I’ve written before about how much I like delegation and automation. Here’s a trick for managing too much communication. Gmail has a great “lab” called “send and archive”. It makes it one click to reply and get the email out of your inbox. If this makes you nervous, add a BCC to FollowUpThen. The goal is to get the email out of your inbox, until the person responds. Then it pops back up for your attention. If they don’t reply? It wasn’t meant to happen. …Or check your Spam folder. 
Too many contacts, keep your balls in other people’s courts
How the 80/20 rule has shifted, in music and in startups
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.
The different ways I’ve seen people “go for it” in New York City
The Long standing joke in New York is ask anyone what they do, and they’ll reply with actor, comedian, start-up founder or some other lefty goal. Press them, though, and they’ll admit they bartend, wait tables, deliver packages… This is the hustle we’re all used to. There’s this thing called rent…
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!