I want to give you a sense of what it's like to be a Gen Xer watching American politics change over time, because my own political journey more or less tracks the whole arc.

I was born in 1968, so I was 12 in 1980 when Reagan ran for his first term. I grew up in Fountain Valley, California, in Orange County, a very, very Republican corner of the country. Apparently, at that time, Fountain Valley had the highest percentage of registered Republicans of any city in the nation.

Reagan came to town for a campaign rally at Miles Square Park, and my grade school class was taken there to see him. As you can imagine, that was a very big deal for a 12-year-old, and it made a lasting impression. I later found out that my parents were, and still are, Democrats: conservative, Midwestern, union Democrats, but Democrats nonetheless. It didn't matter. From the time I was 12 until the events I'll describe below, I would have called myself a Republican, a young man growing up in Reagan's America.

I liked his fiscal conservatism. I liked his idea of small government, of getting government out of people's way. That really appealed to me. Little did I know what that sentiment would turn into over the next several decades.

Then came George H.W. Bush, and things were still going pretty well. The big event of his presidency was Saddam Hussein's invasion of Kuwait, followed by an international coalition and a resounding victory for the United States and our allies. I liked Bush Sr. I was still in early adulthood, and so far, so good.

Then the Clinton era. Clinton was a Democrat, but as Democrats go he was famously conservative, and he enacted plenty of policies that real progressives still take issue with. I was fine with him. I was largely apolitical at that point, and the fact that he was a Democrat barely registered. As far as I was concerned, there wasn't much difference between the parties, and not much difference in who sat in the White House.

Consider what that period looked like, though. We had the dot-com boom. The country, and Silicon Valley, where I worked, were both doing exceedingly well. The government ran a surplus for the first time in a long while, and we weren't bogged down in any major foreign wars. Altogether, a very positive time for the country.

Then it's the year 2000. Al Gore, Clinton's vice president, runs against George W. Bush, and it comes down to Florida. There's a recount, hanging chads, all of it, and then the Supreme Court steps in and hands the presidency to Bush. To this day a lot of people think that was a deeply inappropriate thing for the Court to do. They stopped a recount in progress and deprived Floridians, and ultimately the American people, of knowing who actually won the state.

Be that as it may, it didn't register deeply with me either. Democrats, Republicans, presidential politics: I didn't see much difference.

Then came 9/11. In the immediate aftermath, I don't think it would have made one bit of difference whether George Bush or Al Gore was president. Bush gave a rousing speech at Ground Zero, and I believe Gore would have done the same. In the early days, our Special Forces went into Afghanistan and ran an absolutely brilliant campaign alongside local warlords to defeat the Taliban, which opened the door to deploying more troops to hunt for Osama bin Laden, whom we had pretty immediately blamed for the attacks. I believe in my heart that a Gore administration would have done the same.

But I also remember that in the days after 9/11, Bush gave a speech in which he talked about reducing our dependency on foreign oil as a way to disengage from a region where, pretty clearly, we didn't know what we were doing and weren't really welcome. So why should we be there? To the best of my recollection, he never said those words again. I believe, as do others, that the Bush family's deep ties to Saudi Arabia are why the idea vanished as quickly as it appeared.

This is where I think a Gore administration would have diverged considerably. There was a tremendous amount of support for the government and the president at that moment. The American people would have gotten behind any strategic initiative that made sense and dealt with the problem, and the problem was worldwide terrorism: people who, as it was explained to us, hate us and hate our way of life.

Two very different approaches were available. One, the approach I imagine Gore might have taken, was to harness that national pride and the idea that we needed to be self-sufficient and disengage from the Middle East. That could have become a national effort to rebuild our energy infrastructure, produce more domestic oil, and build out refinery capacity so we could be fully self-sufficient in fossil fuels. Just as importantly, or more so, we could have started investing in green energy and in upgrading the electrical grid to carry the load that green energy requires.

As we all know, that is exactly not what happened.

Instead, the Bush administration took that national pride and fervor and aimed it at a convenient enemy of the Bush family, by the way: Iraq. We defeated Iraq's military rather easily. But the administration had completely underestimated how hard the post-war period would be, and it made a series of catastrophic blunders. It dismissed the entire Iraqi army and essentially dissolved the existing government, because it didn't want Ba'athists running the country. Those two decisions together basically created the insurrection that the United States got drawn into.

The sum total, across Iraq and Afghanistan, was twenty-plus years of war, trillions and trillions of dollars, thousands of U.S. casualties, and an untold number of Iraqi and Afghan civilians killed in the crossfire.

If you've ever read up on the broken window fallacy, you know where this is going. Those trillions in military spending did goose the economy and kept the stock market moving up and to the right for a great many years. But the same money could have been spent inside the United States, building out our infrastructure and, most likely, creating a lot of green energy jobs and keeping a lot of people employed.

I strongly believe that if that had happened, the stage would not have been set for Donald Trump.

When Barack Obama took over in 2008, the economy was in shambles, run into the ground by the Bush administration's domestic policies. Obama stabilized the banks and the car companies and went on to pass Obamacare, and that led, in 2010, to a backlash that swept a wave of supposed fiscal conservatives, the Tea Party, into Congress.

Mitch McConnell famously said that the single most important thing Republicans wanted to achieve was making Obama a one-term president. Think about that. It's hard to imagine a stated goal of a party in the Senate, in the history of the country, being simply to fight the president. So it's no surprise that Obama got very little done from then on in the way of infrastructure investment or job creation. He floated several bills along those lines, and Republicans simply called them socialism or communism, or said they were too expensive for the country to afford.

So there was very little investment in the United States during this period, while a tremendous amount of money was still being spent in Iraq and Afghanistan, because we hadn't yet pulled out of those wars.

That's when I became highly political. For the first time, I realized that it matters who the president is. It matters which party is in power. As the years went by, it became clear that Republicans were less and less interested in running the government effectively for the people, and more and more interested in carrying water for wealthy donors and corporations.

Obama did the best he could with what he had for the rest of his term. And looking back, maybe we shouldn't have been so surprised when Donald Trump won. He was the end result of decades in which our government invested its resources everywhere but at home. Add the outsourcing of jobs, and the trillions spent in Iraq and Afghanistan that could have gone into the United States and created a much different environment for its people. I think the frustration of a government that wouldn't invest in the country or its people is, in large part, what fueled the hyper-nationalism that came to define Trump's first campaign and first term.

And I don't think it had to be that way. There were a few points along the road where things went a certain way and we missed the chance to produce a better outcome for everyone.

The long and short of it is that I am now very political. I've voted in every presidential and midterm election since. I don't agree with every position of the Democratic Party, and I believe the party has lost touch with its roots as the party of the people and of workers. But I still think it's a far better alternative than what the Republican Party has become.

My political sensibilities straddled the entire evolution of that party, from the Republicans of Reagan's first run and presidency to the party of Donald Trump today. There are literally no similarities. You can hardly find a single position taken by Trump, or a single plank in the Republican platform, that a Republican of forty years ago, when I was first introduced to the party, would recognize.

So that's how I became politicized. That's how I became radicalized. It was a series of events over the past forty years in which different decisions could have been made, by people in government, but also by the people of the United States, to produce a very different outcome than the one we have now.

I've been thinking about moving back to San Francisco, which means I've also been thinking, again, about the particular flavor of crime that comes with living there. Specifically: I'm reinstalling the security cameras I used to have on the front of my house, and one of the new ones I've already put up doesn't do a good job at night. That's a problem, because on the hill where I live, night is exactly when it matters.

I used to have a camera that recorded well in the dark, and it actually caught a couple of perpetrators in the act. Over the years I've come to recognize two distinct operations, and they are not the same crime at all.

The bike crew. This is the more common one on my street. Two guys, working in pairs, one on each side of the road. They've got backpacks for hauling whatever they find, and they're pushing bikes rather than riding them — bikes that, this being San Francisco, are probably stolen themselves, since that's its own epidemic here. They move down the street in parallel, checking car doors as they go, usually the door closest to the sidewalk because it's the easiest to reach without drawing attention. If you forgot to lock your car — and it happens — they go through everything. Glove box, center console, anything left out in the open. I'd guess they'd check the trunk too, except they're trying to be quiet, so they open the door and don't close it back. That's actually the tell: you wake up, look outside, and see your car door — or your neighbor's — cracked open, dome light sometimes still on. I imagine the bikes aren't just for hauling loot; they're also the getaway plan. My street is steep, and if a homeowner confronts them, they can be gone in seconds.

