This Week in Startups - Episode 2000! Epic guests, huge news, and how to build a media legacy in 14 short years | E2000
Episode Date: August 30, 2024This Week in Startups is brought to you by… Squarespace. Turn your idea into a new website! Go to https://www.squarespace.com/twist for a free trial. When you’re ready to launch, use offer code TW...IST 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 https://www.linkedin.com/thisweekinstartups 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 1 in 3 US startups at https://www.brex.com/twist24 * Todays show: Jason and Alex kick off episode 2000! They reflect on TWiST’s origins and early episodes (1:48), highlighting notable guests and memorable moments (22:31). They also share fan messages, and insights from cohosts (46:05), and wrap up celebrating standout moments (1:04:14). * Timestamps: (0:00) Jason and Alex kick off the show (1:48) The origins and early days of TWiST (9:50) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST (11:03) Recollections of the first TWiST episodes (20:53) LinkedIn Ads - Get a $100 LinkedIn ad credit at https://www.linkedin.com/thisweekinstartups (22:31) Highlighting notable guests and memorable early episodes (30:33) Brex. Get the business account trusted by 1 in 3 US startups at https://www.brex.com/twist24 (32:02) More on standout guests and the TWiST studio evolution (38:37) David Sacks makes his first appearance on TWiST (46:05) Messages from TWiST fans and cohosts (1:05:14) Celebrating standout moments and key highlights on the show (1:28:02) A special message from the Launch team * Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com Check out the TWIST500: https://www.twist500.com * Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp * Mentioned on the show: https://www.youtube.com/watch?v=yZX4fUYo6C0&list=PL24nOpPUQlbZcij2Jo-KNUpWFDSrrQKtH https://www.youtube.com/watch?v=t3bmpMX2qQ4 https://www.youtube.com/watch?v=SP7B0oWTR3o https://www.youtube.com/watch?v=2cdrCYrZIvI https://youtu.be/wM0pVE_b1KU?si=NM1pK-pz9tUQFOqr&t=1366 https://www.youtube.com/watch?v=550X5OZVk7Y https://www.youtube.com/watch?v=6VOQnK7O2To https://www.youtube.com/watch?v=n1_z9oOdytA https://www.youtube.com/watch?v=aM1DDVq3_vs https://www.youtube.com/watch?v=TYA_vdHSD8w https://www.youtube.com/watch?v=qwhP7K3bFRI https://www.youtube.com/watch?v=3seTmyRbcHU https://www.youtube.com/watch?v=ANGHOQ2Cqtc https://www.youtube.com/watch?v=HL2wWE27CUI https://www.youtube.com/watch?v=BXEO3oJKINA https://www.youtube.com/watch?v=43MgbwQBDik https://www.youtube.com/watch?v=SfJtIibCx78 * Follow Alex: X: https://x.com/alex LinkedIn: https://www.linkedin.com/in/alexwilhelm/ * Follow Jason: X: https://twitter.com/Jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis * Thank you to our partners: (9:50) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST (20:53) LinkedIn Ads - Get a $100 LinkedIn ad credit at https://www.linkedin.com/thisweekinstartups (30:33) Brex. Get the business account trusted by 1 in 3 US startups at https://www.brex.com/twist24 * Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland * Check out Jason’s suite of newsletters: https://substack.com/@calacanis * Follow TWiST: Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin Instagram: https://www.instagram.com/thisweekinstartups TikTok: https://www.tiktok.com/@thisweekinstartups Substack: https://twistartups.substack.com * Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916
Transcript
Discussion (0)
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 a number.
This weekend 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, with friends like these.
This 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
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slash twist 24.
All right, everybody, welcome back to this week in startups.
I'm your host, Jason Gallicannis.
And with me, my co-host, Alex Wilhelm, he's Alex on Twitter slash X.
I'm Jason.
At mention us.
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
common theory 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 numbers.
My 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.
2000's 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 six hundred.
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.
Slide focus on stuff that's more recent.
But we're going to start by taking people back to the very beginning.
We have a little bit of a montage put together for you.
So Jason,
sit back.
Oh, 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 Calacanus.
The concept here is pretty simple.
This week in startups.
What does that mean?
Every week, you guys tune in at Ustream.TV or this week in startups.com.
And I have a guest.
Somebody brilliant.
Somebody doing something awesome.
I interview them.
We talk about what they're doing.
We talk about the market.
We talk about the epic battles.
that is being an entrepreneur.
My 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.
I'd like to be here.
First.
First guest.
I'm Jason BK. Calcutta for this weekend startups.
And I'll see everybody at Wolverine tonight.
So, very nicely done.
Wow, that's so touching.
That is an overview of everything.
But we need 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 of this came from.
All right, court, hit it.
Here we go.
Today on this weekend startup, 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 Choi is going to read the news.
Coming up right now on this weekend startups.
Hmm.
Yes.
Yes.
funny how it feeds my people
we ain't gonna live like equals
until we get the money
spend the money and defeat you
yeah money is a move of all
people
yeah funny how it feeds my people
yeah
we ain't gonna live like people
until we get the money
spend the money and defeat you
you can tell it's a little
dating 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 contacted the rapper, and they let us use it.
I had also used some Kanye West's 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, available if you had a pod catching software and an iPod.
before the iPhone existed, this podcast started.
I think it was right before the iPad existed.
The iPod existed.
And so they made that and I had just moved to Los Angeles from in like, yeah, 2012 or, no, sorry, 2003 or four.
I had moved to L.A.
So it's kind of known as a New York guy in L.A.
And then 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 an 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 in books.
there is a huge amount of stuff that 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 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 Allent Summit and so forth.
But here's an early live show.
Okay, here we go.
A live show.
Okay, this is a Kanye.
So you're saying, so we're saying to see me.
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 great.
You'll all get a Tesla delivered to your house.
So you're all set.
People like the Tesla?
Okay, very good.
Beautiful.
And to the people,
people who are in the live chat room, you're going to get a Tesla too.
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?
A baby Matt Mullenweg.
I have no idea.
I literally don't know, but, you know, at that time, 14 years ago, Alex, and you were
in the industry, I think, at that time, right?
In 2012-2011.
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 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. It was an early philosophy of mine. So I always were
back in the Silicon Allie Reporter days, a Silicon Alley Reporter T-shirt in New York,
then I would wear 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, you know, I always have not been coming.
Yeah.
Well, you don't, I don't know if I ever told you this, but I actually went to very early
tech-runch events when you were still doing them with Michael Arrington.
Yes.
So TechRunch 40, Tech-Runch 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 up there kicking off, you know,
the tech one should do.
Isn't that really long, skinny building in San Francisco?
Yeah, it was, 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 tinker, 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, you know, journalist to a millionaire.
And the only reason I bring that up is because it was very rare at that time.
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And to do a $30 million sale, there had been only a handful of those, a flicker to,
Yahoo, the Photoshop site, delicious, the bookmarking site, Weblogs Inc.
And, you know, at that time, Engadgett, Weblogs Inc.
And Gawker were like two of the biggest things.
And then Mike Arrington had obviously started TechCrunch 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.
It was always asking me how I did that.
And I, you know, it was 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 picked 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.
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, uh,
Sequoia, my friend Ruloff had just started there.
So there's always 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 scout program and asked me to be a scout.
It's what triggered at the time David Sachs was doing a website called Jeannie, which was like,
do your family tree.
But then he did Yammer as a Facebook for inside your organization.
And he said, I have to win TechCrunch 40.
And I said, okay.
and my wife, who we were friends socially, and 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, JCal, you're stupid.
I sold this thing for a billion dollars.
