From Garage to Acquisition: Tales from Two Multi-Venture Entrepreneurs | The Pair Program Ep30

Curious what it takes to be a startup founder?

In this episode, we hear from Ryan Rowe and Adam Meghji – successful entrepreneurs who have each spun out multiple successful startups.

They discuss:

• Their journeys into entrepreneurship.
• The challenges they faced as they took their startups from 0 to 1.
• Things that were a great success (and things that went wrong).
• The process of finding co-founders.
• How to know when its time to make an exit.

And much more!

About our guests:

Ryan Rowe is the CTO and Co-Founder of Archive. A three-time founder, he has over a decade of experience designing and developing innovative technology. Ryan began his career as a product designer, where he became obsessed with creating the best user experiences. After his first company was acquired by Palantir, he launched several new product initiatives for the renowned technology company. Since founding Archive, he is committed to building the best technology and UX experiences for fashion resale.

Adam Meghji is a seasoned CTO and technology executive, hiphop DJ, and father of two. He's helped launch and scale several startups from inception to exit, including his past venture Universe which sold to Ticketmaster / Live Nation in 2015. Currently, Adam is Co-founder & CTO at Peggy, the premier marketplace for buying and selling investment grade art, secured by AI artwork authentication.

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Welcome to the Pair program from hatchpad, the podcast that gives you

a front row seat to candid conversations with tech leaders from the startup world.

I'm your host, Tim Winkler, the creator of Hatchpad,

and I'm your other host, Mike Gruen.

Join us each episode as we bring together two guests to

dissect topics at the intersection of technology, startups, and career growth.

Uh, hello everyone.

Welcome back to another episode of the Pair Program.

I'm your host, Tim Winkler.

Joined by my co-host Mike Gruen.

Mike, how's it going today?

It's going great.

How you doing?

I'm good.

I'm good.

You know, do you know what today is?

No.

No.

Um, it's National Wine Day today.

That expensive.

I'm not a big wine fan.

Not a not a wine guy.

Not a wine guy.

No.

It's funny

cuz when I was in my twenties, I was much more of a wine guy,

and I think that's a little unusual.

I think more people go in, get into wine as they get older.

But, uh, in my twenties, uh, actually that was like one of the

first trips my wife and I did.

We went through, uh, Northern Virginia to a bunch of wineries and had a lot of fun.

Um, but yeah, for whatever reason I've sort of, my tastes have

changed and, uh, now I'm more of a whiskey guy than a wine guy.

There you go.

Well, yeah, there's plenty of wineries out this way and

in honor I will be toasting with a little albarino for the episode.

So, um, uh, let's, let's give our listeners a, a little bit

of a preview of today's episode.

Uh, so today we are going to be kind unpacking this art

of serial entrepreneurship.

Um, and we've got two excellent guests with us.

Both are seasoned serial entrepreneurs.

Who have started multiple startups, uh, they've experienced successful exits.

Um, I would guess maybe some failures also along the way.

Um, but I'm pretty jazzed to hear their unique journeys and shed

some light on what it takes to, to kinda launch multiple ventures.

Um, so, so for our guests, we've got Ryan Rowe, um, a three time founder.

He has over a decade of experience designing, developing

innovative technology.

Uh, Ryan started as a designer, uh, obsessed with creating

the best user experience.

Uh, he launched and sold his first startup Kimono labs to Palantir

and is now co-founder and CT o of archive, uh, a resale technology

startup based in San Francisco.

Uh, we paired Ryan up today with Adam Megi, uh, I might've butchered that last

name so you can correct me if I, if I did.

Um, uh, another repeat founder, he, uh, who turned his love from

computers into entrepreneurship.

Adam sold his first startup universe to Ticketmaster and is

now focused on authenticating and selling pieces of contemporary

artwork with his current startup.

Peggy.

Uh, and a fun fact, uh, uh, I found out in my intro call with, um, Adam,

is that he is also a DJ and a musician.

So, um, that's pretty sweet.

Maybe he'll rip, rip some tracks with us here, uh, during the episode.

And, uh, it's, it's no surprise man, that you are, uh, creating and

building with, with that type of, uh, background deep rooted in your d n a.

So guys, thanks both for, for joining us on the PAIR program today.

Thank you.

Thanks so much.

All right, so, uh, before we dive into the discussion,

we do like to kick things off with a segment called Pair Me Up.

Um, this is a segment where we go around the room, we'll kinda

spitball a couple of, uh, oh boy.

See fir first time producing here.

So happens when a producer leaves.

Um, just on vacation.

Just

on vacation.

Um, yeah, we'll go around the room.

Shout out to complimentary pairing.

Mike, you kick us off.

Uh, what do you got for us?

Yeah, uh, I had a completely different pairing until

we tried to get this episode going.

Uh, so I'm calling an audible.

Uh, my pairing is gonna be, um, troubleshooting and divide and conquer.

Uh, I've found that Divid and conquer is always the best way to

troubleshoot any type of problem.

Uh, split whatever you have in half.

It's like the, one of the first things I learned in computer science and like,

whether it's recursion or whatever, you just keep cutting the problem into smaller

and smaller problems until whatever.

And so, Uh, yeah, for those that don't, can't figure it out.

What problems?

Yeah.

What problems?

Yeah, we have problems.

No, no technical problems, uh, trying to get on today, so, yeah.

Um, but yeah, definitely divide and conquer and, uh, troubleshooting.

Yeah.

Dig that.

At least it's not as bad as, um, you know, the first time I actually

tried to, to, to produce this was before we had our producer.

I forgot to push record for the first 10 minutes.

So we had to, everybody had to kind of just stage talk what they had

just said for the last 10 minutes.

It was pretty embarrassing.

Um, but, uh, Cool.

All right, I'll, I'll jump in.

So my pairing is going to be, uh, Tim Winkler and Sunburns.

Um, and I did just refer to myself from the third person, but

it's, uh, it's, it's inevitable.

Um, you know, summer is kind of upon us, so spending more time outdoors.

Uh, and as a result, I'm pretty quickly reminded of how pale and and

sensitive my skin is to sunlight.

So, just out this past weekend and just doing some, some work in the

yard, I felt like it was more than an hour, uh, cleaning some gutters and,

you know, wearing a tank top and, uh, um, you know, cut, come back in.

And I'm pretty much burnt to a crisp.

So it's that time of year, uh, where I'm lathering up on SPF 90.

Uh, we're headed to the lake this weekend, and so I'm, I'm pretty

confident that it's, it's, it, it always ends in, in a sunburn.

Um, but, uh, no matter how prepared I am, so that's, that's my pairing.

Um, I'll, uh, I'll pass it over to our guest now.

Ryan, why don't you give us a, a quick intro and tell us your

pairing.

Yeah, totally.

I, I find it very hard to believe, Tim, that that's your favorite pairing, mean.

That's, we'll take it.

Yeah.

Um, yeah.

So I'm Ryan Rowe, uh, co-founder and CTO of Archive.

Uh, tell you more about that later.

Uh, for my favorite pairing today, I guess I'd say surfing and warm water.

Mm-hmm.

So, I live in la I love to surf.

I live right next to the beach, but.

Every once in a while I go on vacation and I get to do it in 85 degree water

and it's absolute joy and I look forward to that every time I do it.

And it's just an incredible experience.

So putting those two together is my favorite.

Better than being sunburned after.

Definitely.

Yeah.

Always happens.

Yeah, that's true.

I actually could have gone with sunburn and aloe aloe vera.

That could have been, yeah, the, the favorite pairing, but relief combo.

Yeah.

On, on the, on the surfing.

So do you wear a, a wetsuit out there,

or No.

I mean, I do here and yeah, that's, that's, uh, that's part of the

joy, you know, it's not just being warm in the water, but you're like

totally free and boy shorts, you're kind of just jumping in the ocean.

It's, it's so

good, that's all.

Did you grow up

surfing?

No, I didn't start till college.

I went to ucla, so that's where I kind of started.

I.

Getting in the water and then, yeah.

Now it's been about 20 years and I've

heard people refer to it as, uh, almost like therapeutic

or, or like a form of meditation.

Do you, do you find that, uh, when you're out there in the ocean?

Yeah.

I mean, you can do it for hours and mm-hmm.

Especially if it's warm water, another benefit.

Right.

If you're freezing your ass off, it's not a, not a, it's not idea.

You're kinda in and you're out.

Um, but it is, I think like looking back at the, especially if you're in

somewhere tropical, beautiful, you've got like the mountains, the jungle,

you're kind of looking at it from the ocean is a really unique vantage point.

And it is very, it really feels like you're.

In nature, in this kind of unique way.

Um, and you can do it for hours and it's just, it is meditative because of that.

