B-Sides From My Twenties is a collection of nine meaningful stories from my twenties, where each track number roughly corresponds to the year in which it happened.
I call these stories my B-sides because I consider the three EPs I released to tell the "A-side" stories that shaped me most during the last decade.
I had originally planned it as a full-length album over the next couple of years, but decided instead to release the tracks one by one as singles for my own sanity. The tracks will come out in whatever order I feel the songs are ready in. Appropriately, what will eventually be track 5 on the album is out just in time for Christmas 2020.
Stream it on Spotify or Apple Music beginning December 14th as a single. Once all the singles are out, I'll collect them into an album and release the album more broadly on more platforms.
This seven-track EP is my most significant work to date. It tells the story of a time that spans 2016 through 2019, and I couldn't be more excited to share it with you!
It was written and produced over a period of eight months from July 2019 to February 2020, largely during 40-minute walks (and for this reason, you will find that taking the album for a walk is an ideal way to experience it).
Jason Boshoff is the mixing and mastering engineer on this album, and has really elevated it beyond even my most blue-sky expectations.
A period of inactivity in my personal projects as all of my efforts have gone into building CollegeVine during these three long years. Although the timeline starts earlier than 2016 and continues to today, the three years between 2016 and 2018 formed the most intensive incubation period in this journey.
There's a rule I read somewhere before embarking on this whole thing that said, "it always takes about three years to become a competent startup founder; this rule applies even if you know about this rule." It's true.
Being a first-time startup founder and CTO is the hardest thing I've ever done. There is nothing framable for this transformative journey that I can hang on a wall, so this logo and everything it represents will have to do.
This five-track EP represents 15 months of unrelenting dedication and hard work to prove a single conviction: I can get better.
This album tells a story that spans November 2013 through October 2014. It was written and recorded in my home studio in Portland, OR; I am the recording and mix "engineer," and it was mastered at Vita Mastering by Chris Vita. The album art is my own.
In order to record and produce the EP, I converted a bedroom in my house into a home studio. The deep work aspects were in researching acoustics and studio design and coming up with a floor plan and interior configuration that satisfied a bunch of constraints (I started knowing almost nothing).
After I had the plan, it was then a couple of months of sourcing materials and actually doing the buildout. The space is constantly evolving as my own music production practice evolves. Here it is when it was first constructed (the last photo is what it looks like more recently):
In 2014 I experimented with custom-printed t-shirts. I had these printed at Big Frog in Portland, OR on various J.Crew t-shirts I'd find on sale. I used Adobe Illustrator for all of these (as you can tell, I'm decidedly a vector, not raster, artist).
I raised chickens with the express purpose of learning the true cost of eating eggs and meat and to recondition the soil in my yard using the concept of a closed(-ish) ecological loop. Raising chickens is not really deep work, but going zero-to-one in building reliable exterior wooden structures and designing chicken coops definitely was. I chose to design my own instead of buying a plan because when you're 26, you tend to enjoy reinventing the wheel for the sake of it. I also learned how to use a lot of woodworking tools for the first time.
There were a few lessons learned from this experience, all of which I wrote about in a blog post from around the time I completed the project.
I traveled around the world in 2013 working as a migrant farmhand—fueled by youthful passion and a bad breakup. Predictably, I did what every boy scarred by his tragic high school battle of the bands audition would do: try to record an album to set things right.
Well, that's certainly an "A" for an inspiring origin story, but the end result was pretty raw. What was special about this effort is that I gave myself 60 days to go from zero-to-one. I wrote about that experience extensively in a series of blog posts, now reproduced on this website.
You can also find the lyrics here.
The album above features an upgraded agave blue Fender Stratocaster (Made in Mexico) that I received for Christmas my senior year of high school. I had never taken the time (nor had the bravery) to understand how an electric guitar works, but decided that I could not record it in its original form, so I learned how to wire and properly set up a guitar from scratch and did so.
It turned out to be fairly straightforward and has been documented in an old blog post.
While traveling, I wrote a series of inspired long-form emails to about 50 friends and family who signed up to receive updates from me during my trip around the world. I spent at least 10-20 hours on each writeup, focusing on storytelling and touches of photojournalism. My first letter is reproduced here.
For a good portion of this year, I dedicated my life to trying to land the freestyle windsurfing move known as "The Vulcan." And I did.
Unfortunately, I only landed it a handful of times before I moved away from Austin (and beautiful Lake Travis). And being that windsurfing happens on the water, the wind changes directions, and I can only do it on one side, there were very few opportunities to get it on film.
All I have is a grainy video of a botched attempt about two months before I landed it for the first time. You can see a lot of the elements of the move coming together, but I still hadn't figured out how to lean on the nose and sail very hard after the 180, which is the key to landing the move.