You were a key part of it.
You could have angel invests, whatever you didn't.
You should start a fund.
And I started doing the angel investing with Sequoia.
And 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 of experimenting 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 merge these concepts and it obviously served
me very well.
Early on, though, the show did have some of its tenor that it has today.
You were at times, even early on, very acerbic.
And I pulled out one of my favorite little early baby Jason Riffs.
Sorry about that.
I apologize for my acerbic nature in the early days of the show.
Here we go.
This is a message to why combinator companies and hopefuls.
Oh, no.
If you tell Facebook about your startup before you reach critical mass and you get involved with Facebook 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? What was going on?
So the context was Paul Graham had started White Combinator. It was in the early days, probably in the first. This is a single-digit cohorts. But Zuckerberg 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,
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 $5,000 to pitch at these events to supposedly investors. And that was the
origin story of TechCrunch 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 it allowed me to soar and not have his negativity.
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 CrunchBas
and now I'm not working with you here. It's just a feeling following in the aftermath, as it
were. Now, the acerbity point, you being slightly spiky with your language, is not superware.
I 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 won out of the
10 people here in L.A. What's your name?
Yu Kai Chow.
Yes.
Is it Chinese?
Chinese.
From Taiwan.
Oh, from Taiwan?
Yes.
Well, that's not China.
Well, it's Chinese.
Nationality.
Fans on who you ask.
Yeah.
Okay.
That's pretty funny, actually.
That's pretty funny.
Again, that's 14 years before people started talking about the issue.
No, no, I know.
I was watching through old segments and I'm like, I feel like we're having that
conversation now about Taiwan versus China, the natural status.
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 into a cliff. And he had just started SpaceX,
Sacks didn't have craft ventures.
He was doing, like I said,
Yammer and Jeannie.
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 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 Tyler Crowley was my kind of bodyman 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.
He 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, 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
in journal?
What's not?
15?
15?
Give or take?
Yeah.
And so, you know, 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 one 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, but in those early days, I was figuring it all out.
I was trying to be informed, 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 Hartzer,
and he actually lives near me here in Austin,
and he became known as the podfather,
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 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 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.
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Podcasting has gone through, Jason,
several waves of peaks and troughs.
But 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 I go.
Oh, my guys.
Did you feel compelled to start a company
at the age of 18?
18. I mean, I didn't feel like compelled to start a company. It was, 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. The 1500 and over course. Yeah. So that was this on when it was on a 1600 basis. Sure, sure, 800, 800, 800. I love that clip because one,
You changed your desk set up 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 in scons.
And then there's Travis Callanick just sitting there, just off by himself.
But you had props all over the stuff.
What was the prop idea?
Like, what was the prop idea? Like, 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.
So I have a system in which I'd build a.
project, I just imagine it's going to grow 100x. It's going to grow 10x, 10x, 10x, and then 10x again.
And so 10 times 10, 100, 100 times 10, 1,000, 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
you stream 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.
It's free storage because I had no money. 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 were 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 can't tell, you know, it's like, well, what's going on here?
Did you record it on a VHS tape?
And it was like, pretty close to a VHS date.
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 cameras on sticks and cables and takes.
And it was more of 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 the Port with more
hair. All right. Let's see. 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. What do you call it? It's not Patricide. What do you call it when you
kill your grandparents? I don't know. Grandparents is somebody could send that in you.
But I'm serious. Like, you rattle off these incredible list 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 those?
so many deals like that.
So you want to know how I found Twitter?
Please.
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.
I don't have $25,000.
Like, it would be incredibly, incredibly irresponsible for me
to take the little bit of money I had at the time
and put $25,000 in this company.
And what time frame is this?
So this is 2007, I think they actually did that.
Now, I'd worked at Google, but if you know my full biography,
I lost a metric ton of money in the spring of 2000.
Keep a running tab, please.
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?
A trading problem.
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.
Yeah.
That's a whole to dig out of.
You know, he had a lot of gamble in him at that time.
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 Chrisaka ran it up.
And then one time he ran it up so high that we were giving it to charity water.
And then I didn't have a lot of money at a time.
He's like, okay, we owe $3,000 to charity water.
And this guy, Charity Water starts chasing me for $3,000.
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, Tesla.
So now I'm very curious.
Everyone received their Tesla, or was it more like a little car.
Well, no, the funny part about that was I was also very well known because I had the 16th Tesla.
And it was the second one in L.A.
Elon had his.
I had mine.
And that was it.
There were only a hundred of those made originally, 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, who got them.
So I would take people for rides in my roadster.
So I'd park the roadster outside of my office.
And I would tell people it's there.
I'd 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,
I just knocked 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.
He's put a deposit down.
And you know, that's how friendship starts.
You know, somebody really needs help.
It's hard to imagine.
You want needing help.
But at that time, you know, the cars weren't exactly moving.
Yeah.
You know, it was a pretty expensive toy.
Yeah, absolutely.
Help move a couple of cars.
That really fits into the theme that I had when I was watching that Chris Saka clip is that just tech felt smaller back then.
It was like, Chris, like, Ev called Chris.
I was like, oh, you're in for my company.
Click.
And it felt like there was like, I don't know.
And 25.
Okay, nothing, you know.
Nothing.
Yeah.
But it felt 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 he doesn't have that clubby feel to it anymore that made you stand.
No, you know, and it was so clubby that it was almost like 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, you 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, you know, that happened twice a year, you know, it happened like,
you know, 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 to 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
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 built something.
Hey, when founders ask me, what corporate cards do they use? I automatically think of Brex. 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 Brex.
Why do I think about Brex so much? Because knowing everything,
about your money is not negotiable. Nearly 40% of startups that fell, 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 you.
startups, as you know, because you go at the 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, bR-e-X dot com slash T-W-I-S-T-2-4.
I keep hearing stories, people in the 90s that were like, yeah, we raised, you know, a $5 million
series C, and we spent $3 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 come talk to you.
And the next clip, I think, is a good example of just that.
And if you don't know the band, the smashing pumpkins, well, here's the drama.
What is it like?
In the room, take me to that moment when you write one of these things or you're playing it.
Do you know?
It's absolutely like that.
You just know.
You know.
Tonight, tonight, for instance.
Billy woke up in the morning.
Tonight.
He sat down the piano.
He wrote the song.
Tonight.
It was downloaded into his body somehow.
You know, and his whole thing was like, you know, he's simply the messenger.
Like he would just, 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 it?
And then you just, you just slap yourself and go, what the hell just happened?
Yeah.
Wow, that's a great one.
Jimmy Chamberlain, yeah.
Jimmy Chamberlain.
Yeah, yeah, yeah.
So he ended up finding the company that went in public.
But you had him on to talk about The Smashing Pumpkin, right?
I mean, I don't know exactly how that one happened.
I think I was reading Tech Crunch.
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,
Jessica Alba or Kim Kardashian,
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, I was like, hey,
is they were in town?
You know, loved in. Meet him. I happen to also, you know,
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 Calacanis 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 touched on some subjects outside of business and tech.
Unfortunately, it's like politics, which is not my passion.
Really art, movies and restaurateurs and some of those other things I really am interested in,
travel.
But this weekend starvice became such a juggerna on and was such a passion of mine.
It kind of, I don't want to say suck the air out of the room, but it took up a lot of my time.
And so, yeah, which is 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?
And 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.
Here we go.
Look at these kids.
Absolutely.
There's a standard deviation at least one and a half.
I think it's 10 IQ points.
Two of my favorite.
Yes.
So Instagram is like the reality.
of social media.
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?
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 they're 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, look at that little point.
I think this is going well.
