Episode 2000! Epic guests, huge news, and how to build a media legacy in 14 short years | E2000

0:00really it's show 2000. I mean, it just goes to show you what being too stupid to quit will do. You'll just put up numbers. This Week in Startups is really focused just on tech, and it's very focused for the entrepreneur. You know, we don't try to make this into, you know, something it's not. It's supposed to be about startups and really inspire people to get in the game and to feature those stories of great startups and the news around them. I've tried very hard to keep this what it is. J. Cal, 2 ,000 episodes of Twist. What a monumental waste of time. Let's get on you, though. Congrats. Oh, it spreads like these.

0:45This Week in Startups is brought to you by Squarespace. Turn your idea into a new website. Go to squarespace.com slash twist for a free trial. When you're ready to launch, use offer code TWIST to save 10 % off your first purchase of a website or domain. LinkedIn ads. To redeem a$100 LinkedIn ad credit and launch your first campaign, go to linkedin.com slash thisweekinstartups. And Brex. The financial stack founders can bank on. Brex knows cash is king for startups, so they built a banking experience that takes every dollar further. Get the business account trusted by one in three U.S. startups at brex.com slash twist24.

1:30All right, everybody. Welcome back to This Week in Startups. I'm your host, Jason Calacanis. And with me, my co-host, Alex Wilhelm. He's Alex on Twitter slash X. I'm Jason. At mentionist, say hi. At Alex, at Jason. Tell us what you want on the show. Tell us what you like about what we're doing. And here we are. What's on the docket today? Well, today is a very special episode. This is episode 2000, which means that this show has produced enough video commentary to last a lifetime. Really? It's show 2000. I mean, it just goes to show you what being too stupid to quit will do. You'll just put up numbers.

2:09My God, it's been 14 years of this, and I just love doing it as much today as I did for the first 220 or two episodes. So, wow, 2000. That is pretty extraordinary. 2 ,000 is a lot. And I know that it's a lot because on my last show, we got up into the hundreds of episodes, I think like five or 600. And I was on 90 % of those probably overall. And that was a six, seven year project. And so I understand the work that has gone into this. So we have a little bit of a celebration today. We're going to go over some old clips. We're going to talk about some funny moments. We have some recent news. Slight focus on stuff that's more recent, but we're going to start by taking people back to the very beginning.

2:46We have a little bit of a montage put together for you. So Jason, sit back. Oh, how nice. Please enjoy this short intro to All Things Good in episode 2000. Okay, here we go. I'm so excited to see this. Hi, I'm Jason McCabe-Calacanis. The concept here is pretty simple. This Week in Startups.

3:13What does that mean? Every week, you guys tune in at ustream.tv or thisweekinstartups.com. and I have a guest, somebody brilliant, somebody doing something awesome.

3:28I interview them, we talk about what they're doing, we talk about the market, we talk about the epic battle that is being an entrepreneur.

3:42My first guest is a dear friend of mine. He's been my partner and my lifelong friend. So please join me in welcoming Brian Alvey, the CEO of Crowdfusion, to the show. Thank you very much. There he is. Psyched to be here. First. First guest.

4:01I'm JCBK of Calcanis for This Week in Startups, and I'll see everybody at Wolverine tonight. Bye-bye.

4:09So very nicely done. Wow, that is so touching. that is a a an overview of everything but we need to to really narrow our focus for a second jason and talk about this early intro you had that featured new york city because i want to hear the story behind where the hell this came from all right court hit it here we go today on this week in startups sal khan of the khan academy joins us via skype your place is in the shark tank is it a great concept or just bait and our very own kathy choy is going to read the news coming up right now on this week in startups

4:43Hmm. Yes.

4:54Hmm. Rule. Yes. you yeah money is the move of all yes funny how it feeds my people yeah we ain't gonna live like people so tell me get the money spend the money and defeat you all right you can tell it's a little uh dated because i don't think we'd say get off the bitch train anymore no probably not it was a different era 14 years ago one of the producers we didn't have money one of the producers was like i found some i think the that song was either in a stock library found it and uh contacted the rapper and uh they let us use it i had also used um some kanye west tracks and stuff like that and then podcasting started to come up on people's radar yeah at that era podcasting was only at that time um available if you had a pod catching software and an ipod is before the iphone existed this podcast started i think i think it was right before the ipad exists the ipod existed and so they made that and i had just moved to los angeles from in like yeah 2012 or 20 no sorry 2003 or 4 i had moved to la so i was kind of known as a new york guy in la and then um i decided i would do a series of shows this weekend and try to help other people do this weekend style shows like leo was doing this week in tech i was doing this week in startup somebody else was doing legal somebody was doing photography whatever and so i was like oh maybe i'll just get the domain in this weekend and i'll just anybody who wants to do a show will it be like a unofficial network kind of situation but you know the show was the one that lasted the test of time while the other ones got retired if you ever wanted to go see what those other shows were go to twist on youtube click on videos sort by oldest and there is an amazing plethora of content there is this week in movies this week books there is a huge amount of stuff that i i couldn't go through all of it because there's not enough time but i was impressed at the depths of the archive which jason takes me to uh another clip that we have i want you to explain to everybody where this live show was and your level of pride at having about 30 people come because this shows like you were early on the podcasting front now the all-in summit and so forth but here's an early live show okay here we going a live show okay there's a kanye so let's take a look at the audience we actually have a live audience here there they are yes there they are that's a live audience whoa and uh great you're you'll all get a uh tesla uh delivered to your house so you're all set people like the tesla Okay, very good.

