pablotimer

1. To take the pressure off. I sometimes feel compelled to Go Make A Company and play the game again, but, as I'll explain below, I think there's more long-term value in taking some time before embarking on a new public journey. This timer gimmick helps me stay on the path.

2. I can point people in industry to this when they ask.

   • Saves me having to repeat explanations.

   • Maybe they get inspired!

   • Weed out bad fits. Many industry conversations feel like you're being put on a scale while the other side evaluates how useful you are in making them rich or giving them influence.

     I've been a contrarian to high-growth VC narratives for most of my career (1, 2); in my experience, most people in industry don't welcome creativity or "doing it your own way." They like the idea of contrarian narratives, and they love the word "innovation," but in practice, they're their own herd animals. If my specific kind of ambition turns off an industry contact, better we figure that out sooner rather than later.

I saw the 2021 movie Pig in late October, after I'd split from my last company, and this scene was exactly what I needed to hear:

I've spent my working life playing someone else's game. I always felt at odds with many of the aims of the game I was playing ("are high-growth, VC-backed, for-profit companies actually the best way to use technology to solve so many problems?") and the execution of it ("why does your pre-profit company need microservices on Kubernetes? Why are you so proud that your early hires come from places that haven't had to worry about a cost, or shipping a tight product, in over 15 years?").

Despite the mismatches, I played the game well, and was part of a major success at my last company. Both there and the other company where I was a founding engineer: at the start of them I felt empowered to bring my whole self. Towards the end, like virtually everywhere I worked, I felt myself pull away. After 7 companies, I need to change my approach.

As the industry matures and companies scale, they get more conservative, and end up adopting traits of their peers. I don't think the playbook works. Engineering teams are miserable, and most of the "successful" tech companies that came after the FAANG wave (you know… the last 20 years?) only recently started producing profits, and miniscule ones at that, after 9, or 10, or 11 figures of investment. Teams got stuffed with mediocre talent, hired to dig holes and fill them back up again. During the 0% era, I was surrounded by people telling me tech choices didn't matter except for how popular they were. It was full of people saying "profitabilty isn't important" while building up egregious cloud and personnel costs.

It celebrated inflated valuations, it lionized obvious hucksters because it didn't matter whether companies actually served customers or delivered value or became profitable; as long as their founders and investors got rich on selling an unrealized (unrealizable?) dream to the bigger sucker, it was a "win." MoviePass, just bleeding at a more tasteful rate. "Have fun staying poor," said a bunch of people pretending blockchains and decentralized trust could solve any real problem for the masses when they haven't for 15 years and counting.

I tried to squeeze myself into this culture because I didn't feel secure enough to truly fight for things I believed. Arguing for your principles is lonely work, and in the last few years especially, I've had some life events that required my attention. Also: making money feels awesome, and greatly improves one's life. So I played the game, but often left companies feeling hollow; I was well-liked, but not understood. I didn't feel like I was making anything better, just one flea of many on the mangy beast we like to call "capital allocation."

My last split was an especially painful one, because I really thought it could be different. I needed someone to sit me down like Nic Cage in this scene:

"They're not real, you get that right? None of it is real. The critics aren't real, the customers aren't real, because this isn't real. You aren't real.

[Pablo], why do you care about these people? They don't care about you. None of them. They don't even know you. Because you haven't shown them. Every day you'll wake up and there'll be less of you. You live your life for them, and they don't even see you. You don't even see yourself."

I'm grateful for the opportunities I've had, and I love my former colleagues. If I died tomorrow, I'd be proud of my work and my career. But I've always been an odd duck. Whatever I work on, I want to be sure that its aims and execution are things I can truly believe in and commit to, so I never lose focus and let myself disengage. I need to know I'm doing it with good people who see me and value me. If I'm honest, the strong pull I feel to Go Make A Company is to prove myself to an audience of people (really, the versions of them in my head) who I should probably leave be. We were useful to each other, and we may be again yet, but I never really fit in their game, and they won't fit in mine.

