April 29, 2025 • 68 mins
In this episode of Road to CTO, we sit down with Charles Chase, a serial entrepreneur and investor, who shares his journey from aspiring accountant to building multiple successful companies, including Velocify. Charles reveals how a pivotal moment in the late 90s sparked his passion for programming, leading him to abandon his original career path and dive into tech.
Despite mastering coding, Charles chose not to follow the traditional route into CTO roles. Instead, he embraced operational leadership, seeing company-building as a form of engineering. He believes creating systems, processes, and teams requires the same careful design as good software.
Now based in Barcelona, Charles shares his unique perspective on entrepreneurship, emphasizing the psychological qualities needed to succeed. His investment philosophy focuses on the person behind the product, prioritizing vision and problem-solving over the product itself.
🎬 You can watch the video of this episode on the Life on Mars podcast website: https://podcast.marsbased.com/
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Episode Transcript
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Speaker 1 (00:00):
Hello everybody and welcome to Life on Mars.
I'm Alex, ceo and founder ofMarsBased, and in this episode
we bring you Charles Chase, aserial entrepreneur and investor
who created companies likeVelocify, affinity and many
other ventures, and we discusswith him his career as a serial
entrepreneur and how to become atechnical co-founder or a CTO,
(00:21):
even though he has opted not tobe a CTO in many cases, even
though he taught himself how tocode.
He taught himself how to be atechnologist, but he only served
as a CTO in one case in hiscareer.
But we discussed this and moreof that.
We discussed also buildingcompanies, investing, the
differences between the US andBarcelona, and how to be a
(00:43):
newcomer to a startup ecosystem.
So, without further ado, let'sjump right into this episode and
then, you know, you tell meabout your arrival on St Geordie
Day last year.
Speaker 2 (01:02):
Yeah well, first of all, happy St Geordie Day last
year.
Yeah well, first of all, happySt Geordie Day.
If any of my American friendslisten to this, I guess you can
correct me, but my understandingis St Geordie Day is kind of
like Valentine's Day and maybesome other stuff wrapped in one,
and my son, who goes to aCatalan school, is learning the
(01:22):
story of the dragon and how therose came about.
But the cool thing for ourfamily with St Jordi's Day is,
you know, before we decided tomove here, we came and did a.
You know, we had been in Spaina number of times and we knew we
loved it.
But we came to revisit and seethe schools that our kids might
(01:44):
go to.
And that was on St Jordi's Dayand it was not a great day to
fly in because it took about anhour and a half to get here in a
cab, Because if you're inBarcelona on that day, the whole
city is just like it's not anofficial holiday, but it's like
a holiday.
The streets are crazy, Anyway.
So today, waking up and seeingeverybody celebrate, it was
really kind of special for ourfamily.
Speaker 1 (02:06):
Well then, welcome to Barcelona, Welcome to Life on
Mars.
Actually, thank you foragreeing to do this.
I really like your profile.
We met a few months ago, justto give some context to the
audience.
We met a few months ago andyour profile is very interesting
because we oftentimes we get alot of American expats coming
(02:26):
over to Barcelona, right, butrarely ever they are on the
technical side of things.
Usually, you know, retiredinvestors or people more like on
the CEO slash CFO, more like onthe business side of things,
right, or ex-VP at a givenmassive multinational, ex-vp at
Apple, ex-vp at a given massivemultinational, ex-vp at Apple,
ex-vp at Vodafone, or somethinglike that.
(02:49):
But in your case, like well, weshould.
I think Barcelona is in severedemand of more experienced
serial founders that come fromthe technical side of things.
So that's why I wanted tohighlight a little bit your
career, if you're up for it.
So where do we want to start?
Do you want to give some?
Highlight a little bit yourcareer, if you're up for it, so
uh yeah where do we want tostart?
do you want to get?
Speaker 2 (03:07):
I don't know if you remember how we met.
But basically, when I got here,I really wanted to understand
what the technology kind ofstartup ecosystem was.
So I think I googled barcelonastartups and startup grind came
up.
Your name came up.
I think I sent you a cold email, correct, and, and.
So, yeah, you're my friend,you're my first, you're one of
(03:29):
my first friends here and one ofmy and certainly my first kind
of like startup friend, and, and, and, and you've been so
generous and introduced me to somany cool people and and and
and taking me to events, and so,um, yeah, it was just I.
I've spent so many years, um,building things myself and being
(03:50):
around other builders that, um,when I got here, I just wanted
to see, see what was happeningand who was building what, and
um, it has I there's.
There's so many surprises that Iwould never have guessed.
First, of how vibrant thecommunity is here, but also just
the insane amount ofopportunity given so many
(04:12):
factors that we can talk aboutin from investors and how they
look at the market, and I thinkBarcelona and Spain, I in
general is such like a.
It's such a like a underdogmarket, like.
I think if you look at Europe,you know, everybody thinks about
Berlin and the UK.
But there's so much cool stuffand there's so many amazing
(04:33):
founders here, but yet my senseis that they're undervalued.
And so, you know, theentrepreneur or the early stage
investor in me is like oh mygosh, that's an amazing
opportunity for me because youknow I can do things and maybe I
have a competitive advantage.
Speaker 1 (04:53):
You know, so that's cool.
This narrative sort of bringsme to one of the realizations
I've had over the past few years, which is Barcelona has the
potentiality and the capacity tobecome a tier one startup
ecosystem.
Yet I think it's better if wedon't.
(05:15):
Right, why?
Because you know it keepsvaluations down.
It keeps the cost of talentdown as well.
It keeps the cost of talentdown as well.
It brings other founders toinitiate and start up their new
(05:36):
companies here, preciselybecause the cost of starting up
is lower than in other vibrantecosystems.
At the same time, you more orless get everything you would
get from every place else.
Maybe you don't get tier oneelse.
Maybe you don't get tier one,um, I wouldn't say talent, but
maybe infrastructure like youwould get in silicon valley, you
would get in london, you wouldget in tel aviv or berlin and
stuff like that.
But it's a trade-off, right.
At the same time, it's kind oflike where do you want to be?
Like the small?
(05:56):
The small fish in the big pond,the big fish in the small pond,
or you can be like a reallycool fish in the best
motherfucking pond of all time.
Right, and that's where I thinkBarcelona should place itself.
Speaker 2 (06:08):
Yeah, yeah, I mean, the people I've met here are so
motivated and so smart, and I'veonly been here six months, so I
can't imagine where we go fromhere.
Speaker 1 (06:22):
Tell me more about your arrival, because actually
your story sort of resonateswith mine.
When I arrived first in the US,I didn't know anybody, so I
called email people, one ofwhich was people at Startup
Grind, but the other people Imessaged I remember the first
people to respond to one of mycold messages.
I arrived in San Francisco onChristmas Day 2013, and I called
(06:46):
a message from the plane theBarcelona San Francisco
Association, something like thatand a very high-level person
replied to me and first I didn'tholy fuck, I'm meeting this guy
tomorrow and he was like aVSTOPTR VC serial founder, like
(07:08):
chairman of 27 associations,stuff like that.
And so he said I got 30 minutesfor you, miguel Valls.
I'll never forget the name.
He opened me the first doors inSan Francisco, which in turn,
they open more doors.
So that first contact, it'salways very important.
That's why I try to be thatkind of person, even though I'm
not high level, as he was.
But I try to open the doors tosomebody else because you never
(07:32):
know right.
Most of all, I like to be anambassador of my own city.
So, but you took the first step, you called, message a few
people to see what was going on.
So what's the thought processbehind?
Like I'm going to reach out totech leaders in the industry.
Speaker 2 (07:49):
Well, I mean the kind of stepping back the you know
the impetus for us moving toSpain, and so you know I'm
married and we have three, threekids and you know the impetus
for us moving to Spain wasreally about trying to provide
our kids a maybe a broaderviewpoint on the world.
(08:14):
You know we were the kids hadfirst grown up in Los Angeles
and then during COVID, we hadmoved about an hour and a half
south to a really small beachtown called Solana Beach in San
Diego, california.
It's a really idyllic place togrow up and to have kids, but
(08:35):
it's a little insular, right.
If you never left, you wouldnot really understand or have a
very broad perspective in myviewpoint.
So we had come to Spain anumber of times.
My wife's sister is married toa Spaniard, so we've spent a lot
of time here.
(08:55):
So you know there was a window.
You know you need these windowsright.
Like during COVID, there was awindow and that got us to San
Diego.
Like during COVID, there was awindow and that got us to San
Diego, and the window thatbrought us to Spain was my
oldest was about to start hisfreshman year in American high
school, which is this reallykind of seminal, important time
(09:15):
in a young person's life and Iknew that once he started high
school in the US it would behard to kind of get out at high
school in the US.
It would be hard to kind of getout.
But we slowly started thisconversation when he was still
in eighth grade, which is, youknow, kind of the end of primary
school there, and he was allfor it.
My oldest is really adventurousand if he wasn't adventurous
(09:43):
and if he was really set onstaying there, we wouldn't be
here, right?
Because the kids had to buy in.
So you know, we came out hereand when we came out here I
wasn't working on any projects.
I was.
You know, I basically tellpeople I'm on sabbatical.
You know, I can't tell I'm 50,I can't tell people I'm retired.
I can't tell I'm 50.
I can't tell people I'm retired.
(10:06):
And so we got moved in and mywife and I have went out and
were tourists in the city formany, many days.
But then I felt like, okay, Ineed to start meeting some
people.
And so I'm a builder, I want tobuild things, I want to support
other builders, I want to hearabout what people are building.
I just I like I don't know, Ilike geeking out on things
(10:30):
getting built.
You know it's been that way mywhole life, right, like when I
was a kid.
I just love building things andwhether it's software or Legos
or a company, I just it reallyexcites me and so I just wanted
this, I wanted this like hereand see like what are people
building here?
Obviously, I know about some ofthe big companies, like global
(10:51):
and stuff like that, but I'mmuch more interested in like
what's that one person, that oneguy or girl building that
they're really passionate about?
And that was that was theimpetus for for trying to get
into the ecosystem, because Ineed that part for my spirit.
I need to be part of thebuilding of things or hearing
(11:18):
about it, and that reallyfulfills a big part of my
professional life.
That was the impetus for that?
Speaker 1 (11:28):
how do you become a software engineer?
When did you want to start likeprogramming, coding?
Speaker 2 (11:33):
uh, take me back to that, yeah time so I, when I was
in college, um, I studiedeconomics and accounting and I
was really set on becoming anaccountant and a CPA.
