#77 Jason Calacanis

Jason Calacanis (@Jason) joined James Altucher to talk about startups, podcasts, and how surfing is like business. Calacanis is the founder of Inside.com, host of This Week in Startups podcast, and an active angel investor at AngelList.

Their interview begins with Calacanis’s history. He started Silicon Alley Reporter in 1996, as a trade publication focused on New York’s Silicon Alley. Calacanis said that while he was running the company, he felt like he “was the Silicon Alley Reporter” and this identity bothered him. Seth Godin (episode #86) said in that he felt the same way about his company and noted that after he sold it, he felt like a loss of part of himself.

Eventually, Silicon Alley Reporter failed and Calacanis began laying people off. It wasn’t fun but Calacanis tells James that it also wasn’t something to get upset over. He said, “okay, it’s low tide, let’s find another beach.” Like a surfer might drive along the coast and look for parked cars, Calacanis looked at where his Silicon Alley reporters landed – at blogs. At first he was dismissive, thinking that because they weren’t edited, they wouldn’t be good. Once he took some time to examine them more deeply though, he saw that this was exactly why they worked. So he started doing what Gary Vaynerchuk (episode #2) calls “the most important word ever.”

He hustled. Looking at him now it seems like he had hit after hit, but that’s never how it really works. Calacanis had to build up his skills at business building. Jairek Robbins (episode #96) told James that this was something he too had to learn. Jairek was almost perfectly following in his father’s footsteps (Tony Robbins, episode #62) but he had to learn things the hard way, to make his own mistakes and said that he “learned more by figuring it out on my own.” The same was true for Alex Blumberg (episode #70) who told James that he doesn’t know how he solved the problems that come up other than by solving the problems. Ramit Sethi (episode #36) said, “don’t wait for inspiration, test your way to it.” Kevin Kelly (episode #96) said that if you have money you buy solutions, if you don’t you figure them out and learn something along the way. There’s value in the experience of figuring things out.

For Calacanis this meant beginning Weblogs, Inc. a blog network with some notable names then and now, among them, Engadget, Joytstiq, and Download Squad. Finding sites to form a network was easier then Calacanis said, because there was less noise to parse through. You could look at some of the new products on Delicious and find something of value. Now though there are sites like Product Hunt where hundreds are released each week. Calacanis is echoing what Kevin Kelly  mentioned about being lucky. Kelly said, “I lucked out to be at this moment when the digital culture and the nerdy stuff I was interested in became mainstream.” For Calacanis, it was luck in the timing. Five years back and there’s nothing to see. Five years forward and there’s too much.

Part of the avalanche of options is thanks to the access technology provides. “There’s a zillion things you can just do and that’s pretty fantastic.” Calacanis told James. You could setup a blog, an e-commerce store, and a podcast in half a day. Things that took weeks takes days. The cultural gatekeepers are gone – Godin’s idea, not mine – but they are gone for everyone – Vaynerchuk’s idea, not mine. You have to “put up or shut up” as Adam Carolla (episode #25) told James. In the past fewer people could get book deals, start companies, or build websites. Those limits are gone but it means larger crowds. A decade ago Andy Weir (episode #92) tried for three years to get a book deal and got nothing. Now his book is becoming a movie. For every Andy though, there’s a Randy out there that missed.

James asked Jason what someone in their cubicle might look towards as a growing area? Calacanis says whatever you create, he looks for two things in your work.

1. Know your space. “There’s  level of deep, deep obsessive knowledge you need to have of all your competitors. Of all the nuances of their products. Of the history.” He says to James that you shouldn’t be in the smartwatch business if you don’t know the in and outs of the Apple watch and about Pebble’s Kickstarter. “Know this stuff cold.” he says. He likens it to this clip in Rounders, which David Levien (episode #85) said is based on something he really saw and Levien was only able to include this in his movie because he knew his space.

Calacanis calls this “asymmetrical advantage of information.”

2. Do good work. The other thing he looks for is good work, in general. If you have a  well-designed site or good technical programming, then you probably won’t forget that overnight.

