This post was inspired by something I did many years ago - Stuff I Said In 2015

If you are receiving this by email, I honestly have no idea how these embedded tweets are going to render in your inbox, so you might be better off reading it on my site in the browser here.

Twitter is a lot of different things to me. One is that is serves as a sort of diary– a stream of consciousness. Here's looking back at a chronology of my tweets from this year, each with a little commentary that will give you (and me!) a clue as to where my head was at throughout 2021.

I'm going to be doing a lot more with Hypothetically Great in 2022, so stay tuned.

Wishing you a happy and safe new year. 🥳

– PC


The first tweet of 2021 was me doing some amateur epidemiology math. Seems right.

Within the first week of this year, January 6th happened. I was watching the livestream of the certification process at my desk, and I remember seeing the feed cut to the lobby just inside of the front doors. And people were just waltzing in, holding their flags, looking around, taking pictures, yelling– I remember Slacking people like, um, what is happening.

Trump's speech to the nation. Yikes.

When Trump got booted from the internet.

Boom! What a time to start a tech podcast. We kicked it off with an episode all about censorship on the internet and groups of strangers coordinating to take action in real life– what would become perhaps the defining theme of 2021!

This was r/wallstreetbets and the debacle of Gamestop. This was all before the end of January!


End of an era. (to take effect in the summer)

If there was one album that defined 2021 for me it was Medicine at Midnight by Foo Fighters. (Although Donda and Olivia Rodrigo's Sour are really close seconds)


Thinking A LOT about this still months later as I contemplate my next moves...

Foreshadowing of a lotta meta stuff this year.

NFTs as a concept entered my brain in mid-Feb, but what they described lined up nicely with a lot of the themes I'd been exploring for years around AR and virtual objects. 2021 brought NFTs into the public discourse, but it's still early early days.


I was still very much teaching over Zoom through the summer.

Calling my shot. In the end we don't have smart glasses or contacts, we just hack directly into the optical nerves (or perhaps downstream from there) and let our brains do the rendering.

This was after Slack add the ability to DM people from other orgs– now a widely used and key feature. People initially were complaining that they might get unsolicited messages, on the internet!! 🙃

Bounce House launch party in the right frame. Old age or Covid? Let's say Covid.


Just had to highlight this because I got to meet Robert Smith, poss highlight of 2021.

Proud dad.

IMO, tracking is any sort of data collection about your users. Every single one of my businesses has tracked an insane amount of data, attributable at the individual user level + in the aggregate, used for understanding how our products got used, conversion rates, etc. And never used for advertising. Targeted ads ≠ data tracking. I still am confounded at how these are use synonymously.


To be fair,  I wouldn't rule out Snap, but if I had to pick the two contenders for top dog at the device level of our metaverse future, it would be Apple (incumbent) vs. Meta (né Facebook, new entrant). It is hard to evaluate where they are today since Meta is building in the open and Apple behind closed doors, but it's clear that they see each other as direct competitors in the future tense. I would place my bets on Apple, but I am keenly aware of the common fallacy of assuming that leaders will stay leaders.

Had an episode about this: Apple and Facebook battle for the future

AirPods Pro were quietly a revolutionary device that have impacted my thinking on AR generally.

I found this rifling through old Dropbox folders, and I was struck by simplicity of the value proposition. This was long before I had any mental frameworks for marketing or taught any business school classes– this was just instinctual as we looked to package what we were doing to prospective customers and investors. I want to always strive for this sort of clarity in my messaging.

You don't want to see my GoDaddy account.


Not a joke, this is actually a winning formula that I use over and over again.


What Apple is doing is almost authoritarian, but maybe in the good way? (Someone please take this quote out of context and cancel me.) They are fear mongering about online privacy, and then providing safe solutions for everything you are worried about: identity, finance, communication, and so on. In doing so, you are in fact conceding everything you hold dear to a corporation– the exact thing they warn you against doing. But because they are the good guys, it's ok in this case to surrender and do it. And you know what, as a consumer, I'm in! I want someone to deal with all that scary stuff for me, and I trust Apple to not screw me. It is absolutely in their best interest to convince me of this, but that doesn't mean it's not true.

This was right in the thick of getting the MAZ and Bounce House deals done. Right now I manage zero people, and I honestly do not miss having to annoy people. But I do miss having people to annoy.

June was when I got into DeFi, like actually personally started messing around with it. It was only then, when I started doing stuff firsthand, that I started to understand anything about web3. Dealing with wallets, bridging across networks, staking, yield farms, liquidity pools, rug pulls– I'd read a lot about it, but that is really not the same as experiencing it. My immediate reaction was like, wow, this is a fucking mess. The implications of the tech are so powerful and strange, almost alien, and yet it's paired with such cumbersome and obtuse UX/UI. So much room for improvement there.

