you are listening to absurd 41 off the 20 minute VC with your host Harry Stabbings. Now today is an incredibly special day at the 20 minute VC as we welcome the incredible, the legendary Jason Kala canIs Where do I start with an injury for Jason? He's one of the greatest angel investors in the world, with over 60 Angel investments, including the likes of uber on dhe thumbtack, just to name a few. He's also the host of the immense This week in start ups, he's the founder at Launch on Launch Festival. Andi. He sold his previous company, Web logs to a O. L for 30 million. Now, if you listen to this week in Startups, you'll know that Jason has the incredible Jackie to assist with the running of the show. Well,

with the growth of the 20 minute VC, thanks to the amazing folks at Product Hunt, amazing guests like Jason Theme Time has come for me to get my own. Jackie. A tough to ask, I must admit, but made incredibly easy with the help of hiring screen, the smartest and fastest way to identify the most relevant candidates for a job they help me sift through 184 CVS in just 15 minutes on. Now, I have found my very own Jackie whoring screen. I couldn't have done it without you, but without further ado, here is Jason Kala Kanis. You have now arrived at your destination. Jason. Welcome to the 20 minute VC is a huge honor to have you on the show on. I'd like to start by hearing what you think about the 20 minute VC as a

show, and it is a great ship. Okay, Would you just thought you should just do what we should do? A conversation about podcasting

That would be like, really, really interesting one. Where's the future of poor costing?

Well, here's the thing. You know, I started this podcasting company this weekend with my friend Kevin Pollack, like, six years ago. And then we gave up after about three or four years on trying to get other people to do it, because it seemed like only the only way it worked. It's of some crazy maniac with a really good reputation and network was willing to work for free for a couple of years, and then the podcast would naturally work in your 45 like Adam Corollas is or Kevin policies or Leo reports is remind us. So we may have given up too early, you know, this weekend on doing that network. But we just couldn't get people who were. You get people who were up and coming to do podcast. We couldn't get people who were arrived to do pockets up and comers. You know,

they got spent 45 years doing it to even get somebody to pay attention and maybe sponsor if you're somebody, it takes two or three years to get somebody to get people. You'll get people to pay attention in your one if you got a little bit of an audience, but I'll take two or three years to get revenue. So you know this week in startups is now. It's $5000 in advertisement. We do 104 episodes a year to add, so it's 208 adds a year. Some people get discounts. I mean, it's gonna hit a $1,000,000 in revenue on Day four or five full time people

on it is $5000 per sponsor

per sponsor

per week, and that's what you're viewing figures

$150,000 for episode.

Do you check them? Kind of wonder. Yeah. Hello? Yeah,

yeah, way. Super distribute. So you'll see on YouTube. Like, you know, maybe an episode gets 1000 there or might get 20,000. And then this archive powers is crazy. But most people are using podcasting, APS now, whether stitcher or tune in or overcast or swell, which was an investor. And we sold a well, this the apple iTunes podcasting app is amazing. So

really, if you had about rule all right. Yeah. Aw, ay, you all. Yeah, it was product hunted. Dave McClure is invested in the seed fund. Well, actually, the founder reached out to me, asking me Thio suggested to you just now. So I stopped by hearing about you. But, I mean, we obviously hear a lot about your investment enable Incredible. On DDE. How did that come about? And how excited are you for the future of either?

Well, I'm obviously delighted with you know how the company's turned out, but it's not unexpected that this would become an important company because the founder Travis, who have known for 15 years when I was a journalist. I interviewed him when he was doing Scour, which was a peer to peer company. Sort of like Napster. But it did every file type. And I remember when he was very young, maybe 23. 24. I was interviewing him, and I was a couple years older than him running a magazine. Destroy Coast reporter and silicon, our reporter. And we have 100 v i. P s in a room at Castle Del Mar in Santa Monica.

And he had just been sued for 1/4 of a trillion dollars by movie companies. Yeah, and he was visibly shaken from this, I'm sure because he was, you know, he was a kid, you know, when I was a kid and, you know, it was obvious. He was brilliant, obviously was hard working. Then he did a company called Red Sweetie. We were just always friends would like to talk and hang out.

And decent accident, wasn't it?

Yeah, I think they did. 25 million. 30 million. Mark Cuban was an investor in Mark Cuban's vested in my cos we're all kind of in the same. Came up in the same web one point. Oh, So I think you know, people on their 3rd 4th springing back can do really well. Whether it's Evan Williams with Twitter. He did Hey, did Odio and then blogger before that. Twitter, obviously. What's his third time up in that? So I love Founders were not the third time a baton when he showed it to me and asked if I could invest because I had passed on investing in Twitter and I passed on investing in Single, which are two of my very good friends.

Other start ups and I don't really consider myself an angel investor, But, you know, it turns out that angel investing, I think at its best is investing in people and investing in their passion and trusting them. And it turns out like I'm pretty good at reading people. That may not be the greatest entrepreneur. Certainly not. Um, I'm definitely not the smartest guy in the room. Typically not, but I'm pretty pretty darn clever when I need to Bay and I have a gift for reading people

and knowing what a good sport that eye of the tiger I'ma be set on You in the product on the podcast you called it the eye of the tiger and the entrepreneurs eyes. How do you spot that isn't their passion.

