Never has this quote been more true, nor more dystopian.

I’ve been hesitant to write what I’ve experienced over the past 45 days because it continues to evolve so quickly I fear anything I share will instantly become obsolete. But a post has gone viral on Twitter, spawning endless discussion, dissection, and even mockery. Yes, something big is happening. Let me be less bombastic, more direct, and help put this moment in context.

I’ve been writing and shipping software since 1997. Back then, you spent years programming something, and when you were done you had to burn physical CDs and mail them to your customers. When I joined Apple in 2006, they shipped software once per year.

I wrote code through the dot-com boom, through Web 2.0, through the mobile revolution, and through the cloud transition; none of those platform changes were as transformative as what I’ve seen over the past few months.

AI is compressing timelines and changing the nature of work in ways that break our intuitions.

Many point to November 20, 2022 - ChatGPT’s debut - as the dawn of the AI era. That’s fair; much of the world had previously never heard of AI nor understood its potential capabilities. It was the first time you could ask a computer to do something, in plain English, and it would do it. For many it replaced Google as their point of research, it gave them someone to talk to, it became a friend.

I’ve always focused more on productivity. The singular theme running through the 3 companies I’ve built is time-savings. I crave tools that let me do more, faster, and I love building those tools for others.

In that lens, it’s actually November 24, 2025 - Opus 4.5’s debut - that changed the world.

By mid-December, it was clear that this model was actually quite good. Disturbingly good. It wrote exceptional code, with relatively little guidance, and stayed productive even in very large, very complex codebases. That was a first.

By the holidays, I realized that software engineering, as the day-to-day work I had known it, had changed forever. The first week of January, we completely restructured our Digits code repositories for AI agent productivity. Today, just 6 weeks later, much of the code we ship is AI-written and human-reviewed. By this summer, I expect that 95% of software engineering - a field I have dedicated my entire life to - will be automated.

For me, it already is. I spent a few hours last night coding (as I have most evenings of my life since 6th grade), except now it’s different. I haven’t actually written code since December. Now I just write English. Actually, I don’t type anything at all, I just dictate English using Wispr, and Claude writes the code for me. I can now ship more software every day than I ever have in my life, but the thing I spent my entire life being good at? That’s now gone.

Software engineering is just the leading edge.

Another field I have come to know quite intimately - accounting - is also facing its watershed moment. The month-end financial close, the thing that every serious business pays accountants to do, will effectively be automated this year. The latest machine learning models make computers dramatically more accurate, and thousands of times faster, than any human bookkeeper. Even complex accounting (accrual schedules, revenue recognition, and painstaking review processes) will fall to AI before end of year.

To address the obvious, there will still be software engineers, and there will still be accountants. I see no signs of taste and judgment being replaced or delegated, nor will your AI agent accept liability or offer indemnity. But the day-to-day work of these professions has changed forever. We are all on this journey together.

How are these impacts experienced today? Completely unevenly. Most programmers will still spend every day of 2026 programming, just like they always have. Most accountants will spend every day this year doing the accounting. Except in pockets, where it’s the dawn of a whole new era, where agents do most of the work.

The future is here, and one day soon everyone will realize it. Slowly, and then all at once.

To be sure, working remotely is not for every business, and not for every individual.

Little did I know how soon so many businesses and individuals would be forced to make do, and how quickly fully-remote work would become mainstream.

It’s been an abrupt transition… and for many, it hasn’t been easy.

Over the course of the year, I’ve heard from countless startup founders, small business owners, and team leads looking for more advice on how to build effective, collaborative, productive, and happy fully-distributed teams. The last, of course, being the most challenging.

For those of you that have held-off implementing major process and collaboration changes to optimize for remote work, the time to reconsider is now.

While there may soon be light at the end of this tunnel — thanks to the incredible vaccine development efforts by scientists and researchers worldwide — I foresee no quick reversion to “normal”. Remote work is here to stay, and every industry that can do so will embrace it.

Success in 2021 and beyond will be defined by those who adapt to remote work most effectively.

Here’s what we’ve learned at Digits.

If you’d rather listen than read, Stanford University has published a full interview covering our approach to remote work, as well as a short 7-minute summary as part of their free Entrepreneurial Thought Leaders podcast.

What We’ve Learned, Remotely

Digits went fully-remote the day we started the company in 2018, with my co-founder Wayne in Los Angeles and I in San Francisco. We knew it would be a fools-errand to try to build the company we envisioned in just one city (there’s simply too much great talent everywhere) and we both shared distinct, negative prior experiences managing multiple remote offices: the “second-class citizen” effect felt by those not frequently present at HQ is hard to overcome.

So (and despite distinct skepticism from a few of our investors — don’t worry, we appreciated the push-back!), Wayne and I made the decision to embrace remote work wholesale: Digits would never own a physical, shared office, and we would design our approaches and processes from the ground-up to champion distributed work.

After seeing so many different attempts at remote work by so many companies over the course of this year, and after reflecting on the most effective aspects of our own culture at Digits, it’s become more clear to us than ever what’s really important.

There are now thousands of online articles pitching countless techniques for improving the remote work lifestyle — it’s overwhelming.

As founders, here are the practices we believe have had the most positive impact at Digits, and the ones that we would recommend you try out with your teams today, even if you’ve previously preferred an in-person work experience.

Embrace Synchronicity

For many, remote work is black and white: you’re either in the office together, or you aren’t. But degrees matter. Time zones matter.

In our experience, productivity and happiness go hand-in-hand with collaborating live, so we’ve made a conscious decision at Digits to agree to all work roughly the same hours: in our case, US Central Time. Folks out West tend to fire up their computers a bit earlier than they otherwise would, and those back East tend to stay on a bit later, or check back in after dinner, or once their kids are asleep. There is still a bit of skew on each side, but to have our entire team online together, every day, simultaneously, for the core hours of US Central Time is magical.

