May 22, 2024 • 17 mins
In this episode, we talk to Josh Barker, an engineer turned entrepreneur who shares his journey from programming on an Atari in his basement to co-founding a venture studio in Silicon Valley. Josh discusses the importance of building the right thing versus building things right, the value of learning from past failures, and the benefits of starting with low-fidelity solutions. We explore his experiences at KPMG, his unexpected plunge into startup life, and the lessons he’s learned from launching and iterating on multiple tech products.
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Episode Transcript
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(00:00):
Welcome to Tectastic, where we navigate theintersection of technology and business,
uncovering innovations that redefine our world.
Josh, welcome to it's techtastic.
It is lovely to have you here.
Thank you.
Appreciate it.
So you've got an interesting background that Ithink in some ways, you and I have a lot in
(00:22):
common.
So a long time ago, I started adventure studioalso.
Yeah.
We're fractional CFO, CTO, CEO, for a bunch offledgling startups we helped out.
And part of, of course, that is helping themraise money.
We weren't the ones putting money in.
Now that's the big difference.
We were more of an incubator in less yourstudio.
(00:42):
Right?
But, did that in 99 to 2001 after a couple goodreturns on some effort I put in my life, but
then 2001.
Yes.
Then 2001.
Yeah.
And, you know, the rest is history.
Actually, everything we had put money into washistory.
That was the more truth of it.
Right?
Most people.
Yes.
But, I I was also young and dumb and didn'treally know what I was doing, but thought I
(01:06):
did.
So there was not a hubris involved.
But I'm curious about how you got there.
How did you get to the point where creatingadventure studio was what you had to do next?
By accident.
That is totally my response.
By accident.
And I was dumb and young in that same type ofthing.
My background is an engineer.
Started programming on my dad's atari, like,way back in the day, aware that he was just
(01:27):
like, I don't know what my son's doing in thebasement, but, he's doing something.
So I was down there hacking away at stuff andHe thought I'd never leave the basement, but I
did.
Probably can say I did.
But what ended up happening was over thatcareer and that trajectory of engineering, I
found myself at at a point in my career where Iwas at KPMG.
It was a director of innovation there.
And, my buddy called me up out of the blue, andhe was like, Josh, I just went out to
(01:50):
breakfast.
This accredited investor.
He had moved out to Silicon Valley a couple ofyears prior.
And he said, he just wrote me a check for a$150,000 at breakfast.
And I was like, What?
And so he started talking to me, and he waslike, well, can you come out to Silicon Valley
and, like, come and help me do this?
And I was like, well, I know that sounds like atremendous amount of money.
But it's not.
But I will help you figure out how to use thatmoney.
(02:11):
And so, thus, began kind of a little bit of ajourney and started off kind of in a part time,
you know, after 1st moonlighting fashion.
And then quickly, he called me back in a couplemonths later, and he just said, hey.
I've raised over a 1,000,000 in seed funding.
Is that enough?
And I was like, Okay.
Yeah.
I think we can start talking about somerealistic possibilities here.
(02:32):
That that kinda started the journey.
I quit KPMG went out to Silicon Valley withHammer.
And, it was a wild ride.
We were out there for 3 years, and I alwaystell people I was the absolute dumbest person
in the room.
And that's that's the right room to be Right?
You're you know, it's the right room.
So out there, I I tell people too.
I learned the difference between my backgroundbeing an engineer.
(02:54):
You're taught how to build the thing right.
You can pop up in the hood.
You make it run fast, but you're not reallytaught how to build the right thing, which is
like selling the car if you're popping in thehood, making it run So it's like there's a huge
difference and they're two sides of animportant coin.
And if you're not concentrating on that, youget this as an engineer I don't know if you're
background.
You've got some engineering blood.
(03:14):
Yeah.
I started when I was very, very young, and itwas before Atari's.
So you you, yeah, you know that, like, I alwaystell people engineers have this, like, god
combo, you know, where they can, like, createsomething.
Whether or not they should, that's a differentquestion.
They could you can create it.
And so that's dangerous because you you go, Ican create that.
And that's that's part of the entry.
And so, you know, out there, what I learnedwhen I first got out there, we had this vision
(03:38):
And what ended up happening was and we can getinto the details of the store if you're
interested of, like, what we built otherthings, but high level, We took 6 months to
build our first version of a SaaS product andgot it in the hands of users and realized we
built the wrong thing.