Yeah.

Yeah.

I, I do a bit of snowboarding.

I, I feel some similar kind of feels when I'm out there on the mountain.

Uh, totally.

It's certainly therapeutic.

Cool.

Well, we're, we're pumped to have you on.

Um, and then we've got, uh, Adam, Adam, uh, good to have you on,

and, uh, you wanna give us a quick

intro in your pairing?

Thank you.

Yeah.

Stoked to be here.

I'm Adam Maggy, co-founder and CT O of Peggy, which I'm sure

we'll talk a lot about later.

You know, lifelong hacker and entrepreneur, developer

and many other things.

Father, uh, dj, et cetera.

My pairings, uh, my pairing is music and coding.

Um, which I think, you know, to many might seem like sort

of an obvious pairing, right?

Like it's no secret that programmers, developers, we all love to put

our headphones on code, right?

Um, but then I think for me, I also like my experience as a musician, as a dj.

I think, like when I relate to music, it's also from like the creator perspective.

Yeah.

And same with coding, right?

And these two pursuits have, I've been intoxicated by them, like my whole life.

Like I grew up playing piano, which I sucked at, played guitar, you know, also

sucked at that, you know, and then DJing was like, really what clicked, right?

And this is like decades ago.

But, um, I've just been DJing and a music producer, um, you know,

more, more than half my life now.

And also coding, you know, the whole time too.

And I love putting the headphones on, running long mixes on YouTube

and just like getting into that zone.

Now as a CTO these days, I, I'm finding like, yeah, less and less time to get

into the zone cuz I'm interrupted with meetings and other important things too.

Um, you know, I still hack on personal things as well, but, um,

certainly like listening to music.

But then also, you know, when I'm done working, when I'm done coding, when

the baby's asleep, I, I come back in my office here so, And I'll fire up the other

laptop and I'll fire up audio software or sometimes not even software, I'll

just fire up the hard, like the hardware and I'll just get loose on like music,

making music and just decompressing.

And so yeah, the two things for me kind of occupy, they co inhabit the

same parts of my brain and I think they both bring me like the outcomes

bring me deep joy and uh, yeah.

And they sort of have this like complimentary effect I think they may use.

Similar parts of my brain.

It's hard to unpack them because they seem sort of foreign, but mm-hmm.

They are complimentary.

So I

totally agree.

I, it's actually just this week I had a one-on-one, or maybe it was last Friday,

uh, with one of, one of the guys who reports to me, who's also a musician,

and we were talking about this for a long time, and I've had that theory of,

um, Not just the listening to music, but musicians and the correlation between

them and being good software engineers.

And over the years, all the way back to my first job where one of my coworkers

was a, an amazing musician and all the way up, um, just every job, there's

always a handful of really amazing engineers who are also amazing musicians.

And I think there is something there that correlates.

I think it's the creativity.

I think there's something to music itself that's like this esoteric language,

um, but it's really logical at the same time and really mathematical.

I think there's, there's just a lot there.

Um, I've noticed that so much over my career, so I'd love that pairing.

Yes, that's

spot on.

Agreed.

And with rock climbing bouldering.

Mm-hmm.

You know, that's another common pairing.

It's like, like bouldering and, and like developers.

Mm-hmm.

Mm-hmm.

Like co-founder Craig, you know, um, a while ago we would, you know, try

to be sourcing, um, I r l developers, you know, in, in our city, in Toronto.

Typically he would meet people at the climbing gym.

Mm-hmm.

Or he would find at the climbing, he would take them there.

And part of the like, developer hiring the wooing process sometimes involved,

like rock climbing with people.

Cool.

Yeah.

And it was a pretty, it's a pretty compelling, you know, way

to meet and get to know the ceo.

Right.

So that's another, another pro tip.

Yeah.

Yeah.

It's al also, uh, skiing, I've seen a lot of, uh,

uh, engineers, founders got, you know, folks in venture too.

Um, you know, I went out for a ski trip out in Utah with, uh,

a crew of, of folks from Austin, from the Austin startup scene.

And uh, next thing you know, there's folks meeting up from, you know, SF scene, like

everybody's there and there's a probably like 25, 30, you know, tech startup,

tech engineers, founders, like all kind of getting after it on the mountain.

Something about that.

That's, um, Uh,

yeah.

Seems, seems synonymous.

Yeah.

I mean, co my co-founder and I both spent the first two winters

of our, of our company in Utah.

Oh, did you?

For skiing.

Oh, good stuff.

Yeah.

Good stuff.

Totally get it.

Cool.

What resort?

Uh, what?

Yeah.

Uh,

we were, we were staying in Salt Lake.

We had a house in Salt Lake and we were just kind of 20 minutes

up from Alta Snowbird, so we spent most of our time there.

Sweet.

Yeah.

Oh, it's

beautiful.

Cool.

All right.

Um, I like it.

I think, uh, I think that's a good wrap on the, the first segment.

Um, so we're gonna jump into the, uh, the heart of the discussion at this point.

And like I mentioned, we're gonna be talking about, you know, serial

entrepreneurs, um, looking to kind of uncover what, you know, what is that makes

these guys tick, um, and want to continue to pursue this lifestyle of pure chaos.

Um, jokingly, but sort of joking because, you know, we, we talk to a lot of founders

and, and tech leaders and entrepreneurs on the pod, and it's, you know, it's

no secret that the lifestyle of an entrepreneur can be, you know, stressful

and a lot of ups and downs, mood swings.

And so, you know, what is it that keeps these types of individuals so hooked

and, and continuing to come back.

Um, so we'll hear the, the breakdown of, of the guests, uh, each, each of

their kind of entrepreneurial journey.

Uh, we'll talk a little bit about like risk taking, you

know, learning from failure.

Um, the, the, the required mindset that it takes and, and a lot more.

But, you know, with that, I wanna start with, with you Ryan, and, and, and this

topic actually was your idea, uh, you recommended serial entrepreneurship

and, and why you keep finding yourself, you know, starting companies.

Uh, so I'll, I'll start with you and, and, and have you kind of provide our listeners

with some context on your journey.

Um, so maybe try to keep it, you know, three to five minutes on,

on the breakdown of your journey.

And then I'll ask the same from you, Adam.

Uh, and then we can kind of riff from

there.

Cool.

Cool.

Thanks, Tim.

Yeah, so I, I mean, I think it is to your point, a a little bit of a disease.

You know, it's, it's one of these things that you know, is going

to cause you stress and pain and have its ups and its downs.

But there's just something I feel like, you know, once you've

experienced it once and once you've kind of seen that play out, it's,

it, it becomes the way that you.

I don't know, manifest professionally.

And for a lot of us, and this may be true for you too, Adam, going between, you

know, back and forth from entrepreneurship to being an employee at a larger company,

you, you find that there are things that are just somewhat intolerable mm-hmm.

About the, the frameworks of the larger companies.

And I know that's, that's, uh, most entrepreneurs will tell you that,

but I think everybody's experience of that is different and the

reasons for that are, are different.

So yeah, I'll tell you a little bit about my background.

I.

I guess even before starting my career, I went straight from an undergrad degree

in math to a PhD program in math because I didn't want a job, I didn't want

to think about going to career fairs.

It just made sense to me to keep doing what I was doing in undergrad.

And when I got to grad school, which was at Columbia in New York,

I very quickly learned that the path was very much narrowing.

The set of things you can do with a math PhD is quite small and I, I

did not want to be a math professor.

I, I, I very clearly kind of started to see that and I

also just didn't want to work.

A job where I was using those skills just because of like how arcane it is.

Like the number of people I could impact with what I was doing was

so small and that was so sad to me.

My, my professor told me he was really excited about our research findings

cuz there was this one other research group on earth that would use them.

And that, that, that moment was when I decided I'm, I'm out of here.

And so I discovered, uh, kind of user experience design totally by luck.

There was a class at, at Columbia that I took on the topic, became

infatuated with it, and found myself at a company called Frog Design.

Um, and so that, that I, I stayed there for seven years, half of that in New

York and half of that in Shanghai, China.

And I had this incredible experience learning about tons of different

industries and effectively going through what looks like an entrepreneurial

journey, but like very much.

With guardrails because every time we engaged with a client, you had to

sort of do the need finding, talking to customers, figuring out what to

build, then develop a concept, and then figure out how to bring it to market.

But it always ended right there.

And it was like very, very frustrating to me that we would

hand these presentations of, this is how you build this business off.

And they would get kind of mangled and the company would never actually do the

thing in the way that we envisioned it.

And so that's why at the end of seven years, I was like, I'm,

I'm gonna try this on my own.

Uh, I, I really think I can do this.

And I wanna see what it's like to actually put a product in

the world and iterate on it.