Sure, there are downsides. There are incredible folks (and former colleagues from prior companies!) in EMEA and APAC that we would adore the opportunity to work with, but we have assembled an incredible team that can collaborate live across North, Central, and South America synchronously. The pros outweigh the cons dramatically, and we communicate this upfront in our recruiting materials: when you join Digits, you’re free to move wherever you want within continental American timezones.

For those of you who already have colleagues spread around the globe, our advice would be to strive for team synchronicity. Here’s how.

The Buddy System: Scaling Synchronicity by Shrinking Teams

The traditional “two-pizza” team of 8–10 folks gathered around a conference table may work well in person, but we’ve come to realize it’s unwieldy on Zoom.

Even on fast Internet connections, latency often makes it awkward to get a word in edgewise in group settings, and inevitable background noise from pets, children, construction, or everyday city life motivates a default-to-mute culture, which adds another layer of friction to highly-participatory group dialogue.

That’s ok — we’ve never found large group meetings to be productive to begin with 😉

At Digits, we consciously break teams down into their smallest possible units: every project is tackled by tiny teams of 2–4 people, and in practice we found that 4-person teams often self-divide pairwise to get work done more effectively. We call this the Buddy System.

Working on something by yourself is lonely.

Working on it by yourself, in your home, with nobody else around, is just sad.

Working on it with a buddy is awesome.

In practice, substantially everything we do at Digits is tackled collaboratively by 2–3 people. They work together, synchronously, throughout the day, and decide when they want to pair on Zoom, Tuple, or Slack Audio, and when they want to go heads-down and sync back up in an hour or two. But they always know who they can count on to brainstorm with, or get feedback from, or have review their work, and they know they won’t have to wait around for it because that person isn’t elsewhere working on something else.

Yes, this means we take on fewer projects simultaneously than we otherwise might, but in exchange, each work-stream gets completed far faster, at a far higher quality level, and the work day is far more enjoyable.

We default to coordinating work between teams asynchronously: via shared Google Docs and Trello, in order to minimize meetings and maximize flow. Input is welcomed, and actively sought from broad groups across the company, but that doesn’t take a meeting to accomplish. Let people chime in on a doc when they have time, and then grab time with them and their buddy directly if it deserves a live conversation. After all, they’re unlikely to be in another meeting…

The Maker Schedule, Writ Large

One of the most challenging aspects of almost any large organization is the meetings. An endless parade of prescheduled time-blocks, which require abrupt context switching and leave little time for thought, creativity, or even a snack. How easy it is to end the day exhausted, yet with the gnawing feeling that you didn’t actually accomplish anything of note?

For those with the maker mindset — with roles that require creativity and execution — this sparks terror. There is no better way to ruin the productivity of your design and engineering teams than a few poorly placed meetings. Losing half a day or more due to a couple preset commitments is not an exaggeration. At large companies, it’s a way of life.

At Digits, we discovered something we hadn’t realized: scarce resources are largely to blame.

Conference rooms are evil.

At a traditional company (all of Silicon Valley included), I need a place to hold a meeting. It would be rude to stand around and make noise somewhere public, where others are trying to work, so I book a conference room. Genius.

Except, conference rooms are in high demand, so I must reserve one in advance, and my meeting must conform to the room’s list of available slots. Without thinking about it, my meeting must now be 30 minutes or an hour long, and the time it will happen is now fixed on the calendar and broadcast in advance.

This is a nightmare.

It turns out that the maker schedule is not all that disrupted by the meeting itself… but rather by the presage of said meeting.

There is nothing more distracting than seeing a hard-stop on your calendar in 90 minutes. Do I have enough time to build out this feature before then? Can I really sink my teeth into this design problem in less than two hours? Should I just spend this time replying to email, or triaging bug reports, or grabbing coffee?

“Don’t worry,” I tell myself, “I’ll dive into my real work after that meeting.”

Oh no. I also have a 2pm!?

At Digits, we have full-company, all-hands meetings 3 times a week, spaced every 48 hours:

• Monday morning Kick-off (30 mins)
• Wednesday morning Check-ins (30 minutes)
• Friday afternoon Show & Tell (75 minutes)

They are scheduled to fall at the beginning or end of the day, to minimize disruption.

More importantly, we aim to schedule no other internal meetings.

Sure, interviews need to be booked, and customer and partnership calls need to happen, but it’s easy to distribute interviews across the team (and monitor how frequently any given engineer is pulled into an interview) and external-facing roles tend to be less maker-schedule driven.

This does not mean people don’t talk! Instead, we highly prioritize an ad hoc, interrupt-driven culture. Remember, the meeting itself is far less painful than the upcoming hard-stop on the calendar. And with no conference rooms to book, there’s no need to schedule anything in advance, so we don’t bother.

Much to our initial surprise, this has lead to a bit of a utopia: our typical “meeting” is 5–7 minutes long, includes less than 6 people, and happens with just a couple minutes of notice. Everyone is typically available because they’re all working US Central Time, and they aren’t tied up with any other pre-scheduled commitments, so why not join? And in just 7 minutes, they’re right back to being productive, because the meeting wasn’t long enough to “page out” or forget what they were doing and shift them out of flow.

This sounds too good to be true. It isn’t. It’s reality.

