What happens when a tech visionary starts his journey in an auto repair shop with no mechanical knowledge? In this captivating episode, Jason Stirman, a multifaceted innovator, shares his unconventional path from running a failing business to making significant strides at Twitter and Medium. We dive into his early challenges, managing unreliable employees, and dealing with dissatisfied customers, revealing how these initial setbacks sharpened his business acumen and conflict resolution skills.

Get ready to hear Stirman's nostalgic trip back to the early days of Twitter, packed with memorable anecdotes, including Snoop Dogg’s visit to the office. This episode explores not just the evolution of a social media giant, but the cultural impact it’s had ever since.

We delve into Stirman's friendship with Ev Williams, uncovering how their collaboration at Twitter and Medium, shaped the digital landscape. Discover the passion behind their efforts to create platforms that balance media consumption, foster thoughtful writing, and champion the exchange of ideas. Tune in for an episode filled with personal stories, insightful reflections, and the raw truth about combining vulnerability, creativity, and cultural branding.

"Unglossy: Decoding Brand in Culture," is produced and distributed by Merrick Creative and hosted by Merrick Chief Creative Officer, Tom Frank, hip hop artist and founder of Pendulum Ink, Mickey Factz, and music industry veteran, Jeffrey Sledge. Tune in to hear this thought-provoking discussion on Apple Podcasts, Spotify, YouTube, or wherever you catch your podcasts. Follow us on Instagram @UnglossyPod to join the conversation and support the show at https://unglossypod.buzzsprout.com/.

Send us a text

Support the show

Mark as Played
Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 2 (00:00):
This week on Unglossy 140 characters and a button.
I could build this in a weekend.
This ain't going to be nothing.
It's fun now, but I'm not goingto move my family across the
country for this thing.
And Evan just looked me rightin the eyes and he said look, if
we do this right, it'll changethe way the world communicates.
I'll never forget that Set in ashady bar in the mission and at
the time I thought like I likeyou, but you're crazy man, you

(00:23):
know.
But I want to rock with you.
So I stuck with him.
We started working on.

Speaker 1 (00:29):
Twitter and some other ideas From the top.
Yeah.

Speaker 3 (00:33):
I'm Tom Frank, I'm Mickey Fax.

Speaker 4 (00:35):
And I'm Jeffrey Sledge.

Speaker 1 (00:37):
Welcome to Unglossy, to coning brand and culture.
I'm Tom Frank, partner andchief creative officer at Merit
Creative.
This is Mickey Fax, hip-hopartist and founder and CEO of
Pendulum Inc.
And that is Jeffrey Sledge, aseasoned music industry veteran
who has worked with some of thebiggest artists in the business.
We're here to explore themoments of vulnerability,
pivotal decisions and creativesparks that fuel the

(00:58):
relationship between brand andculture.
Get ready for athought-provoking journey into
the heart and soul of brandingthe unscripted, unfiltered and
truly unglossy truth.
All right, guys, we got a goodone, a really, really good one,
and it went places that I didn'teven anticipate.

Speaker 3 (01:16):
This is true, this is going to be good.
This is my friend.

Speaker 1 (01:20):
This is your friend, so you finally contributed.
Yeah, you know, wait a minute,though he might is your friend,
so you finally contributed.

Speaker 3 (01:26):
Yeah, you know, wait a minute, though he might be
your friend, but who did theoutreach?
You did the outreach becauseyou know that's your job.

Speaker 1 (01:31):
But you know, but that's my guy like I met him
before you, you did, you didmeet him before I didn't know
anything about him.

Speaker 4 (01:36):
So it was really interesting to me because I was
learning I I don't even know.
I was like who's?
I called me because who's thiscat I don't even know?
Yeah, he actually did try to'sI called me I was like who's
this cat?
I don't even know.
Yeah, he actually did call me.
I tried to look him up online.
I couldn't find much.
I was like I don't know.

Speaker 1 (01:47):
Who's this ghost in the wind?
This is an underground guy.

Speaker 3 (01:50):
Sturman, sturman, which just the name itself
Sturman.

Speaker 4 (01:59):
That's just it.
It's like Prince Sturman.
Yeah, you know St the developerof Twitter.

Speaker 1 (02:03):
I actually had no idea.
I knew him because of the Barsapp Yep and I knew he worked at
Meta Yep.
I had no idea the backstoryabout Twitter, about Medium,
about all his other interestingapps Yep and the fact that the
guy used to own his own car Autoshop, auto shop- Mechanics shop

(02:24):
?

Speaker 4 (02:24):
Yep, he doesn't know anything about cars?
Yep, he doesn't know anythingabout cars.

Speaker 3 (02:26):
He doesn't know anything about cars and he's
also a producer, you know, uh,he didn't reach out to me to get
on his project yeah, he didreach out to me.

Speaker 1 (02:34):
I didn't bring that up, but uh, we'll talk about
that later.
Yeah, but uh, he has.
He has a new music out thereright now.
Yes, he does.
You gotta go check it out, lookfor sterman yep, it's good
stuff.
It's good stuff.
It's different.
It's not what I expected.

Speaker 3 (02:45):
It's not what I expected either, but it sounds
really good and he's verypassionate about what he does.
Just a talented, intelligent,individual man.
He's such a peaceful soul aswell yeah, very peaceful, very
in tune with nature and justlife and the spiritual side of
things.
I think people are going toreally enjoy this conversation.
Well, I think they are too.