Like, even, even before doing that, my first.

I wouldn't call this entrepreneurial pursuit, but when the App store first

launched in 2008, I built an app called Tip Star, which was actually one of the

first tip calculators in the app store.

And it was wildly popular and it, it, it literally had like

hundreds of thousands of users.

And this, it was free.

I made no money off of it ever, but it was just me putting something in the

world and having, not that this is much impact, but like actually having people

calculate their tips using your, it was a really good feeling and it, it

made me realize like, I can maybe go do something that is a business and that's

when I started my first business in.

Uh, 2014 called Kimono.

Um, we were building a web scraper, uh, that was very usable by kind of anyone.

So it was to try to lower the bar for that type of activity.

We went through this kind of insane experience.

We, we flew to California, we went through Y Combinator.

We raised a ton of money knowing absolutely nothing

about what we were doing.

We got an acquisition offer from Google within two weeks of launching,

like it was literally an episode or a season of Silicon Valley.

We experienced it all and it all culminated in a, in an, in an

acquisition by Palantir, which, uh, you know, was very bittersweet.

And we'll probably talk about what that looks like later, cuz we might,

we might have a topic on that later.

Um, and since then I've kind of been working on many different ideas because

I think the thing I learned through that first process is that really

you have to care about the thing that you are building that first.

Product I was building at Kimono, I was excited about it, but it didn't

matter to me whether or not it existed.

So I didn't, didn't get me up in the morning.

And so my latest company, um, that I founded with, uh, somebody that I met

who had already been kind of thinking about this idea called archive, we're

working on a problem that actually has a climate impact focus and mission.

And, and that's, that's I've found, has, has been a truly different

experience because every day I'm motivated by ultimately what we

will be able to achieve with it.

And as a result, the company is going a lot better than, than the past companies,

uh, that I've, that I've started.

And I, and I think there's just this sort of cohesion between how I feel

about it, how my co-founder feels about it, the mission we're going after.

And it's okay that it's a journey that's gonna take years and we're

not in a, you know, in a sprint.

It's a marathon.

And, um, it's, it's been a really great experience.

So, I'll, I'll leave it there and we can talk more about the rest later.

Yeah, that's awesome.

Uh, couple of quick hit questions, um, and then we'll pass it over to

Adam, but, um, how long were you running kimono before it was acquired?

Two years.

Two years.

Wow.

That's quick.

Yeah.

Yeah.

Um, very And then how long have you been running?

Um, archive archive's

been two and a half years at this point.

So

already quick hits already past that.

Yeah.

So Quick hits, uh, uh, funded, uh, how many in headcount?

Yeah, so archive, uh, so we started it kind of during

the pandemic 2020 end of summer.

Um, great time to start a company cause you've got a lot of time and

a lot of space to kind of think.

Um, we're now, uh, we've raised about 25 million across a few rounds.

Uh, we've got 35 people.

Were distributed all over the us.

We work with 40 different fashion brands in seven different countries, helping

them build secondhand marketplaces.

So we'll work with a brand like the North Face and users can go to the North

Face renewed and buy used products and we power everything about that program.

So the site that the users are going to, but also all of the

like warehouse and inventory management software and everything.

You'd need to run that as a business.

Oh, creative,

really neat.

Um, cool.

I, yeah, I've got a lot that we can, uh, dissect from there, but let's,

let's transition to Adam, Adam.

Uh, why don't you give the listeners a little bit of, uh, context

and share your, your journey.

Yeah, I'd love to.

Thanks for the opportunity.

Um, you know, as I mentioned before, you know, lifelong hacker, developer,

entrepreneur, and, you know, this really goes back to like my origin

story started when I was whatever.

Um, you know, eight, is it, are you eight years old in grade four?

I think so.

I think I was grade four.

This is like circa like 89 or 90.

Um, my dad comes home, he throws an Amiga on the floor.

And so I had never really, like, I was kind of the nerdy kid, um, when

all the kids in my neighborhood like, you know, played hockey and

were like, cool and this and that.

I was like kind of the nerdy bookworm.

Um, and computers weren't really a thing then.

So I, I felt lost as a kid and like I'd always be picked last in

sports and all these things, right?

And I was, you know, creative in that.

But, um, that wasn't super celebrated in the eighties.

Like it maybe it is now.

So, um, I think when, when I came across that computer, something

magical happened, I was just curious like, what is this thing?

And then I, you know, booted it up and then broke it.

And then every, every week or two I would have, I would've like, you

know, mangled the hard I, I would've formatted it, not even knowing what

I'm doing and just clicking wily.

And then, you know, my, my dad was a good sport.

He would take it back to the warranty, get it wiped, you know,

you know, like brought back fresh and then I'd go reinstall everything.

So, you know, I was just like a kid tinkering.

And that was, that was sort of the obsession.

It was like, it just felt like endless Lego that I could just

continue to play with and build with.

Um, which I think a feeling that many of us can relate to.

Uh, there was, I think one of my earliest like programming memories was when.

You know, I was supposed to be studying, um, cause I'm, I'm from Waterloo,

Ontario, Canada, you know, we learned French growing up, so I was supposed

to be learning my French conjugations of all my verbs, past, present, future.

Um, it, it gets quite boring and typically it's just you, you write them out and

then you like make your own flashcards.

So typically you make your own flashcards, but I'm sitting there with

this computer in front of me and I'm like in grade four or something and I'm,

I, I wanna do anything but flashcards.

So I'm like, okay, well let's just try and use like Ami basic.

So I, my first program was just like a way for me to read in, you

know, the answer and then it would prompt me and I'd type it in.

And if it matched then, you know, I get a point.

And if it doesn't, then I lose a point.

So I just made it, it was more interesting to make a game about learning French

than it was to actually learn French.

I eventually learned French, but I continued to learn programming even more.

And so yeah, that's kind of like a memory I haven't really shared too much of.

That was certainly like a, an early, early, maybe the first like aha

moment when I was like, Hey, I'm scratching my own itch here now.

Of course, there's no real distribution for that.

I didn't turn that into a startup idea.

Um, probably just deleted the source and rebuilt it and refactored it later.

But then a couple years later, you know, I'm, I'm running a B B S, um,

couple years later I'm in high school.

Um, you know, I'm starting to like branch up beyond that.

Internet became a thing.

Um, you know, and then I guess like in the Double O's was when I started,

um, let's say founding things.

You know, I was doing internships and co-op and all that at the time and

was in school for computer science.

But I was more fascinated by, you know, using these programming like things.

This is the, in the like PHP days, right?

Like early, early PHP days, you know, I'm able to make, I'm able to use PHP

to create websites like dynamic websites for my friends who are artists, creatives

who don't have a home on the internet.

Like this is in early Oh, ohs, right?

I had to get them set up with like Hotmail addresses, uh, even just to get online.

So I'd be like, Hey, email me your like, You know, whatever, email me, like

just pictures of your art or your like emailing me your rap or whatever, right?

But then you'd be like, I don't have an email.

I can't attach a file.

Like, what are you talking about?

So I'd have to like get 'em set up and yes.

Then I could eventually, you know, onboard.

So I was helping on-ramp people on the internet and then, um, yeah,

and then helping give them a home before they could self-publish.

And so I, I made a community with some of my, my best friends.

We also would dj, you know, just a bunch of creative kids and one of them was

a nerd and so we all kind of like went online and were on the forums and things.

So that was like a really fun way for me to sort of scratch and itch for my sort

of creative friends and my creative self.

Um, yeah.

And then, you know, fast forward I, when, when I was getting, my career started

after school, uh, after, um, university I was working at startups and building,

um, like web apps and then eventually, um, you know, APIs and mobile apps

and platform things, you know, started getting, um, Getting the reps in just

on building, you know, web apps, mobile apps, APIs, everything full stack, right?

And also trying to do all of the sort of necessary skills along the way.

Like whether that involve like, you know, doing, um, doing some design right,

doing some customer success, doing, uh, implementations, helping on sales,

engineering, um, you know, maybe even pitching potential customers, right?

And trying to do all those things to get like a more well-rounded

experience than just like letting p the PHP code speak for itself.

And, um, yeah, after working, like in small startups, working alongside the

founding team, typically, you know, eventually kind of felt like, Hey,

maybe, maybe the next frontier is for me to sit, you know, on the, on the

other side of the, of the desk and, you know, maybe be exposed to some

of the things that you don't, that are maybe you're insulated from when

you're a, a developer or an employee.

Like, you're not necessarily aware of what the burn rate is, or, you know, the,

the, what the fundraise situation is or.

Um, all the other surprises that may get sprung on the founding

team that, you know, like sometimes you insulate others from, right.