I actually graduated college in1996, and I had a job at a big
accounting firm called PriceWaterhouse, and what happened
(11:58):
was I graduated a quarter late,so I was, instead of graduating,
travel around Europe were, youknow, not going to happen.
(12:27):
So my father had a softwarecompany.
Although my father was not asoftware engineer, he was like a
marketing guy and actually areally good product designer,
and so he had been working inthe software business actually
since the 70s, before there waseven really software.
He was doing all this consultingand then they had their first
(12:49):
software was on the mainframes,um, and so in 97, um, his
company was thinking abouttaking their, uh, their their
software, which was like a verykind of traditional client
server where you had, you know,these kind of fat clients
(13:10):
probably getting too technicalhere, but you know you had a
bunch of software installed on aperson's computer that talked
to a server, and mybrother-in-law, who was a CTO at
that time, kind of got thisidea or got this inspiration to
create a web interface, and ifyou think back, this was super,
(13:31):
super, super early.
So they were going to create aweb interface for their product.
They were thinking about doingit in like 96 or 97, which was
really, really, really early,and so I went there to help them
, not in a programming role, butlike in a I don't know, just a
do-anything kind of role, right.
Speaker 1 (13:50):
A webmaster.
We called them webmasters backin the day.
Speaker 2 (13:56):
And I just got interested in the.
I got interested in thebuilding and actually my
brother-in-law who I owe anincredible debt to, basically
one day gave me a book on HTMLand I went home I read this book
on HTML.
I was like okay, cool.
And then he set me up like alittle sandbox and I started
building little HTML pages.
(14:16):
Then he got me a book onJavaScript and I started reading
that, started doing that, andthen I think the thing for me
the big like aha moment was Idon't know if you remember, but
Microsoft used to have this webserver called Internet
Information Server IAS.
Yeah, and they had thistechnology called Active Server
(14:39):
Pages, asp, yep, and with ASPyou could from a web page, make
a call to a database, query thedatabase and then write to the
page a table or whatever right.
I'm getting goosebumps justthinking about it now, because
the first time I saw that happenwhich was probably in like 1997
(15:03):
, 1998, that I saw this thinghappen it was like black magic.
It was the coolest, freakingthing I'd ever seen and I was
hooked.
Like that was it.
I was hooked right then I waslike there's no way I'm going to
be an accountant, I want to bea programmer.
So I called Pricewaterhouse, Itold them I wasn't coming to
(15:24):
join my audit class and I justdove in headfirst and basically
my brother-in-law just kind ofmentored me and he let me play
around and he taught me and backin those days, like we would,
there was no stack overflow, sowe would buy books.
So you would buy.
I don't remember like RocksPress had these.
Remember the red Rocks Pressbooks.
(15:47):
I have a library of them andyou'd buy one on kind of
everything.
So I stayed with my, my dad'scompany for a while but, um, you
know, for for one of a numberof reasons.
Uh, you know, working, workingwith your father is not always
the easiest thing in the world.
So I really wanted to be aprogrammer.
So the way I kind of got intobeing like a real professional
(16:08):
programmer was um, there was a,there was an application for a
job at, um, at, uh, at a web, aweb I guess they like a web
design company in VeniceCalifornia, classic kind of web
1.0 startup.
It was a converted, uh,converted loft and um, the
(16:28):
requirement was you needed to,like you know, be an expert, an
expert in VB and ASP.
And I just literally boughtbooks on Roxpress, learned as
much as I could, somehowsurvived the interview and then
I just learned on the jobbecause the guy next to me was
doing something and he was cooland he kind of taught me on the
job and that was it.
Speaker 1 (16:49):
And from then I just was self-taught, or reading or
learning and and loved everyminute and never looked back and
that's one thing that hasn'tchanged over the years is you're
asked like tremendouslydifficult technical questions in
the interviews, yet on the realjob it's kind of like squashing
bugs and moving data up anddown, and that's it like no.
(17:11):
Yeah, yeah, yeah, you data upand down and that's it Like no.
Speaker 2 (17:13):
Yeah, yeah, you just figure it out.
But that that was my first.
That was my first experienceand and and I don't even think
that job is, is, is is even likeon my LinkedIn.
But this is like.
This was my first kind of realjob being paid as a programmer,
and I was as happy as you can beand and I knew right then that
(17:34):
I had gotten really lucky.
I feel like I've gotten reallylucky in my career because, you
know, when I started myprofessional career, the web was
just taking off and it's likeif that wasn't happening I'm not
saying that I wouldn't havebeen happy as an accountant, but
like I'm so blessed that thetiming worked out, that I was
really starting my career whenthe web was really starting to
(17:56):
blossom and I just got to ridethat wave and and and see, see
it from the beginning, or closeto the beginning.
Speaker 1 (18:03):
It's.
It's funny, there must besomething in the water of like
the big well, like the bigconsultancies that they create
the best entrepreneurs.
Not because we went throughthem Some of you even skipped
them altogether but they kind oflike scare away some really
good talent that they probablywanted to join them because
that's where you forged yourselfright In the flames of
(18:25):
consulting and whatnot.
But then it's like no, I reallydon't want to do this, so I'll
create my own business instead.
I'm ex-Devoid so I can relateto that.
Speaker 2 (18:34):
I mean, I also think it has a lot to do with how
things are at home when you'regrowing up.
I think you know, when I wasgrowing up, I saw my father
always had his own company andso I just assume that that's
what you did.
I assume that everybody was anentrepreneur.
I just assume that that's whatyou did.
I assume that everybody was anentrepreneur.
If I had grown up in a housewhere my parents were lifelong,
(18:57):
were lifers at GE or some hugecompany, maybe that's a path I
would have taken.
But I think a lot of this isformed by the things you see and
hear at home.
You know like another one isthat when we were growing up,
you know my dad had gone toStanford Business School and so
(19:18):
we would always go back to PaloAlto, to Stanford, for football
games and reunions and stuff.
So even before I went tocollege I knew I was going to go
to business school.
I knew I would get my MBA,maybe not at Stanford, but it
was kind of one of these thingswhere it's like it was just it's
.
It's something we talked abouta lot and it's something I saw
and I I just I knew from a youngage, even if I go and become a
(19:43):
programmer, eventually I'm goingto go back to business school
because I don't know.
I just thought that that wassounded like a cool thing to do
and that was all.
That was all kind of brought tome from my father, and so I'm
very lucky that I was.
Speaker 1 (19:53):
I was brought up in that very entrepreneurial
environment it's funny,everybody my family was an
entrepreneur to you and thatthat was the reason why,
precisely, I didn't want tobecome one, because I saw them
all like you saw this failing.
Yeah, I saw the struggle, I sawthe grind and I saw them like
being like all the time, likehaving to suffer the highs and
lows and more lows and highsactually, and having to fire
(20:16):
people downsize the businessevery two or three years I'm
like fuck, no, I don't want todo that.
So it's funny how two differentjust no, it's interesting you
say that.
Speaker 2 (20:24):
it's really interesting.
You say that because my fatherwent through the same thing.
My father had incredible highsand incredible lows and we
basically only my father'sbusiness survived because my mom
always had a steady job to evenout the peaks and valleys.
And I, even though I saw that Iprobably just didn't, maybe I
(20:52):
just didn't like process enough,and now that I look back it's
like, oh my gosh, like there wassuch.
I now know where the peaks andthe valleys were, not because
like there was any suffering oranything, but like I do know
that he went through thatgrinder and, um, you know he
(21:14):
never had like incrediblesuccess, but but like he just
made it work and and and, uh andand was able to kind of grind
it out, um, but but and and.
And.
Also I will say like I'verealized over the years that to
become an entrepreneur you haveto, or the start of business you
have to have like this reallyirrational naivete about you,
(21:36):
like you honestly have to havesomething wrong with you because
, like, because no, I'verealized this Like you have to.
you just have to have thisirrational belief that somehow
you are going to solve a problemthat others can't.
And if you think about thatrationally, it's, it sounds
(21:57):
crazy.
Um, and and so you know, I'veactually found that the older I
get, maybe, the more rationalI've been, which is actually not
good for me as an entrepreneur,because I'll talk myself out of
doing things before I evenstart, which is totally the
wrong thing to do.
And, and, and, and and uh.
Luckily, when I started myfirst company, I was so naive
(22:22):
that we could do something thatwe, we were able to do it.
And, and it's crazy, you, youreally have to, you have to like
.
Speaker 1 (22:36):
It's crazy, you really have to, you have to like
, you have to have something alittle off.
I'm convinced we'reneurodivergent people right.
Yeah, and, by the way, I'm thesame like.
I agree with that.
And there's another thing.
One thing that strikes me asvery interesting from your
profile is that I didn't knowthat you wanted to be an
(22:56):
accountant first, but thatintersection of business and
technology, that's where themost interesting profiles appear
.
Let me rephrase this Basicallymost of the people I admire the
most in this industry are peoplewho are both technical and they
speak business, maybe they comefrom the technical side and
(23:16):
they learn business, like in mycase.
Maybe they come from businessbut they taught themselves how
to program.
And then this intersection it'svery obvious there are not so
many people that can be both aCTO and CEO right or COO in your
case, like when you werementioning your first company,
I'm assuming Vel and CEO rightor COO in your case, like when
you were mentioning your firstcompany, I'm assuming Velocify
right.
So if you want to take me backto when you started and how did
(23:37):
that come around?
Speaker 2 (23:38):
Yeah, so what had happened is so I was.
I had some great roles inengineering as a, as a just a
programmer, but, like I said, Ikind of always knew I wanted to
go back and get my MBA and sowhen I went to, I went to
business school at USC for mygraduate degree, which is two
years, and after my first year Iwas convinced I wanted to go
(24:05):
into venture capital, which islooking back.
Speaker 1 (24:07):
It's the craziest fucking thing I've it's so
fucking idiotic what happenedAfter my first year of business
school.
Speaker 2 (24:13):
I really wanted to be a venture capitalist and so I
was very involved in the.
We had a club at school calledthe Entrepreneurship and Venture
Capital Group.
It was kind of like one grouptogether and our mentor was the
head of the entrepreneurshipdepartment and he knew a guy.
Every great story starts withsomebody knew somebody, right?
(24:35):
So, like my mentor, this guywho was running the
entrepreneurship department, heknew a guy who we would call him
today an angel investor, butthat term didn't exist.
So this was 2002.
So this guy, his name was well,I won't say his name, but we
(24:57):
would consider him an angelinvestor.
