Most of what gets shared as heartwarming stories are usually temporary, small-scale responses to systemic failures. I wish we found it just as inspirational to make structural changes to unjust systems, but I don’t know if our culture knows how to tell those stories.

The most effective and broadly-understand articulation of this idea is the phrase, “the purpose of a system is what it does”, often abbreviated as POSIWID. The term comes to us from the field of cybernetics, and the work of Stafford Beer, but this is one of those wonderful areas where you really don’t have to read a lot of theory or study a lot of the literature to immediately get value out of the concept. (Though if you have time, do dig into the decades of research here; you'll enjoy it!)

A potential negative aspect of understanding that the purpose of a system is what it does, is that we are then burdened with the horrible but hopefully galvanizing knowledge of this reality. For example, when our carceral system causes innocent people to be held in torturous or even deadly conditions because they could not afford bail, we must understand that this is the system working correctly. It is doing the thing it is designed to do. When we shout about the effect that this system is having, we are not filing a bug report, we are giving a systems update, and in fact we are reporting back to those with agency over the system that it is working properly.

Sit with it for a minute. If this makes you angry or uncomfortable, or repulses you, then you are understanding the concept correctly.

Through this lens, we can understand a lot about the world, and how we can be more effective in it. If we accept that the machine is never broken (except in the case of the McDonald’s ice cream machine), then we can recognize that driving change requires us to make the machine want something else. If the purpose of a system is what it does, and we don’t like what it does, then we have to change the system. And we change the system by making everyone involved, especially those in authority, feel urgency about changing the real-world impacts that a system has.

In my own life, I’ve found the greatest reluctance to embrace this idea, and strongest rejection of its obvious truth, comes from the politically moderate, centrist-leaning suburban folks that I grew up around and spent the first decades of my life amongst. Being from that context, I would probably still reject this idea if I hadn’t radically shifted how and where I live, so I have a lot of empathy for those who don’t want to engage with such a challenging concept. But it’s vital that we all do so.

Part of the reason I’m insistent about the POSIWID idea is because it’s a prerequisite for optimism that actually has impact. Mindless optimism says, “this system is supposed to have a good output, therefore if we support it hard enough, it’ll do the right thing.” But this results in people doubling down on investing in broken institutions, and organizations selecting leaders who become defensive and reactive to any challenge to the institution. These are systems organized around perpetuating themselves, rather than around any identifiable principle or goal. And you have to start with the principle.

We can be more effective when we fall in love with judging systems and institutions by the actual, real-world lived results and impacts that they have, especially the impact they have on the most vulnerable. Sometimes the stated values or purpose of a person or organization are useful in terms of judging what they have intended to do, but intent never matters nearly as much as impact, so we have to treat the actual outputs of that person or system as the ultimate truth when we assess them.

The next step, then, is to reflect on the systems around us now that we are cursed with the horrible truth that all of them are working correctly. Ask yourself, how do you get the power to change the system so that it wants something else, so that it can only inevitably do the right thing? Is there a reasonable path to that power? Or does that system need to be dismantled, so that it can be replaced by a system whose purpose is to do the right thing?

I’m not a Pollyanna; I don’t think everything is just magically going to turn out okay. But for the first time in decades, I’m seeing a movement that gives me hope. Call it the New Alt Media.

But first, we probably have to go back a little bit.

Finding a Voice

Early in my career, I was a middling web developer at The Village Voice. The paper was no longer at the peak of its cultural relevance by the time I got there, but it was still a platform that had meaning and reach. I got to witness first-hand when an incredible editorial team covered everything from niche cultural works that I was obsessed with to the biggest story of my young life, when we scrambled to keep the website running on the morning of September 11th.

Recently, my former colleague Tricia Romano put out an incredible oral history of the entire lifespan of the Village Voice, from its start in the 50s to its eventual shuttering in 2017. My tenure was somewhere past the middle of that run, but around the height of the alternative weekly era, when every major city in America had at least one credible, loudmouthed alt weekly offering up horoscopes and personal ads and a little bit of grief for the current inhabitants of City Hall. Tricia’s book reminded me of the context and culture that drew me to that newsroom, even though I was mostly just a kid in the corner peeking at the cool people writing about the cool things. It was a medium that meant something.

“Alternative” is a term that got diluted into meaninglessness sometime during the 1990s, but it’s worth remembering that it once had real significance. It’s impossible to overstate how stuffy and gated the major media of the day was. Alternative music genuinely was made up of songs that wouldn’t get played on the radio. And Alt Media covered topics, issues and communities that were erased from the institutions that shaped culture. As much as we rightly criticize major media for its biases and omissions and distortions today, those flaws were all even more extreme in an era when nobody even trued to hide the fact that they were just making their editorial hiring decisions on the golf course.

So the piercing of that bubble by raucous, unruly, messy alt media created by malcontents was genuinely powerful. To be clear, there were also always a whole bunch of assholes in the alt weekly world — this was still the publishing industry, after all — but every once in a while, a story would slip through the cracks and kind of… change everything.

For me it led to the revelation as a young kid growing up in the middle of nowhere that Prince’s ironic “All The Critics Love U In New York” somehow had something to do with those stacks of Village Voice issues that my best friend’s folks had in their rec room. By the time I made it through the Village Voice's front doors for the first time, I was broke, had almost no friends, didn’t have any connections, and half-bullshitted about my technical knowledge and promised I could make their website better. By the time I got canned less than 2 years later, the social media revolution catalyzed by blogs had taken off. The successor to, and destroyer of, the alt weekly era had begun to emerge. The blogger meetup in 2002 where I introduced Nick Denton to Elizabeth Spiers (they soon created Gawker as the first truly important social media publication), took place down the street from the Village Voice’s offices.

I hadn’t felt that same sense of “this is the future of media” since then, until just the last few months.

A Movement

There’s Flaming Hydra. 404 Media. Defector. Aftermath. Racket. Hell Gate. And so many more. This isn’t a new phenomenon — several of the publications in this broad category have been around for years. But we’ve reached a tipping point, for a number of reasons. The bad ones are obvious: the old news media is truly, finally dying. Distribution by social media collapsed as the neo-fash tycoons swept in. Something something AI.

But there are positive reasons that we’re about to see a truly significant cultural change catalyzed by the new alt media publications, too. Young, engaged audiences give a damn about working conditions for creators, so they like that many of these are workers’ co-ops, and that the rest are mostly non-profits that try to treat their writers well. After years of capture, digital distribution is returning to open formats like email and even the nascent world of the fediverse with its interesting potential for new delivery options. Paying for subscriptions for content has been fully normalized between Patreon and OnlyFans and Dropout and a lot of other human-scale media memberships. Many would much rather pay normal people every month than fork out for yet another corporate streaming service.

And all of that is without even mentioning the important part: these new platforms are telling the stories nobody else is. When local news is hollowed out, when vital beats are neglected, when algorithms are spammed with generative nonsense, audiences that crave relevance or humanity will naturally gravitate to the outlets that offer something real. That’s as fun and interesting and important as the impulses that drove people to first embrace alt media 70 years ago.

Look, I could talk your ear off about how the tech aspect of this alone improves the odds for these new publications. (Content management is business strategy! Open distribution platforms are fundamentally politically radical!) But the more important thing is that regular people, people who aren’t nerds who’ve spent two straight decades worrying about how insufferable writers in Brooklyn can make money publishing snarky but smart shit on the web, are finding value in this work.

And it’s not one or two successes, it’s lots of them. That’s what makes it a movement instead of a moment. That’s not to say they’re all going to work. We still haven’t even had the inevitable giant public flame-outs, or the attacks from the most venal oligarchs, but those times will come.

For now, I’m content to celebrate that we’re in the initial flourishing of an important new wave of media, a movement that will both provide necessary insight and also inspire a new wave of creators and storytellers. May the New Alt Media mean as much to its audience as the first era of Alt Media meant to its time.

An overview

First of all, what's the job of a board? Put simply, it's making sure the organization is running in the best way possible, covering everything from whether it has the right leadership, enough resources, a credible plan for the future, a good understanding of potential risks, and a vision for what it wants to achieve overall. The most common description of board members' responsibilities is that they have a fiduciary duty to the organization that they're serving. It's a common misconception to think that "fiduciary" exclusively means an economic or financial lens on things, but it's best understood as an ethical obligation to objectively do the right thing for the organization overall, not just for the bottom line.

At a practical level, boards function by having regular meetings (these will usually be on a quarterly basis), being responsive if there are urgent or emergency meetings or decisions that need to be made, and getting regular briefings on the operations of the organization both during board meetings and at other times as the need arises. The level of obligation and time commitment can vary a lot, as a new organization that's just starting up, or a company that's going through something dramatic like a leadership change or an acquisition can be extremely demanding of time. Conversely, there are a lot of organizations where some board roles are almost entirely ceremonial or honorary, as when a lot of non-profits name board members that help raise their profile or help them raise funds, but who don't spend as much time poring over operational details.

What do board meetings look like?

The actual mechanics of a board meeting offer a good glimpse into the overall work that board members are expected to do. A typical rough outline might look like this:

• Pre-briefing: A good leadership team will send a structured, well-written pre-brief ahead of every board meeting, outlining the current state of the organization including any recent major news or announcements, an overview of current fundamentals like the balance sheet and financials, an agenda of what to expect from the upcoming board meeting including necessary context for any discussions to be had, a recap of the minutes of the prior board meeting, and maybe a more specific deep-dive into any topics that the board wanted to focus on such as a strategic initiative or a specific challenge the organization is facing. The documentation part of a pre-briefing will often also be accompanied by personal briefings from the CEO or Executive Director to individual board members, especially if there are specific initiatives or efforts that they want to persuade board members to support in the upcoming meeting.
• Board meeting fundamentals: At the start of the actual board meeting, the executive leadership of the organization will usually lead the board through the review of the business fundamentals. To editorialize a little bit, the ideal here is that this should be the most obvious, or even boring, part of the discussion; if board members are being surprised by anything they see at this stage, that's a sign of poor preparation. Even if some of the fundamentals are bad (missing a fundraising or revenue target, slow growth, etc.) those are topics that should have been prepped well in advance of the review portion of the meeting.
• Departmental or functional briefings: Typically, the executive in charge will then delegate to individual members of their executive team to lead briefings about their lines of work. In a for-profit context, this will often be a report on sales and revenues; in a non-profit, this will be on fundraising and grants. Another executive will update on strategic work, like reporting on products or research & development, or progress towards strategic initiatives tied to the organization's mission. If the board meeting is structured by function, individual leaders who report out might be in roles like marketing, HR, or finance. If the organization leans more towards business units or departmental reporting, there might be a parallel structure where each person who reports out includes updates about things like marketing within the context of their own reporting structure.
• Strategic discussion: Most board meetings will dedicate time to matters of strategic concern, like how the current landscape of competitors or partners is looking, or how the larger economic or political environment is expected to impact the organization. Ideally, these are really open debates, but in a well-functioning organization, the goal is that the board is helping form a point of view that is being decided by the executive team, with the board in a supporting role.
• Organizational development: Good leadership will dedicate part of the conversation to how they're helping their team succeed. This can be everything from an update on hiring, news about any key roles that are being introduced (or asking board members to help recruit), changes in organizational culture or problems that have been identified, and progress against longer-term goals for areas like retention and employee engagement. This can also expand into focusing on areas of improvement in governance, or development of the board itself for things like creating committees and adding new board members.
• Business at hand: There will often be structural decisions for a board to make that must be captured in the minutes and recorded as part of the organization's accountability processes, whether that's major economic commitments, significant strategic shifts, approving key hires, or simply capturing functional decisions like updating bylaws and the like.
• Executive session: Finally, a board should have a regular session for those who are involved in overseeing executive governance, where they have a session without the CEO or Executive Director to talk about whether the overall leadership and strategy of the company is progressing as expected or if they need to provide feedback to the leadership team. In an extreme circumstance, this is where they would talk about proposing a leadership change.

