Same job, twenty years later

It's 2026, and a customer email comes into my inbox. Cancel me, my card changed, my envelope never came, did I accidentally buy this twice? Emails like this one make me think of my first job in tech, twenty years ago.

My first real day at Spot Runner, I walked down the public stairs to the bus stop in front of the Siete Mares taco shop, well before dawn. Two buses stood between me and the office: the 444, then a transfer to the 4, west to Wilshire and Fairfax. Spot Runner had launched its public site the week before, and my boss had decided we needed a live customer service rep when the East Coast started. The rep was me, and I was carless in LA. Thus, the absurd wake-up time and transfer. And that first day, the building was locked and empty. The next day I got a special key. I don't think a call ever came in that 6 a.m. hour.

I recently found this gem in old emails.

Haha, I hadn't seen that in twenty years. I was proud of it when I sent it, I guess. Or simply it was an artifact: I worked on this. I made something.

The manual was something I wrote: how to handle inbound customer emails. Our system was buggy (or non-functional), our product was theoretical and our customers were mostly seeking to reset their passwords.

I'm not sure why it's in my old email. Maybe I thought, in the future, people would see this and find it funny, that Spot Runner would be such a household name that the notion that it never existed would be preposterous. I see that excitement/delusion edge in AI right now, btw. Not only was it my first time doing the things, I had the sense it was the first time anyone had done any of these things. I was earnestly trying to do Customer Service in a way no one in the history of the world had ever done.

I reported to this person Lisa, who reported to Dan. Dan was sweet, thoughtful and had the ear of leadership. Lisa was bossy, temperamental, and I wanted to prove I was just as capable of things that she was. Looking back on it, Lisa was experienced and hard-working and she treated me fairly, even if she was a bit cold. I was not very trustworthy then anyway, so the treatment actually makes sense. I was an amateur, but thought I was very capable. A dangerous, if potent, combination.

Later, I would complain about making this very manual; I now see it's a very reasonable request to document your work. Most of that job, most of my corporate jobs, were like this: annoying, but not hard. What seemed unreasonable then seems pretty reasonable in retrospect.

I wasn't good at customer service, but I didn't know that. Dan S, the best boss, took me aside once and said “JC, I think you're going to do great things at this company and beyond, but I want you to be honest, did this thing happen?” And I lied to his face. We both knew I was lying. I still feel awful about it.

All of these reasons may be why I want to automate customer service. Or it just might be because I know that if I have a problem with an online thing, I just want it to be solved.

And so that's why I get customer service notes now in one of my inboxes.

I'm helping my wife stand up an ongoing subscription product for her business. And there's a decent amount of customer service: requests to cancel, to move billing, all kinds of edge cases. So we built a system that mostly automates customer service.

What we actually built, underneath all of this, is rules. What counts as a cancellation reason, what a prepaid term is, which month a late charge funds.

And so, twenty years later, I'm still writing business rules, processes and procedures to handle customer service stuff. I'm glad that LLMs figure out most of the hard stuff.

S., the customer at the top of this page, asked whether the new six-month subscription would duplicate the one she already had. There were a series of funny things that had happened in her account. In Spot Runner days, we would have a lot of manual notes to figure all this stuff out. In 2026, the LLM documents all the exceptions, and figures it all out. S. got her Happy Mail back instead of her money, and wrote back.

In June Amy was still answering customers herself within the day. Since mid-July, first-line customer service never reaches her. Between the LLM and me, we can handle it.

Twenty years later

I don't want to be doing customer service, but we don't always get to pick all that we do. Spot Runner was a weird fever dream, a real opportunity and a real house of cards, in one.

I still feel badly about some of the things I did at my jobs along the way. I try to do better now. Telling the truth helps. So does caring: figuring out how I can be helpful, and then doing it. Spot Runner, Amy Tangerine, Meta, all of it. I did some good. I did some bad. I learned. I wouldn't trade it. I can't.