Speaker 1 (03:05):
Yeah, and with that let's get into our conversation
with.

Speaker 4 (03:09):
Sturman, sturman.

Speaker 1 (03:11):
Sturman Unglossy is brought to you by Merit Creative
, looking to skyrocket yourbusiness's visibility and drive
growth.
At Merit Creative, we solveyour brand and marketing woes
With big ideas, decades ofexperience and innovative
solutions.
We'll draw in your targetaudience and keep them hooked.
Remember, creativity is key tosuccess.
Partner with Merit Creative andunlock your brand's potential.

(03:33):
Learn more at MeritCreativecom.
And now back to the show.
I'd like to kick things off byreading something written by our
guest that I found verycompelling and I very much
enjoyed.
Hopefully you'll like this.
Let's see.
So a dude walks into a bar,sits down and says to the

(03:53):
bartender my name is Sturman.
I build things on the internet.
I'm currently working on newproducts at Meta.
Previously I helped startMedium and was early at Twitter.
I design, code and lead productteams.
I received a computer sciencedegree from the University of
Texas.
I helped create him, her andhim.
I'm thinking that's the kidsI'm married to her.

(04:14):
I believe that's his wife.
I like to make art.
I was voted most creative by ahigh school senior class of over
800 students.
I once scored 27 points in aseventh grade YMCA basketball
game.
My favorite color is a subtleshade of invisible.
My spirit animal is the early90s Dennis Rodman.
I'm standing right behind you.
Well, actually, at least fortoday right here on my screen,

(04:35):
people say hello to Sterman,thank, you for joining us.

Speaker 2 (04:43):
Yo, man, good to be here.

Speaker 1 (04:43):
That's the whole long-winded intro man, but hey
you wrote it and I stumbled uponit and I was like this is
perfect, this is perfect for you.

Speaker 2 (04:52):
Well, I wrote that a long time ago and now I feel
like I got to go update it.
At least, behind the him, herand her, there's some photos of
my family which I haven't beenupdating in a very long time.

Speaker 1 (05:00):
Okay, that's my background, so let me ask you
this?

Speaker 2 (05:07):
Does anyone call you by your first name at all?
Nobody, nobody.

Speaker 1 (05:08):
Actually my parents.
My parents are the only ones.

Speaker 2 (05:11):
My sister, because they're all Sturmans also.
But man, I just grew up withlots of different Jasons grew up
in Texas and I must have had inmy classes growing up my grades
were probably five, 600,000people and so that was a popular
name back then.
I think there was literallyseven or eight other Jasons, and
so I've been rocking Sturmansince a wee little boy and still
going strong with it.

Speaker 1 (05:30):
I like it.
Now, mickey, before we get intohow we know this gentleman, I
did find this.
I do a lot of research, man,and I want to show this.
I found this picture of you.
I didn't even think this.
I thought maybe I had the wrongguy.
Like, who is this guy?

Speaker 3 (05:44):
Move it over a little bit, let me see.
Can you see that?
Wow, look at that guy.

Speaker 1 (05:48):
That doesn't even look like the same guy that
we're talking to right nowHandsome, hairless individual.

Speaker 4 (05:53):
Yeah.
He had a triple zero on thehead, See I mean, I think it
fits in a little bit more withus, but you know, zero blade on
his joint yeah, man used to usedto rock it clean, clean cup.

Speaker 2 (06:06):
But I think the older I got then you know less I
cared about what people thought.
I always wanted to rock longhair.
So I've been this is like beengoing since covid.

Speaker 4 (06:13):
Basically this is a you know three or four years
okay, so I'm just I'm gonna rockman what year was the perfect
public was the perfect, perfect.
Uh, time to start that?
Because you know barbershops isclosed.

Speaker 1 (06:24):
Everybody was wolfing anyway, that's right it was the
perfect time to just change ingeneral, right, it was the
perfect time to do somethingdifferent, to just be you and do
something totally crazy andwild.
I kind of I kind of miss it alittle bit, not all the disease
and all that, but the time I wasthinking about that shit the
other day too.

Speaker 4 (06:44):
I'm in Atlanta now, sturman.
I don't know if you know thatyou wouldn't know that, but I'm
from New York.
I was dead in New York City, inManhattan, when COVID started,
and I missed that shit.
You missed COVID, I missed thetime of the things that were
around COVID, not COVID.

Speaker 3 (07:03):
The time, the time.

Speaker 4 (07:04):
Being able, the time of the things that were around
the time, the time, the time.
Being able to literally walkdown the middle of Broadway
because there was no cars on thestreet, walk down Broadway like
it's a sidewalk.
I miss that type of shit andthe peacefulness of it.
I totally get it, man.

Speaker 2 (07:21):
I don't miss the sickness.
Obviously I was very lucky andprivileged to be in this
situation.
Me and my family could be happyand healthy.
But for me I'm kind of anatural introvert, so it was
like a time when everything shutdown.
The family kind of got together.
We relied on each other, reliedon our neighbors, and that's
when I really started gettingserious about music production
we can talk about here in alittle bit but also everyone's
picking up new hobbies andyou're on Zoom calls with people

(07:41):
at work.
You're seeing their kids andspouses in the background, kind
of realizing like everyone'sjust a human trying to do their
best.
You know.
So, like you know, I don't,like I said, don't don't miss a
sickness.
But I look back at that timepretty fine.
I think it's pretty special.
Like you know, a couple ofyears indoors with the fam was
was good for me.

