Month: October 2020

Greetings Readers!

I find myself over-committed on multiple fronts for the next few weeks, so I’m temporarily hitting pause on this newsletter, using the nifty pause feature that Substack recently rolled out. I expect to be off for about 4-5 weeks.

For paying subscribers, this means billing will be paused until I hit the resume button. Which effectively means the next bill date on your current subscription will be pushed out appropriately. If you have 12 days left on a monthly subscription right now, you’ll still have 12 days left when I resume. If you have 289 days left on an annual subscription, you’ll still have 289 days.

You’ll still have access to the archives as usual of course, so you can catch up on stuff you might have missed.

(if this email feels like deja vu, you probably also subscribe to my other newsletter, Breaking Smart, where I sent out a similar pause notice there — I’m hitting pause on both newsletters).

See you all again in a few weeks!

I was idly wondering earlier this week about the classic time-rich/cash-poor conundrum, when a question struck me that I’d never really thought to ask systematically and seriously.

Why can’t time-rich people live off time capital the way cash-rich people can live off money?

By the paycheck benchmark, you have 40 hours/week at 50 weeks per year, or 2000 hours of time capital per year, for the rest of your life. If you think you’ll live another 40 years, you have 80,000 hours of time capital.

You can do more or less risky things with it (devoting it to earning a paycheck is incidentally, not the lowest risk thing you can do with it, just the simplest thing logistically), and get higher or lower rates of return on your time investments.

Of course, you only get time at a rate of 24 hours/day, but then even the worst failsons typically don’t spend all their money on Day One after getting their trust funds. So though there’s a drawdown rate limit on time, it doesn’t actually matter for most things you might want to do with that time. So there’s nothing fundamentally impossible about the idea of time capitalism.

So I decided to do some very simple and naive math to investigate it, in particular ignoring ALL ruin effects (where you run out of time or money along the way), and inflation.

Living off Money

First, let’s look at money, because it’s more familiar. If you start with a certain amount of capital, and draw it down at a steady rate with the intention of dying bankrupt, you get this formula for the sustainable drawdown rate at various rates of return. I think I derived it right. It’s been a decade since I did this sort of math:

And here’s a screenshot of a spreadsheet (here’s the link, feel free to make a copy and play with it) showing the sustainable drawdown rate as a function of interest under some assumptions ($5 million initial capital, a typical fuck-you money target). The first row is actually not 0% but 0.001% (at zero the formula goes to 0/0 so you have to take the limit).

Obviously, if you have zero risk tolerance, your sustainable draw-down rate, ignoring inflation, is simply the initial amount divided by the number of years. The lower your risk tolerance, the closer you get to that limit. In this case, 125k.

Less obviously, the higher the return rate, the closer the drawdown rate gets to living off roughly the annual interest (it’s because as the interest rate and number of years go high enough, the 1 in the denominator can be ignored and the drawdown is approximately the interest rate times the initial capital).

But the basic point is, if you can invest at higher return rates, your drawdown potential goes UP dramatically, as does your risk of ruin. Conversely, if you have a target lifestyle that costs more than the risk-free drawdown rate, you have to take risks to balance the equation.

Note that I have not modeled running out of money along the way, which will obviously happen if your initial capital is too low and your drawdown rate too high. Non-ergodicity and Russian roulette are a bitch, that’s life. But if you stay away from the gambler’s ruin limits, the formula is good enough to get a sense of wealth dynamics and what it means to live off of capital.

So far, nothing special. This is the sort of math wealth management calculators do in much more sophisticated ways. But here’s the fun part. With a little bit of algebra, you can get a similar formula for the required intrinsic yield rate per hour on your time.

Living off Time

Caveat: this is the absolute dumbest, laziest model of time capitalism I could come up with. My narrative interpretation of the variables is doing a lot more work than the math here. Possibly a better version of this formula already exists in some economics textbook somewhere.

Here’s the formula:

As you’ll notice, the formula is just the previous formula with some re-arrangement and extra terms (initial wealth has basically been modeled as time left in life). Again, we’re not modeling running out of time or money, or the fact that you can’t actually invest more than 24 hours a day. The point here is to get a feel for this beast.

