Early in my career — and in my teens — I was doing web design for local businesses. It was the late 90s/early 2000s, and the Internet was taking off, and people

Early in my career — and in my teens — I was doing web design for local businesses. It was the late 90s/early 2000s, and the Internet was taking off, and people wanted websites. I have plenty of stories from this era, but today, I'd like to talk about Demmer. (That's not his name, as I want to preserve anonymity, but it's close.) Demmer was an old man, retired, and excited by what the Internet could do for him and his organization. They were, he told me, building a state-of-the-art retirement center. And what a retirement center it was. It offered every luxury. Five-star food. Movie theater. Staff tending to your every needs. A better living environment than you'd ever have had pre-retirement. They had Dot Com billionaires investing. It was HUGE! (Best I could tell, this never existed in any form, sadly. Demmer was the sole representative, and I began to suspect this was more wishful thinking than anything.) Demmer's ask was simple: Take a document he wrote and put it up on a website. Easy. Shouldn't take long. I billed him up-front for the full cost — a couple of hours of work. A couple hours that took a month. To send a document. With daily, angry voicemails. I began to call this lovely interaction the "Daily Demmer." He'd send an e-mail with the document, and the e-mail would be blank. I'd reply, and he'd respond via voicemail explaining I must have done something wrong. I'd respond with a voicemail of my own, asking what he tried, and that I'd help. He'd get defensive, say he knows how to e-mail! He e-mails all the time! His voicemails graduated to long, expletive-laden rants within a week. Finally, I got him to walk me through his attachment process. Step 1: Open the document. Step 2: Compose an e-mail to me. Step 3: Place the document on one side of the screen, the e-mail on the other. Step 4: Hit send. "Ah-ha. Well, I'm sure it made sense to him. I can set him straight," I stupidly thought. I walked him through attaching the document. Find this button, click it. Find your file. Click Attach. He nods along over the phone. "Uh huh. Okay. Got it." Good, good, this is working. "I'm hitting Send." I received an empty e-mail. Turns out, he had dug in his heels. He knew e-mail! He sent plenty of e-mails with documents to all the investors. And he did so with the same steps: Place both on the screen, hit Send. I'm just a kid, what do I know? Rinse and repeat for weeks. Eventually he drove to town and just angrily handed me a printout. I got the website up within a couple hours. He canceled his hosting within a month. I never heard from him again.