I love this.
I love this.
I love this.
serious journalists are like, what have I gotten myself into?
No, no.
Speaking of insane and stupid.
So we work IP out.
That was, uh, I think that's episode 969.
And if you listen to the audience, it's Molly Wood, myself and Jason in the old Twist
studio.
And it was, uh, 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, uh, and it's,
Literally the suite is for sale right now.
So if you want the old studio,
it is for sale.
You can go on Redfin.
Here it is.
It's been staged and cleaned up,
but that was the office space you're seeing there.
And then there was a downstairs area.
And this is the upstairs.
We have really tall sillings,
very beautiful in Soma.
And 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 venture side of the business was growing.
We wound up spending $6,000 and $8,000 a month at we work or more.
And then I saw this giant, and you can see this loft is giant.
It's like over 3,000 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 we just set this up, 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.
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, you know, Sir Charles as the producer, other producers were there, producer Nick.
We had a trycast or we had cameras.
And it was just fun to be in person and get those vibes.
Now, sitting here means I could have you from, you know, Providence, Rhode Island,
or I could be in Austin.
And the show just goes on.
It doesn't matter where in the world we are.
So, you know, there's so many benefits to being able to get guests on this.
But it also was like I would have guests on.
They'd be like, hey, we'd go out for lunch after 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 Killed Tony and some of those other shows and comedy shows.
I want to have that for podcasting.
could do an all-in episode or this week in startup's episode or even the Jason
Calacana show if I wanted to do just a, you know, 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 bar. I 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 fourth.
low by bringing up David Sacks and Yammer earlier. You kind of took away some of the
surprise. But here is the very first David Sachs appearance. And 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 Jeannie, 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
terms of a technical basis.
Not a sound like Trump.
Moving on to 3.0.
And of course, he was the winner
of CheckCrunch 50 this past year
with Yammer, which is a business productivity
tool, which is just awesome
that we use here at Mahalo.
And 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 in that,
but we do it in order of importance.
Right.
And so Peter T.L. and Alon Musk
will be the next two guests.
Obviously, you're more important than those guys.
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 Saches has not changed at all.
No, it seems still 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
and it was going to be an internal communications tool
and then Yammer gets on stage
at the stupid TechRunch 50
and I was watching live on the stream
wom wom wom wom wom
and then Yammer won
and then Yammer sold for a billion dollars
womp 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 Biscis 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.
Congrats.
When I said he hadn't changed
I really
What I mind your mental waste of time
Do you remember
At the liquidity this year
You guys do the all-in show line
We do a live one, you
David Sachs is like
Thanks for having this to your grift
I mean event, I mean event
And I was like
Damn dude that's like you're on stage now
That's some pre-stage banter
Yes, yes
No we have a long tradition
In Brooklyn of insulting each
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, hopefully, and have a
good time with it. So, yeah, that's very nice. It's very kind. Okay. All right. Let's go the other two clips
going on here. Oh, boy, here we go. Who's going to take the piss out of me now?
Jake L. Oh, and it's private chat. I'm calling from your PJ. I've borrowed it for the day.
Thank you, bro, for letting me use it. And thank you.
for all you've done in making me all in pod
such an incredible phenomenon.
It's all you.
You're an incredible moderator, friend, entertainer,
and honestly, I'm just really happy
and pleased to know you
and really wanted to say congrats
on your 2000 episode of Twist.
You're amazing, bro. Love you.
I was waiting for it, but yeah, I did lend
I did lend Friedberg my jet, so that was very nice.
Jason, you don't have a jet.
Do you?
Oh, anyways, but I appreciate it about that, that clip was he, like, kind of forgot to bring about the twist things.
Like, I love you, man.
All in. Oh, yeah, and episode 2000.
No, episode 2000.
Whatever it is.
Episode 200 of All In, episode 2000 twist.
What does it matter?
There's a, there's another bestie out there, Mr. Tumoth, Pollyhappitia.
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?
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. And I love you. I love you too,
Chmach. Thank you. That made my day. Even, you know, from Sacks breaking my shops all the way
through Brieberg and Chamath, but it is true. You know, one of the things you learn in this life,
Alex, over time, is 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. And I think
what Chimov 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 clearly 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 make it.
Yeah, cannot work.
I did one episode of my friend Diego, 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,
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.
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, 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 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 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 I think we've succeeded pretty well.
I think it's very important because focus breeds clarity of vision and also.
it lets you kind of stay true to a single train of thought. Now, 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 out. It's 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-Stall. I'm an angel investor, and I could 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. I 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. I 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 Angelus 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 Angelist 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.
So 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 in 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.
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 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,
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 money or get a partner or, you know, hire that new person.
And they're, you know, so kind to me 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 common 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 I was having dinner with a friend here in Austin who wound up running Uber L.A.
And then I have a friend Josh who ran Uber New York.
They became the heads of it because they saw 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, yeah, applied for the job and then told him, I saw you on Jason's podcast.
And it 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.
Very well spoken.
All right.
Let's hear from Sean Jackson.
Jason, congratulations on episode 2000.
And my favorite episode was episode 1703, which was the first time I heard you invest in companies on the air live right then.
It was such a shock and it was awesome to see those four companies out of Founder University get an investment from you right on the air.
In fact, it inspired us to join Founder University.
and can't thank you enough for making it available to us,
especially the effort of Kelly and Presh,
who did a phenomenal job in running it for Cohort 7.
So congratulations again on your success and for episode 2000.
Oh, it's very kind.
Yeah, we started that Foundry Diversity as a way,
you discover things along the way.
And one of the things I discovered were there were many more people
who were interested in starting a company than had started one.
So I could only really engage one.
say it started one, but nine out of ten people who contact me or stop me in the airport,
you know, whatever, or listen to the program are on their journey and maybe they haven't started
a company yet, or maybe it's four and five. And, you know, for those 80% of people, I didn't have
anything. And I created this founding university, Jackie, and then Kelly and Press ran it. And it's a 12-week
course. And I said, hey, come to this. We'll teach you everything we know. And a lot of the curriculum
there comes from conversations we have on here. And so it's a virtuous cycle. And then
You know, for the other thing we heard was nobody believes in me.
I need my first investor.
And so we created a 25K check that we are very frisky and we give out a lot of them.
And we just have every week you come to Found University, there's a little box.
I would like to apply for $25,000 from the launch fund.
And I think we've done 100 of those 25K checks.
And so for just but $2.5 million, what would normally be somebody's seed round,
we can give 100 people that starting position.
And so when I did the math on it,
and I'm always trying to think of ideas
and most of them are bad,
but sometimes they stick.
There's a very important thing in life
is to keep trying things.
I said, well, if the 25K buys you of 2.5%
in a $10 million startup, right?
Why don't we just offer it to people
at a million dollars as their first investor
and we can get 10 bets for the price of one,
knowing that, hey, if we're betting on them as their first investor,
it's going to be a pretty high fatality rate.
Let's be honest.
And so we'll just make the valuation ridiculously low,
but make the risk incredibly high.
And if people want to opt into it, they can.
And you know what?
60, 70% of people each week check the box.
Yeah.
So it's pretty crazy.
And it's just another example of, you know,
hey, you do something in the world,
you do it consistently.
Maybe you could help some people on the margins,
you know, build their dreams, right?
And so I'm proud of that work.
Hashtag media, hashtag America at the end of that one.
All right.
Last clip from the audience outside.
Let's hear from Matthew Kervis.
Congratulations to J-Kale and the Twist team on episode 2000.
2,000.
Amazing.
So many great moments.