The conversation moves to angel investing and Calacanis returns to these ideas. When James asks how someone can get featured on the AngelList (another crowded market) Calacanis says that you should just partner with someone. He goes on to say that if you research one of the syndicate heads you’ll have a better chance. Carol Leifer (episode #66) mentioned the same expectation to James. She said that if someone connects with her and knows that she likes animals, a bit of her history, and has good things to say, she’ll be more likely to work with them.

Calacanis said that one crowded space people shouldn’t worry too much about is reporting and press. Instead of hoping for coverage, people should “take ownership of communicating their ideas.” Build a blog or newsletter and use those mediums to communicate he said.

James and Jason speculate about the future of IPO’s and wonder what role they might play. Facebook was down to almost half of their valuation six months after their IPO and that may have scared some companies away from their own IPO. That’s true, but for the people not involved in the initial investment, it’s valuable to look at the bigger picture.  Two years later the Facebook stock was triple the low. More evidence to not read the daily news which included headlines in the fall of 2012 like “Is this the beginning of the end?” An article at Bloomberg said, that “It might be fatal to your career to be viewed as the last chump to get out.” Ladies and Gentlemen, your daily news.

The problem in the daily news isn’t that the news is bad, it’s that the good stuff is hard to find, especially among the hyperbole. In Fooled by Randomness, Nassim Taleb wrote, “For an idea, age is beauty…For an idea to have survived so long across so many cycles is indicative of its relative fitness. Noise, at least some noise, was filtered out.” Which is a less than applauding introduction to…

Inside.com, Calacanis latest company. It started when he asked, “if people on mobile could read news more efficiently, that would be a great thing for them.” Inside.com then is a snippet view of news stories, organized around themes like Disney or Podcasts. To their credit though, they’ve avoided the “salacious” headlines that typically drive news.

James picks Jason’s brain about his experience building a podcasting network, but Calacanis says it’s really hard. You could “do it as a loss leader” he says. Or as a way to learn from people. But as a business, that situation is harder to figure out.

The end of the interview circles back to Calancanis’s situation when his other startups shuttered and it reminded me of something Marni Kinrys told James. She said that when it comes to being confident, it’s not about being confident all the time. It’s more like a self awareness, an ability to self-diagnosis when you aren’t confident, but want to be, and the know how to build your confidence back up. For Calacanis it wasn’t confidence, but business health. He didn’t always run a successful business but knew when something wasn’t working and what might work instead.

The interview ends with some book suggestions from Calacanis, who says people think he’s smart, but he says he’s just well read. As Charlie Munger said, “I have known no wise people who didn’t read all the time — none, zero.You’d be amazed at how  much Warren(Buffett) reads — at how much I read. My children laugh at me. They think I’m a book with a couple of legs sticking out.”

Jason’s suggestions:


Note: You can now sign up for The Waiter’s Pad Book Club.

Thanks for reading. One final word on luck. Luck is hard to figure out. I’m sure that Jason pursued Weblogs, Inc. because he had the skill to recognize a trend, but there is no success without a bit of luck. As Kevin Kelly said, it’s not that successful people don’t work hard (they do) or aren’t smart (they are) it’s just that they get a bit lucky too.

The Andy/Randy dichotomy will continue on this site after reinforcement from Thinking Fast and Slow and Fooled by Randomness. Both books talk about our mistake in looking at the numerator rather than denominator (availability bias). That is, we take notable examples, like Andy Weir and we think that he represents a class (part-time fiction writers). Rather, he’s the exception. There are many people writing space fiction who didn’t make it, we will call them Randy.

22 thoughts on “#77 Jason Calacanis”

  1. […] Jason Calacanis said his finish line is to be the #1 angel investor, not some series of returns. Ryan Holiday warned Shane Parrish about writers angling toward the wrong finish line. Jason Fried pointed out that you can’t be Jeff Bezos, “His success is one that’s very very hard to achieve…most likely you won’t get there…the odds are stacked against you…and if you think that’s the only way you’re going to be miserable.” […]


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