And then built another thing, but this time webuilt it in 3 months, and then one and a
Hammer.
And we kept shrinking that time frame to learnwhat the wrong thing is to build.
(04:04):
And we did that over 3 years.
We built, I think, 12 or 13 different apps,wildly different value propositions.
Same trying to trying to solve similarproblems.
Different angles, and we just learned leanstartup.
That's really what it was.
It's like learning lean startup tactics ofmarket validation, market experimentation and
figuring out what to build and how quickly tofind desirability and market desirability and
(04:28):
it was a wild ride.
I've never heard anybody talk about it as howto build things right, but not the right thing.
I've always talked about it as the build itright versus build it right now.
Right?
For me, it was always the mistake we would makeis being careful.
Instead of being like, yes.
Screw careful.
Get it out the door.
Right?
Get in customer hands.
By the way, I've done this for a long time.
(04:49):
Right?
I just made that mistake again.
And it was because our product is trying to dosomething that is kind of one of those, like,
every software engineer wants to scratch thatitch.
Yes.
And it was one of those.
And so we're like, oh, man.
All my engineers are volunteering to work forus, right, because they just wanna scratch that
itch, but it's like, man, we can infinitelyscale this thing up.
(05:10):
We can run it on pennies.
It's super efficient.
All that.
But what does it fix exactly?
Like, what's the m awkward opportunity to hear?
Right.
Right.
Not so much.
Yes.
Close.
Yeah.
Not close enough.
Common mistake.
Yep.
And even, like I said, repeat founders willmake it over and over again, especially if you
have that god complex, wanna build the rightway.
(05:30):
And and if you make the mistake of getting intoa product that is scratching a niche.
Those are the worst because it's a rabbit holeyou go all
the way
to the ground floor.
Right?
Yes.
That Hammer gotta be the, you know, I speak toprobably 5 to 10 founders a week.
And that is probably the most common thing wehear as we go, I have an idea.
(05:50):
I need to go build it.
And then you you ask, what market validation doyou have?
Because that's what an investor wants.
They want Christian, right, is, like, whattraction market traction do you have?
And it's like, Well, none.
I we don't have it because we have to build it.
And you're like, no.
No.
I don't think you understand what we're talkingabout.
So yeah.
Yeah.
Yeah.
And the the funny part for me, though, is I gotinto development because I had ideas, and I
(06:15):
needed to get them out.
And it wasn't so much the technology itself.
It was much for the I've always hadentrepreneurial mindset.
Like, I always, like, there's an opportunity.
I can wrap that up in a bow.
I know I need to build Let's go validate itfirst.
Yes.
Then let's build it, then let's go.
And, this one, though, has been a 30 year baneof my Christian, and so it's one of those ones
(06:36):
is, like, now, fuck.
We know what we have to build.
Let's go build the damn thing.
As I said, it, you know, was one of those boatswhere it's like, yep.
Plastic error, like, all across the board.
Right?
Exactly.
Exactly.
We've all made it, and it's, you know, in mybackground, I've built 13 different failed
startups So I could say the scars are there.
And almost every single time, there is a storyof, like, I remember this one time So the the
(07:02):
space we were trying to solve, the problem wewere trying to solve is 66% of gym memberships
going used, which is to us, is disgusting,right, because his gyms are making profit on
people not using the product that they'recharging for.
So guilt tax for, and the the gym knows they'redoing it.
Yeah.
They know.
And so we were like, we wanna solve this, and Iwill never forget one of the pivots that in our
(07:24):
journey, talking about me building as I Ilearned this lean startup skill, but I still
ended up, you know, so we wanted to gamify it.
And so I was like, you know, what we could dois you create this choose your own adventure
story.
And then, like, you go down this path, and it'sa really elaborate story, and you could choose,
and you have to get to do jumping jacks in theother story.
And then I've created I mean, I wrote 30 pagesof this freaking autobiography.
(07:47):
I feel like of a story that's just huge, and Icould've I could've wrote a page of it and just
tested it and been like, do you want this?
And clearly, within two minutes of userslooking at it, they're like, I don't want this.
I'm I've got my exercise gear on.
I'm ready to go, and now I have to read a book.
What are you talking about?
And so I'm like, oh my gosh.
I did it again.
(08:08):
Know, you you do those things over and over.
So That
and it doesn't matter how painful it was.
You you will make the mistake again.
It's just Yes.