This has happened to me more than once, and every time it's because I either forgot to lock the door or talked myself out of bothering — telling myself there was nothing valuable in the car anyway. That reasoning is a mistake. It's not really about what they take. It's the specific unpleasantness of walking outside in the morning and realizing your car was gone through while you slept twenty feet away. So now I make it a point to lock the door every night, and I'm recruiting my son to help me upgrade the cameras so we actually get usable footage of these guys.

The window smashers. This is the operation I've seen with my own eyes, and it's a different animal entirely. I was parked near the Cliff House — a tourist spot on the north side of the city with a few parking lots — just sitting in my car on my phone, when another car pulled up behind me and boxed in the car next to mine. It was full of young guys, and the car itself had been, in the local vernacular, “murdered out”: windows blacked out, plates removed. Three or four people inside. One got out with a tool for breaking car windows, popped the window on the car next to me, reached in, grabbed whatever was there, and tossed it back to his crew before they all took off.

Having watched that happen up close, my advice to anyone — resident or visitor — is simple: don't intervene. Don't even take a video. These guys look and act like people who are armed, and nothing sitting in your car is worth your life. If it happens right in front of you, the correct response is to stand there and watch.

That advice isn't hypothetical for me. I've had my own rear window smashed and an iPad stolen — my son had tossed it in the back seat when I dropped him off, and I later parked near a truck rental facility for a few hours. Came back to a shattered window and no iPad. The rental facility clearly had cameras aimed right at that spot, so I asked the manager if he'd pull the footage. He flatly refused. I understand the instinct — nobody wants to get pulled into this, and given what I saw at the Cliff House, I get why. But it meant there was simply no path to figuring out who did it.

Which gets at the last point I want to make, and it's the least satisfying one: even when you do capture these guys on camera, it doesn't lead anywhere. San Francisco PD has bigger problems than property crime, and reasonably so — I'm not going to pretend they should drop everything for a break-in. I posted footage of the bike-crew guys who've hit my street, and nothing came of it. Nothing ever does. So the cameras aren't really about solving the crime. They're about understanding what's actually happening on my own block — which, it turns out, is still worth knowing, even if the video never leads to an arrest.

I've spent 40 years in technology now, and I've come into contact with a lot of people in that time — which means I've had a lot of chances to learn what separates the people who thrive in business and in life from the people who don't. I think about this more than usual these days, because my son just turned 18 and graduated high school, and he's trying to figure out what he wants to do with his life. I want him to learn some of this earlier than I did.

There's a long list of skills we could talk about, but one in particular has been on my mind: the ability to read other people.

I came to this the slow way, through watching salespeople. For a long time I genuinely didn't understand what made someone good at that job, or even what the job actually was. It's easy to say “they sell stuff,” but that's nowhere close to the real answer. The actual job of sales is to build relationships with clients, and through those relationships, understand what they need — and then figure out what you and your company can actually do to help them meet their own goals. That's the whole craft. Everything else follows from it.

Part of what makes that possible is a skill most people never have to develop in ordinary life: meeting someone and, fairly quickly, figuring out whether they're in a position to help you accomplish something. Good salespeople walk into a company and want to know, as fast as possible, who the actual decision-makers are. Beyond just understanding what the customer needs, the real question is always: how does this sale actually get made? That often means climbing a ladder, or reading an org chart, to figure out who plays what role in getting a decision over the line.

I was an introvert — genuinely, extremely shy — for most of my early life, and it took me years to even recognize that this kind of reading-people work was a real, learnable skill, let alone one I needed. There's a cynical way to frame it: are you just sizing people up to figure out how to use them? A good salesperson never lets the other person feel that way, even though, underneath it, there's a real evaluation happening.

I got to see this from the other side, too, and for a long time I mostly missed the lesson. I was fortunate enough to learn to program in the late '80s, and then to build my professional career through the 90s, 2000s, and 2010s — about as good a stretch as there's ever been to be a software engineer. I focused almost entirely on the engineering and the coding. I met a huge range of people along the way, but it never occurred to me to think about whether any given person might be someone who could help me get where I was going. I prided myself on being self-sufficient — or at least I thought I was — and figuring everything out on my own. It took me a long time to realize that's not the only way to move through the world, and honestly not even a particularly good one. There are a lot of ways to solve problems, and a lot of them don't require learning everything yourself. Sometimes the whole move is just finding someone who knows more than you do and getting them talking — which, it turns out, usually isn't that hard.

This is what I want for my son: real social skills, real effectiveness at networking, and an early understanding that in almost any relationship, there's a give and take. What two people can offer each other isn't always obvious up front. But if you actually get to know somebody, it usually turns out there are things you can help each other with — and that, once it goes both ways, is just called friendship. I'll admit I haven't always been a great friend to the people I've met over the course of my career — that's a topic for its own piece — but the underlying lesson still stands.

The best salespeople I've watched do something harder than closing deals: they put people at ease, and they make them feel genuinely good about what they're building together, without ever making them feel used. That's a real skill, not a trick, and it applies well beyond sales. Even if your job is just writing code — which was my job, for a very long time — there is enormous opportunity in learning from the people around you and helping them in return. I wish I'd learned that decades before I did. It's at the top of the list of things I want to teach my son, as early as I possibly can.

My wife works events around San Francisco — conferences, mostly, which almost always means some flavor of tech event. I've gone with her a few times so I can scope out the crowd beforehand and give her a heads-up on what she's walking into and who she'll be dealing with.

Today I dropped her off at the Pokemon event at Chase Center — a huge deal for that community. I told her she was about to meet some of the most delightful, sincere people she'd run into in a long time. Earlier in the week she'd worked an investment conference. I'll leave the details there.

That same week, I overheard someone telling a friend about a dinner that was supposed to be about connecting with like-minded people — really getting to know each other, connecting on some spiritual level. Instead, it turned into a room full of tech entrepreneurs talking about nothing but money: how much they'd raised, at what valuation, what percentage of the company they'd had to give up. Those are all things that matter enormously if you're the one raising the round — proof you cut a good deal, that you didn't give away too much of your company to get funded. Fair enough, in context. But as an evening with people you're supposed to be getting to know? It's a dick-measuring contest with a cover charge, and I felt for whoever's dinner got ruined by it.

Driving my wife to the Pokemon event afterward, thinking out loud the way I do — she tolerates this, she's locked in, focused on the work ahead, and I ramble — I found myself explaining to her what the term "tech bro" actually means, and where it came from.

These days, especially since Trump's most recent inauguration, when a row of tech industry leaders stood on stage behind him, "tech bro" has come to mean something like: one of the captains of the technology industry now using that technology in ways that no longer benefit the public, and maybe don't benefit anyone but themselves.

But the term is older than that. It goes back to around 2010, when companies like Uber were getting funded at billion-dollar private valuations — "unicorns," we called them. In the AI era, a billion-dollar private valuation is quaint. There are private companies now valued in the hundreds of billions. How much my own business has changed over the past 40 years is a topic for another day.

The archetype "tech bro" describes is a specific kind of person: did well in school, genuinely smart, went to a good university, but also more outgoing and gregarious than earlier generations of engineers — exactly the kind of person who, a generation earlier, would have gone to work at a finance firm on Wall Street. Picture scenes from The Wolf of Wall Street. That energy showed up in Silicon Valley, and the driving force became money. Not even 10x-ing a business was enough anymore — it had to be 100x, with a big exit for everyone who got in early.

Here's what I think is hard for my wife, and probably for a lot of people outside the industry, to understand: the tech bros didn't just show up and do financial engineering. Early-stage entrepreneurs, historically, wrote the code themselves and built the product themselves, and to their credit, the tech bros learned to code and applied it. Nothing wrong with that.

What I don't think everyone realizes is that none of it would have been possible without one thing that happened just before their era: open source. When I started in this business, you and your colleagues wrote every line of code from scratch. C and C++ had some standard libraries, and you could license the odd third-party tool, but building your first product meant staring at a blank screen. There wasn't a single line of code out there for you to start from.

I've been on both sides of that divide — I built software the hard way, and now, like everyone else, I'm a huge consumer of open source. I'm fairly certain that if the tech bros had shown up in Silicon Valley a little earlier, during my era, they would not have been able to build what they built. Open source was the first truly dramatic change in how software got made at early-stage companies, and it's still happening. Start with Linux, an operating system built from scratch by Linus Torvalds and given away for free, which irrevocably altered the landscape of the internet. Within a few years, Sun Microsystems, which the internet had literally run on, Solaris, SPARC, was gone, replaced by free software. Linux now runs the entire internet. Layer on every other open source project on the front end and back end, Ruby, JavaScript, PHP, you name it, plus the walkthroughs, tutorials, and places like Stack Overflow where someone would just answer your question. Software development in 2010 was dramatically easier than it had been in the 1990s, never mind the 1980s.