7:42Beautiful. And to the people who are in the live chat room, you're going to get a Tesla 2. So you can go ahead there and... Look at that swoopy hair. I think that's Matt Mullenweg, right? Yeah. But where was that event? That's a baby Matt Mullenweg. I have no idea. I literally don't know. But at that time, 14 years ago, Alex, and you were in the industry, I think, at that time, right? In 2012-ish? 2011? 2011. just out of college yeah just out of college and you probably it was kind of hard to not know me at that time because i said yes to every single speaking gig i said yes to any invite to a party i think i it was 14 years ago my daughter's 14 so this podcast kind of started when i when i had uh my daughter and who's 14 now so you know at that time i was just i would be everywhere My philosophy was be the brand, be everywhere.

8:40It's an early philosophy of mine. So I always were back in the Silicon Alley reporter days, a Silicon Alley reporter t-shirt in New York. Then I would wear a This Week in Startups t-shirt. Just try to get people to give me some attention, to try to get something going in my career because I was an up and comer. Yeah. Well, I don't know if I ever told you this, but I actually went to very early TechCrunch events when you were still doing it with Michael Arrington. Yes. TechCrunch 40, TechCrunch 50. So I actually knew about you when I was very little. I think probably like late high school, maybe just because I was in the audience when you guys were out there kicking off, you know, the tech industry.

9:17Isn't that really long, skinny building in San Francisco? Yeah, it was that building, that building got torn down for apartments, but it was the San Francisco Design Center. It was just a giant warehouse. And so, you know, at the time I looked at this podcast as a way for me to meet people. And I was a tinkerer and I had done Weblogs Inc., the blogging company. Sold it to AOL after 18 months for$30 million with Brian Alvey, who was on the first show. And so I went from being this journalist to a millionaire. And the only reason I bring that up is because it was very rare at that time. I don't care if you're building enterprise SaaS, a verticalized AI startup, or the next great consumer app.

9:57No matter what you are cooking up, you have to have a brilliant website. It's the first thing that people see or read from your startup, and it has to be beautiful. you got to make a great first impression people do judge a book by its cover it's that simple that's why we have that expression but since you're building a company you're strapped for time you know that and wouldn't it be nice to have some world-class help how about a beautiful website built to your specifications quickly and easily it's 2024 if you don't already know hdml css and javascript that ship has sailed get on squarespace and check out their blueprint ai product you answer five questions and squarespace's new ai tool is going to build you a gorgeous website it's so simple it's so slick it's just brilliant it's the future even better you don't need to worry about what's under the hood analytics seo payments memberships e-commerce you can do it all it's all included too so here's your call to action check out squarespace.com twist for a free trial and when you're ready to launch go to squarespace.com twist to get 10 off your first website or domain purchase that squarespace.com slash twist and to do a 30 million dollar sale there had been only a handful of those um a flicker to yahoo the photo sharing site delicious the bookmarking site weblogs inc and you know at that time in gadget weblogs inc and gawker were like two of the biggest things and then mike errington had obviously started tech crunch out of his house in atherton and he was very enamored by me and by weblogs inc and the success we had and he was obsessed about the fact that i was able to sell an 18 month company for 30 million dollars he was always asking me how i did that um and i you know it's like just being everywhere and he took that advice and then he said would you do an event with me and i said yeah i have this domain name 20.com let's do an event where we just pick the 20 most interesting startups and we have them show their products on stage we got so many people that it became 40 then 50 and then I wound up selling the 20.com domain name to somebody in China for a bucket load of money.

11:58I thought that was one of my best trades ever was buying that domain name. But that's really how it got started. And then some of the early episodes Mike was on, and I would do them from Sequoia. My friend Ruloff had just started there. So there's all these weird episodes early on of me trying to meet startups to get them at the conference. And that really is what triggered Sequoia to start the Scouts program and asked me to be a Scout. it's what triggered uh at the time david sachs was doing um a website called genie which was like do your family tree but then he did uh yammer as a facebook for inside your organization and he said i have to win tech crunch 40 and i said okay and my wife who we were friends socially and uh said he has to win and so i basically coached him on how to win and then he won and then he said you know jacal you're stupid i sold this thing for a billion dollars you were a key part of it you could have angel invest whatever you didn't you should start a fund and uh i started doing the angel investing with sequoia and uh i was the first syndicate on angel list so i kind of realized wait a second i was doing media but there was this investing thing and i had this great sort of moment where i was like wait a second whoever meets the most people and is the most helpful to those people will get first shot at investing and being on their cap table and when that got fused this random act of journalism i've experimented with podcasts because i had done blogging that's where this whole cycle of i said wait a second what if an investor had a blog what if an investor had a podcast now of course that sounds incredibly quaint 14 years later where every vc feels they need to tell you like their position on ukraine and trump and biden and every single thing going on in the world but back then vcs didn't talk they were not available no the concept was to not be available and they avoided the press so it was very innovative at the time to to to merge these concepts and it obviously served me very well early on though the show did have some of its uh tenor that it has today you were at times even early on very acerbic and i i pulled out one of my favorite little um oh no early baby jason riffs sorry about that.