Here’s how to read it. If you want to hit a certain income target by working a certain number of hours per week, you need a certain intrinsic yield rate on your time that implies a certain level of risk. Here, “interest rate” is not return rate on capital, but a sort of “return rate on all the time you have left based on what you’re doing in this minute.”

Yeah, a janky interpretation, but it was that or more complicated math.

Think of it this way: to work with a 5% “interest rate” on your time is not about working harder, smarter, or more skillfully. It’s doing riskier things with that time. Being bolder basically.

This time, the spreadsheet (tab 2 if you want to play with it) looks like this. Again the first row is not 0% but 0.001%.

Again, as expected, with zero risk tolerance, your yield rate/hour basically has to be your target income divided by the number of hours you’re willing to work. So in the example, if you want $2000/week and want to work 4 hours per week like Tim Ferris, well then, you have to make $500/hour for 4 hours a week for the rest of your life.

If there’s sufficient demand for your consulting services at that rate, and you expect to work till your dying day, you’re set.

But maybe your skills aren’t valuable enough in the market to command a $500/hour rate. Maybe you can only command $215/hour. But you’re lazy and don’t want to work more than 4 hours per week. So what to do if you’re both too dumb and too lazy to earn the lifestyle you want?

Well, you take risks and hope to get lucky. If you can’t work smarter or harder, you have to work bolder.

In this case, you’d better be taking 5% “interest rate” worth of risk with your time.

The return on that risk could show up in many different ways.

• Maybe you build an asset that delivers a passive income stream or rent, like a published book or a small web app.

• Maybe you don’t get any smarter or more skillful at what you do (quite possibly you’ve gotten dumber and less skillful), but people simply want to pay you a premium for the same work because you’ve somehow worked it so you add brand cachet. You’ve turned yourself into a rent-generating asset.

• Maybe you simply live really frugally initially and invest much of your surplus, slowly converting time capital into financial capital.

Think of Y as the pre-risk “intrinsic yield rate” on your effort, not the actual return rate. The returns of working with a certain level of smarts and energy.

If that’s confusing, think of it this way — the effort/intelligence required to buy a stock is the same in terms of simply navigating the UI of the trading website, understanding what you’re looking at, and which button to press to complete the trade.

But if you get a bigger return simply by investing in a riskier stock with the same amount of research, and getting luckier, the “intrinsic yield rate” on your time is still the same. If you were doing it with someone else’s money as a paid professional, and they simply told you “invest in high risk stocks” as their intention, and took on all the risk, you could probably charge that intrinsic-yield-rate amount as your management fee.

“Management fee for managing your own time” is actually a good way to think about the intrinsic yield rate. There’s a risk-taker-you who sets the target risk level, and then there’s the manager-you puts in the effort/skill/intelligence to actually execute behaviors at that risk level.

The risk level you take on has nothing to do with the intelligence or skill level needed to correctly execute the actions required. Buying lottery tickets is about as skilled a job as taking out the trash. It’s just much higher risk/return.

But the fascinating thing is how quickly your required yield rate drops if you’re willing to take risks. If you take risks corresponding to a 25% return on your time, you can hit your target income rate at just $50/hour yield… averaged over a lifetime that is, not instantly.

Another way to think of it is how quickly the required smarts drops with increased willingness to take risks. Let’s say it takes a genius IQ to consistently get $500/hour for 4 hours/week with no risk at all. Well, take on risk corresponding to a 50% “interest rate” on time, and you can make the same at $25/hour level of smarts, which might be completely average, based on the risk-free jobs you could typically get that pay that much.

I’ll try to think of better math and a better interpretation, but I think the picture is already clear with this cartoon version.

The moral of the story is that taking more risks with the same amount of available time, skill, and intelligence makes a huge difference. It’s the essence of time capitalism.

Time capitalism is about understanding the effects of risk-taking with your time so you can work with time-rich/cash-poor conditions.

For those of us without a big pile of initial capital to draw down, it’s the only kind of capitalism open to us.