Board meetings can be as short as a few hours for a small organization whose board is in tight, ongoing communication with the team, to a multi-day marathon complete with team-building exercises to bond the board together as a team and teach them more about the organization they're working to serve.

In the room, almost every board I've ever been on, nearly everyone in the room is deeply engaged and helping in whatever way they can. Because board members are often selected for specific areas of expertise (one person might be the marketing expert in the room, or be great at hiring), there are times when the conversation is most engaged with particular members, but in general there's pretty short patience amongst competent board members for others who show up unprepared or unfamiliar with the work at hand. There can be a slightly higher tolerance in contexts like non-profits, where there are often people who either are deeply passionate about the mission but perhaps less expert in some areas, or when someone is obviously in the room because they had cut a big check and everyone else is just indulging them.

How boards function

My perspective on boards is informed by my own experiences serving on them, but also by having been an outside observer and in coaching (or simply commiserating) with people who were preparing for board meetings. There are lots of different kinds of boards, and different kinds of board members.

Boards can range from a loosely connected group that assembled on occasion to indifferently rubber-stamp what an executive tells them, or they can be deeply and intrusively involved in an organization in a way that undermines leadership. Generally, they’re somewhere in between, acting as a resource that amplifies the capabilities and execution of the core team, and that mostly only helps out or steps in when asked to. It can be a very toxic thing to have a board that meddles outside of defined ways of interacting with the organization's leadership, but it can be an incredibly motivating and positive thing when people in an organization see that their board members are passionate and enthusiastic about the work they're doing.

Similarly, individual board members can range from figureheads who do nothing but have their name used by the organization to shadow CEOs who actually lead an organization while nominally only serving on the board. In all cases, the extremes are dysfunctional, but most organizations tend to be much more toward the middle, with a board that has a range of ways to help, and board members who do their best to be valuable in their area of expertise. Ideally, a good board is a mix of a broad range of skills, talents, experiences and perspectives that provides a set of capabilities to organizational leadership.

That being said, there are often obviously different agendas amongst different board members. For example, in a for-profit business, there are almost always board members who represent investors, and they are almost always completely unabashed about articulating the agenda they're promoting: a big return. I've been fortunate enough (and selective enough) that almost all of the investors I've sat next to in a board room are also keenly aware of the need to balance maximizing returns against longer-term goals that address the needs of workers and customers and community, but I've absolutely heard horror stories of investor board members who epitomize the worst caricature of a soulless exploiter trying to push the company towards its worst impulses.

There can also be really peculiar dynamics about power struggles that aren't rooted in diagreements over goals, but rather over personalities or agendas. If everyone agrees that the mission of the organization is to give everyone a cute puppy, but two different leaders have completely contradictory plans or preferences for how to make it happen, it can often turn into a lot of back-channel politicking that surfaces as awkward tensions or passive-aggressiveness in the board room. Being able to win over the board room can be a huge factor in determining who actually leads and succeeds in an organization.

How do you get in the room?

By far one of the most common questions I get when I've talked to people about serving on boards is, "How did you get in there?" There's a huge amount of mystique and (understandable!) skepticism about who makes up the board of directors for many organizations.

The first thing to know is, your initial impressions and suspicions are correct: it's not fair, and it's not nearly inclusive. I've been on 7 boards for organizations I didn't found, and 4 more for the companies I've started, and I think in every single one I was the only person (for example) who didn't have a college degree. The for-profit organizations were overwhelmingly comprised of very wealthy white men, with a small smattering of Asian American men, though the non-profits were notably better in nearly every dimension of inclusion.

More pervasive, though, is the old-boys' network. I got most of these opportunities due to relationships with people I'd had for years. Sometimes they were explicitly looking to diversify their boards (whether that was stated or not) and since I used to fairly visible in a lot of tech- or media-adjacent circles, I was someone they might think of to participate. It certainly helped that I had credentials that could also be read as performing respectability, like having had a "CEO" title. I'm not prone to insecurity, but I expect someone who is more normal than I am in that regard would definitely have felt some impostor syndrome when being in a room full of people who had almost all served on boards before.

I've always advocated for opening up the boards I serve on to be more inclusive, but there's a bit of a selection bias there, because any place that would let me in is probably already amenable to that argument. From talking to those who've served on more traditional boards, there's an almost uniform, reflexive dismissal of the idea, where legacy board members will assert that any class of people who haven't been in the board room before must certainly have been excluded on the basis of merit, as everyone in the room got there purely on their own skills and talents. It's bullshit, but I've heard it so consistently, in almost the same stupid "we can't lower the bar" phrasing, that it must be the common belief of the majority of people serving on boards today. And I expect that a lot of people who agree with the desire to make things more inclusive probably also feel the pressure of being the "only one" in the room, so they don't want to be seen as arguing for inclusion, lest they get treated as the token diversity hire on the board and have their other ideas dismissed.

This is probably the area where my board experiences vary most from a "typical" board member, so I unfortunately don't have a lot of specific advice to offer on getting into the room except that nearly every institution is going to want to see that credential or signifier that "explains" why someone is on the board, with the possible exceptions of founders, who get a board seat by virtue of their catalyzing work, but very often lack much of the other specialized expertise that outside board members bring in.

Broadening board participation is an area I've thought a lot about over the years. When I was CEO of Glitch, we began a process of seeking a community-nominated outside board member. Eventually we ended up stopping the effort, largely because people inside the company felt the board recruiting process was too much of a distraction. Not seeing that through is a real regret of my time leading the company; I'd love to help an organization try that approach again, and think about more structural ways that business leaders can intentionally make their boards (and board recruiting processes) more open.

What do I do when I'm on a board?

The thing I've read the least about is people's actual lived experience of serving on a board. My example may not be typical, but I think its not that far off from perhaps what a lot of other engaged board members do. I can outline the work at sort of a range of varying time scales.

• Daily/Weekly: I've got Google Alerts and social media monitoring set up for every organization, past and present, where I've served on the board, and I read virtually every press mention as well as every blog post or press release that they put out. My personal expectation is that if anyone outside the organization knows something significant about the company, then I should know it too, in the same time frame that they do. I've backed away from a lot of my social media engagement over the last several years, but for a long time I also tried to be an informal social media ombudsperson for the organizations I was involved with also, forwarding on any feedback or complaints or suggestions I saw to the appropriate parties who could respond or engage from within the team. This is probably the single biggest time commitment, but it's a lot easier since I work with organizations that I care about and would want to track closely anyway.
• Monthly: When organizations are going through a transition, or if I have particular skills that might be helpful for a specific project, I'll have checkins with leadership or the appropriate team leaders on a monthly cadence. These are often less-formal discussions, where I'm serving as a sounding board or giving feedback, but sometimes people will save up specific requests like introductions to particular people, or a review of a specific message or document, that they want to cover in those calls.
• Quarterly: The big one here is obviously board meetings. Generally, most of the organizations I work with spend about 3 hours, plus or minus, for a standard board meeting. I'll block out the time, cancel my other meetings, and also almost always schedule pre-reading time to review the board briefing documents a few days ahead of the meeting. Rarely, I'll ask for a quick call with the executives in charge if I have questions that need to be answered before the upcoming meeting. There's often a social component (the board goes out to dinner, or coffee with board members I want to connect more with) that turns these shorter meetings into the equivalent of a full-day commitment, but that's not every time.
• Yearly: Most boards will have one "big" meeting each year, when the board is expected to engage for a full day or more on board work. This can also often involve travel for an offsite meeting. That takes all the usual planning for a quarterly board meeting, plus a lot more logistical support. Most organizations will also usually have, at least once a year, some particular emergency or urgent issue that I need to help out on, so I budget for another day of rapid response each year for when unexpected things arise.
• Beyond: Even after leaving boards that I've served on, or when the organizations have transitioned to a new phase where they no longer have an independent board, I've almost always stayed in common with both the leadership teams and a few of my fellow board members. The mission and goals that brought us together are almost always still part of what we focus on, and if anything we all only have better insights to share over time, so I'm never surprised to get a text out of the blue from someone who I used to see in quarterly board meetings.

At a personal level, people who haven't seen me work up close are often surprised when we're on a board together. I tend to like the really wonky stuff, focusing a lot on governance (do we have the right tools for ensuring strong, steady leadership over time), financials (I end up on the finance commmitte, reading a lot of spreadsheets, surprisingly often) and on marketing/messaging and crisis communications response. Most organizations are very bad at quickly responding to unexpected outside surprises in a fast, humane, thoughtful way, and that's often when I get pulled in to help a team that may not have as much expertise. I've also worked to help a lot with transitions, like the inevitable moment when an organization matures into needing a new leader who's not the founder, or when someone who's been in an organization for a long time is no longer the right person to lead a key team after a strategic shift. Those things are really hard human moments, and very often the rest of a leadership team wants to support that person at a human level even if the professional transition is necessariliy painful. Maybe one of the things people would least expect is that, on a well-functioning board, much of the most vital work is really just about people, far more than about other concerns.

Of course, there can also be a crisis that arises from outside the organization like if a product is failing in the market or a major funder stops supporting the work. Those are different urgent problems, but also tend to be an "all hands on deck" kind of challenge, so everyone comes together to solve those things. In that case, I usually play more of a supporting role as a utility player if I can, since a big cause of stress can often by from having too many cooks in the kitchen at a moment when everyone is feeling the urgency of the problem.

How do you make a board do the right thing?

This is sort of the core question that people ask, in their own ways, about being on a board. If the stereotypical view of a boardroom is a dark-paneled room full of moustache-twirling villains planning their acts of villainy, then the thing we want to imagine is how we'd go into that room and stop them. In practice, the mistakes and harms are far more often the result of ordinary human flaws, and I've spent a lot of time thinking about how you anticipate those and work to prevent the worst problems.

For example, a big question to ask amidst all the reports and charts that one sees in a board meeting is: what's being measured? Are the right things being measured, and if so, are we doing so accurately? Which important things can't be measured at all? Who have we listened to or consulted in choosing what we measure?