It's hard to put into words what I experienced on this night. This was post-vaccine, pre-Delta. Foo Fighters @ MSG for the first full capacity event there since Covid. It was freaking insane.

First off, some background:
• The Foo Fighters had their 25th anniversary in 2020 and were supposed to tour.
• Their album also was supposed to have been released in 2020. Instead, they released it January 2021.
• They announced this show just a couple of days beforehand– their first show since the pandemic.
• For me personally, the Foo Fighters is one of the most meaningful bands of my childhood, early adulthood, and beyond. I know every single song on their 10 albums.

I was very hesitant about going. Especially when we got inside, in a flood of people, all maskless... I continued to wear my mask. But somewhere around the second song I ripped it off and just went for it. And the whole arena just screamed at the top of our lungs for hours on end. It was cathartic, beautiful, and honestly the only word that does the experience justice is spiritual.

We need to be in the presence of other people. We need shared experience. We need to rock out without fear. I forgot about everything else that night and the pandemic just washed away. I wish everything could ever be that good forever.

I have a draft of a post about this still kicking around, but a lot of things we were working on a long time ago have finally found their way into iOS. It's not that we were visionary geniuses, it's more that certain things really are meant to be features in the end, not whole companies. And for Apple to add a feature means that it must benefit billions of people, so the threshold is quite high. That means there will always be long gaps, years long, where some number of people want something that is too small for Apple to care about yet, and too small for it to be worth building a viable alternative, and so that market will just remain underserved, and there's not much to do about it.


We sold the company 46 days later.


Life advice.

I absolutely loved office life, and this was a perfectly fitting end.

I am getting a new office in 2022. I need it.

My first mention of metaverse. Don't remember what happened in early August, but I guess that's when we started calling stuff the metaverse. Less than 3 months later, Facebook changed its name to Meta.

Still think about this a ton, but as soon as I first learned about NFTs (February-ish) I can't stop thinking about personal identity. ENS is working on web3 identity stuff, and I do think verifiable identity in the metaverse is going to be essential. Perhaps whatever we come up with will be so good we might end up using it IRL too...

It is truly incredible to me that I can come up with a framework, based on my own experience building products/companies and observing many others, formalize it and give it a name, teach it, and then have my students go on to use it in their work. And then slowly realizing that everything I've ever learned is just someone's else's this. It's bizarre and humbling and empowering.

The day we closed on the sale of Bounce House.


The day we closed on the sale of MAZ.

This was the day the MAZ deal closed, and it's actually a crazy story. I love Ghostbusters– all time favorite movie, and the truest keystone of my childhood. In December 2020, I decided that I was going to order myself these four collectible "figurines". Basically they are grownup action figures, running at $100 a pop. But I was like fuck it, I deserve to do something nice for myself for once! I was going to set them up on my desk at work. I ordered them and told Jess that the girls should give it to me as a gift for the holidays.

They never came. It said they were shipped to my office, but they never arrived. I contacted UPS, the company that sold them, the credit card company, back and forth until I eventually got fatigued and just gave up. Money down the drain. No toys. I learned my lesson: never try to do anything fun for yourself!

Skip ahead to August 2021, I am no longer in the office because we had found a new tenant to take over the lease in anticipation of selling the company. I had taken out a hefty amount of cash to tip our longtime doorman John at the building before leaving, but he wasn't there on our last day so I took the envelope of money home. I had walked by a couple of times since then trying to catch him, but he was never there. Now, it's the day of closing, August 31. We closed in the morning, had a nice celebratory lunch with the extended family, and that afternoon I walked to Flatiron to see if I could catch John to tell him the news and give him this envelope of cash that's been burning a hole in my pocket.

He was there! We exchanged a nice conversation– it was bittersweet because he was there through the whole pandemic. For months we were basically the only other person outside our families that either of us saw in a given day. We had a good run. I give him the envelope, and I'm turning to leave, when he says, "Wait! There's a package that came for you." It had come the day before, and he was worried I would never have gotten it since he didn't know how to reach me. I am trying to imagine what could be in this box, maybe some random thing from Amazon that I had ordered weeks back and forgotten about? I take the box and start walking home.

At the corner waiting for the light, I cut the tape open with my keys and glance inside. I see a Ghostbusters logo. I'm like, no... way... and sure enough, it's the freaking Ghostbusters action figures, all four of them.

And no, the box hasn't been sitting there since last December, it's postmarked just a few days beforehand. I hadn't contacted the company in at least 8 months. What? How?

We met some friends for drinks before going home, and I gave the box to Jess and told her that the girls can give it to me as a celebration present when we get home. They do, and I'm thrilled. We played Ghostbusters on the floor, and I teach them all their names, about PKE meters, ghost traps– a perfect ending to a day 11 years in the making.


20 years.