Of the last thousand,
I liked when Cortland Allen came on the show to talk about being an indie hacker and building a sustainable business to support a lifestyle without raising VC.
But my favorite episode is 1328 with Sam Lesson of Slow Ventures because it still highlights the power of the individual but when they can also raise venture capital.
There's some mention of Web3, which is definitely dated, but the power of the individual in a world of AI where we soon see a unicorn that's just a one-person startup.
leveraging AI makes it worthwhile to revisit Sam's approach to investing in individuals.
Once more, congrats to the team, and here's to another 2000.
Yeah.
So that clip makes me very mad because I was on an episode of Twist with Sam Lassen.
And I thought, oh, great, I got a shout-out.
So I went back to see the episode that Arvin was talking about.
And it was not the one that I was on with Sam Larson.
It was a different one.
Brutal.
Brutal.
You know, Sam, actually, I think does his own podcast now with his wife, Jessica,
lesson and Dave Moran from Slow Ventures
and Britt is wife
all great people and it's kind of like a bit of an homage
to All In terms of it being a quartet
but they've kind of taken in their own direction with the fact that it's
two married couples that's very interesting dynamic
Oh man actually I'm going to listen to that now because I can't imagine
it'll be hard not to get a little weird
Yeah same we get snippy perhaps at times
Well but they're all in the industry and they're all
deep in the industry. So it's kind of like a couple's dinner in Marin. It's unique in that regard.
And, you know, it's, again, you have a theme here, which is everybody gets something out of,
you know, these conversations. It's just different things, right? So Sam Lesson might inspire one person.
It might be Travis. It might be Chrisaka. It could be Brian Alvia. Everybody might,
Cortland, I remember that episode from Indie Hacker, really great website where they,
inspire people to just start sustainable small businesses that could become large, but not on the
venture track. And so, you know, absolutely fantastic to see these folks get so much out of it.
And I really appreciate it. It's very touching to me because I am not a big fan of looking back
on these things or, you know, I always put my press clips in a box. So back in the day when you
would get press, it was print by default, right? There was no online press. And so,
So my assistant at the time, Linda Miller, had framed one of the things.
And I took it and I was like, oh, no.
And I found a box and I put it in the box.
And she said, what are you doing?
I got that to put it on the wall.
It's like the first time you've been in print.
I said, do me a favor.
Every time we get press, this is the press box.
It's in the closet.
I want you to put it in there.
I want you to close the box.
Don't show it to me.
She said, what are you not proud of this?
I'm like, I'll give it to my mom.
I'll bring it to her every year or whatever.
She can go look at stuff.
I don't want to think about the press.
It's a review mirror.
I want to look at the dashboard.
I don't want to believe my own press.
I don't want to get diluted into thinking, I'm important.
I want to work and do the work.
And the press is so distracting.
And I had many times in my career where I got too much press.
And it was distracted, you know, whether it was when Elon took over Twitter or with
when Uber had its ascension or Weblogs Inc. got sold.
Or when I was doing Silicon Allie Reporter and on top of the world and on Charlie Rose,
and in the New Yorker. Those kind of moments come and go. The work is what matters. And so that's
why you see that sign behind me that says, do the work. I haven't put it back up here yet,
but it will be. And it's a reminder, not to the audience, a reminder to me that all that matters
is doing the work. Just do the work. Everything works itself out. You can control the process.
You can't control the outcome is another way of saying it. And so where does all this go? I don't
know, but I know that I love doing that work, and the work has meaning to not just myself,
not just to you, but to all the people who watch. And so, you know, I'm more. And I'm really
thankful to all the producers and editors over the years who put these 2,000 episodes
together. So I just want to say thank you to all of them, Brandis Gina, Tyler, Lahn, Sir Charles,
producer Nick. And there were, you know, a dozen other people like, I can remember right now,
obviously, Cort and John right now, who have come and gone and done short sin.
long stints, come back and forth.
But, you know, it does take a lot of work to do this work.
Producer Jackie, of course, Molly, who was here as a co-host for a while, yourself.
Like, it's hard to do this work.
It can be tedious at times.
You have to grind it out.
But, you know, and I'm a bit of a, I don't want to say perfectionist,
but I really do care about quality, you know, as you've seen working with me for a couple of months.
you know, you really need to deliver,
not just for me,
but for the audience, right?
And I think hopefully everybody watching this
who works for me sees the impact it has
and maybe get a little bit of meaning from it
and thanks to the sales team and all the partners over the years.
And you see MailChimp logos in there,
LinkedIn logos in there, you know, Squarespace,
all these people who have supported the show for over a decade,
and then all the incredible salespeople have Luke Lightning,
you know,
and now Matt and Jamie and Hannah.
We've had a ton of other executives help sell the ads.
And the ads keep the lights on,
allow me to hire people like yourself in court and John and Bianca and everybody.
And so it really is a team effort.
I get probably, you know,
99% of the credit for all this.
And I'm probably responsible for only, you know,
60% of it, you know, 50% of it,
I would say.
We didn't show you the docket things.
We wanted to be a surprise because, you know,
yeah, we've been putting this together for a couple of weeks.
But thank you for the perfect segue into a couple of notes we have from Twist co-hosts throughout the years.
And I knew Long is going to be in early, but Lon's coming right back.
So here we hear from Mr. Lon Harris.
There's the man himself.
Hey, Lon Harris here.
And I just wanted to send a brief video message saying congratulations to Jason and the entire team on 2,000 remarkable episodes of this week.
at startups. I remember when we started this show, it was being recorded in Jason's dining room.
It was being recorded in Jason's pool house. It did not have the title this week in startups yet.
We had no idea. We knew we were on to something. We had no idea that it would go on for this many
years, this many amazing guests, this much of a legacy. It's truly impressive to see. I'm very proud
to have been even a small part of it. So congrats to Jason. Congrats to the whole team. And here's
to, at the very least, 2,000 more episodes.
That's a lot of work.
Dude.
Take it easy to.
It's true.
There was a precursor called Calicanus cast we did 40 episodes of, which was just, I would put a microphone on a table and take the raw MP3 and I had Ron Conway on and Evan Williams.
And we don't know where those episodes are.
We can't find it.
Oh, that's terrible.
Yeah, they're a lost too time.
But somebody will find them someday on some website somewhere.
Oh, my gosh.
All right.
Next up we have Mr. Mark's sister who recorded this video in a very pedestrian location, as you'll see.
Oh, wow.
There's my guy.
Hey, Jason, Mark Suster here.
Congratulations on This Week in Startups Episode 2000.
Epic, Episode 2000.
And I have to say, here I am at LAX, Los Angeles, the city that started it all.
I think you started this week in startups here in L.A.
I was one of your earliest guests.
I think I've been on the show five or six times.
I would be on 50 times if you asked.
In fact, you and I launched a separate show together this week in Venture Capital.
I think we should kick that off again.
But you are truly engaging.
That's why people come on your show.
You ask great questions.
You educate the audience.
And being on the show keeps you relevant and in deal flow.
And I just am super proud to see what you become out of doing all of this.
Congratulations.
I still regret not doing Uber with you.
You did invite me to the event where it was sourced.
And you did it.
I didn't.
So I guess I have to jump on an airplane and keep working.
Congrats, Jason, you rock.
Thanks, Mark Schuster.
That's very nice.
You know, he did some guest episodes this summer or, yeah, when I was out a little bit.
And yeah, you always great to have great friends like that.
Yeah, and now next, we only have a couple more.
I promise.
I'm going to get into the recent stuff.
But Sonny, who we all adore.
Oh, Sonny's great.
For his excellent AI stuff.
Let's hear from Mr. Sunny Montre.