Right?
Hubris, excitement.
Like, the things that make you a goodentrepreneur are also the risks that you face.
Right?
Overly optimistic.
I know the right answer.
I've got my Christian.
(08:28):
Right?
All great things.
What's what's so funny is I don't know if youexperienced this too because you said you had a
a stint at doing your own venture studio iswith my own ideas, those are the ones that I
have the rose colored glasses on.
Then when I hear other people's ideas, I canpoke every hole and every idea.
Right?
And I'm like, I don't know, man.
(08:50):
If you consider this, this, this, this, this,if you this.
And so but it's with my ideas.
I just get blind.
Yeah.
Oh, absolutely.
Because you've already convinced yourself.
Right?
You don't
You convinced yourself.
Yes.
I'm always the most interested in things thathave proven me wrong, like Wayfair.
I I was at Wayfair.
I've spent a lot of time there.
The founders friends.
(09:11):
In 1994, we wrote a here's how the web willtransform the world.
And we talked about it in five stages.
And the last stage was all things you wouldnever actually buy online.
Live animals, a home, your car, and furniture.
Yeah.
Yeah.
And I was like, nope.
That's bullshit.
There's no possible way that that's working.
(09:31):
And so I had to go there.
I had to learn, like, why did this work?
How did you how did you make a business out ofthis terrible idea?
It's it's those terrible ideas.
Yeah.
You and, like, even, like, someone like Uber.
Right?
I talked to people about Uber or Airbnb.
If you're staying in a freaking stranger'shome, it's like think that, like, if that
didn't exist before, you're like, this is I gotan idea.
(09:53):
I'm gonna stay in a stranger's home in theirspare bedroom, and everyone's like, this I
don't know what you're okay.
Because that's a horrible idea.
Well, yeah, you said Uber, and I was I wasreminded before Uber, there was the car
sharing.
Christian at least that was like a rental car.
It was like, oh, I kinda get it.
Yes.
It's a dumb idea because you've got the fullcapital outlay upfront and, right, and they're
(10:13):
Yes.
It's just silly from the economics of it.
When they started doing Uber, I'm like, I'm notthis is I don't hitch hike.
I'm not getting in some Rando's car.
Right?
But they did catch on to a a market dynamicthat I didn't recognize was there, and that's
the part that they derisked it.
They made it like a taxi that the payment washappening through their they were giving you
rates.
All that kind of stuff, they derisked it foryou.
(10:34):
And I was like, oh, I get it now.
But I I would have poked a thousand holes init.
There's no way I would have invested in it.
No way.
No way.
And there's, you know, if you remember, do youremember, I think it was 2000.
It's a company called Web Van.
Do you remember Web Van?
That's 1,000,000.
So they they were the 1st grocery storedelivery.
Like, they were, like, trying to do delivery.
(10:56):
And so western webbank.
Story will always what's so fascinating is youhave all these Uber Eats.
You've got all these delivery services now thatare super hot, especially post pandemic, you
know, right, and, like, that that was the thepeak.
But, like, in webvan days, they just scaled anddid the wrong playbook too quickly because they
just dumped all this VC money in.
They grabbed all these huge warehouses andyou're like, man, you're just scaling wrong.
(11:19):
But the funny thing is years later, we haveonline grocery Right?
I can go and get my groceries delivered.
So
Well, that's an interesting, point.
And, actually, most of the big changes do comeas the second attempt, not the first.
Yes.
I need to remember that.
I know.
Exactly.
They it's good to remember from the past, allthe mistakes.
You know, I always tell I tell all theirentrepreneurs all the time You know, the first
(11:42):
thing you could do that's super easy that notvery many entrepreneurs do is go and see if
someone's tried this in the past even if itdoesn't exist today.
And literally, we've I I can't tell you thenumber of entrepreneurs.
I've helped reach out to someone who's done itand reached out on LinkedIn and had a
conversation with someone who tried it.
And I was like, that is such an unlock to allof these learnings that you can just be like,
(12:08):
skip way far ahead fast.
Yeah.
Yeah.
That is a tremendously good advice.
And, I will take note of that myself because Iyou know, I tend to look at the failures as a
warning sign rather than as an opportunity.
Yeah.
And they gained a lot of dollars.
They spent a lot of money to get there.
Spent a lot of blood and sweat and tears to getthere.
Wanna show the knowledge, man.
(12:29):
Like, he helped me
out.
