> but no PC Magazine Product of the Year!

Well, hitting the first home run took about a decade full of base hits and more than a few strike-outs on the way to figuring out what I needed to know to do a tech startup well.

> What is the "weird" kid doing today?

Over the last decade I've spent increasing pro bono time trying to 'pay it forward' talking to classes and groups of erstwhile entrepreneurs, so I've heard versions of that question a LOT. It actually took me a couple years before I realized there is no 'right' answer because the right thing for each person differs depending their unique personality, skills, interests, context and life journey.

The most helpful thing I can share isn't a guess about which target you should aim for but rather some advice about how to approach your journey. First, I hope you want to be a tech entrepreneur because that's the only thing I know about. I have no idea what skills will be in demand to get a high-paying, secure job or how to get promoted. I had to become an entrepreneur because I was terrible at being an employee.

I never aimed for my guess at what would be "hot" next and I doubt my guess would be right anyway. Every time I found success it was by starting with a real problem some customer actually had. Initially that customer was me or a friend but it doesn't matter. It just has to be a serious enough problem that motivated customers are actively looking for new and better solutions than what exists. Then figure out a way to solve their problem better enough that they'll actually buy it. It doesn't have to be perfect in every way, just better enough in most ways and perfect in at least one way.

In fact, some of my best products became hits by cleverly solving one part of a problem SUPER well, but only did so at the cost of some odd downsides in other areas. Here's a generic example of the pattern that worked: my friends and I all desperately wanted a Zig-Zag Widget but good ones were stupid expensive and the ones ordinary schmoes like us could afford Zigged and Zagged like shit. But while we were bitching about this sorry-ass state of affairs over pizza and beer one night we theory-crafted how it might be possible to make a Zig-Only Widget ordinary mortals could afford. The dumb idea was by not Zagging at all, it just might be able to Zig even better than the best. Since we all had no Zig or Zag, that seemed like a trade-off we might be pretty okay with. Turns out other people were too... especially after we worked on adding some 'pseudo-Zag' features that worked around the worst parts of not Zagging. And that's how we came up with the world's best Zig (but no Zag) and sold it at 1/4th the price of even a half-assed Zig-Zag. Not really new technology, just a very clever mixture of the exact right old tech with a little new stuff, some clever UX innovations and cool workflow integrations. Blam! First Product of the Year.

If prototyping dozens of different iterations and trying each one out with real, live problem-having customers and listening empathetically for hours to their constant complaints, ridiculous demands and occasional awesome suggestions sounds like fun, then you may have found your calling. If you just want to write great code for a good paycheck and be left in peace, then, my friend, run the other way. :-) It's ironic because I got into making products because I loved programming but after the first few years, I wasn't writing much code anymore. It was invaluable that I'd learned the business by starting as a self-taught, down-to-the-metal, assembly language, real-time graphics programmer because I was able to identify and hire programmers far more skilled than I'd ever been but after the first million in revenue and 20th employee I personally spent more time writing or reviewing ad copy and legal contracts than code. But that's also invaluable because as the company grew and various fires flared up in every part of our business, I got pretty damn good at doing marketing, sales, PR, finance and even legal stuff myself when necessary. And all that was the best prep ever for being able to run the place when we hit a hundred million in sales and hundreds of employees.

I used to hate the constant looming threat of existential doom always hovering over our tiny startup. Then one day I finally understood that the constant stream of scary new challenges were there to force me to keep growing and learning new skills. not only survive, but to level up and feel the satisfaction of summitting ever higher peaks. I hope you'll find the same on your journey. The best part is now that I'm retired, I'm back to programming in 8-bit assembler and 4K of RAM, except now I have a rather expansive collection with every model Atari, Commodore, Sinclair and Amstrad ever sold. :-)