Similarly, a key focus should be on what principle the organization is trying to achieve. Many alignment problems and strategy challenges come from people not having strong, clear agreement on those basic principles. It's a classic cause, for example, of when you see a cofounder "pushed out" of an organization they helped start. Very often it's not just their other cofounder(s) wanting them out — although interpersonal tensions and stress fatigue are a real thing — but also the board choosing one vision over another as they've started to diverge.

There's also making sure everybody has the willingness to call out the inevitable gaps between what we're trying to do, and what we're actually doing. This goes back to that whole idea of "the purpose of a system is what it does" — is our mission statement just a comforting myth, or is the organization really doing the work? This kind of question can be harder for a board to assess than it may seem, because they're always seeing the hardest challenges or biggest risks all the time. So things that can seem like an obvious shortcoming to employees or customers can be less visible or obvious to board members — especially if their primary way of getting information about the company is filtered through reports delivered by the execs who run that company. There's a distorting effect that's hard to get around, which is why I put a lot of priority on talking to customers and community members, and being open to having things surfaced by employees when appropriate. I think this is one of the most common causes of "why didn't the board know?" failures at organizations.

One aspect of making sure board members are thinking long-term and holistically is making sure incentives are aligned. Obviously, in a for-profit context, having investors at the table is going to skew things to focus on their concerns, so it's really key to have other players around the table. (In my experience, both VCs and institutional investors generally tend to work as a team with strong consensus about what they want.) But all kinds of anti-patterns arise from people being misaligned in a boardroom, especially if anyone on the board is just looking out for themselves, whether it's financially, career-wise or anything else.

Interestingly, good board members have many of the same traits as good employees: They're curious, genuinely interested in the larger goals of the organization, supported in speaking up when they see something going wrong, coachable when they're making a mistake or off-track, and fluent in the larger world or market where they're trying to have impact. Boards also fail for the same reasons that any other team at a company does: they get siloed or isolated from customers, the community, or the rest of the organization. They have their own goals or cross-purposes that they see as more important than what the larger organization is focused on. They put themselves ahead of the collective good, and act or communicate in ways that make them unreliable or undisciplined.

But in truth, very rarely does the problem in any given organization start or end at the board level. In very large publicly-traded companies, very often the board is just a set of people chosen by the executives to rubber-stamp their choices. In smaller public or larger-size private companies, the boards are often very dynamic with people rotating on or off the board, so the leadership of the company holds more sway over time. And in smaller companies or non-profits you have more of a mix of heavy-handed funders with less experienced board members who are still learning how to effect change in their organizations. That has the same impact, though: the organization's leadership sets most of the direction, and the board follows (and ideally offers support).

I've found a lot of people have a hopeful aspiration of thinking a board will come through and fix a problem that an organization's leadership has caused, or undo a mistake that leadership has made. Honestly, I think that kind of deus ex machina board action is extremely uncommon. A far more effective tactic may be to make enough noise that a board will obviously have to ask leadership about a particular challenge or problem that's come on their radar. (Note: this is not saying "just email everyone on the board with your complaint" — 99% of the people who do that are cranks, and it's easy to get grouped in with them if you use the same methods.) If you've organized a thoughtful, consistent, effective effort to point out an organization's efforts or flaws, making sure that your work gets in front of the board can absolutely be an effective way to make sure they ask executives about that issue.

That doesn't mean they're going to say "change what you're doing", though. And it definitely doesn't mean that they're going to immediately say "we gotta replace this exec". Since most boards see their role as being about supporting the leadership team, they're inherently conservative and biased towards the status quo. Changing a board's incentives and motivations requires straegic thinking about getting them to see evolutionary changes as possible, rather than hoping to jolt them into radical change unless there's a particularly extreme crisis.

Put simply, people don't join the board of an organization because they think it's broken and needs to change, except in the case of activists getting named to a board — and that's almost always activist investors whose agendas are brutally obvious.

What to take away

A board of directors is a structure that is about power in an organization. In its ideal, it's a clear balance against executive power, with a predictable schedule and process of operation, that provides a stabilizing influence over longer periods of time. In reality, well... it ain't always exactly that. The minor challenges are the usual human weaknesses and foibles, like distraction or greed or ego or ambition. The major challenges are structural, in being profoundly exclusionary and, in too many cases, corrupt.

I believe in the structure of a board (usually along with some separate advisors) to help an organization reach its fullest potential, in much the same way as I believe in governments having separate branches with separate forms of accountability and appointment. In practice, having nearly all-powerful executives select the membership of the organization that's meant to hold them accountable tends to fail just as badly in business or non-profits as it does in governments.

I don't necessarily think my experiences or point of view on serving on a board of directors are typical, but I do think that they can possibly be useful in demystifying an insitutional structure that far too few people ever get to witness. And I'd definitely urge everyone to think deeply about the role of these pervasive structures when considering how to change or influence any institution that matters.

Up next: Answering your questions!

I put out a call on my various social media channels and got dozens of really interesting questions about boards and being a director on a board. Instead of making this long post even longer, I'll be back with answers to all your questions. Stay tuned!

Speed round: Board stuff!

(I have quoted people's questions verbatim but am not linking directly to the askers just for the sake of discretion):

How active are different board members, on average, and are there any patterns that can help a company choose a successful board member?

As mentioned in the previous post, this can vary a lot — some folks may be there in name only to lend prestige, others might be super-involved. A great way to evaluate board members is to judge their engagement in the problem space that the organization is trying to help solve — are they there organically, of their own will, already? If so, that's a great place to start.

what to look out for when you’re asked to be on [a board], what are the red flags

I'd start by asking why they want you to join the board, and get that answer independently from different members of the board, as well as leadership. Comparing those notes will tell you a _lot_ about whether it's a good opportunity. If they talk about the mission and how you help them achieve it, that's great. If they talk about what's broken on the board and how you're the fix for that... well.

What is the *main* purpose of a board, given a company and its size, market, etc?

I think a lot of that is covered in the previous post, but broadly, in for-profits it's about enabling growth over time, and in non-profits it's about ensuring sustainability while working on a particular problem.

How often did you come away more (rather than less) impressed with the executive team than you expected?

In the organizations I've worked with? Every single time I came away more impressed with the executive team. Every time. Tons of thought, tons of heart, tons of dedication to the work. Of course there were individual exceptions where someone was a jerk or incompetent or whatever, but overall people care a lot about putting their best work (or, even better, their team's best work) in front of the board, and that is the overwhelming impression that I take away.

How much should you worry when you ask about the policy on [thing] and they laugh nervously?

That is a moderate-to-large-sized yike. Sometimes they're laughing because they've talked about it ad-nauseum and are aware it's an issue and are working on it. Sometimes they're laughing because they're aware it's an issue and they've all been dancing around it.

What signs do you look for to join, and what are red flags? When do you leave? Would you join a board for an org that is far from your core expertise?

Basically, I look out for alignment on mission, belief in the team, and an opportunity for me both to bring in my skills of what I'm good at and also a chance for me to learn a lot. I wouldn't join an org that's widely out of my expertise unless they specifically asked me because they were looking to broaden out.

when, if ever, is there real disagreement among board members, and how does that get hashed out

It's rare, but it absolutely does happen. As I said, sometimes it's just about everyone agreeing on goals but disagreeing on paths to getting there; that's not usually _too_ hard to settle unless egos get in the way or something like that. If it's a firm disagreement on vision/intent, eventually it almost always leads to the party that disagrees with the founder/chair/CEO getting quietly moved off the board.

as a board vp of a tiny nonprofit, I’m curious about how the experience differs from for-profit boards of various sizes.

Biggest thing is the shift in focus on resourcing and fundraising. It takes a lot more effort proportionally to support a small organization, whereas a larger org will tend to have that function professionalized, so then more of the conversation can be about strategy and the like.

How were you able to identify private company board seat opportunities? Did you work w/a headhunter that specialized in board placements? Besides monetary compensation, were there other types of compensation, perks offered for your time?

I identified opportunities based on my passion for the work the company was doing, or my belief in the founders. In many cases, I was doing board-level advising for their company for a long time, even years, before I was asked to be on the board. As I said, my experience is atypical because much of my opportunity arose from my visibility, but I've definitely worked with great board colleagues who came in through headhunting firms. By far the most common scenario is people networking their way into consideration. In terms of compensation, I've gotten equity in some of the for-profit boards I've been on (that's really only been material once, in the startup world it's mostly just working because you think it's worthwhile, and hoping it turns into something) but in terms of perks, I haven't done a lot of the "they fly you to Hawaii for a board meeting" kind of stuff. It does happen, especially in publicly-traded companies.

How much of the documents they send you do you actually review, vs how much is just listening to management and rubber stamping their suggestions?

I read all of it, every time, with rare exceptions. And I usually try to have good questions or notes on what I took away from the pre-read. Obviously, sometimes being busy or only getting the material shortly before the meeting can affect that, but having been on the other side of preparing those materials, I take it pretty seriously. (My "make better documents advice is based very directly on that experience.) That being said, I've definitely seen times when folks in a board meeeting very obviously didn't do their homework, and I find it pretty frustrating. Fortunately none of the boards I work with now have that problem.

Is it really just all about fundraising? Or are their positions that do other stuff?

This can vary a lot. Sometimes in scrappy non-profit world, it's definitely a "let's put on a show and save the orphanage!" vibe, but even then there are board members who aren't focused on getting dollars in the door. For larger scale corporate efforts, there's a revenue conversation every time, but fundraising or seeking out capital is a structured process that will usually (ideally!) happen on a predictable schedule, instead of being a constant scramble.

what are the red flags when recruiting and interviewing potential board members? (Or more broadly, what are good/bad ways to identify and recruit new members?)

Huge red flag is when executive leadership seeks out their buddies to be board members right after they didn't get their way on a major decision, _doubly_ so if that major decision was about executive compensation. If you're in the position to evaluate board members yourself, judging their curiousity for the work your team is doing, and their fluency in your particular concerns, is really key. Resume honestly isn't highly-correlated to how good someone is at being a board member, in my experience. And often it's very hard to see from someone's LinkedIn (or whatever) whether they're genuinely engaged in unsexy concerns like governance and auditing.

Is there any such thing as being on a Board and NOT being expected to personally donate $1k+?

Assuming this is in the non-profit world, it's basically a "Nobody rides for free" kind of situation. The more-friendly name is a "give/get", where board members are either expected to personally give or get others to donate to a certain threshhold. Again, there can be some exceptions to this, but honestly it seems like a fair expectation to make of folks; if you don't have the funds yourself, then do the work to help raise them.

Why is there such a persistent silo-ing of stuff happening at the board level of non profits from the staff who are affected by their decisions and how can it be fixed

This question kind of haunted me. I could write another 5000 words on it, but it comes down to the structural stuff mentioned above — who shares what information with whom at what time. I honestly think it's _rarely_ because people are trying to hide board decisions from workers, though obviously there are some bad actors in executive roles who do see their workers as subordinates who don't deserve transparency. Far more often it's the combination of people being busy (especially in non-profits, where so many are overworked) and people playing the telephone game with passing information along. The net result is still awful, so I wish a lot more organizations would just have an open session with the board after board meetings where workers can talk directly to them, or let workers nominate an observer representative to the board to share information out. There's very little, especially in a non-profit, that needs to be kept fully private.