14:05I apologize for my acerbic nature in the early days of the show. Here we go. This is a message to Y Combinator Companies and hopefuls. If you tell Facebook about your startup before you reach critical mass and you get involved with Facebook in any way, you are an idiot. They will steal your company's ideas and try to get you to take a small price for your company and vision and take a job at Facebook, which by the way is going to be a job that sucks. don't do it it's a scam it's a trap it's a trap it's a trap insert star wars clip here it's a trap it's a trap that's pretty funny so what was the context there jason okay so the context was paul graham had started white combinator was in the early days probably in the first this is single digit cohorts but uh zuckerberg you know had started to become prominent 14 years ago and he said he was going to invest in and that they had a special relationship and you would if you went to y combinator part of going to y combinator was you got to meet with zuckerberg's team and have access to their api to which i said listen this guy has stolen every idea he's ever done he's stolen do you not see this this is the stupidest thing ever and i kind of got into it with paul graham a little bit this is when paul was actually running the thing and people knew i was right it turned out i was right it's pretty obvious advice but at the time i had a big passion for you know what i felt were some things that were unfair i was also that way about something called coretsu forum where they were charging founders five thousand dollars to pitch at these events to supposedly investors and that was the origin story of tech crunch 50 which became when mike and i broke up became disrupt and then i did something called launch festival and then launch festival became the launch fund so it was actually very it was one of the greatest things that ever happened when i broke up with mike because mike had some dark turns personally but uh it allowed me to soar and not have his negativity and toxicity associated with my brand and then i was able to just really thrive with launch i just find it funny that i've spent a good chunk of my career at tech crunch crunch base and now i'm not i'm working with you here it's just a few following in the uh the aftermath as it were um now the acerbony point you being slightly spiky with your language is not super rare.

16:19I found this a really excellent clip of you meeting someone for the first time and having a conversation about geopolitics. Oh. So we have somebody in here. You one out of the ten people here in LA. What's your name? Yu Kai Chow. Yu Kai Chow. Yes. Is it Chinese? Chinese. From Taiwan. Oh, from Taiwan. Yes. Well, that's not China. Well, it's Chinese. Nationality. Depends on who you ask. Yeah. Okay. That's pretty funny, actually. Again, that's 14 years before people started talking about the issue no no i know i just i i was watching through old segments and i'm like i feel like we're having that conversation now about taiwan versus trying to the natural status um but why were you having guys off just randomly coming in on the show from la at the time well okay so back to you know people right now see me as somebody you know who's at a peak right in terms of networking and my social circle so you got to remember back then you know my social circle was a lot of the same people but we were all starting our careers it was very early in those days so you know elon was an investor in tesla and trying to fix it because martin and the other guy were driving it into a cliff and he had just started spacex sax didn't have craft ventures he was doing like i said uh yammer and genie and so and there really weren't that many startups around so i would do on fridays an open call and i'd say anybody want to pitch me their startup i'll give you some feedback come on the show and people would line up outside of my office in santa monica on colorado avenue and um in the order in which they got there we would bring them on air and you see lon harris there who is a producer on all in and one of my dear friends and comes on this podcast to this day just a great human being who have i worked with for two decades now and uh tyler crowley was my kind of body man at the time like chief of staff ish he would travel around the world with me but he would be in the show too because he was an engineer and could do sound and he used to do something funny called insights from tyler who would say inappropriate things that would get you canceled and then we'd play a jingle insights from tyler and the show had a much more kind of howard stern charlie rose hybrid to it and it's different than my style now which i would just say is my own style which is fast talking new yorker you know really uh you know at least i like to think deep knowledge and history of tech and business because as you know how many years have you been john was not 15 15 give or take yeah and so you know when you when you start getting to 10 15 20 25 years of consuming producing digesting debating news man it's almost like getting to year i don't know it's getting to poker hand 1 million it's getting to playing the song in a band you get your 10 000 hours pretty quick right and then you get to 20 000 30 000 hours you know you basically can pick up a guitar and talk about and play any song you know and so but in those early days i was figuring it all out i was trying to be informed trying to trying to keep up with stuff you know and so that led to a little bit of a more and nobody was listening and there were although there were advertisers very early on podcasting at that time was an offshoot of blogging so because i had the blogging company adam curry and dave weiner had worked on this new concept because adam curry was a radio guy and he actually was very influenced by harold sir and he actually lives near me here in austin and he um became known as the pod father and dave weiner created the rss standard which is the standard by which really simple syndication a blog goes out and you can shit in a blog catcher or you can just you know scrape it into a search engine and all they did was add an attachment and a link to the url of the file and then your rss reader which was a specific type of app back in the day would download that mp3 file and it was awesome because it was magic all of a sudden you just the radio show you were listening to previously was on your computer or on your ipod and it was just like this very magical moment of like you take it for granted now that you know because you have smartphones that are high speed connected we didn't have high speed connections at that time you had to plug it in with a cable download all the mp3s and that could take 10 15 minutes to get your podcasts onto your phone and then you would get on the bus or subway and listen to them and so it was like this very you know low thousands of people low tens of thousands of people were into podcasting and everybody thought podcasting would fail and it would be the end of the world it would never become mainstream if you're a b2b startup linkedin should be your top marketing channel why because the business marketing playing field is tilted against you big companies will always outspend you so your spend needs to be 100 dialed in it's got to be very strategic you need two things right you need the right prospect you can have a good target and you need the right way to reach them and linkedin has 1 billion members of which 130 million are decision makers and 10 million of those billion members are the c-suite executives that really drive decision making and that you want to reach in many cases so linkedin ads gives you that ability to target them with pinpoint accuracy maybe going after cfo cto cmos chief revenue officers so build those new relationships while reaching customers when they are ready to receive a business message not recipes or dance moves and you know what you're not going to overspend here because in the tech market linkedin generates two to five times higher roi return on ad spend than other social media platforms and you're not going to be alone 79 of b2b content marketers said linkedin produces the best results for paid media and that's in a very competitive market so start converting your b2b audience into high quality leads today we'll even give you a hundred dollar credit on your next campaign go to linkedin.com slash this week in startups to claim your credit that's linkedin.com slash this week in startups terms and conditions apply linkedin the place to be to be podcasting has gone through, Jason, several waves of peaks and troughs.