Yeah.
Oh, absolutely.
Yeah.
There's so many, and they you know, usually youwhen you get them talking, they they won't stop
talking number 1, which is great.
And number 2 is, like, you'll notice the alwayssay the phrase.
If I could do it all over again, here's what Iwould do.
And then that's when you sharpen your penciland you go, okay.
Tell me.
Since say.
Like, how would you do this over again?
(12:50):
Right?
And you're just really into how you wouldfigure it out today.
I I as I'm sitting here thinking about it,like, I tend to get a little gun shy.
Right?
You you try something.
You're like, wow.
Painful.
Ouch.
I don't wanna get back into that meat grinderand take a big step back and you look for
something else that's shiny.
And we have this is another problementrepreneurs have.
Right?
(13:10):
Where is the next shiny thing?
Where's the best thing you actually could do isto do exactly what you just said to yourself.
What would I do this time if I was to startfrom the ground up and try again?
Yeah.
Because you've already got the scars, man.
Like, go win the battle now.
You
got yourself halfway there.
That's right.
I'm really, really, really into you, and Icurrent entrepreneur especially, like, if
(13:32):
there's a digital idea is too often we discountthe idea of cobbling together.
I call them low fidelity, high manual touch.
Like, too many people go, no.
I need it perfect, especially engineers.
Right?
Yeah.
I can design this.
I can build this, and you're like, no.
Run the whole dad gum thing over tech.
Like, you look at Uber, that's how theystarted.
(13:52):
They started as a texting service.
And so you're like, people are, like, text thisnumber if you need a ride, and people are like,
they did?
And you're like, yeah.
Like, that that's the easiest way.
You don't have to build an app.
Just go and figure out existing mediums.
One of my good friends.
He has a startup in the AI space aroundproperty management, and he and I worked
(14:12):
together at Wayfair, and he just had aspreadsheet.
Yes.
And he got such high confidence from it.
In fact, his initial customers were like, justgive me the spreadsheet.
You solved the problem for me.
Right?
Well, he had no trouble raising money becausehe was able to say, like, look.
All the customers already have, and that wasjust a spreadsheet.
Those are the ones that I get super excitedabout.
(14:33):
Like, the funny thing is as an engineer, and Idon't know how much your audience is technical,
but, like, I won't get technical jargon, but Iwill say engineers tend to scoff at companies
and and brands and things that are like, man,this whole company has run off a spreadsheet I
can't believe, you know, right.
It's like, it's gotta be better technology todo this.
But I look at that now, and I go, that'sbeautiful.
(14:53):
Oh, yeah.
Because you started super simple.
You figured out what you should do.
Now you've got a scale problem, rather than toooften we have an over optimization problem as
an engineer.
Hammer, man, brother, like, that's a big onefor me too.
I I I walked people through, like, do you knowhow many of the biggest deals I've been a part
of that happened, first of all, that happenedover spray sheets.
(15:13):
It wasn't the contracts that were the problem.
It was, like, the details in the numbers andspreadsheets.
Right?
And the biggest companies I've ever been at thevast majority of their operations are in
spreadsheets.
Nice.
You know, Mersk doesn't run off of giant well,they do have giant ERPs and all that, but the
vast majority of the real decisions are handledin spreadsheets.
(15:33):
And that's the reality of the world.
Well, if they can run a $100,000,000,000 a yearcompany with spreadsheets, What are you doing?
That's right.
That's such a good early market signal.
When people are trying to do things in a lowfidelity way, like, one of the one of the
startups we've been working with, theyidentified there was behavior happening in
(15:54):
Facebook Messenger in these groups.
And so they were like, I think there'ssomething here because I'm seeing all these
Facebook groups doing these very specificthings.
They're and this was in the fitness space.
They're releasing these challenges in this veryspecific way.
I bet you if I could get if I could get themusing this app and I could make an app out of
it and sure enough, like, they were able tokind of move a lot of those people over because
(16:15):
they're they found something that people weremanually first.
And they're like, now there's a more automatedway.
They're like, this is awesome.
So yeah.
Josh, man, I've loved this conversation.
Wanna keep it going, but we're out of time.
Alright.
I would love to consider this conversationhaving you on again if you're up for
Yeah.
Happy to do that.
Let's do it.
Awesome.
Josh, thank you so much for being on the show.
(16:37):
Thank you.
Appreciate it.