The philosopher and theologian James Carse, author of the sublime Finite and Infinite Games, sadly passed away on September 29. It is an adjective I rarely use, but this is one of the rare books that deserves it. It also happens to be deeply relevant to the gig economy.

(James Carse. image credit: Simon and Schuster)

I was fortunate to be invited to a Zoom salon with Carse hosted by a friend just a few weeks before he passed away, so I got to hear his own thoughts on his life work and legacy at the end of it. The most interesting thing I learned at the salon was that he was actually something of a jock in his youth, a football player. His philosophy of games was rooted in actual games.

Gigs and Games

Carse was best known for a simple but powerful idea that is of deep relevance to the gig economy, best articulated by the opening lines of his book:

There are at least two kinds of games. One could be called finite; the other infinite. A finite game is played for the purpose of winning, an infinite game for the purpose of continuing the play.

Why is Carse relevant to the gig economy? For a simple reason:

Gigification is gamification. At its worst, it is finite gamification, and at its best, it is infinite gamification.

A lot of what I attempt to do in this newsletter could be described as trying to think about, uncover, and share the essence of this infinite-game aspect of the indie life. And help shift the balance in our lives as gig-workers away from finite play and towards infinite play.

So much of what is written about the gig economy focuses on the dark underbelly that it can sometimes be hard to see that there is in fact a positive, deeply playful side. Carse’s core idea helps us see the gig economy in a balanced way.

• The finite game aspect of the gig economy correlates to the under-the-API side of it. The world of algorithmically coordinated games, and very clear and literal game-like rules administered by apps that encourage you to “play to win” in a way that traps you.

• The infinite game aspect correlates to the above-the-API side. The world of self-defined work, autonomy, free agency, and stimulating variety. A world where you get to both shape the rules, and decide how to play in a way that frees you.

It is important to note that the finite/infinite aspect is not a feature of the game, but a feature of the attitude of the player. You know you are free when you are motivation is infinite-game-like: you’re playing to continue the play. Finitude or infinitude is primarily in your attitude, and only secondarily in the structure of the game.

So in principle, it is possible to play under-the-API games with an infinite-game mindset. It’s just harder. And of course it is possible to play finite games above the API.

On the paycheck side of the economy, it is overall harder to be an infinite-game player, but again, it is more about attitude than situation. There are definitely infinite-game mindset people in both the paycheck and gig economies, but I suspect there’s more of us on the gig-side.

Mercenaries and Games

Yesterday, I asked a question on Twitter that was partly a joke, partly a troll, and partly serious: if missionaries believe in mission statements, what do mercenaries believe in?

To my surprise, while there were some fun answers, nobody offered an answer that pointed directly at play, which is what I was hoping for.

Indirectly though, by pointing to the “game pieces” of business life — contracts, invoices, annual reports, book-keeping — people did sort of go where I was hoping they would. While the answers were clearly meant as pragmatic, perhaps even cynical alternatives to smarmy mission statements, they do reveal a lively spirit of gamesmanship (in a positive sense of what is generally a negative term) at the core of the gig economy.

Unlike many in the paycheck economy, we are deeply aware of the game-like elements because we have to be, and we possess perhaps a better literacy around them on average, because we are forced to. Forgetting that we’re in a game — what is sometimes called ludic immersion — is harder for us. But as a result, we are better at actually playing and enjoying the game. We see the game. We value the game. We don’t feel trapped by it. Paycheck employees on the other hand, often can’t see the game, don’t value it, feel trapped by it, and fantasize about quitting it for good (the “fuck you money” dream is a primarily a paycheck employee dream).

It says a lot about the negative valence that attaches to the word mercenary today that it is so hard to directly see the positive element of play at the heart of it.

As you’ll know if you’ve been following my writing this year, reclaiming the word mercenary with a positive valence is one of the things I try to do here (see The Way of the Mercenary from June 11 and Messengers of the Medium from October 1).

Here is my own answer to the question, which you may or may not agree with. Since, at its best, the gig economy is about infinite gamification, the mercenary equivalent of the mission statement is game rules.

I made up a yin-yang symbol to represent this.

Why game rules?

