🎵 The song for this post is Dreams Go By, by Harry Chapin. My dad and I disagreed in high school on whether this is a happy song or a sad one 😛 🎵
Since 2016, I've made it a thing to write "year in review" posts. I found this one especially hard. I struggled to understand 2021 in any other terms than being a long, torturous road to a breakup; the biggest and worst one I've had, for the longest relationship. A year of no permanent housing, fighting like hell and contorting my whole life to make a relationship work with someone who didn't do the same, only to watch it fail (and to be the one who had to pull the plug myself). I gave everything I could, I wanted nothing more, and it didn't affect the outcome. We spent New Years Eve in separate, underfurnished domiciles.
(photos redacted at her request)
It felt impossible to manage all the things I wanted to balance: being honest with the reader, being sensitive to my ex and the fact that we have mutual friends, to present here like a mature, cool, collected person. It was hard to communicate anything, factually or emotionally, without airing dirty laundry, which I didn't want.
Okay, correction, I desperately wanted to air dirty laundry, because I love juicy narratives, and I felt fucking wronged. More accurate to say "I didn't want the social ramifications + chaos + inevitable, mutually assured destruction that would've come with airing the dirty laundry." I always understood, in my head if not my heart, that it'd be a terrible idea that wasn't worth it. Head-not-heart always understood that I might cool off on some of this as time went on, and/or as I build a new future instead of the one I dreamt of, and thought I had a partner in building.
I have cooled off! A bit, anyway. I'm finishing this post from New York, where I just spent a pretty magical week. I'm so grateful for best friends, good weather, and new energies. Many things became clear to me, other things got confusing, and while I've still got plenty of feelings, the worst ones aren't present as they were. Having a tiger in front of you is scary; it's still scary but a critically different scary if it's also behind a plate of glass, and you're at the zoo.
On heartbreak: it's a lot of yelling at an invisible referee and begging them to make a different call. You fixate on pointless hypotheticals, you watch yourself spin endlessly, and you're powerless to stop. You pour another drink. It's as mystifying as waking up one day and the whole world assures you there isn't and never has been a letter "g." You don't have a frame for how hard your reality can break. You can't understand how prevalent the artifacts of that partnered life were. Not even physical artifacts: I saw things like Amado, or the serendipity of my mom's maiden name Castillo ("castle" in Spanish) and her surname ("little castle" in Italian), or photos of us on trips and I just struggled to feel like I was still on any Earth that would have a sunrise the next day. I told myself it would, I didn't believe myself, it always did. You visualize your kids. You imagine their laughter. Their little hands squeezing your big hands. Looking in her aging eyes and feeling blessed that this is happening; you'll both age, together. Then… you remember it's not. Because you made that future scary enough for her to burn it down instead.
I was pretty spun out. I wrote most of that ☝️ in January/February, for what it's worth. So this post is a bit late.
I'll end this section with a little anecdote: I got a Pixel Stand in June, which sits on my desk, charges my phone, and shows me photos from my life while I work. I mused that it's like a "reverse Instagram effect:" I look at photos and think "wow, that guy's life is awesome! Look at all the cool shit he's done!" It showed photos of various trips, vacations, and festivals I'd been to. It showed slice-of-life dinner shots, or things like posing in front of that goofy window display you walked by. Karen was in nearly all of them, since we were partners for 5 years and did most things together.
It got too hard to bear during the separation, and because Google Photos doesn't have a "breakup mode," I had to archive all our photos together to not be blasted while I'm trying to rebuild. It's now showing me photos from, like, 2012. I'm seeing other exes from over a decade ago in my photos. Sapo (my dog) features prominently. I'm seeing myself in places where I know Karen is just out of frame.
So now I've got the habit, wherever I am, of saying "I'm forming new memories!" and aggressively demanding selfies with whoever I'm with. I need new photos!
In a similar way: I'll never truly believe last year was substantively about anything other than this heartbreak. But I won't heal if I actually give it total dominion of the narrative. So this ☝️ is all I'm going to write about it in this post, and now write about the other narratives of the year. You can mope at setbacks, that's just natural. But at some point, you gotta pick up.
Moved to SF
The biggest change was Karen and I moving to San Francisco. I'll take this opportunity to elaborate on how we ended up doing that, and what my housing situation was last year. Most people only got bits and pieces 😛
Two years before, we had what we called "the triple coincidence:" my Lyft cliff was hitting, her previous role was winding down, and our lease was up. We thought about making a huge life change and leaving NY. We called it "Project Madagascar" ("hell, we could go to Madagascar!").
Karen: "There's one place I'd really like to go"
Pablo: "There's only one place on Earth I refuse to go."