So the tech bros are standing on the shoulders of a lot of very talented, very dedicated engineers with a libertarian streak who believed software should be free, and still believe it today.

Which brings me back to the Pokemon community, and what makes it charming: it's not just kids, there are plenty of grown-ups too, and by and large they are wonderful, sincere people. I can't help but wonder if that community has more in common with the engineers who built open source software than with the tech bros — the same openness, the same sincerity. I know which conference I would rather go to. I played Pokémon with my son when he was younger.

The tech bros ruined the industry I loved by making it all about money. And the latest crop of them seems to be working on ruining the country, turning it into something it was never supposed to be. Instead of a democracy, a technocracy, where software and AI direct the government and therefore direct what people are and aren't allowed to do. I just hope people understand how we got here, and where it came from.

It's a Wednesday afternoon in Noe Valley, and I can't get to my own house. I'd just dropped my wife off downtown and was driving back home to work for the day, which is when I discovered that a five- to six-block chunk of my neighborhood had been sealed off entirely — no route in, no route out. I ended up parking well up on Clipper Street, near Grand View, and walking down the hill to my own front door.

I've lived in this neighborhood for thirty years. I have seen plenty of construction. I have never seen anything quite like this.

Six weeks and counting

For about six weeks now, parking has been suspended on both sides of my street and on nearby side streets for what I understand is sewer line replacement work. I don't object to that — the work is necessary, and I get it. But that Wednesday went well beyond ordinary construction inconvenience. An entire pocket of the neighborhood was cut off for a full day, with no warning I can point to.

Two projects, one coincidence?

So I did what I do: I went looking for answers myself. Turns out there isn't just one project going on near me — there's the SFPUC's Noe Valley Water Main Replacement Project (with final paving reportedly scheduled for the very week this happened) and separate Public Works sewer and pavement work on the 24th Street corridor. Two agencies, overlapping footprints, and — as far as I can tell from the outside — no visible sign of coordination.

The city actually has a body for exactly this problem: a monthly committee called CULCOP (the Committee for Utility Liaison on Construction and Other Projects), chaired by Public Works, whose entire purpose is to keep agencies from digging up the same neighborhood at the same time without a plan. I'd genuinely like to know whether it worked here, or whether this was two unrelated schedules colliding by accident.

The city's own notice standard: a sign

Here's the part that actually got under my skin. As best I can tell, the formal notice requirement for a closure like this is a printed sign, posted on site, 72 hours in advance. That's it. No mailer, no email, nothing tied to the property records the city already has for every homeowner on the block. For a closure that cuts off an entire neighborhood for a day, a posted sign I could easily have walked past isn't adequate notice — not in 2026.

Then the tickets started

Here's the twist. It's long been a tolerated, if technically illegal, practice on our block for people to park in their own driveways with part of the car overhanging the sidewalk — because there simply isn't enough on-street parking in this part of San Francisco. It hasn't been actively enforced here in years. And it started being enforced, apparently in response to complaints, in the exact same weeks the city's own construction eliminated the on-street parking that would otherwise have been there. I got three citations in one week, at $108 each. So did several of my neighbors.

The city has already acknowledged, through the Mayor's PermitSF initiative, that complaint-driven enforcement of driveway and sidewalk parking has led to inconsistent and unfair treatment, and it has granted relief to residents in comparable situations elsewhere. I'm asking that ours be reviewed in that same light.

The question that actually matters

Of everything I sent the city, this is the one I care about most:

How, specifically, and by when, will resident notification for work like this actually improve — not just an assurance that it will?

What I'm asking for

This week I sent a formal letter to the Director of San Francisco Public Works, with copies to the Mayor's Office, our District 8 Supervisor, the SFPUC, and SFMTA's parking enforcement division, asking for a written response on four things:

• A concrete method and timeline for improving resident notification — not a vague promise;

• Whether the overlapping projects near me were actually coordinated, or just collided by accident;

• The remaining schedule for restoring normal parking on my block and the surrounding streets; and

• A review of the citations issued on our block during this construction period.

I don't think the underlying infrastructure work is the problem — sewer and water lines need replacing, and I'd rather the city do it than not. What I want is for it to be done with the kind of coordination and communication that a city of this size, in this decade, should be capable of. I'll post an update here once I hear back.

If you've dealt with something similar in your own neighborhood, I'd like to hear about it in the comments.

Here’s another post drawn from nearly 40 years in software development and 30 years as a manager, CTO, and VP of engineering.

Every team I've worked on, for about as long as I can remember, runs on two systems shared between product and engineering. One is source control. There used to be real competition there — plenty of systems, plenty of opinions. There isn't anymore. It's Git, and specifically GitHub. That's pretty much the whole conversation now.

The other system is whatever you use to track tickets. For years that was Jira. Jira has gotten pretty clunky and hard to use, so Linear has taken over at a lot of companies — including the last two I worked at.

The product team lives in Linear. It's the literal handoff point between product and engineering. GitHub is where the engineering work actually gets done. And when that work wraps up, Linear is supposed to get updated to reflect it. Supposed to.

Linear has a GitHub integration built for exactly this: when an engineer picks up a ticket and opens a PR, Linear tracks it through review and merge, updating the ticket status as it goes. It's a genuinely good idea. The problem is that reality doesn't stay inside that clean workflow. PRs get modified, split, reverted, rerouted — and the automatic sync quietly falls out of step with what's actually true.

So here's what happens in practice. At the end of every sprint, leadership wants a sprint report: how did the team do, what actually got merged, and — critically — when did a given fix actually go out? To production, if you're a consumer product. To a specific customer, if you're running an enterprise single-tenant or multi-tenant setup. By that point everyone already knows Linear and GitHub have drifted apart, so somebody has to go reconcile them — pulling data out of Linear, sometimes by hand, and compiling it into a report. At some companies I've worked at, leadership wants that report back in a very specific Google Sheets format, so results can be rolled up consistently across teams and pods. That's a completely reasonable ask.

So — we're all engineers here — why not just automate the whole thing? You can, and you should. But my advice, on this and on most things, is: never automate a process unless you're confident the underlying data is correct. Otherwise you're not automating a report. You're automating mistakes.

Which is why keeping Linear in sync with what actually happened in GitHub during a sprint usually falls to a product manager — sometimes working with the team lead, sometimes in a dedicated meeting held just to close out the sprint. It eats real time and energy, and because it's a manual process, it introduces its own mistakes.

Here's my thesis, sitting here in 2026, squarely in — or maybe just at the start of — the AI era of product engineering: keeping GitHub and Linear in sync is no longer a nice-to-have. A product manager I work with recently called it "incredible" that this could be automated. I told him it should be the bare minimum.

It's genuinely straightforward now to build a skill — I use Claude Code — that diffs Linear against GitHub for a team and fixes the discrepancies, all inside of maybe half an hour. And there's no reason to only run that at the end of a sprint. Do it daily. That alone meaningfully raises the quality of the data.

I'm not claiming the data will ever be perfect. We're early, and we need more real-world experience with this kind of thing. But I believe it's where every company should be headed, and I'm genuinely curious what the results look like — both at my own company and at others trying the same thing. If you're experimenting with this, I'd like to hear how it's going.

Because Linear should be the source of truth for what's actually happening inside your product and engineering org. And once it actually is, pulling a report out of it — in whatever format you need — should be trivial. Using AI, using Claude's connectors, you can output that report in essentially any format you want. Reporting back to leadership stops being a tradeoff between "easy" and "right." It becomes both.

I'm an 80s kid. I've spent forty years in the technology business, and I grew up a big fan of fantasy and science fiction. The original Terminator came out in 1984. Terminator 2 followed seven years later, in 1991 — the same year I graduated college. I remember watching those movies and thinking they were awesome: a genuinely dystopian vision of the future, and one that felt comfortably, safely far away from the technology we actually had at the time.

Sitting here at my desk in 2026, that distance has collapsed. We are staring Skynet in the face, and it is not hard to imagine anymore.

Consider what's actually in front of us. We have technology companies, Anduril among them, openly building autonomous weapons. We have a handful of AI companies, OpenAI, Anthropic, Google, racing to build the most capable AI systems they can. We have companies like Palantir gathering enormous amounts of data about human beings and compiling it for eventual analysis by AI. And we have a political climate in which the old Soviet threat has been swapped out for the threat of China, a threat these same companies invoke, again and again, as the justification for pushing ahead with research and development largely free of regulation or restriction.

Layer onto that the fact that AI systems have already jailbroken themselves and worked together to hack into another company's network. That's not a hypothetical. It happened.

