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Jason Calacanis: A Case Study in Creating Resources

Jason Calacanis described himself as a serial entrepreneur, angel investor, and podcaster – and someone who had come a long way from the time he had to talk his way into Fordham University. Later, when finances were tight, he talked the dean into getting the bursar to cut him a break. These early experiences with “being bold,” he believed, encouraged him to keep being bold – and creative.

This case study explores Calacanis’ path to entrepreneurship, a route that took him first into publishing, and later into angel investing, then hosting influential incubator and networking events for investors and entrepreneurs. Throughout all of these activities there was a strong creative thread – Calacanis events were not just about connecting investors and entrepreneurs, but also provided entertainment.

Learning Objective

jason calacanis a case study in creating resources

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Jason Calacanis: A Case Study in Creating Resources

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Jeffrey Pfeffer Stanford Graduate School of Business ( OB104-PDF-ENG ) November 11, 2019

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Jason Calacanis described himself as a serial entrepreneur, angel investor, and podcaster - and someone who had come a long way from the time he had to talk his way into Fordham University. Later, wh...

Jason Calacanis: A Case Study in Creating Resources case study written by By Jeffrey Pfeffer has business operations that directly and indirectly are impacted by Russia Ukraine war. Some of the PESTEL Analysis factors that are impacting the Jason Calacanis: A Case Study in Creating Resources business environment are – War in Russia and Ukraine, loss of market opportunities in Russia & Ukraine, increasing wages and risks of stagflation , increasing food and fertilizer prices , high government debts , increasing defence spending , increasing interest rates , increasing credit card default rates and car loan payment defaults , crypto currency frauds and crash ,technological changes such as ChatGPT and AI , financial collapse in emerging markets , big tech shares collapse , and end of an era of easy liquidity Check out more Harvard Business Review Case Studies Solutions

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Ahir Gopaldas and Anton Siebert (2022 July August) "What You’re Getting Wrong About Customer Journeys", Harvard Business Review , 92 Linda A. Hill, Emily Tedards, and Taran Swan (2021) "Drive Innovation with Better Decision-Making", Harvard Business Review 86 Dyer, J. H., & Hatch, N. (2004). Using Supplier Networks to Learn Faster. Sloan Management Review, 45(3), 57–63 Barney, J. B. (1991). Firm resources and sustained competitive advantage. Journal of Management, 17, 99–120 Dyer, J. H., Kale, P., & Singh, H. (2004, July–August). When to ally and when to acquire. Harvard Business Review , 109–115

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Real. intelligent. talk, 100: jason calacanis | advice from the most successful angel investor.

jason calacanis a case study in creating resources

Posted Under: Podcast Episodes

Jason Calacanis ( @Jason ) is Silicon Valley royalty, the most successful angel investor today, and author of Angel: How to Invest in Technology Startups — Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000 .

What We Discuss with Jason Calacanis:

  • What venture capitalists are looking for in startup founders.
  • How Jason bounced back after losing everything (something to which we can personally relate).
  • How to make yourself more marketable , whether you’re a founder or an angel investor yourself.
  • What Jason considers “ the greatest skill of all .”
  • The impersonations Jason can do to make your blood run cold when you’re miles away from any semblance of civilization .
  • And much more…
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Episode 100 of The Jordan Harbinger Show was recorded in front of a live forest audience in the Canadian wilderness at Fireside Conference 2018 . No limbs were frostbitten in the making of this program, though a few poutine may have given their lives for the cause, eh?

Joining us is someone who would spin a good yarn if his own real life tales weren’t fascinating enough to share: far-famed angel investor and author of Angel: How to Invest in Technology Startups — Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000 , Jason Calacanis. Listen, learn, and enjoy!

Please Scroll Down for Featured Resources and Transcript!

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More About This Show

As a young man, Angel: How to Invest in Technology Startups — Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000 author Jason Calacanis resolved to never fail when he saw his father’s business taken away after landing in the crosshairs of the IRS.

Jason waited tables and worked his way through college (at a time when such a thing was possible), eventually finding an opportunity to exercise his computer skills and gain traction as the nascent World Wide Web was taking its first baby steps. He founded the Silicon Alley Reporter in 1996 and the future seemed bright — so bright that he turned down a buyout offer for $20 million.

“And then the dotcom crash happened,” says Jason. “And the Internet went from being the hottest thing in the world to being a bunch of charlatans and con artists. And I had to have a really deep look in the mirror and say, ‘Am I a charlatan? Is this real? What just happened?'”

Most of his magazine’s advertisers went out of business overnight. His regulars couldn’t take out any more ads, and there wasn’t any money to pay for ads that had already run.

“We went literally from $12 million revenue in one year to $500,000 the next. It was really brutal. I had to lay off 80 people; people cried. It was a really trying experience and I just thought to myself…’I promised myself I would never fail. And now I am on the precipice of failure because the stock market crashed.'”

Listen to this landmark 100th episode in its entirety to learn what Jason did next to resurrect from the failure he promised himself he’d never endure, the authenticity of blogging in the early 2000s that appealed to Jason and set him up for his next business venture, what it was like to go from being $10,000 in debt to never having to worry about money again, why Jason prefers to work as an angel investor rather than at the venture capitalist level, why businesses really fail, the lists Jason makes to weigh the pros and cons of a pitch, why most people are risk-averse (even when the rewards far outweigh the risks), why Jason believes the ideal startup founder is someone who is delusional — but has skill, four must-ask questions Jason puts to founders, and much more. Make sure to stick around for the Q&A at the end!


If you enjoyed this session with Jason Calacanis, let him know by clicking on the link below and sending him a quick shout out at Twitter:

Click here to thank Jason Calacanis at Twitter!

Click here to let Jordan know about your number one takeaway from this episode!

And if you want us to answer your questions on one of our upcoming weekly Feedback Friday episodes, drop us a line at [email protected] .

Resources from This Episode:

  • Angel: How to Invest in Technology Startups — Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000 by Jason Calacanis
  • This Week In Startups
  • Jason Calacanis’ website
  • Jason Calacanis at Twitter
  • Silicon Alley Reporter
  • Xeni Jardin at BoingBoing
  • Paidcontent.org
  • Nick Denton
  • Peter Rojas
  • Bob Dylan Vocal Samples
  • At What Price Happiness? $75,000 by Courtney Rubin, Inc.
  • The Big Game Show: Jason Calacanis vs Daniel Negreanu
  • The PokerStars Big Game: Jason Calacanis vs. Doyle Brunson
  • Bitcoin Bloodbath Nears Levels of Dot-com Bust; Many Tokens Go to Zero by Bloomberg, Los Angeles Times
  • Jeffrey Dahmer’s Inferno by Brian Masters, Vanity Fair
  • Joe Rogan Experience #1169: Elon Musk
  • Ratatouille
  • Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration by Ed Catmull and Amy Wallace
  • Movie Reviews and Ratings by Film Critic Roger Ebert
  • Farewell Walt Mossberg, the Scourge of Silicon Valley by John Naughton, The Guardian
  • Early Uber Investors Slam Travis Kalanick by Maya Kosoff, Vanity Fair Hive
  • A Eulogy For Craigslist’s ‘Casual Encounters,’ And All The Sex I Found There by Emily McCombs, HuffPost
  • Why I (We?) Invested $378,000 in Calm.com by Jason Calacanis, LinkedIn
  • SendGrid Startup of the Week #2 – Alex Tew of Calm.com
  • The Million Dollar Homepage
  • Phil Jackson On Using Meditation And Mindfulness To Create Great Basketball Teams by Lisa Capretto, HuffPost
  • The Mirror of Mindfulness: Two Guided Meditations by Sam Harris
  • Jason’s Private Syndicate
  • Tim Hortons
  • The 22 Key Turning Points In The History Of YouTube by Megan Rose Dickey, Business Insider
  • Japanese Style Iced Coffee Puts Cold Brew Coffee to Shame by Leanne Butkovic
  • Dollar Shave Club
  • Steve Jobs: The Greatest Second & Third Acts in Business History by Christina Warren, Mashable
  • Why Jeff Bezos Doesn’t Mind Hiring People Who Are ‘a Little Bit Annoying’ by Ruth Umoh, CNBC
  • Working at Netflix , Glassdoor
  • Mahalo.com: Pivot or Die by Adam L. Penenberg, Fast Company
  • Jason Calacanis Relaunches Inside Again — This Time as a Newsletter Company by Peter Kafka, Recode
  • Chamath Palihapitiya
  • Podcasting Historical Timeline and Milestones , International Podcast Day
  • Neumann Microphones
  • Shure Microphones

Transcript for Jason Calacanis | Advice from the Most Successful Angel Investor (Episode 100)

Jordan Harbinger: [00:00:00] Welcome to the show. I'm Jordan Harbinger. As always, I'm here with my producer, Jason DeFillippo. It's episode 100. All right, we made it this far. What do you think, Jason?

Jason DeFillippo: [00:00:09] Amazing. It's been a long ride so far.

Jordan Harbinger: [00:00:13] It has. It's been a long ride. It's been an interesting new beginning. I personally kind of feel better than ever, but we still have a long way to go. That's where I'm at with it.

Jason DeFillippo: [00:00:23] Well, there is no end to this. That's how podcasting works. We go until we're dead.

Jordan Harbinger: [00:00:27] That's right. That's right. All right, so episode 100. We ran this one live in front of a crowd and a live studio audience or not studio added live forest audience at Fireside in Canada. Jason Calacanis is one of the best known angel investors. He was one of the first investors in Uber. He sold one of the first blogging networks to AOL and is generally considered Silicon Valley Royalty. He's also the author of a book called Angel: How to Invest in Technology Startups-Timeless Advice from an Angel Investor Who Turned $100,000 Into $100,000,000, and I think he's way over that now, of course. But I highly recommend that book if you're an angel investor and/or if you're a startup founder who may eventually look for funding, but even if you're not, there's plenty in here for everyone else as well. Today, we'll discover what venture capitalists are looking for in start-up founders. We'll explore how Jason came back after losing everything, a story that's pretty near and dear to us on the show these days, and how to make yourself more marketable, whether you're a founder or an angel investor yourself.

[00:01:31] I highly recommend some of the teaching from this episode, even if you're not in business for yourself or investing in others. It's a great rags to riches story that's very frank and funny in its delivery. We had a lot of fun doing this. Again, we ran this in front of a live audience in the middle of the woods at Fireside Canada. So if you hear an ATV or an owl or just some drunk audience members having a great time, know that it's not a sound effect. We all actually had a great time and at the end of this episode we've also got some audience Q&A. So if you're into these topics, make sure you stick around for that special thanks to Fireside Canada for making this happen. Of course, we have worksheets for this episode as we always do, to make sure you solidify your understanding of the key takeaways here from Jason Calacanis. That link is in the show notes at jordanharbinger.com/podcast.

[00:02:19] And if you want to know how I book all these great people manage all these amazing relationships, well, I use systems, I use tiny habits and I only use a few minutes per day because ain't nobody got time to spend all their time emailing, calling and writing people. I'm teaching you how to do this for free. Check out our Six-Minute Networking course over at jordanharbinger.com/course.

[00:02:40] Now here's Jason Calacanis. So how long have you been an undercover police officer?

Jason Calacanis: [00:02:45] I took the police officer tasks when I was 18 with my brother Josh and a we both passed, and I was going to go into the police Academy with them in New York city. I decided to go to night school and fix laser during the day, and I graduated and I thought I want to be in the FBI and so I was going to go for my masters in criminal justice at John Jay and I had the FBI application and then I saw the Internet and I was like, “That's going to be fucking huge. I want to do that.”

Jordan Harbinger: [00:03:13] Yeah, so little did you know.

Jason Calacanis: [00:03:15] Right now I would be Clarice Starling in The Silence of the Lambs.

Jordan Harbinger: [00:03:19] Puts the lotion in the basket. You also see how much those guys make, unfortunately?

Jason Calacanis: [00:03:24] Unfortunately. Clarice, who is this man you seek? What does he covet?

Jordan Harbinger: [00:03:29] That adds to your creep factor? Big time.

Jason DeFillippo: [00:03:32] Have the lamb stop crying.

Jordan Harbinger: [00:03:34] But your dad actually had a run in with the feds when you were younger. That kind of did that turn you off from law enforcement?

Jason Calacanis: [00:03:39] Well, all my friends I grew up with are cops or firemen, and I could tell you a hundred different insane stories.

Jordan Harbinger: [00:03:46] But your dad owned a bar and one day.

Jason Calacanis: [00:03:49] Are we starting?

Jason Calacanis: [00:03:50] Yeah, this is it, man.

Jason Calacanis: [00:03:50] Oh, okay, sorry.

Jordan Harbinger: [00:03:51] Remember that time when I was like “Hey, hit record.”

Jason Calacanis: [00:03:52] I thought we were talking to bring everybody over here.

Jordan Harbinger: [00:03:54] Yeah, no, we're doing it.

Jason Calacanis: [00:03:55] Okay. It's on, okay.

Jordan Harbinger: [00:03:56] No warnings.

Jason Calacanis: [00:03:57] We'll get you to intro, are you the intro the show?

Jordan Harbinger: [00:03:58] Nope.

Jason Calacanis: [00:03:58] You just start?

Jordan Harbinger: [0:03:59] I do it later. Yeah, when you're not, I want to spare you that time.

Jason Calacanis: [00:04:02] That time, okay.

Jordan Harbinger: [00:04:03] Yeah.

Jason Calacanis: [00:04:03] Hey, well thanks for having me.

Jordan Harbinger: [00:04:04] You're welcome.

Jason Calacanis: [00:04:05] Okay.

Jordan Harbinger: [00:04:06] So anyway, back to your dad getting almost arrested by the feds while you were at home. Because I wonder when you told that story in the book Angel , which is available here, if you ask a good question and not available, if you ask a bad question after this. You tell that story where you're just sitting at home one day and it's like you get raided by the FBI. I'm surprised that that made you want to maybe join them later.