And that's a wrap for this episode ofTectastic.
Wanna thank you personally for joining us, andwe'll see you next time.
Until then, keep exploring, and stay curious.
Thank you for listening.
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(16:58):
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Welcome to Tectastic, where we navigate theintersection of technology and business,
uncovering innovations that redefine our world.
Josh, welcome to it's techtastic.
It is lovely to have you here.
Thank you.
Appreciate it.
So you've got an interesting background that Ithink in some ways, you and I have a lot in
(00:22):
common.
So a long time ago, I started adventure studioalso.
Yeah.
We're fractional CFO, CTO, CEO, for a bunch offledgling startups we helped out.
And part of, of course, that is helping themraise money.
We weren't the ones putting money in.
Now that's the big difference.
We were more of an incubator in less yourstudio.
(00:42):
Right?
But, did that in 99 to 2001 after a couple goodreturns on some effort I put in my life, but
then 2001.
Yes.
Then 2001.
Yeah.
And, you know, the rest is history.
Actually, everything we had put money into washistory.
That was the more truth of it.
Right?
Most people.
Yes.
But, I I was also young and dumb and didn'treally know what I was doing, but thought I
(01:06):
did.
So there was not a hubris involved.
But I'm curious about how you got there.
How did you get to the point where creatingadventure studio was what you had to do next?
By accident.
That is totally my response.
By accident.
And I was dumb and young in that same type ofthing.
My background is an engineer.
Started programming on my dad's atari, like,way back in the day, aware that he was just
(01:27):
like, I don't know what my son's doing in thebasement, but, he's doing something.
So I was down there hacking away at stuff andHe thought I'd never leave the basement, but I
did.
Probably can say I did.
But what ended up happening was over thatcareer and that trajectory of engineering, I
found myself at at a point in my career where Iwas at KPMG.
It was a director of innovation there.
And, my buddy called me up out of the blue, andhe was like, Josh, I just went out to
(01:50):
breakfast.
This accredited investor.
He had moved out to Silicon Valley a couple ofyears prior.
And he said, he just wrote me a check for a$150,000 at breakfast.
And I was like, What?
And so he started talking to me, and he waslike, well, can you come out to Silicon Valley
and, like, come and help me do this?
And I was like, well, I know that sounds like atremendous amount of money.
But it's not.
But I will help you figure out how to use thatmoney.
(02:11):
And so, thus, began kind of a little bit of ajourney and started off kind of in a part time,
you know, after 1st moonlighting fashion.
And then quickly, he called me back in a couplemonths later, and he just said, hey.
I've raised over a 1,000,000 in seed funding.
Is that enough?
And I was like, Okay.
Yeah.
I think we can start talking about somerealistic possibilities here.
(02:32):
That that kinda started the journey.
I quit KPMG went out to Silicon Valley withHammer.
And, it was a wild ride.
We were out there for 3 years, and I alwaystell people I was the absolute dumbest person
in the room.
And that's that's the right room to be Right?
You're you know, it's the right room.
So out there, I I tell people too.
I learned the difference between my backgroundbeing an engineer.
(02:54):
You're taught how to build the thing right.
You can pop up in the hood.
You make it run fast, but you're not reallytaught how to build the right thing, which is
like selling the car if you're popping in thehood, making it run So it's like there's a huge
difference and they're two sides of animportant coin.
And if you're not concentrating on that, youget this as an engineer I don't know if you're
background.
You've got some engineering blood.
(03:14):
Yeah.
I started when I was very, very young, and itwas before Atari's.
So you you, yeah, you know that, like, I alwaystell people engineers have this, like, god
combo, you know, where they can, like, createsomething.
Whether or not they should, that's a differentquestion.
They could you can create it.
And so that's dangerous because you you go, Ican create that.
And that's that's part of the entry.
And so, you know, out there, what I learnedwhen I first got out there, we had this vision
(03:38):
And what ended up happening was and we can getinto the details of the store if you're
interested of, like, what we built otherthings, but high level, We took 6 months to
build our first version of a SaaS product andgot it in the hands of users and realized we
built the wrong thing.
And then built another thing, but this time webuilt it in 3 months, and then one and a
Hammer.
And we kept shrinking that time frame to learnwhat the wrong thing is to build.
(04:04):
And we did that over 3 years.
We built, I think, 12 or 13 different apps,wildly different value propositions.
Same trying to trying to solve similarproblems.