You know what it is very, very weird. I could try to explain it to you, but I would seem like really pretentious. But the truth is, you know, when I'm talking to somebody, I almost feel like I see past their eyeballs and I see into their brain and their soul. And I see if they actually give a shit and I can tell you, you know, seven of 10 times at me with a founder, I can tell they don't really give a shit about what they're doing. They're just like they're doing it because they want to be a founder. They're doing it for some reason. But this isn't their passion. This isn't the idea that's gonna do it for them. But sometimes,

you know, maybe 30% of the time when I'm talking to somebody I could see like, Holy cow, this person really cares about this. Okay? So now I can very easily knock out seven of 10 people, you know, when I'm meeting with them and I just in my mind, I say, Look, listen, this is not. This person might be successful, but generally speaking, people who are not passionate and really believe in their idea and really want to do it. Um,

look, it's not worth me investing in them because it's probably a one in a 500 chance that they're gonna be successful now that last 30%. It's probably, you know, it's still a 10 or 20% chance that they're going to get me a great return. But if I can get to a point where 10% of the people are investing, get me return or 5% or even 1% you know, I have a $10 million angel fund. Now, if I wind up investing in 100 companies on average, you know, probably half of them are 25 K investments, and then the other half are two or $300,000 investments because you double triple down on your winners. Wow, you know, I'm gonna be one of the greatest angel investors A little time,

which is really my goal. Right now. I want to be the best angel investor in the history of angel investing, and I think you know, if you asked any entrepreneur who which. Which angel investor, what they wanna have on their team. I think you know, I would most people under where you would put me, but in terms of desirability, I'm definitely

the top 10 time. You got to be top three. Jason. Let's put Chris Sock in. Tim Farris?

Yeah. I mean, I think if you ask people, I think that is very

reasonable. Would you agree with that?

I would absolutely agree with

credit deal. Pantene is going to be up. That too.

Yeah. I mean, definitely in the conversation for sure. You know what? I think it depends on what you're working on. So if you were doing sass, you know, I put Gil ahead of myself and Tim Farris and may be on par with soccer. I mean, stock is just a whole nother level, so I put Sakas number one hands down right now. What

would you call soccer and an angel there now? I mean, surely with, uh,

you know, Chris and I are very good friends, and, you know, I think he's very selective right now, and he's kind of like laying back a little bit, so I don't know exactly how to define Chris. Other than he's a mention, a legend. Just leave it at that. You know what he chooses to do going forward, you know, who knows? I mean, I think the guy has done so well. He's gotta, like,

step back a little bit and think about, you know, gosh, if you hit, you know, it's sort of like being like Michael Jordan or something like that. At a certain point, you're like, Well, I've got seven rings or six rings or whatever. Like, what am I playing for? Exactly? And I think he's probably in that mode of Like whom? I don't ever have to work again. If I lived 100 or 1000 lifetimes,

what exactly do I want to do on this planet? And you have to say, when you look at the score card in life, you know, I sort of talked to people about the two scorecards. You know, there's a score card that, you know we can all see from the outside, which is Hey, what do you returns? Hey, you know how famous are you? Hey, how many Twitter followers do you have? Hey, having people download your pockets.

How many people come to your conference and you know it's OK. It's OK to care about the scoreboard. Right? Championships are won based on the score of the game. Absolutely. However, there's another score card that I obsess over, which is how good of a dad. How good of a husband, How good of a friend, How good of an investor, How good of a boss, how good of Ah, you know, brother at arms, Can I be two people in my world,

And how do you manage that? How do you ensure that you don't lose one side of your life whilst the other grows over something incredibly successful? You have

maturity. I mean, is it a lot of maturity that occurs? I think when you're young, I think you're driven by adrenaline. You're driven by a lot of different things that I know a lot of driven people, obviously, and you invested some of them and your drive when you're young. I think what makes young people successful is sometimes a very basic motivation. If you look at Maslow's hierarchy of needs, if you look at the dynamics in the psychology of motivation, competitive motivation is a very immature motivation. It also happens to be perhaps one of the most powerful eso Michael Jordan or LeBron James. They got up for the competition, right? They wanted to be number one. I really want to be the number one angel investor in the world.

I desire that I want to be better than anybody else. Even Chris, aka who is a dear friend, even Tim. First, I'm competitive. I would like to be better than them.

How do you measure your success? And is it the exits your value?

That is really the key questions, and they know that they're Harry, which is what score card playing. By now, there's gonna be the scorecard of returns, and that's important. So I don't know if I could ever catch up to Chris, but I know that in terms of how helpful I am, I know that I'm a helpless Chris, right. In fact, some people might argue that I'm or engaged in Chris or, you know, because I have the show and the you know, because they have the podcast that reaches so many people this week in start ups and have the largest Arctic arms worldwide, Express well, I have a couple of things that he doesn't have right that can really help a start up.

Now here's the thing. Winning at all costs and winning alone sucks Winning on a team. Well, that's magical. So really Sokka and Tim Ferriss Sharma Palihapitiya rule off both Bill Gurley. You know, I've got this list of people. George Zachary from CR V. That's my core group. Siam Bannister. I'd like winning with them. Jonathan Trees from Ludlow. You know, pull Judge Mike Savino. I have a group of Angel LaValle who I just love winning with those guys and gals. And for me, winning is really about winning together, right? So when I see Chris or Tim winning, I am very excited about that.

There, there, my child, get in on rounds

on Dhe, Of course, of course. I mean, listen, I am I'm a cutthroat guy. I mean, people don't see that publicly as much anymore. But, you know, I'm a pretty extreme guy, not as public anymore. I mean, people have seen the fights. They tied cow Countess Ansel into Google. In fact, if you take these guys did a really funny thing,

you know, Google will, like, do the auto fill ending. Yeah. So some group of like you guys is a joke. Like they all just typed in calle counters do sh on. So now you know, like a huge campaign. And now when you type Cal canIs is, uh I think that it's not working anymore. I'm doing it right now. It was pretty funny. Um, you know, uh,

although it does seem like everybody is obsessed with my wife. I'm typing Cal canIs wife Kala cannons, and then wife comes up networth What? Looks like things come in. But anyway, you know, you've seen the public fights I've had, and I tried to temper that down. I think when I was young, you know, I was kind of like I wanted to win a little bit, and maybe I got a little excited sometimes if I felt like somebody crossed me,

You physically restrain yourself, then sometimes from saying something that you really mean?

