In early 1997, I was working at a hosting company–my first real job in technology. My dream job.

Back then, few people carried laptops because they were still quite large, heavy, and underpowered, which meant I had a company-provided desktop computer (also large and heavy) at the office and then my personal machine at home. There was little in the way of email syncing since most email accounts used POP instead of IMAP for some reason.

One day I thought, “It would be great if I could check my work email from my browser at home,” which was a lightbulb moment for me. Why couldn’t I check it from my browser?

I started working on it.

Today, I can picture in my head the code I would need to write for such a task but, back then, I was still too green. I mocked up the HTML since that’s what I knew the best. I think I probably planned on using PHP as the backend language since a co-worker had written AtlantaMLS using PHP (version 1) and mSQL, and I could ask him questions when I got stuck.

Then, one day, a terrible thought popped into my head: “Why would anybody want this?”

I stupidly believed that thought and dropped the project. A few months later, Hotmail sold for (inflation-adjusted) $700 million to Microsoft.

Now, let’s not kid ourselves. I didn’t have the business experience to parlay my project into a huge exit, even in the frothy days of the early web. That’s not the problem. The problem is, I gave up on myself. I hit a roadblock and used that to convince myself that nobody would want such a product.

What I should have done… well, what I should’ve done is market research right from the start, which would have told me that of course people want this! Then I wouldn’t have had that particular piece of ammunition to use against myself when doubt crept in. When it inevitably did, the next thing I should have done is explore where those feelings were coming from and disobey the fear. If the product sold then, great. If the only person to ever use it was me then, at least I would have had a handy tool and would have learned a ton in building and trying to market it.

A few years later, I was talking to my grandfather, and I told him that story. He relayed his own version it, though without the self-doubt and with a lot more intrigue:

In the early 70’s, he was running a successful real estate and residential home construction business. One day a guy who he knew to be “a crook” stopped by his office and offered my grandfather an opportunity to go in with him on some scheme he was planning. My grandfather told the guy he wanted nothing to do with it and threw him out.

A few months pass, and this same guy calls my grandfather up. “I just wanted to thank you for not turning me in on that deal. As thanks, I want you to buy up as much property as you can in this area of downtown [Atlanta].” My grandfather laughed at him for several reasons. See above: this guy had a less-than-stellar reputation, but also because the area the guy was telling him to buy was a shanty town. Sure, he could’ve gotten the property for cheap, but why? He told the guy as much and hung up.

Today that part of town is called CNN Center, and the city passed the law making it so a few months after that phone call.

I don’t blame my grandfather for doing what’s right, and I don’t think he regretted it. The guy was a crook, after all.

I don’t really regret not “inventing”[1] webmail. I wish I had learned sooner how to disobey my fear, though. I also wish I had asked my grandfather for more stories like this while he was alive.

[1]: A lot of people invented it, really. It was such an obvious idea.