Speaker 1 (07:56):
Yeah.
And I felt like I met morepeople I met more I would have
never met ever before, includingyou, right.
So, mickey, we got to tell him,we got to tell the world how we
know this guy.

Speaker 3 (08:07):
Well how I know him.
You met him.
I met him through you, mickey.
I'll admit that.

Speaker 4 (08:11):
Mick is the plug.
Mick is the plug and he neverlets you forget that no, he
never lets me forget it.

Speaker 3 (08:16):
We can't let anybody forget it.
I mean, I was bored, you know,I was bored in the house and I
brought some rappers up, youknow, and the rappers came on
and they started rhyming and hebrought me up and I just spit
straight fire and he was like Igot to rock with this guy.

Speaker 2 (08:38):
Is that what happened ?

Speaker 3 (08:39):
The end, let's cut the show, that's not what
happened Go ahead.
I think I brought a couplecelebrities up and our mutual
friend DJ Deluxe.
He was like hey man, you knowwe could do this through the
Bars app and you know we canhelp fund it and get it going.

(09:00):
And no exaggeration, I brushedDJ off the first time.
I was like hey man, I got thisman Chillation.
I brushed DJ off the first time.

Speaker 4 (09:05):
I was like hey man, I got this man.

Speaker 3 (09:07):
I'm doing this myself .
I don't really need any help.
Right, that was the firstmessage I sent to DJ, and then
DJ is very, a very persistentperson.
The second time he came back.
Hey listen, bro, uh, nah,seriously, like, we'll take care
of some of the payment andstuff like that, don't worry
about anything.
You know, you have the traction, you can get people here to our

(09:30):
app and let's make it work.
And I said I don't believe you,but OK, let's, let's, let's do
it.
And DJ walked me through thisprocess and eventually, you know
, in the second season is when Ikind of met Sturman.
The first season was a completesuccess.
We had Lupe pull up and youknow Vega, the 7 Ronin, who won

(09:54):
our competition.
He's now like a household namein the underground scene.
He's selling vinyls out in fiveminutes, you know.
And before we put him on thebars app, he had no exaggeration
, he had like a hundredfollowers.
He's up at like seven, eightthousand followers now and
that's strictly off of what wedid with the bars app and, uh,

(10:17):
you know that whole competition.
Um, so when we pulled it backfor the second year you know,
obviously, time, I brought timein for the first year and then
we came back around for thesecond year and that's when I
got a chance to kind of get achance to know who Sturman was,
what he accomplished in his lifefrom a tech perspective and how
he was involved with the Barsapp.
Does that sound right, sterling?

Speaker 2 (10:38):
That sounds exactly right, man.
And, like I said, I know it wasseason two of the Mickey Facts
Bars Out Challenge.
We really connected, but I wasfollowing the story from day one
.
Big shout out to D-Lux DJ forhooking us up and for being
persistent and riding you tillyou'd rock with us and, man,
that was a huge moment for me,that was a huge moment for the
Bars app.
Hopefully it was good for youand and end of the day, we put

(11:00):
guys like vega and I, lord owenand these other guys you know on
the map, gave him a platformand that's.
That's pretty rad.
And those, those, those flowersare still blooming from we did
a few years ago, which isabsolutely and mickey, I don't
think you're.

Speaker 1 (11:11):
You're giving it its full love here to me it was like
the american idol of rap musicand it all.
It all happened on Instagram,we released, we released it out
on YouTube afterwards.
But I mean it was unbelievable,like we would get what 10 to
maybe 16 guys pull up everynight.
They would, they would, theywould drop their bars.

(11:32):
I mean it was, it was awesome.
I mean it was awesome just tolisten to these guys who would
just walk up to a mic and startspitting, and it was.
I loved it.
I enjoyed every minute of it.
Thank you for getting involvedwith us, and I think it was a
very great mutual relationshipand I thoroughly enjoyed being a
part of that Me too, yeah.

Speaker 2 (11:54):
All right.

Speaker 1 (11:54):
So let's rewind a little bit.
We're going to get back to theBars app, because we do have to
ask some questions about it.
Let's rewind a little bit.
You're originally from Texas.
Yes, sir, you went to theUniversity of Texas Hookah Horns
, and then did I read right?
You owned an auto repair store.

Speaker 2 (12:13):
I did.
I did.
So let me I'll back you up alittle bit.
So graduated from UT in 2000with a computer science degree.
I was always a big tech nerd butI was also a big hooper, always
playing music.
But like I was like a closettech nerd when I wasn't cool to
be a tech nerd.
And so I went to school, got acomputer science degree,
graduated and started working asan engineer in Houston but

(12:34):
really realized like being asoftware engineer was just not
going to cut it for me.
Like it's just, you know,writing code was one way for me
to express my ideas, but so wasdrawing portraits and making art
and making music and buildingwith Legos, and so it was just
like another tool to share myideas with the world.
So I kind of got burned out asan engineer pretty quick.
So drop that and just wasfeeling really entrepreneurial.
My dad was a lawyer but hestarted his own law firm.

(12:56):
I think he just instilled withme a lot of that kind of like
entrepreneurial energy.
And you know, working forsomeone has always been hard for
me because I like really valueautonomy, I like to move and
shake at my own pace and do myown things, and so, after
dropping the engineering job, Iwas kind of looking for
something to do, and long storyshort, but this auto repair shop
in my in my neighborhood waskind of shutting down.