22:34But I'm glad you mentioned the guitar in that last segment, because in the next clip, we have you doing a talk show impersonation, and there's a guitar on the table, and a very special early guest. Oh, here we go. Why, at least, did you feel compelled to start a company at the age of 18? I mean, I didn't feel, like, compelled to start a company. I was tutoring SATs. The first person I tutored went up by 400 points. Oh, wow. I was tutoring everybody in the neighborhood. And then one of the fathers said, let's start a company. So I created the course. I hired the teachers, trained them and did the like 1500 and over course.

23:12The 1500 and over course. Yeah. So that was when it was on a 1600 basis. Sure, sure. 800, 800. I love that clip because one, you changed your desk setup and had this like news Walter Cronkite type thing going on there. With a weird angle. Yeah. We were just making it up. We were literally making it up as we went along. Well, the best part is you look totally ensconced and then there's Travis Kalanick just sitting there just off by himself. But you had props all over the side. What was the prop idea? What drove that? You know, we decided, I decided early on and I'm very glad I did that I thought this might turn into something.

23:48So I have a system in which I build a project. I just imagine it's going to grow 100x. It's going to grow 10x, 10x, and then 10x again. and so 10 times 10 100 100 times 10 a thousand you know i just or whatever a thousand times a thousand whatever i just assume that something's going to work out and if it does work out well what would you do differently at the beginning and so one of the things was i said can you just get a couple of cameras and record this and they were like yeah we can do that but then what do we do with the files they're giant i was like well i don't know burn cds and we started burning cds and i said well let's put them on ustream and then somebody's like do you know that youtube is free and i'm like okay great we can just store those on youtube we'll just store them we'll use youtube for storage yeah free storage because i had no money at the or i had money but you know i was very conscious of the spending on this thing and so luckily we set up the cameras but nobody really watched on camera because we would only we were doing it live so back to you and i doing youtube live back then we were doing it live so that we could have a copy of it and that's why some of the early versions look very grainy and you you can't tell you know it's like well what's going on here did you record on a vhs tape and it was like pretty close to a vhs tape you stream at the time but also do different standards i mean back then no one had a 4k you know camera that does video in their pocket with you know built-in like stabilization you had no cameras on sticks and cables and tapes and it was more of a craft back then but i want to stick to that era because you had another guest on that's been on several times that i thought was fantastic but it does show again, this era of Jason trying to be essentially Leo Laporte with more hair.