Um, you want to give them a nice, safe, secure environment where they

can do their best work and, you know, not agonize over the things

that maybe we agonize as founders.

So, but I, I wanted that pain for some reason.

And so I think, I thought at first that it would like bring me freedom, but then

quickly realized, yes, it's one of those things I quit my nine to five to work like

24 7 or, uh, something similar, right?

So, but I wouldn't trade it for the world.

And I definitely, like being in the founder seat has allowed me to, um, yeah,

like 10 x my creativity because I'm able to be exposed to all of the problems,

engineering, business and otherwise, and then try and map solutions to them

technical, but also business, you know, and, and just various, like, you just

see the full spectrum of problems, right?

Um, And so, yeah, that, that has, I think that's been a rewarding thing for me.

Um, I, I can't really imagine myself doing something other than being a startup cto

O um, even though if you catch me sort of in the tr soro in a new venture, I

make, you know, lament that I'm like, oh, like there's, I could have done,

like, this is just, you know, what is hap Like this is just, um, irrational

that I would subject myself to this, you know, uncertainty and blah, blah, blah.

Maybe we're bootstrapping it and like I'm, I'm trying to get some code

going so I can try and, I don't know, eventually take a salary or something.

It's just like many moments of, um, so just feeling like I'm

just, this is just nuts, right?

Um, but certainly it's, it's worthwhile.

Um, and in my journey.

So, uh, yeah.

In 2011, I founded a company called Universe, um, which was at first

Universe with two eyes, and then eventually universe.com got got

the domain and uh, yeah, found some product, product market fit there.

Um, grew an event, ticketing platform.

You know, kind of like an Eventbrite, you know, a self-serve ticketing platform.

Um, we did a couple key technical innovations that

were unique to the industry.

We made a third party JavaScript widget that let you sell tickets anywhere,

not just on our own web property, but on your own, you know, WordPress

site or your own, your own website.

And yeah, that was like a key innovation that caught the eye

of Ticketmaster and fast forward, that culminated in an acquisition.

And then I was a VP Tech over there helping bring some of the, some of the

technology over, like post-acquisition, but then also bringing startup

thinking to a 40 year old tech company.

Mm-hmm.

And like, you know, helping, um, j just yeah.

Encourage some of the, the practices that we, you know, that are commonplace in a

startup environment, but not necessarily, um, you might take, you know, they might

not exist in a 40 year old company.

Right.

Like, just sending a pull request isn't something that

you can necessarily do right?

Un until you, um, culturally make that a thing.

And, uh, yeah, after Universe, um, after the Ticketmaster, well, even

at the Ticketmaster in, in that, that was a really wonderful, um, phase of

my career and I really enjoyed it.

Made a lot of friends, um, shipped a lot of cool stuff, wrote a

patent, eventually became like the blockchain guy for Live Nation.

Um, I also did a stint, uh, partway through where I was the fractional

CTO of a, of a crypto company and built a, built a wallet and some

blockchain infrastructure that was eventually acquired by Voyager Digital,

uh, who is now famous in the crypto world, sadly, but you never know.

Um, yeah.

And then my latest venture is Peggy, which, you know, we can talk more

about, but doing it all over again.

Um, you know, my, my same co-founder Craig Fett and I, we started Universe in 2011

and, you know, we started Peggy in 2020.

And, you know, we spent, you know, 10 years building a marketplace for

event tickets and now we're building a, a social marketplace for art.

And so we're able to take some of those experiences and learnings and wonderful

co-founder patterns that we've developed together over the years that that

muscle memory and then bring it to a new industry art, which is very analog

and old school and right for disruption, but nobody's really approached it,

uh, you know, in, in the right manner.

Mm-hmm.

Um, you can't just apply e-commerce playbooks to it.

You can't just do what other people have done to digitize that industry.

It's special.

And so we've, um, created something.

We have a special play that we've, are very excited about and yeah,

hope that this is our big one.

And, um, yeah, excited to see where it lands.

Cool.

Wow.

That's, that's a, that's an awesome story.

And I, I, what I love to pull out of, you know, something that came from both

of you is, you know, this next, this most recent startup, you know, this

is both like passion projects merged with, you know, building something new.

Um, and so I just think that's a, yeah, I, I think that's fascinating because, you

know, this is your second or third go at this and it's like you were, I'm gonna be

real intentional with this next go around versus, you know, falling into something.

Um, which I think is fascinating.

Um, yeah, definitely.

I

wanted to, uh, something Ryan had said at the, or about

the, you know, the first start and then the, now that this one being

something, this, this passionate thing.

Um, one of the things I've noticed, I've worked at startups throughout

all my career, um, and it's interesting to see the passion

of the founders in the beginning.

And then there's this period of time frequently.

It's after like the series C or like once the, once the board really starts

getting involved and putting their fingers into like the direction, I

feel like that's when even you can sort of almost feel it in the founders.

Like they, like it's not there.

Or when that second, like, I'm just curious, like, is that, is that

just my experience or do you think that that's a fairly common thing?

Um,

I mean, I, I, I can't speak because I haven't gotten that far.

Series B seriously.

Um, my first startup was, was acquired pre-series A and

then now we're good for you.

So I, I wonder, um, that, that, you know, that may, that may be the reason.

It may, it may be other reasons.

You know, like you get to a point where it could be that you're obsessed

with the zero to one and mm-hmm.

You know, I.

One of the things that kind of shocked me throughout your story, Adam, is just

like how similar we are in our backgrounds and our interests and the things that,

you know, I built websites for friends.

Uh, I built like PHP web apps because it was fun to solve

problems with the new technology.

Like I, all the things that you said at some point in my, I built actually

a game to help me learn Chinese.

Cause I was, there you go.

Right?

Um, so it's, it, I, I do think there's like a class of founder that, and I put

myself in this class, which is sort of, you know, what I would call the builder.

I, I, I just love making things and I think part of what may be happening at

that series C, whatever stage of company is that you're no longer making thing.

I mean, even at the stage we're at today.

I'm, I'm, I'm not really making things in the same way I was a couple of

years ago, but I'm still, I'm making it by extension because we are still

very much autonomously running.

We're still very much like going into new product areas, new

business areas all the time, and my creative brain is like constantly

still firing like it needs to be.

But I, I think you get to a point where you're, you're so sufficiently

like you've figured out how to build this business and the the things you

have to do completely change and.

I'm not saying that I anticipate, oh yeah, I will definitely be ready to

leave when we hit that stage, cuz I don't know what it will look like or

when it will happen, but that's my sense.

Yeah.

And I think

that there's, like having worked with a, um, number of places where

right there comes that point where the founder themself is like, Hey, I'm not

like, I'm gonna bring in somebody who actually knows to, I I I did zero to 50

or zero to 60, or whatever it is, right?

But like, if we really wanna scale this out, there's somebody

better than me for this.

And you know, and now it's a business.

It's a, it's not the same thing.

It's, um, so it's interesting.

Um, But I think you're right that there's probably some

sort of mentality thing there.

I haven't, uh, there are definitely some who can do both, who can do that

early and then also switch gears and go into the, that other growth stage.

Um, so yeah, wish you luck.

And

I think it's less, I think it's less about like whether or

not you can, and more about whether or not you want like one that's

Yeah.

When it comes to can, it's always, it's always a choice, right?

Yeah.

You can't, it's, it's right.

What do you want to do?

It's a choice.

I, I totally agree with that because even,

even in this experience, I think this is one of the things that went

terribly wrong with my first startup, uh, was that I never really made a transition.

I operated in the same kind of plane of existence the entire two

years until acquisition where I was just still just like a builder.

Mm-hmm.

I had a team of people around me, but I wasn't really leading them to success.

I wasn't, the company was not growing in a sustainable, smart way to actually scale.

My co-founder and I, whereas what I've noticed by very stark contrast

in, in my most recent journey with archive is my job fundamentally

changes every three to six months.

And I'm doing like a completely different set of activities.

And that in and of itself is like a creative learning process.

Mm-hmm.

Which is exciting.

But when I find parts of the job that I have now moved into that I don't

like, I hire someone to do that job.

And then I, I find a way to, you know, now I'm oriented and I'm doing the things

that are exciting and interesting to me.

Maybe someday that dries up, I don't know.

But that's been my experience.

So when you, when you got acquired, you know,

how long were you at, um,

Palantir?

About two years almost to the day.

When did it strike you that this wasn't like the long haul for you?

Was it pretty immediate, pretty quick, or did it take you a little time?

It,

to be honest, the immediate reaction was like

absolute, like bliss and relief.

Not because the exit was great, but just because I no longer am

literally so stressed, I want to die.

Like I don't like nothing act.

I almost had this feeling like nothing matters, this is amazing.