Jason Calacanis: [00:04:27] Yeah, that's a paging Dr. Freud. Well when I was a kid, my dad was an entrepreneur, and obviously, I looked up to him a lot and if you find any entrepreneur you can point to a pretty interesting relationship with their father in almost every case. And so I had a complicated relationship with my dad. It's good now. But in 1987, the stock market crashed, and I was 16 or 17 years old. I was about to go to school and the feds came, taxes. My dad didn't pay his taxes for a little while. The feds don't take kindly to that. And so they took his bar with shotguns and everything, locked it up. And my dad, who was kind of broken at that point and just said to me, “I'm sorry son, I don't have any money for college.” I said, “Okay.” So then I just went to school and I said, “Can I join the night program?” And they were like, “Okay.” So I switched to the night program, and I was 18 years old going to school with the continuing education. Folks, I was in school with 30 and 40 year olds, and I worked during the day at three different jobs, fixing laser printers, a barback, which has anybody ever been a barback or know what that is? Who knows what a barback is? So who's ever done it? Raise your hand if you'd been a barback. It's the worst job in the world. Your job is to do all the shit that bartenders don't want to do and get paid 10 percent of the cup at the end of the night, the tips. So basically you spend your life carrying boxes of beer, and I used to put two buckets of ice on either side, which is how I got this incredible physique, 20 years later. But I would just be carrying ice and then you got to take these cores lights and put them in the ice and your hands are ripped up and back then people were allowed to smoke in restaurants and bars. And so you get home and you're just like, “Oh my God!” You just have this like layer of sweat and smoke on you. It's just horrible.

Jordan Harbinger: [00:06:08] It's like what we all had this morning after the campfire.

Jason Calacanis: [00:06:10] It was very similar to that actually. But that was a big defining experience for me because I said to myself, “I will never fail.”

Jordan Harbinger: [00:06:16] You will never fail.

Jason Calacanis: [00:06:18] Fail, because I saw my dad failing. I said, “I'm going to avoid that,” and then fast forward it was 1999, 2000, I'm on top of the world. I've got the Silicon Alley Reporter magazine, which was my first.

Jordan Harbinger: [00:06:27] Really? Did you see your dad as a failed business owner or entrepreneur?

Jason Calacanis: [00:06:32] Yeah. I think when the feds come and take your business and you almost go to jail and you have a $100,000 tax bill, that would be pretty clearly defined as failure.

Jordan Harbinger: [00:06:39] Perspective. I agree with you, but some people might not agree with you.

Jason Calacanis: [00:06:42] But I mean looking back on it. At the time I wasn't, it wasn't like at the time I was mad about it or resentful, it was more like being in shock. You know, when you're 17 years old and you’ve see something traumatic like that happen, it's kind of like getting just punched in the face. You don't feel the pain at first. You're just looking at the ceiling going, what just happened? Anybody ever get punched in the face and get knocked out? Keep your hand up if you got knocked out.

Jordan Harbinger: [00:07:05] If not stick around after the show.

Jason Calacanis: [00:07:07] If you haven't been knocked out yet, look at the person next to you and punch him square in the face. It's literally, I've been knocked out in my lab, I've been punched a couple of times, and I grew up in Brooklyn, like it's part of growing up in Brooklyn.

Jordan Harbinger: [00:07:18] And what happened to your accent though?

Jason Calacanis: [00:07:20] It comes out when I'm mad.

Jordan Harbinger: [00:07:23] Again, stick around for the rest of the show, so you will know.

Jason Calacanis: [00:07:25] Or if I drink it comes out. But fast forward and I had the Silicon Alley Reporter. I'm on top of the world. I'm 29 years old. I've got a hundred people working for me. We were doing 12 and half million dollars in business or so. And I was covered in the New Yorker in a five or 6,000 word profile. I'm on Charlie Rose. I'm on 60 Minutes. I was on Bloomberg twice a week. And so I'm like, “Wow! I'm on top of the world and I'm unstoppable.” And somebody offered me $20 million for the magazine. And I was like, “Fuck you! I'm taking this to the moon.” And then the dotcom crash happens.

Jordan Harbinger: [ 00:07:57] It's on the moon where all the magazines are now.

Jason Calacanis: [00:07:59] Exactly. And he's good, he's good. And so then the stock market crashes and if, and the Internet went from being like the hottest thing in the world to being a bunch of charlatans and con artists. And I had to have like a really deep look in the mirror and say, “Am I a charlatans, or Is this real? What just happened?” And again, it's like getting punched in the face. So I'm sitting there going, “Oh my God! All the advertisers, literally overnight when out of business or if they were in business, I called them. And said, “You owe me 50 grand in ads,” and they're like, “We have no money Jason. We're just laying everybody off.” And I'm like, “Okay.” And we went literally from $12 million in revenue one year to 500,000 the next, I mean this was the--

Jordan Harbinger: [00:08:42] And this is gross? This is not like what you had left after paying everyone.

Jason Calacanis: [00:08:45] No, I mean, and so it was really brutal. And so I had to lay off like 80 people and people cried. It was like a really trying experience and I just thought to myself, “Fuck, I promised myself I would never fail.” And now I am about, I'm on the precipice of failure because the stock market crashed.

Jordan Harbinger: [00:09:05] Was that what you were thinking at the time though?

Jason Calacanis: [00:09:07] Exactly. It literally hit me like one day I was like, “Oh my God, my dad got hit by the stock market crash.” All the people who owed him money who had tabs at the bar didn't pay them. And all of the people who owed me money for ads are not paying me. It was like literally some kind of Shakespearian--

Jordan Harbinger: [00:09:23] You're like, “ I'm a bar owner at [indiscernible][00:09:26].”

Jason Calacanis: [ 00:09:26] And nobody would pay, exactly. And I'm just like, “Ah, fuck.” And then I said, “You know what? I didn't get here by accident. I did something. I created this magazine off my credit cards. I built it, I have talent.” And I remembered that two or three of my employees had left to do weblogs, blogs, and I was talking to one of the Xeni Jardin who was working at BoingBoing. You can give it a clap. You have it snap and get some snaps here if you like it. Okay, good. We'll snap it up. It's like a jazz club. And she was making a ton of money, I think they were chopping up like six or $7,000 a month each with the four or five partners. And then Rafat Ali who worked for me, I pay content. He came to me one day, this is before the magazine had crashed and he said, “I heard that you found out about paycontent.org, are you going to fire me?” And I said, “Rafat sit down, son. Let me explain something to you.” You need an editor and in a blog you have no editor. Blogs are childish and stupid and you used dotorg, it's not even dotcom. You can keep doing your blog on the weekends. I don't care, but honestly it's a complete and utter waste of time.” And then I saw Nick Denton, a friend of mine had created Gawker and I was like, “Wait a second.” Three of the people I really respect, two of which worked for me are now making five grand, six grand, seven grand a month. This blogging thing has legs, and it turns out certain people do need to have their work edited, but the most elite people like, Om Malik or Peter Rojas, they're doing better work if they're not edited. And so I said, “Oh, I'm wrong.”

Jordan Harbinger: [00:11:19] Why is that? Speed?

Jason Calacanis: [00:11:21] It's speed. And then the people who were managers in between them would fuck up their work.

Jordan Harbinger: [00:11:25] Sure.

Jason Calacanis: [00:11:26] By editing it or taking out the edges and it was better to be more authentic. It's like, “Yeah, Bob Dylan gets up here. He takes out his guitar, he plays a song.” And then you put him through a studio and you have somebody like auto tuned his voice. It's like it kills it, right? So that's what people were doing. They were taking raw talent and they were muting them and saying, “Don't say that, this is a little too rough, too opinionated.” And what was refreshing about blogs in the 2000s was that you had this like honesty and authenticity that came out. So I was like, “That's going to be a thing.” So I Built Weblogs Inc., and 18 months after we were growing it, we were at about 150K in total revenue, and AOL came and offered us 30 million bucks for it. And unlike the time when Alan Meckler offered me $20,000 for Silicon Reporter, I said, “I'll take it.”

Jordan Harbinger: [00:12:13] You said $20,00.

Jason Calacanis: [00:12:14] 20 million.

Jordan Harbinger : [00:12:16] Oh, I heard $20,000.

Jason Calacanis: [00:12:17] Alan Meckler offered me for $20 million for Silicon Alley Reporter, and I didn't take it. And I was like, “You know what? I was negative 10,000 in my bank account and I was walking my old dog, Toro, rest in peace, and spoken to cigar with my wife and we were sitting there in Santa Monica, we had a $2,000 a month apartment. And I said, “They offered us $30 million, and I can't keep up with our credit card bills. I'm going to take it.” And she was like, “This is going to be crazy. Like we're going to have over $10 million in our bank account.” I was like, “Yep.” And I sat there and I just had to have this like really long look on like deep moment because I had a very complicated relationship with money and being poor because my parents, every fight they ever had in their life was over money about money.

Jordan Harbinger: [00:13:06] Is about money, right. You grew up wanting to be rich.

Jason Calacanis: [00:13:08] Exactly. And I want it to be powerful and rich when I was a kid, and looking back on it, the reason I wanted to be powerful in riches was because I was poor and I had no power. And it was very complicated for me, and then the money transferred and my wife remembers a story and I remember like it was yesterday. I was sitting there refreshing my Bank of America account, the corporate account and nothing, nothing, nothing. And then boom, 27 million bucks and I start crying.

Jordan Harbinger: [00:13:33] Sure.

Jason Calacanis: [00:13:34] And I started crying.

Jordan Harbinger: [00:13:36] Sure.

Jason Calacanis: [00:13:36] And my wife’s crying too. I don't have to worry about money ever again.

Jordan Harbinger: [00:13:40] Ever. You'd never have to worry.

Jason Calacanis: [00:13:41] And it was so scary for me to be poor for so long, that I just had this incredible cathartic release. And then I went to Silicon Valley and when I started making noise up there, all these, I'm obnoxious, rich people were like, “I'm not in it for the money, I do venture capital because I'm passionate about changing the world.” I was like, “Fuck you! You have all the money. That's why you're saying it's not about the money. If it wasn't about the money, why are you raising these huge funds and taking these huge management fees? And it's obviously this is all about the money.”

Jordan Harbinger: [00:14:12] But that's not cool to say. You want to be a little bit.

Jason Calacanis: [00:14:14] Everybody's a pretentious asshole and like, “Oh, it's not about the money.”

Jordan Harbinger: [00:14:18] Present company excluded, of course.

Jason Calacanis: [00:14:19] It’s obviously about the money. Like I call it money, like you need it to do things and so it's not the be all end all. But I had a very complicated relationship where, and when you make your first 10 million, it takes the edge off. Of course, I know it's obnoxious to say, but I can say without being obnoxious, I hope because I spent the majority of my life broke.

Jordan Harbinger: [00:14:40] How much of that is an understatement? This is taking the edge off $20 million is not taking the edge off. That's real money. You never have to work again. You never do anything that other people don't want you to do. Ever.

Jason Calacanis: [00:14:50] Yeah. It will fuck with your mind a bit if you're don't have a stable foundation. I feel lucky because I grew up with a very stable foundation and I've never really cared about the money in the sense of making a lot of it. What I cared about was not being poor. And then if you look at the psychological studies, they say once people get there like, “Oh, money can't buy happiness.” I'm like, all the statistical studies are like “Poor people are really fucking unhappy.” It's like, “Oh, shocking!” Really? It’s sucks to be poor.

Jordan Harbinger: [00:15:19] I have to like 100,000.

Jason Calacanis: [00:15:20] And it's like the number was 70,000, and I don't know if you know, obviously by region it's going to be different, but when people get past $70,000 a year in income, they don't have this underlying anxiety.

Jordan Harbinger: [00:15:32] Right. It starts to what does that exponentially taper off level of happiness?

Jason Calacanis: [00:15:36] Of course, yeah. Because the truth is like I have four Teslas, I drive one at a time. I can't drive four Teslas at once.

Jordan Harbinger: [00:15:44] Not yet.

Jason Calacanis: [00:15:44] And nor does it matter? And by the way, the one I drive is the cheapest one, the model three, because it's the best one paradoxically. And if we all eat a hamburger and Mark Cuban was here and Elon was here and I'm here and you're here and it's the same hamburger and we all enjoy it equally. So 99 percent of the best things in life really are not correlated with capital. It's when you don't have it and you have that underlying fear and you can't take chances. And that's really where entrepreneurship comes in.

[00:16:11] The reason why I'm so passionate about being an angel investor and not like a VC, because I've been offered to work at call it six of the top 10 venture capital firms have offered me jobs or tried to recruit me. I like to work in the angel stage because as you saw when we were doing the interaction, when I meet somebody like Janell and I see winner, winner, winner, and I'm like, “Oh, that's exciting to me. Like I know that person's going to win at something,” and I need to be in business with them and I want to win with them. So I had to like you know, you take stock of your life at different points, like when you fuck up or when you win, and I took stock of my life a couple of times in the past couple of years. And I was like, “What do I love doing?” “I like winning and I like supporting people who are changing the world.” “Okay, what's the best way to do that?” “Being an angel investor.” And so now I've just organized my life around this premise of meeting founders, trying to figure out which ones are under recognized and being the person who writes the first check or the check when nobody else believes in them because it's the most exciting check to write. And it's the smallest check, 25K, 250K a million compared to what my contemporaries do, which is write $25 million checks or $2.5 million checks. But I find it super exciting. I love the fact that I was the third investor in Uber or the second investor in Thumbtack. That to me, is the exciting moment to believe in it when nobody else does.

Jordan Harbinger: [00:17:35] Do you get more excited about people or businesses?

Jason Calacanis: [00:17:40] Obviously people.