He was a guy who, with his ownmoney and maybe some external
investors, was going out andinvesting in startups by himself
, supporting them, helping them,sitting on boards, helping them
work through all the nastyproblems everything from like
(25:17):
personnel issues to legal stuff,to raising capital and so I got
an internship with him in thesummer between my first and
second years of business school,and it was an unpaid internship
and a lot of other people inbusiness school were getting
proper internships where they'remaking money.
I remember my girlfriend at thetime thought I was the
(25:38):
stupidest person in the worldbecause I was like I'm going to
go work for this guy for freeNobody works for free, but I
don't know.
I felt like I needed to justget this experience.
And it was really good becauseI basically just shadowed this
guy for three months or two anda half months and helped him
(26:00):
with modeling and helped himwith investments and helped him
with docs and was on calls withthe lawyers.
But, more importantly, I sat inall these meetings with all
these entrepreneurs and Ilearned something really
important that summer, which wasI didn't want to be the
investor, I wanted to be on theother side of the table, I
wanted to be the guy building,because those guys were the ones
(26:21):
who were having the fun.
And so when I went back toschool in the fall for my second
year, I totally changed myperspective.
I was like, Nope, I don't wantto be an investor, I want to be.
I either want to start acompany or I want to buy a
company and grow it.
And that totally changed myfocus.
And so the way that Velocifywhich previously was called
(26:45):
Leads360, the way that companycame about, was while I was in
business school.
A close friend of mine and Iwere doing some consulting just
to kind of keep the rent paid,because when I was in business
school full-time we're notworking USC was a very expensive
school to go to and we weredoing all these different kind
(27:06):
of consulting projects.
And, as every great storystarts, my friend knew a guy.
And what this guy?
Speaker 1 (27:15):
knew was.
Speaker 2 (27:17):
This guy knew people buying mortgage leads.
So this is 2003, 2004.
And you were surfing around,you'd get served with these
different ads to refinance yourhouse or to get a loan to
purchase a house, and this wasbig business.
These leads were being sold andit was a huge business, and
(27:43):
what I came to find out was thatthere wasn't great software to
manage these leads.
Actually, we knew a guy thatwas buying a lot of leads and he
was actually trying to useSalesforce, which you know, if
you know Salesforce.
Salesforce is like the seminalB2B CRM, right for lead
management and sales kind ofpipeline management.
(28:03):
But the problem he had withSalesforce was Salesforce was
really meant for a B2B sale,which a B2B sale is like a
longer, slower sale, whereastrying to convert somebody who
just clicked the form on theinternet to get you to do a loan
for them was a very hyper,hyper fast B2C transaction, and
(28:29):
so you needed a different typeof product for that.
And so I don't know.
This guy just described thisproblem and the light bulbs kind
of went off and we said well,we can solve that, we can create
basically a B2C version ofSalesforce, which is the best
way to sum it up and we saidokay, we're going to create this
(28:52):
company.
It's going to be calledLeads360.
We're not going to sell leads,we're not going to be part of
the selling of the leads, butwe're going to create a web app
and we're going to get thepeople who pay us for the
software to tell the people thatare sending them the leads hey,
don't email me the leads, sendthem through Leads360 and my
salespeople will be on theLeads360 app and when a new lead
(29:18):
comes in, it'll pop up andthey'll jump on the phone and
they'll try and convert theseguys.
And that basically started.
August of 2004 is when we kindof got that inspiration and we
had a really good group ofpeople.
There were actually four of usat that time.
What happened is there werethree of us guys who were kind
(29:40):
of talking about doing this, andoriginally I was thinking about
being the CTO USC.
I paid all this money to learnhow to I don't want to say not
be an engineer, but to learn howto do things more than just be
an engineer.
So I was like I can't be the CTOon this.
We need to bring in somebodywho really is better than I am
(30:01):
and who knows how to do thisstuff, because I was a little
bit removed as well.
So we actually went to a veryclose, another close friend of
ours and recruited him in and sothe four of us kind of set
about and again we had thisnaivete that we could somehow
solve this problem and through,honestly, like a lot of wind in
(30:26):
our sails because, despite whatpeople tell you, you need a lot
of wind in your sails that youhave nothing to do with.
There was a lot of wind in oursails and a lot of things went
right for us and we had a lot ofsuccess and that was kind of
our first experience buildingand it may be kind of hard to
see through the camera, but I'vegot a lot of gray hair and I
(30:47):
probably got half of those grayhairs working on that company.
Speaker 1 (30:52):
Do you remember the tech stack, the initial tech
stack, and is that somethingthat changed over the years?
Yeah, it was NET.
Speaker 2 (30:56):
Yeah, it was NET.
It was NET and ASPX.
The database was.
I think it was actually IIS wasthe database?
No, iis was the web server, thedatabase, sql server, stored
(31:16):
procedures, all that kind ofstuff, wow, blast from the past.
Speaker 1 (31:22):
Oh yeah, that tech stack still haunts me at night.
Speaker 2 (31:25):
Yeah, but it served us okay, I mean it served us
well and it worked out becausewe were able to get there was a
lot of engineers who knew thatstack and we were able to get
get a good team around it, sothat's great um, but it's funny
that you sort of intentionallyremove yourself from potentially
being the cto of your owncompany, right, and let me, let
(31:50):
me.
Speaker 1 (31:50):
Let me tell you why, like most engineers, most
software developers, they dreamof becoming a cto, right, and
that's why I wanted to coverthese today.
Um, I've got the feeling thatnot enough podcasts, no, there's
not enough content on how tobecome a cto.
It's kind of like people simplybecome one cto.
It's like angel investing.
How do you become an angelinvestor?
(32:11):
There's not not a lot ofliterature out there.
You either are one one or arenot.
It's binary, right, but the CTOis much more complex.
The CTO is a gradual process.
Of course, you can labelyourself as a CTO of your own
one-man show if you create acompany and I'm founder and CTO
Well, yeah, a CTO of what You'reactually writing code.
(32:34):
But you could have been the CTO, but you decided to take on
this operational role, maybebecause you were sitting at the
intersection of business andtechnology, right, and then,
with Affinity, it happened again.
You also were not the CTO.
So is that also intentional orwhat happened there?
Why did you choose COO of allthe titles available to you?
Speaker 2 (32:53):
Yeah, I mean I think so I'm not a huge fan of the
titles or labels.
I mean I love building and insome cases when I've built
things I've been the mosttechnical person there and great
.
So then give me some technicaltitle, right?
(33:14):
And, by the way, like I don'tconsider myself some great CTO
Like the size of teams that I'vemanaged had never been terribly
big, and being a good CTO takesskills that, honestly, I don't
even really have right, like I'mprobably a much better engineer
than I am a CTO.
Because I'm probably a muchbetter engineer than I am a CTO,
because once you're a CTO of alarge organization, your role is
(33:36):
so much more about managementand people at any of those kind
of C-level roles, right.
And so I always thought ofmyself as an operator, like I.
Just so, when I got out ofbusiness school and I said, hey,
(33:56):
I don't necessarily want toprogram, it wasn't because I
didn't want to build, I justdidn't want to build software, I
wanted to build a company, andI look at the two very similarly
.
I want to do it in an efficientway, I want to do it in an
elegant way, I want it to beable to scale right, like I look
at building a company theentity, the people, the
(34:16):
processes, the products asexciting as building, you know,
the actual software, right, andso operations to me always just
felt like something that suitedme, and and and so, and so I
I've never really consideredmyself like a, you know, like a
technical co-founder.
(34:37):
Um, because I always wanted tohave a really wide perspective.
I want to, I want to be part ofthe strategy discussions, I
want to be part of the legaldiscussions and, yes, I want to
deeply understand the technologybecause and yes, I want to
deeply understand the technologybecause there's actually I have
(34:58):
this need to really deeplyunderstand anything I do it's
like a real kind of psychosiswant to understand the
technology down to the, as far,as close to bare metal as
possible, because it just helpsme.
I just feel like I need to dothat to understand the business
(35:20):
as a whole.
But I don't necessarily want tobe the tech person.
So like I've been in roleswhere I am the tech guy, but but
even in those roles I was stillwith the CEO on strategy and
all these other things becauseI've spent so many years and
I've seen so many situationsfrom every aspect of company
(35:41):
building.
That it's like to kind of tosilo yourself and say, okay, I'm
only going to be working on thetechnology to me was just never
going to be fun, right.
And so, like, even as aninvestor right now, like when I
look at at companies that I'mtrying to invest in, I have an
advantage over a lot ofinvestors because I can deeply,
(36:03):
deeply understand the technology.
I mean not every technology, Imean some of the stuff we've
talked about at your quantumcomputing is a little bit over
my head but, but I can at leastgrasp what we're trying to do
here, but then I can havethoughtful comments on all these
other pieces of the business.
(36:25):
So I think, if you look at mycareer, the one thread that has
gone through all of myexperiences, that is that there
has been there.
There's technology, and I'vegone kind of in and out of these
engineering roles.
I mean, um, I think, um,building software is something
that I'll probably always love.
I I don't kind of know how todo it anymore because I'm, you
(36:48):
know, I'm kind of removed, but,um, I'm, you know, I'm kind of
removed, but it's, it's really,it's a really powerful tool.
It's a.
It's a good thing to know, butit's also really good to be
well-rounded, right, I mean,particularly if there's one of
you, or two of you.
You know you're you got to beable to put input in all these
different areas, but you're.
Speaker 1 (37:09):
I mean, I don't know if that's the most accurate
adjective, but I think you are afire starter.
You're the kind of person thatwants to get involved in the
initial stages of the companyProbably that skills too much.
Then you're not interestedanymore and you sort of want to
be a generalist because you likesolving puzzles and that sort
(37:32):
of like hits close to my case aswell, which, like when we
created Marsbase, I was a CMObecause it was in charge of
marketing.
I was not even CEO and, likeyou, I don't like roles.
The reason why I adopted theCEO role and I think that's
something that I've neverexplained, but it's because
potential clients want to talkto the CEO, not to the CMO.
(37:52):
Cmo is kind of like the Ryanairof the C-levels, you know.
It's kind of like a super lowcost or second level, and so
it's more like an outwardslooking title.
Inwards.
The three co-founders are moreor less like CEO-ing around the
company and the three of uscould be the CTO and the CEO and
(38:15):
the something else.
Right?
Speaker 2 (38:17):
Yeah.
Speaker 1 (38:17):
So I sort of understand that.