The more I think of what that looks like, I suspect it's a lifetime project, based on principles that matter to me.

It's a scary question, and I think most people don't even really ask it. I think the reason "being a parent" is such a big part of people's identities is because Life picked a project for them that is lifelong and creatively challenging, and their lives didn't (and weren't going to) have anything else like that. You don't need some Grand Purpose to live a full, wonderful life. I'm just saying a minority of people do point their lives at something, and it can be powerful.

So if you get to pick something to make your life about, what would you pick? I think the nature of what I'm considering is best illustrated by example. Here are a few, each with links and references to spend an hour to learn more and be moved, if you so wish:

Douglas Englebart and the mother of all demos. Gary Bernhardt gave a great talk on what went behind "the mother of all demos," but it was decades of dedicated work in the making, an enormous, fanciful dream for computing that was not certain to materialize or be adopted. It fundamentally shaped how we use computers, and it took 18 years:

[…] Doug Engelbart read that paper at some point between publication in 1945 and 1950, and he started working on what became NLS in 1950.

Now, 1950, Doug Engelbart is 25 years old. So he started then. He worked on it for 18 years. And when he did the demo that we've been seeing clips of, he was 43. So basically, he spent his entire adult life building the memex. And then out of that came all kinds of stuff—the mouse, of course, is the most famous thing. But all of this interactive computing stuff, some of which went on to inspire Tim Berners-Lee to build the web, which we're still using 30 years later.

Mr. Rogers Neighborhood. Fred Rogers looked at television and saw the potential of using it to do something for kids that hadn't been done before, and spent his entire adult life on that project. I know most of what I know from this documentary, which is a lovely watch. The trailer:

Braam Moolenar and vim. There's an idea of what people who change the world must look like, and a single hacker building the world's best text editor, giving it away for free, only asking if people can donate to help children in Uganda is usually not what people imagine. Here's an article about his work and legacy.

Shuji Nakamura and the invention of the blue LED. Here's a great video showing how blue LEDs (we'd already had red and green ones, with the invention of blue we could finally combine them to make white light) seemed extremely far away, until Shuji Nakamura, with a fraction of the budget and incredible focus and years of toil, found a way to do it, outcompeting engineering shops with hundreds of millions of dollars and giant teams of more qualified and experienced scientists. It changed how the whole world is lit, and I don't think it's possible to quantify the energy efficiencies it created.

Consider the projects above: could a private, VC-backed, for-profit company following "standard playbook" have produced them? That model arguably produced GitHub (though GitHub was bootstrapped and profitable for years before they took VC), but could you imagine it producing git? Never.

You'll note that many of these took time. It's not that work shouldn't be urgent too. I love this page from Stripe founder Patrick Collison on projects that happened fast, suggesting that while Rome doesn't get built in a day, speed and iteration are not only important, they are possible and probably fundamentally necessary for many of these major achievements of humanity.

My belief is that truly transformational work is about working on things urgently, for a long time. When Ramp first created company values, one was "win the marathon, sprint by sprint." This was a takeoff of something I used to say in the the founders' apartments, before we had an office: "it's a marathon, not a sprint." I'd elaborate on this in interviews: if you watch an Olympic marathon runner for 10-20 seconds, it's not that impressive. You might think "I can do that!," and you'd be right! For 10-20 seconds. What's impressive about marathon runners is that they do it for two and a half hours. That's how they cover 26 miles in that amount of time, and you can't.

If we were going to defeat Amex (and they will someday), I knew it wouldn't happen within a few years of founding. I'd say to the younger colleagues: work a weekend if you want here and there, but don't work every weekend. Hustle, don't crunch. Sleep like a human: we need you on this same marathon pace this time next year, and the year after that, and the year after that too.

So, fast!, like Patrick says, but also: there's no substitute for time. Many things in life can't be rushed, they have to be picked at. I want my next big thing to be something I can work on urgently, well until I'm an old man.

