Web Masters Episode #91: Jason Calacanis


Jason Calacanis:

At the time, profiles were a big deal in media. If you did a profile of a person, the New Yorker or Wired would do profiles, both of them had done profiles of me. And that was the height of achievement, was being on Charlie Rose or having a New Yorker profile. In the 90s, I got both of those check boxes. If you were a New Yorker and you did both of those things, you were part of it basically, you were part of whatever it was, digirati, literati, Illuminati, whatever, by default. Those were the check boxes, I think.

Aaron Dinin:

And for context, around how old were you at the time?

Jason Calacanis:

That was when I was 29. people don’t even know about my first act. It’s funny, people are like, “Oh, you’re the guy who invested in Uber. Oh, you’re the guy from All In.”

This is one of the things I learned from Bob Dylan, just don’t look back, just keep making stuff and don’t worry about the past stuff, just keep going forward. And I try to keep my eyes on the windshield, not the rear view mirror. And that’s my advice for everybody.

Aaron Dinin:

Well, we’re going to go ahead and ignore that advice, at least for as long as it takes to get through this podcast episode because I asked our guest to spend an hour with me looking back on what he described as his, ‘first act’, the act most people don’t even know about. He was the founder of a very popular late 1990s magazine about the New York tech scene. It was called Silicon Alley Reporter. But of course, that’s probably not why you know him. And if you spent even a small amount of time in startups, I’m pretty sure you do in fact at least know of him. He’s one of the most prominent thought leaders, investors and podcasters in the tech industry. He is Jason Calacanis, and I’m thrilled he’s joining us here on Web Masters. Are you ready to hear his story? Let’s get dialed in.

[INTRO]

Aaron Dinin:

Hello, and welcome to Web Masters. I’m Aaron Dinin, your host. I’m a serial entrepreneur and I teach entrepreneurship at Duke University. This is the podcast where we do some learning about entrepreneurship while exploring the history of the internet and worldwide web. We do it by talking with some of the most impactful entrepreneurs of the digital age. Impactful is a particularly interesting concept in the context of this episode’s guest. Normally, when we think about entrepreneurial impact, we think about founders building massive world changing companies. But what about discussing those companies or providing education about those companies and the people building them? What about keeping members of the entrepreneurial ecosystem thoroughly informed? And what about connecting entrepreneurs with each other? Those are all impactful things too. And that’s why I’m excited to speak with our guest on this episode.

But before I share that conversation, I’m going to share a quick word about our sponsor. Web Masters wouldn’t be possible without the help and support of our sponsor, Latona’s. Latona’s is a boutique mergers and acquisitions broker that helps people buy and sell cash flow positive internet businesses and digital assets. That includes things like e-commerce stores, SaaS apps, content websites, domain portfolios, Amazon FBAs, heck, probably even popular podcasts like the one our guest on this episode has. In other words, if it’s a profitable internet business and you’re thinking of selling it, then be sure to talk with the team at Latona’s. Their expert brokers are going to be able to help you get it sold for a great price. They can also help you buy an internet business if that’s more along the lines of what you’re looking for. In fact, you can see listings for all the businesses they’re currently helping sell right on their website. It’s Latona’s.com. That’s L-A-T-O-N-A-S.com.

When I first began my entrepreneurial journey, one of the things I had to learn was how important the community is. Yes, it’s certainly possible to start and build a successful venture completely outside of the broader entrepreneurial ecosystem but I wouldn’t recommend it. I’d like to think the guest on this episode of Web Masters would agree. I didn’t remember to ask him when we spoke, which is my bad but well, if you know anything about Jason Calacanis, then you probably know he’s someone who is deeply connected within the entrepreneurship community. That’s not an accident, nor is it recent. Back before he became the prominent Silicon Valley investor and voice of the popular This Week in Startups podcast, he inserted himself into the center of the New York city tech community, AKA Silicon Alley. And I did remember to ask him about how he managed to put himself at the center of that startup ecosystem.

Jason Calacanis:

I held the best parties, that’s for sure, definitely the best parties. It was like Studio 54 in that era. It was quite a party. And I had the best ones for sure, hands down. I think everybody would agree with that.