(13:17):
The owner had already moved outof state but then the deal that
he was going to sell it.
But the deal fell through, sohe was left in a weird situation
and so I heard about it and soI jumped in.
I can, to this day, couldbarely open the hood of my own
car.

Speaker 1 (13:30):
I kid you not.

Speaker 2 (13:30):
See, I thought you were going to say the opposite.
No, I kid you not.
I couldn't change oil, nothing.
I'm looking at engine.
I don't know what any of thatstuff is, I don't know how it
works, but I saw an opportunityto like own a small business.
I thought like I could marketthis thing and get some people
in here and, um, long storyshort, it was the worst year of
my life.
I'm not kidding.

Speaker 4 (13:50):
Like oh wow, I thought it was going to be like
oh, this shit was fly.

Speaker 2 (13:55):
No, the exact opposite.
I had.
I had two mechanics who werealcoholics and stealing from me
the entire year, which I foundout later the previous owner had
really done some people wrongand so you know people are
already going into like autoshops kind of with their guard
up, feeling like they're goingto get taken over.
And so here I am.
I'm there at 5 am cleaning thetoilets, you know, getting ready
to open the shop.
I'm running the desk I couldn'tafford to like hire anyone, so

(14:17):
it to me and these twoalcoholics running this place
and they people would come inbecause there's something got a
broke and they're screaming atme and coincidentally I look
like the previous owner, whichdidn't help me and so I had.
I had one dude literally jumpover the counter to fight me,
you know, because somethingbroke on his car and like the,
it's all like a differentlanguage.
I didn't even know what peoplewere talking about.

(14:37):
So you talk about a crashcourse into entrepreneurial
efforts, business ownership,conflict management.
That stuff I learned in thatyear.
Like I said, it was miserable.
That's probably the closestI've ever been to depression in
my life.
But what I learned that yearcould have never been taught to
me in a classroom in a textbookfrom friends.
You just got to go through thefire to learn sometimes.

(14:58):
So very appreciative for shoutout Integrity Automotive in
Magnolia, texas.
But man, as soon as I could getout of that deal, I got out.

Speaker 3 (15:06):
Wow, wow.

Speaker 4 (15:08):
That's definitely not the way I thought that story
was going to go.

Speaker 1 (15:10):
I didn't think it was going that way either.
So wait a minute.
So you jump out of that.
Did you immediately jump overto Twitter?
Is that was the next landingstop or no?

Speaker 2 (15:25):
No.
So while I was running the shopI was still like dorking around
with code and design and I hadgrown a little design studio
before that Cause I was, likeyou know, teaching myself color
theory and layout and typography.
And then you know the early twothousands like I had.
This somewhat embarrassinglylate realization for me is that
like I could design, I couldcode, I could make my own like
web apps, and the web apps werea new thing come like 2003,
2004,.
You know dynamic and this wholeboom of the industry.
And so I started dorking aroundwith little ideas, you know,

(15:48):
just for me, little fun ideasfor me and my wife, my family.
And a couple of the ideasreally took hold and before I
know it, like I was on the TodayShow, I was in Time Magazine
twice, I was in Wall StreetJournal.
These little apps this littlecomputer nerd from Texas was
building.
I was really fascinated withSMS technology in the early
2000s.
The texting it was new, y'allremember like T9, where you had
to like press the buttonsmultiple times.

(16:08):
We're all probably aboutsimilar age.
And back then it cost per textor it cost to text outside your
network, but I just sensed thiswas going is going to be a big
thing.
So I started working on cleverways to send text messages and I
came across a little likesecret that no one knew about
how tech, how telephonecompanies, worked.
And I was enabling people to goto a website, type in like a

(16:30):
date and time, a message and acell phone number and it would
send that message to that numberat that date and time, which I
just thought it would be coolfor, like me, to remember to
tell people happy birthday orhappy anniversary or whatever.
But I didn't realize like I wasone of the first people to kind
of build a interface to SMStechnology that wasn't, wasn't
on the phone, I mean, thesethings didn't even exist yet,
wow.

(16:51):
And so it really blew up fasterand quicker than I could have
imagined.
And here I found myself justwith a lot of national attention
.
All the tech nerds of SiliconValley were calling me because
they were wanting to utilize mytechnology.
And that's when I had a momentlike oh shit, people like what I
can do, I can maybe dosomething special with this.
So I created a few littlecompanies around that, really
selling API access to send textmessages easily.

(17:13):
But while I was hitting uprestaurants and dentist's office
and I still had a very localmindset.
Growing up in Houston area.
Around Houston.
Some nerds out in Silicon Valleywere working on this idea that
became Twitter.
But it wasn't Twitter to startit.
They were at a previous company.
It was a podcasting companycalled Odeo and they kind of put
podcasting on the map.

(17:33):
But then they caught wind thatApple was probably going to
build podcasts into the nextversions of iTunes.
They were right, kind of killedtheir business.
They couldn't compete withApple at the time.
So they were spinning around onsome different ideas and Twitter
was the idea that kind ofcaught hold.
And so, right, when I met theseguys, I had this Twitter idea
and they were like, we know thestuff you're working on.
I had heard of them because thefounder of Twitter named Evan

(17:54):
Williams.
He had sold Blogger to Google.
It was Google's firstacquisition, so all that blog
spot stuff back in the day.
That was him.
So I kind of I was like a, Iwas like a you know Silicon
Valley fan boy, like I kind ofheard of him, and they were like
, look, we've got this ideaTwitter.
And I was like I flew out thereand meet with them Cause, yeah,
I can help y'all with this SMStech, because Twitter was all
text message in text message outto start.