I actually wrote this in fall 2020, but I continue to think about it. It's perhaps the best thing I've written in the last 2 years. The future of photos isn’t cameras

Announcing this was such a surreal experience. For most of the year (since March/April), I'd been working on this deal but couldn't tell a soul. Not to mention the decade of grinding before that. It was like screaming from the rooftops, "We did it!!"

No, I don't remember what I did the third day.


This was the first time I ran this and it was awesome to watch– I gave each student a role to play by slipping them a piece of paper with their job title + some things to say, and then just let them play it out, each approaching the product manager with their issues. The lesson: it's a hard job.

Similarly to the Foo Fighters show, the energy in the room was electric. There was more fear and anxiety for sure (boooo Delta) but it was still elating.

After about a month of trying not to do anything that resembled work, I started to realize that I actually like getting shit done.

Not only was Seyi a great guest lecturer, but for the first time in my teaching career, a group of students stayed after class to informally continue the conversation and it was so freaking fun.



Longtime policy.

I wrote more about this here: Some brutal numbers from Facebook's outage

In my previous life, I would rush to campus straight out of a series of meetings, running into the classroom at the last minute. But this fall, when the weather was nice (and even not so nice), I got to campus 4-5 hours early and would set up shop outside, inviting students to come chat. Professorial life is pretty fun.

I get a PCR test 1-2 times a week, I honestly love it.

This was an amazing 3 days of reconnecting not only with playing various instruments and singing, but also with the process of producing/arranging/recording which I'd really missed. I love being completely immersed in that process– which has parallels to working on software, except that the result is instantaneous! You lay down that next track, and then you can you play it right back! With design, I will have a major breakthrough, but I still have to wait days or weeks to see it in action.

I don't think I'll go back to music full time or in a serious way, but it was fun to rediscover it, and I hope I can find a way for it to fit into my life going forward.

Also, Ben Folds was truly a childhood hero of mine (literally wrote "Ben Folds" at the top of my school worksheets instead of my actual name) so working with him was pretty surreal. 🤩

I cannot say this enough times over and over: smart glasses will replace smartphones.

This fall going back on campus after a year and a half remote was honestly just so fun. I fear spring semester will be much more Zoom-y...

I must have been writing this at a time: The last screen you'll ever need

I enjoyed the Meta presentation but it was all rather... stationary.

In all cases, we are moving from rectangular screens to full field of vision computing. Sitting your desk doing work, it makes sense to be immersed (VR), but when you are on the go, or even on your couch, you want to be aware of the real world (AR). Same use cases as computers vs. phones.


Maybe the podcast episode that stuck with me the most from this whole year. 9 minutes long– worth a listen.

I'm dabbling here and learning as much as I can about the investment side of the biz. The most attractive part is working with and thinking about lots of different types of companies, whereas when you do your own startup, you just think about one company all day every day!

Found this photo from 2017 where I attempted to walk around the city (and order a coffee) while wearing a VR camera. This is the future I want to have, and I've been thinking about it for a long time.

Wrote about it here Facebook bought Oculus, now Oculus owns Facebook but basically I realized that Oculus is now the parent company (and renamed to Meta).

He had tweeted a warning not to "befriend wokes" and I said it was "cringe"– annnnd, blocked. 🤷🏻‍♂️  Kind of a badge of honor, but overall I actually liked what he has to say about web3 so it's too bad.

I believe strongly that choosing to not befriend (or to block for that matter) people with differing opinions is not the right way toward a productive society or toward growing as an individual!

That same 50 ENS peaked at around $4,000– which I was given as a gift, for free. Wrote about it here How I made $10,000 out of thin air a.k.a. incentives in web3

Oh man this was such a crazy couple of weeks in web3 world. Did a whole episode on ConstitutionDAO here Buying the US Constitution with crypto

My first and only flights of the pandemic were to visit my best friend and long time collaborator Simon Baumer in CA. Sitting in that chair in the sky was the most productive few hours I had the entire year.

CA > NY. Not sorry.

It hadn't even been 3 months since the MAZ deal closed but somehow felt like an eternity. But we finally got to celebrate together and hang.

This looks like someone Photoshopped it but it was very very real.


I am trying to think a lot about what is the equivalent of this beer app right now. When I saw that, I realized the power of the tech, and that one day soon we'd all be using our phones as fully fledged computers.

This was right before the Omicron panic– an annual breakfast held by Rene Plessner, a friend and one of my earliest angel investors. He has kept in such good touch with his network over many decades, and invites them all to a fancy party every year. I love it and after skipping 2020, we all were like, we just have to do it.


I still sort of disagree but the crowd has spoken.

It's only real once you have a hat!


Just recording this episode was really a trip– a whole lot happened this year.

ENS is more than the GoDaddy of web3. It's almost more like the DMV.

Been thinking a lot about what it really takes for a product to be fully viable.

🙏  Let there be peace on Earth.