Aaron Dinin:

Now, you might think Jason’s being facetious but I’m not so sure that’s the case. I’ve spoken with lots of entrepreneurs who were building things in New York in the mid to late 90s, and pretty much all of them mentioned Jason Calacanis and his parties. In fact, that’s why I wanted to talk with Jason. I, like many of you, am familiar with his current work but I was a little surprised to run into his name so often in relation to the early New York City tech scene, a scene lovingly referred to as Silicon Alley, a nod to just how small and intimate the community was in comparison with its west coast peer.

Jason Calacanis:

New York was tiny. In the beginning, it was less than a hundred of us. It was a couple dozen people really, who were building websites and CD-ROMs. Something called the Silicon Alley 100, it was the hundred most influential people. And we got to 60. We just asked everybody, “Does anybody else know anybody?”

And they were just like, “Ah, do you got this person, this person, that person?”

I was like, “Yeah, we got them already.”

I was like, “Do you know anybody else?”

Literally, the list was so thin, they were like, “I have an attorney, I have an accountant, I have an HR person, I know this PR person.”

We literally filled the last 20 or 30 slots with service people who serviced the industry, which was hilarious.

Aaron Dinin:

And for a bit of added context, what was the big difference between the type of entrepreneurship happening in the valley where you are now of course, versus the alley where you were back then?

Jason Calacanis:

Yeah, the valley had Red Herring and Upside as magazines. And people out here were building software, network switches, not really consumer products. New York was obsessed with media and consumer products. The CD-ROM industry, websites that people could visit with content like iVillage or about.com, and advertising. New York had advertising and media and finance and art, and a lot of what got built and put on the internet at that time centered around those centers of excellence in New York. Publishing was a big thing. And so of course, advertising was a big thing. Finance, products, commerce, all that stuff started to go online in New York, had the consumer level for those types of businesses. And out in the valley, people were more focused on infrastructure, search engines, that kind of stuff.

Aaron Dinin:

Out of curiosity, what was your relationship with tech and media? I guess, could you give us maybe the two minute version of how and why you first got interested in computers and the internet?

Jason Calacanis:

Sure. In 1976 or so, my dad bought us an Atari 2600. It was the first video game system. He also had some of the first video games like Pong in his bar in Brooklyn. And then I had seen some computers in New Jersey at my cousin’s summer camp. They had a couple computers and we would write code from a piece of paper into a basic computer and hit run. Then I got my first computer in the early 80s, which was an IBM PCjr with a 300 Baud VEN-TEL modem. And I started doing online dial-up services in the early 80s. And then I ran a bulletin board system, which was a way to dial into another person’s computer over the phone. And then sometimes you’d have two modems on the phone and people could chat one-on-one on a service or upload files, which we call wares back then. We’d hack Chess Master, steal software basically, in the day. And yeah, that was my first exposure to computers.

Aaron Dinin:

That was of course well before the web and the public internet, right. What were some of your first experiences with networking and networked computers?

Jason Calacanis:

Online services and dial-up services were independent of the internet, which at the time was called ARPANET and BITNET. BITNET was the one on universities, ARPANET was the one for the government. And then when I went to Fordham in 1988 and worked in the computer room, somebody showed me on their VAC systems it was connected to the internet and you could do send commands and I think FTP, Gopher, USENET. There was a message board service, subreddits were built into this where you could just post email messages and talk about subjects. And so that was pretty exciting but there was probably only tens of thousands of people on BITNET at that time. And the web certainly didn’t exist, that came into being probably ’93 or so. And then the internet started to become commercially available. AOL created a little gateway to it, CompuServe started supporting web browsers. And then eventually, people figured out how to connect their own computer directly over dial up to internet service providers. And that was all happening in the early 90s.

And when I was going to school at night fixing laser printers and installing Novell networks, it’s a type of network that came before the internet, Novell was a brand, I was literally installing network cards into computers at Amnesty International so the computers at Amnesty International could be connected because at that time in the 90, people would just save a file to a floppy desk and bring it to another person, they didn’t even have email. And so I cut holes in the wall and ran cables from one computer to the next and daisy chained them. Each computer would connect to the next. If somebody kicked their cable, all the computers would go out. They could just share files. And I built when I was at Amnesty, a database to record all of the human rights violations specifically against women around the world, so they could do sorts and provide data to journalists and government agencies who were trying to get information on this type of stuff.