Not really. I just say it a little differently now, okay? And I might say it in private, but I could tell you, like, right now, this week, I have a company that I think is gonna be the 15 record of my portfolio and I basically I tell all my friends on the point guard I bring the ball down court I, you know, do a nice little alley oop to trim off with with a company called Home Hero and with a company called All Tuition, which became brilliant. And I like to pass him the ball. He knows how to scale these companies. I put my 2 50 I put my 500 K and I put my 50 K and whatever it is, and I bring the ball down court and say, Hey,

Mom, heads out, Boom! And I tossed him the rock. He dunks it, but we both win together. Bill Gurley. Same thing. I was the Angel investor, an uber Bill Gurley to the around. Sherman did the bee. Not that, actually, I introduced him to the companies they got to themselves. But the point is, I do like to bring the ball up the court to roll off both at Sequoia,

I was a second investor in thumbtack. After Marko's parents, and then roll off, I brought him the A round robin. The beer and I were on the seed round and roll off eventually and Sequoia did to be around. So I love that. But there's one VC who is incredibly high profile. And I sent the last three entrepreneurs to his firm and he didn't meet with him.

He was VC.

I can't say, but I'll tell you, like in terms of and this is the point,

I'm gonna see you off.

Does it piss me off? Yeah. You saw the email I wrote to this person. You would be like, Oh, my God, That e mailed ever gets public. If I put it in my book that were like, Well, Cal cats what? Mark? Or I literally

told them, Didn't I know one thing's not already, Jason, No one.

You know, I feel like if you don't stand up for yourself, you know, and you don't, like, make a point of, you know, telling people like, Hey, this is you know how this needs to work. Well, you know, then people are gonna treat your certain way. So I'll read you the email subject line. Deal, flow person, Famous person,

number one, Famous person, number two, famous person number three. Hope you're all well. I've got a killer startup put a $1,000,000 to and it's got a chance of breaking out was going to send them over, but have concerns since the last couple of founders of Center. We didn't have a great experience. They all said. Neither of you met with him. Not even a pop your head in or say hello or greeting the lobbying offer were hand off to a partner. Obviously, this makes me look bad, but frankly, it makes you guys look worse when I send somebody to my short list. Bubba,

Bubba, Blah. They take two time to be with the founders. Personally, I know you're both. I know you're all super pro founder, but I'm confounded by your approach. So anyway felt you should know why I stopped sending you start ups. And this is to somebody

who is loved Jason

powerful than I am. But if I said my founders to you and then they called me back and they say you took this introduction and a company that's, you know, really taking off and you gave them to like a junior partner. Junior partner didn't know why they were in the meeting or, you know, whatever and they just basically gave them 20 or 30 minutes, like man, that's not fucking cool that it's not fucking cool. Like the's air entrepreneurs were busting their ass. I put money into these companies. I'm trying to help them, and I send you somebody in.

But, Jason, I would have thought, considering, you know, you've put money into it. That's validity, that this has got genuine potential. Surely that go how Jason's backed it. We've got to take a look.

Yeah, I mean, listen, I wanna be an egomaniac about it. I don't think that they have to meet with him just because I sent them, But actually, my founder's do think that. So my founder said to me, Hey, why didn't these guys why did these guys diss me so bad? If you set me there and I said, I apologize. I guess they don't think very highly of me, he said, Well, the founder said to me, Actually,

Jason, I think less of them, but they don't take you seriously. You've been such an amazing angel investor to us. The fact that they wouldn't personally they didn't personally meet with us, and you sent us there, and you get uber chart, beat some tax well, front raise dot com All these other companies that have done very well in a row respected, like these people don't get it. I don't want them as investors is what they said to me. And I said, You know, what if I told him if somebody asked specifically for an intro to you of course I'm gonna do it. But if somebody asked me who are the 45 best veces I should work with, I'm gonna send him to the to the chem off to the bill,

Girl, each of the George Zachary, you know, So the people who will actually take the time to meet with them. And when I when I introduced my latest company to those four or five people, they each got back to the founder in under one hour on the hour, some of them replied in five minutes, 10 minutes with their assistance. And not only that, the founder asked me, Should I go to them if they come to me? I said, I always like to gauge interest and let people see what the sausage is made. So what I always say is I would love to have you meet the team and see what we're building. But of course I'm respectful of your time and will come to you for the first meeting. If you want to do that,

all of these guys were like will make a trip. So not only did the other firm not take the meeting and not have their founders take the meeting, the people, I'm introducing them to the other veces they're all racing up to go meet with the person. And some of these people are coming up from the valley to San Francisco to be with the person. Because listen, we we all work together on this is collaborative. Member of said before, like, you wanna win as a team. Yeah. Absolutely. I don't think somebody's a team player. You know what, man? Fuck you guys like you guys were not playing the game,

right? You're calling and rich. You're forgetting who's important in this equation. The founders are the beginning, the end and the be all of what we do as investors. No founders, no

returns. So if you were to raise money for web blocks again and you could choose three veces or Angels. Who would you choose? Is your dream team

what they got?

It's a good one

As Ugo listen, I like partners, not firms, So I would step back and I would do it that way. And then I would also look at who's good at media. Right? So I look at who has back media companies who wants to work with media companies. Who do I want to go to? A meeting with a roll of both has been amazing for me. I would absolutely pick him again. Nivaldo is a close friend. Bill Gurley is a good friend. I love both of them. George Zakaria would love to be on a team with him. 20. Conrad from true. I love him.