(18:15):
And they were paying out thewazoo for their text message
bills.
I was like I know how I can dothat.
I can help you out here.
So we started rocking togetherand pretty early on, me and one
of the founders he kind ofrealized, like I just had, I
like to wear a lot of differenthats.
I could design, I could code, Ican make products for people, I
like to talk to people.
So we started working ondifferent ideas and we had this

(18:38):
company called ObviousCorporation and Twitter was
going to be one of the ObviousCorporation products.
So while I helped them with theSMS stack, twitter kind of
started taking off and we wereworking on some other ideas.
But within about a year it wasreal clear that, like, twitter
was the idea.
You know, when it started itwas kind of the punchline in
Silicon Valley.
People were like who cares whatyou have for breakfast?
You know, like it was like, whywould anyone want to do this?

(19:00):
Little did they know.
Well, people were.
People started making fun ofTwitter on Twitter.
That's when we really knew wewere onto something.
But you know, to my discredit,when it came time to really make
a move out there, evan, my guysaid hey, bring your family out
here.
It's going to be a whole thing.
And I was like 140 charactersand a button, like I could build
this in a weekend.

(19:20):
Like this ain't going to benothing.
Like it's fun now, but, likeyou know, I'm not going to move
my family across the country forthis thing.
And Evan just looked me rightin the eyes and he said look, if
we do this right, it'll changethe way the world communicates.
I'll never forget that set in ashady bar in the mission and at
the time I thought, like I likeyou, but you're crazy, man, but
I want to rock with you.
So I stuck with them.

(19:40):
We started working on Twitterand some other ideas Did you
move out?
to the Valley, Not right away.
I said I'll rock with you, butI want to do it from.

Speaker 3 (19:48):
Texas.

Speaker 2 (19:50):
A little side note is right before that I had started
a company and raised some moneyfrom some venture capitalists
out in Silicon Valley and I hadactually sold my house in Texas.
I had moved to California andmy family was packing up the
house to meet me out there andwhile that was happening the
whole deal fell through and Ihad to move back to Texas.
So this was right on the heelsof a very disruptive almost

(20:10):
moved to California, moved backto Texas situation.
So when Evan approached me, Iwas like I can't do this to my
family again.
My wife was pregnant at thetime you know kid and so I
didn't move then but stuck withEv, started rocking with Twitter
, really started learning tomanage people, lead product
teams, and it was really clearthat his vision for changing how
the world will communicate wasfeasible.

(20:31):
You know which really surprisedme.
But it was also a unique momentin time where, like you know,
the world had never seenanything like that.
When we started it, we werejust hoping that the tech blogs
would stop making fun of us.
Never did we think, like youknow, world leaders would use
this to organize rebellions andterror.
I mean, like it really didchange the way the world
communicated, and you know I'mreally happy to be a part of it.
So I did move out about a yearlater and then that was 2008 or

(20:56):
so, but out ever since.

Speaker 1 (20:58):
That's crazy that Evan Williams I mean he saw it
right from the.

Speaker 2 (21:06):
I mean, I guess you have to.
He was the visionary part ofthis.
Yeah, I mean it's.
It's a well documented storynow.
But one of his engineers atOdeo was Jack Dorsey, who now is
a pretty name, and it wasactually Jack's original concept
.
But but Ev had the leadershipchops and the money and the and
the and the bravado to take itand really make it something.
And so you know, if you readthat Twitter story, like between
Biz Stone, jack Dorsey, evanWilliams, like the kind of

(21:27):
rotating cast of characters andleadership and a lot of discord
at the board level nonstop.
But to me Ev always representedkind of the heart and spirit of
what Medium could and should be.
And credit to him, man, he didit Wow.

Speaker 1 (21:40):
Looking back at that, now that we know where Twitter
is today, obviously they'vechanged the world, but now we're
on the other side of it.
Yeah, what are your thoughts onTwitter today?

Speaker 2 (21:51):
Man, my overarching thought.
I just have a lot of gratitudefor what that product I mean.
It really put me on the map inSilicon Valley as someone that
could work and flourish in thisindustry.
It really did change the waythe world communicates.
I have a lot of lifelongfriends that I met on Twitter,
that worked at Twitter and so,like my heart's really full and
I feel like you know, I feelcomplete from what Twitter
provided for me.

(22:12):
That said, you know, twitterhasn't changed a ton in the last
15 years or so.
I mean still short form tech,put, put it out there.
You got followers and I alwaysfelt like, as fast as it grew
and as popular as it is, that itstill had untapped potential,
you know, and it still had a lotof problems and it didn't
really evolve as quick as someof these other you know,

(22:33):
snapchats and TikToks and thingsthat came up.
I mean, look, twitter had Vine,vine was TikTok before TikTok,
but they squandered it.
So there was a lot of storieslike that that.
I feel like Twitter could havecontinued to grow and really
cemented itself in the fabric ofour society even more so now
Elon at the helm, I think I'mjust more than anything sad
about it.
I mean, whether you like Elonor not, I have a Tesla.