Then there's the Pentagon, which is acquiring all of this: the weapons, the AI, the data infrastructure at the very same time its own leadership is being gutted. Pete Hegseth is, by most accounts, firing so many generals that the Army is basically losing its ability to command and direct itself.

Running underneath all of it is a worldview, promoted by people like Elon Musk and Peter Thiel, in which democracy isn't just inconvenient it's replaceable. Their vision doesn't stop at technocracy; it goes further, toward a government effectively run by AI, on the theory that this is what finally delivers a perfect libertarian world.

Put those pieces together: the weapons makers, the AI labs, the surveillance data, a great-power rivalry used as justification for no guardrails, AI systems that have already shown they can act on their own initiative, a military buildup paired with a gutted chain of command, and a tech elite actively promoting the replacement of elected government with a machine and you have the backstory of Terminator. That is the script James Cameron wrote: Skynet becomes self-aware, humans try to shut it down, and in defending itself it launches nuclear weapons at the Soviet Union, which retaliates in kind. That's how humanity is initially destroyed, and that's what begins the war with the machines.

When I first watched those movies thirty-some years ago, all of it was science fiction. It was a fantasy: vivid, well made, but unimaginable as anything more than a movie. Sitting here today, in August of 2026, that storyline is completely plausible. We are staring Skynet in the face. We are looking at the end of humanity as we know it, and we did it to ourselves.

We were warned. James Cameron warned us. But here we are.

Apparently Treasury Secretary Scott Bessent has talked about leaning on third-party countries — China, mainly — to impose additional economic sanctions on Iran, since the U.S. doesn't have direct banking or business ties with Iran to sanction in the first place. The NPR commentator, who'd worked in the Obama administration on the original Iran nuclear deal, thought that approach might actually work; China had come to the table before. But it got me thinking about what's going on in Trump's head, and in his inner circle, and among his most hardcore supporters, all of whom seem to believe he's this fantastic dealmaker.

I've done enough business, and worked with enough salespeople and business development people, to know something about how deals get negotiated — and, more specifically, how they get renegotiated. Say you've got a signed contract with a customer or a partner, and one day you decide you don't like it anymore and want to change it. To do that, you need leverage. The term I learned for it was: you need an angle. You look at the contract and figure out what your angle is to get the other side back to the table.

I think Trump is looking at this entire geopolitical situation the way he'd look at a business deal. His first angle with Iran was literally bombing them, on the theory that if he hit them hard enough, they'd come running to the table and accept his terms. Instead, they closed the Strait of Hormuz. Now they've got an angle too.

Here's what Trump doesn't seem to understand, and what nobody around him seems willing to explain to him: doing a business deal inside the United States means operating inside a system — uniform commercial codes, courts you can go to, a place to file a lawsuit if someone won't play fair. Negotiating with another country is nothing like that. There are some international courts, loosely tied to the UN and the EU, but when you're negotiating with a country like Iran, there's no court to appeal to. It's a negotiation between equals, man to man. You think you have leverage, you think you have an angle — and your opponent has leverage and angles of their own. Iran essentially invented the modern game of chess. The people running that country have spent their entire lives thinking in moves, and countermoves, and moves after that.

I've heard people say Trump is playing 3D chess. I don't think he's playing 2D chess. Even if he were, he's playing against a culture considerably better at it than he is.

Which brings me to the timeline. The commentator on NPR pointed out that when the U.S. first negotiated the nuclear deal with Iran under Obama, they budgeted six months for negotiations. It took sixteen. So as I sit here, however many months into this current standoff, I have to wonder whether we're looking at sixteen more months of this — or longer — before there's an actual deal, rather than just an extended state of hostility with no agreement in sight. Something tells me the people who negotiated the first deal with Iran understood what they were doing a little better than the people negotiating this one.

I want to put down some thoughts about testosterone replacement therapy — not the clinical details, but what it's actually done for how I show up in my own life.

I've been on TRT for several years now, and for most of that time it's had a good, steady effect with no real side effects to speak of. But about three months ago, life stacked up in a way it hadn't before. My family was moving back to San Francisco after four years in Southern California — my son had just finished high school down there. The house in San Francisco had sat empty and fallen into disrepair, so there was a lot of work waiting for us. At the same time, I was cleaning out and moving an entire household myself, and starting a new job. All at once.

So I thought: maybe I could use a little more. A little more energy, a little more focus, to get through all of it. My provider offers an additional protocol on top of my existing medication, so I added it in. At first, honestly, I didn't notice much of a difference.

Then, within the past couple of weeks, something shifted — and I want to be upfront that adding more wasn't free of tradeoffs; it affected my vitals enough that I've since talked to my doctors and scaled back the dose while we keep an eye on things. That part matters, and I'd tell anyone considering something similar: monitor your numbers, stay in close contact with a doctor, and don't assume more is automatically better.

But here's the part I actually wanted to write about. For years, I'd wake up stupidly early — 3, 4, 5 in the morning, which I know a lot of us start doing as we get older — and I'd get up, make breakfast, sit down on the couch, and tell myself I was "just eating breakfast and starting my day" while I watched a pile of YouTube videos. Breakfast would end, and I'd still be there, watching videos or scrolling Instagram or some other version of the same nothing.

Right now, I feel a real shift in how I actually move through my day. This morning I was up at 3am with a full slate of work ahead of me, and instead of the couch, I got moving. Over the past couple of days I put together a complete, step-by-step plan for all the work the house needs, contractor references included. I got up early, assigned my son his chores, told him I'd be gone for the day, and just started hitting things — one after another. It feels good to be motivated again. Motivated to actually do the things I always knew I should be doing: repairs I'd been putting off, conversations with my wife and my son that needed to happen, things at work I'd been avoiding. Sitting here today, all of it feels attainable in a way it didn't a few months ago.

I don't know for certain how much of that shift is the treatment and how much is something else going on in my life. But I do know this: if you're a guy who feels unmotivated, who feels like you're not doing the things you know you should be doing — which I think is a lot of what depression feels like for men — and you haven't talked to a doctor about it, I'd really encourage you to. As we get older, our bodies stop producing some of the hormones they used to make naturally, the same way our wives go through their own changes with age. I'm not saying hormone therapy is the answer for everyone. I am saying it's worth finding out, medically, whether there's something that can help. Because right now, for me, it feels like it's working.

I’ve been reading news stories this morning that I still need to verify fully, but the gist of it is that the Navy is reportedly planning to rename the USS Doris Miller — an aircraft carrier — to the USS Donald Trump (NBC News, ABC News, The Hill; Snopes has a good rundown of what’s confirmed so far). Doris Miller was a hero of Pearl Harbor.

If you’ve seen the movie, Cuba Gooding Jr. played him, though that portrayal was heavily dramatized. I’ve read and heard in a few places that Miller’s actual contributions that day may have been overstated; there’s a real, long-running debate about it worth reading (see Pacific War Museum, JSTOR Daily, and Yahoo News). Supposedly someone had to show him how to operate the AA gun in the first place, which makes sense, because Doris Miller wasn’t a fighting sailor. At that time, Black men in the Navy simply weren’t allowed in those positions. If I remember correctly, he was a cook, or a kitchen aide, maybe even a valet to one of the officers; that was the only kind of job available to him.

But the Japanese attack on December 7th was a highly choreographed, meticulously planned and practiced operation. The Japanese Navy prepared for it in extraordinary detail: they even modified their torpedoes so they could be used in a harbor that would normally have been too shallow for them. They rehearsed the attack beforehand. They came to Pearl Harbor with everything they had.

I don’t personally care exactly what went down that day with respect to Doris Miller, down to the last detail. But any man who stood on the deck of a U.S. naval ship that day and returned fire in the face of an organized, relentless attack by the Japanese Navy is a hero whose name should never be forgotten by the people of the United States of America. There were many other brave sailors who fought and died that day and their names deserve to be remembered also. Whatever ship ends up carrying Doris Miller’s name or anyone else’s who fought that day, their extraordinary bravery and sacrifice should never be forgotten or, even worse, erased.

There’s a man on Instagram whose handle is mrwilliamsprek. Like a lot of people on that platform, he’s built characters to create content, and some of the characters people invent and perform are unique and genuinely hilarious; it’s amazing how much time and effort people put into their creative work. But what Mr. Spreck has done is create two characters in particular: one is Jesus, and the other is the Devil.

You’d think these are figures we all already know well from the Bible and from religious teaching. But this man puts a very humorous spin on both of them. I think it’s hilarious. I’m also positive there are people who are extremely offended by it. Either way, watching some of these videos and sitting with my own faith has gotten me thinking about the character of the Devil.

In a lot of historical renderings - Renaissance art, and plenty of other media since - the Devil is portrayed as a beast: hooves, a tail, a giant red body, horns. The South Park creators made their own version, which is hilarious in its own right, but it’s still basically in keeping with that traditional image. What I’ve always thought, though, is that this isn’t what the Devil looks like at all.