I would love to be on a team with him. You know the list goes on and on, and in fact I'm going to do an event and I'm doing my scale event in October. Lost scale dot Net, in which 3000 founders 2500 founders will come for free and then I'll sell 500 people tickets. Who are V. C's and lawyers, accountants, center and service providers. You know, whatever big company people funded people. But I'm gonna do a conference right after that. That will be just me interviewing the top 20 investor. So I'm gonna make my list of the top 20 investors that you'll see. Actually, I think

this will go on this weekend. Sells

ups, Of course, with the best of it. Well,

yeah. Fantastic kid stuff.

Well, that's one of the things I'm trying to do as a podcaster is take the best stuff going on in the incubator, take the best stuff going on at the events and syndicate that to the podcast. So when it seems like 100 4 episodes is a lot each year to a week and we don't take any vacation. You have to remember when I do the launch festival three days, I do probably 25 interviews. We take the top 10 of those based on how the crowd reacts, and we make them into probably eight episodes. Some of them are like, you know, you put two together, so maybe I don't know, 10% of the episodes will launch festival. 10% are the launch incubator, and 10% will be the scale conference and maybe 10% will be this investor

conference and you find one type of episode is more popular than others. So absolutely veces absolutely founders round tables. Is that one that's more important? I'm not more important. More

depends. I mean, people love If you're founder, you love tactical stuff, right? So when we do the tactical stuff from the incubator I get, people are like, Oh my God, that tactical stuff I was taking notes. I watched it with my team Whatever. So that's great. However, some people are like, Oh, you weren't in the episode. It was boring, you know,

because it's somebody else speaking, maybe asking a couple questions at the end. Other people are just addicted to the news broke because they like to hear me shoot the shit with, you know, two or three smart people. Cara Swisher, Sion Bannister, Jessica Lessing. You know, smart people in the program is a group of people who love that. Other people are like, I'm not really into this. I like when you do stuff. That's, um, you know,

a deep interview. So I love when you have the soccer Gary Vaynerchuk, Tim Ferriss, like deep get to know somebody, right? So there's three different categories. Their news round table, deep profile, interview and then, you know, tactical stuff. And then I do it. Ask Jason once in a while. I'll do like a little pitch contest, like a shark tank. Kind of being once in a while.

I like to mix it up, you know, and I think that people like the variety of things. It appeals to different people. Different, different things. So a Zanon emerging podcaster like yourself. I think, you know, getting your skills down to talk to, you know, investors like we're doing right now. I have a real conversation. And that's why people love that. They love hearing from the people who can actually write the check. I know when I was coming up, anything I could understand about those people who were writing checks, I couldn't get enough, you know?

Yeah. And what do you think was the turning point, then in your podcast? Was there a time when it suddenly exploded?

Um, I don't know that there wasa I mean, you have to remember I was doing Internet radio back in 95 with Josh Harris on the pseudo network when he did pseudo dot com. And I was doing the Silicon Alley reporter radio

and I sucked. I would like I would love to say I listen to it, but I was born in 96.

Yeah. So you were born, right? Also starting to do it. Thanks

for making me feel old. Not in today's.

Yeah, The thing is, you know, I kind of sucked back then and then I think maybe for the 1st 102 100 episodes, I was just OK. And I think, you know, I was probably bad, actually. Maybe the 1st 200 wasn't taking it very seriously. It was just me and a microphone, and I'm just gonna, you know, screwing around kind of thing. But I think, you know, somewhere in the middle,

I got a little bit better just by practice. And then in the last, you know, 200 episodes I said to myself, I want to be the best interviewer in the technology business and then eventually I'd like to be the best interview on the planet. And I haven't really made that publicly known. I've said people publicly I want to be the best angel investor

of all time. Have biggest competition than in the poor castings fair.

Um well, here's the thing. I I'm definitely the number one startup podcast reports. Definitely the number one tech podcast. Um, stand then, you know Kevin Pollack, Adam Karol are the best in the immediate one. So I don't know that I'm up against anybody, really? In the podcasting space. I think I'm probably, you know, at the top of my specific game, But there's really not that many people I'm competing against. And you really, if you just the person who doesn't quit actually becomes the best.

So, you know, there's a it podcasting. It's really just about not giving up. And so the people who keep going, you know, if they just get literally 1% better every episode, if you do 500 episodes, you're gonna be pretty fucking good after all, right? And so, um, you know, um, I think I've got a little bit better each time. And really,

my goal is, and this is gonna take another 10 years. It's too. Maybe shift at some point and interview people outside of tech, which you see me do a little bit of flashes of here and there Glenn back and Tony

Hawk. And is that your plan to really expand the market base?

Yeah, I would like to do another show. That is me talking about non technical things and maybe do that on television or do it on Sirius Radio or something like that. You know, we joked about doing the Jason Nation show at some point on DSO. That's what I'm hoping to dio. Great idea. Yeah, I don't have time right now. You know, times my enemy. So when I retire, I think that would be the time. I'll do it.

Andi, what are the next five years for you on launch? What? You have a plan and you're had a career trajectory.

I was got playing, man.

All right, that's what I do in shadow plan.

I'm sure a little bit of it with you, Charlotte? Yeah. So you know, we have the largest conference in the world now. It's 12 now. Some people would like to double that in the coming years, so we double and get to 25,000 people coming over the three days or four days when everyone's being you. That could be pretty spectacular. So I think having the largest one and then having companies. Big companies want toe, you know, launch their products at our event. We have that. Now we have people who specifically are like, When is the event I want a time. My company's launch our next product launch around this.

And so, you know, I think if we can get launched to that level, get inside to maybe being three or four times bigger Now, that would be great. Um, hold on one second. Um, it's a memory from perfect. Yeah, And then, if you know, with this week and start ups, you know, I want to just keep doing it and keep it honest and authentic. I'm not

trying to make it over produced on who you think has been your best interview guests than talking of this week and start up to you. Most enjoy it. If you could single it down to one.

