It’s been fifteen years, and I’ve been building websites about as long as I’ve been making music. When I first started my career as a rockstar DJ, the challenge was making music. Home recording was a possibility but expensive, and computers hadn’t quite caught up. You still needed synthesizers, samplers and drum machines. If you could make a decent recording of your music, you could be one of the relatively few musicians online.
Then computers caught up, and it was no longer hard to make music. Even before Garage Band, there were lots of programs that let you put a beat together. But how could you get your music out there? You could sell your CD’s through CD Baby, and you could get a few copies in your local independent record shop. It was even harder for vinyl, because they were for DJ’s and the die-hard fans, and they were really, really heavy. 
Then along came iTunes, and eMusic, and then Amazon, and suddenly distribution wasn’t an issue. For a while, you still had these CD’s to hock, too, but eventually we just stopped bothering. It was less fun not having merch at shows, but that’s what stickers were for.
The last phase has seen the challenge shift to getting attention. Now anyone can make a tune. And get it distributed with a little effort. We’ve seen so much great new music, and great new musicians, come to light, but it’s hard to find them, and it’s tough getting found.
I think the startup world has seen something similar. When we first heard about “startups” and new, tiny tech companies selling millions, making a real web application was not cheap, even for the companies that followed some early version of “agile” or “lean”.
Then servers and bandwidth got cheaper, and programming got easier. The challenge moved to getting eyes. Five years ago my mom was not looking to the web for things like travel, as she does now. How could you get enough people to sign up to make your first million?
The internet has now become a way of life. Marketing is certainly not easy, but there are books, and blogs, and siminars about how to get the word out. We’ve got app market places, mobile economies, and much of the rest of the world is as savvy as only the U.S. once was.
The last challenge, I think, falls back on people, in two ways. First, most problems have been solved. We don’t need another travel site, another to-do list, or another Facebook-meets-Twitter mashup. Watching the people around me, I would say a challenge now is a plain, old-fashioned Good Idea. The second part is the idea has to find the right people. You need someone who has the time, money and or gumption to execute, and they need to surround themselves with the right people.
It’s been an interesting 15 years. I look forward to what comes next.