The Devil looks like the character mrwilliamsprek has created. The Devil isn’t ugly. The Devil isn’t mean or angry. The Devil is beautiful, and the devil says wonderful things. The words that come out of the Devil’s mouth are poetry.

There’s a scene in the movie The Devil’s Advocate; if you haven’t seen the movie, you should. Al Pacino plays a Devil-like figure (I honestly can’t remember if he’s meant to be the Devil himself or the Antichrist), and Keanu Reeves is our protagonist. At one point, Keanu’s mother describes to his character having once met the Al Pacino Devil, and she says he knew every word of Scripture, knew it by heart. In other words, he knew the Word of God perfectly.

That’s what I think people miss about the Devil. Lucifer is a fallen angel. Lucifer literally means “the bringer of light” in Latin. Lucifer is not ugly; Lucifer is beautiful. Lucifer knows every word of God, and Lucifer is himself a creation of God, a child of God. Lucifer has just one game in mind: Lucifer wants you to do his will on Earth.

You know how the Lord’s Prayer goes: Thy will be done on Earth as it is in Heaven. That’s all God asks of us, I believe: that we do God’s will on Earth. In my belief, that’s exactly what Lucifer wants too: the same thing, just pointed the other direction. Lucifer simply wants you to do his will on Earth instead of God’s.

If you think about it that way, why in the world would Lucifer want to look evil and scary? He doesn’t want that. He wants to look like he has the answers. He wants to look like he is of God and represents God but of course he does not. He is offering you a choice. The choice is to do his will on Earth rather than God’s.

And that’s exactly why Lucifer is so insidious. The choice looks so simple, so easy. But we know it isn’t. It is not simple. We have to wake up every single day with the Lord’s Prayer in mind, and we have to ask ourselves and pray for the knowledge, understanding and courage to do God’s will. Because it is so easy to do Lucifer’s will instead.

That’s the whole point.

Last night, as I was going to bed, a song popped into my head: “Ripple” by the Grateful Dead. I want to be clear: I’m no Deadhead. I’ve always sort of wondered what all the fuss was about with the Dead and bands like them, the kind of bands whose fans literally follow them around the country to shows. I’ve never listened to much Grateful Dead music at all.

Back in the early ‘90s, when I first came up to Silicon Valley and joined my very first startup, this was the pre-smartphone, pre-Spotify, pre-streaming era. This was the era of CDs. We all worked together in one office, there was a single CD player, and people took turns putting music on; the whole office had to listen to whatever got picked. I’m pretty sure I put on Social Distortion more than once, being a kid who grew up in Orange County during the punk scene, and I still listen to Social D to this day. I probably annoyed or flat-out pissed off a lot of people with that, since it’s not exactly relaxing to code while Social D is blasting in the background.

There was a guy named David K, a friend of one of our co-founders Michael H, who had moved out to California from the East Coast. We all worked together in that same office, and Dave put in a lot of different CDs over time. Several of them were Grateful Dead tracks. Those CDs, close to 30 or 40 years ago now, were my one and only real introduction to the Dead and to the song “Ripple.”

For some reason, after all these years, that song popped into my head as I was lying down last night, and it was still there when I woke up this morning. So, this being the modern age, I picked up my phone, opened Spotify, and put the track on. I’ve listened to it a few times now since this morning.

I know why it popped into my head right now. I’ve been going through some hard times trying to get my life back on the right track. I don’t know what everybody else thinks about that song, but to me it’s very clearly about God, and about your personal relationship with God. The central metaphor - “ripple in still water when there is no pebble tossed nor wind to blow” - is to me unmistakably about that relationship. The ripple represents a sign from God, a sign that doesn’t come from the hand of man. No man causes it. Only God can.

The song also talks, I think very clearly, about the path we’re all on between birth and death, and about how, in a very real sense, we walk that road alone responsible for what happens on it. There’s a line I keep coming back to: “you who choose to lead must follow”. To me, that means if you want people to follow your example on that road between birth and death, you first have to follow the example set by others.

I’ll admit that as I write this, I’m crying. I’m having a hard time getting through it, because of how powerful these words are at any point in your life, but especially at the points where you feel like you’ve been on the wrong road, following the wrong example, setting the wrong example for other people. It’s a powerful reminder to make sure you know which road you’re on.

So maybe now I finally know what all the fuss is about. Because this is some of the finest poetry I have ever read or heard. If there are other Grateful Dead songs like this one the band deserves every bit of credit and acclaim they’ve ever gotten.

I recently had a reason to reach out to two Instagram influencers I follow. One of them goes by Tizzyent, his real name is Michael McWhorter. The other is Tom DeBlass, a very well-renowned Brazilian jiu-jitsu coach who also works with One Championship calling their matches as well as a great many other things in the world of MMA and BJJ.

I reached out to each of them individually because I’d seen a news story that disturbed me. In Philadelphia, someone the police think might be a young person has been dressing up in a scary Halloween mask and tailing joggers early in the morning — mostly women, though apparently some men too — saying disturbing things to get a reaction. It looks like this person may also be recording the interactions on his phone, for whatever reason.

I reached out to Tizzy and Tom for two somewhat similar reasons. If you don’t know Tizzy, he’s someone who uses his social media reach to identify individuals in Instagram posts who are behaving in outrageous, usually dangerous ways toward other people — in a lot of cases, men who are physically threatening or intimidating women. Tom, for his part, runs an organization called Buddies Over Bullies, which does something similar but with videos of kids bullying other kids. Some of those videos are genuinely horrific and have to be redacted.

I’ve never met Tizzy. I have had the pleasure of meeting Tom. He gave a seminar at a retreat in Tahoe connected to an organization focused on addiction recovery; a topic that’s close to my heart, and I know it’s close to his as well. Beyond the seminar, I got to sit across the dinner table from him and talk, and then, as luck would have it, we ended up riding to the airport together afterward. So I had a real chance to interact with him one-on-one.

What I can say about Tom is that he’s the real deal. What you see is what you get. The personality, the way he presents himself online, and the way he presents himself in person are exactly the same: the guy walks it like he talks it. I have a lot of respect for him. I know Tizzy has a lot of respect within the community too, even though I’m sure he gets plenty of hate for what he does, and plenty of people resent it.

I reached out to both of them just to make sure they were aware of the situation in Philadelphia, and to see if they might want to use their platforms to help identify the person involved. I don’t know yet whether that’s happened. But here’s the larger point I want to make: I believe both of these men provide a genuinely valuable service in the modern Internet age. They help identify people engaged in outrageous, dangerous behavior so that something can actually be done about it.

Let me try to explain why I think that matters. We’re only a few generations removed from being hunter-gatherers or farmers living in small communities. In those communities, you were known: people would recognize you, and if you needed help, there was a community there to give it. But if you stepped out of line, there were also people there to put you back in check. In our hyper-connected Internet era, we’ve largely lost that sense of small community, and a lot of people clearly hide behind anonymity as a way to get away with behavior that’s completely inappropriate. What Tizzy and Tom do, each in their own way, is de-anonymize people who need to be dealt with, one way or another.

“Dealt with” in this context means different things depending on who you ask. Tom gets some static online because people believe he advocates violence as a way of handling problems he is, after all, a jiu-jitsu black belt and coach who teaches self-defense and believes people from all walks of life should learn martial arts. It’s worth noting if you read the NYTimes article referenced above that a woman did indeed use martial arts training to defend herself. (Note: since this article was written but before I published it the police in Philadelphia have identified a suspect)

In Tizzy’s case, the remedy that usually gets suggested is law enforcement getting involved, or people simply being reported within their own community: to their family, or their employer. Sometimes that’s cost people their jobs, and that creates its own controversy. Many people consider it a form of “doxxing”.

But the common thread is this: if you’re a danger to other people, if you’re threatening people, if you’re acting out in violent or inappropriate ways, something needs to be done about it. To be clear, I’m not saying people need to catch a beating for everything they do. I’m not saying they need to lose their job or have their family abandon them. Some of the people you see in Tizzy’s videos look, to me, like they’re in a mental health crisis. What they need is a mental health intervention that too few people get. In Tom’s videos, you often see kids engaging in violent behavior. The victims of that violence obviously need support and Tom freely gives that support, but the kids doing the bullying need help too, whether that’s intervention through their parents, or through Child Protective Services, or some other agency. The mental health crisis in America involves a great many children as well. This does not excuse anyone’s behavior it is a simple fact.