Remote Work At Digits

Taken together, our days and weeks at Digits look like the following:

1. High-bandwidth all-hands, every other day, so we all know what everyone else is working on and how it’s all progressing. The complete, cross-functional visibility these provide builds confidence that the whole company is rowing in the same direction, and immediately surfaces any duplicate or conflicting efforts.
2. Empty calendars, devoid of pre-scheduled internal meetings, so everyone can stay in flow and focus on getting work done.
3. Tight-knit, synchronous collaboration with a buddy, day-in and day-out, so you’re never alone during the day, and you always have someone you count on to brainstorm with and get feedback from.
4. Asynchronous, cross-team collaboration via shared Google Docs and Trello cards. Input and feedback is actively sought, but never blocked on, and each team is empowered to deliver their work end-to-end.
5. Ad hoc check-ins throughout the day, as needed. With no notice or preparation that takes you out of flow, it’s trivial to pause for 5 minutes and share an update, or get input from another team and then go right back to being productive with your buddy.

Spreading the Word

A few months ago, it was an honor to be invited by Stanford to share Digits’ approach to remote work as part of the university’s Entrepreneurial Thought Leaders lecture series, and they have published the full talk here.

With 2020 coming to a close, Stanford eCorner just recently published a recap of their key entrepreneurial takeaways from this year, and I was floored to be featured again. Thank you Tina :)

Join us at Digits

We’ve been heads-down for the past two years, building out our full vision for Digits, and we can’t wait to share it with the world in 2021.

If you’re excited to join a passionate, fun-loving, fully-remote team that’s obsessed with building delightful business finance software, we’d love to get to know you!

The film masterfully intermixes drama with sit-down interviews with myself and a dozen other former social media execs, in hopes of communicating the (often subconscious) consequences of the world’s growing dependence on social media for news and entertainment.

It’s fantastic that this message is beginning to resonate broadly.

For those within the tech industry, of course, questions abound. In just the past few days, I’ve been contacted by product managers, engineers, designers, and other tech execs in Silicon Valley and beyond, curious to better understand what exactly is at play here, and what if anything they can do about it.

There is also some confusion about how the film came about, who was involved, and how it relates to other hot topics in tech over the past decade.

To make the film as widely-accessible as possible, the Exposure Labs team obviously kept everything relatively high-level. If you’re interested in diving beneath the surface, and understanding the product mechanics and the human psychology at play, here is my own take on what is happening under the covers.

First, some key points to level-set on:

1. This post is blame-free and not targeted at anyone. These challenges are structural, not the result of any one person, team, or company. These companies are full of amazing, smart, passionate, ethical folks, and everyone I ever interacted with (I was there!) wanted deeply to do what was best for people around the world.
2. Where we are today is not due to anyone’s lack of execution. In fact, it was excellent execution that brought us here: the algorithms that power today’s platforms succeeded beyond imagination, and engineering-product-design teams iterated rapidly to successfully achieve company goals. People were promoted and widely recognized because of this work, it was not hidden in the shadows, and there is nothing confidential about these topics.
3. Today, these issues are a lot less controversial than they were when I was interviewed for the film in early 2018, and I heard from the production team that it was very challenging to convince anyone at that time to go on the record about these topics. I get it—I was personally hesitant to be interviewed, though I’m now glad Jeff Orlowski persuaded me to do it.
4. I am sure there were many other people thinking about the same things and who would have made great additions to the film. I know the production team reached out to a LOT of people to try to convince them to join, with mixed success. I’m sure there are additional folks that they missed.
5. There is a lot of technical subtlety to these challenges that is hard to express in writing, much less in film. I also don’t pretend to know all of it, so I hope this post is the beginning of a productive conversation within the tech industry on how to move forward.
6. All that said, social media’s impact on the world today is real, and it is devastating. The status quo is unsustainable, and these companies need to treat this seriously and make material changes to their platforms, more rapidly than they are currently doing so.

Background Context

I was named Head of Consumer Product for Twitter in 2015, which meant leading the product teams, in close collaboration with design and engineering, that worked on Twitter for iOS, Android, and the Web—the core consumer experiences that come to mind when you think of “Twitter”.

I left the company on January 18, 2017 and I promised myself I would never again work in ads-based social media.

Almost a year earlier, on April 12, 2016, I had attended a small dinner in San Francisco organized by Tristan Harris, Google’s former Design Ethicist, who would go on to found the Center for Humane Technology. Over dinner with Dave Morin (Facebook’s former Head of Platform), Chris Messina (the inventor of the hashtag), and a small handful of others, Tristan laid out his early understanding of how social networks were stealing control of people’s time, without their knowledge, and what the negative impacts of that were.

The concept itself was not novel—how much time people spent on Facebook, Twitter, or Instagram was a frequent topic in popular culture—but the depth of his understanding of it, and his clairvoyance in recognizing the downstream consequences, were both enlightening and terrifying. I was struck by the dinner, and I stepped down from my role in product leadership just a couple months later (I spent the remainder of my time at Twitter aiding the corporate strategy teams).

To be clear, I have been obsessed with data privacy for a long time. When my co-founder Wayne Chang and I sold Crashlytics to Twitter, in January of 2013, we made sure that the data we brought with us (which already covered hundreds of millions of smartphones worldwide) was explicitly siloed off, and inaccessible to other business, product, or engineering efforts, including advertising. (This was highly atypical at the time, and in stark contrast to Facebook’s Onavo acquisition.) Wayne and I apply this same level of care for customer data to this day, at Digits.

A few months after I left Twitter, in the Spring of 2017, Jeff Orlowski reached out to me. He was the director/cinematographer behind the Emmy-winning climate change films Chasing Ice and Chasing Coral, which I had helped produce. (N.B. — I am not a producer on The Social Dilemma and have no stake in the project.) It turns out Jeff had also heard about Tristan’s work, and was curious to gut-check what he was learning.

The essence of the problem can be distilled as follows: the ads-based business models that power almost all social networks (both then, and now) implicitly motivate efforts to increase time spent per-user in the product, in order to make more revenue. And the techniques they were using to do so were getting ever-more advanced.

Were we just crazy?

As I discussed this further with Tristan and other friends in tech over the course of 2017, it struck me just how eye-opening and controversial this was, even to those who best understood the dynamics of how Internet-based social networks operated.