Mission statements (and their doctrinal cousins, manifestos) are serious things. The talk about values and future utopian states of the world. The very term missionary suggests a solemn — perhaps joyless — attitude towards work. Mission statements center seriousness. They are born of a sense of duty and scarcity.

Game rules, on the other hand, are about catalyzing play. It is about constraints you impose on your own sense of freedom to make your life more interesting. Game rules center fun. They are born of a sense of agency and abundance.

Good game rules make you want to keep playing and stay in an indefinitely perpetuated state of play until you run out of energy. Bad game rules hook your worst instincts and drive you to win, once and for all, regardless of what it does to other players, and arrive at a permanent win condition and never leave.

Again, there are no necessary structure-behavior links here, but something of a default tendency or bias.

• It is possible — but harder — for a company (and its paycheck employees) to be game-rules oriented.

• It is possible — but harder — for an independent consultant to be mission-statement oriented.

Companies are naturally constructs designed to catalyze seriousness rather than play, which arguably is why the work-versus-play dichotomy emerged in the first place. I suspect it was much weaker in the pre-industrial world. In the pre-industrial agrarian world, work and play blended in interesting ways, through religion, country fairs, harvest festivals, and the like. Industrial work separated the two. The gig economy is trying to put the two back together in a more powerful way.

The Play Instinct

One of the things I try not to do in this newsletter is to reinforce the bad us-versus-them idea that the gig economy is somehow morally superior to the paycheck economy. It is not. Each side needs the other side to exist.

But there is an asymmetric belief I’ll cop to holding: the gig economy is a more evolved way of working. The gig economy is as far beyond the industrial paycheck economy as the paycheck economy is beyond the agrarian economy.

This has nothing to do with moral superiority. Gigworkers are no more superior to paycheck workers than paycheck workers are to farmers. The evolutionary leap has to do with technology. The gig economy uses technology to organize work in much more sophisticated and fluid ways. That’s why it is more evolved.

My buddy Seb Paquet came up with an eloquent snowclone of Clarke’s Law to capture this idea:

Sufficiently advanced work is indistinguishable from play.

This is why it is easier to be in infinite game mode in the gig economy than in the paycheck economy. This is why it is even easier in the above-the-API part of it. It’s about more advanced technological modes.

But enabling technologies are neither necessary, nor sufficient. The nearly necessary, and almost sufficient condition is that you possess what I call the play instinct — the ability to see and approach almost anything as a game, preferably an infinite one.

This is where Carse’s life play comes into the picture. It is a book that can help you develop the play instinct by helping you ask and answer an obvious question about games: why do we play?

That question is surprisingly rarely asked, and even more rarely answered. It is as fundamental as why do we work?

A very rich understanding of what games are, and how to play them well, can be found in many places:

• Mathematical game theory

• Practical views of games in gaming industries

• Sports subcultures

• Huizenga’s excellent sociological theory of societies as games in Homo Ludens

• Anthropological understandings as in Clifford Geertz’ famous article on “Deep Play” in Balinese cockfighting.

• Hermann Hesse’s thought-provoking satire of gamified understandings of the human condition in The Glass Bead Game.

I recommend exploring all of these if you’re serious about a long-term career in the gig economy. But direct treatments of the question of why we play games are vanishingly rare. Especially ones that point to such simple, but powerful answers as either to win, or to continue to play.

Besides Carse’s book, I can only think of one other work that directly addresses the question — David Graeber’s 2014 essay in The Baffler, What’s the Point if We Can’t Have Fun? (Graeber too passed away last month, on September 2 — and though I’m critical of his main body of work on debt and anarcho-socialist politics, there is no doubt that he too was a seminal thinker for our times).

Developing an infinite-player mindset is crucial to surviving and thriving long-term in the world of work. It is important in the paycheck economy, but doubly so in the gig economy, where it is almost a make/break condition of a worthwhile existence.

There’s many ways to do it. You can experiment with your own gig-rules-making. You can become a contracts nerd. You can master your medium. You can explore the literature on games. You can actually play formalized games. You can design your own games. You can write consulting fiction like I sometimes do here.

But do it you must. Because the only way you can make the gig economy work for you is to learn how to play in it.