I see that by being ageneralist and this
entrepreneurial mindset allowsus to create a company, At the
same time, while this is verygood in the initial stages of a
company, eventually you hit alevel in which you sort of
required to change the mindsetand delegate, optimize,
(38:39):
outsource, eliminate, hire forspecialists.
I'm starting to feel like thisin March.
I think we're a little bitearly, but I'm now feeling like
we're required specialists in acouple of areas, have you like?
Is this description accurate orI'm totally?
Speaker 2 (38:56):
off the mark.
No, it's totally accurate.
I'll actually tell you anexperience.
Speaker 1 (38:59):
I had.
Where's the level, where's thelimit?
Speaker 2 (39:02):
Well, I'll tell you an experience I had where.
So when we started our firstcompany in 2004, there were four
founders.
One of the founders was boughtout along the way, so then there
were three of us and thecompany got to a point where it
(39:27):
was getting really big and,frankly, I was getting for lack
of a better term bored.
Like I love the early your term.
Fire starters is great.
I'm going to steal that from you, but I love some of those kind
of like those like early, earlyproblems, and when our, when
that first company got to apoint where the were ones that
(39:50):
just weren't very exciting to me, I, I, I, I felt disinterested,
and I am the kind of personthat I am.
I have a personality flaw whereI have to be all in on
something.
If I'm not all in on something,I you'll lose me.
(40:11):
I just it's just how I am.
I'm like it's.
I have a hard time being reallygiving in when I'm not giving
it all, when I'm not reallyinvested mentally, and so when I
started mentally checking out,it became very clear to my
co-founders, and so I was thefirst of the three of us sorry,
(40:33):
the second of the fourco-founders to exit the company.
And so I exited the company in2009, basically took some time
off, actually got married, andwhen I was thinking about what I
was going to do after that, Ifound myself at this really
tough crossroads, because I'dspent all this time becoming
(40:57):
this really general operator andI had no real specialty.
I wasn't a programmer, I had nokind of like special skills,
and I felt like my two choicesat that fork in the road was I
either start a new company or Iget hired to like run another
(41:21):
company, like in a very kind ofgeneral role, and it was.
It felt very awkward, I feltvery kind of lost because I was
like I don't have anydiscernible skills Like what do
you, how do you apply for a jobwhen you your?
Your last job was, you know,kind of building a company, I
don't know.
It just felt very foreign to me, and so what I ended up doing
(41:46):
was I ended up getting an iPhoneanother amazing window for me
where I got an iPhone and I sawall these apps on the iPhone and
I was like, oh, that's cool, Ican make these.
And so I taught myself how todo that.
And I was like, oh, that's cool, I can make these.
And so I taught myself how todo that.
And then I learned enough thatI then got another job as an
(42:06):
iPhone developer, as an appdeveloper, and that started this
whole other phase where I wentback into engineering.
So like I was out of engineering, I went back into engineering
and I loved it.
I was like as happy as can be.
I, you know, really could justdive into the, into programming,
and I really loved it.
Um, but but um, you're right,you can the entrepreneurial
(42:35):
journey.
You can find yourself in kindof odd, odd, odd spots.
You know, um, and I I don'tknow.
I just feel very fortunate thatI've been able to kind of like
figure things out and getthrough different kind of
valleys or kind of connectvalleys in the career.
And so if you look at my resumeor you look at my LinkedIn,
it's not going to be the mostbeautifully manicured timeline,
(43:00):
right, it's like it's got somespots here and there like
they're.
Speaker 1 (43:06):
Anybody that tells?
Speaker 2 (43:07):
you.
Otherwise is probably lyingbecause, like the reality is
like you're right as anentrepreneur, if you have, you
know, it's like I've had a tinybit of success and a ton of
failure and you know and, and,and.
So have most people.
So it's like anybody that tellsyou that it's all good and
they're killing it and all thisother bullshit.
(43:29):
It's like most likely a lie.
Speaker 1 (43:31):
But in the corporate industry, you know, gap years or
sabbaticals are seen as aperceived as something lazy or
perceived as something negative,whereas when I see that in
serial entrepreneurs, taking gapyears means you've had success
because otherwise you would havechained, you would have
concatenated companies becauseyou were failing.
(43:52):
So I need to start fast becauseI'm running out of money.
If you take, more often thannot, gaps of two or three or
four years, like in your case,that means you were a little bit
well off, so that means youcould actually spend or at least
afford that time.
Or because you didn't includeyour freelancing gigs, as you
(44:12):
mentioned.
Right, but at least it givesyou the impression that, wow, he
really took time to enjoyhimself.
Think, maybe, experiment, livea little bit of life, travel
around get some experiences andthen, you know, create something
new.
Speaker 2 (44:29):
And I don't know.
We've been very fortunate tohave that.
Yeah, I mean, we're veryfortunate to be able to live in
this great city.
We're, you know, fortunate tobe able to spend a lot of time
with our kids.
We're fortunate that, you know,we don't have to work multiple
jobs, which a lot of people do,and so we recognize that it's
(44:50):
definitely a special time.
Speaker 1 (44:52):
But it's funny because you said you didn't want
to be the CTO and you wanted tokind of like, didn't want to
box yourself into just being theCTO and not being able to work
in other areas of the company.
Yet in one of your most recentjob experiences return mates you
were the CTO, right?
So how did that happen?
Like why, in that case?
Speaker 2 (45:12):
Well, again, it's because it's just timing.
So what had happened is so wesold the first company Lease360,
that got renamed to Velocify.
That company sold in 2017, 13years later, and so everybody
(45:36):
did very well.
I started doing a lot of kindof family planning, estate
planning and talking to a lot ofadvisors around what to do with
money and investments and stuff, and just it's because the way
my mind works, I started usingall this software that these big
(45:59):
banks and were giving me tokind of get visibility into my
assets and things, and I waslike, man, this software sucks.
And so I basically was like I'mjust going to create my own.
And so I basically spent abouta year and a half building a.
(46:23):
It's essentially like a familyoffice platform for me and my
family and it's like mint onsteroids, because at that time
there was mint and then therewas this other platform called
personal capital and then therewere all these kind of
institutional platforms and Ineeded something in between,
because I've got assets thatnone of these things could
(46:44):
manage, like crypto, and I'vegot a bunch of these angel
investments and I just had, Iwanted things done in a certain
way.
So the product guy in me waslike, fuck it, I'll build my own
platform.
And so what happened is I waslike, okay, I haven't programmed
forever, I've got to relearnhow the kids are doing this now.
(47:04):
So I basically said, well, Idon't want to learn front end,
I'll just do the back end,because the back end was always
more natural to me.
So I got a front end developerin Ukraine and me and this guy
basically built this platformthat, by the way, I still use
today to manage all of myfamily's affairs.
(47:25):
It's really awesome.
And so when I was kind of donebuilding that, this opportunity
came around where a good friendof mine knew a couple
entrepreneurs in LA that werelooking for a technical person
to join their team, and it justhappened that I had been.
I just spent a year and a halfgetting up on like the latest
(47:49):
and greatest in development, andso it was like, oh well,
charles can help you, becausenot only does he have all this
experience building companiesand he can invest in the company
, but like he can literally rollup his sleeves and like build
the whole thing by himself.
So that's what I did.
I joined these guys in LA and,despite having a family and and
(48:11):
you know a wife and three kidsin San Diego.
I took the train up to LA, uh,twice a week, would stay on the
the founder's couch.
I literally, you know, I'm, I'ma, I'm an older guy and I'm,
you know, sleeping on this guy'scouch and we're building this
product day and night.
It was super fun.
It was like this, really cool,like renaissance, and in that
(48:33):
role I was, you know, like I wasthe CTO.
I built the kind of whole firstnot the first data version of it
before I came, but we rebuiltthe whole platform, hired the
team, but with those guys theywere really great guys.
They're just fantasticentrepreneurs and I think that
they knew that I had a lot ofexperience to bring to the table
(48:56):
and they never treated me likea CTO.
They always treated me like anequal.
They always, you know, theygave me tons of equity and they
always asked for my opinion oneverything from legal to
strategy and I was able to helpthem because I had kind of been
through all that.
But then, yes, I still did allthe engineering and built out
(49:19):
that team.
But again, it was one of thesethings where it was like right
place, right time, you know,like if you came to me right now
and somebody wanted me to bethe CTO, I'd be like I can't do
it.
I don't know.
I don't even have VS Code on mylaptop anymore.
Speaker 1 (49:35):
But five years ago you know fairly enough, you
mentioned like when you startedwas 20 years ago, there was no
Stack Overflow, it was not evenclose to getting started.
But five years ago we had StackOverflow, we had Google, we had
Reddit, we had all of thesedocumentation everywhere.
(49:58):
Nowadays you even have, like,if I wanted to become the CTO of
something, I would be going tochat GPT, basically just asking
questions, cursor, blah, blah,blah.
How did you do it five yearsago?
Because, after so many years ofnot actually being in the
trenches, so much of technology,what was the thought process?
What tools did you use?
Was it books?
Was it courses, was it, I don'tknow, diy everything?
(50:22):
No, courses, was it?
Speaker 2 (50:22):
like I don't know diy everything or no.
Actually I I'm trying to thinkof how I figured it out, but um,
the technology changes a lotlike five years ago.
Speaker 1 (50:31):
You know containers where, everywhere, but like 20
years ago, that technologydidn't exist.
How did you bring up to catchup with everything?
Speaker 2 (50:38):
I'm trying, I, I, so I was.
I talked with a developer, Iwas talking with a guy and we
were I was trying to think of'scalled AppSync, and it was
(51:04):
basically a way to you know,it's kind of one of you know how
AWS has all these integratedproducts.
It was a way where you couldreally quickly launch a.
It's essentially like a GraphQLserver that talked to a.
(51:24):
At that time you could use, youknow, different databases, but
I think we used like a Postgresdatabase and it made it just
made development super easy.
It was like, as you know, likewith development, it's all about
like layers of abstraction,right, like you've got bare
metal, like you've got the baremetal and then you've got like,
(51:45):
how many layers of abstractionare you at Right, like um, and
so this was a tool that waspretty far removed and and and
made it really easy to kind ofbuild, spin up a backend.
I.
I had never used GraphQL before, so I had to learn GraphQL and
that was a fun thing, but I alsoanother theme that I will share
with you is because I'msomewhat of a.
(52:06):
I like to torture myself.
I always force myself to likelearn something new.
So, like, for some godforsakenreason.
I decided, oh, I'm going to dothis thing in GraphQL.