25:21All right. Yes, here we go. You just rattled off the A-list of companies, Instagram, Uber, Twitter. How did you close each of those deals? How did you wind up being an investor in that cohort? I mean, there are other investors out there who would kill their grandparents to get that, you know, investor list. It's not patricide. What do you call it when you kill your grandparents? I don't know. Grandparents. If somebody could send that in to you, that'd be helpful. But I'm serious like you rattle off these incredible lists of people you've invested in but these other vcs can't get in on those deals how did you get in so early on so many deals like that so you want to take me to each one you want to know how i found twitter please uh evan williams who's been a buddy of mine for a while it was a product i was using i mean i was an early user but evan williams called me up and said hey i'm just closing up the round for this company i got you down for 25 25 okay great 25 hung up the phone and i said to myself i don't have 25 000 i don't have 25 000 like it would be incredibly incredibly irresponsible for me to take the the little bit of money i had at the time put 25 000 in what time frame is this 2006 so this is uh 2007 i think they actually did that now i've worked at google but if you know my full biography i lost a metric ton of money in the spring of 160 and um and keep a running tab please i i lost a lot of money in the spring of 2000 it took me all the way back to 2005 how did you lose all that money um a trading problem yeah yeah i had a big big levered trade that went upside down i like it how you go oops and by the way i looked about he went 16 million negative wow soccer yeah that's a hole to dig out of you know he had a lot of gamble in him at that time um when you hear me rattling off 160 bucks we used to charge 10 bucks a curse word we had a swear jar that we put the money in and then i would give it to the producers because i wasn't paying them i don't think or i would just give it to them to go take go out and go drinking on friday night after the show i'd give him the money so chris soccer ran it up and then one time he ran it up so high that we're giving it to charity water and then i didn't have a lot of money at the time he's like okay we owe three thousand dollars to charity water and this guy charity water starts chasing me for three grand he's like you said it on your show and i'm like okay i'll get it to you i got it to him but it was i thought he was joking i mean earlier on we saw the clip that you promised an entire room of people teslas so now i'm very curious everyone received their tesla or was it more like absolutely the funny part about that was i was also very well known uh because i had the 16th tesla and it was the second one in la elon had his i had mine and that was it um there were only a hundred of those made originally the the tesla roadster so you know and they were producing one every two or three weeks so when you got one there was literally a website tracking each person who got one and it was you know it was a who's who let's just say uh who got them so i would take people for rides in my roadster so i parked the roadster outside of my office and i would tell people it's there i tweet the picture of it or whatever people would come from all around they would drive there to see it and then i say if you want me to take you for a ride just knock on the door and sure enough people would come by and i would just take them for a ride in the tesla and so there's a bunch of people who are like yeah jason took me for a ride in his tesla back in the day because i was trying to get people to buy them because the company was going out of business and i would be like elon i got another person to buy one these person put a deposit down but thanks jacal and you know that's that's how friendships start you know somebody does somebody really needs help it's hard to imagine anyone needing help but at that time you know the cars weren't exactly moving yeah you know it's a pretty expensive toy and yeah help move a couple of cars that really fits into the the theme that i had when i was watching that kusaka clip is that just tech felt smaller back then it was chris like ev called chris was like oh you're in for my company click it felt like there was like i don't know and 25 nothing you know nothing yeah uh but it's like there was like you know 50 companies and like 500 people whereas now i feel like there's 50 000 companies and 50 million people which is good to be clear like more entrepreneurship more founders but yeah he doesn't have that clubby feel to it anymore that they used to know you know and it was so clubby that it was almost like the the dawn of rock and roll or something in that web 2.0 era after dot com everybody thought it was over so anybody working in it who was tinkering in 2004, 5, 6, 7, 8, if you were tinkering around that time, you actually really dug the technology.

29:37You were into it, right? You weren't doing it for money because there was no money to be had. You would have little weird things happen, like my blogging company get bought, but that was like, that happened twice a year. It happened like, it was very rare that something like that happened. And yeah, it was a much smaller industry for sure. and then the dollar amounts were very small you know uber's first round they raised like a million two twitter probably raised a million and it was you know 10 angel investors 20 angel investors 25 to 100k a pop you know and if you could and people were getting paid you know i don't know 5k a month draw 3k a month you know it was so different that you know if you would be a developer at ibm making you know 80 000 a year and some startup would offer you to work you know more hours for 60k a year for 5k a month right and that would be an expensive developer at the time developers were 60 70 80k and you just tried to get a developer and an idea and build something hey when founders ask me what corporate card should they use i automatically think of brecks that's what i use and when founders ask me where they should store their cash well of course i'm going to think about brecks why do i think about brecks so much because knowing everything about your money is not negotiable nearly 40 of startups that fail well they fail because they run out of cash and 100 of startups can't afford to make financial mistakes we all know that so you want to be on top of this stuff and thankfully brex has built a killer banking experience that helps you take your dollars further and they'll protect your cash while extending your startup's runway how do they do all that well they offer the best parts of what you need checking treasury fdic insurance and they do this all in a single powerhouse account if you need the best because you are on to something big a brex's banking solution is going to get you 20 times the standard fdic protection through program banks and industry leading yield on your cash and the ability to send money worldwide at lightning speed which given how global everything is now is super important so brex is used by one in every three u.s startups as you know because you go out to dinner with other founders and we talk about it so go get the financial stack that founders trust at brex.com slash twist 24 brex b-r-e-x dot com slash t-w-i-s-t two four i keep hearing stories from people in the 90s that were like yeah we raised you know a five million dollar series c and we spent three million of it on servers and i'm like oh well that's a different that's a different era but the podcast jason throughout time has mostly been about startups and mostly about tech but occasionally i think you've actually used this as a platform to get people you like and want to talk to to come talk to you and the next clip i think is a good example of uh just that and if you don't know the band the smashing pumpkins well oh yeah here's the drama what is it like you in the room take me to that moment where you write one of these things or you're playing it you know it's absolutely like that you just know you know So Tonight Tonight, for instance, Billy woke up in the morning.