Well, there's what I enjoyed this, what the audience enjoys. So the audience has been pretty clear that they really love the conversations with Gary Vaynerchuk and soccer. You know the most. You know, people say it's

number one of the most downloaded.

Yeah, I think they probably aren't really keep track about too much, you know, for me, um, when I could get lost in the moment in a conversation. And it's like that magical kind of thing. Whether it was, you know, Mark Cuban or Travis. Couple times, David Sachs has been great. Every Williams has been great. Paul Graham was great. I mean, you're just getting lost in the moment. I couldn't pick one.

I could pick a dozen. Everyone's I'm mentioning right now, Like for me getting lost in the moment. And, well, Jackie was great. I was actually really surprised about her. You know, she was really from 23. May I really enjoyed that interview. John Doe was great. Too short. I want to do that

again. Was amazing.

Like a little more time with him. So, you know, I mean, let's be honest, you know, I'm a kid from Brooklyn, and the fact that any of these people even, you know you know my name, let alone come on my podcast. I mean, I'm I'm so thrilled right now. I mean, it's not coming across in my social media in the show and just my general demeanor at the events and stuff like that. I never expected to be here. You know, I knew I was gonna make something of myself.

This is a little bit further than I thought I would get. And so to be 44 be this far along, I'm kind of like Holy sh skip. I might be on the planet for another 40 years. Holy cow. I've only been an adult. Really? For 24 years. I've got 24 more years of adult life, I hope

do you have? Do you ever sit back and see your achievements and go? Wow. No, no,

no. I have a very specific rule about that. I don't take Don't you know, when I was when I was coming up, somebody came to me who worked for me, and they had giving me, like, three or four press articles framed, and I took them all. I said, thank you. And, uh, you left

my office in New York. It's gonna be too. Thank you.

Thank you. Very touching. And then I put them in the closet and they came to me and they were very hurt, Like I want to put them on the wall. I said, I'm sorry. Once I start putting that shit on the wall, I'm gonna start living in the past, and I'm actually gonna think like I'm successful. I don't want to think I'm successful. I want to think that I have to get up today and I gotta do work.

Is that what drives you?

Yeah. I want to be able to just get up every day and work. You know, I want to do good work with the people who I love. And I just got off my team meeting with the inside team, and I sold them all like guys. I'm just so fucking proud of you guys for, like, really fighting the good fight here and getting so much shit done and really like, It's news and building brands and mobile face talking competitive, and they're just crushing it, you know? And they're working really hard, and, you know, not everything's going right. But some things are going right.

And, you know, like you guys were really staying positive and studying what's working? Still, probably guys,

have you always done what you love?

Uh, no. I was a waiter. And what's called a bar back. You're a waiter. The bus boys waiters are got through school. And my first technology, my second job in technologies fixing laser printers. The HP LaserJet, too. So yeah, no, I did stuff of us that sucked. I had to pay my way through Fordham in New York to be five years. I worked three jobs. I was fixing these Apprentice during the day. I was a waiter on the weekends,

and sometimes I would be what's called a bar back on. That is the most in Brooklyn at the salty dog and other places. My dad's restaurant and basically my job was to go to the basement, carry up buckets of ice cara cases of Coors Light and Bud Light and take the bottles and just jam them into the ice and stack them. You know, as people drank and there's been people smoked in restaurants and bars, and you basically got there at, like, five and set up the bar, and then you left at 5 a.m. It was back breaking, and you got paid 20 bucks by the restaurant, and then the bartender would give you 10% of whatever they made, which was another. They make the bartender to make 500 bucks like another 40 50 bucks to make 70 bucks. You know, over 12 hours.

You know, not that much money in our something eight bucks an hour. The minimum wage is 3 50 back then so and it was cash off the books, so it's pretty pretty good that way. But I had to pay my way through school, so I did back breaking shit. Luckily, only do it for a couple of years, but yeah, yeah. No, I didn't like it. What

would you say? That has been the most pivotal moment of your life. For the moment. That's contributed most. Your success,

I think. What? My dad's business fell, you know, when his bar got taken by the feds because he didn't pay his taxes, and I watched him fell when I was 17 and I just thought to myself, My God, I'm never gonna want to fail like that. That would suck Thio, have your business taken by shock guns. You know, the feds for not

paying your taxes, and that drives you on today.

Maybe subconsciously, I've kind of reconciled it, but I think as a child, you know it made me feel very powerless. And it was kind of heartbreaking to see my dad, who was like this larger than life character entrepreneur who owned, you know, one of the premier bars in Brooklyn where I grew up. And everybody knew him. And he was, like, almost like the mayor of our little town Bay Ridge, Brooklyn, tow. Watch him, you know, have everything taken away at,

you know, gunpoint, buff, You know, feds, and then go hundreds of thousands of dollars back in his taxes, and you have to go work for his competitors, you know, on be like a maitre d and manager at, like, shit restaurants. You know, it was like, wow, you know, watching Superman,

you know, go work for Lex Luther and have kryptonite put around his neck really, really heartbreaking for me as a kid. But, you know, since that time I realized, like, wow, you know, he wasn't a perfect guy, but he did the best he could with, you know, You know, it wasn't like he went to India and make it through a semester of college. I mean, this guy was like a hacked entrepreneur. He didn't know what he was doing, but he did some good stuff and he worked hard for his family at times.

Um, I'm watching. It's been most challenging moment of your career. Then,

you know, I have to say theater net bubble bursting and then 9 11 happening like in the same 18 month period. Or so you know, being in New York for both of those events. That was very tough. I mean, that we're really it didn't break me, but it certainly was not pleasant. And I definitely got PTSD from 9 11 and I definitely got, you know, not PTSD from the Internet bubble bursting, but it just wasn't pleasant at

all. Do you have a way of dealing with that? When that happens? I mean, I know your investor in calm.