And I had never even heard ofGraphQL.
But I was like, oh, I love it,it's super cool, it looks super
elegant and it was hard as shitto figure out, but once I
(52:28):
figured it out it was super cool.
And so sometimes when peopleask me like, oh, how did you
choose to do this?
It was like, well, I talked toa guy and he kind of turned me
onto this thing and I've alwaysloved AWS and they seem to have
nice tools.
And I just started playing withit and I was like, okay, cool,
this works.
And you know, kind of off wewent and then, you know, the
(52:49):
front end was all you know,react and TypeScript and
JavaScript, but I was not on thefront end of that side.
But yeah, I mean the tools.
Now ChatGPT, I haven't.
I know that you're super deepin the ChatGPT and, by the way,
I use ChatGPT and Perplexitypretty much all like a lot every
(53:11):
day.
I've actually used it a lotmore since I met you.
You've definitely inspired meto use those tools more and I,
the more I use them, the more Ithem I'm.
I'm still kind of like not surewhich one I love better chat,
gpt or perplexity, um, but um,they're amazing, so good, and so
I'm not really sure how guysare using them today.
(53:33):
I mean, I know there's thingslike copilot and, and
everybody's got a, a companionor a tool.
I'm not sure how people areusing it today.
I don't know if developers aresaying like, hey, write me a,
you know, write me some functionto do this.
That'd be amazing.
But, like I, I never had theopportunity to do that and I, I
I'm not.
You know, I've got kind ofmixed feelings on it a little
(53:54):
bit well, I mean you should try.
Speaker 1 (53:57):
You should try it.
It's interesting.
It's not going to solve all theworld's problems, but at least
it helps you get rid of theblank canvas syndrome.
And, for instance, I'm kind oflike the super, like a person
that finds a lot of trouble indeciding the stack of things or
how to organize project foldersand stuff like that, because I'm
(54:18):
you know, I'm kind of like this, I'm a perfectionist, so it it
is helping me to get rid ofperfectionism.
Just because it's like get shitdone right.
It's like, oh, I want this.
It's like that Boom, no excuses, it's done already.
You can debate whether youwould reorganize.
You know the assets here andthese other like organization of
folders.
Speaker 2 (54:38):
Right, you're doing PTSD, talking about folder
structure?
Speaker 1 (54:48):
Exactly no, but that's the thing like for me, it
up until now it would have beenan excuse, or, oh, I don't know
.
React I'm not going to start aproject until I master react and
I start with.
No, it's not, I need a reactproject for this.
Like boom, it gets it done, andlike you start building on
something, so it activates acertain part of your brain where
you are able to kind of likecorrect, connect and um, and
maybe like calibrate if you want, instead of figuring out the
(55:09):
stuff.
That it's kind of like it'sbinary, it's done or it's not
done, but uh, it doesn't reallyrequire a lot of gray matter,
right?
So, um, the more mechanicaltasks you don't need to figure
out.
Then after that you can perfectit to your brain's content and
whatnot, right, and so it.
It works precisely like that.
Hey, now write a controller thatdoes this.
(55:29):
Or I want to rewrite the viewsand react instead of like pure
rails application, whatnot.
It will do it, but because youand I have got the domain
expertise, we're able to see allthe implications, because the
the problem with this kind of AIis like it really does that,
but because it's an AI, it justexecutes.
Like the context is prettylimited and so some of these
(55:55):
decisions doesn't like itdoesn't take into account
long-term vision, whereas youwould do it.
So it gets the job done forthat context, for that specific
prompt.
But maybe this changes too muchin the backend or changes other
parts of the application that,if you're able to spot it,
(56:17):
you're like, yeah, but don't dothis, don't do that.
You should actually scope like azero in, like a little bit,
limit more the scope of theprompt, otherwise it will just
touch the entire application andyou don't want that Like, oh,
write me just a model and doonly this, but do not
specifically do the blah blah,blah, blah, blah.
(56:37):
So the more accurate you are.
That's why I've been writing alot about spaghetti prompting
lately, because there's acorrelation between spaghetti
prompting and spaghetti codingand I think that it actually
happens.
Same with AI.
I see a lot of people who arelike, oh, yeah, I got an app in
React running in 10 minutes andlike, look at this.
(56:58):
But yeah, great, that's a zeroto one, but the one to five it's
going to take forever becauseyou will be iterating 10,000
times.
It will not work and then youwill ask it to solve this bug,
but because it doesn't reallyunderstand everything and you
don't understand what the AI isdoing, you're not able to
correct it and therefore youwould be just beating around the
bush all the time.
Speaker 2 (57:19):
So that's why I'm skeptical but optimist.
Speaker 1 (57:22):
Yeah, before wrapping it up, because we're close to
an hour now and I want you tohave some kind of space to give
advice to aspiring entrepreneurswho might be looking for
somebody like you, like youspecifically speaking about like
technical enough to run as aCTO, but who can decide whether
(57:43):
to be the CTO, the operationsguy or these fire starters who
get shit done.
Basically, where do you findpeople like you?
Speaker 2 (57:52):
Yeah, I mean, I think it was the question where do
they find people like me?
Speaker 1 (57:57):
Yeah, and more importantly, how do they keep
you around in these companies?
Speaker 2 (58:01):
What I'm most interested in doing right now is
until I have some inspirationto able to bring to kind before
they even have anything right, Ithink.
(58:50):
I think one of the interestingthings that I found here in
Barcelona is my sense is thatthe investors are a little bit
more conservative here.
They want to see some things.
They want to see kind of moreprogress where, like I, want to
back people based on them as aperson and not what I think that
(59:16):
they're building.
Because a lot of times, like Igot this question recently from
Notch Merner they said do youinvest based on product or do
you invest on person?
And my answer is person all day, because the product is going
to change and the bestentrepreneurs that I've backed
have always had changes in theirproducts.
It's just the nature of it.
(59:37):
It's an organic thing.
If you invested based on aproduct and then the product
changes, you might get kind ofdisappointed, whereas I want to
invest in people who have athesis and have a, an idea of
how they want to solve a problem, but, by the way, like that,
the way you solve that or wayyou approach that thesis might
change.
And so you know what I'mlooking for in this ecosystem
(01:00:01):
and the conversations that Ilove to have are just with
people who are trying to buildstuff and who are inspired to
build things, and I don't onlydo technology investments One of
my best investments is a beautycompany in Los Angeles but I
want to meet and be inspired byother builders and I want to be
(01:00:24):
basically the first check.
I want to invest before anybodyelse invests, because it's at
that point that I can help themost.
It's at that point that I canhelp with all the things, from
helping them legally or helpingthem do advice on hiring and
advice, obviously, on technology.
But you know, the bigger acompany gets, the less they need
(01:00:45):
, they need me and also the lessI get.
I'm interested, right.
So, like you know, one of thethings that I'm trying to do is
is is just talk to as manyinteresting people as I can who
are building cool things and andmy advice is always free
(01:01:06):
building cool things and and myadvice is always free and if I'm
, if I, if I'm excited enough,I'm going to want to, I'm going
to want to, I'm going to want to, you know, back it up with with
some money, and I'm at a reallyfortunate place right now where
, you know, I can support otherentrepreneurs, which I think is
super cool, and and and I I kindof consider it like planting
seeds, like I want to plantseeds and I want to water them,
(01:01:26):
and that's what I'm really goodat, um, and I'm really good at.
I think I'm really good at umbetting on people Like I.
I I have an intuition aboutpeople and I feel like I'm I I
have a pretty good track recordof of, of betting on the right
people, um, and so that's, youknow, it goes full circle to why
(01:01:50):
I reached out to you originallybecause, like you know, when I
met you, you're an amazingperson.
You're, you know, you're verymodest person, but you know,
you're one of the mostwell-connected people in this
town and so, like there's somany great people here and I
just want to hear what peopleare up to and if somebody needs
support, before some they need acheck and before other people
write a check, like I want totalk to them because I probably
(01:02:18):
will take more risks than otherswill, and part of that is
because there's a littlesomething off with me.
Speaker 1 (01:02:27):
There's quite a lot of things to unwrap here, but
basically, thank you for thekind words.
The respect is mutual.
That's one Second.
The interest the thing that youmentioned about keeping you
interested is very importantbecause I think one of the most
common mistakes entrepreneurs dowhen hiring or when trying to
fish for technical profiles islike oh, they want somebody to
(01:02:49):
produce code or hire engineers.
And it's like well, that is notinteresting.
Most technical people, they'renot driven by money or
aspirations or fame or whatever.
They just want to solve realproblems.
And if the problems are notinteresting, they will not join
your company.
So, and if the company theymight have a short-term problem,
it's okay, but then you willnot keep these people for very
(01:03:12):
long because, like, the interestdissipates over the years.
So, yeah, you raise a reallyinteresting point.
And the other thing that I thinkis really interesting from your
profile as well and that'ssomething that I also share in
my sort of pitch when I'mpitching entrepreneurs where I
want to invest, in whom I wantto invest, is I'm a technical
(01:03:34):
person.
Right, and precisely, there arenot so many CTOs or technical
people investing that can audityour technology, that can vouch
for your architect, or that canhelp you hire a CTO investing
that can audit your technology,that can vouch for your
architect or that can help youhire a CTO that can help you
audit or inspect your API orsort of like figure out
integrations and stuff like that.
So I think that's actually avery good value proposition for
(01:03:56):
an angel investor.
That sort of distinguishes usfrom other profiles.
Before we wrap it up and we'reway over time, but this is
getting very interesting andthis is a signature question of
the podcast is what has beenyour most expensive technical
fuck up so far has to be yours.
We have to own up to it mostexpensive, yeah one big fuck up
(01:04:22):
that he like, oh jeez, it kindof like wiped out production
database or I mean, don't worry,no pressure, somebody set their
office on fire and so you'renot going to top that one
Pressure's off.
Speaker 2 (01:04:35):
Hmm, I gotta think about this one.
I mean, most of my fuck-ups arenot technical.
Most of my fuck-ups are humanfuck-ups.
Speaker 1 (01:04:51):
Okay.
Speaker 2 (01:04:58):
Let's go for that one , and the most kind of issues
I've had in my career, the mostkind of challenges I've had in
my career, are not technicalones, they're people ones and
they're mostly focused aroundjust having high EQ or, in my
(01:05:19):
case early on in my career,having very low EQ.
And so when I was building myfirst company, I really was not
concerned with the human side ofthings.