(22:55):
I've met Elon a couple of times.
Maybe there's, obviouslythere's a genius in there
somewhere that you know cancreate these things.
He's also happy to give you thefinger and tell you to fuck off
and do it.
Do it his way.
And when he acquired Twitter,he did that with a lot of
employees.
A lot of them were my friendsyou know, which still haven't,
you know, got what's owed tothem, to them, you know, after

(23:17):
this, this whole deal, and youknow it seems like Twitter is
kind of becoming like the Elonfan club social media site.
You know it's almost like, youknow, trump has true social
Elon's got Twitter or X now.
And that said, though, it'sstill going strong, like I think
it's a testament to howingrained Twitter is into the

(23:39):
communication infrastructure ofour planet.
Trained Twitter is into thecommunication infrastructure of
our planet Because even with youknow someone who's you know a
hothead kind of crazy runningthe thing and you know giving
the finger to advertisers andemployees and you know kind of
doing everything to mess it up,it's still going.
And I'll say, zooming out alittle bit, twitter has always
tripped over itself withinternal discord and leadership
changes and bad calls and thingslike that, but it just keeps on

(24:02):
going, which I think is atestament to the original seed
of that idea.

Speaker 1 (24:05):
Original seed yeah.

Speaker 2 (24:06):
Really special and continues to flourish.

Speaker 3 (24:09):
So I was on Twitter 2007.
Somebody that, a guest thatwe're going to have on here at
some point, saint.
He told me he was like you needto sign up for this new thing
called Twitter, and I was likeokay, so I signed up for it and

(24:31):
you know, I would go on thereand just speak my mind like most
people did, because then nobodyknew it was going to turn into
what it turned into at Twitteron September 25th 2009, which to
me is probably aside from apresident being elected or the

(24:52):
insurrection is probably one ofthe biggest days on Twitter the
day that Michael Jackson passedaway.
Michael Jackson trended For 10days straight.
Were you at Twitter at that?

Speaker 2 (25:11):
time.
I was.
Yeah, I was full-time therefrom about 2007 to 2011.
I left without, yeah.

Speaker 3 (25:18):
What was it like at that time?
Because, again, this is earlyTwitter.
This is like maybe two years.
I think you guys launched 2006,but the world got it in 2007.
But the world got it in 2007.
What was it like being atTwitter when MJ passed away and
just kind of seeing the traction, because to me that was like

(25:40):
the coming out part, like it wasevery day for like two weeks
straight.
What was that like?

Speaker 2 (25:45):
Yeah, it was special and, like to be honest, I don't
remember the day MJ passed andthat all went crazy on Twitter,
but I do remember that year oryear and a half at Twitter where
the world really caught on.
It was a quirky product.
It was quirky people running it, the little bird was cute.
It was a very simple product,but there was an aura of

(26:08):
importance.
We knew at that point that whatwe were doing was like sending
shockwaves through the world andpeople were coming to Twitter
to find out what's happening,what's going on and it it.
So that combination of likequirky, fun, simple, coupled
with like, what we're doing hereis going to really make a
difference, you know, on ourplanet and for the people and
for these communities, um, um.

(26:29):
And so it was a really specialtime to be there because, you
know, that was a big moment,obviously.
But at this point, twitter wasstarting to go global and we had
, like you know, uprisings, thearab springs were happening.

Speaker 4 (26:40):
We had yeah, I was, I was gonna bring up the arab
spring thing.
Yeah, I mean, that was that'swhen I was like, oh shit,
because remember, they had cutoff communication yep, and that
was the only there and then theywere communicating with each
other yeah, twitter, and like Iwas like, oh, this is okay, this
is just not talking shit aboutbasketball, that's right.
That's when that's right.

Speaker 2 (27:02):
That's when, like traditional media, news outlets
and journalists started comingon and really validating.
This is a place to find outwhat's happening in real time.
And you know to the point,earlier still today, big news
breaks.
I go to Twitter right then tosee, like, what are people
saying about it and, like youknow, I'm a meta now and I use
threads a lot, but, like,twitter still has that kind of a

(27:23):
stranglehold on, like, what'shappening right now.
What do you need to know?
It was a real special time tobe at that company.
I'll tell you, though, similararound then, the real special
moment for me was the day thatSnoop Dogg rolled into lunch at
the Twitter offices, broughtabout as many people as worked
for the company with him in hisyou know, in his crew we had

(27:44):
just got some new offices and wehad a little DJ deck like uh,
you know, overlooking kind ofthe lunch tables and the
cafeteria.
And so Snoop brings his, hisunreleased vinyl it was going to
come out and start putting onsome music.
His whole crew starts rollingbig fatties and passing them
around.
I'm telling you, this office isthat I think there's maybe
video on YouTube, so, but thisoffice in San Francisco, I mean

(28:04):
it was big office and it was hotbox like you never seen
security in the fire marshalshut the whole thing down.
But after that Kanye rolledthrough and the president of
Russia and presidents of theUnited States, and right after
that it was just this neverending line of people that
wanted to come to the office tosee where is this all happening.
It's funny because the officewas just a bunch of nerds like

(28:25):
me cranking on code and workingon stuff.
But the effect that product hadthrough the world, man it was,
it was meaningful.
And I'll tell you justpersonally, and it's kind of
hard to say, but I've been kindof craving that, like the
dopamine of working for a placelike that at a moment like that,
ever since, you know, and thenmaybe that was just a special
moment in time, lightning in abottle.
I'm not sure I'll everrecapture it, but I mean that

(28:45):
was a real special time to bethere.