Yeah. I mean, listen, I do meditate. Yeah, meditate three days a week, four days a week. I think now, you know, as you get older, you can kind of see the arc of your career so you don't let a little thing. So you know you can survive stuff. So like surviving the Internet. Bubble bursting. Surviving 9 11 surviving the financial crisis, surviving mahalo, getting hit by the Google panned update legs 75 people off all the shit.

Like you know, if you survive enough shit in your life, you know, you start to become a little bit fearless about it, and you don't get, you know, super broke out. When it happens, you can kind of stay low level headed. So, you know, I fully expect I'll have to deal with other challenges in my life. But, you know, there's, like,

again picking the important scorecard, the scorecard that matters. You know, how you treat your friends and family and team members and investments. And you know how many great experiences you have with them and what you build with them. You know, whether it's love or experiences or companies or moments, you know, those are the things that matter. So, you know, when faced with failing businesses, it doesn't actually change my pulse. It'll, um, you know,

when you lose a friend and somebody dies, you know, too young, like yeah, or somebody gets cancer. Yeah, my feet are things to worry about. You know, death of a child, depth of really friend, you know? Yeah, this is you know, my one of My friend's father died and is having a tough time with this. Store it up and yeah, it's been rough on him like a perspective.

You gotta really understand. Like, what matters in this world, you know? And, uh, life is short. You want to work with great people, you want to do good work and you need thio. You know, build deep, meaningful relationships with your friends and your family. And hopefully your business colleagues are also your friends. So I don't really work with people. If I'm not friendly with them, like if I don't have a friendship with you,

I don't really need to be in business with you. There's enough people on the planet were good friends with. And you know, Travis and I are breaker friends from uber and have been for a long time. And why would be good friends with him if his company failed and I would invest in his next company. And, you know, if you look at my track record of investing its I invest in people who I like, and if I don't like the person I literally have had one or two people who wasn't working out and I just said to them like, Listen, take my money, Give me my money back. Take your stock back. Will rip up the agreement. I don't need youto pay me whatever the last round was. But way shouldn't be working with each other if we are not simpatico. And

I'm here for the founder's. If they came to you with anything, you'd say yes, you've got it.

Yeah. I mean, I have obviously Travis or Evan Williams. O r um, you know, um, Josh Williams. You know, it's a very long list of them too. Mark Pincus, David Sacks. A lot of them don't need my money anymore. So with those folks, it's more like I would be asking permission and, you know, sort of making my case like, Hey,

can I invest in your company? Andrew Mason. You know, just people who have good with product, like Kralik product. People will go a product like visionary people along mosque, obviously so. But those people don't need money anymore, So really, my job is to find the young people or first timers. They could be 40 years old or 50 years old, but the people who don't have a track record. I don't have a great track record and actually be the guy who believes in them when nobody else does. That's really at the end of the day, my job. My job is to be the guy who believes in you before when nobody else does. And that's what I sent in my career around. It's how dowe I believe when nobody else

does. And talking of Elon Musk you mentioned there. I read somewhere you got. You've got the Tessler s 1st 1st

1 Yeah, I have serial numbers here. Is there? Is there? Is there one?

Yeah. Have you been offered insane amounts

for it? I got answered twice. What? I paid for 20,000 miles on it and some of it for me. 20 $50,000 For

how much would you sell it for? I would never sell. You would

know that I give it back to you on if he wants it. But I wouldn't sell

on then. Then what's the most recent investment you've made and why? Why did you say yes to that? Um,

that's a good question. Let's see. Um, I invested in a company called Bento, which is crushing it I think a lot of people didn't believe in that business, but it's doing delivery. Service is food, and week after week, they're just crushing it. Just there. Bento on Twitter on basically can pick your sides and your main and it's just super cool. And another company that's really interesting. It's called one drop by Jeff Doctors on He is doing, you know, diabetes. So it's worth checking out. One drop,

Jeff doctors. You can just do a search for that. And, uh, well, a lot of things. I'm trying to see which ones I can talk about. I invested in the Hyperloop.

You ever invest in hardware?

Yeah. I'm an investor in a company called Butterfly. I'm an investor in company called Birdie. So butterflies the better drop cam got a server inside of it. It's gonna be huge. Uh, birdie is a quality air quality detector and smoke detectors were sort of like better than nest. Actually cut two competitors, which are both going up against nest. Basically two separate hardware companies. Andi. Yeah, I like hardware. I'm not afraid of hardware. It's different. It's harder. But, you know, it's definitely worth looking

at these days on what's blown your mind in the last month will say,

um, I would say this company Butterfly, what they're doing is pretty amazing. I'm super impressed with drones. Drones are really starting to come

into their own. Would you say, Austin, that expected to be disrupted or to really emerge?

Yeah. Drones, three D printing and virtual reality in machine learning on the on demand economy, these, like sort of trends are all starting to emerge and sort of build off each other and really build up the back of smartphones. Whether it's the sensors in the smartphone to the brought that network or GPS, all that stuff is starting to converge. So you have companies that couldn't exist if we didn't have Samsung and Apple battling it out, making better and better and Foxconn making better and better sensors and chips. So I am super bullish on drones. I think three D printers are starting to really help people who are making other hardware store. It's sort of a picks and shovels kind of thing. And then, you know, I really have never believed in virtual reality until this latest cohort of companies six cents is a really interesting company that's does the motion tracking where they put like things on your head or your wrist or your ankles. And you really know where your body is in three D space and, you know,

obviously Oculus. So I think that stuff is really gonna work for video games and adult entertainment, and it could work for education. So I think it's gonna be kind of mind blowing that you're gonna be able to literally We could put out the training course for how to do hearts are open heart surgery and let anybody do open heart surgery in virtual space without a medical degree. And it might turn out that some kid you know from Pakistan, who has incredible dexterity and concentration, could do the best heart surgery in the world and has no training other than he just she or he hung out in the simulator all day long because, you know, the course was free on the Web and, you know, then we don't need to have a medical degree. You could just go in there with somebody with the medical degree and they could watch you put the stents into somebody's heart or something, because you just have to be so goddamn good

at it. I'm let you sit on education. I mean, I know peace t

overseas should shitty, shitty place to be as an investor, it just never works out. Um,

do you think all those degrees unnecessary?

