How did my plague year go?
Oh hey, I’m Matt, and I send these so irregularly you may have forgotten who I am or what this is. This is a strange kind of personal newsletter, with bits about how to build thoughtful products and teams, bits about startups and investing, and bits about art and music. You probably subscribed because you read something I wrote or used something I’ve built, like Beme or Tumblr or a number of other projects.
So, about 2020
My professional bread and butter is building, tweaking, and debugging systems to help groups of people build big creative and technical things together. Working within a company or with a founder, I insist on making space to reflect, honestly dissect, and improve. Feedback loops, retrospectives, 1:1s, goal setting and communication, etc, etc. I genuinely love perfecting these things.
And yet, when I finally made it through last year, my reaction was: Great! Let’s just triple seal the big ol’ Pendaflex of 2020 shut with duct tape and label it “SLOG!” That’s all the reflecting I need on the year of our lord 2020, thank you!
While you do not have to be good, more often than not I find it worth a try. When I jerk so strongly away from a thing I know is valuable, I’ve learned to pay attention. It’s not that doing a review of my year would not be worth it, but it might be really hard.
Then my friend Schlaf went and made things easy: He posted a straightforward template for doing an annual review for yourself.
I dug in. There was indeed some pain. He suggested looking through your digital ephemera for the year, from emails to calendar to photos. The plans to spend the spring months in Mexico City and September learning about homebuilding in Vermont appeared. All dashed, of course. As did the dozens of news headlines I screenshot, all a bit too 28 Days Later / La Jetee for my taste.
There were triumphs, too, though, which I felt compelled to revive this newsletter and share.
One goal that came out crystal clear in that review as well is that I need to share more of my writing. I’ve got tens of thousands of words just hanging around in Ulysses, with more coming each day, and I am being too precious to just share them. 2021 is going to be about not worrying so much about the polish—so if you aren’t up for a rough draft in your inbox every few weeks, opt out now and my feelings will not be hurt.
Anyhow, what did I accomplish in 2020? Well…
Oda launched!

Oda, which I cofounded and have been putting a good chunk of my time into for more than two years, launched.
Do you love music? Do you miss hearing it in person? Do you want a beautiful speaker that looks like no speaker you’ve ever seen? We’ve sold out the first few batches, but you can order for the next batch in time for the spring season.


There are so many stories I’ll share in the future about how this company went from Nick’s touching, wild idea to today, where we of shipping the first units to our paying members. As every founder of a company that involves hardware had warned me, it’s been a harrowing journey.
I got to try the COO seat
Though I’ve led an engineering organization, started a startup studio, been GM of a unit within a big company, and just generally and joyfully sampled many flavors of managing the operation of teams, I’ve never explicitly been a COO. That changed last year, in a trail-by-fire way that I love.
In early spring, conferences and events around the world were being cancelled. Organizers of all sorts were flocking to Hopin, which I had invested in only a few months earlier. Growth was off the charts, faster than anything this soon out of the gates myself or any other investor I spoke with had seen. With an a team of only 25, and a waitlist of thousands of enterprise customers including much of the Fortune 500, the need to scale and level up in absolutely every part of the business was terrifyingly present.
Johnny, the founder and CEO, would call me for advice. At first every couple of weeks, but quickly it accelerated. He said “It’s lockdown. You’re in the mountains doing nothing. Why don’t you try out the COO job for a few months?”


It was an absolute thrill ride—so much so though that I truly agonized over whether I ought to stay on permanently. There’s so much to share of even those few months about hiring an executive team, communicating well, onboarding when 95% of your team has not ever met in person, etc, etc.
I invested in 3 new startups
… none of which are public yet, so I can’t share the names. Ack, sorry.
Three was a lot fewer than I had intended to invest in in 2020. And not for lack of dealflow! There were a ton of companies I saw raising last year. It felt to me and other investors I know who focus on pre-seed and seed like one of the hottest years they’ve ever seen. But with the intense months spent on Hopin, and my own biases against the flavor of company that I saw most this year (MBA-solves-middle-market-problem-with-best-practices, ugh), I didn’t jump at any others.
Hopefully, 2021 will be back on track.
And plenty of other startups in my portfolio managed to have a great year as well
Headway has dramatically expanded the number of customers it helps connect with insurance-covered therapists, and turned to helping its network of mental health providers go virtual on a dime.
Airhouse and Northstar launched the products they’ve quietly been working for several years publicly to strong receptions
Kapwing continues to lead in video editing from the browser, something that also took a leap in Covid.
And Gossamer continues to impress me with their commitment not just to growing their brand and products, but also justice:
I wrote almost all of this earlier this week, and am just now sending it out simply because I was bikeshedding some Substack settings. But I have to include a note about yesterday:
You, like me, might be feeling the strong urge to bury your head back in your work. You might feel the best thing to do is to just focus on building your company and not pay attention to “politics."
If you’re building in America, and even if you’re not, this does affect you. Functioning democracy is the kernel every startup and creative endeavor depends on to run. Bitcoin can't make sure your team goes to bed not fearing for their lives. Google cannot impartially settle a dispute with a vendor. No VC can fund for the kinds of foundational research on which the vaccine to end a global pandemic is based. And the kernel that provides all that functionality is not in great shape today.
Believing you can just go on, because technology is above all this, is living in a fool’s paradise. I’m going to do my best to keep contributing even in some small way to the maintenance of that kernel. Otherwise, the vile mob will be happy to make some hard-to-revert changes.
Ouch, that was such a lengthy update, I’m sorry. I promise this year is about short, sweet, and off-the-cuff with this newsletter. I’m so glad you’re here.