Could Facebook, YouTube, or Twitter really have played any role in Brexit or in the 2016 US Election? Zuckerberg had gone on the record to vehemently deny the possibility.

But reflecting on it with the full benefit of hindsight, the answer is yes. Unquestionably.

Today, it’s even more clear. If you ask yourself…

How has the world become so polarized and divisive?

How have lies come to outpace facts on a daily basis?

How have baseless conspiracy theories gained so much in popularity that they are impacting broad populations and mainstream political parties?

…and then rationally walk yourself through the underlying mechanics of the social media business, it all becomes so painfully obvious.

Simply put, these aspects of today’s global chaos are each a direct, rational result of trying to make money from ads.

Spoken technically: there are insidious, inescapable, structural issues with any consumer product that combines 1) advertising, with 2) user-generated content, and 3) machine learning.

But wait, isn’t this just Health & Safety?

It’s important to explicitly distinguish The Social Dilemma from the essential, long-recognized, and ongoing, health & safety efforts across all the major social platforms today.

Online abuse and harassment is an incredibly serious topic with real-world consequences, and countless individuals both inside and outside the tech industry have risked their careers and reputations over the past decade to drive awareness of these issues and demand changes.

Without at all diminishing those efforts, what is terrifying about The Social Dilemma is that it’s not actually about health and safety, but something more structural and insidious: the business model itself.

Imagine if everyone on the entire Internet was as friendly and as supportive of each other as the nicest Great British Baking Show contestant… wouldn’t that be amazing?

Unfortunately, the devastating consequences of online ads-based business models would still exist. The world today would still become increasingly polarized, and increasingly influenced by lies, just a bit more politely.

OK, what makes online advertising different?

Advertising, of course, isn’t new. Someone with money to spend and an agenda to promote can pay to get their message in front of an audience. It has been this way for hundreds and hundreds of years.

I choose the TV shows I watch, and the magazines and newspaper articles I read, but I don’t choose the ads that come with them. They are picked (for better or worse) by the outlet’s publishers and by the sponsors that they work with.

Historically, though, these have all been passive experiences. The content was produced, it was distributed, and it was consumed. And the content, just like the advertisements, was immutable: predetermined before the consumer arrived, and targeted — if at all — at a broad population demographic. Every consumer enjoyed or suffered the same experience.

Digital advertising started with this same framework in the ’90s, with banner ads littering the tops and sidebars of countless online publications. Far more annoying than print ads, to be sure — given their propensity for garish colors and crude GIF animations — but fundamentally identical nonetheless.

Then, everything changed.

What if ads could be selected for display in real-time? What if they could vary based on the person who would experience them? What if they could react to the specific intent of the consumer, in the moment?

Search advertising (invented by Overture, popularized by Google¹) did just this via keywords. Suddenly, ads were radically more relevant. Which, of course, made them radically more effective.

At that time, in the early 2000’s, this was largely accepted as an improvement: why would I want to see an ad that I had no interest in? Could ads finally be helpful?!

With the rise of social networks in the mid-2000s, this approach continued. Ads were selected based on the people I followed or the demographic and location information I revealed in my profile.

It seemed reasonable, but there was a critical difference.

With search advertising, the ads I see are a direct result of the actions I take. I consciously decide to search for something and then I see relevant ads as part of the results page. OK, perhaps that is fair. The more searches I do, the more ads I see.

But unlike with search, there’s another dimension that can be subconsciously exploited when you combine ads with other media content…

Time.

How often have you opened Facebook, YouTube, Twitter, etc., and suddenly 20 minutes pass in the blink of an eye?

This is not an accident. This has been engineered. Why?

Let’s imagine you are a rationally-behaving social network. Congratulations.

Like any business, you have a fiduciary duty to increase shareholder value: aka drive profits. Since you’re ads-based, you have two major levers at hand:

1. You can increase the relevance of each ad you show (so advertisers pay you more per ad, because people are more likely to tap on it).
2. Or, you can increase your total number of ad impressions (so advertisers pay you more in total, because their ads are shown more times).

Starting with #1, the strive for relevance is the core driver behind these networks’ obsession with data collection, and the resulting online privacy protection movement.

The more data you have about me, the more you know about my interests, my strengths, and most importantly my weaknesses. You know what to show me that will get me to watch something, tap something, or buy something — whatever the advertiser wants me to do.

Effectively, ads-based businesses are selling the opportunity to change their users’ behavior. Their users’ attention and actions are, quite literally, their product.

(This is again why Wayne and I outright refused to share Crashlytics data with Twitter—app developers should not be forced to “sell” their users just to benefit from the functionality of a 3rd-party SDK.)

This part of the story is its own nightmare, but it’s a nightmare that the tech and advertising industries generally understand and accept today, for better or worse, and I won’t cover it further.

The need to drive ad impressions is far more insidious.

Remember, you are now a rationally-behaving social network. When you turn your attention to ad impressions, you have 3 major ways to drive growth:

1. You can get more monetizable users (the total number of people you can show ads to).
2. You can increase ad load (how many ads are shown to people compared to pieces of normal, organic content).
3. You can increase usage (how often and for how long each user engages with your product, so you have the opportunity to show them more ads over the duration).

Monetizable user growth is typically achieved via virality tactics and social psychology. By promoting engagement with new people (“import your contact list!”), notifying them of actions they may be interested in (“you’ve been tagged in a photo!”), and orchestrating feedback loops (“Sally and 5 others liked your post!”), it is conceptually straightforward for social networks to spread through and across real-world communities (“We found 12 people you may know!”).

Ad load is also straightforward and easily tunable, but it can quickly pass a tipping point: most people have a strong distaste for seeing too many ads in too short of a timeframe. In fact, you may notice that towards the end of fiscal quarters, you often see more ads than usual on social networks — an easy way for them to juice the numbers for a few days to ensure revenue targets are hit, then dial it back before too many people get too annoyed.