(related: the original Super Mario Bros. was released in 1985, 38 years ago, built with a team of 5 people. Last year, Nintendo released the newest Mario title, Super Mario Wonder, and 4 out of 5 of the original Super Mario Bros. team members worked on it)

1. To enjoy myself a bit before I hunker down for 20+ years of drive on something.

2. Take advantage of my current life situation: I'd like to raise kids someday, but since I'm not currently, I'd better aprovechar (Spanish, "avail yourself of").

3. Maximize the chances of picking the right thing. When you spend so long playing other people's games, it takes a bit of time to learn to listen to yourself.

It's an hour long, but I recommend this Bret Victor talk, Inventing on Principle:

He identifies a few people who decided they were going to live their life according to a single principle, and by maniacally pursuing that principle, they were able to change the world. I'm considering this approach to figure out how I'll aim my life, and I think "living my life" is the best way to find my principle.

In support of that: I believe time spent not looking directly at the problem provides insight. A thought that often sticks with me comes from a John Cleese talk (emphasis mine):

People often say, Where do you get your ideas from? And I say I get them from a Mr. Ken Levingshore who lives in Swinden, he sends them to me every Monday morning on a postcard. I once asked Ken where he gets his ideas from, and he gets them from a lady called Mildred Spong who lives on the Isle of Wight. He once asked Mildred where she gets her ideas from and she refused to say. So the point is, we don’t know. This is terribly important. We don’t know where we get our ideas from.

[dramatic pause] What we do know is we do not get them from our laptops.

In fact, we get our ideas from what I’m going to call for the moment, our unconscious, the part of our mind that goes on working, for example, when we’re asleep.

(the talk was unfortunately taken down, but he has another one here which is also great and makes many of the same points).

So I'll be pursuing a lot of extracurriculars (listed below). Because why not?

Hardly! Jeff Bezos once said (in 2017):

"When somebody … congratulates Amazon on a good quarter … I say thank you. But what I’m thinking to myself is … those quarterly results were actually pretty much fully baked about 3 years ago. Today I’m working on a quarter that is going to happen in 2020. Not next quarter. Next quarter for all practical purposes is done already and it has probably been done for a couple of years."

I observed this at Ramp. We did a lot right, and it seemed meteoric — we were New York's fastest unicorn — but candidly, much of our success came from the momentum of choices our founders made years before. Even our amazing early team: we could only build so well, and so fast, because of choices we'd made to acquire the skills, years before a single line of Ramp code got written. So I'm also going to spend these years on active work to ensure that the Pablo who launches at the end of the timer is launching from a different position than Pablo today.

Things I plan on doing in this time to help bake in that success (and I could write thousands more words on each of these):

• Build up my network. I didn't prioritize this, and while the best time to plant a tree was 20 years ago, the second-best time is right now. If you're connected to software or art in any way, I'd love to hear what you're up to, and see what help or perspective I can offer!
• Invest further in my craft. Most of us have setups that are merely "good enough," but I wonder what does it look like if we treated building software the way musicians or athletes treat their crafts, with a practice schedule? Practicals (concerts or games) and drills?
• Re-skill, particularly in ML. I've done MNIST 4 or 5 times in the last 6 years, run models with ollama, and have a decent sense of the academics and math behind Deep Learning and LLMs, but I'd love to be more empowered here.
• Fuck around and find out with side projects or quick launches. Things like Amado and PlayTabletop. There's that anecdote where a class of art students got split, with half who got graded on quantity (e.g. "you get an A in class if you submit 90 good-faith attempts at making a painting") vs. the other half who got graded on quality ("your grade will be based on your best painting, no matter how many you made"). The story goes that the "quantity" students produced better-quality paintings than the "quality" students. Many skills, you just gotta grind.

Itches to scratch

Becoming a software engineer because you like coding is like becoming a butcher because you love animals.