32:42Tonight. He sat down at the piano. He wrote the song. Tonight. It was downloaded into his body somehow. And his whole thing was like, he's simply the messenger. He would get the download. He would create the song. He would bring it in. We literally, he wrote the song in the morning. I conceived the drum part that afternoon, and the song was done. It never changed. i mean it was like how does and then you just you just slap yourself and go what the hell just happened yeah wow that's a great one uh jimmy chamberlain yeah jimmy chamberlain yeah yeah yeah so he ended up founding the company that went public but you had him on to talk about the smashing pumpkin right i mean yeah i don't know exactly how that one happened i think i was reading tech crunch uh and there was a story about jimmy chamberlain once in a while a celebrity gets associated with a technology company it happens you know a lot of times people in music or film yeah because they're curious people and artistic they see business as a potential like ryan reynolds today or you know uh jessica alba or kim kardashian you know a celebrity might see you know technology as a place to go to play or do something interesting in the world and so when i saw that i was like hey you know i reached out to the publicist or someone's like hey is it we're in town you know i'd love to meet them i happen to also you know uh have grown up on smashing pumpkins and have seen them in concert many times and i'm a big fan and so yeah you know what i've always wanted to just do the jason calacana show where i could just interview anybody on any topic yes and all in has let me spread my wings a little bit in that regard where we touch on some subjects outside of business and tech unfortunately it's like politics which is not my passion really art movies and restaurant tours and some of those other things I really am interested in, travel.

34:26But This Week in Star Wars became such a juggernaut and was such a passion of mine. It kind of, I don't want to say sucked the air out of the room, but it took up a lot of my time. And so, yeah, it's just the way it is. I thought the clip was a lot of fun. Now, the next one, we're almost done looking back. We're about to dig into the more recent stuff, but there was a particular episode and there's someone's first appearance that I think might be worth highlighting. So let's run. Instagram, since I moved to at Jason, has been insufferable because people on Instagram are dumb and they just put at Jason, what's up?

34:57And my entire feed is not, so I just can't use it. Are you saying that Twitter users are more intelligent on average? I know I am. Here we go. Look at these kids. Absolutely, there's a standard deviation of at least one and a half. I think it's 10 IQ points. Two of my favorite guests. So Instagram is like the reality TV of social media. Yeah, Facebook's important. But they're beautiful. And children. It's the Miami of the, it's not New York, it's not San Francisco. It's kind of like the Miami of social media. right like that's the perfect metaphor san francisco is like the new york twitter facebook is kind of middle america and that's the miami it's like the beautiful gorgeous no offense to the people of miami you're beautiful and gorgeous but you're also very stupid apparently but that's okay yeah you're also very look at that little boy i think this is going well i love well okay 150 the audience he's got like two serious journalists are like what have i gotten myself into no no work speaking of insane and stupid oh so we work ipo without that clip though was uh i think that's episode 969 and if you listen to the audience it's mollywood myself and jason in the old twist studio and it was i think my first appearance on twist so i'm happy to say that i've been around for at least half of the episodes in terms of my first one to now 2000 do you miss that studio jason yeah i still own it uh and it's literally the suite is for sale right now so if you want the old studio uh it is for sale uh you can go on redfin here it is um it's been staged and cleaned up but that was the office space you're seeing there and then there was a downstairs area um and this is the upstairs we have really tall cellings very beautiful in soma and um it was a giant shell and i was at we were and we were paying like we work had given us a free office when it was just two or three of us but then we needed more because the the venture side of the business was growing we wound up spending six seven and eight thousand dollars a month that we were or more and then i saw this giant loft and you can see this loft is giant it's like over three thousand square feet and this is the downstairs here which has just been set up like as a you know big area but this box that you're seeing here is giant and uh we just set this up uh as you see here as the studio we blacked out all those windows it had a lower ceiling and we were sitting in this corner here where that desk is um and yeah i do miss it because it was a time when people would come to the studio we had makeup and hair we had a you know sir charles as the producer other producers were there producer nick we had a tri cast so we had cameras and it was just fun to be in person and get those vibes now oh yeah sitting here means I could have you from Providence, Rhode Island, or I could be in Austin, and the show just goes on.