Different angles, and we just learned leanstartup.
That's really what it was.
It's like learning lean startup tactics ofmarket validation, market experimentation and
figuring out what to build and how quickly tofind desirability and market desirability and
(04:28):
it was a wild ride.
I've never heard anybody talk about it as howto build things right, but not the right thing.
I've always talked about it as the build itright versus build it right now.
Right?
For me, it was always the mistake we would makeis being careful.
Instead of being like, yes.
Screw careful.
Get it out the door.
Right?
Get in customer hands.
By the way, I've done this for a long time.
(04:49):
Right?
I just made that mistake again.
And it was because our product is trying to dosomething that is kind of one of those, like,
every software engineer wants to scratch thatitch.
Yes.
And it was one of those.
And so we're like, oh, man.
All my engineers are volunteering to work forus, right, because they just wanna scratch that
itch, but it's like, man, we can infinitelyscale this thing up.
(05:10):
We can run it on pennies.
It's super efficient.
All that.
But what does it fix exactly?
Like, what's the m awkward opportunity to hear?
Right.
Right.
Not so much.
Yes.
Close.
Yeah.
Not close enough.
Common mistake.
Yep.
And even, like I said, repeat founders willmake it over and over again, especially if you
have that god complex, wanna build the rightway.
(05:30):
And and if you make the mistake of getting intoa product that is scratching a niche.
Those are the worst because it's a rabbit holeyou go all
the way
to the ground floor.
Right?
Yes.
That Hammer gotta be the, you know, I speak toprobably 5 to 10 founders a week.
And that is probably the most common thing wehear as we go, I have an idea.
(05:50):
I need to go build it.
And then you you ask, what market validation doyou have?
Because that's what an investor wants.
They want Christian, right, is, like, whattraction market traction do you have?
And it's like, Well, none.
I we don't have it because we have to build it.
And you're like, no.
No.
I don't think you understand what we're talkingabout.
So yeah.
Yeah.
Yeah.
And the the funny part for me, though, is I gotinto development because I had ideas, and I
(06:15):
needed to get them out.
And it wasn't so much the technology itself.
It was much for the I've always hadentrepreneurial mindset.
Like, I always, like, there's an opportunity.
I can wrap that up in a bow.
I know I need to build Let's go validate itfirst.
Yes.
Then let's build it, then let's go.
And, this one, though, has been a 30 year baneof my Christian, and so it's one of those ones
(06:36):
is, like, now, fuck.
We know what we have to build.
Let's go build the damn thing.
As I said, it, you know, was one of those boatswhere it's like, yep.
Plastic error, like, all across the board.
Right?
Exactly.
Exactly.
We've all made it, and it's, you know, in mybackground, I've built 13 different failed
startups So I could say the scars are there.
And almost every single time, there is a storyof, like, I remember this one time So the the
(07:02):
space we were trying to solve, the problem wewere trying to solve is 66% of gym memberships
going used, which is to us, is disgusting,right, because his gyms are making profit on
people not using the product that they'recharging for.
So guilt tax for, and the the gym knows they'redoing it.
Yeah.
They know.
And so we were like, we wanna solve this, and Iwill never forget one of the pivots that in our
(07:24):
journey, talking about me building as I Ilearned this lean startup skill, but I still
ended up, you know, so we wanted to gamify it.
And so I was like, you know, what we could dois you create this choose your own adventure
story.
And then, like, you go down this path, and it'sa really elaborate story, and you could choose,
and you have to get to do jumping jacks in theother story.
And then I've created I mean, I wrote 30 pagesof this freaking autobiography.
(07:47):
I feel like of a story that's just huge, and Icould've I could've wrote a page of it and just
tested it and been like, do you want this?
And clearly, within two minutes of userslooking at it, they're like, I don't want this.
I'm I've got my exercise gear on.
I'm ready to go, and now I have to read a book.
What are you talking about?
And so I'm like, oh my gosh.
I did it again.
(08:08):
Know, you you do those things over and over.
So That
and it doesn't matter how painful it was.
You you will make the mistake again.
It's just Yes.
Right?
Hubris, excitement.
Like, the things that make you a goodentrepreneur are also the risks that you face.
Right?
Overly optimistic.
I know the right answer.
I've got my Christian.
(08:28):
Right?
All great things.
What's what's so funny is I don't know if youexperienced this too because you said you had a
a stint at doing your own venture studio iswith my own ideas, those are the ones that I
have the rose colored glasses on.