Aaron Dinin:

Part of what I love about Jason’s story and a big part of why I wanted to interview him for the show, is how so much of his life has intersected with the other people we’ve heard from on Web Masters. And that actually starts well before he began hosting parties and bringing people together in New York. For example, just in the answer you heard, he mentioned BITNET, which we learned about when we spoke with BITNET’s founder Ira Fuchs, in Web Masters episode number 32. He also mentioned USENET, which we covered by talking with its creator Tom Truscott, that was episode number 29. He was also networking computers via ethernet. And we met the creator of ethernet Rob Metcalfe, in episode number 55.

Jason Calacanis:

Yeah. Back in the day, you had to put the ethernet card in the computer and then you had to put jumpers to basically say what the IP address was on the card. And then we’d have to run a cable and crimp the back of the cable. But at the time, it didn’t look like a CAT5 cable does today, which looks like a phone cable. It was actually RG 58. It had a connector on it, I think we called it BNC connector. Anyway, you had to plug it in the back and spin it around to get it to connect. Looked like maybe the video connectors on a fancy video camera and you had to crimp them. I had a crimper and I would just go onto people’s desk and crimp the cable and wire it. And yeah.

Aaron Dinin:

How did that manual networking and cis admin work lead you toward a magazine about the early New York tech scene?

Jason Calacanis:

CD-ROMs had gotten big at the time. And so I created a magazine called Cyber Surfer, which was about online services. And I created that in 1993 or ‘4. It was about dial-up services like Delphi, CompuServe, AOL, GNN, all this stuff. And I was writing about CD-ROMs from companies like Voyager or Criterion Collection. Other people were doing mixed media CDs, so that was a big art form in New York in the 90s as this was bubbling up.

Aaron Dinin:

And Cyber Surfer was what exactly, a precursor to Silicon Alley Reporter?

Jason Calacanis:

I had done Cyber Surfer magazine for five issues with a publisher called Star Log but it didn’t work out with them. And so I moved on and did Silicon Alley Reporter on my own, it was just a photocopy newsletter, 16 page photocopy. There was a movement in the 90s called zines, Z-I-N-E, which was a self-produced magazine. It’d be the same as today producing an independent short film. I was really taken by the idea that anybody could just photocopy some words on a page and some pictures and then sell it at Tower Records in the zine section or just hand it out. And so I was passionate, and it worked really well. It grew from a 16 page photocopy to 300 page glossy with an event series doing over 10 million in revenue, close to a hundred employees at the peak. I built that largely off my credit cards and it became quite a big business.

Aaron Dinin:

How’d you grow the magazine from that tiny 16 page photocopied thing you mentioned earlier, into a large well circulated publication?

Jason Calacanis:

From the first episode, first issue, I went and I met with Fred Wilson. At the time, it was Acme Ventures and they just changed the name to Flatiron Partners. I went to Jeff Dodges at Razorfish, a couple other people. I said, “Here’s what I’m making, here’s printouts of it. Would you buy an ad for $250?”

And in the middle, it was a map of Silicon Valley. And Flatiron Partners bought the map for 250 bucks. And Jeff Dodges bought an ad for Razorfish for $250. And I asked them all to give me four ads in advance so I could publish four issues, and they all did. They gave me a thousand bucks and then I went around and I put on the back, 10 issues a year 90 bucks. And I printed up 2000 of them. And then over the next couple of weeks, $90 checks just kept flowing into my mail. I would go down to the mailbox and there would be one. And then I went to a mailbox, it was five. And then I went to the mailbox, it was 20. And I would just be like, “Oh, my God. I just made $1,800 today and it cost 2000 to print these photocopies. In one day, I have enough subscribers to pay for this thing.”