Jaycal, wanted to give you and the entire Twist team a huge congrats on 2,000 episodes.
I think very few people understand how much effort
goes into getting these, you know, episodes made,
producing them behind the scenes, the work editing them and publishing them.
So to get to 2000 is a huge milestone.
Congrats.
Really happy.
And here's another 2,000 more.
Cheers.
All right.
Everybody wants me to do 2,000 more.
I guess I'm in for 4,000.
Oh, God.
That's you too.
I know.
If they say you were doing 2,000 more right now, that means I better stretch and sit down
in this chair with some real effort.
We also have David Wise,
from liquidity.
Oh, great.
Awesome.
Yeah, he's done great.
He's been a great, great asset.
Hey, Jason, wanted to congratulate you on reaching 2,000 episodes on this
weekend startups.
What an incredible milestone.
You've had some of the best guests, some of the best panels, and just the longevity
that you've been able to pull off in the space is incredible.
And it's been an honor to work with you and to collaborate together and be a small part
in that journey.
and I wish you much success and much happiness in your podcasting journey.
Oh, nice.
Very nice.
He's also just so well-spoken.
And we got to move on to the more recent stuff.
And Jason,
we have gone through the last thousand episodes and grabbed some big pivotal moments in life.
And you will know exactly what I'm talking about here from I think this March 20th,
2000-20 clip in which we began to enjoy all things total.
No. People who were watching Fox in February and into March were hearing that this was a literal hoax. And it was a continuation of the Ukraine and Russian hoax. And now the same people are going to realize that listening to Fox could lead to grandma or grandpa or somebody with lung disease dying because they went to a party. I mean, it's not like a joke, right?
No, it's not a joke. Well, first of all, one, I'm a failed entrepreneur.
and then a journalist. Let's be super clear about my career path. I think that's pertinent to this show.
People want to know that I've faced playing in public. Alex's back.
Let me know your next idea. I've got to check here for you. No, that'd be a terrible idea.
But on the media diet point, I think we're seeing the limits of the usefulness of having the most popular
cable news channel that has a large echo effect in American media, thinking that the president is always
correct. And we've seen here that they echoed that until the president changed his tune.
and then they rapidly pivoted like a 180 with zero shame.
Back to my point.
I mean, how the hell can they be so hypocritical and not just go home and cry about what they're doing?
And we were talking about people saying COVID wasn't real at the time.
Yes.
And I just want to say if you people are concerned, why my intro to that segment seemed to be so off base from what the segment actually was,
it's because we had two clips from that episode that we were debating between, and I forgot that we chose the other one.
Now, Jason, I brought up props a couple times here because you really liked them.
And a certain CEO once stepped down from their e-commerce company, and you had a very specific way of introducing this.
Let's take a look.
Oh.
Oh, my God.
It's an emergency podcast, Jeff Bezos, the greatest CEO of the past 20 years, is stepping down.
I repeat, Jeff Bezos is stepping down as CEO of Amazon.
That's right, the head of Amazon Web Services.
And Jeff Bezos's longtime right-hand man, Andy Jassie, J-A-S-S-Y, is taking all.
over Amazon.com.
What does it mean for Amazon's future?
What is Bezos going to do with all this time?
And $200 billion or so in equity?
And is Andy the right man for the job?
All that and more when we get back on this emergency pod.
That's funny.
So where did you get the bullhorn?
That's my question.
I think what happened was I was going to be doing a party for my kids.
And I thought it would be funny since we have a big backyard if I took out this prop.
and I started talking to them like I was a police officer or, you know, like a camp counselor.
And boy, that was a hit with the kids.
And then they got their hands on it.
And they all started running around yelling and screaming.
And then, you know, my daughters would take the thing and it has an alarm button on it so you can go boop.
And so, hey, we'd just go sneak up on their poor mom or me.
And for the dogs and blare the alarm.
Oh, man, the dogs would suffer.
Yeah, no, it's not, not cool for the dogs.
But I would, I cat in my office and then this whole thing happened.
And I was like, we got to do an emergency pod.
So I grabbed it and producer Nick and I did an emergency pod by Jeff Bezos stepping down, which did come out of left field.
I mean, I was like, what?
Well, the, the megaphone, though, made it back in the show again.
Let's take a look at the megaphone part two.
Here we go.
Okay.
Everybody likes the megaphone.
It's an emergency podcast.
Robin Hood is going public.
Yes.
That's right. Robin Hood,
Yum Yum for JCal,
has filed its S-1 to go public
and they are allocating
between 20% and 35%
of their IPO shares for you.
That was great.
That was good for me.
What I love about that one is
how happy I am.
Amazon CEO set steps down.
That is a tectonic event.
You broke out the same bullhorn
for a smaller covenant going in public.
So why was that such a big moment
for you in the show?
Well, I had been an angel investor
in Robin Hood,
and it was the second biggest win
you know, of my career at the time after Uber.
I think some other ones, you know, on a dollar basis have been bigger like
Calm or Grin.
But it was still a very big deal.
And so, yeah, I thought I would celebrate it a bit.
Yeah.
Yeah.
We got to bring the cohort back.
Do you still have it?
I still have it.
Yeah, it's in the closet somewhere.
You know, the problem with it is, as you can see from when I put that alarm on,
it's so blaring that it actually hurts my ears.
Yeah.
So I have to like brace for impact when I do it.
There's no way to be.
I thought you were just, I thought that was like,
like you were acting with the whole.
No, no, there is a button on that bullhorn that does the alarm sound.
And then you press it and you get to talk and it amplifies your voice.
So it acts as an alarm system to get everybody's attention and you can speak like you're speaking through a bullhorn.
No, no, I knew that it made the sound.
I just thought you were like, you were playing it up with the moving away from your ear.
I didn't realize it was actually so loud that it heard.
Well, thank you for using it twice then because, one,
It was good entertainment for me.
And also, you deafened yourself now in half your hearing.
So, congratulations to your right ear.
There's been a lot that happened in the last thousand episodes.
One of the things that really struck a tremor throughout Silicon Valley and a lot of people's
portfolios was the decline and fall of FTX.
And when FTX really fell apart, there was yet another emergency pod.
More props here and a couple of familiar faces.
Let's take a look.
All right, everybody.
All heck is broken loose.
Sam Bankman Freed's FTCX Exchange, Molly.
Maybe you could tee up as best you can.
Yep.
What has happened?
We're having an emergency podcast for those of you joining us live.
We haven't been alive in a while.
It's a double red flag situation.
I mean, you know, we're going to dive into this, but I think we can safely say that we
have this is a hinge event in the crypto economy.
Sam Bankman Freed's FTX Exchange is being acquired by its primary competitor,
finance after what appeared to be a run.
triggered by Binance on FTX, primarily related to FTT, if I'm doing this right, the currency
that FTX created.
And then now there's this buyout in process where you have two competitors, like they just
basically fought to the death like Godzilla and King Kong.
Yeah.
That was a monumental moment.
And Molly doing a great job toying it up to our crypto dudes, Vinny and Cindy.
I love that because everyone's clearly going, uh-oh, what's going on?
And how did this happen?
I mean, that one came out of left field.
I mean, there really was no, he, people were talking about FTX as if it was the one well-run
crypto company.
It was the one that was meeting with all the top senators.
The SEC was going to finally have somebody from the Ivy League who they could trust, who would,
and yeah, had that work out.
It was like, I mean, it would be like finding out like Michael Jordan was on steroids.
the whole time or something, you know, or PEDs or Lance Armstrong.