37:40It doesn't matter where in the world we are. So there's so many benefits to being able to get guests on this, but it also was like I would have guests on, and they'd be like, hey, we'll go out for lunch after or maybe dinner that night or go see a Warriors game. And I'm going to be recreating these kind of vibes here in Austin. I'm looking to buy an event space here, like a music venue or a theater or a comedy club or something. And in the same way, Joe Rogan has his mothership where they do kill Tony and some of those other shows and comedy shows. I want to have that for podcasting. So I could do an all in episode or this week in startups episode or even the Jason Calacana show.

38:14If I wanted to do just a Jason Calacana show where I interview somebody who doesn't fit into those two buckets. No, I think it's a great. I really do miss in-person events, but I'm also very glad that because I moved away from the tech center, I can still take part. I'd pay a lot of money to go back and just hang out in studio with people and actually see cameras and not look at the same Dell webcam for, you know, two hours straight. All right, but we got to keep moving. So you kind of ruined our flow by bringing up David Sachs and Yammer earlier. You kind of took away some of the surprise. But here is the very first David Sachs appearance.

38:48And then I want to talk about Yammer after this. Look at these kids. My guest today is a really good friend of mine. We've become good friends over the last couple of years. He's a great entrepreneur. He's done three pretty significant companies that I know of. PayPal, you might have heard of it. Did pretty well. Sold to eBay. Then he went on to Genie, which is doing fabulously, which is one of the most sort of advanced genealogy products out there on the market. I would say the most advanced in terms of a technical basis. God, I sound like Trump. Moving on to 3.0. And, of course, he was the winner of TechCrunch 50 this past year with Yammer, which is a business productivity tool, which is just awesome, that we use here at Mahalo.

39:23And welcome to the program, David Sachs. Thanks for having me. Yeah, you're back. Yeah, glad to be your fifth guest. Only four others are more important. Yes, we obviously do that, but we do it in order of importance. Right. And so Peter Thiel and Elon Musk will be the next two guests. Obviously, you're more important than those guys. Right, right. Not that entrepreneurs care. I do appreciate the trailer. So I have to tell you a story about this. That is so funny. He appreciates the trailer. There was no trailer. What I appreciate about David Sachs is it has not changed at all. No, it still rhymes.

39:55Still very right. Yammer. So people who don't know Yammer sold for a billion dollars. It was a big deal. That was a big dollar amount back then. I was working for a tiny little company in Portland, Oregon. I was on a whiteboard and I was like, what if we took Twitter, right? And we put it inside of a company and you could have like status updates and then you could have a feed, but it would only be for your company, but it was super cool. And I was whiteboarding this out. I called it internal Twitter. I knew it was going to be an internal communications tool. And then Yammer gets on stage at the stupid TechCrunch 50 and I was watching live on the stream.

40:24Wah, wah. Wah, wah. And then Yammer won. Womp womp. And then Yammer sold for a billion dollars. Womp womp womp. So I've always hated Yammer because I was clearly way late, dollars short. But it felt like David Sachs had stolen my really good idea. But Jason, you guys have all grown up since then. And so now we have a couple of clips from the besties that were recorded just to celebrate episode 2000. You're kidding me. Oh, no. Really? Yes, sir. Here we go. We've been working on this. All right, let's go. Fantastic. J-Cal. 2 ,000 episodes of twist. What a monumental waste of time. Let's get on you though.

41:05Congrats.

41:12What a monumental waste of time. Do you, do you remember this year? You guys do the, the all in show line. We do a live one. David Sachs is like, thanks for having us to your grift. i mean event i mean event and i was like damn dude that's big you're on stage now that's some pre-stage banter yes yes no we uh we have a long tradition in brooklyn of insulting each other on the porch and when we started playing poker together one of the jokes was just taking the piss out of each other and so one of the charming things i think about all in is that we just take the piss out of each other and don't take each other too seriously uh hopefully and uh have a a good time with it and so yeah that's very nice that's very kind okay all right let's let's get the other two clips going on here oh boy here we go who's gonna take the piss out of me now jay cow oh and it's private jet i'm calling uh from your pj i borrowed it for the day thank you bro for letting me use it and thank you for all you've done in making the all-in pod such an incredible phenomenon it's all you you're an incredible moderator friend entertainer and um honestly i'm just really happy and pleased to know you and really uh wanted to say congrats on your 2000th episode of twist you're amazing bro love you i was waiting for it but i yeah i did lend um i did lend friedberg my jet so that was very nice uh jason you don't have a jet do you oh anyways um but i appreciate about that that that that clip was he like kind of forgot to bring about the twist thing he's like i love you man all in oh yeah an episode 2000 episode 2000 and whatever it is episode 200 of all in episode 2002 what does it matter there's a there's a another bestie out there um mr tamath polyhapatea yeah and he he came from the heart jake al congrats on your 2000th episode of twist what can i say that hasn't already been said um i think you are a tireless advocate and defender and supporter of entrepreneurs and entrepreneurship i couldn't think of frankly anything better to do with one's career i think that you've helped many people who didn't believe in themselves find a way forward to do just that and start something on their own and i think you did that by telling other people's stories investing in them mentoring them it's just an incredible thing i'm really lucky to have you as a friend you have been a part of some of the most important moments of my life many of the funnest moments of my life as well and so i just want to say thank you um and i love you i love you too thank you that made my day um even you know from sax breaking my chops all the way through freeberg and chamath but uh it is true you know one of the things you learn in this life alex over time is um can't make new old friends so you know yeah that's yes and so you know cherish the ones you got and just keep building that legacy with them and then at the end of the days what you have ultimately you know in your life is a collection of memories.