Like of course I'm gonna try to do a good job, but it's not on me to make

sure it doesn't fail, which was like so different and so relieving that.

I actually just enjoyed myself for like a year.

I was also traveling all over the world, living in different countries.

I met my now wife, like it was a great, that's awesome.

But then I think, you know, between 12 and 18 months in, it started to hit me that.

I started to get deeper into like the role I was playing there, which

I was doing sort of an early product.

I was kind of trying to figure out what should Palantir be

building in the commercial space and putting definition on that.

And when I realized that I couldn't run it like it was in my startup,

like there was actually a board and a leadership team that I had to

now convince to do these things and that, and that was not the, yeah.

I don't like convincing people to do things.

I like doing them.

Mm-hmm.

That's when I started to realize like, this isn't gonna work long term

because I, I, there's too much of a disconnect between the, the machine that

that actually steers the company and what I am bringing to the table, and

that's what I needed to get back to.

Sure.

And then Adam, you were, you were with Ticketmaster for some time.

I was looking at your profile.

Yeah.

Um, so that was a really, you know, and I, I think that's

always an interesting contrast.

How, how many years were you there for at that point?

Um,

after acquisition, I wanna say like four, four or five years.

Yeah.

And, and you know, Ryan, I think it's interesting because, um, you know, I

really enjoyed my time at Ticketmaster and I probably would've been, I

probably would've left like just after the Earnout, um, you know, and

then started something a lot sooner.

Except what I was able to do is I was able to carve out, like, I was able

to acknowledge that, yes, I also like you, I thrive in environments where I'm

able to be creative and I can direct that energy towards like, building

and, and let the results speak for themselves rather than persuasion.

And like, I'd rather be in the editor.

Like, I'd rather, I'd rather be in Vim than in like, making a deck, you know?

And I was able to find a home within the, like a huge company that was, um,

You know, a couple of roles that were more like IC roles, but still like,

um, quite senior and influential.

So I was able to do things like just help like prove out like architectural

directions for the company.

Um, you know, whether it was like in blockchain or other like realtime

offline sync type use cases and wrote a patent and stuff like that.

Um, but also just like helping build developer culture speed things up.

Um, sometimes I'd jump in, I would whip up a microservice, like we had a need.

I, like, I wrote the OAuth service for Ticketmaster.

Like there was no OAuth service and that was a capability that if it existed,

unlocked a whole ton of use cases.

So yeah, it's like, rather than making decks about why you might want to create

an OAuth service and embrace open source practices within the org, it's like,

here is the repo, I've deployed it, try it, and then it like caught on.

Right?

So that's kind of my approach and yeah, I think because that company.

I was, I was lucky enough to have been acquired by a company that nurtured

that and also like, you know, yeah.

The shout out, the leaders there.

Like they, they, it was the people there, that leadership team that

nurtured that within the startup company.

They wanted to protect that, like, you know, protect the startup energy of

the, of the folks that they acquired.

I have friends that have sold their companies to, um, similarly

sized, you know, 10, 20 billion, um, you know, acquirers.

Right?

And they end up, they, they acquire, but then the, the merger aspect of it,

like snuffs out all innovation and all.

Mm-hmm.

Like the, the, the soul that drives founders and entrepreneurial and creative,

um, folks to make something zero to one.

Like they just get it totally just gets drowned out by bureaucracy and process.

And then guess what?

Then those people get beaten down.

Their ideas aren't embraced or fertilized, and then yeah, they churn.

Right?

And other folks, you know, who, who maybe thrive in that

environment take their place.

But it's just sad because you acquire like a smart company with tech.

And brilliant founders and leaders and self-starters who can work

autonomously, and you have to give them like the right, you know, ingredients

and the right environment to thrive as part of that merger process.

Otherwise you are not actuating a lot of that value.

So yeah, I stuck around because they, they, it was like a, a wonderful

place for me to like apply my ideas and, and then that, that's why I

chose to, to continue to grow there.

I think you're the first musician I've ever heard say

anything nice about Ticketmaster.

What, what, um, what would you say, you know, so, uh, as far as

Adam, you, you had a repeat co-founder, which I think is an interesting, um,

it probably de-risk a lot of your, um, you know, going into a second venture.

Uh, you probably felt very comfortable, you know, that's one of the biggest

challenges I've heard is finding a good co-founder that you can mesh well with.

Um, w was that, was that similar with, with your situation?

Ryan?

Did.

Did you work with your current co-founder previously or how

did you link up with with

No, actually I was, that is a part of your story, Adam,

that I was going to comment on.

Cause I, my experience I is very different from yours.

Not that, not that I had a terrible time with my first co-founder.

He's actually one of my best friends.

And we learned a lot about each other and a lot about working

together throughout the process.

But I think what we both realized at the end is being great friends

doesn't translate to being great.

Co-founders for a ton of reasons.

Um, it, it, and I, I think I'm in a, in a much better place with my

co-founder relationship that I have now.

And, and it doesn't have anything to do with the fact that she was not previously

my friend, but it, it's just the way that we compliment each other, the way

that we, you know, work together, the way we make decisions, the way we, it just,

it's completely perfect for our situation and the company that we're building.

And honestly, I, I honestly think it was luck.

Like we, we met each other under very kind of random and serendipitous circumstances.

I was, when I left Palantir, I, I, I started another company

and ended up shutting that company down after about a year.

I won't get into that whole story at the moment, but I was

kind of in, in flux, like I was trying to figure out what to do.

Also, the pandemic was raging.

It was lockdown.

There was like, Kind of nothing to do.

I was doing a little bit of contracting, but I was really just trying to figure

out what, what do I want to work on?

And I read this book called Let My People Go Surfing by the founder of

Patagonia, which actually doesn't have anything to do with surfing.

It has to do with the company culture of Patagonia, the story of founding

the company and ultimately about the climate impact of the fashion industry

and the sort of the, the sort of behavioral problem that the world has

about buying new things, not using them enough and throwing them away, putting

them into landfill or storing them in your basement or whatever it is you do

with them when you're done with them.

And how are we gonna, you know, this existential crisis we're facing.

And I was thinking, my mind was racing about all this stuff when I met Emily,

who had just spent two years in her MBA program at Stanford exploring the.

Fashion resale because she cared about the climate impact of the apparel industry.

Like, so, like this is the rant.

Wow.

We met each other and she told me this and I was like, I just read this book.

This is so weird.

We started talking and it was just very clear immediately that we had a chemistry

mutual respect, like, and, and that we could go build something together.

So like, I think you can find your co-founder anywhere.

Mm-hmm.

I do think the relationship is critically important.

It's very easy to get wrong, and the, the way you compliment each other

is, is a huge, huge part of that.

Adam, you had an interesting, uh, I, I thought it

was interesting how your co-founder, how you two first met you.

You just messaged you on LinkedIn or something, right?

Yeah, exactly.

Which is so odd because especially, um, like, you know,

when Craig and I met Right.

Um, I had not founded a company yet.

I mean, not formally.

I had, maybe I had, but the, the stuff that, like Universe was our first

serious company where we raised money and it was a big deal, so, But yeah,

but I was a developer and you know, he messaged me and as a developer, you

know, you get tons of inbound spam from recruiters and like, damn recruiters.

Yeah.

Like as soon as, yeah, as soon as email gets on, like, uh, you know, like a,

like a, like a GitHub or something.

Like I was getting, I was just getting a lot of like unsolicited, um, like blowing

up phones and emails and this and that.

Um, but I got a message on LinkedIn from, from Ben and Craig had a third

co-founder then as well, uh, Ben.

So, yeah, I, I got a message from, from them and something about it just, it

was just a very, like, it, the, the authenticity and like the genuine tone

and the humanity sort of behind the email.

Like it resonated with me and it didn't, it didn't seem like, it felt like, like

this is a, this is a, like the smart, there's a smart guy behind this email.

Mm-hmm.

And I'm curious to know, like, The way that it's just, it just, it hit different.

So yeah, we, we got together, um, you know, we're jamming

on some ideas that they had.

And I had, and I had already started on this sort of like food delivery,

um, sort of Uber X for food type idea.

And I was jamming on that.

I had some rails code written and very basic design.

You know, it wasn't, probably wasn't gonna go anywhere, but I actually

had high conviction on the idea.

And when I met my co-founders, they were already sort of thinking like, on a bigger

scale, very similar, but, um, not just about food, but about many more things.

And I thought, Hey, you know what?

Like I'm probably not gonna make it if I just go at this alone,

let alone when it comes to all the fundraising and all the amazing

things that they had in their network.

And so, yeah, you know, fast forward and that was the right call because

yes, the co-founder, um, skills and um, attitudes and everything

were all very, very compatible and.