—Saurya Velagapudi

Nothing kills your desires or creativity for tech like the VC-backed tech industry. For years I've felt like a frayed wire, but a few months out, I'm starting to feel the itch to grow as a technologist again. As one of the most dishonest hacks of our industry liked to say, "it's time to build." Here are a few things I'd love to go deep into:

• AI, mentioned above.
• WebGL, WASM, Advanced CSS (animations, things like A Single Div). Why aren't more companies doing what Figma did and writing actually innovative, ambitious apps in the browser?
• Devtools — langserver, plugin ecosystems, DAP, coding assistants (and their limits).
• Deep program introspection tools (whole-program analysis and transformation, e.g. Python import tangles. I get embarassed for our industry for the kinds of problems we don't solve, just live with).

Additionally, non-technical (these itches are a lot healthier):

• Theatre, arts. This is my background before computers, I want to make a lot more. Maybe I go to LA and break into film?
• Music making, a dream since forever.
• Dance, fitness, music, cooking, crafting.
• Guatemala, and development economics more generally.

Those ☝️ are short-term itches I'd like to scratch, merely because I'm curious, but what's an area that looks ripe for a bigger transformation? Where I might find my "principle"? Here are a few ideas.

CRDTs and local-first software

What was the last time you had your ideas about software radically changed? What knowledge are you mad that you can't unlearn because it drives you crazy that it doesn't exist yet? For me it's the essay "Local-first Software", by Ink & Switch.

The approach they describe allows for a colossal improvement on both desktop and web software. We can have the low-latency, ownership-preserving, high-performance, optionally cloud-backed, collaborative software of our dreams! Why don't we!?

It's easy to get despondent and listen to the peanut gallery declare "worse is better," which I mostly hear as "good things aren't possible (and I'm not a curious or hopeful person)." Maybe the haters are right, and we're trapped with current paradigms. But per Englebart, if you show them a future worth having, I think people will drive toward it. So what would it take to allow that?

WASM, WebGL, localStorage — using better tech for applications run on web browsers

The other side of the coin. We're still using one of the wildest, most un-tameable toolchains to develop web applications. There's got to be a better way. I'm less clear on the mechanisms here, and have fewer Hail Mary ideas, but I wonder what applications would look like if you really pushed the cutting edge, instead of just using JavaScript and, if you're lucky, <canvas>.

Bringing back Free Software

Richard Stallman was right. Corey Doctorow has success branding the phenomenon as "enshittification," but the desire to extract rent from software has made all things for technology embarassingly worse, for no reason intrinsic to the realities of the tech, information, or machines. It's just people and power. And like other "people and power" systems that are also about wealth accrual such as feudalism, the divine right of kings, and the institution of slavery: it should probably go to hell.

It's especially insulting if you know the history of computers and software enough to know how responsible "the commons" were for getting all this tech into people's hands in the first place. Could something like Wikipedia happen in today's environment? Will Wikipedia survive me?

At one point game companies were flirting with charging fees to stream their games, and a friend said "these people would copyright your speaking English if they could." He's right. Some things work best in the private sector, but the desire to monopolize electricity running through circuits is a step too far. We suffer enough markets that sustain horrible inefficiencies to make a few people rich (American healthcare, "broker fees" in NYC); we shouldn't let that happen to computing.

I've been haunted by the opening of this excellent article:

The problem with software is that it's too powerful. It creates so much wealth so fast that it's virtually impossible to not distribute it.

Think about it: sure, it takes a while to make useful software. But then you make it, and then it's done. It keeps working with no maintenance whatsoever, and just a trickle of electricity to run it.

Immediately, this poses a problem: how can a small number of people keep all that wealth for themselves, and not let it escape in the dirty, dirty fingers of the general populace?

This is a question that the music industry faced head-on, and they came up with EULAs, enforced via the state's monopoly on violence, and DRM, a way for software to act antagonistically against its own users. Software can do useful things like encode media into bits, and then copy those bits. That's dangerously useful, and it had to be stopped.