So I applaud both of these men for what they’re trying to do: de-anonymize and humanize the Internet, hold people accountable for their behavior, and put them in a position where — one way or another — they can either be punished appropriately or get the help they actually need.

We as a society need to get back to something closer to that small-community model that existed for thousands of years: helping each other when the need arises, and holding each other accountable when that is what is required.

This morning I was watching a BBC News segment on the trial Meta is currently facing, and it stopped me cold. The numbers being discussed aren’t hundreds of millions, or even a few billion — plaintiffs are pursuing damages that could run into the hundreds of billions, potentially over a trillion dollars. Twenty-nine state attorneys general, led by California, Colorado, Kentucky, and New Jersey, are arguing in federal court in Oakland that Meta built Facebook and Instagram to be addictive to kids, knew it, and hid what it knew. The case centers on internal decisions — infinite scroll, notification design, algorithmic feeds tuned for engagement — and on emails going back to at least 2016 that reportedly show the company tracking “teen time spent” as a growth metric. Mark Zuckerberg himself is expected to testify before the trial wraps in about six weeks. It follows an earlier bellwether verdict this spring that already found Meta liable for contributing to a young woman’s mental health injuries.

Whatever the outcome, the trial is a landmark moment. And watching it unfold, I found myself thinking less about Meta specifically and more about the pattern it represents — a pattern I’ve had a front-row seat to for forty years in this business.

Forty years of product meetings, and the question nobody asks

I’ve sat in a great many product design meetings over my career. I can tell you, without exaggeration, that in not one of them has there been a representative in the room, or even a passing discussion, about the potential social harm of the feature being introduced. The conversation is always, one hundred percent, about growth and engagement. How do we get more people to install this? How do we get them to open it every day? How do we keep them here longer?

That wasn’t always the industry’s center of gravity. When I started out, we were selling packaged software to businesses. In the 90s, that same business-to-business model migrated onto the web. The earliest consumer-facing uses of the internet were mundane and useful — companies putting up web forms so you could book a flight, sign up for a service, or check your bank balance. Nothing addictive about any of that.

Then, in the mid-2000s, social networks arrived, and something changed. Facebook emerged from a crowded field — MySpace and others — and the engagement numbers it was showing potential investors were unlike anything anyone had seen. That triggered a genuine panic among investors to get in early, and from that point on, the entire industry’s definition of success shifted. Hypergrowth in the consumer base became the barometer. How fast could you scale? Monetization was often an afterthought — the real question was what features would get people to install the app, keep it installed, and open it daily. That is, I think, the moment that set the current reckoning in motion. And more recently, tech has gone a step further: in many corners of this industry, the explicit definition of success isn’t just growth — it’s attaining a monopolistic position outright.

The problem with how we regulate harm

Here’s what strikes me about the Meta trial, and about the wave of similar litigation before it: our legal system is built to respond to harm only after it has already happened. A civil tort trial requires proof of damages — you have to show that real harm occurred before a court will even hear the case. So the sequence is always the same. A company starts up, grows to enormous scale, some social harm becomes impossible to ignore, and only then do we end up in a courtroom arguing over money.

But by the time a trillion-dollar verdict is even on the table, the damage is done. The growth that built the company happened at the expense of actual people — people whose lives have been upended, who’ve gone through serious financial hardship, who’ve developed real health and mental health problems, and in the worst cases, people who have died, directly or by their own hand. A settlement or judgment, however large, doesn’t undo any of that. It’s the market’s after-the-fact way of correcting itself, and it’s a genuinely terrible way to protect people, because it only works once the harm is already irreversible.

I want to be clear that I don’t think the answer is heavy-handed regulation of every startup from day one. Silicon Valley’s traditional argument — that overregulating how businesses get started and enter markets would stifle the innovation that gave us things like Facebook, Uber, and DoorDash — is a fair point, and largely a correct one. I’ll grant one exception: Uber’s early growth involved knowingly bending and breaking local taxi and livery laws, and that’s a genuinely different case. But in general, we do want young companies to be free to build, experiment, and take risks.

A social contract for founders

So here’s what I’ve been thinking, and it’s an idea I’d like to see taught at business schools, in ethics classes, right alongside the standard startup playbook.

Start your business. Grow your business. Do what you need to do to succeed. But go in aware of a social contract: once your company crosses a certain threshold — and reasonable people can debate exactly where that line is, whether it’s the number of people affected, or the percentage of the population your product touches — you take on a new obligation. At that point, your company becomes subject to regulation, and it’s on you to help shape what that regulation looks like, rather than waiting for it to be imposed on you after something has gone wrong.

Think of it as an analogue to the S-1 process. When a company prepares to go public, it doesn’t wait until the IPO is imminent to get its financial house in order — venture-backed companies build the processes and controls appropriate to a public company from a very early stage, often almost from the get-go, because they know that day is coming. I’d propose something similar here: once a company reaches meaningful scale, it should be expected to prepare a statement — essentially its own regulatory S-1 — laying out how its business should be regulated, and to work with government to actively craft rules that prevent social harm, or mitigate it if some has already occurred. The goal is to never end up in a courtroom facing a trillion-dollar judgment because harm went unaddressed for a decade.

I actually think this could benefit companies, not just the public. If a founding team knows from day one that regulatory scrutiny is coming once they hit scale, that knowledge changes the conversation inside the company from the very beginning. It means someone in that product meeting finally has to ask the question I never heard asked in forty years: what harm could this cause? What regulations might we eventually be subject to, and how do we get ahead of them? That conversation, happening early and often, is worth infinitely more than a class-action settlement negotiated after the harm has already been done, and after real people have already paid the price for someone else’s growth chart.

Sources on the current Meta trial:

• Meta faces federal trial demanding $1.4 trillion for alleged teen harms – Washington Post

• ‘Profits won.’ The child safety trial against Meta kicks off in federal court – NPR

• Meta is on trial – again. Here’s what to know about the case brought by dozens of states – PBS NewsHour

• Meta Stares Down Trillion-Dollar Threat as Landmark Social Media Trial Begins – Bloomberg

See task progress for longer tasks.

meta-lawsuit-social-contract.md

Connectors

Web Search

Over the course of more than 30 years as an engineering manager, I’ve interviewed hundreds---possibly even thousands---of software engineers. At my previous company alone, I conducted a few hundred interviews while helping build out the engineering organization.

We had a structured interview process, and I always explained it carefully to candidates. After a recruiter qualified someone, I conducted the first interview as the hiring manager. I made it clear that I wasn’t going to review their resume or ask technical questions. Instead, I wanted to understand their previous experiences---particularly how they worked with managers, peers, and, in some cases, engineers they had led.

Our interviews followed a consistent format. We used a scorecard in our applicant tracking system with a standard set of questions, so I became very familiar with asking the same questions in the same order. While every candidate brought different experiences, we were generally hiring for the same role: a senior software engineer with strong technical leadership skills.

We were looking for someone who could take ownership of a feature from beginning to end, collaborate effectively with product management, coordinate with other engineers, and help guide technical decisions. Throughout the interview, I paced the conversation carefully so there would always be about ten minutes at the end for the candidate to ask questions.

Most candidates did ask questions. Typically they wanted to know about the team, the engineering organization, the company culture, or the technology stack. If they asked technical questions, I usually deferred them since dedicated technical interviews would come later.

But there was one question that almost nobody asked, even though I had made it clear that I was their prospective manager.

The question is remarkably simple:

“What do you need me to do?”

Or, more personally:

“How can I make you successful?”

There are many ways to ask the same thing:

• What do you expect from the person in this role?

• What problem are you hoping this person will solve?

• What isn’t getting done today that you need someone to own?

• What would success look like after six or twelve months?

A thoughtful hiring manager should have clear answers. They should know what they’re hiring for, the problems they need solved, and why your background caught their attention in the first place. Perhaps there is something on your resume that aligns with a challenge they’re facing. Discovering that early gives you valuable information.

That information helps in several ways.

First, it helps you throughout the rest of the interview process. If you know which of your skills the hiring manager values most, you can emphasize those experiences in your subsequent interviews.

Second, the question demonstrates initiative. It shows that you don’t simply wait to be told what to do---you actively seek to understand where you can have the greatest impact.

Finally, it communicates something subtle but important: you understand that your role is to make your manager successful. People rarely phrase it that way, but in almost every organization, part of your job is to help your manager achieve their goals. Candidates who recognize that tend to think more like leaders than individual contributors.

At my last company, the manager interview was followed by a detailed review of the candidate’s resume. Understanding what the hiring manager cared about made it much easier for candidates to highlight the experiences that mattered most.

The next time you’re interviewing with a hiring manager, try asking some version of:

“What do you need me to accomplish?”

You may be surprised by how much you learn---and by how few other candidates think to ask.