It just very quickly grew. I did the photos, I did the writing, I did the copy editing, I did the design, I did the ad sales and the distribution. I would walk around New York with a luggage rack with 200 issues in it and I would insert them into the Village Voice or Timeout, which was a paper at the time. And these were all free newspapers and newspaper things. And I would just insert my magazine in between it. And then we put a fake QR code on it we had scanned and designed and I would go to magazine stands and I would just put my magazine on the stands with Counting Countries. People would check out and the person at the counter didn’t look but we just wanted people to read it, we didn’t care about making money. We just did gorilla style marketing. And I would just bring it to parties. I have a backpack with 200 copies and I would just put them in my hand and I would just hand it to people, “This is my magazine. This is my magazine. This is my magazine.”

And I wore a Silicon Alley Reporter t-shirt every day for 10 years, I just bought dozens of them and I would just wear them every day. And then threw really great parties and gave people Silicon Alley Reporter t-shirts. And then that became a huge brand and the ads started going for 5k, 10k each and we started selling a hundred of them an episode. And we did a million dollars in advertising in some of the top issues. And then the conferences blew up too. The conferences became I think, 6 of the $12 million, it was more than half the revenue. And most of the profits came from events.

Aaron Dinin:

Why were you drawn to starting what was essentially a media company, rather than more of a tech business?

Jason Calacanis:

Media is a nice way to build your brand. It’s a terrible way to make money typically. If you are a virtuoso and you hit an elite level, Bill Simmons, Joe Rogan, of course that’s different, Kara Swisher. If you are in the elite, yes, you can make millions of dollars or perhaps even tens of millions but that is rarefied error. As much as Bill Simmons or Joe Rogan have made, that would be the 500 person at Google or Facebook right, so just keeping things in perspective. There were hundreds of employees who made a hundred million dollars at those big companies. It’s not comparable to what we do in tech. If you do want to do media, keep your expectations low. If you can make a living or you can make a half million dollars in profit in a media company, you’re doing fantastic. That would be the top 10% of media. Well, look at Buzzfeed, it’s worth less than the revenue they make. It’s trading at below one times revenue, and that’s Buzzfeed. That was the most successful influential brand of the last media cycle I guess, them and Vice.

Essentially, the market is saying the business is worth zero, they’re literally saying Buzzfeed is worth nothing. That’s obviously not true but Buzzfeed is trading at a dollar and 77 cents right now as we’re taping this on June 24th.

Aaron Dinin:

Yeah. Getting rich and media creation usually don’t go hand in hand, at least not if doing this podcast is any indication. But the real value, at least for me, has been in meeting people. I imagine that must have been a huge part of the value of building Silicon Alley Reporter right, you must have met some really interesting people.

Jason Calacanis:

No, it was the most interesting people. I collect people over the years and I would just have four or five people over my loft or for dinner. And then it became 10 people and then it became 50 people and it became hundreds of people. Then it became thousands of people at parties. And so it just spiraled from there. I knew the most interesting people who were doing the most interesting things, and it was across a range of mediums. Bennett Miller was making digital films at the time. Darren Aronofsky was doing this movie Pie. There were people doing interesting things in music, like the Chemical Brothers or Orbital or Moby. There were just interesting people who were dabbling in digital and artists and stuff like that. It was really quite a scene, I haven’t seen anything like it since. Hip hop was also becoming very big in New York in the 90s. I knew David Mayes from the Source magazine and used to play basketball at Chelsea Piers with him and Diddy would be there and Queen Latifah and DJ Clue. And New York was cool as [inaudible 00:19:06] in the 90s, seriously cool. It was really about builders, people who were ambitious in building stuff.

Aaron Dinin:

But it wasn’t just random people building stuff. Correct me if I’m wrong here but from my conversations with a lot of other people in that New York tech community, the early internet wasn’t mainstream at all, certainly not in the way it is today. It was very much counterculture, young people with colored hair and lots of piercings and tattoos, those kinds of things. Could you talk a bit about what the culture of the early tech scene was like?

Jason Calacanis:

It was quite subversive to think that anybody could publish anything and nobody could stop them. And so Mondo 2000, Wired magazine had started to pop up at this time and it was all the intellectuals, John Perry Barlow, Nicholas Negroponte, a lot of the people from the 60s and 70s hippie movements that also were into digital. We all realized the internet was it, all this stuff that had led up to it, the idea that everybody would be online all the time and nobody controlled anything and nobody controlled the internet, was a radical idea. In fact, people said the internet would fail because nobody controlled it. The fact that nobody controlled it meant anybody could do anything and you couldn’t stop them, which again, quite subversive as a concept. And this idea that information wanted to be free was revolutionary. Up until that point in time, every piece of information was locked away somewhere, a library, a college, some course at MIT, some book that was very expensive, some certification or training, some lawyer held the information very close to the vest, the banker. It wasn’t like today where you’re, “I want to learn something.”