I was trying to build a greatproduct and I was trying to
build a really successfulcompany, and I didn't really
give a shit about how peoplefelt, or I didn't really care
(01:05:41):
about how people thought aboutme, and I think that created a
lot of issues for me, because,you know, building companies is
a a human endeavor, right?
Like?
I don't care how technical theproduct is or the software is or
(01:06:02):
whether it's quantum computing.
Humans are building thesethings.
These humans need their act,and it took me a long time to
figure this out and I'm stillfiguring it out how to be a more
emotionally intelligent person,how to really understand the
(01:06:28):
lens of the people that areworking with you and working for
you.
That changed everything for me.
So, like, I've never burned anoffice down, I've never deleted
a production database.
But I have, you know, reallykilled some relationships.
I've, I've, I've turned a lotof people off.
I've been a complete asshole.
(01:06:50):
Um, you know, uh and uh it'ssomething that I've worked on
for the last 15 years is reallytrying to be a, uh, more
emotionally intelligent person,a more understanding person and
um, and yeah, I'd, I'd saythat's, that's my, those are my
(01:07:17):
big fuck ups and and and that'sthe stuff that I kind of try and
work on.
Speaker 1 (01:07:21):
Thanks for sharing, thanks for opening up.
You've been extremely generouswith your time and with your
advice.
Any parting words?
I'm rolling out the carpet foryou, so 30 seconds.
How can we help you back?
Speaker 2 (01:07:33):
Yeah, I mean.
I just say, if anybody listensto this pod and is trying to
build some stuff, whether you'rein Barcelona or not, I'd love
to talk to you.
I'd love to share with youanything I can and, like I said,
I'll share with anybody forfree.
I'll tell you my unfilteredthoughts and if you're doing
something really exciting, I'dlove to invest.
Speaker 1 (01:07:57):
And we will see you building something.
If you don't find anybody elsedoing something interesting,
We'll see Charles if you don'tfind anybody else doing
something interesting.
Speaker 2 (01:08:03):
We'll see.
Speaker 1 (01:08:05):
Charles, thank you very much.
Speaker 2 (01:08:06):
Thanks, alex, great to see you Awesome.
Hello everybody and welcome to Life on Mars.
I'm Alex, ceo and founder ofMarsBased, and in this episode
we bring you Charles Chase, aserial entrepreneur and investor
who created companies likeVelocify, affinity and many
other ventures, and we discusswith him his career as a serial
entrepreneur and how to become atechnical co-founder or a CTO,
(00:21):
even though he has opted not tobe a CTO in many cases, even
though he taught himself how tocode.
He taught himself how to be atechnologist, but he only served
as a CTO in one case in hiscareer.
But we discussed this and moreof that.
We discussed also buildingcompanies, investing, the
differences between the US andBarcelona, and how to be a
(00:43):
newcomer to a startup ecosystem.
So, without further ado, let'sjump right into this episode and
then, you know, you tell meabout your arrival on St Geordie
Day last year.
Speaker 2 (01:02):
Yeah well, first of all, happy St Geordie Day last
year.
Yeah well, first of all, happySt Geordie Day.
If any of my American friendslisten to this, I guess you can
correct me, but my understandingis St Geordie Day is kind of
like Valentine's Day and maybesome other stuff wrapped in one,
and my son, who goes to aCatalan school, is learning the
(01:22):
story of the dragon and how therose came about.
But the cool thing for ourfamily with St Jordi's Day is,
you know, before we decided tomove here, we came and did a.
You know, we had been in Spaina number of times and we knew we
loved it.
But we came to revisit and seethe schools that our kids might
(01:44):
go to.
And that was on St Jordi's Dayand it was not a great day to
fly in because it took about anhour and a half to get here in a
cab, Because if you're inBarcelona on that day, the whole
city is just like it's not anofficial holiday, but it's like
a holiday.
The streets are crazy, Anyway.
So today, waking up and seeingeverybody celebrate, it was
really kind of special for ourfamily.
Speaker 1 (02:06):
Well then, welcome to Barcelona, Welcome to Life on
Mars.
Actually, thank you foragreeing to do this.
I really like your profile.
We met a few months ago, justto give some context to the
audience.
We met a few months ago andyour profile is very interesting
because we oftentimes we get alot of American expats coming
(02:26):
over to Barcelona, right, butrarely ever they are on the
technical side of things.
Usually, you know, retiredinvestors or people more like on
the CEO slash CFO, more like onthe business side of things,
right, or ex-VP at a givenmassive multinational, ex-vp at
Apple, ex-vp at a given massivemultinational, ex-vp at Apple,
ex-vp at Vodafone, or somethinglike that.
(02:49):
But in your case, like well, weshould.
I think Barcelona is in severedemand of more experienced
serial founders that come fromthe technical side of things.
So that's why I wanted tohighlight a little bit your
career, if you're up for it.
So where do we want to start?
Do you want to give some?
Highlight a little bit yourcareer, if you're up for it, so
uh yeah where do we want tostart?
do you want to get?
Speaker 2 (03:07):
I don't know if you remember how we met.
But basically, when I got here,I really wanted to understand
what the technology kind ofstartup ecosystem was.
So I think I googled barcelonastartups and startup grind came
up.
Your name came up.
I think I sent you a cold email, correct, and, and.
So, yeah, you're my friend,you're my first, you're one of
(03:29):
my first friends here and one ofmy and certainly my first kind
of like startup friend, and, and, and, and you've been so
generous and introduced me to somany cool people and and and
and taking me to events, and so,um, yeah, it was just I.
I've spent so many years, um,building things myself and being
(03:50):
around other builders that, um,when I got here, I just wanted
to see, see what was happeningand who was building what, and
um, it has I there's.
There's so many surprises that Iwould never have guessed.
First, of how vibrant thecommunity is here, but also just
the insane amount ofopportunity given so many
(04:12):
factors that we can talk aboutin from investors and how they
look at the market, and I thinkBarcelona and Spain, I in
general is such like a.
It's such a like a underdogmarket, like.
I think if you look at Europe,you know, everybody thinks about
Berlin and the UK.
But there's so much cool stuffand there's so many amazing
(04:33):
founders here, but yet my senseis that they're undervalued.
And so, you know, theentrepreneur or the early stage
investor in me is like oh mygosh, that's an amazing
opportunity for me because youknow I can do things and maybe I
have a competitive advantage.
Speaker 1 (04:53):
You know, so that's cool.
This narrative sort of bringsme to one of the realizations
I've had over the past few years, which is Barcelona has the
potentiality and the capacity tobecome a tier one startup
ecosystem.
Yet I think it's better if wedon't.
(05:15):
Right, why?
Because you know it keepsvaluations down.
It keeps the cost of talentdown as well.
It keeps the cost of talentdown as well.
It brings other founders toinitiate and start up their new
(05:36):
companies here, preciselybecause the cost of starting up
is lower than in other vibrantecosystems.
At the same time, you more orless get everything you would
get from every place else.
Maybe you don't get tier oneelse.
Maybe you don't get tier one,um, I wouldn't say talent, but
maybe infrastructure like youwould get in silicon valley, you
would get in london, you wouldget in tel aviv or berlin and
stuff like that.
But it's a trade-off, right.
At the same time, it's kind oflike where do you want to be?
Like the small?
(05:56):
The small fish in the big pond,the big fish in the small pond,
or you can be like a reallycool fish in the best
motherfucking pond of all time.
Right, and that's where I thinkBarcelona should place itself.
Speaker 2 (06:08):
Yeah, yeah, I mean, the people I've met here are so
motivated and so smart, and I'veonly been here six months, so I
can't imagine where we go fromhere.
Speaker 1 (06:22):
Tell me more about your arrival, because actually
your story sort of resonateswith mine.
When I arrived first in the US,I didn't know anybody, so I
called email people, one ofwhich was people at Startup
Grind, but the other people Imessaged I remember the first
people to respond to one of mycold messages.
I arrived in San Francisco onChristmas Day 2013, and I called
(06:46):
a message from the plane theBarcelona San Francisco
Association, something like thatand a very high-level person
replied to me and first I didn'tholy fuck, I'm meeting this guy
tomorrow and he was like aVSTOPTR VC serial founder, like
(07:08):
chairman of 27 associations,stuff like that.
And so he said I got 30 minutesfor you, miguel Valls.
I'll never forget the name.
He opened me the first doors inSan Francisco, which in turn,
they open more doors.
So that first contact, it'salways very important.
That's why I try to be thatkind of person, even though I'm
not high level, as he was.
But I try to open the doors tosomebody else because you never
(07:32):
know right.
Most of all, I like to be anambassador of my own city.
So, but you took the first step, you called, message a few
people to see what was going on.
So what's the thought processbehind?
Like I'm going to reach out totech leaders in the industry.
Speaker 2 (07:49):
Well, I mean the kind of stepping back the you know
the impetus for us moving toSpain, and so you know I'm
married and we have three, threekids and you know the impetus
for us moving to Spain wasreally about trying to provide
our kids a maybe a broaderviewpoint on the world.
(08:14):
You know we were the kids hadfirst grown up in Los Angeles
and then during COVID, we hadmoved about an hour and a half
south to a really small beachtown called Solana Beach in San
Diego, california.
It's a really idyllic place togrow up and to have kids, but
(08:35):
it's a little insular, right.
If you never left, you wouldnot really understand or have a
very broad perspective in myviewpoint.
So we had come to Spain anumber of times.
My wife's sister is married toa Spaniard, so we've spent a lot
of time here.
(08:55):
So you know there was a window.
You know you need these windowsright.
Like during COVID, there was awindow and that got us to San
Diego.
Like during COVID, there was awindow and that got us to San
Diego, and the window thatbrought us to Spain was my
oldest was about to start hisfreshman year in American high
school, which is this reallykind of seminal, important time
(09:15):
in a young person's life and Iknew that once he started high
school in the US it would behard to kind of get out at high
school in the US.
It would be hard to kind of getout.
But we slowly started thisconversation when he was still
in eighth grade, which is, youknow, kind of the end of primary
school there, and he was allfor it.
My oldest is really adventurousand if he wasn't adventurous
(09:43):
and if he was really set onstaying there, we wouldn't be
here, right?
Because the kids had to buy in.
So you know, we came out hereand when we came out here I
wasn't working on any projects.
I was.
You know, I basically tellpeople I'm on sabbatical.
You know, I can't tell I'm 50,I can't tell people I'm retired.
I can't tell I'm 50.
I can't tell people I'm retired.
(10:06):
And so we got moved in and mywife and I have went out and
were tourists in the city formany, many days.