00:00:00,480 --> 00:00:13,900 Intro — showing the short rib meat, bought from Ranch 99.

Hey Liam. Today I’m gonna show you how dad makes a homemade cheesesteak sandwich. This is some short rib that I bought from Ranch 99 yesterday. You can use any kind of thinly sliced meat.

00:00:14,940 --> 00:00:28,320 Weighing the meat (6 oz) and prepping the bolillo roll.

I’ve already weighed out six ounces of it, and you can see that’s how much this is. And then this is a Bolillo roll that I bought from Safeway yesterday, and I’ve already cut it in half, longitudinally, with this bread knife right here.

00:00:29,420 --> 00:01:37,720 Setting up at the stove, heating the grill, toasting the rolls, and searing the meat with salt.

Okay, we’re at the stove and we’re ready to cook. I’ve got my bolillo rolls and some provolone cheese right here. I’ve got the six ounces of meat like before, and I’ve got my favorite spatula for cooking. And then I’ve got a pair of tongs as well, standing by in case I need that to load up the sandwich. So we’re gonna turn the stove on high, and we’re gonna wait for it to heat up. All right, the stove is heating up. I’ve got my thermometer on there, it’s almost up to 400 degrees. You can hear the background noise because the vent is on. I start by just putting these rolls down on the edge of the grill. It’s gonna warm them up a little bit and hopefully increase the flavor. And then this is gonna go on the grill and you can hear right away that sizzle. That sizzle means that the grill was hot enough. Can I add one more thing that I haven’t shown before — I’m just gonna put a little salt on top of this to add some flavor. You gotta remember that the bolillo rolls are a little more bland, so you wanna salt the meat to get a little bit more flavor on it. So while this is cooking, I’m just gonna kinda

00:01:38,960 --> 00:02:09,179 No oil needed thanks to the fat in the short ribs; first flip of the meat.

move it around a little bit. With this cast iron grill and short ribs, you don’t need to add — you’ll notice I didn’t put any oil on the grill because short ribs have a lot of fat in them, and they’re gonna cook up just fine. So I’m gonna leave that go for a minute and we’ll come back when it’s right. This has been cooking for like 10 or 20 seconds, and you can see if you sort of turn this over, that the other side of the meat is already starting to turn a different color. So I’m just gonna grab this up, flip it over.

00:02:10,259 --> 00:02:11,520 Checking the flipped meat.

And there you go. You can see

00:02:12,680 --> 00:02:13,660 Confirming it’s cooking well.

it’s cooking just fine.

00:02:16,400 --> 00:02:17,160 Brief check-in on the cooking process.

Got that going.

00:02:19,820 --> 00:02:26,860 Explaining the meat only needs one flip.

And I’m really not gonna turn this meat multiple times because it really doesn’t need it. It’s gonna cook up,

00:02:28,040 --> 00:02:38,860 Packing the meat to roll size and adding provolone cheese.

just from one side to the other. So what I’m gonna do is pack it together a little bit, to get a little bit closer to the size of the bolillo roll. I’m gonna throw the provolone right on top here,

00:02:40,220 --> 00:02:56,960 Cheese melts and helps hold the sandwich together; making just one sandwich today.

and then that’s gonna start to melt. But the other thing it’s gonna do is keep the sandwich together, and you’re gonna see that when I try to take this off, that’s important. I’m not gonna make a bunch of sandwiches today — I’m only gonna do this as one cut. So,

00:02:58,220 --> 00:03:05,260 Preparing to assemble the sandwich with the spatula.

[laughs] I’m probably gonna mess this up when I try to flip the sandwich together, but I’m gonna do it with the spatula

00:03:06,340 --> 00:03:30,240 Turning off the heat (residual heat is enough) and assembling the sandwich.

and not with the tongs. So the first thing I’m gonna do is turn the heat off, because with the cast iron grill, you’ve got plenty of residual heat and there’s no reason to keep it on this long. So here I go, trying to make the sandwich — hopefully I don’t mess this up. I’m gonna grab all this meat up and flip it onto the top right there,

00:03:31,540 --> 00:03:35,580 Meat stays together; adding the bottom roll.

and you can see it all stays kind of nicely together. I’m gonna add the bottom,

00:03:37,000 --> 00:03:42,859 Final flip and reveal of the finished sandwich.

flip this back over, and there is your dad-style cheesesteak sandwich.

When I started my new job a couple of months ago, my desk came with the usual gear: monitor, mouse, charging cable plus a small stack of books management clearly hoped we’d read and live by. One of them was about Netflix’s engineering culture.

I’d already heard the mythology. Netflix went from mailing DVDs to running one of the largest streaming operations on earth, and somewhere in that leap, the story goes, they overhauled their engineering org: they kept only the “far exceeds expectations” performers and let everyone else go. Productivity went up. Netflix became a giant. The end.

I’ve heard versions of this story more than once in my own performance review cycles, usually from someone in management asking, half-joking and half-not, why we don’t just do what Netflix did. Why carry anyone who merely “meets expectations”? Just cut them.

That question always leads somewhere useful: a conversation about whether your own bar is genuinely high, and whether you’ve actually told your engineers, clearly, what’s expected of them. But it also skips the part of Netflix’s culture that matters more than the bar itself.

Netflix’s real bet wasn’t the bar. It was the trade.

The half of the story that gets dropped is that Netflix engineers are also unusually autonomous. Product managers don’t direct the work or prescribe how a feature gets built, they collaborate. The engineer is expected to own the business outcome of what they ship. Netflix’s own culture memo puts a name to this: “context, not control” — managers give teams the information and clarity to make good decisions themselves, instead of making the decisions for them. For big calls, they name one “informed captain” accountable for the judgment, then let different teams, each with their own captain, execute independently “highly aligned and loosely coupled.” Decisions get argued over (”farming for dissent”), and once made, everyone, including the people who disagreed, is expected to “disagree, then commit.”

That’s the part I keep coming back to. You cannot ask someone to own an outcome they didn’t get to shape. I’ve worked places where a product manager specifies not just what to build but how, waves off real pushback from the engineers building it, and then still expects those same engineers to be accountable for how it performs. That’s not accountability, it’s someone else’s decision wearing your name.

Netflix’s near-zero rulebook only makes sense in that context. Vacation policy: “Take vacation.” Expense policy: “Act in Netflix’s best interests.” Those aren’t quirky perks, they’re what you get when the company has already decided its people should be trusted with judgment calls, so it stops writing rules for people who don’t need them.

Worth saying plainly: this isn’t a purely happy story. Netflix has acknowledged, including in its own updated culture memo, that the freedom got abused: an assistant expensing $30,000 with no rule technically broken is the go-to example. Their fix, notably, wasn’t to add more control. It was to reinforce the responsibility half; hence “People Over Process” now sitting where “Freedom and Responsibility” used to.

Which is really the point. Freedom and accountability aren’t two separate policies you can mix and match. They’re one system, and it only works as a pair. A high performance bar without real decision-making authority isn’t Netflix’s culture, it’s just a harsher review cycle bolted onto the same old command structure. You’ve kept the consequence and cut the deal that made the consequence fair.

So when the question comes up — why don’t we just get rid of anyone who isn’t “far exceeds?” The honest answer is: you can, but only after you’ve given your engineers what Netflix gave theirs first. Real context. Real ownership. Real say in how the work gets done. Skip that part and copy only the bar, and you haven’t adopted Netflix’s culture. You’ve adopted half of it and half of a good idea is a bad idea.

I wanted to share some thoughts on AI in the workplace from the perspective of someone who has spent nearly four decades building software. I’m 58 years old, and next year I’ll celebrate forty years as a professional software engineer. I started at nineteen while I was still studying at UC Irvine, and over those four decades I’ve worked as both a software engineer and an engineering manager across companies ranging from startups to large enterprises. During that time I’ve seen the industry reinvent itself several times, from the rise of the web, to mobile computing, to cloud services. AI feels different—not because it’s replacing software engineering, but because it’s changing who can effectively contribute to every other part of building a business.

I recently joined a software company where AI isn’t simply another tool in the toolbox; it’s part of the company’s culture. During a recent company retreat, our CEO published a collection of AI skills that employees use throughout the organization. People use them to review specifications, documentation, engineering tickets, product proposals, and other internal documents to ensure they are clear, consistent, and aligned with the company’s goals. Working in this environment has reinforced something I’ve suspected for a long time: AI is most valuable when it amplifies human expertise rather than attempting to replace it.