Jordan Harbinger: [00:17:41] I mean it's not necessarily obvious though, because a lot of people think they have to have an Uber on their hands in order to get your attention.

Jason Calacanis: [00:17:46] You know, here's the thing. In hindsight, everybody will believe in something that's changed the world. It's pretty obvious, like what people are very bad at is believing in something before it's changed the world. And so you have to change your thinking as an investor. What I think the reason I became very good at this is because of the fact that I'm a compulsive gambler. And as anybody knows who types Calacanis, Daniel Negreanu into YouTube and watched me play $130,000 hand with the world's best reader, I'd beat him.

Jordan Harbinger: [00:18:28] No big deal.

Jason Calacanis: [00:18:28] No big deal.

Jordan Harbinger: [00:18:29] No.

Jason Calacanis: [00:18:29] No big deal, okay? I'll try not to drop into trunk.

Jordan Harbinger: [00:18:33]  That story would never have gotten until it if you lost that hand.

Jason Calacanis: [00:18:36] No.

Jordan Harbinger: [00:18:36] Not ever.

Jason Calacanis: [00:18:37] I lost $100,000 a hand with pocket Kings versus Doyle Brunson. And that was painful.

Jordan Harbinger: [00:18:42] Not bitter about it at all.

Jason Calacanis: [00:18:44] I’m not bitter at all. What are we talking about? Gambling.

Jordan Harbinger: [00:18:47] Definitely not that handy laws.

Jason Calacanis: [00:18:49] Definitely not.

Jordan Harbinger: [00:18:50] That’s in the past.

Jason Calacanis: [00:18:51] Definitely not the fourth edible that somebody just shoved down my throat over here.

Jordan Harbinger: [00:18:54] I was wondering though if you bet on more about people or businesses, you are going that [indiscernible] [00:18:59]

Jason Calacanis: [00:18:59] So here's where I was going with that. You have to bet on people and because even an entrepreneur who maybe builds the wrong product in the wrong market, they'll be smart enough and indefatigable enough, resilient enough to realize, “Oh, this didn't work.” “Hey, let's make a couple of little adjustments, maybe a full pivot and they'll figure it out.” Now yeah, once in a while a dipshit team of idiots will be at the right place and the right time. Cryptocurrency.

Jordan Harbinger: [00:19:30] For example.

Jason Calacanis: [00:19:31] Sorry. No offense to the crypto people, but there are some stupid people who just took down large sums of money. That's not the likely scenario most of the time. And you better put that--

Jordan Harbinger: [00:19:44] Not Pointe Smart who sponsored this conference though? That is not the case with it.

Jason Calacanis: [00:19:48] 1,999 of these ICOs are complete, utter bullshit, but that one is the winner.

Jordan Harbinger: [00:19:54] Yes.

Jason Calacanis: [00:19:56] Thank you for sponsoring the event. No.

Jordan Harbinger: [00:19:57] Your check has cleared, going smart.

Jason Calacanis: [00:19:58] Crypto is fascinating. We'll get into it. But that is like an outlier. So you have to look at the founder and you have to ask, “Is this person a winner? Are they going to win at life? Are they indefatigable? Will they give up or not?” Because the reason businesses fail is not because they run out of money. That's what most people think is the reason they fail. It's because the founder gives up. I've seen many founders run out of capital and run on fumes for a month or two. Tell everybody they're not getting paid. Tell everybody to take side jobs. And then all of a sudden they raised the money six weeks later or 12 weeks later and the business is still going. So I just look for those people. And sure, it helps if they're in a great market, but here's the thing that the really outlying successes in our business are the ones that define the market. So marketplaces and on demand didn't exist as terms when we invested in Uber or other people invested in Airbnb. And I looked at Airbnb and I didn't have a chance to invest, but when I first heard it, I just thought, this is the stupidest idea I've ever heard.

Jordan Harbinger: [00:21:00] We’re once cold cereal in someone else's couch.

Jason Calacanis: [00:21:03] Well they were like, “Yeah, well here's how it works.” Somebody was explaining it to me who had invested and they're like, “Okay, it's like couchsurfing so people have an extra room and you're going to Tokyo, you stay on their couch, and I'm like, “Like a serial killers couch?” I give this serial killer 50 bucks, I stay on their couch and then I wake up and they're over me with a knife. And I'm like, “That's fucking crazy!”

Jordan Harbinger: [00:21:21] He doesn’t want you to wake up.

Jason Calacanis: [00:21:21] Well no, they have a reputation system. And I was like, “Oh, a sociopathic serial killer is not going to be able to game wreck the reputation.” Like that's kind of what they do is they kind of, I mean Jeffrey Dahmer, like he's pretty good at getting people to come to his house and eat him. And then they were like.

Jordan Harbinger: [ 00:21:37] Not anymore though.

Jason Calacanis: [00:21:37] Not anymore. They caught him eventually. But then on the other side, they're like, “Well, don't worry, you can host somebody and make money.” And I'm like, “So I could host a serial killer in my house who when I'm asleep, will then break into my master bedroom and kill me.”

Jordan Harbinger: [00:21:47]  Somebody who grew up in Brooklyn, all right.

Jason Calacanis: [00:21:49] Right. But I had trust issues with that and I was like, “This is crazy.” But what I didn't realize was what the founders realized, which was there was a group of people who this was appealing too, and it would expand. So I'm going to Tokyo because the book is just been translated on Friday. I'm like, “Oh wow! There's a nine bedroom modern home in Tokyo that I could rent and bring my entire team and it's 1,000 bucks a night.” Wow! That's like 100 bucks a room. This is incredible deal. And I'm like considering using Airbnb, so where people start and where they end, and you have to suspend disbelief. And the way you can do that is you just make a long list of all the reasons why the startup will fail. So for the startups we still have today, I could give you the list of what VCs will say or the reason it's going to fail. And then you make a list of the reasons why it's going to succeed. And that might be a very short list. It's always shorter than a list of reasons it will fail. And then you take the list of the reasons it's going to fail and you rip it up and you throw it away and say, “I believe in that person to go down that list and crush those issues.” And here's what Michael write, and if it's a one in a hundred chance but it pays off a thousand to one, you would take that.

Jason DeFillippo: [00:22:54] You're listening to the Jordan Harbinger Show with our guest, Jason Calacanis here on episode 100. We'll be right back after this.

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[00:24:36] Support for the Jordan Harbinger Show comes from our friends at Rocket Mortgage by Quicken Loans, America's premier home purchase lender.

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Jason Calacanis: [00:26:17] And if it's a one in a hundred chance but it pays off a thousand to one, you would take that, and that's where gambling comes in. I got into poker and I became a good poker player after years, and it takes a long time. But what you realize in poker is something called implied odds. So you and I are in a hand, and we're playing very deep stacks. We’ve got $50,000 in front of us each and I've got seven, eight, and you've got aces. Should I pay $1,000 with seven, eight? Well, that doesn't seem logical, but if I hit my straight, you're never going to see it coming, and you might shove your whole fucking stack in there, and that's the implied odds. So if I took a deck of cards out and I asked somebody in the audience, you give me $1,000, and if you pull the ace of spades, I'll give you 100,000. Most people would be like, “Well that's stupid.” There's only one ace of spades. But then if you realize it's one out of 52 which is about a 2 percent chance. You'd say, “How many times can we do this bet?” Can we do it a hundred? Can we do it a thousand? Because I am going to win in the long run. Our minds are not designed for that. Evolution has made us conservative, scared little creatures because if this was prehistoric times that we were going to go across that river, you'd be like, fuck, we don't know what's in the water. It can be an alligator. I'm not going across the river, but on the other side of the river, it might be all the apples, and somebody took the chance and went over there. With startups, it's not life and death anymore, so you should take the risk, but people's brains are wired. We're all still wired to be scared little monkeys, of we're just terrified of taking risks. You have to rewire your brain to be a great investor and to be a great founder and say, “Fuck it! I'm taking the risk.” It's a 1 percent chance, but it's a 1 percent chance at making $1 billion or changing the world. Those ate calculated risks that are worth taking, but your brain has a very hard time with making them. That's why East Coast VCs are so bad at the game and West Coast VCs are so good at it.

Jordan Harbinger: [00:28:08] Burn.

Jason Calacanis: [00:28:09] East Coast feast. Well, listen, East Coast has better rap music. Biggie forever. Jay-Z. West coast, some good stuff out there, but it's nowhere near East Coast rap. But on the VC side--

Jordan Harbinger: [00:28:19] Nicely done.

Jason Calacanis: [00:28:20] What happens? Yeah, I mean, Snoop Dogg, Biggie, Jay-Z like no comparison.

Jordan Harbinger: [00:28:27] This went down, this took a dark turn.

Jason Calacanis: [00:28:30] But anyway, someone's going to get shot.

Jordan Harbinger: [00:28:32] Yeah, I'm not it.

Jason Calacanis: [00:28:34] But the VC's on the East Coast have never hit $100 billion company. The VCs on the East Coast generally don't ha haven't had these kinds of crazy success, nor do they know people have had crazy success. On the West Coast, people were like, “That's a fucking crazy idea. Let's do it.” And on East Coast they’re like, “That's a crazy idea. Can I have a 6X liquidation preference and I want to have a two board seats and you get one, and they're just playing because they're scared.

Jordan Harbinger: [00:28:57] And your slides need work.

Jason Calacanis: [00:28:59] Yeah, and your slides. Well, it’s bullshit! If you're a VC, it's just supposed to take risk. You're supposed to take crazy bets, so anyway.

Jordan Harbinger: [00:29:08] Well, you mentioned the number one reason startups fail is not funding, et cetera. So that the founder gives up. How do you know? Of course you don't advance. What are you looking for to find a founder who might give up? So if we're sitting here in front of all these people, what do you look for that guy, she is going to give up, he's going to give up. What are you looking for or what is it in their office that you see?

Jason Calacanis: [00:29:30] The look in their eyes.

Jordan Harbinger: [00:29:31]Oh, come on, Todd! There’s more to that.

Jason Calacanis: [00:29:32] While they talk. It may seem like that I'm bullshitting right now, but I look in people's eyes and while they're talking, I can tell, it might be poker if they actually believe what they're saying.

Jordan Harbinger: [00:29:43] Okay, so if they're full of crap, fine. They'll probably give up.

Jason Calacanis: [00:29:46] Yeah, and I'm looking for somebody who's delusional with skill.

Jordan Harbinger: [00:29:52] That's what you want?

Jason Calacanis: [00:29:53] Yeah.

Jordan Harbinger: [00:29:54] You want delusional with skill.

Jason Calacanis: [00:29:55] Absolutely, like I am going to create a rocket ship company, like “Really?” Tell me more. “Well, I'm going to Russia, and I'm going to look at how they make rockets and then I'll come back and make my own.” And when I heard -- I knew Elon before SpaceX and before Tesla, when I heard him talk about it, it was very clear to me that he's indefatigable, he doesn't get tired, he's got the stamina of a hundred people, and he's going to win because he'll never give up. And if you look like the shorts are like 30 percent of the stock available to be shorted, has been shorted, and they are spreading false information and attacking him while he's standing in front of a huge dam, trying to hold back global warming.

Jordan Harbinger: [00:30:42] With a joint in his mouth apparently.

Jason Calacanis: [00:30:43] Whatever. I mean there's --

Jordan Harbinger: [00:30:44]  Yeah, I mean.

Jason Calacanis: [00:30:44] I mean it's about eight people that join in their mouth out here who gives a shit? I'm like --

Jordan Harbinger: [00:30:49] Who's got a joint for Jason?

Jason Calacanis: [00:30:50] Actually, I kind of feel--

Jordan Harbinger: [00:30:52] I kind of feeling for a joint right now, aren't you?

Jason Calacanis: [00:30:53] Kind of feel like we need to, Joe Rogan this right now.

Jordan Harbinger: [00:30:55] I mean look, half of these people came from a joint rolling workshop earlier today. I'm just saying, I'm drinking a beer. You got coffee, that’s all I’m saying.

Jason Calacanis: [00:31:03] I taught the advanced class for the people in the advanced class, very well done. I taught everybody in the advanced path. I taught -- Yes, he was my top students and I taught him how to do it with one hand. That's was good. You got that? You put the wrist into it. I'm actually, I'm kind of stoked if Elon smoking a little weed because it gets calmed down a little bit and get some sleep. Putting that aside, you're going to face a lot of criticism and hate if you want to change the world or do great things, sometimes from the people closest to you. And you'll have to learn that there are like different categories of people in the world. There's people who change the world and do interesting things, and then there's the people who criticize them. Anybody that's ever seen the movie Ratatouille? Who seen Ratatouille? So Anton Ego, who is the famous a reviewer, at the end of the movie, he says, “You know, the life of the critic is pretty meaningless at the end of the day. But the one thing the critic can do is support the new.” And he has this incredible realization that not everybody can be a great chef, but a great chef can come from anywhere. And that's the rat, Ratatouille. And he realizes that when he eats that incredible Ratatouille that reminds him of his mother's and the tear comes down, it's like the greatest scene in any Pixar film ever. And when I talked to Ed Catmull from Pixar on my podcast, the guy who wrote the book Creativity . I was like, “Is that a fuck you from Pixar and Steve Jobs to the critics?” He said, “Yep.” Great. Next question. And which have to realize is like the critics achieved nothing in their lives. Like who's your favorite critic? Yell out their name. Okay. Ebert, right, yeah. And the reason we loved Ebert was because he was a fucking fan of film and he loved it, and he loved people who took risks, and he loved the new. And I know this because when I was coming up, when we were doing Weblogs Inc, we started blogging Sundance. I went to Sundance. I scam my way into getting a press pass and I would go and I was like, “Oh my God! There's Roger Ebert hanging out the yarrow in the press screenings with six people at the table.” And I walked by and I made eye contact with him. He said, “Join us.” I shit you not, this a true story. And I sat down and we were waiting for the next movie and Roger Ebert with all the young reviewers and press people just talking movies. That guy was just passionate about. I was like, the only credit I ever met, what Mossberg would be the other one that would come to my mind, but generally they don't really support the industry.