Well, it is like a Lance Armstrong type of fact. Yeah. I mean, you think about how
disappointing, and that's for a minor, minor, you know, a minor sport cycling, all due respect
to cycling. You know, imagine that was, you know, something bigger, yeah.
A sport that people actually watch. Like, what if it was soccer? I mean, it happened in baseball,
right? And people, yeah. Congressional hearings and stuff. Yeah, it was like a big deal. And so it was pretty
monumental deal.
Your earth shattering.
All right.
I'm going to bring up
another breaking news clip
from the last thousand episodes.
This is when Silicon Valley Bank
fell apart.
And Jason,
you recorded a hostage video
for everybody.
Let's take a look.
And today I'm going to talk
a little bit about
Silicon Valley Bank shutting down.
Yes, that's right.
If you're catching up to the story,
this is the fastest moving story
I've seen in the history of Silicon Valley.
And this could be one of the most impactful
stories in the history of Silicon Valley
because so many
successful companies and successful venture firms are being impacted by this shutdown. And I have not seen
this much chaos in Silicon Valley since the 2008 financial crisis and the dot-com crisis. Now,
is it going to be as bad? Maybe, maybe not. I think there's an 80 or 90% chance that Silicon Valley
Bank is rescued this weekend, bought by Goldman Sachs, JP Morgan, somebody, and that everything is
back to normal within a couple of days or weeks.
weeks and everybody's money in the bank is taking care of.
That was such an insane weekend.
Take us back to how worried you were at that moment.
Well, I remember being in a board meeting that Thursday.
And this is a company that had tens of millions of dollars in Silicon Valley Bank.
And I was in the board meeting with Mark Sousker, actually, who we heard from earlier.
And we were debating, do we take our money out?
Because we had heard these rumblings late Wednesday night.
And I said, take half out.
just ship it somewhere else.
I don't care.
Send it to your,
I literally told the founder,
send it to your personal bank of the America account.
So you don't have to open stuff up.
We'll just write some sort of letter with the attorney
that you're not going to scorn with the money
we give you permission to do it.
Sure enough,
in the meeting,
the CFO says,
look, and turns the thing around,
and it says,
can't access website.
And I'm like,
oh my God, Silicon Valley's website is down,
and their website went down on Thursday afternoon
while we're on the board meeting.
And so, you know, that just shows you how even the most in the know people did not see this coming.
There had been some rumblings about interest rates going up and, you know, people may be getting caught or whatever and bank runs.
You know, people had speculated about these kind of things theoretically.
But there were some Peter Thiel Founders Fund groups that I think had kind of seen this happening earlier.
in the week. And he just said, take your money out. Yeah. Because he's Peter Till's Peter
Teal, right? It's a contrary. And so he's just like, take money out immediately. And so once,
you know, 10 companies do it and they tell their friends, I took my money out, a bank run start.
So if you've never seen, it's a wonderful life. You can see how a bank run works. It literally
people run to the bank, and the bank runs out of money. I don't know which run is the reason
they call it a bank run. If people are running from the bank, running to the bank, or the bank
is running out of money.
And let's face it, it's called Silicon Valley Bank.
So people hate Silicon Valley.
They hate rich people.
It was like, well, screw those people.
You know, the problem was, you know, a bunch of like, in Silicon Valley, that's like saying,
I don't know, Kansas City Bank, you know, or Memphis Bank.
It also represents the Bay Area.
So schools, small businesses, everybody uses Silicon Valley Bank.
It would be like using Bank of America in New York City or, you know, whatever, Wells Fargo,
in Boston, I don't know, you know, what's popular in different places.
But if they hadn't, and, you know, for the shareholders of the company, it's the bummer
that the company was mismanaged and went to zero, for people who have deposits there, you know,
it was kind of weird.
And then everybody started creating synthetic tools, like, because there's a 250K FDIC protection,
they started going to startups, like, we'll take, we'll create 10 bank accounts for you.
Yeah.
And put your 2.5 million in 10 different bank accounts.
accounts the most you can't lose anything or we'll put 500k in each the most you can lose is
you know whatever and we'll put it across six different banks and it was like are we really doing
this like we're not talking about all that much money thankfully um they backstop the government the
the you know the the deposits not the equity so all's well that ends well but i did do an all caps
tweet that became kind of famous and uh you know i just did the all caps tweet because i was like
hey folks like there's two other banks uh at the time i had other folks who were taking their money
out of two other regional banks and i said the bank ran at silicon valley bank may be over but the
bank runs on the other ones are just starting and i was watching it that weekend as like on a saturday
people were getting in touch with their bankers at other banks and so yeah it was pretty pretty scary
and i just thought to myself well i guess like half my portfolio of startups are going
to have no money.
So I literally started looking at my own,
I used Silicon Valley Bank for mortgages.
I used them for the mortgage at the studio,
corporate mortgage for that space I bought,
which, you know,
part of the reason I bought it was because,
well, I could because I had low interest loans
from Silicon Valley Bank because they're friendly to me
because, you know, I'm this notable Silicon Valley person.
And that's what they do.
They cater to us.
And I had a pretty low mortgage there.
It was like 5K.
month. And then I was like, okay, what other money can I get together to give loans to
companies and pack it? So I'm looking at my equities and everything. And I'm like,
I'm going to sell some equities or I got to come up with some cash. And I was talking to
different board members. Okay, um, how much can you put in? Maybe I'll give $250,000 to this
startup. You give $250 to this one. We'll make payroll in the next two weeks. I mean,
I was talking about doing this with my personal money, not just the venture fund, because the
venture fund was frozen because all my all my old.
P's are on Silicon Valley Bank.
So the whole system was going,
locking up.
It was pretty scary.
I'm glad that those people missed it because I recall reading the Silicon Valley Bank
investor note when they said that they were going to strengthen their balance sheet,
shake up their investments.
And people weren't talking about unrealized losses on bombs, you know?
And I read that.
I'm like, oh, this seems to be pretty prudent.
You know, here they are.
They're solvent and they're going to make some improvement stinkers.
And then everything blew up.
And I was like, what did I miss?
because to me it seemed relatively conservative,
but I didn't know the madness of crowds and bank runs.
That was a moment for the ages.
We're going to look back on that in 10 years and still talk about it.
So,
Rinks of 3000.
We'll reprise that.
This has been amazing.
We have just a couple more.
Then we're going to wrap up.
I do want to grab a quick moment with Sonny Madra.
His AI with Sunny demos have been fantastic.
So to celebrate the partnership, here is AI demo number 100.
Today, we're going to hit our 100th demo.
So that means we've been through 100 AI companies.
And that's pretty awesome, right?
That also speaks to the pace of innovation happening that in relatively short amount of time,
we've been through 100 demos.
And I think we're going to hit 200 pretty quickly as well.
So it's very exciting.
MultiOn.aI.
The way it works is it's a Chrome extension.
It's pretty invasive because you have to give it full control of your browser,
but it's super powerful.
And so what I'm able to do, book a meeting tomorrow with Jason at 2 p.m.
And what you're going to see it do, it's going to kick off.
And it can read it to you.
And it's good.
It's good.
It's good.
It's pretty crazy.
Holy cow.
For people who are not watching, the Rome extension has taken over the browser.
The inmates have taken over the asylum.
I've given up control of my browser and it's set up the meeting.
Oh, my Lord.
Yes. That was incredible.
Okay, I see where this is going.
Wait, wait, wait, wait, wait.
Something amazing this has happened.
We just saw, if you're watching the video,
we just saw Jason Calacanus interrupt Jason Calacanus,
and that Jason Calacanus interrupt back and cut off Jason Calcanus.
Ladies and gentlemen, the future is the first.