I've read arguments that the culture of boards of dir's have changed over decades to facilitate members who always support very high and even excessive (relative to performance and/or profits regardless of inputs) executive compensation. Do boards seem like yes crews regarding ex comp?" Yeah, the boards of big publicly-traded companies have become absurd rubber-stampers on exec compensation. Part of it is the inputs the compensation committees will use to determine comp, which involve things like "we took a survey of exec compensation from everyone in our industry cohort.

Shockingly, looking at a whole bunch of companies that also have overpaid CEOs will result in you overpaying your CEO. Another factor is the meme-ification of company valuations, where recreational investors increasingly look at everything other than business fundamentals when assessing a company, which results in there being disproportionate impact from executive choices or changes. Executive candidates can leverage this to get more comp either by carrot ("the stock price will go up if you hire me, so I should get a cut of that") or by stick ("it'd be a shame if you didn't hire me at my desired salary and something bad happened to your share price").

What have you seen be most successful for effective onboarding of new directors onto a board? What are common, easily-avoided pitfalls for boards of expanding organisations?

One thing I've seen that works _great_ is letting new board members go through employee onboarding! It's a super nice way for them to build relationships with a team and experience the culture of the organization, yet it's extremely rare for either board members or companies to do it. Some of the easy gotchas are not properly briefing new board members on the "basics" of an organization and its work, assuming too much fluency coming in, and also not having a structured onboarding process for new board members that spans multiple board meeetings. Also, have more good ways for board members to meet the team beyond senior execs!

Do board members know when things are going south and do they say anything?

Depends how and when. Financially? Usually, and they damn well should. In terms of product or process? Maybe, but it can be hard to distinguish from the normal background noise of people complaining. For people and workers? Rarely, as this is the thing that most often gets masked by the organization, either intentionally or unintentionally.

As a singular member, you're literally powerless without gaining the loyalty of other members, yes or no? Also, what are the opaque means by which institutional leadership makes it impossible for boards to control behavior?

Not always, but often. You basically have to build coalitions of agreement to get boards to be effective at anything. Ledares can mask things from the board often just by controlling emphasis of information sharing during things like board presentations. So if there's a serious issue, they might mention it, but downplay the seriousness or say that it's under control, and then the board will rarely suspect that the problem is deeper than it appears, because it's not as obvious as "they were hiding this big problem from us".

Can a board limit excessive kowtowing to shareholder demands? Can they, in effect, protect the health of the company against too much profit extraction?

A good board will think in the long term, and I've definitely had conversations with board members who explicitly talk about resisting the "solely maximize shareholder value" trap. But that culture is fragile and hard to protect, and all it takes is one person saying "why are you talking about all that hippie shit?" and it can evaporate. It's very hard to figure out how to get boards to add directors who have character and courage to speak up on that stuff.

from what context did you join boards, how did those board positions come about?

There's a pretty wide range of answers for me on that over the years. It's ranged from the fact that I started the company or organization in question, so I pretty much _had_ to be on the board, all the way to being recruited by people who I barely knew, but who knew that I cared about the work the organization was doing. In most cases, there has been a long period where I help out informally or as possible, sometimes for years at a time before anybody ever approaches me about helping on the board.

What does a board observer do? As an Angel investor, can I negotiate one?

Board observer roles can vary a lot, but they're very common, especially for either less-significant investors, or for other key constituencies like employees or even strategic partners. The key thing about an observer is that they don't have any voting power, but additionally they will often be excluded from executive sessions and more sensitive conversations having to do with things like compensation or personnel or strategic (mergers, acquisitions, etc.) work. It's a great way to learn if you can get access to that kind of opportunity.

range of relationships with the CEO/founder (esp as founder owns more and more of company).

This can really vary. In relatively rare cases when things are going poorly, the board can be actively at war with the CEO or founder. This sucks, and often gets very petty and personal, and nobodhy comes out of it for the better. Conversely, when a hard situation arises (for example if a company is in danger of going under, or an organization has an existential crisis), a good board pulling together to all help solve the problem is one of the most rewarding and inspiring things I've seen in a professional context. As founders get more and more power — not just ownership, but also new forms of control like super-voting shares and taking over chair duties in addition to CEO — there are a larger percentage of boards that couldn't hold leaders accountable, even if they wanted to. This is the kind of thing where effective regulation could likely help shift things for the better.

how monetary incentives shape board involvement

This varies a lot as well. I've seen people nobly walk away from massive amounts of money in order to do right by employees or "forgotten" founders, or to keep an organization on a stable footing. It's far more common to see people, especially investors, be nakedly in favor of maximizing short-term returns, and sometimes they'll even unapologetically do so knowing that they're hurting the organization. This is _far_ less common with board members who are truly independently nominated, and for whom being on boards isn't the primary way they make their living.

how callous about workers can they get.

I've heard stories from founders who heard, firsthand, their board members say, "fuck it, fire them all" and seen how devastated they were about the level of heartlessness they were facing. It's much more common for there to be more nuance, and a range of responses, though very often the level of empathy they have for a worker is directly correlated to how much a board member identifies with the person who's being affected. Marginalized people are at higher risk when their board doesn't see them as real people who share the same priorities and concerns.

what % think AI will solve every problem (I've already heard some wild stories about this))

Hard for me to speculate, as the boards I'm on aren't prone to trend-chasing (they tend to be circumspect about technologies, and see them as things to be evaluated in a reasonable way), but in general a _lot_ of boards are prone to looking at tech through the lens of whatever trends are getting a lot of media attention. Very few people get to the place of having enough power to be on a board while also having the technical fluency to truly evaluate new technologies at the level that an engineer or expert might.

How is this work balance with real full time jobs? And how does the real job feel about it?

It takes a significant time investment. Most of the time that I've been on boards, I've been the cofounder or executive of the organization where I'm working, so people were already aware that I'd be balancing these responsibilties. And very often, the people who work closely with em see how much perspective and insight I can bring to my work thanks to having served on these boards, so they see it as a worthwhile thing for me to spend a few hours on during work time every quarter. I do also do a lot of my board duties on nights and weekends, so it's much more of a case of balancing my personal commitments than my professional ones. Still, it's inarguably a big time commitment, and it requires support from a day job to allow you to consistently take that time away.

How do you know you are "doing enough" to justify being on the board?

Founders or execs (or board chairs) will absolutely let you know if you're not carrying your weight on the board, unless the entire board is woefully mismanaged. I tend to try to set explicit expectations of my participation, and also to set scope (like "I'll weigh in on tech questions") so they can properly anticipate what I'll do in my board duties, and then judge appropriately.

How do folks on their first board act different then after there are people used to being on boards?

This is a tough one; by far most of the people I've served on boards with have been on other boards before, with the possible exception of founders. There's a level of experience that comes from having seen common problems before, and it's indispensable when the inevitable problems arise. Newbies are more likely to panic.

What is your typical time commitment for serving on a board?

I covered this in the previous post, but basically it's a weekly-or-so cadence of keeping on top of news or updates, a monthly cadence of talking to team members (probably only an hour or so of time there) and then a commitment of at least a solid block of several hours quarterly for participation in board meetings. In all, it's probably a full working week per year.

What are the entry points to this? What are the things you wish you’d known when starting out?

I think a great entry point is trying to be of service to the sorts of people who run (or start) organizations. They will remember who was consistently valuable and level-headed, and then just be explicit about being interested in board-level roles. I wish I'd known how much of it is reading lots of spreadsheets or financial records, and how much of it is just building relationships that are durable enough to hold when things get stressful.

How to identify the difference between a good board and a bad board.

In short, the culture and the results. Are they transparent, communicative, and consistent? Or closed and flaky and lurching about? Does the organization have a clear strategy and goals, and does leadership talk about the board in terms of a common mission that everyone is working towards? Or is there a murky plan, with a resentful or passive-aggressive leadership team talking about the board like it's a problem to be managed?

Maybe it's niche, but I'm interested in how you think about board development and growth, your experiences as a board member "tuning" the board to better serve the organization (fwiw my interest comes from the tiny non-profit side of the board equation).

Governance over time is hard! One of the most common areas of failure is in not rotating out board members or bringing in new people as the organization evolves. It's hard to tell someone who's been valuable over time that they're not longer the ideal person to serve on the board. But it's almost always worth the effort to do so.

how do boards effectively influence the running of the business without treading on the toes of the executives?

The only thing that really works over time is having a trusting relationship to be able to have direct, sometimes difficult, conversations. Trying to influence things "behind the scenes" only drives drama and increases the likelihood of failure or stupid mistakes.

To what extent has the false, inhumane doctrine that profit-seeking corporations must always prioritize shareholder stock value gains over any consideration, ethical or otherwise, captured the brains of the governing elite?

Like... 80 percent? Maybe 85%.

How much agency do you have in setting the tone of the company/org? When do you know it’s time to leave?

A board probably _shouldn't_ have that much direct impact on tone; that's properly the job of the leaders who are there every day. But they should be aware and engaged enough to help leadership make corrections as needed, or to encourage them to do so if the leaders are neglecting to make necessary improvements. It's time to leave when someone else could be adding more value to the mission — there are always lots of smart people who aren't yet in the room.

What does a good board look like from outside? What motivates the board member actions? Is sole purpose to hire and hold CEO accountable, or is there more? What does the power structure look like within the board, within the organization, and within society?

From the outside, it can vary, but definitely look to make sure that it's not just a bunch of cronies who all went to the same university, or who hop from board to board together, rubber-stamping each other's ideas. There will always be people with an obvious financial conflict on the board, try to keep that percentage low. Generally people are motivated by the mission of the organization, and many times an affinity for the founder and/or leadership team. Sometimes people are just looking for resume padding or to have a certain credential. Power structures can vary a lot, depending on how active the chair is (and whether the chair is someone other than the founder or chief executive), the number and effectiveness of board committees, the level of engagement of individual board members, and how healthy the organization is overall. Within those constraints, it's sort of just like any other team — everybody has their own set of strengths, and alliances tend to form around common goals or interests.

seemingly small decisions taken at board level can have far reaching consequences with time. Can you give examples of where this may have surprised you, for the good or the bad?

This is a hard one. It's obvious when big decisions (hiring a new CEO is tricky!) have impact, but smaller ones often play out over a much longer time scale, and are only obvious in retrospect after a big catalyzing event like an acquisition or IPO or merger or the like. At those times, it's easier to look back and reflect, and very often it's not a case of "oh, we shouldn't have done that", but rather "because we made that decision at that time, instead of 6 months later, that's why we've ended up in this situation".

how do boards differ in American vs European contexts?

I don't know enough to answer this authoritatively. I've very seriously engaged with the idea of serving on one or two boards for European organizations, but have never actually served, so I don't have first-hand knowledge that would make me comfortable answering this.

I was recently elected to a tiny nonprofit's board. Which of the things I will learn will transfer to other kinds of boards?

Almost all of the procedural and structural stuff will be analogous to other boards. The rest depends a lot on how similar the other organizations are in mission, structure and maturity.