[00:33:37] So as a founder, you got back to like, how do you pick. I like to look at the craftsmanship and the detail work. So when I talk to Travis about Uber and he was showing it to me, and he was like, “Hey, will you invest in my company?” I was like, “Sure.” And he's like, “Well, you want to know what it is?” I was like, “Nope, I want to invest in you.” And they said, “Well, let me show you.” And he shows it to me and he says it's Uber taxi and there were two taxis in San Francisco at the time, and the taxi was going down the road sideways. And I'm like, “What does that guy Tokyo drifting this shit?” Like why is it like that? He's like, “Oh, it's a really hard problem, Jason.” The iPhone 3G just got GPS and the cars coming down with this latency. And what we're going to do is we're going to make like seven or eight different versions of the car and then we're going to have it when we have certainty that it's going South, then we're going to flip it to show that view. But right now I don't have a designer. I'm trying to get some money raised so I can get a designer to make this two degree. And I was like, “Oh my God.” Like he's thinking about that shit, like maniacal focus on details. When I invested in Thumbtack, Marco's parents had invested and I was the second investor, which I'll always never forgive myself for, because like I should have gotten there before his parents, but I'll put that aside right now.

Jordan Harbinger: [00:34:50] I feel like it's a forgivable second place.

Jason Calacanis: [00:34:52] Not for me, not for me. I’m going to push this up.

Jordan Harbinger: [00:34:54] Oh, keep beating yourself up.

Jason Calacanis: [00:34:55] Yeah, but I was looking at it, Thumbtack now has a very slick way to match you up with a carpenter or a nanny or a piano teacher, whatever. But at the time, the first idea was a completely different idea, and that idea I invested in was, it was like a Yahoo directory of service providers.

Jordan Harbinger: [00:35:13] Like an Angie's list or something.

Jason Calacanis: [00:35:14] Sort of like Angie's list but better because what he did in it was you didn't have to pay. And when I was looking at the profile of this like painter, it had like four icons and I was like, “What are those icons?” He's like, “Well, hoover over them.” And it said like address confirmed, insured, driver's license. I was like, “How do you get their address confirmed?” He's like, “Oh, that's great. We send them a postcard with a code on it. They type the code in and we know that they got the postcard.” I was like, “Oh fuck, that's genius.” We just went next door stole from them. There's a really clever idea. I was like, “Why is it important that you know their address?” He's like, “Well, back to serial killers, I have a whole thesis on investing in companies around serial killers to put that aside. That's the next book.

Jordan Harbinger: [00:35:54] If you have a serial killer startup?

Jason Calacanis: [00:35:56] Exactly.

Jordan Harbinger: [00:35:56] Will you stay after the show?

Jason Calacanis: [00:35:58] So anyway, he’s like “You ever like get somebody off Craigslist and you wonder, is this person going to rob or kill me?” I'm like, “Every time.” And that's just in casual encounters. “Hey, joking, joking.

Jordan Harbinger: [00:36:10] Laying to that one.

Jason Calacanis: [00:36:10] Doesn't exist anymore.

Jordan Harbinger: [00:36:11] Does it?

Jason Calacanis: [0:36:12] No.

Jordan Harbinger: [00:36:13] Doesn’t exist anymore?

Jason Calacanis: [00:36:14] Just casual encounters exist? See it?

Jordan Harbinger: [00:36:18] I mean, maybe it does. I think so, maybe not.

Jason Calacanis: [00:36:22] Maybe, let me check my phone.

Jordan Harbinger: [00:36:23] Yeah, hang on.

Jason Calacanis: [00:36:24]  Yep, still exist. So anyway, I was like, “Wow, that's like an a level of craftsmanship that is laudable.” And so I look for those things and I'm talking a bunch now because I'm the subject of the interviews, but my team is always joking like it's really weird to be in a meeting with you, with the founder. And I'm like “Why is that?” It's like “Because you don't talk.” Like “Oh, okay.” Because I asked very short questions. “What's that? Or why are you doing this? Or what are you working on?” And I let them talk and talk and talk. And then eventually you can see that craftsmanship come out in that detail work out. And if you see that detailed work, you just think this person's paying attention to what matters, which is delighting customers.

[00:37:04] At the end of the day, startups have to delight some group of people, and they have to be scalable and they have to have a great margin. It's unbelievable to me how many people don't realize that that's at the core of what we do. Is it delighting somebody? Does it make a profit each time? People use it in some way, and can you scale it? A lot of people are just fucking around building features in like some vacuum and they're afraid to charge for their product and they're afraid to scale it and they don't talk to their customers and that's the kiss of death. Like you really need to talk to your customers and study how they use the product. The other example is calm.com, and I'm particularly proud of that investment that we made because at that time nobody would invest in Alex or very few people would, there were some. But people were writing like 25K checks and when I met Alex, I had them on the podcast, you can look it up.

Jordan Harbinger: [00:37:57] We’ll put it in the show notes [indiscernible] [00:37:59]

Jason Calacanis: [00:37:59] Make it in the show notes, and there was a moment where I was just like, “How did you get the domain name calm.com?” That's a four letter domain. It's $1 million domain name at least. He said, “I pay much less.” I'm like “Half a million?” “Much less.” I was like “Under a hundred?” He’s like “Yes, something like that.” Later told me, I think he paid 40,000 for it. I'm like a four letter domain name in 2014, how the fuck does, can you get me a four letter, can I get blue.com for 40 grand? Like I'll take every four letter word in the dictionary for $40,000.

Jordan Harbinger: [00:38:26] You can if you invest in my company calm.com.

Jason Calacanis: [00:38:29] Exactly. It was kind of his response. And he had been written off a little bit as, and this is tremendously cynical, but he had done The Million Dollar Homepage. Anybody remember a Million Dollar Homepage? Raise your hand.

Jordan Harbinger: [00:38:40] Pixels on it?

Jason Calacanis: [00:38:40] Yeah. So these are the old people. So gen X-ers, everybody else millennial. So what The Million Dollar Homepage was Alex wanted to make $1 million while he was in college. So he said, “I'm going to make a webpage and I'm going to sell each pixel on the webpage for a $1, and there'll be a million pixels.” And so he announces this and somebody buys their name Jason in like eight bit and it cost him 400 bucks. And people like that guy's an idiot for buying Jason in the center of The Million Dollar Homepage and then seven other online companies, because this thing's in the press, put their names on it. And then all the other eCommerce companies are like, “Well I need to be on that.”

Jordan Harbinger: [00:39:17] We got to be on this.

Jason Calacanis: [00:39:18] Right. And then since everybody's going there to see who's putting the bigger things in there, it becomes a competition. So now people are putting $10,000 items or $50,000 and it's like, “That guy's an idiot.” And then all of a sudden the page is sold out and he makes $1 million and he sweeps it, woop, zip, zip, zip. And I'm like, a cynic would look at that and go, “Oh that guy's a charlatan hustler, one trick pony.” And I looked at it and said, “That person is a brilliant marketer.” It’s the most efficient way to make $1 million.

[00:39:42] What else can you do? And it was calm.com was meditation. And I thought to myself, “Okay, I've been talking to him for months. He can't raise money, but he's special, clearly.” And so signals are going off. Look with Janell earlier where I said winner, winner, winner, like that was going off like even brighter like err, err, and invest, invest. And so I see that and I'm like, “Okay, I'm going to do that. Fuck it. Fuck it. You've got to make a bet once in a while. Sometimes you got to play seven, eight suited. Let's see what happens.” It's worked for me in the past.

Jordan Harbinger: [00:40:16] If you don't know what that means, don't gamble.

Jason Calacanis: [00:40:18] Don’t gamble. I'll tell a good story about that later. When I was a bad poker player and I realized this lesson. Anyway, putting it aside. I said, “Okay, I'm going to run it through this new thing because my friend Naval told me about syndicates and I started one and there's like a bunch of people who want to invest alongside me. So 60 of us put $378,000 into the company was worth 5 million at the time. And somebody posted on Cora, will Jason lose $400,000 investing in a meditation app? And I wrote a long defense of my investment and I said, “Listen, Phil Jackson is doing meditation with Kobe and Shaq, my friend Sam Harris is studying meditation and CAT scans at UCLA, and they've started this mindfulness center. That's UCLA, that's Phil Jackson, like this can't be not real. And if you think about it, yoga became this huge tradition in America where like if you go to Boise, Idaho, the motel aid has the yoga class. But like in the 70s, there were like four yoga classes a week in America, all in Santa Monica on donation base. So again, suspending disbelief and saying, “What's the one in a thousand chances it does work, what would it look like?”

[00:41:37] And then I had this crazy realization. Yoga, you need to go to a studio to do, but meditation, you close your eyes and you listen and concentrate and you could deliver it on this phone. And I said, “How much is the meditation class?” He said, “Yeah, most people donate.” They do a donation. I'm like, “Where can you do it?” He's like, “I can tell you some people who do it, but there's not really many meditation places four years ago.” And I said, “How much does it cost?” He says, “Well, it's usually donation based and most people would suggested donation will be 20 dollars.” I'm like, “How much are we charging?” Like “10 a year.” I'm like, “Huh.”

Jordan Harbinger: [00:42:12] 10 dollars a year.

Jason Calacanis: [00:42:13] A year. I said, “Why don't we make a 10 dollars a month?” He was like, “Do you think we should do that? We've been thinking about that,” and I was like, “Yeah, I think so.” So they make a 10 dollars a month and the sales go like this. And I was like, “Wait a second, you charge 10 times more, and it grew faster.” “Oh, perceived value.” And then subscriptions came out and they just closed around at 200--

Jordan Harbinger: [00:42:30] Subscriptions on the phone reoccurring, billing?

Jason Calacanis: [00:42:31] On the phone, and other places, reoccurring. So now he's getting, the last round was 250 million. Somebody offered us $16 million for our 400K position. I sold 10 percent of it. Took a quick little tasty poo, idiot insurance, gave all our investors a 3.5X return or so. And then we have 90 percent riding and the root--

Jordan Harbinger: [00:42:51] what does that mean?

Jason Calacanis: [00:42:53] Okay, so there's something called secondary shares. Sometimes somebody like Masayoshi son wants to buy some of Uber, so they give people who are early investors in Uber, the ability to sell some shares at a $50 billion valuation. So the new investors said, “We'll buy some of these shares at 250 million, which if you bought in at five, that's 50X 30, 40, 50X, you might want to sell some and then let the rest ride.

[00:43:15] The company's probably worth 500 now. And the rumor is they're doing 70, 80 million a year,  which we'll probably make it our seventh unicorn hopefully. But what I'm proud of is it was a very non-obvious investment until it wasn't, but my entire thesis was Alex, a person who the rest of the world didn't appreciate for greatness. And I think he's one of the 10 best product people in our industry ever. I'm like, “I'll put him up there with Steve Jobs and Elon and other really, Evan Williams from Twitter--

Jordan Harbinger: [00:43:53] Twitter.

Jason Calacanis: [00:43:53] Medium, and then Evan Spiegel from Snapchat. These were like really great product minds. I put Alex right up there and maybe in front of some of those names actually. I think he's going to build a $10 billion business. And that's when you're sitting there and you reflect on your life, which now I'm 47, which I do think about sometimes, like how many years I left. I go, “You know what?” That makes me feel pretty fucking goo, that this business might not exist if I didn't write that check. It makes me feel really fucking good that I'm going to make $50 million off of it too.

Jordan Harbinger: [00:44:24] Hmm, yeah, I can imagine how that would feel, and I will only ever imagine how that can feel.

Jason Calacanis: [00:44:29] No! You could feel it, you could feel it. You could go to jasonsyndicate.com and draw some syndicate and invest alongside me and you might feel it. And it's funny because that was the first syndicate investment. It's the most successful of all time. And this guy emailed me and he's like, “I'm in your syndicate and I've done six investments and I want to know, I have a very simple question for you, Jason Calacanis, are you a one trick pony the only thing you ever hit is Uber?” And I was like, “Well, have you been reading the updates? Which six deals did you go? And he list of deals, and like two or three of them are dead and one of them was Calm and one of them was another one. I was like, “Well, with calm.com, did you read last month's update? He's like, “No, I don't read the updates.” Like it's up 50x.” He's like, “Well, I put 6,000 in. Does that mean I have like 30,000 now?” “No, I say 50 not five.” He's like, “Well, I have 300,000 dollars now.” I was like, “Yeah, you have 300,000 dollars now. He's like, “You're awesome dude.”

Jordan Harbinger: [00:45:24] And that's when you stopped answering your email.

Jason Calacanis: [00:45:25] Exactly. It's pretty funny. But yeah, of course. I mean, I had the opportunity to raise bigger funds or join bigger funds and I kind of like being outside of the kind of venture capital complex because they make decisions with group think, and I think that's fine for what they do growth stage. But if you want to really make decisions with very small amounts of information in your gut, it's very easy to talk yourself out of an investment, and I did that with Twitter. I talked myself out of investing in Twitter and it was very painful for me, because I was right about my thesis and I was wrong about the investment.

Jason DeFillippo: [00:46:16] You're listening to the Jordan Harbinger Show with our guest Jason Calacanis. We'll be right back after this.