I mean, that was like one of those great moments where you realize,
and this is why talking about these innovations in real time is so powerful,
because I just had this epiphany that like, well, wait a second,
and how much of my life is mitigated through a browser window?
Yes.
A lot.
90% of it?
Yeah, 90%.
So this thing can go empty my bank account, trade stocks, book a meeting, cancel a meeting,
send people emails, block people.
I mean, it could go a muck.
And this is when you're like, oh, right, AI has the potential to be very dangerous and
powerful, we should be careful with this genie we're summoning.
Yes.
Oh, absolutely.
Now, you know, we talked a lot about, you know, old shows, breaking news events.
Sometimes, though, I think you just get together the highest net worth people that you can,
simply so you can commit with your friends.
So here is a couple of brads and one dude named Dara, I think.
Here we go.
Yeah, this is a great episode.
Hey, Dara, how are you?
I'm doing great.
How about you?
Pretty great.
Pretty great.
Looks like I'm stuck on a number.
another pod with two lunatics.
I was asking about this.
This is a real thing now.
It's amazing.
It's an experiment.
It's an experiment.
It's just a couple of guys.
It's a thing.
The Bill, the girl in the era is an experiment.
I love it.
Yeah, an experiment that made some people very upset.
I'll leave it at that.
But yeah, we just did a little experiment because Brad and Bill were always on
a fifth besty kind of role on All In, but they wanted to do more
podcasting. So I said, yeah, I'll help you with your pod and, you know,
it confused the audience a little bit. They were like, what's going on here? And,
you know, they've gone on to do BG2 on their own and all ends continue to
succeed. BG2 is a fantastic podcast. I highly recommend it. But I was able to
host the first two episodes with, you know, those two huge brains,
Brad, working, you know, essentially in public and private markets and
Bill Gurley, the most legendary,
but one of the most legendary venture capitals of all time.
Yeah, absolutely.
Speaking of venture capitalists, though, not everyone has a name that hurts with B.
Some people have a name that starts with S, including Sarah Tavill, who came on episode
1983.
This is very recent, but we loved it.
Yes.
Shout out Sarah.
She's awesome.
Five temptations of a CEO is like an incredible book.
Every CEO should read it.
The thing about wanting to be liked is like an Achilles heel that we all as humans have.
it's a very difficult thing to have a lot of these hard conversations.
And so you have these executives and they are not pulling the company up with them.
They're being pushed up.
When you have too many of those, it's one of those things that even one executive for too long
who's being pushed up with whom we're not having a hard conversation really has these ripple
effects that you always look back and wish that you had made a decision sooner and faster.
brutal he's great i uh you know i'm i'm putting in her into regular rotation i was for a minute i was
thinking about producing a um you know a charlie's angels's version of disweek and startups all in
where i would have a couple of women uh and me do like a round table and i was you know i was my
vision was like molly sarah you know one or two other women and seeing if i could you know uh make that
work.
Yeah.
That's a show on Fox.
That's outnumbered.
Oh, is it really a show?
What a great concept.
Yeah.
I think that I guess, uh, they picked a stupider man though, which I think limited the
appeal of the show.
Now, we're going to close off the historical segments with a guy that it looks like
you found him playing guitar on the street.
Let's go.
So I don't know.
I've made a lot of mistakes too.
So I'm, I'm, I think if you try and fail as many times I can, you will get some
home runs.
Just feel that this year number of times you've had.
Yep, at bat, right?
I think you're probably a little better than Matt, but I do think there's something to that
because you can get high on your own supply.
That's right.
Very quickly.
And it's so random in our industry, what clicks, what doesn't, there is so much luck involved,
you know.
That's right.
I'm not sure what your top investment is, but what is your top investment?
And then how did it go down?
Because I'm sure there's some randomness to it.
Yeah.
If I hadn't seen Travis coming out of a party on the Embarcadero and said, yeah, put me down
for whatever in Uber, it wouldn't have happened, right?
Like, it just happened to be out that night.
The round could have closed.
I mean, there's, my life is filled with these stories.
Like, this is, this is the story of investors.
Like, I feel like there's the stuff that I really, really sought out, which I would say,
like, I would put that in the, like, like, I did a good job at, like, getting this deal done.
Like, I, I went and tracked down Jack.
I had them on my podcast.
I convinced him to be an angel and square.
Like, that was a massive, like, great.
Congratulations. Wow. I love Kevin Rose. I was just texting with him and he had some very complimentary things to say to me and we were just trading some notes and I've just always really admired him. I tried to buy Dig in the early days. He had spent $3,000 building this website Dig and he was up against it and I took him out for sushi in Santa Monica and I said, listen, Dig is sending a lot of traffic to Engadget. I talk to Mark Cuban, we'll buy it from you for a million dollars and make it part of Engadget. I'll give you like $100,000 right now and then $900,000 in payments.
over this time period. He almost took the money. He almost took the million. And then he went and raised
the half million and kept growing. And I don't know how much he would have made in our sale or
together those combined companies would have done better. But, you know, Kevin's just a great
entrepreneur. In some ways, we're very similar entrepreneurs, which is we both had a media side,
angel investing side and building company side. And we both pursued our muse, which is a really
great way to go through life. Now, it may seem a little bit random. And his show with Tim Ferriss called
the random show, but there is something to a life of trying a bunch of things and seeing what
breaks out. And, uh, you know, I really do think Kevin has done a great job of trying a lot
of different things and being fearless. Yeah. And, uh, people remember the wins. Yeah. People don't
remember the losses. They don't. I don't know Kevin personally at all, but I am very familiar
with this old show, Dick Nation. In fact, I think if you go back in time, that might really be the
impetus for why I wanted to do podcasting originally.
And I think so, because I used to watch that show religiously.
Like, every single week it would come out.
I think I watched it on my Zoom, you know, in video.
Like, this is old school shit.
It was pretty amazing, yeah.
Jason, so we're going to wrap up with a shout off from the team here in a second.
But I just, you know, we're episode 2000 now.
Yeah.
Where are you taking the show next, man?
Like, what's coming up?
Great question.
You know, I'm very enthusiastic.
here. I would like us to get to two or three days a week of doing the news. And then, you know,
which we've, we've started to get into a rhythm. We did, we've, we had a week recently with two.
And I really love doing the news with you because you're so well prepared. You have such a
deep end. Just, you know, similar to Molly in that way. And, um, I also want to start doing a live
show every week. So, you know, that's sort of my plan is get a couple of news episodes in. That's the
foundation. We talk about the important episodes here. And then I, you know, I really love what we're
doing, the Twist 500. That's a big initiative.
Oh, yes.
And I think that that, you know, the Twist 500 could wind up being like the Inc. 500 in that or Midas list where you and I and the team could have a real impact on surfacing the most important companies, not just the obvious ones that are private like Stripe or SpaceX.
I mean, they have to be on the list.
But I'm kind of interested in the 250 on the bottom of the list, not the 250 on the top that hit a unicorn status already.
I want to know about the 25 that are on the bottom.
Those are the most interesting to me.
So I think the Twist 500,
some live events and then us getting into like a regular rhythm with the live news.
And I really do like the live aspect when we get people watching.
And, you know, we're just experimented with that.
And yeah, more of the same, more quality.
You know, the quality of the show is very important to me.
Yeah.
Well, I'm in for at least, you know, my first episode is nine, six nine.
Now we're at 2K.
Yeah, do a thousand.
Let's do we load a thousand.
I'm your report.
Well, the team is behind you.
And just to send you out, here's a couple of notes from the people that you pay and therefore have to say nice things about you on camera.
Of course they do, yes.