Both: "San Francisco!"
I was like "we could go anywhere! Florence! Sydney! Buenos Aires! Whyyyy the sleepy techbro hub I escaped a decade ago?! The only shittier rent market in the country but with a Diet RC Cola version of a city attached?!" The answer was community: Karen wanted to live near the social scene of our Burning Man camps, as well as finally leave NY (she'd spent her entire adult life there, and every time she'd wanted to leave, it was blocked by a romantic partner). I relented: "if you want me to, I'll go. I couldn't bear to get in the way of your dreams. I can adapt there. I always do." She also relented: "I care about us, and I couldn't enjoy being there if you grew resentment over it."
It took a lot of digging into vulnerability to articulate to her why I was actually most worried. I told her: I was convinced she would find me unstimulating, and drop me and our relationship to "join the circus." Never believe anyone who tells you prophecy is a gift. Subsequent digging also revealed that she had fears about leaving NY, a city she knew very deeply and had her networks in.
So at that point, we chose NY. We signed docs committing us to residence in NY, and tried to host regular events for friends at our place, at least for a while.
The pandemic hit shortly after, and after so much time cooped up, we did a road trip where we visited a ton of cities. We stayed in SF and podded with a group of friends I'd always advocated getting closer to: I felt a lot more value alignment with them than most of the Burning Man folks we knew. Two weeks became three weeks, and it was sad to leave. I still didn't yearn for SF, it felt possible. There was a real thread of us both finding new ways to thrive.
We moved into an illegal warehouse with a bunch of artists in April. There was a ton to love about it (they were fantastic housemates; just big-hearted, talented, generous people) but the "illegal" and "warehouse" part of it introduced a lot of challenges for us, mostly me. It turns out there are advantages in living in spaces designed for humans to live in!
The group house we stayed in previously had an opening in August. I took the room. We lived with amazing friends but issues around my relationship with Karen (and there being too little space for the people living there) put a few of us in a game of Housing Chicken. I "broke" first: while many were enduring a lot of pain, and everyone recognized there wasn't a clear road to improvement, I was the one to eventually say "something here needs to change," and got a 1BR of my own in November. Seinfeld "yadda yadda yadda," Karen and I broke up a few weeks later.
Nobody, including me, wanted to leave the Cool Friend House, and losing it (and the ability to painlessly visit after the breakup) was one of the more painful parts of the aftermath. But! My current apartment rules. I've had a ton of fun decorating and automating it. That'll be its own blog post!
So now I'm in SF, with a lease until November. SF is a lot better the second time around. The breakup rattled our social group(s) pretty hard, but I've still got amazing friends there, and discover new things on the regular. I'm very heavily weighing NY after this two week trip (or to Mexico City, or Madrid…) but there are much worse fates than staying in SF for a good time yet.
Ramp Ramp Ramp 💳
Another year at Ramp! Last year I wrote
Ramp has been my favorite gig of my career, and I've had a few. I'm very lucky to have gotten in when I did, and I'm delighted looking at the other faces in my video calls because I've never felt so aligned and supported with such strong players on work I believe in. We've got a ton of work to do and are still comparably early in our journey, but I'm still incredibly proud of where we are, and see no reason we can't reach our ambitions.
And after hundreds of words of broken futures and a disoreinted present, I'm fucking delighted to say, with absolute certainty, that this is all still true. It's very conceivable that sometime in the next 100 years, someone will unseat Amex and Bill.com and Expensify and every other incumbant player; whoever that someone is, they would have started, like we did, in founder living rooms with a team in the single digits. There's still no reason it can't be us.
A slide transition I made for an internal All-Hands, demonstrating that Ramp and Stripe were obviously fated to be together (Stripe was an early investor, and moving us to Stripe Issuing has been a huge part of my last year).
Ramp is now the longest gig of my career, and the longest I've been managing. Some things get better with time. Goals for this year are to leverage my strengths and previous experiences to get us to mid-size responsibly. There are lots of ways for young companies to flare out, fail to get PMF, or die. We're past the "infant mortality" stage: with our runway, existing product, and customers, we're likely to exist for a fair bit longer, but mid-size is where you can stall. Where you can lose sight of delivering value. Where employees can feel incentivized to improve their careers rather than what the customers require. When we started, I woke up every day wondering how we can build up to the world's best corporate card. The day-to-day looks different (and we're beyond cards) but every day is still day 1.
Here's to more 🥂
Living Room Play Readings 🎭
When writing about Barry, I said:
I miss theater. And I miss loving it, knowing I was good at it, feeling committed to a purpose that way. Feeling like I was surrounded by peers and we'd make a dent in the world with it. I'm unclear if the soil of my life after my early 20's has produced a beanstalk that climbed that high; I think I'm good enough at computers, but I haven't located the feeling of greater purpose of community, just really fun ways of thinking.