You just type it into YouTube and there’s 50 people who will explain how to fix your dishwasher or how to set up your LLC or how to design a logo, all of this stuff was opaque and hidden and protected. And then all of a sudden, information just started to freely flow. And it was [inaudible 00:21:08] to think you could communicate with anybody on the planet at any time and nobody could stop you. Because up until that time, we were told to wait in line. Maybe if you spend 10, 20 years at your career, then you’ll get to maybe get access to the world and maybe you’ll be able to reach other people but everything was gatekeepers. Actually, today we’re trying to reinstate key person control because we feel like this thing’s out of control. But at the time, the concept that you could write a story or start a magazine, suck.com or word.com or feed.com, there was a whole online zine movement.

The fact that you could publish your words and not have to wait at Condé Nast or whatever magazine company or the New York Times and wait five years editing copy and getting people coffee and then you would get read, was just mind blowing for young people. Now today, young people are like, “Well, why would I work for you? I could just start my own TikTok or start my own YouTube. Or if I want to do a job, I just go do it in the world. I don’t need to go work for you. I could if you overpay me and whatever but I’ll just start my own thing.”

The idea that people would start their own thing was just mind blowing at the time, just completely mind blowing.

Aaron Dinin:

And not to be the old guy in the room but I feel like so many young entrepreneurs don’t understand that and why it matters. I’m not saying it matters because the internet used to not be cool and now it is, I’m saying it matters because this is how innovation cycles work. Things that were once subversive and counter-cultural become mainstream. If you want to build something, ‘revolutionary’, then you don’t go and do what everyone else is doing. You find the things with lots of promise that haven’t quite matured into the mainstream. That’s where the opportunity is. You got to be consistently learning and figuring out what’s new, what’s coming down the line in the not too distant future.

Jason Calacanis:

Oh, yeah. Once everybody has the ability to communicate and build any product they want or service, then you are faced with the true reality, can you make something that’s good? And that is really what we’re faced with today in society, is motivation and ability and resiliency, I’d say motivation and resiliency. Most people just are not designed to keep iterating on their previous product and make it slightly better every day in some way, most people just quit. And that’s a problem. The world’s never been more equal, yet people are still complaining, “It feels unfair.”

I couldn’t get into MIT and I used to buy any book I could find or go to any lecture by any MIT professor. And I’m just watching Marvin Minsky’s classes now, they put them up online. I’m watching macroeconomics classes that were taped this year. Every piece of information you could possibly want is already on the internet, YouTube, Wikipedia, wherever. And so then whose fault is it if you don’t have skills, if you don’t create something or build a career? It’s a hundred percent on you. I think it’s a scary thing for people. It’s much easier to blame society or, “I didn’t have access to the information or there were gatekeepers.”

There’s no gatekeepers anymore. If you’re not getting it done, it’s because maybe somebody convinced you that you can’t do it and you believed them. And you should not believe those people. I did it, it’s out there. I don’t think I’m particularly special.

Aaron Dinin:

Sure but to be fair and not to come off as too sycophantic or anything, you did become special for lack of a better phrase, or at the very least you’ve certainly accomplished some special things in your career. Is that fair to say? How would you describe the experience of having built Silicon Alley Reporter and helping cultivate such an impactful tech culture and community?

Jason Calacanis:

I would get all these press clippings and I had a box by my desk, and every time the clippings would come in in the newspaper articles, magazine articles, I’d just throw it into the box. The box would fill up, my assistant would seal it, put it in storage, put another cardboard box in the corner. I had the garbage and the cardboard box. If I liked the story, I’d put in the cardboard box of the archives. If I didn’t like it, I’d put in the garbage. At one point, my assistant came and had framed an article I was in. And I was like, “What are you doing? No, no, no. Once you start framing your articles and putting them on the walls, it’s the end of your career. Take it out of the frame, throw the frame in the garbage, take it home with you and put that in the box.”

