved to Silicon Valley in 1992, 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 9 out of 10 Internet users. Its IPO in 1995 heralded the start of the dotcom boom, before it sold to AOL in 1998 for $10 billion.

In 2009, Marc co-founded VC firm Andreessen Horowitz. He is a self-described optimist when it comes to tech, but he is also well versed in how timing can make or break a company – or even an entire sector.

Marc and I have been good friends for years. When we sat down to record an episode of Masters of 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 Marc’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 Marc, you’ll hear relevant examples from previous guests on Masters of 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 mastersofscale.com/membership.

And now, on to our first insight:

Number 1: Timing is the riskiest thing an entrepreneur will face

MARC ANDREESSEN: 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. 

HOFFMAN: We were having some technical difficulties during the recording of this interview, so I’ll repeat the learning Marc just shared with us back to you: Timing is the major form of entrepreneurial risk. 

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 Marc, it’s all about the market’s readiness for what you’ve created.

ANDREESSEN: 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 kind of once, and then five years later again, and then five years later again, and five years later again, and then they work.

HOFFMAN: What I want to emphasize here is your amazing idea is only as good as your timing. When Marc arrived in Silicon Valley in 1993, it felt like the timing was off for everyone.

ANDREESSEN: I just remember the place feeling dead. And part of it was a physical thing, which was empty office complexes and just a general sense of kind of physical collapse, malaise.

There was this overwhelming belief in the late ’80s, early ’90s in the press and in the intellectual circles and the political circles that Japan was going to own the future of technology.

HOFFMAN: There were still spurts of innovation, but they didn’t take hold. The ideas weren’t bad. But the ecosystem was in too much of a malaise to support them. It was even harder for good ideas to get off the ground – ideas that have since proven themselves.

ANDREESSEN: There were people, including Apple, trying to build the equivalent of the iPhone and the iPad in late ’80s, early ’90s. Probably the hottest startup in the Valley when I arrived was a company called General Magic that was basically building the iPhone essentially 20 years before the Apple iPhone came out. And by the way, they actually shipped it. They actually got it to work and they shipped it, and it was just a complete flop.

HOFFMAN: 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.

ANDREESSEN: And so 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 20 or 30 or 40-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.

HOFFMAN: A lot of timing rests 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, maybe 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 makes it especially hard to judge if the time is right for your idea.

Timing is your biggest risk; but it also is 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 their refusal to live in the past can in fact be an advantage, which brings me to our next insight.

Number 2: To time things right, a bit of ignorance might help

ANDREESSEN: 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 early, too early, over and over again. And so basically, they’re kind of caught in the mouth of that fundamental tension.

HOFFMAN: If you’re well-versed in the history of some of these failures, the danger is you might think the idea itself is flawed.

ANDREESSEN: 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.

HOFFMAN: Yes.

ANDREESSEN: Because, this happens all the time. I’ll be meeting with 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, 20, 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’d say, “No, what were those?” Or they would just roll their eyes. They would just basically be like, “Well, obviously those guys were stupid, or they would’ve gotten it to work.”

HOFFMAN: That eye-rolling brashness can be the antidote to this fear of repeating past failures.

ANDREESSEN: And 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 history might actually be a negative, because basically the world does change. 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. Whatever are the other preconditions of success, they do happen. Most of these things do end up working.

HOFFMAN: 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 Peretti talked about in a 2021 episode of Masters of 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.

JONAH PERETTI: The challenge is that the past is not really a great guide of what things are going to be like in the future. So at the start of the pandemic, the entire company was in crisis mode. There were 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?

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.

And 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 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. 

Just like March, April, May of last year thinking, “Oh my God, are we going to 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 realize 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.

HOFFMAN: 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 Marc again.

ANDREESSEN: 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 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.

HOFFMAN: Yeah. I have exactly the same point of view. And by the way, I also resemble some of the failures. I missed Square and Stripe because I had the experience with PayPal and went, “Oh, yeah, this is really hard and difficult and da, da, da,” and you’re like, “Oops.” Right?

ANDREESSEN: Yeah.

HOFFMAN: As an investor.

ANDREESSEN: Yep.

HOFFMAN: The joke that I tell within Greylock is actually, in fact, I’m not our payments expert, I’m our payments idiot who will pass on the things that we should be thinking about in terms of the future of this. 

HOFFMAN: Another thing I’m known for is my passion for harnessing the power of network effects. This is something that Marc also understands deeply. Which brings us to our next insight.