And there’s no better place to start than with James Carse.

It is revealing that that the term freelancer pairs free with lance. As mercenaries, freelancers in the Middle Ages were free of the missionary justifications that bound feudal lords and commoners to their intertwined societal fates, but they were still bound to the nature of their medium: the lance.

The lance was the medium of work and creative expression for the knightly class. Its message was death. And unburdened by any other sort of mission, freelancers were its clearest messengers.

In the Middle Ages, feudal knights were the messengers of capital (land for the most part), peasants were the messengers of community, and freelancers were the messengers of the most important technology of the day: the lance. Together, they sustained a three-way conversation between capital, community, and technology.

I think of this as the original Business Discourse. It is the conversation that happens around and within every business, from feudal manor to modern internet platform. It is like the Public Discourse on social media (often represented by the classic meme image of a chef), except for businesses.

The Business Discourse revolves around official statements by executives and employee groups, corporate PR statements, and “whistleblower” accounts and opinions leaked into the public discourse. Often it sparks storms in the public discourse too, but it is fundamentally a separate conversational theater.

Unlike the public kind, the business edition exists in a much more fragmented form, as a set of islands and archipelagos around individual businesses and sectors. But it does have its own gestalt. At any given time, there is a definite tone to conversations around businesses. This tone evolves gradually over time.

A particular small storm in the Business Discourse has been on my mind for the last few days: the publication of a blog post titled Coinbase is a Mission-Focused Company by Brian Armstrong, CEO of Coinbase, and the broad response to it.

The Business Discourse

The three-way partition of the Business Discourse, which emerged in the Middle Ages, continues to this day within every business.

Today, executive management speaks for capital, paycheck employees speak for community, and gigworkers speak for the technological medium (more on that last one later, since it may not be as obvious as the other two).

Customers, non-employee shareholders, and the general public, though they have a stake in the actions of a business, are not directly involved in the conversation. Depending on the situation, they might end up siding with any of the three active parties.

The lines have gotten blurred somewhat since the early industrial age. With the rise of complex and broad forms of participation in equity, it is no longer very meaningful to talk of management and labor for example. But it is still meaningful to speak of the three core messages in the conversation, and their respective messengers.

Depending on whether your compensation is dominated by equity, paychecks, or gig income, you’ll typically (but not necessarily) tend to speak for capital, community, or medium.

Lately though, one of the three groups has begun to dominate the Business Discourse: employees. Employee activism around political issues has grown steadily over the last few years (I did a more general thread about it in June).

The results have been decidedly mixed. I actually suspect mixed feelings about employee activism is one of the more recent drivers of people opting into the gig-economy as a Third Way.

Employee Activism

Employee activism started out as a useful check and balance to executive power, which around 2014, in the wake of the recession, was increasingly growing beyond the ability of stock markets, customers, or politicians to regulate. Employee activism briefly played a useful role: helping focus a certain amount of useful attention on issues like climate change, and abuse of social media platforms.

But increasingly, employee activism is confused, economically illiterate, rife with grifts and political careerism, and often hurts the causes it pretends to be about.

The Coinbase kerfuffle apparently started (correct me if I’m wrong, I’m going by twitter gossip) with a group of employees wanting the company to make some sort of public statement in support of Black Lives Matter a few months ago. Armstrong apparently resisted the call, and the blog post lays out his the general principles behind his decision: the company has a clear but narrow mission, and he believes it should not get involved in political activism outside of issues with direct relevance to that narrow mission.

Faced with a backlash following his blog post, he has since doubled down firmly, offering employees who want a more expansive political agenda (and a bigger voice in shaping it) a generous severance package to leave. It is unclear how this will unfold.

While I’m user of the company’s services, I don’t know any of the principals here, and have no idea what sort of person Armstrong is, or whether I’d like him personally. As a user, I think the company does a good job with its product.

But I happen to believe he was right on this issue, and did a few short Twitter threads in the last couple of days about it.

In general, I believe well-run companies, unlike well-run nations, benefit from an element of authoritarianism in their leadership. It’s good to have leadership that listens sincerely to all stakeholders, and aspires to service in a broad sense, but ultimately owns the decisions, along with all attendant risks and consequences. That’s what executive means.