I spent a ton of time blogging during this year. It's always hard to read your younger, way longwinded self, but I've collected a bunch of posts spanning BJJ, windsurfing, health, and leaving Austin and assembled them here. I blogged a lot in 2012 and, in retrospect, see that year as a lynchpin in the development of the writing voice that I now identify with.
Unlike in 2012—the year I went to town on writing blog posts—2011 in contrast resulted in only a few selected posts and essays about the Paleo diet and windsurfing, my two chief pursuits at the time. I think this was also the year I had the most friends in my life, so I was likely fairly social as well, which led to less time for deep work. And that's not a bad thing, mind you.
I don't remember exactly when I did these, but it must have been sometime while I was living in Austin, TX (however, the flowerscape seems to be dated to 2012, but I'll include it here anyway). I'll use 2011 as an attribution midpoint.
Similar to 2012 and 2011, 2010 resulted in a collection of posts about the Paleo diet, primal lifestyle, and windsurfing, my chief pursuits at the time.
A failed attempt at a personal website builder (i.e. a lame version of Squarespace, Weebly, Wix, et al. before they became mainstream). Incidentally, many of these companies were started around 2010, so I'm not surprised I also had this idea around the same time.
I ended up building a few reusable personal website components and tried to genericize the idea of a personal website.
I built a few websites for friends and acquaintances during this time, but I had not yet learned the distinction between selling a service and a product. I think this was the point at which I gave up on startups for half a decade because they were "too hard." I found a couple of old blog posts about it.
My first car was a Saab 9-3 and I was very sad that it didn't have an aux-in jack (the 2000s, amirite?) With a lot of help from a friend, I hacked this thing into the car. This was my first taste of DIY success and was a formative experience in me feeling like I could pull things apart and reasonably be able to put them back together again. This experience is memorialized in an old blog post.
Before MonogramX, I also built this thing called AccomplishBoard to scratch my own itch, but it was basically personal kanban before I knew those words. I got no signups, but got pretty good at MVPing products (in the product delivery sense—had no idea product discovery was a thing at the time).
These were my college years. I did a lot and slept very little. Who knows how many memories I no longer have? Sometimes I find an artifact and suddenly remember: "oh yeah, I did spend a lot of time on that..."
Still, everyone does some form of deep work in college, so I'll speed through this stuff.
Following the time-honored linguistics tradition of trying to be punny in your paper's title, I came up with "Potentially Useful, Momentously Difficult: Inferring the Temporal Dimension of Sentence Comprehension Difficulty with Potential Functions and Second Order Measurements."
Read it here.
I found these in a folder from an old version of this website. I have not read them, and you probably wouldn't want to waste your time doing so either. Unless, that is, you are in college reading this and curious about how your own writing stacks up. These papers were brought to you by SoBe No Fear or and/or Red Bull. Never again, however.
I built and ran our fraternity website. I think there's now a SaaS solution that lets you run your entire organization, but this was like 2007, ok? We sent lots of inappropriate emails through listserv and thought we were baller. I did two versions over the years.
I guess this is where the startup bug got planted. A friend with a lot more vision than I at the time had the idea for Facebook Groups before it was a thing.
It ended up not going anywhere, but I ended up building it out and using it with a group of high school friends to stay in touch. I think we ended up using for two, if not three years. Lots of fond memories from that time.
While in school, my personal website underwent several revisions, captured here:
There's not a lot that I'm proud of as far as CS projects go, but a couple come to mind. I can't find most of them right now (probably on some old drive somewhere), but at least one was memorialized on the Internet.
These were my high school and childhood years. I made a lot of stuff that mostly wasn't very good, but in retrospect, these were the seeds being planted that I'm harvesting now on the regular.
I painted a lot when I was in high school. I volunteered at the local YMCA helping to teach a class there. The medium is acrylics on watercolor paper. The dolphins are acrylics on canvas.
I used Cakewalk, FruityLoops, and Acid back in the day to produce songs off of samples. I had no idea what I was doing, but those experiences formed the basic mental models for DAW usage, which would of course come in handy later on. I'm fairly certain I have the project files somewhere, but perhaps not the mixdowns. If I find them at some point, I'll post them here (note: project for future self).
I started a website when I was 11 called FFCards.com. I knew HTML and some Visual Basic, but very little about hosting, CSS, software projects, community-building, serving ad banners, video game reviewing and documentation efforts, but somehow managed to do all of that for a few years without anyone noticing that I was a prepubescent boy. One day, a well-respected 18-year-old community member called me out for being immature and I said, "well, I'm only 13!!" and you could hear a pin drop on the FFCards.com forums. I couldn't be 100% sure it wasn't my 56k dial-up connection cutting out again, but the odds were overwhelmingly in favor of the community high-tailing it out of there ASAP. Good times.