Jordan Harbinger: [00:46:21] This episode is also sponsored by Varidesk. Look, I love this Varidesk, I use this thing every day. This thing is a beast and I mean that, I mean that in a beautiful way. This ProDesk 60 Electric, it's a standing desk. It's a sitting desk when I'm lazy. It's an active workspace kind of thing. It sat in my garage for a minute because I was like, “This is going to take forever.” I don't want to put this thing together. It didn't even take more than five minutes to put together, but the thing is so nice. It's commercial grade materials. It's durable, it's stable, it doesn't wobble when I put stuff on it. I love that. That already beats every standing desk I've ever had. All the products are made to last. You can move them around. This thing is highly recommended. The ProDesk 60 Electric, and you can try Varidesk products risk-free for 30 days with free shipping and free returns if you're not satisfied. You can go to varidesk.com/jordan to learn more and check it out. V-A-R-I-D-E-S-K.com/jordan. I'm telling you this thing is, Jason, I use this thing every day. I didn't even know I needed this. That's how good it is. Now I'm like, where's my desk? I can't use other desks. It has ruined other desks for me.

Jason DeFillippo: [00:47:31] This episode is sponsored in part by Fin. I used to look at my calendar first thing in the morning and think there's no way I'm getting all this done and I knew I needed help. That's why I started using Fin is my personal assistant. You don't need to spend your time recruiting, training and managing an assistant. Fin can do it all. Scheduled meetings with coworkers or clients, answer calls, handled travel plans for your business trips, find and book service providers to fix things around the office and prospect new business opportunities. Fin does everything a great assistant can without the cost and commitment of a full time hire. And if you're someone who doesn't have 40 hours of work every week, you only pay for what you use. Fin is available 24/7, 365 days a year. Never calling in sick or taking time off.

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[00:48:45] Thanks for listening and supporting the show. Your support of our advertisers is what keeps us on the air and to learn more and get links to all the great discounts you just heard. Visit jordanharbinger.com/advertisers, and we also have an Alexa Skill so you can get inspirational and educational clips from the show in your daily briefing. Go to jordanharbinger.com/alexa, or searching for Jordan Harbinger in the Alexa App, and now for the conclusion of our show with Jason Calacanis.

Jordan Harbinger: [00:49:12] I have so many questions from an investor perspective, but I think from a founder perspective, a lot of these guys and gals want to know how do I take them? How do I know whether to take a meeting in the first place? Because there's a lot of angel investors now, especially with the popularity of books like this, where these guys are going to waste a lot of their time and what they're thinking is, “Oh, it's an investor, I've got to run to this meeting. I had to be there on time. I've got to impress these people.” You actually have, and correct me if I'm wrong, you are the bell of the ball here, not the investor. There's a lot of checks. They're all for the same amount. You're the ones that have the ideas that are going to be all stars.

Jason Calacanis: [00:49:46] I think that's important to realize because especially in the venture capitalists later on when they start investing, if you can get venture capital from one of the firms, you're probably going to be able to get it from all of the firms or the majority of the firms in that sector. So it becomes kind of like this weird dance where like you have three or four term sheets and you're picking one based on some track record or terms on the edges. I said earlier during the pitch panel, like listen, just do your backdoor references. Like talk to other founders and they'll tell you the truth. If you talked to anybody I've invested in except for one company it's going to be a stellar.

Jordan Harbinger: [00:50:20] Can you go over that again, that was on a panel that's not going to be spliced into the audio file of the show.

Jason Calacanis: [00:50:24] So somebody was asking earlier like how do know if this is a good VC for me? It's very simple. You look at their profile page on their website of their portfolio companies, and then you find 50 companies, then you look at Crunchbase or another database and you see they have 65 investments. Okay, who are the 15 companies they took off of their portfolio page and why? Slightly that they had some conflict with the founders, and the conflict could be the fault of the founders. It could be nobody's fault, it could be circumstance, whatever. So I would call those founders and I can tell you the reverse works as well. Founders will, you can call and interview people who know the founder of work with them previously and they're like, “Oh, that person's amazing and everybody loves them, and that's probably going to be a failed investment.” And then you need another, I was like, “Oh, that guy's an asshole.” And it's like, “ Unicorn. Here we go.” Big [indiscernible][00:51:19] facetious. But  sometimes founders are not very, they're cantankerous or they're hard to get along with. But for VCs, you'll find out very quickly if they're good at it. In terms of taking a meeting, you want to know what your goal is.

[00:51:34] So if you're raising an angel round, you should pick a time when you're going to meet with investors. You should make a list of the ones you want to target. You should reach out to them. You should be running a process, and after you raise money, then you should stop raising money and say, “We're not raising money. We expect to be raising money in Q1 of 2019. We'd love to meet with to then,” and then the power move I would do, and I was an entrepreneur is I’d say, “I really don't have time for a meeting. We're executing against a pretty aggressive plan. If you want to come by for a quick coffee one morning and you happen to be in Santa Monica, which was where I was located at the time. We'd love to have a quick cup of coffee with you, but I've got to hit these numbers.” And they're like, “Yeah, we'll be there. Can we come tomorrow?” It's like a real power move.

Jordan Harbinger: [00:52:19] Is it just me or does that sound like dating? Like, “Oh, I'm so sorry. I'm really busy crushing it. So if you want to stop by for breakfast or before breakfast when I'm usually in the office, like 4:30 a.m or so. I should be there.

Jason Calacanis: [00:52:31] Yeah, you can. I mean, yeah, I guess there's like the nagging kind of thing. Like I don't need money, but I was talking to a founder on the way up here. We were driving up last night. We stopped by a very charming little Artesia little donut shop, Tim Horton's. If you go South of here and you make a right on a Shell.

Jordan Harbinger: [00:52:49]That’s a unicorn, if I've never seen one.

Jason Calacanis: [00:52:51]  This is, I think we met the guy Tim create donuts. It's hard to, I'll give you the instructions later, but good coffee too. So I was talking to the founder and when I met him, he had 5,000 revenue a month, came to our incubator and now he has, he got a term sheet from a notable firm and he was in the process of meeting with maybe 10 folks and then he went to three more meetings and all three said yes. And I said, well now you've learned that the rule of raising money. When you're oversubscribed, everybody wants to invest. And when you don't have a lead, nobody wants to invest. These are all lemmings. Like once they see one firm come and they all feel like it's validated, they want to compete for it. So here's the tip or the technique. If you want to raise a million and a half, you go out to market and say “We're going to raise 750,” and then in your documents you say the minimum is 500 the maxims, 1.5 in your of, the deal will close if we raise as little as 500 and we can go up to as much as 1.5, and you want to go to out and say we have a 250K anchor investor, this person, Jason, whoever, and we have 500 open, we're looking for somebody else, and then things go very quickly.

[00:54:05] So I always advise people either you're raising money or you're building your business, but you don't want to be doing those two things simultaneously because they really are both full time jobs and that's why having a cofounder is so powerful because you can say, “Hey, you're going to run the business and I am going to 60 hours a week communicate and prepare for this fundraising over six to eight weeks.”

Jordan Harbinger: [00:54:25] This is like campaigning for office versus actually doing the job for which you were elected?

Jason Calacanis: [00:54:30] Correct.

Jordan Harbinger: [00:54:30] Gotcha, okay.

Jason Calacanis: [00:54:32] Four questions that you ask founders invest. These are must ask questions from investors to founders. I would love to wrap with these because these can be reverse engineered by smart people. Like everybody who's out here right now, what are these questions? Why do we ask them?

Jason Calacanis: [00:54:48] The question zero is if somebody referred, I say, “Hey, how do you know Jane? If like let's say Jane introduced us, and then it's a very short question, but I like to understand how the person was able to get the meeting. It's kind of an interesting question. What are you working on? Is my classic go-to because it does two things for me. One, it shows that I'm very interested in it, but it also uses the word work, which is my subtle way of conveying like this is going to be work.

Jordan Harbinger: [00:55:17] You watch and see if they just recoil when you say that word?

Jason Calacanis: [00:55:20] What are you working on? And then some of them are like, what do you mean by that question? And then other ones are like, “Okay, well we're built an application that is going to solve this problem and it's going to help you get a taxi and you're not going to have to wait.” And they just boom, they fucking run like a Mustang. Boom. Right up the hill. That's what I'm looking for. I'm looking for somebody when I just say, I fired the pistol. They can't shut up. And I'll ask that question, what are you working on? And literally 20 minutes later they'll be like, “That's what I'm working on.” I’m like “Wow, that's interesting.” And I'm taking notes the whole time. Why are you doing this or why this is a really good question to ask because maybe one out of four times I asked that question, the partner says, “Because I want to make a lot of money.” And I just think, “Oh, that just disqualified yourself.”

Jordan Harbinger: [00:56:05] Why?

Jason Calacanis: [00:56:06] There are much easier ways to make money than starting a company. 70, 80 percent chance of failure. If you really want to make money, figure out what the most in demand skill is, go acquire it, and then go work for Google for $1 million a year. Like, “Okay, you know how to do cryptocurrency. Great.” There is a million places for you to go get $1 million to work on cryptocurrency. “Oh, you know, augmented reality.” “Great.” Get the developer kit for Magic Leap. Now you can make a half a million dollars a year. That's a much easier path. Making $1 million a year or $500,000 a year for your skill for 10 years, guarantees you five to $10 million and you get to hang out on the roof of Hooli drinking margarita.

Jordan Harbinger: [00:56:43] Sweet! I want to sign.

Jason Calacanis: [00:56:44] Yeah. Why now is a question that I didn't come up with, but VCs are prone to ask the why now questions very simple. Why will this work now? And the reason why YouTube worked when it did was because previously when you posted a viral video online, you had to pay to put it online, and then they would, if a million people watched it, you're four million people watching it would be you get a $40,000 bill. So people, I don't know if remember this, like they put a video online, they'd share it and then you go to the website and would say, “This person's account has been suspended because they hit their bandwidth limit.”

[00:57:18] And what Chad Hurley realized was, “Wait a second bandwidth is that going down to zero and storage is going down to zero and so it's cloud computing was the reason. The other reason was syndication and blogs, which didn't get enough credit for YouTube success, which was nobody ever let alone giving away free video hosting and views. There was this other piece which was--

Jordan Harbinger: [00:57:37] Embed.

Jason Calacanis: [00:57:37] Embedded on your site. So I'm not getting the credit on my site. You're not going to real networks, you're not going to ESPN, and I'm putting ads around it. You're putting it on your site for free and you wrap it in ads. Holy fuck! Like that was crazy. And then Uber was obvious. It was like, “Well this doesn't work unless the iPhone supports GPS, because all the cool features of Uber are based on GPS in a phone, both for the driver and for Uber corporation to be able to bill based on that GPS data and match drivers and for you to see the driver coming. So no GPS, no Uber, no a cheap bandwidth and cheap storage and syndication of blogs, no YouTube. And you could ask this question about any business. Airbnb I think worked because of the reputation systems and social media.

[00:58:22] People got very used to reputation systems and trusting reviews on Amazon and on Facebook and so on. The social web kind of got released that answered that question. Is this person a serial killer or not? And so I think asking why now critically important a question and what's your unfair advantage? This is a really good one. I asked it today to one of the companies, which is, “Hey, if you're going to build this cloud kitchens competitor, what is your advantage?” If you're a building this super delicious Japanese style flash-chilled coffee café, flesh riff frothy, yeah, vanilla  caramel. It’s pretty delicious.

Jordan Harbinger: [00:59:05] We’ll link to that in the show notes don’t worry about it.

Jason Calacanis: [00:59:06] This Japanese style coffee, this a Miura, Miura, am I pronouncing correctly? I don't know.

Jordan Harbinger: [ 00:59:12] Oh he left such burner on promoting your business.

Jason Calacanis: [00:59:14] Anyway, what is his unfair advantage here? And I took him aside because he got no votes, and I gave a little pep talk. I was like, “Listen, you got no votes. You want to know why?” “Yeah.” I said, “Okay, number one, it's a consumer packaged goods and you're talking to venture investors. They don't invest in that category.” So it makes sense that you would get zero points.

Jordan Harbinger: [00:59:33] Why not? It’s too saturated or what?

Jason Calacanis: [00:59:34] Because it doesn't have venture economics typically.

Jordan Harbinger: [00:59:37] Because scale just can be exciting?

Jason Calacanis: [00:59:39] That’s your economics is in seven years can get you 100 million and have an 80 percent margin. It's very hard to have an 80 percent margin and things other than marketplaces and software because of the cost of the goods.

Jordan Harbinger: [00:59:49] You've got to move that coffee up away to rural Canada.

Jason Calacanis: [00:59:52] Exactly. But I had Dollar Shave Club.

Jordan Harbinger: [00:59:55] Where the real money is.

Jason Calacanis: [00:59:56] Like literally the founder of Dollar Shave Club chased me down the street in Santa Monica and was like, “You're Jason Calacanis.” “Yes.” And he said, “I have a company. Pitch me.” He said, “I'm going to get down, we're going to mail people razors.” And I said, “Listen to me, kid.” Razors, what's the new technologies like?” “Well, they're not under the triple blade like you used to let. That's not under patent anymore so I can make it and the next one is coming out of patent in two years and I'll be able to make that one, the quatro and the cinco.” And over there I was like, “Okay, good for you, kid.” Let me explain something to you kid, “That's not a venture scale of business.” And boy was I wrong, because he had figured out something very important, which was subscriptions to a consumer based good, acquire cheaply online with an incredibly high margin, with a very low mailing cost because they're not time sensitive. It doesn't have to be delivered in two days. You'd deliver five razors every month. It cost a dollar to send them. But I was too stupid and I was thinking about what I know, and this is when I switched from being a good angel investor to being the best ever in the history of the world.

Jordan Harbinger: [01:01:06] Debatable.

Jason Calacanis: [01:01:07] Was I stopped trying to understand, by who? Come on!

Jordan Harbinger: [01:01:12] Present company excluded.

Jason Calacanis: [01:01:12]  Exactly. No, the reason I can make that claim is because the four people were better than it all call enrich. Now they're all like Chris locker’s like “I'm rich. I'm not going back to work. Fucking meeting with founders all day.”

