Jason Calacanis has been a perennial voice in the technology community for over a decade, to the ire of some and the entertainment of others. He started out publishing a paper newsletter called Silicon Alley Reporter in New York during the dotcom boom, which eventually grew into a magazine on both coasts. He sold his company Weblogs, Inc. to AOL in 2005, and moved on to be product manager at Netscape. Now he’s working on a new venture called Inside.com that will roll out this fall. (I can’t tell you how it works—that was off the record—but I can tell you it sounds ingenious.)
Calacanis sat down with me in New York to talk about the startup landscape in New York—an issue near and dear to my heart as we continue to test Writebot here in the Fast Company office. Here are the highlights from our discussion.
I always knew New York was going to play a critical role in the Internet, that’s why I started the magazine and did it for a good number of years. The reason was advertising is here, Wall Street is here, media is here, and it’s the best city to live in in the world. The art scene here is better than almost anywhere in the world, and it’s clearly the best city in the world where young, creative people are going to want to be. Not playing a role is impossible for New York.
Sequoia Capital invested in Tumblr. [Partner] Roelof Botha decided he’s going to take a cross-country flight every eight weeks to go to that board meeting. That’s when you know something’s up in New York—when you see the VCs in the Valley take a cross-country flight. The ideas coming out of here—Foursquare, Tumblr, Gilt—are original and bold. Whereas in I think Los Angeles you don’t see that same boldness. Boston sometimes you do, sometimes you don’t.
For a first-time entrepreneur, there’s nothing better than being in Silicon Valley because there is so much going on, and there’s such a large number of inventors, that even a B level idea or a C level idea could be nurtured and be given venture capital there. Here in New York, maybe the B level could be nurtured and get angel investing, but the C level idea probably wouldn’t fly. Because there’s not enough investors here.
The stuff coming out of Silicon Valley is dorky. Like it’s not very sexy. So New York, I think, has a branding advantage, a design advantage, and a media advantage. Like, I mean the New York Times is here—you guys are here. A lot of times the Silicon Valley folks come here to do their press tour to try to get you guys to write about them. So if you’re in New York you just have this inherent press advantage. It’s very important as a startup to get early press, because although it may not be a large number of people, having a Fast Company story—some of those people that read it are going to be your next employees and hires, your next investors. Others will be advertisers and maybe a thousand of them are potential customers who will try the product. That could be very material. It may be small numbers compared to like a hundred million YouTube views or something, but those readers could be huge catalysts and amplifiers.
When you’re younger and you’re starting your career, write about something you really know well—even if it’s very narrow. If you know about ad platforms, write something definitive and be honest and authentic; people are drawn to the person who is real. The problem most people make with their media presence is they’re trying to craft a media presence as opposed to just consistently publishing who they are. For better or worse, I’ve consistently published who I am for 20 years, and it means I have a really big audience: Over 30,000 emails, 150,000 people on Twitter, and a couple hundred thousand on the other social networks. That doesn’t mean they’re going to agree. But those people will give me a chance at least.
To get readers, I think you have to be authentic and be a good writer. Writing is just clarity of thought. I think early in my career as a writer my writing sometimes was passionate, but maybe not as good as it is now because I didn’t have as much clarity of thought. Now when I write, I can write a 2,000-word piece in one sitting and it just flows—just "boom." I’ve seen enough in the world, I’ve experienced enough, that I have clarity of thought. I don’t think anybody under the age of 30 should be expected to write [like that]. You know, like I’ve been offered two or three book deals, and I said I’m just going to wait until I’m 50. I’m 42 now. Let me get one more startup out of myself and then I’ll write a book.
I’ve never stopped writing about what I’m building. I started writing about why I’m building it. Right? So in the next couple of months you’re going to see me write a lot about media. And it’s going to be because I’m launching a new project, Inside.com, in October that has to do with the media. But I’m not going to lead with "here’s my project and the 17 new features," because nobody cares. They might care someday when they use it, but they’ll care when they load it and they use it and they love it. My writing is not going to convince them to love any product. What my writing might do is convince them of why I built it or why it’s important, right?
Step back for a second and say, Here’s why I built what I built. When I angel invest, I ask people that. Why did you build this? Sometimes they’ll say like because it’s a big market and I think we could make a lot of money. Or they’ll say well, because Pinterest sucks, and they don’t have these three features. Those are terrible reasons to build something. But to say "I built it because I’m passionate about this space and I was frustrated by these five or six things," or, "I saw an opportunity to make something that made people’s lives easier," that makes people say: Okay, now let’s really talk about your idea. Always try to couch it in something bigger.
If you’re a young entrepreneur and you want to get into blogging, you want to write your ideas, write about something much bigger than yourself. And it’s okay not to have all the answers. It’s okay to say that. It’s okay to say: I’ve been thinking a lot about the issue of RSS going away and Google Reader going away and why didn’t Google want to support this product anymore? I don’t know, but here are some theories I have.
Dave Winer—who doesn’t get a lot of credit—a lot of times when he writes, it’s not about him trying to wrap everything up in a bow. I perceive him as like a snowball roller. He just likes to roll snowballs down the hill. And sometimes those snowballs, they get big and they turn into avalanches where everybody is talking about what he’s saying. Actually, if you look at my writing, you can tell I always studied the way he was able to capture a lot of attention for his ideas. I think I’m a snowball roller, too. Be a snowball roller.
[Image: Flickr user Bruce Thomson]