How do boards typically take in feedback?

From founders or execs, there can be varying degrees of formality, from side conversations at a board meeting to much more structured processes that work like a 360 review for a manager. If boards are soliciting feedback from other parties, like workers in an organization, there will usually be some kind of organized system so proper chains of command are respected, or so that disclosures or concerns can be addressed appropriately. A lot of boards to seem to operate in a vaccum, though, honestly.

When are board members compensated and how/why? (I'm not expecting money from either of my nonprofits but it's basically a second full time job for some people)

For non-profits, this can vary a lot. It's rare for compensation to be very substantial except at very well-funded, very large non-profits. I've never been paid for any non-profit board I've served on, though a couple times I got a nice dinner. In for-profit land, it can vary a lot, but basically startups do it almost entirely with equity and mature organizations have an entire board compensation process that resembles the usual executive compensation packages and incentives.

I'd want to know what encouraged you to serve on boards and (for the times you left and did not just cycle off, if there were any) what made you decide to leave.

Every time I've done it, it's because I believe in the mission and the team. I've left usually when there's a natural new chapter for an org, like significant structural or leadership changes, though in recent years it's become more common for me to step back as I focus on changing in my life or career.

I’ve always wondered how people who are on multiple boards manage to stay even somewhat informed about what’s going on in that many entities all at once. Like, isn’t that exhausting? Or are most members only aware of what’s happening on a "got a briefly right before the meeting" level?

I can only speak for myself, but as I mentioned in my earlier post, part of what I _love_ about being on boards is staying abreast of everything that's going on. It's like constantly getting to learn about a really challenging problem or interesting area of study, often alongside really smart people that I like a lot.

What training or skills do you find board members need to be useful?

I basically kind of wish every board member had the same training that I wish every high schooler got: basic sales training, how to read a P&L or a 990, enough coding to write a simple web app, some core fluency in how public policy about regulations in their domain work. Very few people take the time to learn that whole menu of things to even a basic level of proficiency, but anyone who's done each of them and kept up with a reasonable level of capability in those areas over time has a huge leg up on those who aren't curious enough to do so.

My general perception of boards is that they get the "great and the good" (people with a name, "grandees", you know) to sit on them but generally just rubber-stamp decisions. Am I wrong?

It depends a lot. There are definitely dusty old organizations where that's true, but then those places don't tend to include someone like me, so I don't have as much visibility into their cultures.

aside from being a sinecure for rich people, what does a board of directors do for a company?

Have I got a blog post for you!

If I'm looking at joining a mature startup as a sr employee, what should I look for in a board that shows that they know what they're doing?

I'd see above, "How to identify the difference between a good board and a bad board."

If you're an employee at a company, and you think the board is making dumb decisions, what is the best way to give them that feedback (and supporting evidence)?

This is a reall hard question to answer well, because the answer varies a lot. If there's an ethical or structural concern, a board will ideally have a whistleblower policy and process in place that you can take advantage of; these are generally pretty well run and can be surprisingly effective. But if it's more a case of "I disagree with our strategy", then... well, that's really, really hard. The overwhelmign bias of the board is to work with leadership, so even if you just decided to YOLO into the boardroom with a manifesto or PowerPoint saying "here's all the ways you're fucking up!" they're still almost certainly going to tell you, "okay great, go show this to your boss". Short of organizing workers, it's very unlikely a single person is going to upend the org chart through a direct entreaty to the board.

I'm curious how you think about your influence over the organization. What influence you have and how you learn enough in a limited time to give effective leadership.

As I said above, a board probably _shouldn't_ have that much direct influence, except in cases where things are really off track or they're asked to engage. It's much more about supporting leadership or encouraging leadership to reflect on their shortcominsg.

All my experience on non-profit boards has involved a ton of fundraising, something that makes me deeply uncomfortable. How do you navigate that requirement, particularly for non-profit boards?

The shitty but mostly-true answer is, you should get good at selling. Most non-profits are woefully unprofessional around many aspects of fundraising, and the kindest thing you can to to help as a board member is to take on some of that burden. Most boards will have a give/get requirement for precisely this reason. I personally like being expected to prove my value on the board at that level, not just through my direct work. I do sympathize that it's a very uncomfortable role for a lot of people, though.

organisational patterns and anti-patterns of boards. I suppose there’s a bit of Anna Karenina principle, but I’ve for example seen in a few boards how destructive it can be when board members try to corner each other instead of focusing on the organisation’s goals, which leads to burnout and factionism.

As I've said a few times here, the biggest anti-pattern is when you have a back-patting old boys' club in the boardroom just rubber-stamping each other's work uncritically. The toxic team-picking thing can happen, too, but that's usually much more a symptom of an organization that's going through hard changes; a company or non-profit that's running really well doesn't usually induce board members to dissolve into petty grievances.

What are your fiduciary and legal obligations as a board member, and when/how does that change for different kinds of organizations?

Mostly covered in my prior post.

I'm on a nonprofit board, and I'd like to know how it differs from a for-profit one.

Honestly, the most common difference is that the majority of non-profit boards, especially if they're larger or more established, will have some people on the board who are either not very experienced or who wouldn't make the cut in a for-profit context, but are there because they're true believers or were valuable along the way. That's not to say there isn't merit sometimes in giving them a board seat out of loyalty, but for-profit boards are generally far less sentimental about that. Then there are different structural and reporting concerns, and some vagaries of employment or fundraising law make the functional processes in a board meeting different, but that's more like switching between a Mac and Windows, everything is roughly familiar even if none of the small details are exactly the same.

Curious how much boards are in the loop with cybersecurity issues and if that has changed at all in the last few years.

There's almost always a review of risks and the organization's risk posture, and cybersecurity will certainly almost always be on that list. Levels of fluency vary, but again, a lot of board members are absolute boomers when it comes ot their level of technical expertise.

What do you do with all the checks they throw at you?

This question made me realize that I've technically never gotten a paycheck to be on a board. I've gotten equity in organizations (and, uh... _paid_ a lot of money to be on nonprofit boards), but the timing or opportunities never actually lined up for the various paid board roles I've considered over the years. 🤷🏾

What percentage of board members are also c level execs at very similar companies?

A _lot_. They can't be execs at directly competitive companies, of course, but it's absolutely the most common category of board member after investors and founders.

What's your favorite committee to be on?

This depends a lot on the organization and its stage of maturity. Certainly exec committees can be great for getting to work closely with CEOs or founders, and I tend to have been on a lot of audit or finance committes, I think mostly because I'm pretty willing to do that and not everybody is as willing or able.

Do think executives are generally honest with their boards?

The vast majority really are, in my experience. They might put things through a more positive lens, but it's actually pretty rare to be outright dishonest because the board is one of the few entities that could actually just get them fired for lying.

If the boards you’ve been on are responsible for hiring/firing the top brass (ie CEO): has being involved in that process changed how you view those leadership positions?

Leadership transitions are _always_ hard, even in the friendliest and most seamless of situations. I already have a ton of feelings about that that because I've been a CEO multiple times (though never at the scale of those running the organizations whose boards I serve on) but I have a shocking amount of empathy for people in those roles because very often bringing someone great in involves taking someone great out, and in many cases it's only because the organization has reached a new level that requires new leadership as a _direct result_ of them having done a good job. Like, you did so well in your role that someone else gets to have it now. Especially with founders, whose very sense of self or identity is often tied to the organization and its mission, that can be a heartbreaking conversation, even if everyone is doing their best to be kind and professional. I've said many times that being a CEO kind of almost _requires_ people to become a sociopath, because they're so inured to the power they have over others, but that doesn't negate that it's very real and very human for them to have a similarly stressful experience when they're on the other side of the power equation.

Phew! I hope this helps clear up a lot of the most common questions, or answers some of the more esoteric curiosity that people have. Thanks to everyone who shared their questions about boards!

First, a disclaimer: I am, by any conventional measure, very well-off myself; I can afford to live in New York City with a family. Compared to the prior generation of my family, who were raised in a very poor rural village without running water, electricity, vaccines, or other fundamentals of a stable life, I am aware that I'm incredibly fortunate. But, like you, I have to think about how much something costs when I buy it, and am aware of a budget when making plans, and worry about sending a kid to college someday. For the purposes of this piece, I'm talking about the people who don't have any of the concerns that we do.

It's important to understand in this context, nobody ever becomes a billionaire by mistake. They have to have really, really wanted it. Generally, they have to have wanted it more than they wanted to preserve any relationship in their lives, more than they've wanted to be happy or at peace. (Or, they inherited it and it didn't even occur to them to give it away.) You don't have to take my word for this; just look at the family relationships and friendships of the richest people in the world, and ask yourself how many of them resemble the most stable, fulfilling, rewarding relationships in your life. If you say to yourself, "I would easily give up a billion dollars to make sure my kid knows that I love them and want the best for them", then you are different than, say, the richest person in the world.

The Water Flows

So why do they pursue this life-destroying amount of wealth? The analogy I always come back to when discussing the ways that the ultra-wealthy use money is to think about a firefighter. Their job is to point the water (for the purposes of this analogy, we're assuming it's not a grease fire) at the flames until they go out. The task at hand is aiming at the flames, not determining how much water is left; indeed, it's explicitly someone else's job to build the fire hydrants and ensure they have sufficient water supply. And after the fire is out, virtually no one will ask them how many gallons of water they used, as that's irrelevant to the thing they were brought in to do.

For the ultra-wealthy, money is effectivey not finite. It's just a resource to be pointed at any burning thing. I know you're looking at your banking app saying $broke and wondering, "how can this be?" and yet: it is true. The most counterintutive thing is that, not only is the money faucet boundless for them, but in fact, most of the money coming out of the faucet is not their own. People who control large pools of money are very, very eager to let billionaires use their money.

Once we understand this fundamental difference, everything becomes clear. Having access to a nearly limitless flow of funds lets you exert power over things that can be controlled by money. And that's a lot of things. In economics, there's even terminology for the different ways of looking at resources: stock and flow. For you, money is a stock, a bucket of dollars you can carry, and that you try to make sure isn't empty. For the ultra-wealthy, money is a flow, it's just a hose of dollars that you can point at anything that isn't suiting your preferences.

With that context in mind, revisit your assumptions about how the ultra-wealthy influence things like policymaking and social norms. Even in the most positive, charitable case, you may wonder, "If this person has a bilion dollars, why don't they just pay for [good things for people in need]?" But in many cases, even if they were inclined to help with that particular cause or need, dropping a large sum of money at a particular moment would require them to treat their money on hand as a stock instead of a flow, and that reduces their economic power over time. In a nice framing, this is about ensuring they're leveraging other people's money over time to sustain their ability to give to that cause. Put more cynically, you can't exert control over something if you've already stopped paying for it.

The next time you're trying to understand the decisions that the ultra-wealthy make when they are attempting to shape our world, challenge yourself to rethink the assumptions you may have about the way that they use money. It is a fundamentally different tool for them than it is for anyone who only has a limited bucket of bucks.