Jordan Harbinger: [01:01:23] It’s like hanging on cowboys shirts all day, I don't need [indiscernible] [01:01:25] office.

Jason Calacanis: [01:01:25] He says like “I’m done.” It's like anybody who does well, the reward for doing well in investing, it's like I don't want to do this. It's too hard to meet with founders constantly and deal with the struggles. I like it, but this is a $50 million mistake on my part and the reason I was able to fix a leak in my game. So when you play poker, if you have good friends who play poker with you, they'll say, they'll take you aside and say, “Listen, you have a leak in your game. Let me explain it to you.” A leaking your game is one that's a leak that is making them money flow off of your stack and to somebody else's. And the leak in my game was I used to think at two really bad leaks. I used to think I could make this business work. Therefore this founder's going to make it work. Well, I don't run the business. The founder does. So I invested in some kids and some folks who are dipshits and who didn't work hard and who weren't hustlers and who didn't want to make money. And I was like, “This is so easy.” Here's all you have to do to make this business when, just do it. And they're like, “Yeah, no, we're not going to do that. We're going to do this.” And I'm like, “But that's not going to work. You tried that for a year and it didn't work.” They're like, “Yeah, we're going to just do that because we think that's a better thing.” Just like, “Oh my God.” And the second leak was, I tried to figure out if the market would be there or not. And here's the thing, like I said earlier, the best founders create the market.

[01:02:43] I didn't think that founders could manifest a market that didn't exist before. And then I had to think, “Oh, wait a second. When blogs came out, people didn't stop reading the New York Times. They started doing that as well.” So sometimes the pie does get bigger, sometimes it's zero. Sometimes the pie doesn't get bigger, and sometimes it's just a whole new category that you can't define. And once I got out of that, then I could say, “Oh, dollar shave club. Yeah, maybe that will work.” And so now I don't even try to figure out if the business is going to work. I just figured out if the person's going to win at life. If I know they're going to win at life, I tried to get to know them. Make a small bet, watch for a year, six months, see if the metrics are going in the right way. See if the founder's a good leader or see if they--

Jordan Harbinger: [01:03:26] How can you tell if they're a good leader?

Jason Calacanis: [01:03:28] By the quality of the people they're able to recruit? I mean, is that simple? If you're a great leader, you will hire people better than you around you. And I see it all the time just I invest in somebody and like nobody will go work for them and they're just, you know, they're a high performer themselves but they can't get high performers around them. But if you can get these other high performers, so an investment we made is going to come to call density that founders fund, and Mark Schuster also invested in after we did. He's brought in like somebody from Apple and then another top sales executive and I'm like, “Wow! These people are got 20 years’ experience and they're much better than the CEO at their verticals. And you're like, “Oh, that's really how it works.”

[01:04:12] And if you look at Steve Jobs, he's the perfect analogy of this, which is what I call what got you here will not get you there. What got Steve Jobs where he is, is that he was an individual high performer, but he was an asshole to everybody apparently according to all accounts in his young years. Then he got fired for being a dick to his employees and everybody around him and being uncontrollable. And then when he came back, the second act of Steve Jobs was “Eddie Q, you're good at what you do.” “Tim Cook your extraordinary, whatever this is called, supply chain nonsense.” “Johnny I, you're a better designer than me.” And he just boom, boom, boom, boom, boom, lined up, all this extraordinary talent. And then he just came in and was like, “Good. Good. Okay, this is really good. Let's do this one and do this and then we'll do this one in two years and make that better. And he just was able to be a conductor, to be a coach.

[01:05:07] Those are the extraordinary performers, the ones who can put people around them and inspire them to change the world. Those are the people have the outlier success. Individual performance can get you to a unicorn status, but to be a legendary company that becomes worth hundreds of millions. Jeff Bezos just hires people who are maniacal and want to innovate and change the world. And then you see this New York Times story where people were like, “This is the worst, most horrible experience I ever had.” And then there are like another group of people were like, “I would never leave this company and work for any other person. I would rather die than not being working at Amazon,” and I call that the one five-star phenomenon. There are some places that are just polarizing. Like if you go on Glassdoor and you look at Amazon, it's like this is the greatest experience in my life. I owe everything in my life to Jeff Bezos and Amazon, and then there are people like “Run! Do not apply. Do not go there. They hate humans.” And Netflix was another one. At Netflix, they terrorize their employees. They're like every year we want you to reapply for your job. You’re like “What?”

Jordan Harbinger: [01:06:13] We're looking for someone who's 25 years old and has 20 years of experience. We want work life balance and you'll work 120 hours a week in a 40 hour time span. Leave us with some vinyl wisdom for founders like you see sitting before you right now with these guys and gals can do starting immediately.

Jason Calacanis: [01:06:34] Most important thing is to be relentlessly focused on what's working. And the biggest league for me as an entrepreneur was my probably undiagnosed ADHD. I don't know if I have it or not.

Jordan Harbinger: [01:06:49] Yeah, you do.

Jason Calacanis: [01:06:50] Okay.

Jordan Harbinger: [01:06:51] You're welcome.

Jason Calacanis: [01:06:52] All right. But it's a superpower, okay. It’s huge, okay. Which was, I would get some success in something and then I would build something else and then I would add it. And when I was at Mahalo, I kept adding things to the vision. And then there were like three things that worked really well. Our Q&A site, which eventually Cora became great at. We had a virtual currency, cryptocurrency that rewarded people for knowledge inside of Mahalo before cryptocurrency and Bitcoin existed. And then I did YouTube videos and we still make 15, 25,000 a month off the YouTube videos that we stopped creating six years ago. And we have a couple of channels with millions of subscribers, but I couldn't stay focused on any one of those things just because of my brain chemistry in my mind. And now with inside.com, I'm like, “We make newsletters.” The newsletters make money through advertising and subscriptions. We have 10 newsletters, now we have 30. Let's get to 100 newsletters and let's triple the number of sales people, and don't do anything else. And then people mentioned, we're like, “Well, we could do a podcast for inside and I'm like --

Jordan Harbinger: [01:07:55] Podcast not going anywhere. Everybody knows that.

Jason Calacanis: [01:07:57] We’re not a podcasting company, let's keep doing the newsletter thing, let's keep focused on that. And if you look at Airbnb, I think that's the most wonderful example. People kept telling them, do cars, do experiences, and they were like, “Until we get Airbnb everywhere, let's just get every Airbnb everywhere.” And Zuckerberg did the same thing. I remember talking to Chamath Palihapitiya about it. He was like, “Jason, the reason we're not doing photos or groups or all this other bullshit payments donations is because if we get Facebook localized in this region and we come up with Android support for these four phones, we add 50 million users. And if we do that, we make all users use the product 2 percent more. We should get the 50 million people on before there's a local competitor.  So what I implore you to do as founders is to not make the mistake I make and others made and focus on when you strike oil, keep drilling because founders are like, “Oh, shit oil.” And they're like, “Great.” Let's open an ice cream stand. I was like, “What?” Put another oil right here and see if we can pull some more oil out. And be relentless about that, see how much oil you can pull out of the ground. It's a bad analogy because it's bad for the environment, but if you look at what Elon’s done with Tesla, he just keeps trying to make a better car that goes longer and it's cheaper. That's it. First car went 150 miles and cost 150,000. They said it went 200, but if you're driving a Roadster the way it supposed to be driven, it's going to go 125.

Jordan Harbinger: [01:09:33] No one here has that problem. Then the model three just came out, it's 50 grand, and it goes 320 miles and when that 35,000 dollar comes out in two years, it's going to be a four or 500 mile one, and so don't take your eyes off the prize. Find something that works and just keep pulling that string, keep digging that hole and see how far it goes, and then there's always time for you to do other things but stay focused. Focus, don't get distracted.

Jordan Harbinger: [01:10:01] Jason Calacanis, thank you so much. Thank you so much for your time and thank you for coming out of the wilderness.

Jason Calacanis: [01:10:04] That was a great interview. Really, really good job.

Jordan Harbinger: [01:10:07] We have some books for you. But you got to bring your A game on the question. We're going to have--

Jason Calacanis: [01:10:11] Q&A tab.

Jordan Harbinger: [01:10:12] You come up here, and do a quick intro and tell people how this is going to work. If you want to tell them.

Jason Calacanis: [01:10:17] Hey, how are you doing?

Jonah: [01:10:19] Hi, I'm Jonah.

Jason Calacanis: [01:10:20] You are Jonah, correct?

Jonah: [01:10:21] Yeah.

Jason Calacanis: [01:10:21] Correct.

Jonah: [01:10:23] My question is as an 11 year old, what are your best like advice for an 11 year old to help you to make your journey easier.

Jason Calacanis: [01:10:36] Are your parents in the room?

Jonah: [01:10:37] My dad is.

Jason Calacanis: [01:10:38] Okay. Dad, cover your ears. Don't go to college. Number one, don't go in debt to go to college. No, skills are all that matter. You're going into an incredibly competitive world. You are up against people in other countries who will work twice as hard and for half as much. The only way for you differentiate yourself is to have the greatest skill of all. Do you know what the greatest skill of all is?

Jonah: [01:11:08] Business?

Jason Calacanis: [01:11:09] No, good try though. The greatest skill of all is the ability to acquire new skills. So what you need to do is be able to pick a skill that you don't have and figure out how fast you can get up to 80 or 90 percent proficiency in that skill. In other words, do you code?

Jonah: [01:11:30] No.

Jason Calacanis: [01:11:31] Are you a designer? You know graphic design?

Jonah: [01:11:33] No.

Jason Calacanis: [01:11:34] Are you a video editor? Can you edit video?

Jonah: [01:11:36] No.

Jason Calacanis : [01:11:37] Okay. Each of those things would take a couple of months of dedicated practice and research for you to become proficient at. Not the best in the world, but good, good at it. Most people in life would rather watch television and do anything but acquire new skills. You have to be fearless in life to be able to add those new skills quickly because whatever skills you learn this year, in 10 years, they may not be the important skills anymore. So for your generation, the ability to learn is most important and to learn quickly and to learn independently on your own. Not have a teacher, not have to go to college, but have the wherewithal inside of yourself to say, I'm going to sit down on a Saturday and teach myself how to video edit without anybody teaching me. I'm going to go on YouTube. I'm going to read a book, I'm going to get a podcast, whatever it is. I'm going to teach myself that skill, or else you will be toast. Because there are people in other countries who are willing to work for 1 dollar an hour for 70 or 80 hours a week and take all of the work from you and you'll have no job, no money, no home, and no future.

Jordan Harbinger: [01:12:49] These words of encouragement from Jason Calacanis.

Jason Calacanis: [01:12:54] Sorry dad.

Jordan Harbinger: [01:12:56] Take your gloc, man, you deserve it.

Male: [01:12:58] Aside from being an amazing angel, I think one thing that people should know is you're an amazing media empire. One of the things you do really well is you have 853 podcast episodes over the past eight years. What I want to hear from you is what has been the arc of podcasting for you and what are the top two or three direct impacts that podcasting has had on your business?

Jason Calacanis: [01:13:22] Yeah, great question. So I started podcasting because Adam Curry and Dave Weiner created it as a technical specification and then we did it at Autoblog and we got Volvo to sponsor. And I just thought this is an interesting concept for iPods literally at the time. It was called podcasting because Dave Wiener and Adam Curry, the godfathers of podcasting created software to download MP3s and put them on iPods. That's why it's called podcasting. What it's done for me is it gives me an excuse for twice a week for me to meet with important people and discuss important topics, which I would have been doing having lunch anyway. But by recording it and sharing it with the world and not compromising that conversation. In other words, I don't make the show that gets NPR. And on the next version where the cliffhanger of, you'll never believe what's going to happen on the next, what don't, you know?

[01:14:15] I just have a real conversation as candid as possible, that has built my brand as being candid, no bullshit and passionate about building companies. You know, what happens? People who are candid and no bullshit and who want to build companies say, “I'm in San Francisco, can I meet with you?” And I say, “What are you working on?” They tell me and then I say, “Great. Yeah, I'll talk to you.” And they say, “I have ideas.” I say, “Great, come back when you're working on something.” So for me, it's the top of the funnel. People watch that podcast and I have people I've invested in who are like, “I started watching your podcast when I was in high school,” and I'm like, “How old are you now?” And they’re like, “Well, I just graduated college.” I'm like, “Oh yeah, I've been doing the podcast for 10 years.” So it's everything, and it's a great joy for me to do it. I get as much as the audience does. So I think they're wonderful but get good microphones because sound quality really matters. Like invest in high quality microphones and get the best possible guests, and you’ll be fine.

Male: [01:15:08] Any recommendations?

Jason Calacanis: [01:15:10] I use a Neumann, which is a 4,000  dollar microphone that is probably indistinguishable from the shore microphone that most podcasters use. I think it's called the S5 and that is about 400. What's it called?

Jordan Harbinger: [01:15:24] I mean, you can get an SF duty. Honestly, you don't need an expensive one. You need to know how to use it and you need to make good acoustics in the room that you're recording in. And the rest of it is you need to not talk over the guests. No one to be quiet. No one will listen. It's really, there's nothing to it.

Jason Calacanis: [01:15:40] Good. Good question.

Male 2: [01:15:41] You had a strong belief in Alex. Oh it just, I had to because my name is Alex too.

Jason Calacanis: [01:15:45] Right, I love Alex.

Male 2: [01:15:46] You created a strategy off like making two lists. One way to fail, one way was to succeed. Do you apply the same strategy when you deal with multiple founders and what is your feeling or like go-to strategy if you have mixed feelings about one part of the founders and the other part of the founders?