Number 3: Leverage your network to create the right timing

ANDREESSEN: There’s this combination of psychology and sociology. The psychology is individual, so it’s like, is the individual customer unit of one going to buy this thing? And then there’s the sociological component, which is maybe 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 each other. 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 an N of one doesn’t help you, you need a million or something.

HOFFMAN: Understanding how network effects can be harnessed can let you make it the right time for your product.

ANDREESSEN: The best entrepreneurs, they’ve got theories, they’ve got frameworks, they’ve got plans, they’ve got some way to get to market and so forth, and that’s all important, but I think they also need a very deep, intuitive sense of the market, and I think, again, that’s a hard thing to teach.

HOFFMAN: 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.

FRANKLIN LEONARD: 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 10 favorite unproduced screenplays. In exchange, I’ll share with you the combined list.” 

I think the first list was 93 votes. Very small data set, right? I 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.

Check my email at the hotel business center, a week in, and it had been forwarded back to me 75 times. When I got back to Los Angeles, I’d go to industry events, “Oh, where’d this thing, the Black List, the scripts on it are really good. Where’d it come from?”

I get a phone call from an agent who was pitching me on a client. 

AGENT: Hey, I have this new client, I love his script. I’m pretty sure Leo is going to want to do it as his next movie. I already sent it to Brad Pitt’s company. So you should probably read it tonight.

LEONARD: The standard agency spiel. But this one ended differently.

AGENT: Look, and don’t tell anybody, I have it on really good authority, this is going to be the number one script on next year’s Black List.

LEONARD: 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 Black List. It’s a survey, so the notion of “I have on good authority that this is going to be number one” is just a bold-faced 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, saying…

AGENT: This script’s going to be number one.

LEONARD: …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 has set into motion. 

HOFFMAN: The Black List 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.

[AD BREAK]

HOFFMAN: We’re back with Marc Andreessen, venture capitalist at Andreessen and Horowitz and co-founder of Netscape.

If you’re enjoying this episode and want to share it with friends, send them the link mastersofscale.com/andreessen. That’s A-N-D-R-double E-double S-E-N. And you can hear my complete interview with Marc by becoming a Masters of Scale member at mastersofscale.com/membership.

We’re talking timing this episode. And right now it’s time for our fourth insight from Marc.

Number 4: If you wait until your idea is hot, you’ve waited too late

This is fundamental to Marc’s unified theory of entrepreneurship. And it’s also at the core of how Andreessen Horowitz operates. One of Marc’s partners there, Chris Dixon, articulated it this way.

ANDREESSEN: So, Chris basically says this, in the venture business or 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, being in the business doing the actual bad ideas is a bad idea. So, we are trying to back the good ideas, build the good ideas. 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 come up with like a thousand examples. I’ll give you an obviously good idea. An obviously good idea is the smartphone whose battery lasted 50% longer. That’s an obviously good idea because who hasn’t gotten annoyed at the end of the day when they run out of charge? It’s like, okay, that’s an obviously good idea, but guess what? Apple knows that’s an obviously good idea and, guess what? They’re doing it.

If you, as a startup, try to do that, you’re in a great deal of trouble. So, basically, the obviously good ideas are off the table.

So, that means that we basically have to fish for good ideas in the basically 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, right?

So, part of what we do is basically fish through that pond and try to discard the bad ideas that are actually bad ideas and sort of pull out apparently bad ideas that are actually good ideas. You have to be a 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 basically shed the social kind of conformity aspects that are kind of so innate to how, how we behave, and you have to be able to kind of look at it objectively as best you can and say, “Well, no, actually, you know, this one could actually be one of these good ideas.

HOFFMAN: 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 Combinator managing director and co-founder of Justin.tv, which became Twitch. We join Michael as he recalls his partner, Justin Kan, pitching him on the Justin.TV concept.

MICHAEL SEIBEL: 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. 

HOFFMAN: That idea was Justin.tv. The plan: to livestream Justin’s day-to-day life, 24-7, with a webcam attached to Justin’s head. Today this seems quaint, but in 2006 this was brand new. 

SEIBEL: 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. 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.

HOFFMAN: Note that YC edict that Michael mentioned: YC 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.

SEIBEL: 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 friends start a company. And something just told me, “Do the thing you can never do again when you’re 23 and have nothing going on in your life. Seems like a good play.” And it was. And so I called them, I said, “Yeah, I’m in.” 

HOFFMAN: This last point from 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 aboard 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 Marc 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? 

ANDREESSEN: At any point in time, 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 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 not hot.

HOFFMAN: Yes.