Finally, increasing usage is similar to driving user-base growth. Some social interactions can be tuned to promote reactivating existing users rather than focusing on bringing new people in.

At least, that’s what everyone thought…

It turns out you can drive usage without relying on social interactions at all.

The Impact of “AI”

Over the course of 2013–14, Facebook famously switched its newsfeed to be algorithmic, where for the first time the content you saw was not purely the result of the people you friended and the order in which they posted things. There were now other factors at play.

Despite widespread threats to “delete Facebook” (surprise! most people didn’t), this made sense at first: did I really want to see every single post from that crazy high-school friend who now had too much time on their hands and spent every waking moment on the platform? (But de-friending them would be so awkward…)

After all, what is the difference between an ad and a piece of organic content? If Facebook could programmatically select the ads people were seeing, why couldn’t its machine-learning algorithms programmatically select the user-generated content people saw as well? In theory, that could result in a much better product experience than pure chronological order.

Their realization of this was profound.

But wait…

Organic content that is “better” in which way? “Better” for whom? How would the algorithm pick which content to show?

Facebook had a fiduciary obligation to drive ad impressions (which drove revenue), so of course that became a major factor in their algorithmic content selection criteria. And sadly, this change was so effective that every other social network had no choice but to mimic it in order to remain competitive.

It turns out that social media usage (time spent per user) is highly influenced not just by social interactions or by the ads you see, but also by the organic, user-generated content you see, and the order in which you see it.

For the first time in history, it was possible for a media platform to uniquely specify content, in order, on a person-by-person basis, that had the highest probability of incrementally keeping that person in the product, which meant that person scrolled down further, which meant they saw more ads.

Machine learning algorithms, at a high level, are very easy to understand: give the algorithms a goal state (e.g. drive ad revenue), and they will optimize for it ruthlessly.

Facebook’s horrific, deeply profitable discovery.

The final piece of the puzzle is, sadly, human nature.

We want to belong.

As humans, we tend to not like things we disagree with. We want to be part of a community of shared-interests. We want to be told that we’re right, that we’re not crazy, that there are lots of other people like us.

Otherwise, if we see something we disagree with, our fight-or-flight mentality kicks in. And we close the app.

We also have insatiable appetites for novelty and drama. We want to be shocked, enlightened, fascinated, enraged, or amused, but always in a way that directionally aligns with our existing beliefs.

Polarizing for Profit

In just a couple of years, by the time Brexit and the 2016 election were coming into focus, Facebook’s machine learning algorithms had made some critical “discoveries”:

• As a general rule, people are more likely to seek out and consume content that they already agree with.
• They’re more likely to engage with and share content that is outrageous in some way. (Yes, the algorithms rediscovered what clickbait is.)
• And, once enraged and engaged, people are more likely to keep scrolling for more content along those same lines.

This let Facebook show a lot more, and a lot better-targeted, ads than they were ever able to before. They achieved advertising’s holy grail: they were able to accurately target both content, and ads, to an audience of 1. At a global scale.

The net result is that, purely in the name of ad revenue, social networks are polarizing our world today at a rapid pace.

Every piece of content I see — for hours a day in many people’s cases — is specifically selected to keep me there. To keep me scrolling. To keep me tapping. To keep me seeing ads. Because it’s almost always something that I like, or find amusing, or find outrageous — and the algorithms already know that!

So the endgame is sadly clear: the major consumer tech platforms, not just in the US, but globally, now have an implicit fiduciary obligation to reinforce my current views, which only makes me (and everyone else) more dogmatic and more radical along my own lines, no matter which topic the content is about or which direction I lean.

I am being polarized and radicalized for their profit.

Real-world Impact

This isn’t just theory or hyperbole—this impacts literally billions of people every single day—and the real-world effects of this are dramatic:

1. The reality of global warming is undisputed by science and yet a large percentage of the planet has been convinced otherwise, blocking desperately needed regulation and policy changes.
2. The baseless Pizzagate conspiracy theory was “shared roughly 1.4 million times by more than a quarter of a million accounts in its first five weeks of life"² and resulted in an armed gunman storming a DC-area pizzeria.
3. The government of Myanmar systematically, over a period of years, leveraged Facebook to incite hatred towards the Rohingya minority group, to the point where genocide became socially acceptable amongst the majority.³
4. Governments and political groups in Mexico, Brazil, and 70 other countries have been caught intentionally spreading disinformation to their own citizens via social media.⁴
5. Well-known American politicians routinely spread outrageous, brazen lies, knowing that they will go viral amongst their fan bases and that few people will ever take the time to check their veracity. Studies have shown that lies spread 6 times faster than facts.⁵

Never before have media platforms been so incentivized to spread outrage and disinformation, but what can be done?

Taking a Stand

As with most tragedies of the commons, it’s difficult for any single person to make much difference. Even remaining at Twitter in a position of influence would be a fool’s errand — the problem is with the business model itself, not the execution thereof. Great execution towards business goals is what got Facebook here in the first place.

And this has become a trap: alternative business models, such as charging a subscription for access or charging by follower count/audience size, will almost certainly result in far less total revenue. The algorithms have extracted more dollars from advertisers, on a per-user basis, than the average user’s willingness (or sheer ability) to pay.

In a competitive capitalist market, there is no clear path for any individual to take a stand — any company they succeeded in swaying would immediately be overtaken by less-principled competitors and face certain shareholder revolt.

But by acting together, we can make a difference.

Like has happened in so many other industries, it has come to the point where we have no choice but to force these ads-based consumer tech platforms to internalize their negative externalities.

Controversial, no more.

There’s good news: this is no longer all that controversial amongst my friends in tech, and there are now many smart people working on these issues and how to tackle them (both inside and outside these companies).