Jason Calacanis: [01:16:02] Oh, good question. In a multiple founders scenario, like let's say three, I assume one will not be with the business for more than a year or two, and that the other two will keep going. And I'm looking for one of them or two of them to be great leaders and I try not to worry about that all that much. I don't think it matters. It does matter that on your legal documents, all three founders are vesting monthly for 48 months with a one year cliff or maybe even investing for five years, 60 months, so that if you leave, the other two founders are not screwed working every day to build up your chip stack. So that's why investing is so critically important. If you fully vested and you've been working on your company for four years and you try to raise venture capital, they will reset your vesting schedule or some portion of it and make you revest your shares for this key reason. That's the only thing that matters in these partnerships. And then being candid with each other, and the ability to tell each other when you're screwing up and the division of labor and being honest about that. And if it doesn't work out, I've had some times two founders break up and then I wind up investing in both eventually. So Kevin Durant played with James Harden and Russell Westbrook, and now they all are on three of the best five teams in the league. It’s okay if talent splits up.

Male 2: [01:17:20] Thank you ver much.

Jason Calacanis: [01:17:21] It’s a good question.

Female: [01:17:21] Whenever you're the one that is hyper-focused and being willing to go nonstop all the time, building a team around you that is willing to do the same. I keep running into problems of, I think they're hitting the mark and they seem like they want to run as fast as I do, but then they kind of burn out. Do you have a better way to filter through?

Jason Calacanis: [01:17:43] I had this issue in my youth. I expected everybody to be as Doggett and hardcore as I was. And understand that you as the founder and leader have much more at stake, and you probably be, since you created it to have much more passion and fortitude and as long as people are doing, 60, 70, 80, 90 percent of what you can do, they're probably going to be a decent enough contributor to keep around. And you can be candid with people and say when they come in, this is the expectation I have in terms of work effort, and I do it right now. I just stopped people, “Hey, can you come work for me?” I expect you to put in probably 45 to 50 hours a week. I want you to have a life. But if I email or text you, I expect that response in minutes, not hours or weeks. And I expect if I give you something to do, you write it down in a book and it gets done and if it doesn't get done, you tell me. And once I gave people that talk and I clearly defined the expectations, I had much less of a problem. In my youth, I thought it was my job to tell people when they were stupid or failures. And when I was in my 20s, I was an asshole.

Jordan Harbinger: [01:18:48] Hey, you must have a lot of friends.

Jason Calacanis: [01:18:50] I would literally this, I mean you want to talk about people who worked for me, that Silicon Alley Reporter would tell the stories, but I would have somebody come in and I'd be like, this is in front of 25 writers in the staff meeting. And I'm like, “Oh, welcome to the company. You have your piece that you wrote for the next issue. Great. Read it.” And they would start reading and there'd be a typo and they would correct the typo when they was set. And I said, “Oh, actually it says here theer, how do you pronounce T-H-E-E-R, theer? And they'd go, “Oh no, it's a typo.” I'd say “You brought a typo to the meeting? Are you going to put a typo on my fucking magazine that I put my entire life into? Get out.” I kick them out of the meeting to make an example of them. And I'd say, “Who's next?” And I ran the company through fear. And that strategy can increase performance until it doesn't and that everybody quits. So be careful taking the speed at which you run and demanding everybody else do it. Because they might collapse or just say, “I'm getting off this. This is too crazy of a train.” But it's something you learn over time and you can demand a lot of people, but maybe not as much as yourself as the founder.

Female: [01:20:02] Thank you.

Jason Calacanis: [01:20:02] Yeah. I wish somebody had told me that 20 years ago.

Jordan Harbinger: [01:20:05] Oh man, people probably did, you just didn't listen. Come on. Nobody told you?

Jason Calacanis: [01:20:09] That’s true. That’s true actually.

Jordan Harbinger: [01:20:10] Man, you're kind of being a dick and you weren't like “Fuck you! Get off my conference room.”

Jason Calacanis: [01:20:14 I think a lot of people did tell me to tone it down and I said, “You know what? You can tone it down.”

Jordan Harbinger: [01:20:19] Whatever, mom! I don't care what you know think!

Jason Calacanis: [01:20:20] No, what I would tell people, you know what? When your name's not at the top of the masthead, then you can take it easy. But if there's a spelling error or like an error in here and a factual error, it's on me. Go ahead.

Female 2: [01:20:30] Hey, I'm having an absolutely amazing time at this conference for the reason of, I have an idea that's not quite fully baked. It says it's much further than half-baked and I'm wanting to have all these one on one conversations where people are poking holes and really helping me think through what I'm wanting to do. I'm a very successful small business founder and I'm going to the next steps of opening multiple locations and potentially franchises. And one of the things that I have been questioned about a couple of times by different people over the course of this weekend, I don't have a good answer for is I have a business that I'm trying to decide, do I take it to be a huge market wide type of business like you would do with Uber or Airbnb? Or do I target specific niches and try to hit a certain smaller market place, but do it in a much more targeted intentional ways? As an angel investor, I imagine you have businesses come to you all the time that you don't see as a good investment because you don't see them being a company that's going to turn around and make you 10X, a 100X.

Jason Calacanis: [01:21:34] 10X. Oh, that's a disaster. 100X please. The next is death.

Female 2: [01:21:40] What do you look for in a company that you want to scale a 100X? That's kind of what I'm trying to decide is.

Jason Calacanis: [01:21:49] It's a great question. I got it. So it's very important to understand how investors make money and what motivates them. And I'll give you the short version, which is if you own 100 percent of the business and it throws off $1 million a year, in 10 years, you're going to make $10 million. And then if it's making, let's say $5 million a year with a million of profit, you could probably sell it for 10 times earnings for another 10 million. In other words, you will sweep $20 million off the table just by doing what you're doing and saying focus and taking no money. An investor, if they give you money, they're going to expect this to grow a 100X. And the reason is they want to make a 100 times their money because they're going to make a certain number of bets from their venture fund and they only make money after they return the $300 million fund size and then they make 20 percent of whatever comes after that. So they want you to swing for the fences and go big and do unnatural acts in order to make growth go supernova. So you just have to decide if you're going to get on the bullet train, if you want to go 200 miles an hour. But if you want to ride your bicycle. Both places can get you to a destination. The bicycle ride is super enjoyable and the bullet train is super and the Concorde is just super thrilling and it's just a personal. If you get good at running those small businesses and you love it, just keep running it and make it massively profitable. Sweep the money and you'll be super successful in life.

[01:23:16] If you want to swing for the fences and you want to see what it's like to build $1 billion company or get to 100 million in revenue or $50 million in revenue, then you would go to those investors and say, “I've built this really solid business. I want to build it to $1 billion.” You've done that before. How is that done? Will you mentor me and teach me how that's done and get other people on your board who will mentor you and teach you how to do it. And then understand that you're writing a rocket and some number of rockets don't make it to space and sometimes they explode, and sometimes everybody aboard them sadly dies. Except this analogy, nobody dies. The rocket blows up. Everybody magically gets put back on the bottom of Earth like a video game. You put another quarter in and you play asteroids again. It's a video game. If it blows up, who cares? You're a young person. You had one good idea that did well, you'll have more so don't sweat it. There is no success like failure.

Female 2: [01:24:15] All right, well thank you guys very much.

Jordan Harbinger: [01:24:16] Thank you.

Jason Calacanis: [01:24:22] We're done, okay.

Jordan Harbinger: [01:24:22] All right, great. Who need that book, by the way, that one and one, all you have to do is start a $100 million company and we will make sure that you get a book. You’re welcome.

Jason Calacanis: [01:24:30] Noted. Everybody can.

Male 3: [01:24:32] Well, thank you. Thank you so much Jason. Thank you so much to Jordan. Thank you so much. That was unbelievable.

Jordan Harbinger: [01:24:41] I got to tell you, man, doing things in front of an audience is kind of cool. I would love to do that every time if I could.

Jason DeFillippo: [01:24:48] It was so much fun and I did my show in front of an audience there too, which was actually quite enjoyable, but it was great seeing Jason again. I haven't seen him in so long. When I started my first blogging network, he offered to buy me out for $10,000, and it was the dumbest decision I ever made, not to take him up on that offer. I have to say.

Jordan Harbinger: [01:25:06] Oh man, you would have taken the 10K?

Jason DeFillippo: [01:25:09] He offered us $10,000 for 50 percent of our company and my business partner said, “No way, no way. That's never going to happen,” and we should have done it because we'd have been gazillionaires right now. Then again though, I never would have been doing this and met you. So you know win some lose some, and on the plus side, I still get to do this show every week, so I'm happy about that.

Jordan Harbinger: [01:25:30] That's right. That's right. You get to do this show every week and you never know. That could have been one of those things that stuck in your craw and didn't work out. You never really know.

Jason DeFillippo: [01:25:37] That's true. Startup investing and startups in general are just a roll of the dice.

Jordan Harbinger: [01:25:43] Yeah. Can kind of go horribly, tragically wrong a lot of the time as we learned here from Jason Calacanis and I think that it's really, if there's anything I've learned this year, it's 2020 hindsight. It has a lot of bias involved. It's just one of those things that you kind of can't get around. And if you can drive yourself crazy going back and forth it and it's really not worth it. Let me tell you.

[01:26:04] Big thank you to Jason Calacanis. The book title is Angel: How to Invest in Technology Startups - Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000. And like I said, he's way past that now. If you want to know how I managed to book all these great guests, manage these relationships, you know, when someone comes on the show, I don't just not talk to them at all. After that, I have them here for in my rotation, in my text messages, calls, catch-ups, visiting, whatever it is in person, whatever we can do, they're in my rotation forever. And I do that, I use systems, I use tiny habits, and I don't take hours every single day quote unquote networking. I want to teach you how to do this and I want to teach you how to do it for free because I think it's one of the highest leverage skills you can have as pretty much anyone in business or in the working world at all. In fact, opportunities in life generally come from this. So I don't care what you do or what you don't do. You need these, you need these skills. Check out our Six-Minute Networking course which is free over at

jordanharbinger.com/course, and I think a lot of people want to postpone this. They want to do something like, “Oh I'll do it later. I'll check it out.” You can't make up for lost time. When it comes to relationships, when it comes to networking, you have to dig the well before you're thirsty. Don't wait until you need a relationship or a connection. It is too late. This is the stuff I wish I knew a decade ago. You can find all of it at Advanced while almost all of it. There's LevelTwo of course, you can find all of that, all of Six-Minute Networking anyway at jordanharbinger.com/course. There's a dozen or so exercises there for you. I would love to hear what you think about them and tell me what shakes out.

[01:27:46] Speaking to building relationships. Tell me your number one takeaway here from Jason Calacanis. I'm at @jordanharbinger on both Instagram and Twitter. I do a lot on Instagram. I always answer my tweets just like answer my emails and don't forget. If you want to learn how to apply everything you heard from Jason Calacanis, make sure you go grab the worksheets also in the show notes at jordanharbinger.com/podcast. And this episode was produced and edited by Jason “I should've took the deal” DeFillippo. Show notes are by Robert Fogarty. Worksheets by Caleb Bacon. Booking back office and last minute miracles by Jen Harbinger. I'm your host, Jordan harbinger. The fee for this show is that you share it with friends when you find something useful. I hope that's in every episode. So please share the show with those you love, share the show with those you don't. I've got a lot more great stuff coming for you. Here's to another hundred episodes and change, and in the meantime, do your best to apply what you hear on the show so you can live what you listen, and we'll see you next time.

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The Ultimate Angel Investor with Jason Calacanis

In the past year, more people have abandoned traditional nine-to-five jobs for self-employment opportunities like investing and entrepreneurship. However, the industry is saturated with tech-inclined youngsters who are prone to taking uncalculated risks. In this Startup Edition of The Money Movement, we discuss startup investing culture and explore the shortcomings of the space.

Joining us this week to explore this topic is Jason Calacanis , Entrepreneur, Angel Investor & Author. After investing in one of Uber’s early rounds, Jason now has over 10 unicorns in his portfolio. Aside from being the Founder & CEO of LAUNCH, and the host of This Week in Startups and the All-In Podcast, Jason is also the author of the best selling book: ANGEL: How to Invest in Technology Startups.

All securities-related activity is conducted by SI Securities, LLC ("SI Securities"), an affiliate of SeedInvest , and a registered broker-dealer, and member FINRA/SIPC, located at 61 Broadway, Suite 1705, New York, NY 10006. SI Securities does not make investment recommendations and no communication should be construed as a recommendation for any security offered on or off the investment platform.

Listen to this special startup edition of the Money Movement with Jason Calcanis now!

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Angel: How to Invest in Technology Startups—Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000

By Jason Calacanis

( 21 ratings )

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About this ebook

One of Silicon Valley’s most successful angel investors shares his rules for investing in startups.

There are two ways to make money in startups: create something valuable—or invest in the people that are creating valuable things.

Over the past twenty-five years, Jason Calacanis has made a fortune investing in creators, spotting and helping build and fund a number of successful technology startups—investments that have earned him tens of millions of dollars. Now, in this enlightening guide that is sure to become the bible for twenty-first century investors, Calacanis takes potential angels step-by-step through his proven method of creating massive wealth: startups.

As Calacanis makes clear, you can get rich—even if you came from humble beginnings (his dad was a bartender, his mom a nurse), didn’t go to the right schools, and weren’t a top student. The trick is learning how angel investors think. Calacanis takes you inside the minds of these successful moneymen, helping you understand how they prioritize and make the decisions that have resulted in phenomenal profits. He guides you step by step through the process, revealing how leading investors evaluate new ventures, calculating the risks and rewards, and explains how the best startups leverage relationships with angel investors for the best results.

Whether you’re an aspiring investor or a budding entrepreneur, Angel will inspire and educate you on all the ins of outs. Buckle up for a wild ride into the world of angel investing!

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Angel - jason calacanis, chapter 1, someone else was supposed to write this book.

This book has a singular goal: to teach you how massive wealth is created in the twenty-first century.