• The only tools and technologies that will be described as “AI” will be recent, commercial, large-scale generative AI systems built around LLMs, mostly those where Sam Altman and Bill Gates have a direct financial interest. There will be little to no mention of the decades of learning systems that come before, no discussion of public models of ownership or control of AI technologies, and the only state-led efforts to create AI that will be mentioned will be framed as an arms race against China, even though the vast majority of historical AI research in the U.S. has relied on public dollars through either academia, the military, or both.
• Threats and risks around AI will be discussed in terms of “replacing” people in creative jobs, or contrived future scenarios like AGI. Even the discussion of AGI will rely entirely on definitions set by commercial interests like Altman and OpenAI. There will be no mention of the repeated attacks on labor that have been systematically funded as “tech innovation” in recent years, including the gig economy, blockchain and crypto hype, and attempts to push the metaverse and thoughtless return to work. Despite the fact that nearly every movie and TV set that Oprah has ever worked on being a union shop, not one voice representing labor will be quoted, and there will be zero mention of the fact that young workers are adopting labor organizing faster than they’re adopting AI.
• The word “consent” will never be mentioned, let alone the concept, when it comes to training data and surveillance data used to build large-scale models. No mention will be made of large tech companies violating the law to access data sets without permission to train LLMs, nor will there be any discussion of the unilateral changing of policies and terms of service to force billions of users into contributing to LLM models without consent.
• Errors, confabulations, and intentional lies and distortions produced by generative AI products will not be described as bugs or defects, but by the false marketing term of “hallucinations”, with no mention of any legal or moral obligation to make commercial software that functions in reliable ways.
• There will be no mention of the fact that large learning models are being used as a method of determining who gets killed in military (and militarized policing) engagements today, or how “the AI makes the decision” is a tool for avoiding accountability for violence that these systems help incite. Not one person who has had a loved one targeted for sentencing, violence or death will be quoted or spoken to in any context.
• The intentional blurring of lines around the definition of “AI” — encompassing everything from improving lighting in camera phone photos to drone targeting for missile strikes — will be ignored as if it’s an unimportant consideration.

In short, Oprah is making a commercial for some AI vendors, without disclosing whether she has any financial interest, and will close by wrapping it in the same kind of feel-good woo-woo bullshit she used to platform some of the most murderously dangerous anti-vaxxers of the modern era. We can do better. She should feel obligated to do better.

At the time, I worked at the Village Voice, which was the most famous alt-weekly media outlet, a then highly-influential news outlet for people who cared about culture and the arts and progressive politics. I suspect that much of my perspective on the day and the days that followed were informed by working in a newsroom alongside people who were witnessing the most dramatic aspects of the event.

I’d gone to bed at 2 or 3 in the morning, working on some problem with the website whose specifics I’ve since forgotten. I didn’t remember to turn off my alarm, so it went off as usual a little before 9AM. My alarm was set to play a local radio station, and as I started to wake up and get ready, they interrupted the broadcast to mention that a plane had hit one of the World Trade Center towers. It was mentioned like a serious traffic crash, something significant but not overly worrisome; there were always small planes around NYC airspace and it wasn’t that unusual to have accidents from time to time. Until a few months prior I’d worked at the Empire State Building, and one of the first bits of lore they shared when you worked in the building was about all the weird incidents with planes and dirigibles that had tangled with the building. I didn’t honestly think much about it, and assumed it was some hapless private pilot that had messed up while sightseeing.

Just a few moments later, it was clear that every single thing had changed.

I turned on the TV when I heard the news, a method of getting information that dated back to my 20th century habits, but which I would soon permanently discard. Every channel had changed over to a live broadcast of the burning towers, with all manner of confused response and very careful, measured language accurately describing only what was painfully obvious and clear, with a noticeable attempt not to speculate. I was in my apartment uptown in Spanish Harlem, and my roommate had already gone off a while earlier to his office in midtown.

I sat down on my couch with my laptop and started to see what I could find out online, and instantly my messaging app (in those days we used a tool called AOL Instant Messenger, where each new message from a different person got its own window on your computer) had blown up, and my screen was covered in brief messages from online friends checking in. Almost nobody in the U.S. used SMS or text messaging of any kind back then, and people you knew "online" were considered a sort of different, not really real relationship. So I cared about these people, and they obviously cared about me, but there was a sense of stigma or distance to the fact that these were the folks who were checking in on me. Though my first reaction on the day was to thank everyone for checking in, the feeling I remember most was from a few hours later, when I felt so desperately alone and deeply wished I had someone to hold on to. I had gone through the usual sorts of relationship dramas one endures in their early 20s, and had been through a breakup not long before, and the profound sense of not having anyone around was pervasive. Later, many of the people who checked in on me that day, who'd been those "imaginary" online friends, became the people who introduced me to my wife, who greeted my child, who held me when I grieved, who rejoiced as we built careers and lives together.

Shortly after the news had broken, I had gone outside into the street. We all did. Everyone poured out onto the sidewalks and into the streets themselves (all traffic was shut down in a way that we wouldn’t see again until Covid hit). We were in the parks and at the subway stations, lined up at the hospitals to give blood, and by later in the afternoon, lined up at the mosques in the neighborhood to stand guard together. I spent a while at a nearby bodega joining a few people who were handing out glasses of water to the dust-covered folks who had by then walked all the way from their offices downtown, still shell-shocked and with everyone fruitlessly asking around for a phone that still had service. I’ve still, to this day, never hugged as many strangers as I did that afternoon.

By later in the day, a few friends in the neighborhood had reached out, and my roommate came back home. He had watched, through the window of his office, the second tower fall. Not on TV. Not on video. He’d seen it firsthand, as it happened. Later I would find so many more friends who had been through similar trauma, let alone those who had loved ones in the towers. A thing that’s been lost to time in the many years since is that, for quite a long while, we thought the towers had already been full of workers that day. Tens of thousands of people might be in the area at its peak occupancy, and we were fearing, maybe even assuming that casualties would number that high.

That wasn’t the only thing we were wrong about. Everything in those first early days was focused on rescue, on recovery. People were mobilizing dogs and equipment and medical teams, and the reason everyone was giving blood was because of course they were going to find survivors. They were going to find those miraculous stories to give us hope. By a few weeks later, long after I’d stopped watching televised news, they were doing stories about how they had volunteers pretending to be survivors who would hide themselves in the wreckage of the collapsed towers, so that the dogs could "find" them, in hopes of keeping the rescue dogs from getting too depressed.

Love’s In Need of Love Today

But amidst the obvious, overwhelming grief, my strongest memory of that time was of a feeling that can only be described as a deep and abiding love. There was a profound, shared humanity, and extraordinary kindness was shared between complete strangers on an unconditional basis, for days and weeks on end. It sounds like a fairy tale, or the kind of thing that happens in a movie, or that would get dismissed as impossible by the "smart", cynical view.

It really did, happen, though. People went through an unimaginable trauma, and an impossible circumstance, and we genuinely spent hours or even days thinking it might be the end of the world, and the reaction that happened was that people came together spontaneously to take care of each other in ways both minuscule and profound. The worries seem so extreme with all the time that’s passed, but a thing to keep in mind is that, at that time, very few people had ever gotten their news on the internet before. They were just watching cable TV or reading newspapers. Suddenly, they were constantly updating the windows they had opened to different news sites (browsers didn’t have tabs yet) and they had no idea how to discern what was valid. If you think today’s boomers get their brains fried by Fox News and Facebook, imagine people a full generation older, some of them born before electricity was widely available, getting completely unvetted and unfiltered messages flooding their email inboxes. I’m not surprised that it only took one day for me to begin angrily posting about misinformation. Especially when rumors involved the security dog at the Empire State Building that I had become friends with.

Despite that chaotic information environment, the deep and abiding memory I have of the time is of New Yorkers extending each other an unimaginable kindness, grace, and compassion. On the day, there were grand gestures of giving people a place to sleep, or a change of clothes, or packing up food for someone who they had never met before so that they’d be able to eat as they tried to figure out a way home. But there were smaller things too, like people pushing a tired mom’s baby stroller through the beautiful early autumn weather, or what looked like almost a parody of interfaith harmony as people of different religions gathered to worship and spend time together, each dressed like an illustration in a kids’ storybook. It would be dismissed as unbelievably corny now, but people got together to sing things like the national anthem or God Bless America and it was perfectly earnest and heartfelt and even appreciated. Part of what was so amazing and what left such an impression was that everyone let go of their cynicism and everyone was brave enough to be vulnerable.

By the time they did a telethon fundraiser for first responders a few weeks later, it opened with Steve Wonder doing his wonderful classic, "Love’s In Need of Love Today", and I broke down in tears again, because we had finally arrived at a moment where it felt like everyone around me, everyone I saw on the street, was living the kind of pure and idealistic reality that he had always been singing about.

That was the emotional context, but there was also the visceral, sensory experience of being around those days. The most pervasive part was the acrid, searing smell of electrical fire, from the smoldering rubble pile that would keep burning downtown for the better part of a year. It pervaded everything, and you could be almost anywhere in town and the wind would change and then suddenly the smell would catch you off guard and you’d be crying again. Anyone who says they were here then, and doesn’t mention the smell… well, they’re flat out lying.

Every public space was papered in flyers listing those who were "missing", all in similar designs, featuring whatever photo people had most recently scanned of their loved one. In those first 48 hours, every subway stop and telephone pole and bus station was covered, and then the thin copier paper almost immediately began to break down. The decaying and torn posters with photos of people’s loved ones were reduced to tatters just as quickly as we all realized that nobody would be getting dug out of that rubble pile.

It only took days for public spaces to be fully occupied by soldiers with long guns, a full occupying force that was the first sign of the new militarized reality that broke through the camaraderie and care that everyone was showing to each other. Though I had stopped watching TV, I knew from walking by store fronts and overhearing conversations that the rest of the country had fully moved on to beating the drums for war and violence, using our city as their pretense. I grew increasingly protective and defensive about New York City, about what it means to those of us who live here, and to this day I have a white-hot resentment of how our town’s grief was used to justify hateful violence without our consent.

Everything After

You know the rest. You used to be able to go to greet people at the gate at an airport. They lied about Iraq and killed countless hundreds of thousands of innocents. Technological surveillance became the default expectation for everything we do, public or private. They made the cops into an army, all across the country. A thousand beautiful potential futures were thrown away. I wrote to my senator, saying "we could stop driving to work one day a week and never need Saudi oil again, and fight global warming!" (I didn’t call it "climate change" yet.) By the time I got an automated response, we were already at war and the postcard said "we support our troops".

In my own technological world, everything changed in a leap, too. Suddenly everyone knew what Google was, and that some people were sharing news online. The strangest part of working in tech was that, as my friends and I launched one of the first big blogging platforms in October of 2001, that same month the original iPod and Windows XP came out., meaning the first very primitive outlines of the online world we all live in now came into view while we were all still in shock and grief and confusion.