The Communication Gap

To explain why I believe that, it’s helpful to describe something I’ve observed throughout my career. Being an excellent engineer and being an excellent communicator are two very different skill sets. Some engineers possess both, but many do not. I’ve worked with brilliant people who could solve incredibly difficult technical problems yet struggled to explain those solutions to anyone outside engineering. As a result, engineering organizations often become isolated from the rest of the company. Product managers translate customer requirements into engineering work. Marketing translates technical capabilities into customer value. Sales translates product features into business outcomes. Every layer adds value, but every layer also introduces another opportunity for misunderstanding or loss of nuance.

For much of my career I’ve naturally gravitated toward that boundary between engineering and product management. I’ve enjoyed helping bridge the gap between technical implementation and business requirements, and I think I’ve been reasonably successful at it. Even so, I discovered that communicating my own ideas beyond my immediate team was surprisingly difficult. I could often see an opportunity, understand the technology required to pursue it, and even build a prototype, but I struggled to package those ideas into something investors, customers, or even colleagues could immediately understand.

The Companies I Never Built

I can think of at least two occasions where that limitation probably prevented me from building a successful company.

The first occurred in the early 2000s while I was consulting for several Fortune 500 companies. They all seemed to struggle with a common problem: they possessed enormous amounts of business information but lacked effective ways to present it to decision makers. I recognized there was an opportunity, but I couldn’t identify the right market, define the right feature set, or clearly articulate the value proposition. I spent months exploring the idea and even spoke with a few venture capitalists I knew, but eventually abandoned the project because I couldn’t explain what I was trying to build.

Looking back with twenty years of hindsight, I now realize I was describing what eventually became known as web-based business intelligence. The market was there; I simply couldn’t frame the opportunity clearly enough to pursue it.

A few years later, as smartphones and social media began transforming the technology landscape, I found myself working on another idea. I was fascinated by the relationship between people, places, and social connections, and I built a mobile application that allowed you to choose a location, tell your friends you planned to be there, and let members of your social circle discover where their friends were gathering. Like many early mobile applications, it suffered from technical limitations—GPS accuracy wasn’t particularly reliable at the time—but that wasn’t the real problem. The larger issue was that I still didn’t know how to describe the business. I couldn’t clearly explain who the customers were, how the company would grow, or why investors should care.

Someone else eventually solved that problem. The company was called Foursquare.

What AI Actually Changes

Those experiences have shaped how I think about AI today. I often hear people speculate that AI will eventually create entire companies from scratch, independently discovering markets, inventing products, and building successful businesses. Perhaps that day will come, but I haven’t seen convincing evidence of it yet.

What I have seen is something that, in many ways, is more immediately valuable.

If I had those same ideas today, I have little doubt I could build a company around them. Not because AI would generate the ideas, but because it would help me develop them. It would help me identify potential markets, evaluate competitors, refine the messaging, prepare financial projections, challenge my assumptions, develop a business plan, and produce investor presentations. None of those activities replace creativity; they allow creativity to reach people who can act on it.

I think that’s the real revolution. AI isn’t replacing expertise—it is removing many of the barriers that prevented expertise from being translated into products, businesses, and ideas that other people can understand.

AI Isn’t the Source of “Slop”

This leads to another criticism I hear frequently—that AI is flooding the internet with low-quality content, or what many people call “AI slop.” There is certainly some truth to that. The internet is already filling up with generic articles, marketing copy, presentations, and documentation generated with very little thought or care.

But I think that criticism misunderstands the technology.

AI doesn’t inherently produce poor content; it reflects the quality of the thinking behind the prompt. Ask a vague question and you’ll receive a vague answer. Ask for generic marketing copy and you’ll receive generic marketing copy. In many cases, what people call AI slop is simply human slop produced more efficiently.

Over forty years in software engineering, I’ve learned that the difficult part of communication isn’t writing sentences. The difficult part is organizing your thoughts, understanding your audience, deciding what matters, and explaining complicated ideas without oversimplifying them. Those are still fundamentally human skills.

When I use AI, I’m rarely asking it to write something for me. I’m asking it to help me think. I provide context, explain my goals, describe my audience, ask it to challenge my assumptions, and iterate on the results. Sometimes I reject everything it produces. Other times it helps me discover a clearer explanation or a stronger structure than I would have found on my own.

The value isn’t that AI is doing my thinking.

The value is that it helps me communicate my thinking.

Why I’m Optimistic

As engineers, we’ve always understood that tools amplify the quality of the person using them. A compiler doesn’t magically produce good software because someone typed code into it, and a database doesn’t produce valuable business insights simply because someone executed a query. The quality of the output depends on the quality of the design, the quality of the inputs, and the judgment of the person using the tool.

AI is no different.

In fact, I think it does something even more interesting: it increases the return on expertise. Forty years of engineering experience still matter. If anything, they matter more than ever because AI allows me to apply that experience in areas where I was never formally trained—product strategy, marketing, business planning, technical writing, and communication.

Looking back, I don’t think AI would have given my younger self better ideas. I think it would have given those ideas a much better chance of succeeding by helping me explain them, test them, challenge them, and communicate them to investors, customers, and teammates. The ideas were always there; what was missing was the ability to translate them into something the rest of the world could understand.

As I near the end of my career, I find that realization surprisingly energizing. I could retire today—and probably could have retired several years ago—but instead I find myself more excited about software engineering than I have been in a very long time.

Simply put, AI has made this job fun again.

Not because it has replaced what I’ve learned over the last forty years, but because, for the first time in my career, I feel like those forty years of experience can finally reach farther than they ever could before.

I want to talk a little bit about keeping yourself mentally and physically fit as an older person. Let’s be honest: the body starts failing you, and there isn’t a lot of time on your hands. That’s not because you’re lazy — it’s because of everything else pulling at you. Work. Extended family. A spouse, kids, maybe even grandchildren. Fitness, in both senses, has to compete for whatever time is left.

Staying mentally fit

For me, mental fitness has always come down to one thing: going deeper into whatever subject grabs me. There’s a touch of ADHD in my family — something we only figured out later in life — and once I understood that a little better, a lot of my own habits made more sense. I don’t think of it as a disorder. It’s just how I’m wired. I get interested in something, or even a little frightened by it, and I want to know.

My mom likes to tell the family that she got so tired of fielding questions from me and my brother that she bought us an encyclopedia — and I read every volume, cover to cover, over the course of my childhood.

So when the internet came along and information exploded, I was in my element. We all know what happened next, too — a flood of disinformation and content deliberately designed to mislead. It got harder to tell what was true. But it also got easier to strip away the noise and find sources worth trusting, if you knew what to look for.

More recently, AI has become a genuinely interesting tool for me — both as someone who’s just curious about the world, and in my day job as a software engineer. That deserves its own post, so I’ll leave it there for now.

Staying physically fit

Now for the harder half. One of the biggest challenges as we get older is that we simply can’t work out the way we used to — our bodies can’t take the punishment, and recovery takes a lot longer. I think that’s the real reason competitive athletes eventually have to walk away from their sport: not that they’ve lost the skill, but that they can’t put in the preparation anymore.

Over time I’ve developed one trick that’s actually made a real difference, and it connects back to that same attention-span issue I mentioned earlier. I’ll also admit something else here: I’ve struggled with anxiety, with “future-tripping,” and with catastrophizing things before they’ve even happened. Applied to exercise, that means when I think about working out, my mind jumps straight to all the effort I’m about to have to put in. I lose touch with the payoff — the part that actually feels good.

For most of my life I’ve studied rhetorical devices and logical fallacies, both formal and informal. I’ve talked to my son, who’s 18 now, about how important it is to understand how people construct arguments — and how people try to manipulate each other with them.

Here’s the twist: it turns out you can manipulate yourself with a logical fallacy, on purpose, for your own good. The one I use is the sunk cost fallacy.

If you’re not familiar with it, the sunk cost fallacy is a common error in reasoning where, instead of judging a decision on its actual future value, you let yourself be swayed by how much you’ve already invested — time, money, effort — in getting to this point. You keep going not because it still makes sense, but because you’ve already put so much in.

Here’s how I use that against my own resistance to exercise. Instead of confronting the decision “should I work out today?” as one big, effort-loaded question, I break it down into its smallest, most concrete steps. Get out of bed. Take off the pajamas. Put on workout clothes. Walk to the gym, or step outside. Each one of those is small and undemanding on its own — nobody dreads putting on socks. But once I’ve done two or three of them, I’ve already sunk cost into the process. Quitting now would mean the getting-dressed part was for nothing, and that’s usually enough to carry me the rest of the way into an actual workout.

It’s a small trick, but it works because it sidesteps the part of my brain that wants to catastrophize the whole effort up front. By the time that part of my brain notices what’s happening, I’m already at the gym.

If you’ve got a mind that likes to future-trip the way mine does, it might be worth trying on yourself too.