A business is not a democracy or a political party. A business leader who aspires to lead by the logic of some sort of democratic employee mandate, rather than by the logic of the offering and its market, will soon have no business left to run.

To the extent the nature and conduct of a business is an expression of politics, it is naturally and necessarily an expression of the politics of its key executives. Otherwise it will typically struggle. Rank and file employees have limited say, and this is as it should be.

For employees, the primary means of political expression lies in their choice of employment, not in what they get to do within it. If you are a militarist hawk, maybe work for Lockheed Martin. If you’re a pacifist, maybe work for a vegan foods company. If you’re a climate activist, maybe work for a renewables company. If you are a climate skeptic, go work for a coal-mining company. If you believe you can meaningfully alter the natural politics of a business from the inside, by all means climb the career ladder within to positions where your voice can matter.

If you’re unhappy with the choices available to you, go free agent or become an entrepreneur to claim your own business-political voice in the Business Discourse.

Somewhere between 2015 and 2019, a lot of people became unhappy with the choices available to them, but were apparently unwilling to pay any sort of significant personal cost, such as would be involved changing jobs, earning political capital within the company, starting your own business, or going free agent.

As a result, employee activism went from being part of the solution to the problem of executive excesses, to being a problem in its own right.

The general public now has two problems.

Starting around 2016, employee activism began taking over the Business Discourse entirely. It began drowning out all conversation around the actual role of businesses in societies: providing products and services, building wealth, and turning technological advances into prosperity.

Unlike traditional labor, which restricted itself to issues of pay and working conditions at the particular business, this new breed of activism is often driven by white-collar workers, and has a very broad range of political issues it is interested in. Also unlike traditional labor, it bizarrely acts as though the actual business mission of a business is irrelevant, and can be safely made subservient to a broad political mission without any significant loss of economic viability.

This will of course play out as it will play out. You may or may not agree with my views above, but the point is, the Business Discourse is a thing, and interesting shifts are happening within it.

Depending on your politics, executives might count as good, and activist employees as bad, or vice versa. But either way, if you’ll pardon the bad pun, free agents are the medium element.

The question for us here on this newsletter is: what role should the gig economy play here? What position should free agents attempt to occupy in the shifting Business Discourse?

Good, Bad, and Medium

I have already argued, in previous posts, that in the politics of the workplace, free agents are essentially scabs (see The Clutch Class from Aug 29, 2019, and Return of the Clutch Class, September 23, 2020).

Not surprisingly, they tend to be caught in the middle in the Business Discourse as well. What role do they play in shaping it?

In my June 11 issue earlier this year, The Way of the Mercenary, I wrote:

And while history is often written by both winners and losers, it is rarely written by the mercenaries who shepherd its less glorious chapters towards resolution. 

This is of course a point directly relevant to us. The history of late industrial modernity may be written by/for/about the “kings and popes” of our time — CEOs and Presidents/Prime Ministers — or by/for/about the “commoners” (in the form of say the history of the labor or social justice movements), but it will not be written by/for/about consultants or freelancers. But as in the 1350s-90s, a post-pandemic period that very much resembles today, ours may in fact be the most significant role for a while, even if not recognized as such by the history writers.

Because freelancers today, as in the 14th century, are necessarily, definitionally, mercenaries. In the stories of history as written by winners or losers, it is the fate of mercenaries to be cast in a role that is worse than the good or bad guys in any account: shadowy figures who refuse to pick permanent sides, and subvert, through their very presence in the story, any claims to absolute rightness made by missionaries on all sides.

Then as now, mercenaries were simply outside of the false consciousnesses of the many mutually inconsistent missions they participated in.

How does this cash out in relation to the Business Discourse? It is clear what happens to executives and employees:

1. Executives like Brian Armstrong make politically loaded decisions and take on the attendant risks. Maybe key employees will leave. Maybe the product will suffer. Maybe enough customers will boycott the product to make a difference.