We wouldn't available to do it without each other.

And it, it worked out.

And yeah.

Craig and I are now on our second venture.

Craig and I have a wonderful sort of, we like to think of it like a yin and yang

where, you know, he, he actually did go to, um, school for software engineering

and he had like a dual major software engineering and went to a, a prestigious

business school in, in Ontario.

And, you know, I went through computer science, but I, I had

been noodling on like ventures and lemonade stands my whole life, right.

And just have that sort of like, entrepreneurial, um, you know, influence.

I, I think from my, my parents and my family.

So, you know, the yin yang, it's like, you know, you've got, um, primarily

like a developer with a business sense and you have primarily like,

you know, a business and networks and fundraising guy with like Yeah.

The empathy of a former software engineer.

So, you know, we could, you know, he could.

Shoulder surf my SQL query and try and pick out a bug and I could shoulder

surf his Excel financial model and I'd pick out a bug and you know, and

then we'd go and eat food together and all these things and like hang out.

And so yeah, like I think having that compatibility both from the, the, the

hard skills, the technical skills, but also just like, you know, he was in

my wedding party when I got married and had a lot of good times over the

years, like countless good times.

So it's his birthday tomorrow.

Um, yeah.

And so, you know, just having that like affinity for each other and he's

like a brother, so, um, he's, he's a special co-founder to me and yeah,

like feel like with that, you know, we could pivot the business like 180

into something totally random and we would find a way to make it work.

Cool.

Yeah.

You mentioned, uh, that was something that maybe your parents were also,

you know, a little entrepreneurial.

Um, Ryan, is that similar in your, you know, family, uh, as well?

My mom is a, an entrepreneur.

She started her own software company, um, writing wow software

for foundations to manage grants.

So charity, like, you know, the Packard Foundation, so the Packard, Hewlett

Packard family has a bunch of money.

They're giving it away.

They need software to manage all that.

Uh, and she wrote that software.

So I kind of grew up around, um, you know, at least my mom.

My dad worked in tech, but not as an entrepreneur.

But like, just seeing that, that's a thing that probably has a lot to do with sort

of the confidence I, I felt to do it.

I, I feel like.

People often think of ENT at entrepreneurs as like risk takers.

Mm-hmm.

Or, you know, highly risk tolerant people.

And I, and I, I remember reflecting on this even back in 2013 when I was

leaving my job, first time I'm leaving a full-time job to go start a company.

And I don't remember it feeling like a risk to me.

I, I remember actually thinking I, this feel doesn't feel risky at all.

Like, this feels very on rails and it feels like the best way

for me to move my career forward.

And, and so I, I think it probably was trained because my family

was fine, my mom was great.

You know, and like, I think that that must have had something to do

with it, even if it wasn't conscious.

Yeah.

I always think it's an interesting, um, You know, when, when we look to higher

up folks that will adapt well into our environment and we're, you know, 8,

17, 18 folks, I, I tend to look into folks that, you know, that, that are

comfortable with a little bit of chaos.

That, that may they, maybe they've been exposed to it from their parents

at one point, kind of running, you know, a small business, uh, um, or just

being entrepreneurial, uh, mindset.

You know, that's something that I think does translate down.

Um, for me, it wasn't really, I didn't really have parents

that were entrepreneurs, um, but I instead found a, a mentor.

That I, I came into contact with Fresh Outta school who his, you know, he had

been living kind of this entrepreneurial lifestyle, like traveling in Southeast

Asia, recruiting nurses and from Asia and bring 'em into the states.

And so he had been doing this on his own for about a year.

So he was in a very different mindset.

Then we met up in a, in a kind of a corporate-y environment, became really

close, both kind of realized we were really good at, at, at our, at our

job, and he kept putting a bug in my ear of like, man, we could just do

this on our own and subcontract to the company that we're working with.

Why don't we go set something up out, and.

Poly Indonesia.

So his big, his big, um, uh, what he'd always preach is, you know, just,

just get outta your comfort zone.

Uh, cuz it's very easy to get comfortable in a corporate gig and,

um, you know, there's nothing wrong with it, but you know, if, if you feel

like you're capable of something more, it's gonna feel uncomfortable, uh, at

first and then the more you can get comfortable with being uncomfortable.

That was kind of our theme.

Um, and so we did, we, we, we split off and spent two years, but we

kind of were able to tee up like a contract with our current employer.

To de-risk it and say, okay, give us, you know, six months of

of work, we'll go stand it up.

And then, um, you know, we kind of knew that we were getting

some sort of an hourly rate, you know, for the foreseeable future.

But, um, you know, we did it for a couple of years.

This was during the housing crisis, um, so it was near impossible to do business

development from across the, the globe.

Um, so after two years, I came home and took a corporate job.

And something that you, you kind of touched on, Ryan, was, I don't know,

I, you know, that transition for me was really, Uncomfortable, but in a bad way.

Like I, I just felt like I had experienced so much that I was

limiting myself to be in a cubicle and, uh, just didn't really see where

my work was, what it was producing.

And so after about a year and a half, I, I, I quit and, you know, traveled

for six months, cleared my head, and then came home and started this

business and, um, never looked back.

You know, it's just been a, an ongoing kind of pursuit since then.

And, and very stressful at times, which is one of the, one of the things I

wanted to kind of bring up to you all is because, you know, you know, risk is,

is is something that you mentioned, but, you know, what is it that you think are

these characteristics that, you know, some people mention grit, persistence.

What is it that you think is, is, is what it kind of takes or what's

gotten you through some of those?

You know, real lows of, of being an entrepreneur.

Yeah.

I mean, Adam, I'm sure you have thoughts here.

I, I never really thought of myself as like super high pain,

tolerance, grit kind of person.

I mean, at least I'm not with physical pain and I, you know, I,

I, I definitely, uh, don't love extremely high stress situations.

I do tend to thrive in them, but I'm not sure that that's necessarily related.

I think it comes back to some of the stuff we talked about earlier.

I, I feel like it's the, it's the creativity that's like innate in a lot

of founders, and it's the like desire to stay close to that creativity and keep

making things and solving problems on a organizational wide level that like, at

least that's what keeps me there in that place and keeps me coming back because I.

Yeah.

It, it's just, there's something about the, the dynamic nature of it.

You know, it's like, it's always, it's always something new.

Mm-hmm.

I, I have a friend who, who described startups or founding a startup to me

as you're inner room, the room is, has a pipe coming outta the ceiling.

That pipe is literally pumping shit into the room, like a

lot of shit into the room.

And your job is to clean it, clean the room of the shit, and you have a symbol.

And so the, and like this visual, like, I just feel like there are obviously

times when things are going well and it's fine and it's whatever, but,

but there are times when I really can like viscerally feel like I'm in

that room with that thimble and it's just coming at you from all angles.

And I think it's the satisfaction of getting through those moments

and looking back at them and being like, holy shit, we.

Navigated that like we navigated that it was not a thing that, like

before this whole thing started, I could even confidently tell you

that I would ever be able to do, but we did it and we figured it out.

Um, I think that's such just like such a good and addicting feeling that mm-hmm.

You just

stick with it.

I just had a very similar conversation with, uh, one of my colleagues about that.

Like, when you look back, like when I look over back over my career, the, the moments

that stand out were those hard times.

And I know at the time I thought it sucked, but in retrospect, my

brain has washed all of the suck out of that like whitewashed at all.

I have no real, like, all I remember is we got through it and it was

a lot of fun and, and good times.

And, and it also that that analogy of like the thimble and clearing out

around the shit works so well for, because when I think about like what

makes for a good co-founder, getting back a little bit to the co-founder

discussion is what I've seen are the people who can still manage to.

Have, enjoy those hard times together.

Like, like you're looking for someone who, it doesn't matter how tough it

is, like it, you could be cleaning out a sewer system or pumping out a

a, whatever, and you'll still manage to make it fun and laugh about it

and just sort of in the moment.

And it's not just like someone who's there whining, complaining, and just sapping all

of your energy about how much this sucks.

It's someone who somehow manages to, like the two of you, it's just a chemistry

thing and you just sort of mm-hmm.

Both lift each other up and like it's, or the three of you or whatever that is.

Um, so I think that that analogy works so well because that's what

you want in a co-founder, someone who's gonna be like, Hey, I'll

take the thimble for a little bit.

Yeah.

It's almost like you, you, you have those moments where you

sit there and you're like, it is actually insane how bad this is.

Right.

Like, you're, you're like almost able to like soberly exchange that moment

with each other and that is so critical.

Yeah.

Yeah.

Yeah.

I, I think for, um, yeah, I think for me, like maybe my trait here

that allows it to work for me is that like, I'm really bad at quitting.