And she was like, “I’m really sorry, I thought you’d like it.”

No, I don’t like it at all. I do not want to be Donald Trump looking at a bunch of clips on my wall. Went to Paris Hilton’s house one night, it was a party. She was giving the tour and walking up the stairs to her bedroom and lounge area she had. It was a group of people and just every magazine she’d ever been on the cover of from around the world, all normalized to the same size and the same size frame. It was hundreds. And I was just like, “Well, that’s the end of Paris Hilton’s career.”

Once you start looking at those too much man, that’s the end. Once you start reading the comments, that’s the end of your career.

Aaron Dinin:

And speaking of ends of careers, not that yours ended obviously, but how did your time building Silicon Alley Reporter end?

Jason Calacanis:

The .com crash happened and I wound up selling the remnants of Silicon Alley Reporter, which was Venture Reporter. We had changed the name at the end because all the dot.com companies went away. We just started covering venture capital more acutely and we sold that to Dow Jones. And then they fired me the first week I was there and gave me a two year payout. And so I had a couple hundred grand in Runway, and then I put that all into doing Weblogs, Inc., which became this juggernaut. And 18 months after we started it, we sold it to AOL for 30 million bucks and that was it. And then after that, I went and did another company and became a Sequoia scout and started investing in companies. And then did This Week in Startups podcast and then eventually, All In podcast. And yeah, that’s where I am today, investing a hundred million in startups a year and doing six podcast episodes a week.

Aaron Dinin:

Jason just blasted through a lot of post Silicon Alley Reporter’s significant career milestones in the span of about eh, 30 seconds. Let me see if I can fill in some of those gaps. Weblogs, Inc. was a huge blog network in the early 2000s. It included sites like Joystick and Autoblog and Engadget. The last side is one we heard about in Web Masters episode number 63 with one of its founders, Peter Rojas. He then joined Sequoia Capital and made perhaps his most famous investment, a $25,000 investment in Uber, which went on to be worth over $100 million. He’s also a prominent angel investor, having invested in Robin Hood, Trello and Wealth Front, among many others. And on top of all that, he’s a popular podcast host, most notable his This Week in Startups podcast, which launched back in 2009 and has a bit more traction than Web Masters but we’re getting there.

Anyway, the point is that Jason has done a few things in his career but it all really kicked off with Silicon Alley Reporter. Sure, it wasn’t his biggest success in terms of money but well, is that really the best way to gauge success?

Jason Calacanis:

Well, it’s one scorecard. Yeah. It depends on the industry you’re in, how applicable it is but for me, the memories and the laughs and those collection of memories is more valuable to me than money, for sure. I think life is just a collection of experiences that then get codified into these memories that you can talk about with your friends at two in the morning while you’re drinking some wine or something. And I now optimize my life around creating great memories for me and having great conversations and doing what I love every day, which is hanging out with builders and investing in their companies and doing podcasts. You have to define what success is for you. I think you can make a long list of things you don’t like to do and a list of the few things you do like to do, and if you’re good at it and you like it, that makes it pretty easy.

I think the problem is sometimes people don’t get good at something and/or they don’t like the thing they’re good at. Find something you are really good at, the world needs and you enjoy, you’ll be fine if you draw those circles. The world needs it, you’re good at it and you enjoy it, pretty great. And that’s where I am now at 51 in my life. Love doing podcasts. The world wants them, they make money. I’m good at it. Great, let’s keep going.

Aaron Dinin:

On the topic of collecting memories, I’m sure you got a million of them that are pretty cool in relation to entrepreneurship and the rise of the internet. Any jump to mind, any you could share with us?

Jason Calacanis:

Oh God, so many. Well, I did interview Sergey when Google was only on Yahoo I think, at the time, at one of my events. I did an event with Charlie Rose, I know now he’s got whatever issues. But yeah, interviewing some people with him on stage and being on Charlie Rose. And having the New Yorker article being written by Larissa MacFarquhar and then going and having coffee with Larissa and this other guy, Malcolm Gladwell, who was her friend and we all lived a couple blocks from each other in from Manhattan, hanging out, going to see Chemical Brothers and hanging out with Bjork, whose new album was just coming out, playing basketball with Diddy and hanging out with Jay-Z. The 90s were pretty crazy and rad. Literally, people were like, “Do you miss New York?”