Of course not. Yeah, they're disaster. College is the biggest rip off of the planet. You know, that's that's That's probably the I just talked to my brother and, you know, help my nephew a little bit with his college education was like, You know what? He's gonna be $160,000 into this degree. Do you think we should have just given him 10 k a month or five month for 30 months, two or 32 months to just start a business and learn on the job and just lived in Manhattan for $5000 a month and buy him the equipment to start a business? And I know for me, I would have for that. So I mean, I did it because I have the money to do it. I'm blessed to be able to help with that stuff,

and he's got some loans and stuff, but, you know, Holy shit like you should not spend more than $50,000 on college unless you happen to be rich and don't care about the money. But you know you should not go more than 25 k in debt. I don't think you should go more than one year salary and death. You're gonna have 40 years of working, maybe 30 years of working. Whatever it is 30 40 years of working 50 years of working, maybe one or two years of salary into debt. So, you know, if you could make $50,000 when you get out, maybe go 50,000 into debt. If you actually learned a trade school, maybe 100 today.

Just remember, if you start making 50 K, you pay 15 in taxes. You know, you have to get to maybe 100 k before you start paying off his loans and it's indentured servitude. It's complete joke.

Why did you sit on Bitcoin? Obviously it wasn't one of the ones you suggested that, as you

know, I mean, I wrote about it for anybody, and I should have bought it at a dollar 50 cents. Whatever was trading when I wrote my piece you know, the world's most dangerous currency on DSO. That was a miss on my part. Stupid one. You know, obviously the Blockchain and some of that stuff is very interesting. I think Bitcoin has an equal chance of going to zeros. It does $2000 again. I think it could be like the first person up the hill who fails. You know, it could be the Mosaic browser Netscape browser, where, like,

you know, the Web is super important. And the Netscape browser, you know, in most a browser and what Mark and rescinded there was super important. But it doesn't exist anymore. I mean, eXistenZ Mosiello, maybe. But, you know, sometimes the first person who goes up the hill gets all the arrows and dies on DSO. It might be that stellar, you know, is you know, the next one up the hell,

and they make it work because they're a nonprofit, I don't know, but you know, I have to say it's kind of embarrassing for all these V C's and founders that they can't make this product mainstream or find a decent application for other than speculation or money transfer across borders. They really need these founders kind of suck. I mean, really, the founders in the Bitcoin space are not doing a great job. I mean, I think they're all hype and very little execution. And what

do you think of evaluations, then? E I mean, in Bitcoin and in general, do you think they are massively inflated?

Everything's inflated. Yeah,

it does not put you

everything's inflated. Well, you know, Listen, I'm in a unique position because I had a lot of value, so I can sit and have a conversation with an entrepreneur. Say, Listen, I know you can get $8 million from dentists for this company and, you know, dentists and douchebags funding your company, you know, they

weren t g Jason Calacanis,

D is it? No. But seriously, like, you know, I met with a bunch of y Combinator companies, and I'm like, What's your valuation? $10 million. I'm like, Okay, great. Um, you know, thumbtack and uber. You know, they were $9 million like,

Well, we only want $1 million. Morris, like no, no. Combined. Their valuation was nine million combined when I invested in their first rounds. And you're nothing even close to either of those companies at the time. You know, I think like the y Combinator cos it's an incredible program and the mentors there are fantastic is a lot of great people there. Obviously, Sam is awesome and Gary's awesome got so many amazing people, their programs awesome. But we gotta get these valuations to somewhere close to reality. And then I think they're getting the shitty investors because you go to Demo Day and you know, the founders were trying to put pressure on me like we have to close.

We're closing and we want you in and I'm like, That's not how I invest. I want to meet with you for two or three weeks. I wanna have lunch. I want to see a product. I want to meet the team. I want to talk about the plans. I'm not just gonna just give you $250,000 be your lead and not do any diligence. I'm a value added investor. This is my job. I take the shit seriously and so you know, a lot of these guys are like we just want to close fast a high valuation on my great muscle talk. Go for it. You can come see me when the value when it doesn't work out. And your investors are a bunch of dentists and they don't know what they're doing. And they've never run a successful business.

But they've got money, you know, I think they're optimizing for the wrong thing. Let's face it, you know, there's many more unicorns outside of, um, there's many more unicorns outside of y Combinator in it. So I don't need to, you know, invested y Combinator cos I think for a lot of angel investors, that is the best place for them to put their money. So an index fund of why Combinator companies would be a great thing if you could get in on it, um,

security from investing in accelerated stall subs.

I have my own. So, you know, for me, I would rather just accept people to mine and work with them. And so in my accelerator, we only have seven companies. I we have 18 classes and I come to 14 of them, you know? So if you look at Dave McClure or Sam Altman, you know, a program, I think you might get us a start up, you know, you might get to meet with him once or twice or something. And you're one of 120 or 50 companies per cohort. I've done kind of the opposite.