Then when I hear other people's ideas, I canpoke every hole and every idea.
Right?
And I'm like, I don't know, man.
(08:50):
If you consider this, this, this, this, this,if you this.
And so but it's with my ideas.
I just get blind.
Yeah.
Oh, absolutely.
Because you've already convinced yourself.
Right?
You don't
You convinced yourself.
Yes.
I'm always the most interested in things thathave proven me wrong, like Wayfair.
I I was at Wayfair.
I've spent a lot of time there.
The founders friends.
(09:11):
In 1994, we wrote a here's how the web willtransform the world.
And we talked about it in five stages.
And the last stage was all things you wouldnever actually buy online.
Live animals, a home, your car, and furniture.
Yeah.
Yeah.
And I was like, nope.
That's bullshit.
There's no possible way that that's working.
(09:31):
And so I had to go there.
I had to learn, like, why did this work?
How did you how did you make a business out ofthis terrible idea?
It's it's those terrible ideas.
Yeah.
You and, like, even, like, someone like Uber.
Right?
I talked to people about Uber or Airbnb.
If you're staying in a freaking stranger'shome, it's like think that, like, if that
didn't exist before, you're like, this is I gotan idea.
(09:53):
I'm gonna stay in a stranger's home in theirspare bedroom, and everyone's like, this I
don't know what you're okay.
Because that's a horrible idea.
Well, yeah, you said Uber, and I was I wasreminded before Uber, there was the car
sharing.
Christian at least that was like a rental car.
It was like, oh, I kinda get it.
Yes.
It's a dumb idea because you've got the fullcapital outlay upfront and, right, and they're
(10:13):
Yes.
It's just silly from the economics of it.
When they started doing Uber, I'm like, I'm notthis is I don't hitch hike.
I'm not getting in some Rando's car.
Right?
But they did catch on to a a market dynamicthat I didn't recognize was there, and that's
the part that they derisked it.
They made it like a taxi that the payment washappening through their they were giving you
rates.
All that kind of stuff, they derisked it foryou.
(10:34):
And I was like, oh, I get it now.
But I I would have poked a thousand holes init.
There's no way I would have invested in it.
No way.
No way.
And there's, you know, if you remember, do youremember, I think it was 2000.
It's a company called Web Van.
Do you remember Web Van?
That's 1,000,000.
So they they were the 1st grocery storedelivery.
Like, they were, like, trying to do delivery.
(10:56):
And so western webbank.
Story will always what's so fascinating is youhave all these Uber Eats.
You've got all these delivery services now thatare super hot, especially post pandemic, you
know, right, and, like, that that was the thepeak.
But, like, in webvan days, they just scaled anddid the wrong playbook too quickly because they
just dumped all this VC money in.
They grabbed all these huge warehouses andyou're like, man, you're just scaling wrong.
(11:19):
But the funny thing is years later, we haveonline grocery Right?
I can go and get my groceries delivered.
So
Well, that's an interesting, point.
And, actually, most of the big changes do comeas the second attempt, not the first.
Yes.
I need to remember that.
I know.
Exactly.
They it's good to remember from the past, allthe mistakes.
You know, I always tell I tell all theirentrepreneurs all the time You know, the first
(11:42):
thing you could do that's super easy that notvery many entrepreneurs do is go and see if
someone's tried this in the past even if itdoesn't exist today.
And literally, we've I I can't tell you thenumber of entrepreneurs.
I've helped reach out to someone who's done itand reached out on LinkedIn and had a
conversation with someone who tried it.
And I was like, that is such an unlock to allof these learnings that you can just be like,
(12:08):
skip way far ahead fast.
Yeah.
Yeah.
That is a tremendously good advice.
And, I will take note of that myself because Iyou know, I tend to look at the failures as a
warning sign rather than as an opportunity.
Yeah.
And they gained a lot of dollars.
They spent a lot of money to get there.
Spent a lot of blood and sweat and tears to getthere.
Wanna show the knowledge, man.
(12:29):
Like, he helped me
out.
Yeah.
Oh, absolutely.
Yeah.
There's so many, and they you know, usually youwhen you get them talking, they they won't stop
talking number 1, which is great.
And number 2 is, like, you'll notice the alwayssay the phrase.
If I could do it all over again, here's what Iwould do.
And then that's when you sharpen your penciland you go, okay.
