The Limits of Positive Returns

The last real album — at least by the standards I’ve given myself over the years, which are lower than Beyonce, but a lot higher than the average garage idiot — I’ve worked on came out five years ago, in 2014. That’s a really long time for me, but it’s not a coincidence that my daughter was born in early 2016, and my son in the middle of 2017. It’s not to say that I had kids and gave up on music, because I didn’t. My daughter even got to see me play on stage once! But, unsurprisingly, most of the time I’ve needed to be even a replacement-level parent has come from my favorite hobbies, which are writing/playing music and basketball.

Again, that’s pretty normal. But what’s interesting (and what I want to write about) is that there hasn’t been a linear relationship between the amount of free time I’ve had and the amount of production I get from my hobbies. Instead, there’s obviously some amount of critical mass involved, because with 30% as much time, I’m basically getting 5% of the output.

How I Used to Work

To have appropriate perspective, it’s important to realize that my music has historically come as a response to boredom. While I originally learned to play the saxophone as a kid because I actively enjoyed it, I didn’t really write or produce anything until I was a typical suburban teenager with long, directionless summer days and nights (and chemistry class). And even then, I didn’t start getting truly creative until college, when I had literally nothing to do on my weekends and would just drag a guitar and a cassette four-track to our music building and play and sing until my voice was gone.

I can’t understate the nature of how little I needed to be anywhere else during that process. Exactly zero people were ever looking for me, interested in at all in what I was doing with my time, or curious if I was being productive with it. Many times I would strike out, recording hundreds of awful, unusable, embarrassing demo ideas I never played for anybody or ever listened to again, and that never mattered. It certainly had no impact on my willingness or ability to continue plugging away the following weekend, or the weekend after that. In the aggregate, I don’t remember all the terrible things I made that didn’t work — I remember the overall process that gave me the demos that turned into songs I loved that we later recorded in the studio. The ratio of good to bad output was and is irrelevant.

Once I was out of school (and not even writing for a band), this was still the way I worked. I had two small bouts of unemployment that totaled less than a year (maybe six months right out of school, and then another six when I first moved to Cleveland in ’06), and I used the time in the exact same way. Set up shop, start grinding, and stop when you can’t go anymore. I got similar results; mostly crap demos I’m embarrassed by, and a few things I love that my kids still listen to today and dance to in the living room. The process worked.

Time and Capital

In theory, I think venture capital is supposed to work the same way. You try to buy time to give the right people and ideas sufficient room to just keep going to work every day, knowing that a lot of things won’t pan out, but the great ideas that do will be worth the overall process. But I’ve been dealing with venture capital for basically a decade now, and I don’t really think this is what happens at all. Sure, a couple big names keep getting absurd amounts of money pumped into them that allow a seemingly endless timeline of exploration — but that’s not actually what’s happening at those companies. They’re actually on a really tight, short-term timeline; it’s just about raising more money or keeping investors happy with what’s going on.

So that brings me to my critical mass problem with music. Like a VC backed startup, certain scenarios open up where I have time and freedom — for instance, I have an hour and a half or so this morning, because my wife and kids went to church. Therefore, why would I not go create an hour and a half of music?

Two reasons:

  1. Sometimes (most times?), an hour and a half of musical production effort results in… no measurable results at all (this is also true of writing, which is why everything on this site is disjointed and poorly edited now). As has always been the case, many times I just walk away with something I don’t really like and found frustrating to make. Compare that to an hour and a half of cleaning up the house, or getting ahead of stuff for work, where I always get demonstrable results and someone important is always happy. It’s tough to make that tradeoff when time is limited anyways.
  2. More importantly, the output of knowing you have an hour and a half to make something is usually something with scope and ambition of something you know you have to finish in 90 minutes. Those songs are very straightforward, unambitious, and often a little sterile. Verse, chorus, verse, bridge, chorus — crap, is that the van door? I gotta go, export, done. You can try to save it until next week, but I’ve always found songwriting to be very momentum driven. After seven days, the moment you were capturing is often long gone.

The Hour & a Half Business Plan

You’re seeing the startup equivalent of the hour and a half time investment throughout technology these days, and it’s more obvious than ever. Money is available to enterprise software startups that can run the exact same playbook that’s worked a million times, with the same bunch of founders with the same set of experiences and connections. Those startups are expected to hit certain growth patterns based on the success of other enterprise software startups, move up/down market, blah blah blah, rinse, repeat, and either IPO or be sold.

There’s nothing wrong with that, of course. I’ve worked for multiple companies like this who took this path because it made the most sense for the problem they were addressing. But you’ve got to admit that what I’m talking about is a pretty limited problem set.

Every time I have this discussion with either investors or people who spend a lot of time trying to win investors over, I get the same response, which is an immediate pivot to the financial justification for everything — as if I’m not aware of that after ten years of decks and quarterly reviews. But my point isn’t that VCs should start making unrealistic, borderline philanthropic investment strategies — it’s that the effective branding of VCs, the Valley, and “tech” as an industry (versus a concept that slowly moves along, well, everything) as this massive agent of useful social change has actually caused some of us to believe it, and just assume that cloud software for banks, or a variety of narrow systems designed to convert layer after layer of labor into disposable contractors are somehow the appropriate next stages of social evolution. All because they fit a desired exit timeline for today’s VC approach to investment strategy!

Let me say it more plainly.

  1. Capital is time to operate.
  2. Capital only comes from so many places.
  3. Bank loans are too small and too hard to get for most potential solutions/businesses/ideas.
  4. Internal investment at large companies is minimal and often constrained by various innovator’s dilemmas and the general inability of successful companies to grow and spread change and new ideas.
  5. VC money — and this is directly contrary to its carefully cultivated brand — is much too constrained in ambition, timeline, and willingness not for risk, but for actual loss to solve problems that actually matter at this point.
  6. Inherited wealth (as with business capital) mostly goes to people who don’t want things to change (because they are wealthy with things the way they are), or who are idiots and/or unmotivated.

So… what’s left? How did America come up with so many amazing innovations and honest-to-God progress through so much of the 20th century? It’s almost like we had a vehicle for broad, loosely managed but highly directional investment in things that, unlike VCs or banks, didn’t need to worry about capital returns.

Okay fine, have a hint.