One way (with a little help from my friends!) that I've made myself happier is hosting and curating a series of live play readings. It's pretty simple: I acquire 3-4 copies of a favorite script, put out some cheese, and we read the plays cold, in real-time. Most people are discovering the works for the first time.
It's a safe, low-key, supportive environment for people to get to do some dramatic reading. After seeing a ton of shows in 2015, "I've kissed a lot of frogs," so all but one were a selection from one of my absolute favorites. My selections have been:
- Arcadia, by Tom Stoppard (I directed this in high school, it was one of my co-organizer's favorite plays).
- References to Salvador Dalí Make Me Hot, by José Rivera. Just an absolute banger of a play, hits differently after I've been in relationships with their flame waning.
- Jump, by Charly Evon Simpson. Charly is just one of the best playwrights of this generation and this was easily-acquired by DPS. One of the last plays I saw before lockdown, it left me reeling.
- The Shape of Things, by Neil Labute. I saw this in HS and while most Labute is pretty aughts-stale, this one still punches.
- Equivocation, by Bill Cain. Knowing my audience, picked a more "heady with signifiers of high culture" that I remember from seeing a staging of in my college years. It's cute.
- Singles in Agriculture, by Abby Rosebrock. This show rocks, just the playwright being brilliant, hilarious, and heartfelt, with impeccable pacing.
- Kentucky, by Leah Nanako Winkler. The first real "prince" from my 2015 barrage, a hell of an ensemble piece that uses the medium to take you on a romp.
- Dido of Idaho, by Abby Rosebrock. EST's production is very likely my favorite show I've seen in the last decade. Real "run, don't walk" shit, I inconvenienced Karen really hard to show it to her closing weekend.
- Five Times In One Night, by Chiara Atik. We had 10 people who wanted to read at one event, so having 5 one-acts was perfect. Probably the best party trick, these are at turns witty, clever, heartfelt, tender, and the welcome kind of horny.
- Hot'n'Throbbing, by Paula Vogel. We put this on at Brown and I left indentations in the arm rests. Not a light play, but extremely fucking chewy.
- God Said This, by Leah Nanako Winkler. Lord, I sobbed re-reading this. Part of that is what hospital imagery does to me specifically, but it's a hell of a follow-up to Kentucky, both in the character journeys, and playwright's choices in construction.
If we're in the same city, nothing would make me happier if you ask to read plays with me. I'm doing re-reads of these with people who missed the first ones and I'd love to do one with you.
Also, please send me recs! Or your plays!!
I did a homebrew D&D campaign called No, Your Cabbages with a few friends that lasted about 12 sessions. Homebrew is hard! But I had such a good time doing it. I'm pretty proud of the stakes I was able to introduce, some puzzles I designed (I did all the puzzles for a friend's birthday party, a few came from this campaign). It didn't live long enough to hit the plot points I was really gunning for. But I'm proud of what I produced 😊
After our SF house's D&D campaign concluded, I offered to DM a pre-fab game. I bought Curse of Strahd and ran it until the housing/relationship drama broke the game up, also about 10-12 sessions. I also ran a one-shot from Candlekeep Mysteries (I ran The Price of Beauty, a bit of a gift to Karen, since it's a nod to her, as she runs a beauty company), and one-shots of Blades in the Dark and Mouse Guard for another friend's monthly "let's try a new game system with a one-shot!" event.
Friends, I'm a fantastic fucking DM. It plays to my strengths. Watching players react to my work is some of the most meaningful interactions I've had all year. It's a lot of legwork and organization (and again, a lot of my SF-local social dynamics are precarious) but I hope I get to do this again.
Another Advent of Code language-go-round
In 2016, I did Advent of Code with a different language every day. I didn't plan on doing that initially (I'd never done AoC before), but the first few days I thought the problems were simple enough that I could use them to do weird shit, and I just kept it going.
Last year, while traveling across the US, I just picked and stuck with OCaml and finished it.
This year, desperate for a win of some kind, I tried the "new language every day" schtick again. I got about as far as last time. Karen and I broke up, the later problems got hard, and I didn't have the strength to finish. I got to play with some new languages! And it feels really, really nice writing some old favorites. Some entries (like Raku or Scala) are cop-outs. But I'm proud of how I did 🙂
Photos grab bag
Thanks for the read! Disagreed? Violent agreement!? Feel free to drop me a line at , or leave a comment below! I'd love to hear from you 😄