2. Employees might leave for other jobs, or to start their own businesses or gig economy careers. Or they might stay in good faith (accepting limits on their political voices at work) or bad faith (staying with the intent of somehow sabotaging the company).

Gig workers tend not to express their politics in either of these ways. By working for many clients, and shaping the scopes of specific gigs, they are able to hedge their political portfolios.

At the level of rideshare drivers, a driver who has two phones with Lyft and Uber apps open on them can make a choice at the level of a single ride which company to support. At higher levels, you can choose how much attention you give different clients, and what parts of gigs to say yes or no to.

One way to think of this is that that political allegiances of gigworkers are not monolithic. Through diversification, we can craft a better political voice for ourselves, at lower cost, than either employees or executives.

But the cost of this power is that we are more bound to the message of the medium.

Rideshare drivers must become both good drivers earning high ratings, and good at coming out on top in the arms race with the dispatching algorithm (for example, by choosing when to work based on peak and surge pricing times, and the types of routes available in different areas).

Web designers must keep up with evolution in standards. Programmers must keep up with trends in programming languages. Strategy consultants like me must keep up with broader technological trends.

They must, in other words, become messengers of their mediums. By voting with their tools, they contribute to the success or failure of different companies that share a technological base.

I for instance, have primarily been a messenger of the internet as a medium. A lot of my gigs over the last decade have basically revolved around the question of how to transform businesses in response to digital technology trends. More recently, I’ve become a messenger of sustainability technologies as a medium.

Being the messenger of the medium is not a trivial role. Often, it is the invisible but decisive role, over the roles of speaking for capital or community. Because individual businesses riding a technological wave might succeed or fail, but there is also an overall trajectory to the evolution of every medium, with a clear beginning, middle, and end.

To be the messenger of the medium is to be dominant in the endgame, when the nature of the underlying medium finally expresses itself with full clarity.

Media and Endgames

It is a commonplace observation that business sectors tend to be driven as a whole by the nature of the technological medium. In the opening, visionary companies tend to dominate. Medium effects are swamped by early path-dependence effects.

In the mid-game, fast-follower companies tend to grow and dominate the market overall (though the visionary pioneers may continue to dominate the narrative and enjoy a brand premium). Medium effects are swamped by mid-game capital effects.

In the end-game, as the technology fully diffuses and matures, low-cost leaders dominate the commodity phase, and medium effects finally rule.

Not surprisingly, the gig economy plays a progressively larger role as a sector matures, and more and more of the “medium intelligence” so to speak diffuses into the general economy. Startups typically hire few contractors and consultants. Late-stage companies typically have entire gig-worker ecosystems around them, shared with their industry peers.

Elsewhere in The Way of the Mercenary, I wrote:

Missionary beginnings showcase the aspirational best side of humans, but missionary endgames usually reveal the worst they are capable of. When missionaries grapple with each other in an existential struggle for dominance, they can lay waste to everything else.

Mercenaries are not heroes. But they don’t claim to be either. 

Mercenaries are not virtuous, noble people. But they don’t claim any particular virtue or nobility either. 

But often in history, they end up acting more heroically than people claiming to be heroes, and exhibiting more virtue and nobility in practice than missionaries. 

And not because they are better people, but because they have no choice but to do what they must to continue the game to natural and logical conclusions, long after the missionaries have smugly declared victory, or admitted defeat, and gone home. Because unlike the missionaries, mercenaries typically have to live with the consequences of their actions. They have no safe havens to retreat to once missions unravel, but the fighting continues.

Today, we are in the long endgame of one of the longest technological eras in history, driven by perhaps the biggest business technology after the steam engine: the internet.

As messengers of the medium, free agents are often heard the least, but their actions often matter the most. In the Coinbase case, it is noteworthy that the cryptoeconomy — a late-stage internet sector — is strongly shaped by a large number of open-source projects and legions of freelance programmers.

It is unclear how the story of employee activism will unfold in the next few years. We are living through some of the most uncertain economic times in living memory.

But one thing is clear: there is a hugely powerful medium approaching maturity, and we are its messengers. To play our parts in the larger drama, we must understand the message of the medium better than anyone else. Others might start various games, but it is up to finish them well.