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.

There are a few different ways I’ve seen people go for it. I’ve been here for 10 years, I’ve tried them all and I’ve seen lots of friends have at it, too. Here’s what I can take away from them all.

The burnout, not fade away

Most people, when they show up here at 22 or whatever, just dive in. You’re out every night, finding a job is secondary, and you run yourself ragged. If you’re lucky you’ve got a little savings, but at 22, $10,000 in the bank feels like it will last forever. So you go nuts, until panic sets in.

The good: You’re seen everywhere, and that makes a huge difference to people in NYC. The hardest thing to establish in New York is trust, and a lot of that is based solely on seeing someone more than once. This also increases your luck surface area, and good things are more likely to come to you.

The bad: If you were a big fish in a small pond before you moved here, like most people, you think you know something. So you inevitably learn the ropes the hard way and waste a lot of time. You make a lot of mistakes, and you spend a lot of money.

The outcome is that in two months or six months, you are exhausted, your money starts to dwindle, and you retire.

The long slow

This is the heart of it. You do what you gotta, and chip away at your passion. Some people get jobs they don’t care about, others, like me, set up freelancing, so we can alt-tab when we want.

The good: You can take your time. If you’re dilligent, and consistent, you meet a lot of people, and stand to learn a lot from them. You’ve got time to stop and smell the roses, and more importantly, modify your game plan as you trudge along.

The bad: Man, you get discouraged. Progress is slow, and it’s hard to keep your eye on the prize.

The after school special

Some people hit the ground running. Others are more responsible and try to eek out their passion during nights and weekends. Gary Vaynerchuk calls this hustle 2.0.

The good: you are a responsible adult, it’s low risk and feels way better than watching t.v. every night. You also have to take breaks every day (the day job) which means lots of time to think through what you’re going to do that night. It can be very productive!

The bad: any girlfriends or wives will not see you for months on end. It’s easy to lose track of the end goal chipping away every night. It’s tough to keep up momentum.

The hack-a-thon

The newest method I’ve seen for getting a project out the door is the hack-a-thon. Assuming you’ve got something that has a clear beginning and end, you can lock yourself away and get it done. It’s fun with friends! Just set very clear goals.

The good: it’s a shorter commitment, and you (hopefully) walk away with something tangible – a 3-song EP, an MVP of your new web app, a first draft of your new short story.

The bad: It only works for certain kinds of projects, with certain kinds of people. You won’t sleep for 3 days.

After fighting with New York for 11 years, I now think of projects in terms of the hack-a-thon to get me started, and then aim for a week or two of nights and weekends to polish it off, and see if I can get people interested. I’m promising myself, no more burning out!

I was proud of my creation. So when I got around to making the marketing pages, I was sure to include an “about the Birdy” page that included my story and a photo of me. After a couple of weeks I noticed a trend in the analytics. People were visiting the “about us” page, and then signing up. So I moved my photo and story up to the homepage and saw an increase in sign ups.

I wanted to talk to the people signing up. An occasional email through the contact form wasn’t enough. So I installed SnapEngage, which adds a classy little “chat with us now” window to every page of your site. Nice and subtle, which is my own personal style. A few people a day would chat with me, tell me about bugs they found, or make suggestions. It was great, but SnapEngage was expensive. So after some research, I switched to Zopim, because it was cheaper, even though it wasn’t as classy. It has this big goofy “chat with us now!” speech bubble over the little window, and it says my name in big letters. Twice as many people started chatting with me.

I finally get the store proprietor analogy. I start every support email with “Hey!” because that’s how I talk, and if someone walked into a store I owned, that’s how I would greet them. I apologize when someone has trouble, and I share in their joy when they have a great experience. Even though not all the feedback I get is positive, it all helps me learn how to help better server the next person to walk through the door.

Ira Glass
(By way of Mike Helmuth)

Here’s a trick I’ve been using for a while now that works well. Write your script to do whatever task you need. This could be in any language. Have it print statements of it’s progress as it goes along – “found 10 records”, “starting loop of 10 records”, “updating user record #1″, “updating user record #2″… you get the picture. This is great because you can go hit the page in the browser and test it a few times.

Now here’s the trick. Don’t reference the script directly in your Cron job. Write another script that uses Curl to call your script and return the results, and then have it log or email you what it returns. What’s nice about this is that it will return your “found 10 records” statements, but it will also return anything else “printed” to the page, like warnings, and fatal errors.

All you have to do is remember to check your log or emails once in a while.

I was able to get the proof of concept for my newest venture, the Birdy, out the door in a weekend, because I’ve been effectively practicing building web apps for 10 years. Now comes the hard part of actually turning it into a business, but I feel prepared because for the last ten years, I’ve also read every book I can get my hands on about business, I’ve gone to meetups, I’ve listened to podcasts interviewing experts…

My friend Brandon tells the joke:

A tourist walks up to Picasso, hands him a napkin, and asks for his autograph. Picasso signs it. Then the tourists says, “would you do a little drawing on the back?” Picasso does a little sketch, hands it back to the tourist, and says, “That’ll be a million dollars.” The tourist says, “But it only took you 10 seconds.” “No,” replies Picasso. “It’s taken me 60 years.”

If you are working on marketing, this idea goes even wider. Your goal is to constantly be in the conversation. What’s the rule of seven? Someone needs to see your brand name seven times before it sticks. Even if it’s not exactly true anymore (it feels like it’s gone up), it’s not a bad rule to live by.

If your goal is to get someone’s attention seven times, everything is an asset. Anything you’re involved in can be republished, retweeted, or written about. Give a presentation, write a tutorial (on your product or someone else’s), post an idea.

The extension of this is promoting other people’s stuff. Retweet, link to, republish, react to… Help promote other people, and they’ll do the same for you, even if they’re just promoting you promoting them.

Your audience just doubled. You got a pair of eyes one more time. You (hopefully) added a little value to someone’s day, and they’ll appreciate it.

I started by deciding what I wanted to focus on, professionally. I love helping people accomplish tasks, solve real problems, with software. These days, the way we do that is with web apps. So I decided to focus on web application development.

I can build my own (and I do) but I have rent to pay until those are earning enough revenue. So I looked around for people with ideas for web apps, but needed help building them.

In New York City, those people hang out at Ultralight Startups, my favorite meetup. Every month, 100+ people get together and talk about starting businesses online. Too easy.

Because I’d figured out exactly what I wanted to do, I was able to define my customer. That led me to a room full of leads, potential partners and many customers. Can you describe your fish?

My best friend is aggregation. iTunes aggregates my podcasts. Google Reader brings all my blogs into one place. HootSuite helps me manage 6 Twitter accounts form one place.

But then I started getting comments from my favorite bloggers and podcasters, “You never comment!”.

I realized that my efficiency had moved me a degree away from the source. Aggregators are great for consuming, but make interaction counter-intuitive. So I stopped commenting, leaving feedback, being involved, and I was getting less out of my reading. Without comments, and even a sense that people writing or talking on the web is a conversation, I didn’t absorb as much!

Now I make the effort to click back to the more popular blogs I follow. And I try to visit the pages of the podcasts I love. I’ve come full circle. It’s more important to me to be involved.