But then I felt like, okay, Ineed to start meeting some
people.
And so I'm a builder, I want tobuild things, I want to support
other builders, I want to hearabout what people are building.
I just I like I don't know, Ilike geeking out on things
(10:30):
getting built.
You know it's been that way mywhole life, right, like when I
was a kid.
I just love building things andwhether it's software or Legos
or a company, I just it reallyexcites me and so I just wanted
this, I wanted this like hereand see like what are people
building here?
Obviously, I know about some ofthe big companies, like global
(10:51):
and stuff like that, but I'mmuch more interested in like
what's that one person, that oneguy or girl building that
they're really passionate about?
And that was that was theimpetus for for trying to get
into the ecosystem, because Ineed that part for my spirit.
I need to be part of thebuilding of things or hearing
(11:18):
about it, and that reallyfulfills a big part of my
professional life.
That was the impetus for that?
Speaker 1 (11:28):
how do you become a software engineer?
When did you want to start likeprogramming, coding?
Speaker 2 (11:33):
uh, take me back to that, yeah time so I, when I was
in college, um, I studiedeconomics and accounting and I
was really set on becoming anaccountant and a CPA.
I actually graduated college in1996, and I had a job at a big
accounting firm called PriceWaterhouse, and what happened
(11:58):
was I graduated a quarter late,so I was, instead of graduating,
travel around Europe were, youknow, not going to happen.
(12:27):
So my father had a softwarecompany.
Although my father was not asoftware engineer, he was like a
marketing guy and actually areally good product designer,
and so he had been working inthe software business actually
since the 70s, before there waseven really software.
He was doing all this consultingand then they had their first
(12:49):
software was on the mainframes,um, and so in 97, um, his
company was thinking abouttaking their, uh, their their
software, which was like a verykind of traditional client
server where you had, you know,these kind of fat clients
(13:10):
probably getting too technicalhere, but you know you had a
bunch of software installed on aperson's computer that talked
to a server, and mybrother-in-law, who was a CTO at
that time, kind of got thisidea or got this inspiration to
create a web interface, and ifyou think back, this was super,
(13:31):
super, super early.
So they were going to create aweb interface for their product.
They were thinking about doingit in like 96 or 97, which was
really, really, really early,and so I went there to help them
, not in a programming role, butlike in a I don't know, just a
do-anything kind of role, right.
Speaker 1 (13:50):
A webmaster.
We called them webmasters backin the day.
Speaker 2 (13:56):
And I just got interested in the.
I got interested in thebuilding and actually my
brother-in-law who I owe anincredible debt to, basically
one day gave me a book on HTMLand I went home I read this book
on HTML.
I was like okay, cool.
And then he set me up like alittle sandbox and I started
building little HTML pages.
(14:16):
Then he got me a book onJavaScript and I started reading
that, started doing that, andthen I think the thing for me
the big like aha moment was Idon't know if you remember, but
Microsoft used to have this webserver called Internet
Information Server IAS.
Yeah, and they had thistechnology called Active Server
(14:39):
Pages, asp, yep, and with ASPyou could from a web page, make
a call to a database, query thedatabase and then write to the
page a table or whatever right.
I'm getting goosebumps justthinking about it now, because
the first time I saw that happenwhich was probably in like 1997
(15:03):
, 1998, that I saw this thinghappen it was like black magic.
It was the coolest, freakingthing I'd ever seen and I was
hooked.
Like that was it.
I was hooked right then I waslike there's no way I'm going to
be an accountant, I want to bea programmer.
So I called Pricewaterhouse, Itold them I wasn't coming to
(15:24):
join my audit class and I justdove in headfirst and basically
my brother-in-law just kind ofmentored me and he let me play
around and he taught me and backin those days, like we would,
there was no stack overflow, sowe would buy books.
So you would buy.
I don't remember like RocksPress had these.
Remember the red Rocks Pressbooks.
(15:47):
I have a library of them andyou'd buy one on kind of
everything.
So I stayed with my, my dad'scompany for a while but, um, you
know, for for one of a numberof reasons.
Uh, you know, working, workingwith your father is not always
the easiest thing in the world.
So I really wanted to be aprogrammer.
So the way I kind of got intobeing like a real professional
(16:08):
programmer was um, there was a,there was an application for a
job at, um, at, uh, at a web, aweb I guess they like a web
design company in VeniceCalifornia, classic kind of web
1.0 startup.
It was a converted, uh,converted loft and um, the
(16:28):
requirement was you needed to,like you know, be an expert, an
expert in VB and ASP.
And I just literally boughtbooks on Roxpress, learned as
much as I could, somehowsurvived the interview and then
I just learned on the jobbecause the guy next to me was
doing something and he was cooland he kind of taught me on the
job and that was it.
Speaker 1 (16:49):
And from then I just was self-taught, or reading or
learning and and loved everyminute and never looked back and
that's one thing that hasn'tchanged over the years is you're
asked like tremendouslydifficult technical questions in
the interviews, yet on the realjob it's kind of like squashing
bugs and moving data up anddown, and that's it like no.
(17:11):
Yeah, yeah, yeah, you data upand down and that's it Like no.
Speaker 2 (17:13):
Yeah, yeah, you just figure it out.
But that that was my first.
That was my first experienceand and and I don't even think
that job is, is, is is even likeon my LinkedIn.
But this is like.
This was my first kind of realjob being paid as a programmer,
and I was as happy as you can beand and I knew right then that
(17:34):
I had gotten really lucky.
I feel like I've gotten reallylucky in my career because, you
know, when I started myprofessional career, the web was
just taking off and it's likeif that wasn't happening I'm not
saying that I wouldn't havebeen happy as an accountant, but
like I'm so blessed that thetiming worked out, that I was
really starting my career whenthe web was really starting to
(17:56):
blossom and I just got to ridethat wave and and and see, see
it from the beginning, or closeto the beginning.
Speaker 1 (18:03):
It's.
It's funny, there must besomething in the water of like
the big well, like the bigconsultancies that they create
the best entrepreneurs.
Not because we went throughthem Some of you even skipped
them altogether but they kind oflike scare away some really
good talent that they probablywanted to join them because
that's where you forged yourselfright In the flames of
(18:25):
consulting and whatnot.
But then it's like no, I reallydon't want to do this, so I'll
create my own business instead.
I'm ex-Devoid so I can relateto that.
Speaker 2 (18:34):
I mean, I also think it has a lot to do with how
things are at home when you'regrowing up.
I think you know, when I wasgrowing up, I saw my father
always had his own company andso I just assume that that's
what you did.
I assume that everybody was anentrepreneur.
I just assume that that's whatyou did.
I assume that everybody was anentrepreneur.
If I had grown up in a housewhere my parents were lifelong,
(18:57):
were lifers at GE or some hugecompany, maybe that's a path I
would have taken.
But I think a lot of this isformed by the things you see and
hear at home.
You know like another one isthat when we were growing up,
you know my dad had gone toStanford Business School and so
(19:18):
we would always go back to PaloAlto, to Stanford, for football
games and reunions and stuff.
So even before I went tocollege I knew I was going to go
to business school.
I knew I would get my MBA,maybe not at Stanford, but it
was kind of one of these thingswhere it's like it was just it's
.
It's something we talked abouta lot and it's something I saw
and I I just I knew from a youngage, even if I go and become a
(19:43):
programmer, eventually I'm goingto go back to business school
because I don't know.
I just thought that that wassounded like a cool thing to do
and that was all.
That was all kind of brought tome from my father, and so I'm
very lucky that I was.
Speaker 1 (19:53):
I was brought up in that very entrepreneurial
environment it's funny,everybody my family was an
entrepreneur to you and thatthat was the reason why,
precisely, I didn't want tobecome one, because I saw them
all like you saw this failing.
Yeah, I saw the struggle, I sawthe grind and I saw them like
being like all the time, likehaving to suffer the highs and
lows and more lows and highsactually, and having to fire
(20:16):
people downsize the businessevery two or three years I'm
like fuck, no, I don't want todo that.
So it's funny how two differentjust no, it's interesting you
say that.
Speaker 2 (20:24):
it's really interesting.
You say that because my fatherwent through the same thing.
My father had incredible highsand incredible lows and we
basically only my father'sbusiness survived because my mom
always had a steady job to evenout the peaks and valleys.
And I, even though I saw that Iprobably just didn't, maybe I
(20:52):
just didn't like process enough,and now that I look back it's
like, oh my gosh, like there wassuch.
I now know where the peaks andthe valleys were, not because
like there was any suffering oranything, but like I do know
that he went through thatgrinder and, um, you know he
(21:14):
never had like incrediblesuccess, but but like he just
made it work and and and, uh andand was able to kind of grind
it out, um, but but and and.
And.
Also I will say like I'verealized over the years that to
become an entrepreneur you haveto, or the start of business you
have to have like this reallyirrational naivete about you,
(21:36):
like you honestly have to havesomething wrong with you because
, like, because no, I'verealized this Like you have to.
you just have to have thisirrational belief that somehow
you are going to solve a problemthat others can't.
And if you think about thatrationally, it's, it sounds
(21:57):
crazy.
Um, and and so you know, I'veactually found that the older I
get, maybe, the more rationalI've been, which is actually not
good for me as an entrepreneur,because I'll talk myself out of
doing things before I evenstart, which is totally the
wrong thing to do.
And, and, and, and and uh.
Luckily, when I started myfirst company, I was so naive
(22:22):
that we could do something thatwe, we were able to do it.
And, and it's crazy, you, youreally have to, you have to like
.
Speaker 1 (22:36):
It's crazy, you really have to, you have to like
, you have to have something alittle off.
I'm convinced we'reneurodivergent people right.
Yeah, and, by the way, I'm thesame like.
I agree with that.
And there's another thing.
One thing that strikes me asvery interesting from your
profile is that I didn't knowthat you wanted to be an
(22:56):
accountant first, but thatintersection of business and
technology, that's where themost interesting profiles appear
.
Let me rephrase this Basicallymost of the people I admire the
most in this industry are peoplewho are both technical and they
speak business, maybe they comefrom the technical side and
(23:16):
they learn business, like in mycase.
Maybe they come from businessbut they taught themselves how
to program.
And then this intersection it'svery obvious there are not so
many people that can be both aCTO and CEO right or COO in your
case, like when you werementioning your first company,
I'm assuming Vel and CEO rightor COO in your case, like when
you were mentioning your firstcompany, I'm assuming Velocify
right.
So if you want to take me backto when you started and how did
(23:37):
that come around?