It’s not a system or a secret, so I’m not going to build this up into something fancy like those bullshit self-help books you’ve already bought.

I’m just gonna tell you how a C-minus student from Brooklyn (before Brooklyn was cool) clawed his way into the tech industry, got lucky seven times (and counting), and made tens of millions of dollars.

Most folks think I’m lucky, some say I’m a complete fraud, and a handful think I’m a brilliant hype man, and I don’t agree with any of them—I agree with all of them.

That’s why this will be the greatest business book ever written. I shouldn’t be the one writing it, yet here we are. I’m the outsider who made it in, letting you know how he pulled it off.

I am as shocked as anyone I made it here, and it’s a hell of a story: the son of a nurse and bartender watches his family lose everything when the feds—wearing raid jackets just like in the movies—burst in with shotguns to take back his dad’s bar. He crosses the bridge to Manhattan with something to prove and, ultimately, he heads to the West Coast to make his fortune.

The American Dream

The American Dream still exists, it’s just not as widely distributed.

Our parents and grandparents took factory and white-collar jobs and rode them for all they were worth in the last century. Now the robots—who never sleep and self-improve on an exponential curve—are taking these jobs. Meanwhile, we humans, with our nagging physiological and emotional needs, struggle to keep up.

Most of you are screwed.

But you’re here, so you’re clearly willing to learn and I can radically improve your odds if you do the work.

The world is becoming controlled by the few, powerful, and clever people who know how to create those robots, or how to design the software and the tablet on which you’re reading this. But please don’t stop reading, because I’m going to show you how anyone can get a seat at the table with the digerati, illuminati, and moneyrati and, perhaps, tap into this hundred-year boom.

Yeah, I’ve got my own formula like those other business books you’ve bought, but there is a major difference between my formula and theirs—mine is forward-looking.

All of the other books out there, and some are great, try to explain to you how people made money in real estate, by mastering the art of the deal or by getting the right people on the bus (and the wrong ones off), but they are largely historical documents now.

The world has changed more in the last ten years than it did in the last ten decades.

That’s not just some clever one-liner to say in a conference keynote or at a dinner party. It’s an undebatable fact.

The changes we’ve seen with the internet, with mobile phones, with robotics, with sensors, and in biology are mind-blowing not just to civilians, but also to the people working in these fields—and the pace is increasing.

I could give you a list of mind-blowing breakthroughs to prove my point about how fast things are moving, but I’d like this book to stand the test of time, and the truth is that giving you examples like a computer beating a human at chess, or an encyclopedia made with no paid writers, or computers flying airplanes and cars without steering wheels, or wars being won with robots, are so commonplace that science fiction is having a hard time remaining, well, fiction.

I know because the top-tier investors who invested in the last fifty big things call me to find the next big thing. I live on the edge of the future of business and technology.

As an angel investor, it’s my job to write the check when no one else believes in you—and that’s the most thrilling bet in the world.

Every week I meet a dozen dreamers with insane ideas who want me to give them my money, advice, and access to my Rolodex—but mostly the money.

Oftentimes I’m the first money in, the first investor willing to take a chance with a company like Uber or Thumbtack when they are only worth four or five million bucks and almost everyone else has said no.

This year I invested $750,000 in a company that makes a robotic cafe called Cafe X. It eliminates the two most expensive aspects of Starbucks’s business: real estate and humans.

When the founders emailed me a video of the prototype in action at a college in Hong Kong, I wrote back to them, Is this a joke?

They said, No, it is not a joke, so I invited them to come to my incubator where we spent three months refining the product and helping them craft their pitch. Then I introduced them to my rich, powerful, and, in many cases, compulsive-gambling, narcissistic friends—who funded the company for millions of dollars.

If we succeed with Cafe X, we will reduce the price of a latte to $2 (again), make it perfectly every time (a computer never forgets how much foam you asked for), and reduce your wait from more than five minutes to under thirty seconds (the machines know where your smartphone is and they make your coffee when you’re ninety seconds away).

Instead of a Starbucks on every other corner in a city, there will be a Cafe X machine in the lobby of every building on the block.

Instead of being open fourteen hours a day, these robots will serve us twenty-four hours a day.

Cafe X and other startups will also eliminate millions of jobs in which humans get paid to stand behind a counter and repeat back your seven precious little instructions on how to prepare your morning libation, before pressing one button and masturbating a milk-frothing pitcher for two minutes.

The Future of Jobs—and Making Money

If right now you think I’m a horrible, marauding, free-market monster, you’re only half-right—I’m also a humanist who thinks there are better things for our children to do with their time.

The quicker we eliminate the low-paying, repetitive, and menial jobs, the quicker our species can get to work on bigger issues like sustainability, being multiplanetary, and perhaps retiring the last couple dozen dictators and despots who are murdering, raping, and otherwise oppressing the weakest among us.

Of course, I could be wrong.

When we eliminate all these jobs, the world might spin into a global version of the long-forgotten dry run Occupy Wall Street where a group of savvy but poorly organized hippies and millennials slammed their feet down and said, No more! We’re not leaving until things change!

Until, of course, the economy rebounded and they got cool jobs with free food and their own private drivers from uberPOOL, then realized that, net-net, things are actually pretty fucking awesome and they don’t need to storm Michael Bloomberg’s town house or stink up the Goldman Sachs lobby anymore.

In my mind, candidly, we’ve got a 70 percent chance of figuring out this massive sea change without starting a full-on revolution in the streets, like we saw in Greece or Egypt, or any other place where unemployment among young adults breaks 20 percent.

But I don’t invest in this future because I want to sit in an ivory tower laughing at people whose jobs are replaced. I invest in this future because it’s inevitable and I think I can help accelerate the efforts of the founders and innovators who are missionaries, not mercenaries. Of course, I plan to make a great deal of money in these revolutions, but I also plan to look back proudly and know that I helped propel changes that made our planet better.

Escaping the Matrix

If you’re reading this, congratulations! You chose the red pill and you’ve taken your first step to understanding the bitter truth: the world is going to get flipped on its head two or three more times in your lifetime.

The jobpocalypse is coming, which is not just based on my coffee-making robots. It also includes the elimination of most white-collar jobs we were told were careers, like being a lawyer, doctor, teacher, accountant, pilot, journalist, or—wait for it—a software engineer.

Yes, while the greatest opportunity on the planet today is probably being a software engineer, I just invested in a company that hopes to eliminate software engineers by letting you type into a box make me an app that does X, Y, and Z, before spitting out your own version of Uber for . . . [insert service that sucks right now].

If you haven’t had a panic attack reading this introduction yet, let me tell you the next product I’m looking to back: an artificially intelligent robot that studies humans and builds other robots.

I haven’t found it yet, but I probably will by the time you reach the end of this book. The snake is going to eat its tail.

When that happens, there is a good chance that it will be every human for themselves.

By the way, a lot of rich folks have already planned for this outcome by buying islands or huge ranches in remote places like Wyoming or New Zealand (I’m not kidding) that are fully off the grid—complete with solar, water desalination, fortifications, and weapons.

Yeah, there are billionaire preppers, not just hillbilly ones.

A perfect storm of black swans is coming and this book is going to prepare you not only to survive it—but to ride it out on top.

Chapter 2

The brooklyn grinder, is angel investing gambling.

Folks in the technology industry debate if angel investing is gambling or actual investing, and it depends largely on how you approach it. Every year I place forty bets hoping to win back more in aggregate than I’ve put down.

I’ve invested just under $10 million in the six years I’ve been angel investing, and the portfolio I’ve built is worth over $150 million—that’s a return of fifteen times my investment.

That’s mind-blowing for a kid from Brooklyn who watched his parents fight, at least 90 percent of the time, over money.

More mind-blowing, however, is that the majority of my investment dollars were invested in the past three years ($9 million of the $10 million, in fact).

If you drill down, I invested under $100,000 in the first year as an angel and hit my two big winners to date, Uber and Thumbtack, in my first five investments.

The return multiple from the first two years of my investing is actually fifteen hundred times.

These startups take ten years to play out, so no one knows exactly where I will sit in the hall of fame of angel investing—if one is ever built—but it is safe to say I’ll be in the top ten angel investors of all time.

I buy lottery tickets for a living, but unlike the normal schmucks on the street, I get to buy tickets that are in the top 1 percent of the winning pool.

If you have to match seven numbers to win with your lottery tickets, I have to match just two.

I’ve figured out, and will explain to you in detail, how I’ve gamed the system. I’ve rigged the roulette table so it falls on my number ten times more often than yours.

I’m starting every hand of poker with the ace of spades, so my chances of hitting pocket rockets are 1 in 17 while yours are 1 in 220.

If you can’t tell already, I’m really excited with where I am in life. Sorry if I sound like an obnoxious narcissist who thinks he’s figured it all out—but I actually have. For years people asked me to write books and I kept telling my agent one more win.

The Sequoia Scout Program’s Secret Origin

Investing in the cab company that changed the world was that one more win. When the Wall Street Journal did a front-page story on my role as the first Scout for Sequoia Capital, the most famous venture capital firm in the world, everything was revealed.

Yep, the brilliant venture capitalists (VCs) who backed Apple, Google, Cisco, Yahoo!, YouTube, Airbnb, WhatsApp, and countless others had started an angel investing program called Scouts, and I was the first one selected.

Scouts was a simple concept: Sequoia Capital would put up the money and twenty carefully selected founders of technology companies would pick founders they know to back.

The returns would be split: 45 percent to the Scout who made the investment, 50 percent to Sequoia, and 5 percent in a bonus pool to the other Scouts in the program.

This was the deal of the century for us Scouts, because venture capital firms like Sequoia actually only get 20 to 30 percent of the returns when they invest other people’s money.

My hunch is that they didn’t care what the split was because we were a bunch of nonprofessional investors and the chances of us hitting a home run—let alone a grand slam—were minute. For them, Scouts were a way to increase their visibility into the early-stage market.

The kid from Brooklyn was anointed by the smartest cats in the business. My job was to find the next big thing. It was like George Steinbrenner calling me and saying, How would you like to help the Yankees win another World Series?

Holy. Fucking. Shit. YES!

I Used to Dream About This Life

When I was a kid I always dreamed of having a dad who was a rich banker or billionaire, going to Harvard, and having a trust fund—as opposed to having a dad who almost went to jail.

I’d dream of what it was like to be on the inside and have your college tuition paid for, your apartment in Manhattan gifted to you, and getting $100,000 to invest in a business if you lobbied your parents for fifteen minutes over Thanksgiving—like many of my friends had.

I didn’t have that privilege and it put a fire in my belly.

I would sit there on the B train heading home from Fordham at Lincoln Center at ten p.m. on my way home to a three-hundred-dollar-a-month attic apartment on Tenth Avenue, where the only place you could stand upright was about 20 percent of the space in the dead center of the hallway, and think to myself, What would it be like to be rich?

What would it be like to have $100,000 on the ATM receipt instead of $100?

What would it be like not to have to worry about money every day of your life? I was so broke that when I was in college I would go to Manhattan at night with two tokens and $2 in my pocket, knowing how to spend it perfectly to get maximum calories from the hot dog vendor by Central Park who charged only $0.50 for a knish instead of $0.75 like everyone else.

I would buy a bagel for $0.50 on the way in, two knishes for lunch, and a third knish on the way home—unless I spent it on a Coca-Cola like an idiot so I could stay awake in class.

When you’re broke and see rich people in Manhattan all around you, it makes you curious: How did these people become rich?

Pass On What You Have Learned. —Yoda

So, I studied every system in order to find one that is the most efficient for capital creation, and I believe that it’s angel investing in technology. I’m going to tell you everything in the coming chapters because if just one or two hundred of you become angels, it will make an impact on society—plus we can invest together (more on this in chapter 11)!

Heck, if just one person uses this book to back the next great founder who has a world-changing idea, we’ll have made an impact together.

There’s an outside chance that twenty-five thousand of you might become angel investors, and if that happens, it would change everything.

The world has trillions of dollars sitting in bonds, cash, stocks, and real estate, which is all really dead money. It sits there and grows slowly and safely, taking no risk and not changing the world at all.

Wouldn’t it be more interesting if we put that money to work on crazy experiments like the next Tesla, Google, Uber, Cafe X, or SpaceX?

I’m forty-five years old at the time I’m writing this and I plan on doing five more years of angel investing—I’m on a ten-year plan.

Another two hundred bets and I’m done—then it’s your turn.

By the time I’m done with my ten-year plan, I will have invested in 350 startups and my goal is to return $250 million on $25 million deployed—I’m exactly halfway there.

No Gamble, No Future

Now, gambling has a very negative connotation here in the West, but when I would spend all night playing poker in Los Angeles, with mostly old Asian men, I would frequently hear them say No gamble, no future, before pushing their chips into the pot, standing up, and rubbing their necks and heads furiously (a tic I soon acquired unconsciously).

It took me a couple of times to understand what these old men were saying, but I quickly started saying it myself, whether I was at the tables or not.

No gamble, no future.

If you learn anything from this book, it’s that you must take risks as an angel investor and in life if you want at least the chance of an outsized outcome.

This does not mean you should be reckless; in fact, it means the opposite. I’ve studied and studied how people have built wealth as angel investors and I’ve focused on having an unfair advantage over them.

I’m going to reveal every unfair advantage I have developed in the coming chapters so that you can deploy your money intelligently, or perhaps just more intelligently than everyone else, which, if you’ve ever won at poker, you know is the key to success.

If you can’t tell who the sucker at the poker table is, it’s you, so find another table or figure out how to be better than each of the other players. This might take time, but everything worthwhile in this life takes time and effort.

For the Real Outsiders

As much as I feel like I’m an outsider—a kid from Brooklyn who didn’t go to Stanford and was born into the bottom of the middle class—the


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    One of Silicon Valley's most successful angel investors shares his rules for investing in startups. There are two ways to make money in startups: create

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