I'm not a good quitter.

Um, which is a blessing and a curse because I think it's a blessing.

Like, you know, you, you gotta, you gotta like it.

If you're one who is quick to quit things, then yeah, you'll look at the

thimble and you'll look at the pipe and you won't even go in the room.

Or maybe you'll, you know, you'll like, you know, put

that thimble to work for a bit.

But then eventually you'll quickly realize that, yeah, this is like,

or horrible, what am I doing?

And you'll move on.

Right?

Whereas I will just like find it some in myself to just keep going.

Uh, and, and actually I, I've sort of like noticed this in general, like,

I don't know when, you know, I, I, if I'm like trading whatever crypto, or

I don't, I, I don't set a stop loss.

I'll buy something and I'll just hold it to zero.

So like, if it, if, if it works out or if it doesn't work, I'll be at

the finish line, whether, whether I'm winning or losing, but I won't,

I won't abandon halfway through.

So I think like, because I have maybe a thick skin for that, or a thin skin for

quitting, however you wanna look at it.

Um, I think in the startup world as a founder, I think maybe that is like,

maybe a superpower of sorts, because there are times when it does seem like

the reasonable thing to do is to move on and you have to push through that and in

order to defy the odds, like, you know, maybe, and then just keep trying and

just keep innovating and, and, and going.

And then, yeah, like then you stumbled upon the thing that.

Gets you product market fit or gets you through that fundraiser or gets you

through whatever your next hurdle is.

And then, well, I mean, you were talking about skiing before, right?

You know, when you're on like the rope, you're waiting for the rope toe, right?

And like, they always have those like duct tape knots or something,

like on the, on the rope.

And so you, the rope is going through your gloves, you're not getting any traction,

and you're waiting, waiting, waiting.

And all of a sudden, like your glove grabs that knot and just yanks

you up the, up the thing, right?

Mm-hmm.

And the next thing you know, you're at the top, but you've gotta like,

you've gotta wait, you know, wait, you gotta hold that rope and just wait

until you actually like, you know, you get that purchase and then it'll

send you up the, up the hill, right?

And then that's good for me.

I think also though, at the same time, the thing, the, the phase of all of it

that I like the least, the thing that, like, I don't quit, but, but I'm also, I'm

buckling under the pressure of like not having, um, either a user, like, so being

in stealth is very like anxious period for me because I need the validation of seeing

people use the thing I built to know that.

Well it, to make it as good as it can be, but also to know that what I've

built is not like, you know, insane.

Like I'm not just building something for no one, you know, I, I need to perform,

like, I need to have an audience.

I think I do my best work with an audience.

And so operating in stealth, like I'm realizing that minimizing the

period when I'm in stealth is pro.

It's probably best for me, like my mental health, but also just like

my, my performance And, um, yeah.

And so, and then also like being pre, like being live, but not having product market

fit, being like, you know, pre-revenue I think is also like another anxious period.

Cuz then, then once you have users, it's, it's like, okay,

well, but, but they're not paying.

How do I get them to pay now?

And then that becomes like, the next thing that I wanna unlock.

Mm-hmm.

And I think once, once you know, I'm getting a dollar 10 or a thousand or

whatever the, like once there's some trickle of water through the pipes, then

I'm like, okay, now, now this becomes more of a scaling exercise and like that

is more comfortable, but then the rest of it, That I, I think I take it, it

can be like, I, I beat myself up a lot.

Like if I ever say unkind things to myself, it's when we're in stealth or

when we don't have like a dollar trickling through the system yet, that's when

I'm maybe like the hardest on myself.

And then I think that's maybe when the, yeah, when, if I was just more chill about

that phase, I'd probably enjoy it more.

Mm-hmm.

But it'd be, I, I, I make it more stressful than it needs to be because

I think it's just that's, that's just in my nature for some reason.

Interesting.

Yeah.

I wanted to, um, there was something while we're talking about risk and um,

something I think, Adam, you said way or early on about sort of insulating

people and, and one of the things that I think is interesting for startups is

like as you start hiring people and you have more people there, obviously people.

Join startups, they're probably a little more, um, risk taking or whatever.

That's sort of this notion.

I'm curious how you balance how much you insulate and create that like sa

that that zone of safety for people versus how transparent you are.

Because to me, I'm all about transparency.

I came to a startup, I know the risks.

I know that like, if we're not making money, like things can happen and,

and like just share it with me and I, I'll handle it much better than you

trying to insulate me from it too much.

And then it's a big surprise.

So I'm curious, like, as a, as a founder, how do you balance that?

And Ryan, I'm also curious for your opinion about starting with Adam.

Like how do you sort of balance that transparency versus insulation?

Yeah, I think, uh, yeah, that's a, it's a really interesting,

um, sort of spectrum, right?

Like, do you want to be radically transparent or do you want to.

Maybe curate that, that impression a little more.

And I think lately I am leaning more towards the more transparent

part, but we still, yeah, like there, there is a lot of, there are

some, how do I, how do I say that?

I mean, it takes like maybe a certain amount of intestinal fortitude to

like acknowledge and deal with, with those certain realities.

And so, you know, when I was a developer and I didn't have to think about

those things, like I was a developer in the 2008 financial crisis, right?

I wasn't a founder then.

And you know, the founders would communicate that yes, the

company is in like, like healthy balance sheet, don't worry.

But it's also like, uh, there's volatility out there and like, we don't know exactly.

So like we we're okay, but the macro is not.

So we gotta be mindful.

But at the same time, don't be skittish like your, your job is secure, but.

We all need to be resourceful.

And so there's kind of like, you know, they could have, they could have said

things that were scary and I probably, I might have freaked out and who knows,

maybe I would've sought out a, like, maybe a bigger company than a startup thinking

I don't want to miss, you know, like rent.

I mean, I,

I was gonna say this, the same thing effectively, is that I

don't think that there's a cut and dry way to say what's right here.

Uh, I think it's about using your best judgment as a leader.

It's, they're like, take a fundraising cycle.

You can go through, you know, a lot of rollercoaster emotions of like, you

had a bad meeting and it really like crushed you and you know, and you're

not sure what's gonna happen next.

And then you have a really great meeting and that brings you back up and

that like very tight feedback loop of emotions is not helpful information to

be giving to like the rest of the team.

Right.

And so I think in any given situation, you just need to like, Does the, does the

cost outweigh the benefits, uh, you know, of bringing people along for, for this?

And, and I feel like my co-founder, Emily and I, are making micro decisions

on this level about transparency daily.

Mm-hmm.

You know, like, and, and just every little thing we discuss and talk about,

and we actually do have a, like you said, Adam, we have a general policy

of transparency and openness with our team, but we also, it depends, is the

shortest, shortest way to say that.

Tim, I've got one, I've got one thing to jump back to before we, before we wrap

on something, Adam said, just cuz I've, I feel pretty strongly about this area.

So Adam was talking about the.

Uh, no, like the, the thin skin for quitting, right?

Like ta taking it down to the ground, like literally crashing

the plane into, into the earth.

Um, and I think I, I, I think on, on the surface, I completely agree with you.

Like I, I was in by Combinator for Paul Graham's last batch, and one thing

he said to us really stuck with me, which is like, the thing that separates

successful companies from unsuccessful companies is the founders of the

successful companies did not quit.

There's literally nothing else that separates them.

And that really stuck with me, and I actually believe it.

I think you could actually just keep doing a thing for long enough, no matter what

it is to figure it out and be successful.

But the, the other thing you said about mental health, and I think this is

particularly clear to us as multi-time founders, is that there are versions

of that story that are terrible for you and terrible objectively.

And there are versions of that story that are not terrible.

Mm-hmm.

They, they're better aligned with what you care about or they're better

aligned with who you're working with.

And so I think in those situations, even if you could go and succeed by toughing

it out, like I believe that there's the next one, um, that, that you can't.

And so it's okay.

It's okay to quit.

Um, that's, that's just my perspective, obviously.

I actually

very much agree with that.

I, I, as Adam's talking, I think.

Yeah.

Um, it was interesting.

Um, I know we wanna move on, but, um, I.

I thought it was great the way you put it, Adam, of for better or for worse,

or for, you know, whatever, because, uh, growing up, blessing and a curse.

Yeah, yeah.

Blessing and a curse, right?

Because growing up cool hand, Luke was my role model, which I don't know

if you know that movie, but it's just about a guy who just does not quit.

Um, spoiler.

It doesn't end well for him.

So, um, and so, um, it's something that like, has been throughout

my career of like, and I, and as I got older, I was like, I've

gotten much better at recognizing like this is a toxic environment.

Like, why, like even if I stuck it out, what am I winning?