Maybe it's time bring back a revitalized Free Software movement, one that once again strikes fear in the digital landlords.

Indie Web, self-hosting

Tied to the previous: I'd love if we didn't cede our entire digital lives — our relationships, communications, memories, news diet — to monopolists who regurgitate it back to us with ads that spy on us. The internet was fun when it was for humans, not robots.

Developer empowerment, and changing how we level up

A human being should be able to change a diaper, plan an invasion, butcher a hog, conn a ship, design a building, write a sonnet, balance accounts, build a wall, set a bone, comfort the dying, take orders, give orders, cooperate, act alone, solve equations, analyze a new problem, pitch manure, program a computer, cook a tasty meal, fight efficiently, die gallantly. Specialization is for insects.

— Robert Heinlein

It's making a different point, but: what "should" a developer be able to do, regarding software?

Almost all developers I know don't use their editors effectively. Most I observe don't develop with an active language server, or Debugger Adaptive Protocol. Most don't have a collection of snippets or an easy way to use or manage them. Most don't have AI coding assistance. Most don't know how to use a debugger. If you ask them to profile or load test a program, they have to research it, and many will make basic stats mistakes trying to interpret the outputs. Many aren't effective users of their monitoring software. I'm not familiar with integrations between code environments and text editors with things like crash reporting (what if you had a hotkey to take your cursor to where the code most recently crashed?).

This isn't deep, crunchy shit; I'm not talking tracking syscalls, or packet sniffing, or CPU cache bust monitoring, or anything else that even requires you to know what an operating system or computer is: I'm talking about help in their own, chosen, higher-level languages. You can also expand the territory to other tools: how many know the keyboard shortcuts and have a process for their email clients? Hell, how organized is your Slack? Your team and company's relationship to issue trackers?

I wonder how much stronger shops would be if they treated their labor like Korean gaming houses. If they had practices and drills like any athletic team. If they had a set of fundamentals to practice like musicians and their scales and arpeggios. I'm not talking leetcode, I think there's way more to explore here.

Artistic/Cultural Path

I might say "fuck it" to computers altogether. I got to computers by saying "fuck it" to theatre. Maybe my strengths are in storytelling and artmaking.

Encodings for artists

I had half a mind to make a "pandoc for music," bringing MusicXML, Lilypond syntax, and ABC into a single intermediate representation (maybe proprietary formats like Sibelius and Finale too), from which you can transpose, re-arrange, publish for print and web, preview listening, apply AI.

Mutopia project seems to have faltered, and they have exactly one (1) score for the accordion. What would it require to make it as impactful as Wikipedia?

How come "generative music" hasn't had as big a splash as "generative pictures"? And in both cases, is it possible to leverage these technologies in a way that the resulting artwork doesn't suck, and it isn't hell for people who produce these things either?

Robotic neurosurgery, sustainable seafood farms, ecoterrorism, hacking local police and sheriff departments from a non-extradition country…

I have other ideas too, but this is long enough.

Well I'm glad you asked, person in Pablo's imagination. Here's some inspirational material I've loved.

• A Whole New World, by Gary Bernhardt. Talk, ~20 minutes, exceptionally tight execution. About a few topics, technical, but also what I'm looking for here regarding visions for a better future.
• Watch a VC use my name to sell a con, by Jamie Zawinski. Blog post, short, I wish everyone spoke this damn clearly about the whole edifice.
• Don't call yourself a programmer, and other career advice by Patrick McKenzie. Blog post, if you want advice to play the game, you can do a lot worse.
• Palo Alto, by Malcolm Harris. Book, quite long, but very worth it. I'm not an audiobook guys, but the audiobook is narrated so well by one of the most intelligent and articulate people I went to college with. One of my favorite books in the last decade.

Wow, you made it this far!

• Send me an email, say hi!
• If you're in SF, let's get coffee! If you're not, tell me where you are and we can chat when I'm there.

Good luck out there.