44:11And I think what Chamath pointed out there, like when I could see it in his head, he was like, yeah, you know, congratulations on the work you do. But also those, we've had a lot of fun times together. And so, you know, I just encourage anybody listening, cherish your friends and create more memories with them. We're going to get right back to actual heartfelt stuff in a second, but I just want to take it to a completely different direction. Why the hell isn't All In done around a poker table in which you guys all have to play while you podcast? Because I really think that would put the hammer down and yeah cannot work um i did one episode my friend diego um where we played poker and tried to do an interview the problem is you have to keep stopping to consider what you're doing and bet sizing and if you're actually concentrating then also there's chips making sound and so you know poker is just incredibly long boring periods of folding and predictable with very random exhilarating moments happening every 30 to 90 minutes and so it actually doesn't work but we should do more in-person stuff um and i think we're probably you know i was talking to the boys about doing the election night special again because we did that in 2020 uh even though we didn't get the results that night we're thinking about doing an election night this year and i was like well why don't we just do it in person somewhere and actually we're thinking about doing it around one of our poker tables but yeah you know it's uh having these two podcasts as bookends in my career you know all in is very political and you know big picture and then this week in startups is really focused just on tech and it's very focused for the entrepreneur you know we don't try to make this into you know something it's not it's supposed to be about startups and really inspire people to get in the game and to feature those stories of great startups and the news around them and so tried very hard to keep this what it is right and um i think we've succeeded pretty well i think it's very important because focus breeds um clarity of vision and also it lets you kind of stay true to a single train of thought.

46:05Now, when you talk about inspiration though, the show has had an impact on a lot of people. And one thing we did over the last couple of weeks was we had people send in their favorite moments from the show, thoughts and commentary from the actual audience outs, not just your friends and so forth. We got a bunch. Thank you so much, everybody. We appreciate it. Jason, you're going to love these. Enjoy. I'm Barry Hepton-Stahl. I'm an angel investor and I can say that thanks to you. I think I'm well placed to judge the best or the most important episode of This Week in Startups, because I've listened to or watched every single one.

46:39I just want to say thank you, because you've created something really important. You sometimes say that you've done random acts of journalism, but actually, when you do 2 ,000 episodes of something, then that actually becomes a body of work. I think what you've created is a journalistic masterpiece because you've created a documentary, which is an insider's account of nearly two decades of Silicon Valley startups, innovation, the power law, and all of the other things that we know go alongside that. But turning to my own particular favourite, I have to choose the episode, the first one that you did with Alex Chu from Calm.

47:20I remember exactly where I was when I was watching that. And when you said to Alex you were interested in investing, I thought to myself, oh, I'd like to do that too. I didn't think anything more of it until a few weeks later, I got your email, which said that you were doing the first Angelless Syndicate. And I put some money into that, yum yum. and then I did brilliant with you as well. And then I was discovered on AngelList by a London-based VC firm. And from there, I've now gone on to be a venture partner at two different firms. And I've invested in more than 60 startups. I'm on the board of a bunch of them and it really has changed my life.

47:59So thank you very much to you for that, to your team and all the guests that you've had over all the years. It's been wonderful being alongside for the ride for that. i wish you and your family every happiness now you've moved to texas and please jason keep doing the work oh my god that was so charming i got a little emotional there uh you know when you do these things in a vacuum you don't know the impact you have on people's lives but to hear somebody's life get changed like that obviously is very profound and it's not lost on me that random consistent consistently random consistently random uh acts of journalism or just doing the pod has in fact changed some people's lives and you know it's one of the great joys of my life is traveling through airports and the reason is you know uh there's other grinders in the airport going back to their families or going off to their you know business meetings and trying to raise or get a partner or you know hire that new person and uh they stopped me and they're you know so um kind to me uh to say you don't know this but you don't know this but and then i get the but and the but is i met my spouse at your event i met my co-founder at your event i got to invest in calm at your event i met this person it changed my life right and so i think it is the power of storytelling you know and just telling these stories of entrepreneurs that could actually in the timeline just slightly just steer somebody towards something they didn't think was possible and um i was having dinner with a friend here in austin who wound up running uber la and then i have a friend josh who ran uber new york they became the heads of it because they saw um the travis episode where he was talking about uber and they thought it was like an interesting you know thing and they came in and um yeah uh applied for the job and then told him i saw you on jason's podcast and he was like really people watch that but you know here we are oh my god that was so touching thank you so much also shout out barry for having great like arc to his delivery like he started here well spoken all right very well spoken all right let's hear from sean jackson Jason, congratulations on episode 2000.