Like, all I'm, all I'm winning is, you know, like paying my therapist

more so, you know, or whatever it is.

And so I do agree, like there is that like grit, that like

fortitude that I, I will not quit.

But I think, um, balancing it out and making sure, you know, it's a

healthy environment or, or whatever it is, is, is an important part.

Um, there's definitely some, some situations I stayed in way longer than

I should have, uh, earlier in my career.

Right.

That's a follow up episode I think.

Yeah.

Yep.

I think what it comes down to as well is like having that level of awareness.

Like if you don't have, if you don't have that level of awareness

of when to quit, then you're just gonna keep running on that hamster

wheel thinking that you can, you can fix it and it'll just burn you out.

And no, nobody will benefit from having founders that are just burn out

and can't be, uh, effective leaders.

So.

Um, yeah, I mean, we could riff on this for, for another hour.

I, um, and this is probably one of the longest going that we've

had, but it, that's a good sign.

I mean, I think people are just, you know, we're, we're enjoying the, the discussion,

but I do wanna make the, the, the pivot.

Uh, we'll, we'll close here with this, uh, this, this final segment here

called the the Five Second Scramble.

Um, I'm gonna ask each of you just a, a series of questions.

Try to keep it, you know, within five seconds if you can.

Um, you know, you won't get, you won't get this, uh, uh, if you go over five seconds,

so don't worry about the, the air horn.

Um, I'm gonna go ahead and start with Ryan.

Um, explain archive to me as if I was a

five-year-old.

You can buy used things online from any brand that, well, I don't know if

five-year-olds know what brands are, but what's a five-year old brand?

Some toy.

Okay.

Legos, Lego, you can go by Legos that other kids used to play

with and it's a lot cheaper.

That's good.

Um, how would you describe your culture?

Um, really fun and weird and everyone's super smart

and really respects each other and that's really hard to do, uh, remote.

And I think getting in person as a group at least twice a

year helps immensely with that.

What kind of technologist thrives at archive?

Uh, a product like a product forward engineer or a product tech.

We actually have a very small product team.

We have one product manager for 13 engineers.

Wow.

And it's because every one of our engineers is a product thinker and really

thinks about what am I building and why.

I think that's what draws them to the startup in the first place.

But definitely that.

What

can folks be most excited about for archive in 2023?

Um, we have some really exciting big kind of enterprise

grade brand launches coming up.

I can't mention the brand names, but that's gonna be really exciting

cuz there will be lots of products you'll be able to buy used online

that you won't, that you can't really today, uh, directly from the brand.

So they're refurbished and everything, so that's pretty exciting.

Um, and we will be launching, uh, in-store, uh, pro, uh, kind

of capability so that brands can actually sell these products in

their stores as well as online.

So.

Cool.

Yeah.

Cool.

What's, uh, what's one of your favorite books

or, or podcasts on leadership?

So, I listen to how I built this, like religiously, I've listened to

probably over a hundred episodes of that.

Um, I, I find that the stories are super inspirational and.

I really like listening to ones about like, very far from my domain.

So like not software.

Yeah.

Um, uh, just cuz it just, they're, they're such interesting stories.

My favorite episode is the Tate's Bake Shop episode.

If for anyone who also listens to that, uh,

huge fan and, and, and you can't, you know,

you can't, uh, not mention it.

A guy Ross's voice like a guy Rise.

I know.

Yeah.

There was another one, I think it was like, uh, pita chips Were

yous pita chips or something.

Oh, yeah.

Yeah.

I, I agree.

I, I, I fall into that like very outside of like what I'm doing,

but it's very interesting stories.

Totally.

Um, what do you love most about yourself?

Whoa.

Um, I don't know.

I think I actually, I got, actually got asked this recently

and I would, I would say my creativity, like I am not an artist.

I, I used to play drums so I can sort of consider myself a musician.

Um, I get my creativity out through, often through code and

through the products that I build.

But I really like to think of myself and I think I am a, a really

creative person and I like that.

If you were in a food eating contest, what kind

of food would you be eating?

Um, God, I mean, I would probably choose some form of burger

just cause I feel like I could just keep, or, or like french fries.

I could eat those forever, but those are probably aren't good choices.

That's ok.

It's probably something that's like more optimizes how much you could eat

without getting sick and that is not it.

So

yeah.

Cheeseburger, sliders do sound good though.

Yeah.

Um.

What's the worst fashion trend you've ever followed?

Whoa.

That is a tough one.

I don't know.

I feel like there was a bunch of stuff that went down in the nineties.

Maybe tie dye or mm-hmm.

Slap bracelets, if you consider that a fashion

trend for sure.

Uh, what's a charity or corporate philanthropy that's near and dear to you?

Um,

that's a good question.

I mean, I, I, I always tend to do climate related things.

Um, I don't have a particular one in mind, but that's sort of the problem space

that's most near and dear to my heart.

And so, you know, obviously I choose to spend my time working

on archive for that reason.

But often charities that, like my Amazon Smile is something along those lines.

Nice and we'll, and with, uh, who is your favorite superhero?

I don't really like superheroes.

Um, favorite

dis

favorite Disney Character Nemo.

Oh, nice.

I'll go

Nemo.

Yeah, that's a good answer.

That is a great answer.

Talk about persistent.

Um, all right, that's good.

Uh, that is a wrap on, on your end.

So, uh, Adam, you're up.

You, you ready?

We'll, we'll, we'll be gentle.

Um, okay.

Explain Peggy to me as if I was a five-year-old.

Yeah.

So, um, Peggy is a place where you can meet, uh, other artists like yourself

and you can, uh, purchase their art.

And if you grow up and you no longer like unicorns and you prefer robots,

you can then rehome that painting to someone who loves unicorns and

buy two, uh, paintings of robots.

Perfect.

What's your favorite part about the, the culture at Peggy?

Um, my favorite part about the culture at Peggy is the

intersection between art and technology.

And people who thrive here are ones who have always wanted to work, you know,

in art in some capacity while bridging their love for tech and business.

Um, and so for those folks, this is like the dream job.

What kind of technologist thrives at Peggy?

A technologist who leans into challenging and, um, you know,

undefined problems because we try and give folks autonomy to come up with the

best, you know, may the best solution win.

And, and so folks who, who, who thrive on that and who take great pride in,

you know, the craftsmanship of software, um, generally have a good time here.

And then what

can, uh, folks be excited about, uh, for Peggy in 2023?

We are.

We are currently uploading a ton of really cool artwork.

And so, you know, sure I'm the founder, but as a user, every time I go into

the app and I'm refreshing the home screen, I'm just seeing new, new stuff

and it's just getting better and better.

Lots of more diverse art in terms of just different styles and subject

matters, but lots of really cool things.

So, um, even for me as a founder, it's always a delight to open

the app and see what's new.

Uh, what

is your favorite cereal

Raisin brand?

It it's sort of, yeah.

Is that, is that like a more technical functional cereal?

I mean, it's like, you know, the, the brand is pretty, you know,

the functional, but the raisins give you that hit of sweetness.

So, but the only thing is, um, never buy your Raisin brand from

Costco because I think they use, um, inferior quality flakes.

They're always crushed, so, you know, Avoid, avoid the Costco, uh, quantity,

uh, and, and just get the nice wholesome unbroken flakes that makes all the

difference in your daily ritual.

This episode's brought to us by Costco.

I think we're getting that.

Yeah.

Costco's a big sponsor

here.

Um, that is a pro tip though.

Uh, what, uh, what's a, uh, a big role model in your life?

Um, who or who is a big role model in your life?

Um, I think, you know, not, not a lame answer, but I think my parents,

because, you know, it was my mother that taught me, um, sort of, uh, my soft edge

and, and how to be kind and optimistic.

Uh, and also my father really like, pushed me and challenged me

and sort of taught me the hustle and to have grit and perseverance.

And so I think, um, those two forces have really served me well.

I think as an entrepreneur,

Uh, if you could live in a fictional world from a, a book or

a movie, which, which one would you

choose?

I'm a bit of an anime nerd, and so the Naruto world would be pretty inspiring

because it's got sort of a blend of ninjitsu and magic and technology in

this sort of like, fun, futile era.

So, um, and then, yeah, good times ensue, so I don't think

I would be bored in that world.

And there, there's a lot of like, you know, complimentary skill sets and, and

characters that would keep me entertained.

Nice.

What, uh, do you have a celebrity doppelganger?

When I was a kid, everyone thought that I looked a lot

like the nerdy kid from the sandlot.

And um, maybe that was a form of like mild bullying.

I

mean, every character in the sandlots awesome.

So, yeah.

But anyway, I take that as a

compliment that that one comes to mind as a kid.

And yeah.

But he