I'm like I say no to 20 cos I want to accept, and I just take the seven. And I spent a lot of time with him. So they get like, you know, a lot of Jason time. We're like, if you drag y Combinator, how much Sam time do you get? How much time do you get with Paul Graham? Probably very little, Um, why

don't you make it then? Dave McClure is spray and pray approach to investing.

What hasn't worked hasn't. Well, I mean, I think he's been pretty open about that, that, you know, he hasn't had a bunch of Unicorn champ. But I think Dave is learning very quickly what works. And I think he's got a, you know, a scrappy team. And I think if they can maybe I think they would be twice a successful If they did half assed much. That would be that. That is my advice. It Dave do half as many deals, but do them twice as well because I think one of the things is that the, you know,

I'm kind of not competing with Dave. I'm not competing with y Combinator. You know, I kind of work with them. Their founders are calling me to invest, so I don't It's not like I'm competing against them. They all want me in their deals, and I want to be in their deal. So it's collaborative. It's not like, you know, um, it's not like we're in competition. But I do think that 120 companies at Y Combinator and whatever Dave's doing is it's just it's not good for the startups. I mean to sit there as a startup and b You know, let's say you have three founders from the start up at a y Combinator talk with,

you know, even if they got like, you know Khosla are Michael Moritz or something made this incredible speaker. That speaker has no idea who's in the audience. There's 300 people. There's 120 companies, whatever it is, you know, those companies would be better served if there were just, you know, 20 companies and then the speakers came and at least got to know five of them or seven of them, so that my incubator, all seven companies, present all seven weeks to every speaker, and I have three or four V. C's and angels come each week.

So you know, my my entrepreneurs and my founders were getting d. I would save chips they're getting for 50 to 100 times the value as a y Combinator company for a tech stars who are maybe not techstars, cause I think that it's the class is small, but it definitely 50 times more value than a demo than a than a 500 startup y Combinator company in terms of the program. But I would say that why combinations program does triple your valuation and mind probably only doubles it. You know, I guess I could have a triple

it if I was entailed in your incubator. I mean, how much do you invest for? How much accuracy is it? Generally speaking,

I wanted putting about 2 50 in, and I wind up owning about 10% of the company's, maybe 7 to 12%. It varies a little bit so,

and how do you like founders to connect with you

e mails most efficient

okay? No, no, not on Twitter, Arlington

or any other you're talking about Founders? Who are?

Yeah. Found Thio essentially pitching

T. Yeah. I mean, I've written They should read my block and then watch the podcast. They should come to the events. If they do that, they're gonna figure out howto most effective ways to get to me. If they don't do that stuff, then it's like, Well, if you're you have to study your targets, right? Like so I study the founders I'm gonna go meet with I know where they grew up. I know where they went to school. I know what their companies were before. I go to my research before I meet with the founder. The founders,

sometimes they're meeting with, you know, Chris aka and they don't know he worked at Google or their meeting with Dae Bak. Or they don't know he went from PayPal. Like, you should know everything about Dave Makor before you go meet with him, right? Founders nine times out of 10. Just do not do the right work

on. Then when you think of success, okay, Who is the one person you think off? Do you have an idolatry Image in your head.

Well, you know, listen as an entrepreneur, hands down. Musket is, you know, the gold standard. For sure. Steve Jobs was amazing, too. But you know

what? Did you learn anything from being with alone?

A lot? A lot.

Was your number one takeaway

e think he has a fearlessness? You know, he's got a fearlessness that, you know, would make him, like, almost like a superhero or supervillains like he's just too. He's got way too much fearlessness. You know, like, I almost feel like sometimes, like, grabbing the guy and being like, um you want to think this through, you know, like, Okay, so now you're gonna build enough batteries to power every home in the world.

Are you sure you want to go into space with no experience?

Yeah, but you know what the thing is, I think what? The beauty of how he behaves and how he carries himself. Is that what he said? Some to be maybe close to 10 years ago? He said, Jason, most people overestimate the downside risk. And that always stuck with me because, um, you know, he almost came close to failing, but he would never have the success he had if he wasn't willing to go to that edge and just looked down at like, Wow, there's the press. If it and oh wow, look at all the great white sharks there. I'm going to run full speed to the edge and that hangover with one foot and see if I don't fall into the shark pit. You know, like that

crazy. You know, would you say you've adopted that fearlessness

to know I try to, but I don't have anything close to him. I don't know. I don't think that what I think. His fearlessness is inhuman. I think it's like he's got something chemical, you know? D n a. Just something in his upbringing. I don't know what it is with the guy, but he has a fearlessness that I have only seen in a couple of poker players. A couple of extreme sports athletes, you know, he's like that kid who is like free climbing, you know, with no ropes up El Capitan or whatever that is you know faster than anybody with no ropes. And it's like you sure you wanna do that?

Thing is, this is like, you know If something fails in business, you can always start over. It's not the end of the world, so I think he's right. I think the kid is climbing with no rope is an idiot, and somebody needs to smack him and say, Guy life is worth living. You know this using a rope, you know, it's still possibly dying. Even though you're using a rope that's okay to, you know,

do you think he can do with Tesla's? Do you think Tessa will be

the No? Yeah, it's it's that he's got that dialed in. I mean, when your second car is the greatest car ever reviewed by Consumer Reports. You know, that just tells you something, you know. And when you build a rocket that it's like, you know, half assed cheap, as the people have been at it for 50 years, I mean, it should

just tell you something about its execution. What an incredible episode. I would like to say a special thank you to Jason and his wonderful helper Jackie. On a huge round of applause to my own Jackie Hand delivered by the fantastic hiring screen who are actually offering a special deal for all 20 minute VC listeners. Check it out at www dot hiring screen dot com. The 1st 200 get the deal. So be that on all the show. Notes, as usual, can be found at www dot the 20 minute VC dot com on I look So forward to hearing what you think and seeing you'll and next absolute.