In sharp contrast to my discussions in 2017, many of the engineers, product managers, and tech execs I’ve spoken with over the past year now fully understand and agree on the mechanics that are driving this. But they don’t yet know what to do about it—so, let’s have that discussion together. There may not yet be a silver bullet solution, but here are some questions to ponder:

1. Should there be limits on the amount and types of data about an individual that can be collected and stored in a consumer product?
2. Should there be limits on the maximum number of ads that can be shown to an individual, both in a given session and in a given time interval, whichever lasts longer? (We must restore everyone’s control over their own time.)
3. Should personalized advertising even be legal at all? (When driving down the highway, we all see the same billboards, and we can have a shared conversation about them. Yet nobody knows what anyone else sees online—how can you possibly empathize?)

It is past time that the tech industry talks about this topic openly and honestly, and commits to fixing it, because this is just the beginning. Machine learning algorithms are relentless in their pursuit of goal states, and this is not the last psychology trick they will discover — we need to be prepared for the next one.

As Tristan so eloquently puts it, we need not worry about the day when machines overcome human strength (when robots “take over the world”)…

We must worry about the day when machines overcome human weakness, when they can manipulate our behavior to achieve their own goals.

Thanks to the simple, rational pursuit of advertising revenue, that day has already passed.

Done right, transparency promotes open and collaborative work environments. It fosters team trust and communication. And it promotes cultures where intellectual honesty and data-driven decisions supersede politics and excuses.

All that said, I have experienced first-hand the repercussions of being overly transparent, and I have spoken with countless founders who aspire to be transparent with their teams, but still struggle with how much to share, at what point, and to whom.

When I recently wrote about the role of the founder, I focused on your responsibility to scale yourself and empower your team by bringing top-down context, rather than top-down decisions. When that context is potentially sensitive, however, there is another filter to apply:

As a founder, you are responsible for shielding your team from stress and uncertainty. Be fully transparent until sharing information you possess will increase stress or create uncertainty.

When you made the decision to start a company, you made the decision to climb aboard the craziest roller-coaster of your life. And if you’re lucky, that ride won’t arrive back at the gate for years. Sorry.

(To anyone who still believes it would be “fun”, “romantic”, “sexy”, or “cool” to start a company, please forgive me for shooting down those notions. You will be in for a rude awakening even before you hire your first employee.)

Every company, even in the top-percentile of the most-successful, experiences dramatic turns of fortune continuously and rapidly. I can’t count the number of times my outlook and mood has gone from on-top-of-the-world to the Marianna’s Trench in the space of an hour.

I write about startup founders because, as a population, they typically have the least management experience and mentorship support relative to the importance and seniority of their role — however much of this can be applied to managers at all levels in all types of organizations.

Founders who are not prepared for this struggle endlessly with the emotional component of entrepreneurship. And those without an experienced co-founder or a strong mentor to lean on often fall into the trap of passing their stresses or uncertainties onto their team because it makes them feel better.

You can’t.

Your team didn’t sign up to found a company. Sure, they wanted the excitement of joining something early stage. They wanted to be part of a small, tight-knit group. They want to make a real impact, and perhaps help lay the groundwork for some new technology. But they didn’t sign up to found a company, and that’s why you aren’t compensating them at that level.

The difference between a founder and an early employee is quite simple: if they are drawing a salary on their first day of work, they are an employee. If you compensate them only with equity, they are a founder and should be considered as such. The typical equity cliff between founders and early employees reflects the stress, uncertainty, lack of salary, and risks that the founders should be absorbing.

Besides, if you want your team to be productive, you need to give them a clear direction and the space to execute. Don’t burden them with the stress you should be shouldering for them (and working on a strategy and setting priorities to address the source of).

So, let’s get concrete.

Transparency with Core Financials

I’m surprised by how often the founder intuition is to keep core financial metrics — bank account balances, revenue, monthly burn rate, runway — a secret from the rest of the company. I’ve never understood this.

Your team (I assume) isn’t stupid. It’s not that hard to realize that the company (as is the case with substantially every startup) is spending more money than it is making, and thus its runway isn’t infinite. This isn’t rocket science. One of the easiest ways to build trust and credibility with your team is to share (monthly or quarterly) your business’s core financials. By doing so, you’re clearly communicating that you’re on top of the financial health of the company and that you hold no illusions about the state of your business. It’s the perfect opportunity to share your high-level fundraising timeline, goals for customer/revenue growth, and retrospectives on major accounts or partnerships that have churned recently.

Trust me, your team will be far less stressed knowing that there is ten months of runway left and that you expect to secure additional funding in six, than they will be worrying in the dark that they won’t have a job at some point in the next year.

Transparency with Compensation

A number of companies, such as Buffer, have made waves in recent years with policies claiming that they are “fully transparent,” even to the point of openly sharing salary and compensation details internally. On net, I do not believe this is productive or stress-reducing.

Let me be clear: your business should have no statistically-significant compensation bias across any demographic sub-population. Compensation should be correlated solely with start date (early employees take more risk, and are compensated more for it), skill-level (not seniority), and criticality to the company’s execution against strategic priorities. You should not be opaque here because you have something to hide.

That said, I generally believe that the tech world today has propagated an over-obsession with wealth-generation, and that competition and jealously too quickly makes its way to the forefront. If you feel pressure to share compensation data publicly, you likely have larger and deeper issues to address.

What’s important is that each individual on your team believes they are being compensated fairly for their role given the resources of the company, and that you as the founder are operating the company with their best long-term interests in mind.