Tell me.
Since say.
Like, how would you do this over again?
(12:50):
Right?
And you're just really into how you wouldfigure it out today.
I I as I'm sitting here thinking about it,like, I tend to get a little gun shy.
Right?
You you try something.
You're like, wow.
Painful.
Ouch.
I don't wanna get back into that meat grinderand take a big step back and you look for
something else that's shiny.
And we have this is another problementrepreneurs have.
Right?
(13:10):
Where is the next shiny thing?
Where's the best thing you actually could do isto do exactly what you just said to yourself.
What would I do this time if I was to startfrom the ground up and try again?
Yeah.
Because you've already got the scars, man.
Like, go win the battle now.
You
got yourself halfway there.
That's right.
I'm really, really, really into you, and Icurrent entrepreneur especially, like, if
(13:32):
there's a digital idea is too often we discountthe idea of cobbling together.
I call them low fidelity, high manual touch.
Like, too many people go, no.
I need it perfect, especially engineers.
Right?
Yeah.
I can design this.
I can build this, and you're like, no.
Run the whole dad gum thing over tech.
Like, you look at Uber, that's how theystarted.
(13:52):
They started as a texting service.
And so you're like, people are, like, text thisnumber if you need a ride, and people are like,
they did?
And you're like, yeah.
Like, that that's the easiest way.
You don't have to build an app.
Just go and figure out existing mediums.
One of my good friends.
He has a startup in the AI space aroundproperty management, and he and I worked
(14:12):
together at Wayfair, and he just had aspreadsheet.
Yes.
And he got such high confidence from it.
In fact, his initial customers were like, justgive me the spreadsheet.
You solved the problem for me.
Right?
Well, he had no trouble raising money becausehe was able to say, like, look.
All the customers already have, and that wasjust a spreadsheet.
Those are the ones that I get super excitedabout.
(14:33):
Like, the funny thing is as an engineer, and Idon't know how much your audience is technical,
but, like, I won't get technical jargon, but Iwill say engineers tend to scoff at companies
and and brands and things that are like, man,this whole company has run off a spreadsheet I
can't believe, you know, right.
It's like, it's gotta be better technology todo this.
But I look at that now, and I go, that'sbeautiful.
(14:53):
Oh, yeah.
Because you started super simple.
You figured out what you should do.
Now you've got a scale problem, rather than toooften we have an over optimization problem as
an engineer.
Hammer, man, brother, like, that's a big onefor me too.
I I I walked people through, like, do you knowhow many of the biggest deals I've been a part
of that happened, first of all, that happenedover spray sheets.
(15:13):
It wasn't the contracts that were the problem.
It was, like, the details in the numbers andspreadsheets.
Right?
And the biggest companies I've ever been at thevast majority of their operations are in
spreadsheets.
Nice.
You know, Mersk doesn't run off of giant well,they do have giant ERPs and all that, but the
vast majority of the real decisions are handledin spreadsheets.
(15:33):
And that's the reality of the world.
Well, if they can run a $100,000,000,000 a yearcompany with spreadsheets, What are you doing?
That's right.
That's such a good early market signal.
When people are trying to do things in a lowfidelity way, like, one of the one of the
startups we've been working with, theyidentified there was behavior happening in
(15:54):
Facebook Messenger in these groups.
And so they were like, I think there'ssomething here because I'm seeing all these
Facebook groups doing these very specificthings.
They're and this was in the fitness space.
They're releasing these challenges in this veryspecific way.
I bet you if I could get if I could get themusing this app and I could make an app out of
it and sure enough, like, they were able tokind of move a lot of those people over because
(16:15):
they're they found something that people weremanually first.
And they're like, now there's a more automatedway.
They're like, this is awesome.
So yeah.
Josh, man, I've loved this conversation.
Wanna keep it going, but we're out of time.
Alright.
I would love to consider this conversationhaving you on again if you're up for
Yeah.
Happy to do that.
Let's do it.
Awesome.
Josh, thank you so much for being on the show.
(16:37):
Thank you.
Appreciate it.
And that's a wrap for this episode ofTectastic.
Wanna thank you personally for joining us, andwe'll see you next time.
Until then, keep exploring, and stay curious.
Thank you for listening.
If you are new here and enjoyed the content,please subscribe.
(16:58):
It really helps us out.
And if you are a regular listener, thanks somuch for your continued support.
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