Two thousand episodes.
Wow.
I came in at, I think, episode 4-54.
I do have a special affection for the episodes where Jason interviews creatives, artists, or authors.
Number two for me would be Jason's conversation with Ed Katman.
the president of Disney and Pixar.
It's an incredible two-parter.
It will blow your mind if you haven't seen it.
It just written Creativity, Inc.
Check it out.
And I think my number one is when Jason interviewed Jimmy Chamberlain,
the drummer of Smashing Pumpkins.
I have never seen Jason this starstruck either before or after.
And I just really cherish that.
Hey, Jason.
We've been friends for 30 years.
We've got a lot of great times at The Garden, watching the next.
My favorite episode of Twist is episode 805 with
Match a line.
My favorite memory has got to be the liquidity summit of this year,
meeting you in person for the first time,
hearing all of your crazy startup stories,
and of course,
meeting with our amazing team.
It's incredible what you've done and accomplished with the podcast.
It's actually the reason how I found out about you.
I started listening to Twist six months into it.
I dropped out of school because I wanted to work for you,
and you gave me that opportunity,
and it completely changed my life.
A memory that has stayed with me about Jason is that,
that the day Uber went public.
He was in the office with us.
Working.
Finding the next company.
The work never stops.
And one of the most horrifying moments I've ever had working with Jason is the day that he walked in the office and we discovered we were wearing the exact same outfit.
I think I burned that hoodie.
I started launch because I was and I still am excited about the world of startups.
There's too many to come out awesome memories with the teen, especially at events that we did.
you know, liquidity, Angel Summit.
And there's a lot of good twist episodes, segments.
My favorite one that really helped me was VC Sunday school
when I was getting started as a researcher.
Hey, chef.
I really appreciate you and the entire Twist team, the launch family.
Every time I think I have a favorite episode, we go and we record another.
And I think that's my favorite, and then we record another.
And I know this comes down to things like amazing AI demos with Sunny,
fantastic news shows and live shows, and really strong, meaningful interviews and
conversations with what I think is important, engage listening with epic guests. And finally,
one of the main ingredients comes down to the world's greatest moderator. My all-time favorite twist
episode is episode 1,403 with Doug Leone from the world's greatest venture capital firm of
all time, Sequoia Capital. In that episode, Doug has two epic quotes that really resonated with me.
The first was hope is not a plan. And he's right. And we've all heard you say that as well.
The second quote was architect your business as you would architect your product.
One of the favorite aspects I have of working here is that I learn something new every day.
Thank you for the ongoing education.
Your insights have always challenged me to think bigger and to push boundaries and to never settle for less.
You always lead with such passion and conviction, which is so inspiring.
Thank you for investing in my growth and always being a constant source of motivation.
and hey, thanks for always having my back and looking out for me on the poker table.
I think I started at launch when you were on episode 1550 and the numbers have just been going
up and up.
Thank you for being so helpful.
Thank you for putting on awesome events like Angel Summit and liquidity.
It's been an honor to help out with those and meet everyone in person.
Your belief that hard work and merit Trump pedigree has not only changed my life, but so many others
out there.
Thank you for being so.
So generous with your time and your knowledge sharing, not only here on Twist, but with our syndicate, at launch, at Founder University, you really are such an incredible example of rising tides, lift all ships.
My favorite memory of Jason has to be during an investment team meeting on my second day of work, where I was just really inspired by the way he led the team with so much energy and confidence.
Hey, Jason, Matt, your sales assassin. We are all super pumped to celebrate episode.
2000 of this weekend startup's with you.
I think I started around episode 800, give or take.
So lots of awesome memories along the way, including a couple launch festivals in Australia.
And a trip to the Great Barrier Reef, a trip to Tokyo with you for tech in Asia.
If I had to pick a favorite episode, I think it's the one with Brian Halligan.
And when he compared Building HubSpot to the Grateful Dead marketing model, what a legend.
My favorite part has definitely been gained to hear your.
vision for Founder Fridays through Twist and then watching it all unfold and now actually
getting to be part of bringing this program to life. It's been awesome. Your dedication to the
startup world has been nothing short of inspiring and I personally owe you a ton from the early
days of watching this weekend startups which made a huge impact on me and being able to jump from
teaching into the startup world and ultimately to work with you to build out Founder University.
Your genuine belief in us as a team, your passion for helping entrepreneurs and the way that you
really pushed all those around you to think bigger, aim higher is something that I truly appreciate.
My favorite memory with you is when I first met you at liquidity and I got to learn about all the
crazy stories from the beginning days of your investing and launch and the early days of the podcast.
It would be an understatement to say that this week in startups didn't bring me to launch.
Over the years, I've been an avid listener of you, Jason, and it's your drive and your passion
for entrepreneurship and inspiring people to take that leap and become entrepreneurs and take those
risks and build something of their own that I find really resonates with being. And so thank you
for everything that you've done on that front. And yeah, I'm loving the team you've put together here
at launch. This week in startups, episode number 2000, let's F and go. What a milestone,
2,000 episodes. Just to put things in perspective, the Sincenz have been on TV for 35 years.
They haven't done 800 episodes. Does anybody even work?
over there. And of course, I remember episode number one, featuring probably the very original
bestie, our good friend Brian Alvey. Well, 13 years later, and here we are. So happy to be part of
this journey, to be part of an amazing team, thrilled to share the ride. Love your brother.
And that's a real big. Yes, yes, chef. Everybody gets into the yes chef.
That's very touching. Thank you. You'll know that I didn't make it.
you won. Because I mean, you're here.
I figured, no, no, no, no, no. There's a reason for this.
They told me to. I was, I was told
that I had to participate. And I just dutched it because
I figured your head's going to be big enough after this
episode. You didn't need one more person telling you that you
that's cool. So, uh, well,
I will say in closing here, you know,
this is very touching, uh, and everybody
get back to work.
Enough. I know when there's, uh, you know,
looking in the review mirror. No, it's, I think it's nice every
thousand episodes to look back. And, um,
you know, very touching for the team.
to hear all that incredible,
all the,
you know,
incredible stories
and how motivated they are.
You know,
startups and innovation
and entrepreneurship
really does drive
the human species forward.
And sometimes,
you know,
it's just simple,
silly little things.
Netflix letting you watch movies
a little more efficiently
than going to Blockbuster
and then making their own movies
and spreading joy
and making people laugh
or helping them get a car
in the rain
or bringing them some food.
or putting satellites into space or maybe meditating.
All of these things are valid pursuits.
And entrepreneurship really does change the world.
And capitalism is a flawed system.
People get a little political about it.
But it's the best system we got.
And it's worked pretty good.
So, you know, start a company, change the world.
And we'll be here to cover your company, your victories, your failure.
Maybe we'll give you some tips on how to maybe help you.
your startup have a better chance of changing the world.
And that's really what it's about.
If you haven't joined a startup or started a company or a project, don't be scared.
Don't be nervous.
You know, everybody's a neophyte.
And then once you start, you know, you'll learn very quickly.
And that's one of the great things.
So don't, if you got that inkling that you want to start a company, just do it.
And we'll be here.
And we're happy to tell your story.
And if we can help you on the margins with some inspiration or some tactical, strategic advice,
you know, the archive's there for you.
And I'm very proud of that archive.
And yeah, don't waste your time watching Netflix.
Watching this week in startups if you're a founder.
All right, bye, everybody.
We'll see you soon.
Bye, everybody.
Thank you.
That was very touching.
And I know you guys put a lot of work into it, so I do appreciate it.
It was gratuitous and awesome.
Let's do it again next week.
Bye, bye.
