“I’m talking about the time-honored practice of unloading records you once deemed worthy, possibly taking a financial loss, depleting your collection, and maybe getting nothing but a handful of cash in return — which, invariably, gets pissed away on food, drinks, or parking.”

In the mid 90s, I was running my first Internet company from an oversized office in downtown Lincoln, Nebraska. I practically lived there. I moved in a couch, a nice stereo, and my entire CD collection, which was probably 75 CDs.

Below my office was a Twisters — the ubiquitous record shop in town. Like any music store of the time, Twisters would gladly buy back most any CD — for $2–5, usually. And I knew many people who took them up on that option.

Inside the Twisters was a coffee shop. It was because of this coffee shop, a generous friend from college who got a job there, and my tendency to pull all nighters at work that I first started drinking coffee. I think he got me hooked by slipping me the flavored coffee of the day for free. Hazelnut anyone? Mmm. I pulled plenty of all nighters in our previous office (which is also my house) before that. But, sans coffee shop below, my drug of choice was 32oz Mountain Dews from the Subway sandwich shop.

Coffee was certainly a lifestyle upgrade. The only problem with it was the cost. I was broke at the time. Like, really broke.

Here’s how broke I was: I bought a car for $227 dollars. That was the price on the windshield at the dealership; I didn’t even negotiate. I couldn’t believe my luck while driving by with my girlfriend (my only form of transportation other than my bike). We drove in and found the ’67 Ford Custom 500 ran well. So I charged it to my credit card (or borrowed from my GF maybe) and drove off. I loved that car. It was definitely a steal. But I lost that car by accumulating too many parking tickets I couldn’t pay and getting towed. I couldn’t afford to go get it unimpounded (pounded?).

On many occasions, after a furious night of coding and scheming and enjoying my T1 Internet access at the office, I would anxiously await the arrival of 8am when the coffee shop opened to get my fix to power me through the day. But sometimes, I didn’t have the money for a coffee. There was an ATM nearby that still gave out $5's, but often I didn’t have that much. I couldn’t rely on my generous friend to always be working. I remember literally digging through the couch cushions (which only worked a couple times) and checking people’s desk drawers (they were family).

But I never once sold a CD.

Today, I’m perfectly comfortable with the post-physical music and even post-ownership of music world. Spotify and Pandora are my dream scenario. But back then, my CDs were precious. More precious than my car, apparently — or I’d have sold some to pay for parking. Or maybe it was just the principal of it. Getting $4 for something you paid $12 for was the epitome of bad investing in my mind.

I was proud for never falling for that sucker’s bet — even if it meant foregoing a much-needed caffeine boost now and then. But in retrospect, it makes me wonder: If I was so conscious about good investing, why didn’t I instead buy a coffee maker for the office and get my fix for a fraction of the price? Probably because that would have required even more CDs.

CEO of Medium, partner at Obvious Ventures, co-founder of Twitter, curious consumer of ideas

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