I don’t have any grand conclusion, except that the story you’ve been told about that day is probably bullshit. None of us ever called the day "9/11", it was always "that Tuesday" or "the attacks" or other things specific to the experience. Afterward, I spent months and even years talking to friends who couldn’t get their heads to forget the sound it made when human bodies hit the ground near them from 90 stories up. I remember coworkers who had to report from the site of the attacks every day for weeks, and they came back looking ghostly from both the dust that still settled on their clothes, but also the haunted look in their eyes from facing such unimaginable horror. I still think of that burning pile whenever I smell an electrical fire.

As I write this, I can look out our window and I see the towers of light and I know that the majority of people who are looking at them probably feel little, if anything, about what they represent. I’m not mad or resentful that these things have faded; time passes, and we’re fortunate that grief fades with it. But my life changed that day, instantly and forever. I saw the best of what people could be, rising out of the worst that people can do. I promised myself I wouldn’t forget that lesson, and that I’d try to live up to having gotten to live through such an experience with such privilege. I still do think about the promise, even if it’s not every day any more.

If you’ve ever been told a story about 9/11, ask that person how it smelled. Ask them the greatest kindness that they saw. Ask them how they changed.

In Previous Years

Last year, "It's unrecognizable":

[M]aybe I keep coming back because I am hoping that others might still recognize the little glimpses of humanity that I saw on the day of the attacks, and that I saw in abundance, in New York City, in the days that follow. It wasn't a myth, it wasn't just wishful thinking, there really was kindness and care in this place that I love so much. I don't think those who tell the loudest stories today would even recognize it.

Two years ago, "There Is Nothing To Remember"

So it's clear that the events of that day have fully passed into myth, useful only as rhetoric in a culture war, or as justifications for violence. Nothing epitomizes this more than the fact that, while the memory has faded in culture broadly, it's only brought to the fore in situations like those where most New Yorkers would be targeted.

Three years ago, "Twenty is a Myth":

I can't change how society overall sees this event. To my eternal regret, I couldn't change how we responded in any meaningful way. But I did get to make personal changes, permanently and for the better, and the loss and grief of that day does still motivate me to try to honor the moment by pushing for justice, and care, and an earnest engagement with the world.

Four years ago, Nineteen is When They Forgot

I do have the experience of having seen this city bounce back from unimaginable pain before. I have seen us respond to attacks on our public life by rebuilding and reimagining public space. I have seen us grieve our losses and rally behind those who cared for those injured, and preserve space in our cultural memory for their pain and sacrifice. By no means have we done enough for all those lost, but it is absolutely true that we can rebuild. We’ve done it before.

Five years ago, Eighteen is History

There are ritualized remembrances, largely led by those who weren't  there, those who mostly hate the values that New York City embodies. The  sharpest memories are of the goals of those who masterminded the  attacks. It's easy enough to remember what they wanted, since they  accomplished all their objectives and we live in the world they sought  to create. The empire has been permanently diminished. Never Forget.

In 2018, Seventeen is (Almost) Just Another Day

I spent so many years thinking “I can’t go there” that it caught me completely off guard to realize that going there is now routine. Maybe the most charitable way to look at it is resiliency, or that I’m seeing things through the eyes of my child who’s never known any reality but the present one. I'd spent a lot of time wishing that we hadn't been so overwhelmed with response to that day, so much that I hadn''t considered what it would be like when the day passed for so many people with barely a notice at all.

In 2017, Sixteen is Letting Go Again

So, like ten years ago, I’m letting go. Trying not to project my feelings onto this anniversary, just quietly remembering that morning and how it felt. My son asked me a couple of months ago, “I heard there was another World Trade Center before this one?” and I had to find a version of the story that I could share with him. In this telling, losing those towers was unimaginably sad and showed that there are incredibly hurtful people in the world, but there are still so many good people, and they can make wonderful things together.

In 2016 Fifteen is the Past:

I don’t dismiss or deny that so much has gone so wrong in the response and the reaction that our culture has had since the attacks, but I will not forget or diminish the pure openheartedness I witnessed that day. And I will not let the cynicism or paranoia of others draw me in to join them.

What I’ve realized, simply, is that 9/11 is in the past now.

In 2015, Fourteen is Remembering:

For the first time, I clearly felt like I had put the attacks firmly in the past. They have loosened their grip on me. I don’t avoid going downtown, or take circuitous routes to avoid seeing where the towers once stood. I can even imagine deliberately visiting the area to see the new train station.

In 2014, Thirteen is Understanding:

There’s no part of that day that one should ever have to explain to a child, but I realized for the first time this year that, when the time comes, I’ll be ready. Enough time has passed that I could recite the facts, without simply dissolving into a puddle of my own unresolved questions. I look back at past years, at my own observances of this anniversary, and see how I veered from crushingly sad to fiercely angry to tentatively optimistic, and in each of those moments I was living in one part of what I felt. Maybe I’m ready to see this thing in a bigger picture, or at least from a perspective outside of just myself.

From 2013, Twelve is Trying:

I thought in 2001 that some beautiful things could come out of that worst of days, and sure enough, that optimism has often been rewarded. There are boundless examples of kindness and generosity in the worst of circumstances that justify the hope I had for people’s basic decency back then, even if initially my hope was based only on faith and not fact.

But there is also fatigue. The inevitable fading of outrage and emotional devastation into an overworked rhetorical reference point leaves me exhausted. The decay of a brief, profound moment of unity and reflection into a cheap device to be used to prop up arguments about the ordinary, the everyday and the mundane makes me weary. I’m tired from the effort to protect the fragile memory of something horrific and hopeful that taught me about people at their very best and at their very, very worst.

In 2012, Eleven is What We Make:

These are the gifts our children, or all children, give us every day in a million different ways. But they’re also the gifts we give ourselves when we make something meaningful and beautiful. The new World Trade Center buildings are beautiful, in a way that the old ones never were, and in a way that’ll make our fretting over their exorbitant cost seem short-sighted in the decades to come. More importantly, they exist. We made them, together. We raised them in the past eleven years just as surely as we’ve raised our children, with squabbles and mistakes and false starts and slow, inexorable progress toward something beautiful.

In 2011 for the 10th anniversary, Ten is Love and Everything After:

I don’t have any profound insights or political commentary to offer that others haven’t already articulated first and better. All that I have is my experience of knowing what it mean to be in New York City then. And from that experience, the biggest lesson I have taken is that I have the obligation to be a kinder man, a more thoughtful man, and someone who lives with as much passion and sincerity as possible. Those are the lessons that I’ll tell my son some day in the distant future, and they’re the ones I want to remember now.

In 2010, Nine is New New York:

[T]his is, in many ways, a golden era in the entire history of New York City. Over the four hundred years it’s taken for this city to evolve into its current form, there’s never been a better time to walk down the street. Crime is low, without us having sacrificed our personality or passion to get there. We’ve invested in making our sidewalks more walkable, our streets more accommodating of the bikes and buses and taxis that convey us around our town. There’s never been a more vibrant scene in the arts, music or fashion here. And in less than half a decade, the public park where I got married went from a place where I often felt uncomfortable at noontime to one that I wanted to bring together my closest friends and family on the best day of my life. We still struggle with radical inequality, but more people interact with people from broadly different social classes and cultures every day in New York than any other place in America, and possibly than in any other city in the world.

And all of this happened, by choice, in the years since the attacks.

In 2009, Eight Is Starting Over:

[T]his year, I am much more at peace. It may be that, finally, we’ve been called on by our leadership to mark this day by being of service to our communities, our country, and our fellow humans. I’ve been trying of late to do exactly that. And I’ve had a bit of a realization about how my own life was changed by that day.

Speaking to my mother last week, I offhandedly mentioned how almost all of my friends and acquaintances, my entire career and my accomplishments, my ambitions and hopes have all been born since September 11, 2001. If you’ll pardon the geeky reference, it’s as if my life was rebooted that day and in the short period afterwards. While I have a handful of lifelong friends with whom I’ve stayed in touch, most of the people I’m closest to are those who were with me on the day of the attacks or shortly thereafter, and the goals I have for myself are those which I formed in the next days and weeks. i don’t think it’s coincidence that I was introduced to my wife while the wreckage at the site of the towers was still smoldering, or that I resolved to have my life’s work amount to something meaningful while my beloved city was still papered with signs mourning the missing.

In 2008, Seven Is Angry:

Finally getting angry myself, I realize that nobody has more right to claim authority over the legacy of the attacks than the people of New York. And yet, I don’t see survivors of the attacks downtown claiming the exclusive right to represent the noble ambition of Never Forgetting. I’m not saying that people never mention the attacks here in New York, but there’s a genuine awareness that, if you use the attacks as justification for your position, the person you’re addressing may well have lost more than you that day. As I write this, I know that parked out front is the car of a woman who works in my neighborhood. Her car has a simple but striking memorial on it, listing her mother’s name, date of birth, and the date 9/11/2001.

In 2007, Six Is Letting Go:

On the afternoon of September 11th, 2001, and especially on September 12th, I wasn’t only sad. I was also hopeful. I wanted to believe that we wouldn’t just Never Forget that we would also Always Remember. People were already insisting that we’d put aside our differences and come together, and maybe the part that I’m most bittersweet and wistful about was that I really believed it. I’d turned 26 years old just a few days before the attacks, and I realize in retrospect that maybe that moment, as I eased from my mid-twenties to my late twenties, was the last time I’d be unabashedly optimistic about something, even amidst all the sorrow.

In 2006, After Five Years, Failure:

[O]ne of the strongest feelings I came away with on the day of the attacks was a feeling of some kind of hope. Being in New York that day really showed me the best that people can be. As much as it’s become cliché now, there’s simply no other way to describe a display that profound. It was truly a case of people showing their very best nature.

We seem to have let the hope of that day go, though.

In 2005, Four Years:

I saw people who hated New York City, or at least didn’t care very much about it, trying to act as if they were extremely invested in recovering from the attacks, or opining about the causes or effects of the attacks. And to me, my memory of the attacks and, especially, the days afterward had nothing to do with the geopolitics of the situation. They were about a real human tragedy, and about the people who were there and affected, and about everything but placing blame and pointing fingers. It felt thoughtless for everyone to offer their response in a framework that didn’t honor the people who were actually going through the event.

In 2004, Thinking Of You:

I don’t know if it’s distance, or just the passing of time, but I notice how muted the sorrow is. There’s a passivity, a lack of passion to the observances. I knew it would come, in the same way that a friend told me quite presciently that day back in 2001 that “this is all going to be political debates someday” and, well, someday’s already here.

In 2003, Two Years:

I spent a lot of time, too much time, resenting people who were visiting our city, and especially the site of the attacks, these past two years. I’ve been so protective, I didn’t want them to come and get their picture taken like it was Cinderella’s Castle or something. I’m trying really hard not to be so angry about that these days. I found that being angry kept me from doing the productive and important things that really mattered, and kept me from living a life that I know I’m lucky to have.

In 2002, I wrote On Being An American:

[I]n those first weeks, I thought a lot about what it is to be American. That a lot of people outside of New York City might not even recognize their own country if they came to visit. The America that was attacked a year ago was an America where people are as likely to have been born outside the borders of the U.S. as not. Where most of the residents speak another language in addition to English. Where the soundtrack is, yes, jazz and blues and rock and roll, but also hip hop and salsa and merengue. New York has always been where the first fine threads of new cultures work their way into the fabric of America, and the city the bore the brunt of those attacks last September reflected that ideal to its fullest.