For example, when an employee’s personal situation permits it, I strongly prefer to under-cut the market on salary and over-pay on equity with the goal of further aligning our incentives. In some cases, their personal situation demands the reverse. You can imagine, in this scenario, the confusion, conversations, and accusations that would ensue if salary information was shared openly. Taking the time to explain it deeply would not only expose the personal situations of each member of your team, but also create a costly distraction wholly irrelevant to your company’s priorities.

I view the salary-equity balance as a see-saw, and it’s critical that you understand which is more important to the candidate at the time you’re putting together their offer. Under-paying on salary, when possible, also has the surprising effect of reducing time-consuming “I need a raise” conversations, because your shared focus is on the long-term outcome.

Transparency with Customer Feedback

The larger and more successful your company becomes, the more secretive you or your teams will want to be about the honest state of your product in the market. How do customers really feel? What is the NPS score? What are the biggest issues? Where are your competitors stronger? Which large accounts churned recently? How effective is your customer support team?

Secrecy here is both dangerous and damaging.

The moment you, your leadership team, or your product/engineering groups aren’t honest about the state of your offerings is the moment you start losing the market.

This sounds obvious, but once you have more than one product or feature team, intra-company competition begins. Whose product is more successful? Growing more rapidly? Driving more revenue? “My product doesn’t have bugs; the customers love it! But that team’s product sucks!”

As the founder, it’s your job to set the leadership tone with fair, accurate articulations of the state of each product, their strategy and goals, and their challenges. Celebrate each of your teams’ successes and challenge them on each of their failures. But most of all, enforce a culture of open, honest evaluation of what the customer thinks.

They are, after all, always right.

Transparency with Acquisitions

Congratulations! You’ve heard someone’s interested in buying your company? Quick, share this great news with the team! They’re going to be overjoyed!

Think again.

I’ve experienced this twice first-hand (and in stark contrast) while building my first company, Increo, and my second, Crashlytics.

When my co-founder, Kimber, and I sold Increo to Box in 2009, we were completely transparent with our team about the process. The company was in a challenging position (we were running out of money — Sequoia had foretold the bad times) and we thought we were doing the right thing by keeping everyone in the loop.

Unfortunately, even the smoothest acquisitions take a lot longer than people think and bring with them the highest-highs and the lowest-lows of the startup roller coaster. Even if the deal is moving well, there will still be days when it will seem completely off the table. And even when it looks like a certainty, it isn’t — acquirers routinely look at dozens of companies for every one they buy, and often play them off each other to secure the best deal.

The more details we shared with our team regarding the acquisition, the more stress they began to internalize. They didn’t understand the process, and more importantly, they didn’t know how to prioritize what they were working on in their day-to-day roles.

“Do we build this product feature that we might need for the acquisition?”

“Do we build what our current, long-term customer wants?”

The acquisition process lasted three months, and we built almost nothing during that time.

It was as if the company had come to a halt — because everyone was too stressed to focus, and even then, nobody knew what to focus their energy on.

While the acquisition by Box was ultimately a success (Increo’s technology powered Box’s file preview feature for 5+ years), I had failed our team. And I promised myself I wouldn’t make that mistake again.

Fast forward to December, 2012. Five years ago, almost to the day.

Twitter approached us out of the blue and convinced my co-founder, Wayne, and I to come out to their office in San Francisco (Crashlytics was Boston-based) to discuss a deal. The timing was right around Christmas, and I was convinced we couldn’t reveal anything to the team in case it was a red-herring. Since we didn’t want to raise any flags, we took the opportunity to throw the team a holiday party and promptly gave everyone the next week off.

Wayne and I boarded a flight to SFO.

While everyone else was enjoying their vacation, Wayne and I were meeting with Twitter.

After much deliberation — and a lot of back-and-forth negotiation — we became convinced that joining Twitter was the right opportunity and the best future for the company. We looped in our lead investors and signed the term sheet — at 10 a.m. Christmas morning — without anyone on our team knowing.

When we returned to the office post-holidays, we scheduled a 2012 Year-In-Review all-hands, with the last photo of our deck showing Wayne and I in San Francisco, at Twitter.

The team was caught completely off-guard. The company was going great and growing rapidly, what was happening?

Since we never told our team about the acquisition conversations, they had no ability to ever give any input. Their entire fate was in our hands — their jobs, their compensation, their future careers.

As a founder, if you’re not 100% transparent about something, then you’re implicitly demanding your team’s trust. Live up to it.

When Twitter acquired Crashlytics, almost the entire team had been with us for less than a year. The way equity works, it usually vests over 4 years with a 1-year cliff, which means Wayne and I could have wiped the slate clean — given the team nothing — and kept the entire deal for ourselves.

We did the opposite.

We fully-accelerated everyone’s vesting all 4 years. Because they trusted us. Because we owed everything to them.

Today, 6 years after most of them joined, the original Crashlytics team is still together — now at Google — because we sold the company yet again, without telling them, but only with their best long-term interests in mind. ♥︎

They picture the boss in the corner office, standing behind her desk, gazing out over the city. They imagine someone calling all the shots, and everyone relying on their insight and wisdom — a visionary who is never wrong. They fear being grilled, berated, and guilted into working long hours — inevitable top-down command-and-control.

When startup founders take this approach today, they fail.

In my experience, this couldn’t be further from the true purpose of the role.

Yet, too many founders fall into the trap of trying to live out this image — and I’ve seen their startups underperform or even fold as a result.

Over the past decade, I have founded and exited two companies — Increo and Crashlytics — and then stayed on to build large teams at the acquirers — Box and Twitter. And as an angel investor in 30+ startups and entrepreneurs, I have had the opportunity to see the role’s function outside of myself, and the successes and challenges that different founders’ approaches beget.

Through these experiences, I’ve learned that the humbling role of the founder is about putting others in a position to succeed beyond their wildest dreams. Your role as a founder isn’t to be in charge of everything, all the time. In fact, it’s the opposite.