ANDREESSEN: Often, it’s not hot because part of it just is not whatever is the trend of the moment, but also in a lot of cases, it’s not hot because, literally, somebody tried and failed or, by the way, maybe an entire sector was tried and failed five or 10 years earlier.

It just was like total wreckage after the fact. 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 basically 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.

Those entrepreneurs have a real challenge because it can be very hard, for obvious reasons, to raise money over time in a space that is not hot because a lot of investors will just rule those spaces out, if even just to make their lives easier. 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.

HOFFMAN: Yep.

ANDREESSEN: 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 going to be the only person doing it. Maybe that’s how you’re going to get the really big coming out the other side. So, in that sense, I think heat may just simply not be correlated.

HOFFMAN: 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. Of course, there was a fool in the room. It just didn’t happen to him.

The contrarian thing was, okay, you’re going to 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 contracting companies and have it locked up, and you’re going to outcompete that with a better rocket engine. Really? It turned out to be the answer was yes.

ANDREESSEN: The only thing crazier than that, I mean, the only thing just obviously dumber than that would be a new car company.

HOFFMAN: 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 5: Always be futurecasting

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 Marc gives is video editing software.

ANDREESSEN: 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 30 or 40 years with the timeline and the different edit tools and the effects tools and everything.

I think AI-driven video editing, I don’t think you have any of that stuff because I think what you do is, you basically just tell the computer, give me a cut of my, dump in all the rough footage from my wedding, and give me the Remains of the Day cut or give me the Blade Runner cut or pick whatever aesthetic you want.

HOFFMAN: Or even give me halfway between Remains of the Day and Blade Runner, and then you’ll get something interesting.

ANDREESSEN: Yeah, exactly. It’s like, then the computer basically does it, shows it to you, and you’re like, okay, well that’s a little bit dark. Then, by the way, I think maybe it feels exciting a little bit, but the music should be a little bit more upbeat, and the computer goes click, click or it gives you another cut.

What can AI-driven video editing do in the fullness of time? It can learn from watching every Stephen Spielberg and every David Fincher movie and every commercial. An AI algorithm could watch every TV commercial ever made, could rank order them by all their levels 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 to even take a look at the first cut.

HOFFMAN: This is an example of the kind of futurecasting you can do. It’s fun. You could end up with some wacky sci-fi scenarios. But you may also come up with a few ideas.

ANDREESSEN: The idea that you’re going to have any of the existing products actually make that jump over the next 20 years, I think, is really small. We’re guessing it happens faster. So anyway, we’re backing a lot of companies that kind of have this mentality. We may have the timing wrong, but I tend to think this is going to happen.

HOFFMAN: Yeah. I totally agree. 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 little bit of a fool’s errand, but what do you think is coming within the AI side two years, five years, 10 years that people don’t really see coming?

HOFFMAN: 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 futurecasting 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 Hirshland, CEO of the U.S. Olympic and Paralympic Committee, has cultivated. Here she is discussing it when she appeared on Rapid Response:

SARAH HIRSHLAND: 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 and 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.

One of the single most difficult things for elite athletes is that realization as you come into the recognition that you are special, that you are 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.

HOFFMAN: 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 6: Get more, not less, open-minded

ANDREESSEN: I think by any objective measure, I’ve been on the leading edge of a lot of things over time. And I’m enthusiastically pro new ideas, pro new technologies. And I have routinely found that I have underestimated way too many of the things that turn out to be really big. 

HOFFMAN: Even if you have a track record of being open minded like Marc, 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 1 of his two-part appearance on Masters of Scale.

BARACK OBAMA: When I moved to Chicago, this was in 1985, 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.

HOFFMAN: 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…

OBAMA: 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 Gekko, greed is good, America’s back. And so there was a lot of skepticism at that point about social movements. 

HOFFMAN: 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.

OBAMA: 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.  

HOFFMAN: 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. 

OBAMA: 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 has 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.

HOFFMAN: 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, Marc makes keeping an open mind a priority, especially in his approach to timing.

ANDREESSEN: One 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 people experience, which is people as they get older, generally, they won’t listen to new music. They won’t buy new consumer products. Everybody knows this. And so there’s this natural inclination, the longer you work, the more closed off to new ideas you’re going to 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 less open over time just naturally. And then the other is you were not sufficiently open enough to start with.

One of the real joys in my life is to meet somebody who’s 80 and who’s intensely curious. And I’m just like, “Wow, that’s impressive. And that’s what I want to be like.”

HOFFMAN: 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 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, no, 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 can keep your optimistic mindset alive. If you succeed in this, then better futures are possible.

I’m Reid Hoffman. Thanks for listening.