In 2001, Thank You:

I am physically fine, as are all my family members and immediate friends. I’ve been watching the footage all morning, I can’t believe I watched the World Trade Center collapse…

I’ve been sitting here this whole morning, choking back tears… this is just too much, too big. I can see the smoke and ash from the street here. I have friends of friends who work there, I was just there myself the day before yesterday. I can’t process this all. I don’t want to.

The basic pitch is especially amusing these days because Anna was trying to get everyone excited about... a big, vague AI startup with no proven business model or use cases. Maybe she was just ahead of her time!

A lot of people have told me they were curious about what, exactly, Anna's pitch looked like, so I thought I'd share what I saw.

First, on February 22, 2016, there was this original email, under the subject line, "Artificial Intelligence X Art project":

Hello Anil,

My team and I are working on a new project that will explore Al creativity in art context by enabling direct collaboration between artist and Al, which will produce data that could be applied to problem solving on a higher level. I am a 25 year old art collector based in New York, and together with professors from the largest Al research institute in the world DFKI we are developing soft- and hardware that will be assigned to selected high-profile contemporary artists and will create a show exhibiting the results. See more details in dropbox links below.

The project is a part of a bigger initiative and is planned to launch simultaneously with the opening of my new art foundation designed by Calatrava and located in Aby Rosen's building in Gramercy NYC. In the future we are looking to experiment further and integrate Artificial Intelligence in different areas involving art and creativity.

We are currently raising our first $1mm round of financing.

Let me know your thoughts.

Best,

Anna Delvey

First of all, how quaint is it that an AI startup would be raising only one million dollars in funding? Also, I love the signifiers of mentioning the designer of her art foundation — who can argue with the taste of a art collector who likes Calatrava? I'm assuming at least part of the reason she reached out to me at the time was that I had been orbiting around the code-and-art scene in NYC for a while at that point, and was probably one of the few folks who was visible both with the museum crowd and as a VC-backed startup founder.

But really, I don't know exactly how she found me. Staying true to my character, I never replied to the email. So, she had a follow-up pitch a few weeks later, on March 27, 2016:

Hello Anil,

My team and I are working on the first Al-powered creative assistant in the world, and its reverse reaction-predicting counterpart. We are based in NYC, and together with professors from the largest Al research institute in the world DFKI and MIT in Boston we are developing soft- and hardware that will facilitate creative collaboration between an individual and Al.

Our deck: https://www.dropbox.com/s/w8ldihpt1wxkkz3/DECK%20COAl.pdf?dI=0

We are currently in the middle of assembling a board of advisors and raising our seed round.

Let me know your thoughts.

Anna Delvey

This message is the source of the original PDF of her pitch deck that you can use to follow along with her story. (Side note: she signed her emails below her name with her initials, which are the same as mine, and it still throws me off because it felt like I had somehow sent these messages to myself.)

One of the more striking and remarkable things about Delvey's pitch deck is how simple and text-heavy it is. Many other similar pitches I've seen are very graphics-rich, with lots of (usually contrived) charts and graphs showing industry trends or the like. By contrast, there's a self-assured tone to the stark, simple text of this deck, and of course the fact that she's only asking for roughly a million dollars seems quaint at a time when AI startups are raising a billion dollars solely on the basis of an idea.

I have to assume that at least some of the names she drops in the deck are also folks whose reputations were being used unwittingly or nonconsensually, but I do admire that she felt some of us would be persuaded to back her because she got a great architect to design her workspace..

In all, a lot of brilliant grifter energy was dedicated to this effort, and it's most telling how this pitch would be completely unremarkable today, except that it was presented by a young woman instead of a young dude. Honestly, if she's able to parlay that background into getting to dance on a game show, at this point we should probably just accept this as her next act.

A generation ago, those of us in tech might talk to our friends or family and hear them say, "I think the ads in my Hotmail account are terrible, and I can’t send any attachments. And Yahoo search is getting worse, plus Mapquest is so slow. Plus, I need to get all my friends off of AOL, and I don’t even know what anyone is doing on Friendster anymore. And I can’t deal with all the popup ads on Internet Explorer.."

Today, though, it’s Google search that’s rapidly getting worse, and Twitter that your friends are trying to quit. Cory Doctorow hadn’t coined "enshittification" yet in 2004, but he was certainly there warning us about it, and, well… some things never change.

Iterestingly, most of the people who’ve heard me say this over the last year or so think that I’m complaining or lamenting the situation, but I’m actually excited about it. That malaise by the big players in tech a generation ago yielded an exciting and inspiring new wave of innovations. While much of the money in big tech was chasing distractions back in 2004, many communities of small, independent creators on the open web were making the new pillars of web culture — many of which are still standing to this day.

When I wrote The Web We Lost, it was largely this flourishing of independent creativity and open collaboration that was I was largely lamenting. But I was wrong to think it was lost. It was merely dormant, beaten into near-irrelevance by the domination of the giant tech players. At the start of this year, I wrote The Internet Is About To Get Weird Again, which began by calling back to the Internet of 2000. In thinking more about it, though, we more closely resemble the Internet of a few years later, where the crash of the dot-com bubble and the stock market had the same effect that the popping of the crypto bubble did: the casuals who were just trying to make a quick buck are much less likely to jump in the pool. There’s far more space for weirdness and passion and actually making new shit.

Twenty years ago, we saw the first large-scale social networks — and there were lots of them, not just one. We saw a passionate community rise up and challenge the most powerful tech monopoly that had ever existed, and create a viable mainstream consumer option for the fundamental tool everyone uses to access the internet. The platforms for publishing and sharing online were democratized, and the radical, open architecture of formats like podcasts were codified.

So it’s no surprise to me that the renaissance of the open, human internet is in full swing. And this time, we have the advantage of knowing how the bad guys might try to take advantage of it, so we might not be doomed to repeat the most painful parts of the cycle that followed.

I know you think you have control over your subscribers on Substack. But understand this: every single new feature Substack releases, from their social sharing to their mobile apps, is proprietary and locks you into their network. They don't let your writing live on your own website or domain under your control unless you pay them for the privilege. And it'd be a shame if something happened to those subscription dollars you're counting on, wouldn't it? Even when you say "but my readership is growing!" know that most new subscribers come from other writers referring their readers to you. Somehow... Substack wants credit for those writers making that choice? Even though it was your writing that inspired it? That's not some magical network effect thanks to Substack! That's just the internet, working as it was supposed to.

Links are powerful — that's why Instagram and Twitter and Threads punish and limit them, and why Substack tries to take credit for them. And that's why "wherever you get your podcasts" is such a radical concept — like email, it's a medium that the tech tycoons don't, and can't, own. People can read your writing "wherever they get their email".

We constrain our imaginations when we subordinate our creations to names owned by fascist tycoons. Imagine the author of a book telling people to "read my Amazon". A great director trying to promote their film by saying "click on my Max". That's how much they've pickled your brain when you refer to your own work and your own voice within the context of their walled garden. There is no such thing as "my Substack", there is only your writing, and a forever fight against the world of pure enshittification.

@decoderpod Our host Nilay asked Substack CEO Chris Best the tough questions about whether racist speech should be allowed in their new consumer product, Substack Notes. #techtok #technews #substack #ceo ♬ original sound - Decoder with Nilay Patel

Substack is, just as a reminder, a political project made by extremists with a goal of normalizing a radical, hateful agenda by co-opting well-intentioned creators' work in service of cross-promoting attacks on the vulnerable. You don't have to take my word for it; Substack's CEO explicitly said they won't ban someone who is explicitly spouting hate, and when confronted with the rampant white supremacist propaganda that they are profiting from on their site, they took down... four of the Nazis. Four. There are countless more now, and they want to use your email newsletter to cross-promote that content and legitimize it. Nobody can ban the hateful content site if your nice little newsletter is on there, too, and your musings for your subscribers are all the cover they need.

The counter-argument people generally have is convenience (which I was more empathetic towards before great options like Ghost and Beehiiv and Medium even WordPress stepped up their game) and the theoretical benefits of network effect from being on Substack. Which is largely a myth (most referrals are thanks to other writers, not the platform) and means you have to be open to the platform using your writing to introduce people to the most insidious anti-trans and white supremacist rhetoric on the internet.

That's why they have encouraged you to call it "my Substack". It's not your goddamn Substack. When Marc Andreessen and his friends funded Clubhouse (remember that garbage?) so they could hang out in audio chats that were explicitly about destroying accountability media, they also took time out to fund Substack specifically so they could undermine major newspapers that they thought would criticize their interests. And it worked, obviously.

Here's how you can export your subscribers. Here are great alternatives. Before you start those processes, one change you can make today: you can talk about your work as your work. It's your newsletter, or your email, or your blog. Or just your writing. But it sure as hell isn't "your Substack".

Here, then, are a few key lessons that may have additional resonance in areas of your life outside of fire-making as well.

The most important ingredient is invisible

It’s very obvious that you need fuel and a spark to start a fire. But the most important enabling aspect is oxygen, and it’s the part you can’t see. So many struggling fires are lacking only oxygen to enable them to become a true conflagration, but people often fall back to reshuffling the things they can see, rather than considering the vital parts that are invisible to them.

It doesn’t take much if everything is at temperature

Again, much preparation involves moving around the components of fire-making, but all of those considerations are far more forgiving if you have fuel that is already near combustion temperature. A 400-degree log is ready to burn even if everything else is only marginal; a freezing-cold log will be recalcitrant even if you’ve arranged everything else perfectly. This is where legacy can be a big factor: it’s a lot easier to start a fire on top of a bed of already-hot coals.

Where there’s smoke, there’s fire

Sure, you’ve heard this one before. But have you really thought about why it’s true? What the smoke is telling you is where the air is flowing. And where the air is flowing, the heat is going. The necessary oxygen and heat are following a path, and making the invisible workings of the fire visible to you. It’s a hint about what the fire wants to do next, if you listen to it.

You’re designing an airflow system with fuel attached

This is a conceptual shift from how most people think of fires. Unless you’re only burning a single log, you’re going to be replenishing the source of fuel over the lifespan of the fire. So any individual structure or support won’t persist. But what will stay constant in a well-made fire is the flow of air and heat that make it possible, with additional fuel being added as needed. So, build that flow and then make everything else subordinate to the ongoing combustion.

Each log is a year

Depending on the species, and the dimensions, each log in your fire might represent the equivalent of a full years' growth for that tree. All of its effort to capture the energy of the sun, for the entirety of an orbit around that star, reduced to the fuel in your hand, and gone before your eyes. Maybe that's something to observe, and to practice being grateful for.

Nothing will last

If you’ve done everything perfectly, including setting up a safe space to burn that’s far from any unexpected fuel sources, then the natural course of events is that, left to its own devices, your fire will eventually burn out. It is up to you whether you consider that eventuality a failure or a success.

I hope you stay warm and safe.