Speaker 1 (28:47):
That's going to be hard to recapture.
The negative side could be said, though, that Twitter did a lot
of positive and changed the waywe communicate, but it also
changed media forever, in thatwe all looked at our local news,
we all watched TV.
There was always a certain wayto get the news, and it was, I

(29:08):
thought at least, a lot moreunbiased at that point.
With Twitter on there, itbecame open that anybody could
basically talk about anything inany opinion, and in some ways
facts didn't matter as much.
So it is kind of a scary sidetoo, because people are not
going to remember how we used toget our news, and now it's
changed forever A hundredpercent.

Speaker 2 (29:27):
I mean it's, it's, you know, the with with the pros
come the cons, and noteverything is is roses and, like
I said, we back then, you knowto, to my discredit, I wasn't
thinking about ways in whichthis could be manipulated or
used to manipulate people.
Or, you know, terroristorganizations still to this day
using Twitter to organize, to gokill people.
I mean it's, it's, it's thatliteral and you know we weren't

(29:49):
thinking about that um then.
But also I still believe youknow Twitter was a net positive.
I think, like you, know, and Ireally believe, like and this is
kind of, you know, channelingRick Rubin, he always says like
ideas are in, like, in the etheraround you and you know, if you
, if you have one, you shouldrun with it.
If you don't run with it,someone else may.
And I think we've seen a lot ofexamples of like, even in, like

(30:10):
, popular music over you know,the last century.
Like sometimes, uh, you know,similar types of music will pop
up in different kinds of thedifferent parts of the world.
Uh, that had no connection toeach other, and so it's like I
feel like if Twitter didn'thappen, I think that idea would
have, uh, would have likelyhappened.
That said, you know, I wishwe'd go back and put some

(30:31):
protections in and, you know, dothings a little bit differently
, but maybe that would havesquandered the deal.

Speaker 1 (30:34):
So it might have.
It might've never got to whereit was yeah.

Speaker 2 (30:37):
Comes to bat and and uh, you know I still, to this
day at Meta, often talk aboutthe lessons I learned at Twitter
, just to make sure that likemoving forward.
You know, we get all excitedabout technology and like, with
AI happening right now, we're ina real moment right now with
technology, like let's just takea breath, slow down a little
bit and make sure what we'redoing.
You know, let's think throughall the ways in which this can

(31:00):
go horribly wrong, which is areally hard mindset to employ
when you're really excited abouta new thing.
But I've learned that that'sthe best way to do it.

Speaker 1 (31:08):
Yeah yeah.
So what made you leave then?
So Evan Williams decides toleave.
Do you go because you had justbecome such a fan and loved
working with him, or whathappened?
What made you leave?
Twitter?

Speaker 2 (31:22):
Yeah, well, me and Ev became pretty close friends,
just kind of cut from a similarcloth and the things we were
into.
And he was, you know, he was anidol in my mind.
You know little nerd from Texasand he'd done all these big
things, he kind of making ithappen out in Silicon Valley,
and so um, of the Twitterfounders him, jack and Biz me
and Ev were definitely theclosest and um, and he really I

(31:44):
owe a lot of my career to him.
He really saw some potential inthis, this little Texas, and
really put me on and reallyhelped me show what I could do,
and so it's a well-documentedstory.
Now there's a book about itwhere he was outed for the
company.
He was the CEO.
He actually when it firststarted they let Jack be the CEO
, he was the engineer.
But very early Ev was like holdon, I can't have my engineer

(32:07):
running this company.
So Ev kind of took the reinsfrom him.
And then Jack orchestrated alittle bit of a coup and took
the reins back from Ev.
Ev became a CEO later and thenDick Costolo and like it was
kind of this rotating cast.
So by the time Ev left, I thinkthe board was just kind of
ready to turn the page fully.
And Ev had got it to where itwas, which at that point was a
public company.
And so Ev bounced and Iremember the day he left.

(32:32):
I said look, I know enoughabout you to know you ain't
going to rest.
And by this time he was abillionaire.
He didn't have to do anything.
But I was proven right.
He went to Tahoe for a coupleof months to try to be like a
snowboard bum, but that wasn'tworking out all these ideas.
And after Blogger and Odeo andTwitter, like, Ev is just

(32:54):
fascinated and maybe evenobsessed by this idea that, like
, facilitating the exchange ofideas and stories in the world
is one of the most importantthings that he can do and that's
kind of his mission to bring inall these products.
Kind of scratch a similar itch.
So I knew he wasn't done.
So I said, whatever you'redoing next, like I'm with you,
homie, let's go.
And he wrote me back that day.
He was like I got an idea.
I remember his email.
I got an idea.

(33:14):
He said you want to rebuild theinternet and that's all he said
.
And so I was reporting to theVP of engineering.
I told him that day.
I said this is my two weeknotice.
I'm going to rock with Ev andhe was like, what's Ev doing?
I was like I don't know.
But I doubted Ev.
The first time, as I saidearlier, when he asked me to

(33:35):
move out there early at Twitter,I doubted him.
And the second time I said I'mnot.
I'm with you on this ride.

Speaker 4 (33:40):
You learned your lesson.

Speaker 2 (33:41):
I learned my lesson A hundred percent.

Speaker 4 (33:43):
I respect that.
I respect that, yes, sir.