I was like, “I did it like to the nth degree.”

If I went back, the only thing left is to buy the Knicks, which is the only reason I’m working now is to just buy the Knicks, is a 1 or 2% chance I could actually make enough money to make a credible run at buying them, if I work for 10 more years. That’s basically what I’m doing. I really enjoy what I do and it could result in me getting the Knicks. We’ll see, maybe in 10 years you’ll be interviewing me and bought the Knicks. It’s the last goal, last goal on the checklist. But yeah, it was good. Also, being friends with Sam Harris and Elon and helping Sam set up his podcast. I went with Elon to look at the first factory he was going to rent for SpaceX, didn’t have a rocket yet, just hanging out with him and he’s like, “Hey, what do you think of the space at Hawthorn?”

And we just toured it together. It’s cool moments like that. Actually, an even cooler one with Elon was when he got the first Roadster, the P1, we were hanging out in Brentwood driving the P1 and my Corvette on Sunset Boulevard and Robert Scoble made videos of it. It was pretty hilarious. There’s a lot of these great moments and I’m privileged to be around a lot of great entrepreneurs who build great things in the world. It’s been quite a run and I feel like I got another 10, 20, 30 years ahead of me. Hopefully, I survive and can keep having fun.

I would’ve had more fun along the way, that I definitely would’ve done. I had a lot of fun but I would’ve had even more fun, if I’m being honest. There were opportunities to have even more fun. I should have taken them. I got invited to so many cool things. It’s a hard thing. If you’re successful, you have to work, can’t go to every party, especially when they’re around the world and crazy. But yeah, should have gone to earlier Burning Mans than I did. I think my superpower is talking to people and listening and having a conversation. And so once I realized it’s a superpower, it’s nice to do it every day. To me, it’s like going to the gym, it’s like intellectually working out, just having a great conversation. That’s why when you asked and said, “Hey, can I interview?”

I said, “Yeah, it sounds like that’ll be an interesting conversation.”

And here it is, it has turned out to be.

Aaron Dinin:

And selfishly, I’m going to say that’s a great place to end with Jason Calacanis, who’s hung with Diddy and Jay-Z and Elon Musk, saying he had a great conversation with me. More importantly, I had a great conversation with him, and I just want to thank him for taking the time to share his story with all of us. If you enjoyed hearing Jason’s story and want to learn more, as I mentioned, you can of course check out his podcast, “This Week in Startups. Or find him on Twitter, he’s at @Jason. We’re on Twitter too, it’s @WebMastersPod and I’m on Twitter @AaronDinin, that’s A-A-R-O-N-D-I-N-I-N. Give a follow there and/or send any thoughts you have about the episode, you can also find me and lots of my other content about startups and entrepreneurship. It’s all over on my website which is aarondinin.com. Thank you to our audio engineer, Ryan Hanks, for his help pulling together this episode. And thank you to our sponsor, Latona’s, for their support. Remember, if you’re interested in buying or selling an internet business, be sure to visit latons.com.

As we wrap up, I’m going to ask for a quick favor, and that’s to like, rate and/or review Web Masters on your podcasting app of choice. And while you’re there, be sure you subscribe so you get the next episode as soon as it’s released. You can also check out our extensive archives with lots of conversations related to this episode from people in the early New York tech alongside Jason. For example, you might enjoy our episode with Stephanie Simon of Bead magazine, that’s episode 40. Stephanie was hanging out with Jason at some of his parties. Episode number 53 is with Genevieve Field of Nerve magazine. She was also throwing some great New York city parties. And you heard Jason mention the early ad agency called Razorfish. We spoke with one of the Razorfish co-founders, Craig Kanarick in Web Masters episode number 12. It was one of the earliest episodes of Web Masters I recorded and it still one of my favorites.

Actually, who am I kidding? I love all these Web Masters episodes. I hope you do too. I can’t wait to bring another one but for now, I’m sorry to say, it’s time for me to sign off.