The more involved you are with the day-to-day work, the more difficult it will be for you to scale, and the less likely it is that your company will succeed.

Every founder believes they have no time, they have too many priorities, and they have 100 different roles they need to play. I disagree.

As the founder/CEO, you have one job: Look at where you’re spending your time, then fire yourself from that position.

Here’s what I’ve learned that makes this possible:

1. Perform The Role, Then Hire Someone Better

The best founder/CEOs are jacks-of-all-trades.

Their value doesn’t come from doing one single thing exceedingly well. It comes from being able to perform an array of things fairly well, and then having the awareness to find someone better than them to take over those responsibilities — allowing them to move on to the next most-important role and the next most-consequential hire.

Leave egotism out of it: you should always be able to find someone who can perform a given role within your company better than you can — and that’s a good thing. (If you honestly can’t, play that role instead and question whether there is someone better than you at being CEO…)

You’ve probably heard the CEO role compared to the conductor of an orchestra, but in a startup, you’re more likely the conductor of musical chairs:

The founder has no choice but to start in whatever role is most necessary for the company to exist. He or she learns the role, understands its function and measures for success, and then fires themselves from that position and passes those responsibilities to someone else. The founder then trains the newly appointed person up, provides context for how to best succeed in that role, and then moves on to the next role — and so on, and so forth.

When I was building Crashlytics in 2012, this was exactly my process.

For those who don’t know, Crashlytics is a mobile crash reporting service that was acquired by Twitter (2013), and later acquired by Google (2017). From the day of launch, we scaled rapidly, growing the product to over 300 million iPhones in the first year. Today, Crashlytics operates on over 3 billion active devices.

At the very beginning, though, my job wasn’t to direct a room-full of engineers or motivate a sales team. There weren’t any. Crashlytics was just an idea — which meant my full-time priority was to code and prove-out the product.

Once we hired our first iOS engineer, I gave him context as to what we were working toward, introduced him to the codebase, and shifted my responsibilities to working on the backend. When we hired our first backend engineer, I shifted to frontend. When we hired a frontend engineer, I transitioned to fundraising, and helping my co-founder with marketing and PR.

I moved in circles, like musical chairs, always making sure I was spending time where we were light and needed the most help.

This was how we slowly (but surely and confidently) built our team from the ground up. We intimately knew the type of people and skillsets we had to hire, because I was playing each role myself before hiring for them.

2. Hire People to Help you Hire

If you’re doing this well, you’ll quickly reach the point where the company will outgrow your own ability to “chair hop.”

Instead of filling one role at a time, you’ll be filling three.

When we had a team of six engineers at Crashlytics, I realized I was spending nearly all of my time recruiting. I was putting up job postings, scheduling interviews, and performing a role that could have been done far more effectively by someone else. Someone better than me.

As my co-founder Wayne would put it, this meant reassessing our “build order” — choosing how we invested our capital in order to continue growing and what role we should hire for next.

So we hired a full-time recruiter.

Most startups withhold this hire for later in the game, but from our perspective it was a huge opportunity cost. The more time I spent sifting through candidate resumes, the less time I had to chart our course in the market and identify the next big challenge coming down the road.

And it worked — the recruiter we hired was so vastly better than me that we tripled our team in the next five months.

(Hat-tip to Aaron Levie for the original kick-in-the-pants to do this. In a future company, I would hire a full-time recruiter even sooner.)

3. Bring Top-Down Context, Not Top-Down Decisions

As the founder/CEO, you are in the single position that can see across roles, across skill-sets, across your market, and across your customer base. That is your unfair advantage. You aren’t better than your team, but you certainly have more context than your team. How can you use this to empower them?

I like to picture my org chart upside-down. They don’t report to me. I report to them. What do they need to succeed at their roles? Context to prioritize. Context to make decisions. Context to know when to push for more resources, or when to make-do.

When done correctly, this gives your team superpowers: they will be able to make the right decisions and prioritize what is most important without you having to hand-hold every conversation. And this gives you superpowers too: the time to focus on forward-looking strategy and risks instead of the day-to-day.

As the founder, you should be making 10% (or less) of all the key decisions in your company.

In fact, if you have to make a decision, it likely means you’ve already failed in some other way:

• You haven’t filled that specific role yet.
• You’ve hired the wrong person for that role.
• You’ve hired someone at the wrong seniority for that role.
• You haven’t shared enough context with them.
• You haven’t clearly defined their areas of responsibility.
• You haven’t empowered them to make the decision.

One of the greatest skills a founder/CEO can acquire is a talent for deference. I know plenty of founders who struggle to let go of direct responsibility, or fear letting other people drive parts of their business.

If you’re unsure how self-sufficient your team is, ask yourself, how many times do you use the word “defer” in a day?

“I’m going to defer to Sarah on this decision.”

“I’ll defer to Tom on that.”

Deference shows your team that you trust them to make their own decisions. And it shows yourself that you’ve put the right people in the right roles. The sooner you learn to empower your team to make decisions on their own, and the sooner you give them the context required to make the right decisions, the faster you will be able to fire yourself from day-to-day work.

All in all, so many founders forget that the ultimate goal is to make themselves completely unnecessary to the day-to-day operations of the company.

This sounds counter-intuitive, but trust me, there will always be someone better than you at every position in your company. And you should be excited to hire people who are smarter, more specialized than you at each individual skill set. They are the ones who will ultimately supply you with the time (and head space) to steer the company as a whole to market success.

The irony of course is, as a founder, you’ll never be completely unnecessary to the business. In constantly trying to “fire yourself” from different roles, the company will continue to grow. As it grows, new responsibilities and challenges will arise, and you’ll have to repeat the process of getting people up to speed all over again.

But that’s the point.

The moment you stay married to any one role, you’ve stopped searching for your next replacement, and the company has begun to stand still.

You never want to be standing still.