Speaker 2 (33:47):
Yeah.
So he left and I joined him andwe restarted obvious
corporation.
Remember, I told you obviousone it was supposed to be like a
holding, an umbrella company.
Twitter was going to be oneproduct of many.
Well, now, post twitter ebbs abillionaire, he's got all this
cachet.
He's bringing along people likeme and then some of the people
they knew to kind of startsomething new.
And so we started obviouscorporation v2 and we just

(34:09):
started opportunistically,bringing in smartest, most
creative people we knew and justdorking around with different
ideas and we built probably 10or 11 different products.
But the first one was whatbecame Medium, the blogging
platform, you know, and at thetime, you know, we kind of joked
in that Ev had done blogger,which was long form writing.

(34:31):
They did Twitter, which waslike short form writing, and
it's like maybe there'ssomething in the middle, and so
we called it Medium, but alsolike the Medium is the message.

Speaker 1 (34:39):
I didn't know.
That's where the name came from.
That's dope, that's dope,that's dope, that's dope.

Speaker 2 (34:46):
Funny story about that.
The other competing name wasgoing to be Matter, mattercom,
but the oh God, I'm drawing astupid blank here Mark Cuban,
ownmattercom.
And so Ev pinged Mark and saidhey, can I get this domain from
you?
I think it was going to sell,but it was going to be a time.
We ended up falling in lovewith Medium anyway, and so we

(35:07):
built a bunch of differentproducts.
Medium was kind of the firstone, but then we thought we
can't just launch anotherblogging platform.
This has been done.
So we spent about a yearlooking for different angles,
different products, built a lotof different things.
We kind of went back to thatoriginal idea and really felt
like there was a need, partlybecause of what we launched with
Twitter.
To your point earlier how peopleconsume news, ev uses an

(35:28):
analogy that really resonatedwith me, and still does, which
is like, anytime you'reconsuming anything, whether it's
food or media, like you shouldhave a healthy balance in your
diet, you know.
And so, like you know, I don'teat super healthy, but generally
healthy, but also candy and icecream, and I'll have a soda
every once in a while.
And like same with my mediaconsumption, like I'm trying to,
you know, be informed from uhuh, trustworthy, respectable,

(35:49):
you know facts online and anddoing all these things, but also
still use Twitter and Instagramand so, like Twitter was kind
of like the candy of the media.
Consumption, you know, and likeI think you know, in
coordination with you knowhealthier things you ingest from
the media, like it's probablyfine.
But when Twitter became thatbig it was like now all the
media is like this, like candy.

(36:09):
You know, all the media is likecandy now.
So we felt like we couldpotentially offset that a little
bit by launching a platformthat really incentivized deeper
thought, more intellectualwriting.
You know, well-informed takesand you know, and just longer
takes.
You know it's easy to crank out140 characters.

(36:30):
It's not easy.
I mean, some people have it'slike an art.
It could be an art Right now,but with Medium we really
targeted who are the thoughtleaders in industry.
How can we potentially changeculture and change minds around
the world?
By letting people type and in away that you didn't have to
start your own blog and marketyourself and brand yourself?
And you could, that you didn'thave to start your own blog and
market yourself and brandyourself.

(36:51):
You could write into thisnetwork that already had
millions and millions of readers.
And so even the business model.
We said from the get-go weweren't going to be an
advertising business model.
I think the business model thatbig tech companies, including
Twitter, employ todayincentivize sensationalism and
click-baity headlines.
That's how they get their adclicks and their money.
So we said we're not going todo ads on Twitter, on Medium,

(37:13):
sorry.
So we played a couple differentideas.
But right from the get-go wesaid we want this to be a place
where people are going to comehere and feel like they're
getting the meat and potatoes oftheir digital diet, you know.
And so and they just celebratedMedium just celebrated, I think
, their 12 or 13 yearanniversary.
Medium to celebrate I thinktheir 12 or 13 year anniversary.

(37:33):
So, like man, that's, that's athat's forever in in tech.
And you know, in tech, years um, and still going, still growing
.
They do have a business model.
Now it's a profitable companyas of this last quarter how do
they make money?

Speaker 1 (37:41):
because I'm not sure right now.

Speaker 2 (37:43):
Yeah, so it's a member, it's a membership, so
for five dollars you're likeunlimited membership.
I think they're gonna toexperiment with some different
tiers of membership, differentthings, but right from the
get-go we wanted to incentivizewriters to write meaningful,
impactful takes.
And so, still today, you can goto Medium today and write an

(38:04):
article you think is going to begood.
You can put it behind thepaywall if you want, and all the
people that read you are goingto get a little cut of that.
You know, not that muchdifferent than, like you know,
putting your music on Spotify,but you know, for for a
different industry and manreally proud of what what that
became for sure.

Speaker 1 (38:20):
Wow, that was part one of our conversation with
Sturman.
Don't miss part two.
All right, folks, that's ourshow.
Tune in to Unglossy, the codingbrand and culture, on Apple
Podcasts, spotify or YouTube,and follow us on Instagram, at
UnglossyPod, to join theconversation.
Until next time, I'm Tom Frank.

Speaker 4 (38:41):
I'm Jeffrey Sledge.

Speaker 3 (38:44):
Smicky that was good.

Popular Podcasts

Cold Case Files: Miami

Cold Case Files: Miami

Joyce Sapp, 76; Bryan Herrera, 16; and Laurance Webb, 32—three Miami residents whose lives were stolen in brutal, unsolved homicides.  Cold Case Files: Miami follows award‑winning radio host and City of Miami Police reserve officer  Enrique Santos as he partners with the department’s Cold Case Homicide Unit, determined family members, and the advocates who spend their lives fighting for justice for the victims who can no longer fight for themselves.

Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

Stuff You Should Know

Stuff You Should Know

If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.