Speaker 2 (23:38):
Yeah, so what had happened is so I was.
I had some great roles inengineering as a, as a just a
programmer, but, like I said, Ikind of always knew I wanted to
go back and get my MBA and sowhen I went to, I went to
business school at USC for mygraduate degree, which is two
years, and after my first year Iwas convinced I wanted to go
(24:05):
into venture capital, which islooking back.
Speaker 1 (24:07):
It's the craziest fucking thing I've it's so
fucking idiotic what happenedAfter my first year of business
school.
Speaker 2 (24:13):
I really wanted to be a venture capitalist and so I
was very involved in the.
We had a club at school calledthe Entrepreneurship and Venture
Capital Group.
It was kind of like one grouptogether and our mentor was the
head of the entrepreneurshipdepartment and he knew a guy.
Every great story starts withsomebody knew somebody, right?
(24:35):
So, like my mentor, this guywho was running the
entrepreneurship department, heknew a guy who we would call him
today an angel investor, butthat term didn't exist.
So this was 2002.
So this guy, his name was well,I won't say his name, but we
(24:57):
would consider him an angelinvestor.
He was a guy who, with his ownmoney and maybe some external
investors, was going out andinvesting in startups by himself
, supporting them, helping them,sitting on boards, helping them
work through all the nastyproblems everything from like
(25:17):
personnel issues to legal stuff,to raising capital and so I got
an internship with him in thesummer between my first and
second years of business school,and it was an unpaid internship
and a lot of other people inbusiness school were getting
proper internships where they'remaking money.
I remember my girlfriend at thetime thought I was the
(25:38):
stupidest person in the worldbecause I was like I'm going to
go work for this guy for freeNobody works for free, but I
don't know.
I felt like I needed to justget this experience.
And it was really good becauseI basically just shadowed this
guy for three months or two anda half months and helped him
(26:00):
with modeling and helped himwith investments and helped him
with docs and was on calls withthe lawyers.
But, more importantly, I sat inall these meetings with all
these entrepreneurs and Ilearned something really
important that summer, which wasI didn't want to be the
investor, I wanted to be on theother side of the table, I
wanted to be the guy building,because those guys were the ones
(26:21):
who were having the fun.
And so when I went back toschool in the fall for my second
year, I totally changed myperspective.
I was like, Nope, I don't wantto be an investor, I want to be.
I either want to start acompany or I want to buy a
company and grow it.
And that totally changed myfocus.
And so the way that Velocifywhich previously was called
(26:45):
Leads360, the way that companycame about, was while I was in
business school.
A close friend of mine and Iwere doing some consulting just
to kind of keep the rent paid,because when I was in business
school full-time we're notworking USC was a very expensive
school to go to and we weredoing all these different kind
(27:06):
of consulting projects.
And, as every great storystarts, my friend knew a guy.
And what this guy?
Speaker 1 (27:15):
knew was.
Speaker 2 (27:17):
This guy knew people buying mortgage leads.
So this is 2003, 2004.
And you were surfing around,you'd get served with these
different ads to refinance yourhouse or to get a loan to
purchase a house, and this wasbig business.
These leads were being sold andit was a huge business, and
(27:43):
what I came to find out was thatthere wasn't great software to
manage these leads.
Actually, we knew a guy thatwas buying a lot of leads and he
was actually trying to useSalesforce, which you know, if
you know Salesforce.
Salesforce is like the seminalB2B CRM, right for lead
management and sales kind ofpipeline management.
(28:03):
But the problem he had withSalesforce was Salesforce was
really meant for a B2B sale,which a B2B sale is like a
longer, slower sale, whereastrying to convert somebody who
just clicked the form on theinternet to get you to do a loan
for them was a very hyper,hyper fast B2C transaction, and
(28:29):
so you needed a different typeof product for that.
And so I don't know.
This guy just described thisproblem and the light bulbs kind
of went off and we said well,we can solve that, we can create
basically a B2C version ofSalesforce, which is the best
way to sum it up and we saidokay, we're going to create this
(28:52):
company.
It's going to be calledLeads360.
We're not going to sell leads,we're not going to be part of
the selling of the leads, butwe're going to create a web app
and we're going to get thepeople who pay us for the
software to tell the people thatare sending them the leads hey,
don't email me the leads, sendthem through Leads360 and my
salespeople will be on theLeads360 app and when a new lead
(29:18):
comes in, it'll pop up andthey'll jump on the phone and
they'll try and convert theseguys.
And that basically started.
August of 2004 is when we kindof got that inspiration and we
had a really good group ofpeople.
There were actually four of usat that time.
What happened is there werethree of us guys who were kind
(29:40):
of talking about doing this, andoriginally I was thinking about
being the CTO USC.
I paid all this money to learnhow to I don't want to say not
be an engineer, but to learn howto do things more than just be
an engineer.
So I was like I can't be the CTOon this.
We need to bring in somebodywho really is better than I am
(30:01):
and who knows how to do thisstuff, because I was a little
bit removed as well.
So we actually went to a veryclose, another close friend of
ours and recruited him in and sothe four of us kind of set
about and again we had thisnaivete that we could somehow
solve this problem and through,honestly, like a lot of wind in
(30:26):
our sails because, despite whatpeople tell you, you need a lot
of wind in your sails that youhave nothing to do with.
There was a lot of wind in oursails and a lot of things went
right for us and we had a lot ofsuccess and that was kind of
our first experience buildingand it may be kind of hard to
see through the camera, but I'vegot a lot of gray hair and I
(30:47):
probably got half of those grayhairs working on that company.
Speaker 1 (30:52):
Do you remember the tech stack, the initial tech
stack, and is that somethingthat changed over the years?
Yeah, it was NET.
Speaker 2 (30:56):
Yeah, it was NET.
It was NET and ASPX.
The database was.
I think it was actually IIS wasthe database?
No, iis was the web server, thedatabase, sql server, stored
(31:16):
procedures, all that kind ofstuff, wow, blast from the past.
Speaker 1 (31:22):
Oh yeah, that tech stack still haunts me at night.
Speaker 2 (31:25):
Yeah, but it served us okay, I mean it served us
well and it worked out becausewe were able to get there was a
lot of engineers who knew thatstack and we were able to get
get a good team around it, sothat's great um, but it's funny
that you sort of intentionallyremove yourself from potentially
being the cto of your owncompany, right, and let me, let
(31:50):
me.
Speaker 1 (31:50):
Let me tell you why, like most engineers, most
software developers, they dreamof becoming a cto, right, and
that's why I wanted to coverthese today.
Um, I've got the feeling thatnot enough podcasts, no, there's
not enough content on how tobecome a cto.
It's kind of like people simplybecome one cto.
It's like angel investing.
How do you become an angelinvestor?
(32:11):
There's not not a lot ofliterature out there.
You either are one one or arenot.
It's binary, right, but the CTOis much more complex.
The CTO is a gradual process.
Of course, you can labelyourself as a CTO of your own
one-man show if you create acompany and I'm founder and CTO
Well, yeah, a CTO of what You'reactually writing code.
(32:34):
But you could have been the CTO, but you decided to take on
this operational role, maybebecause you were sitting at the
intersection of business andtechnology, right, and then,
with Affinity, it happened again.
You also were not the CTO.
So is that also intentional orwhat happened there?
Why did you choose COO of allthe titles available to you?
Speaker 2 (32:53):
Yeah, I mean I think so I'm not a huge fan of the
titles or labels.
I mean I love building and insome cases when I've built
things I've been the mosttechnical person there and great
.
So then give me some technicaltitle, right?
(33:14):
And, by the way, like I don'tconsider myself some great CTO
Like the size of teams that I'vemanaged had never been terribly
big, and being a good CTO takesskills that, honestly, I don't
even really have right, like I'mprobably a much better engineer
than I am a CTO.
Because I'm probably a muchbetter engineer than I am a CTO,
because once you're a CTO of alarge organization, your role is
(33:36):
so much more about managementand people at any of those kind
of C-level roles, right.
And so I always thought ofmyself as an operator, like I.
Just so, when I got out ofbusiness school and I said, hey,
(33:56):
I don't necessarily want toprogram, it wasn't because I
didn't want to build, I justdidn't want to build software, I
wanted to build a company, andI look at the two very similarly
.
I want to do it in an efficientway, I want to do it in an
elegant way, I want it to beable to scale right, like I look
at building a company theentity, the people, the
(34:16):
processes, the products asexciting as building, you know,
the actual software, right, andso operations to me always just
felt like something that suitedme, and and and so, and so I
I've never really consideredmyself like a, you know, like a
technical co-founder.
(34:37):
Um, because I always wanted tohave a really wide perspective.
I want to, I want to be part ofthe strategy discussions, I
want to be part of the legaldiscussions and, yes, I want to
deeply understand the technologybecause and yes, I want to
deeply understand the technologybecause there's actually I have
(34:58):
this need to really deeplyunderstand anything I do it's
like a real kind of psychosiswant to understand the
technology down to the, as far,as close to bare metal as
possible, because it just helpsme.
I just feel like I need to dothat to understand the business
(35:20):
as a whole.
But I don't necessarily want tobe the tech person.
So like I've been in roleswhere I am the tech guy, but but
even in those roles I was stillwith the CEO on strategy and
all these other things becauseI've spent so many years and
I've seen so many situationsfrom every aspect of company
(35:41):
building.
That it's like to kind of tosilo yourself and say, okay, I'm
only going to be working on thetechnology to me was just never
going to be fun, right.
And so, like, even as aninvestor right now, like when I
look at at companies that I'mtrying to invest in, I have an
advantage over a lot ofinvestors because I can deeply,
(36:03):
deeply understand the technology.
I mean not every technology, Imean some of the stuff we've
talked about at your quantumcomputing is a little bit over
my head but, but I can at leastgrasp what we're trying to do
here, but then I can havethoughtful comments on all these
other pieces of the business.
(36:25):
So I think, if you look at mycareer, the one thread that has
gone through all of myexperiences, that is that there
has been there.
There's technology, and I'vegone kind of in and out of these
engineering roles.
I mean, um, I think, um,building software is something
that I'll probably always love.
I I don't kind of know how todo it anymore because I'm, you
(36:48):
know, I'm kind of removed, but,um, I'm, you know, I'm kind of
removed, but it's, it's really,it's a really powerful tool.
It's a.
It's a good thing to know, butit's also really good to be
well-rounded, right, I mean,particularly if there's one of
you, or two of you.
You know you're you got to beable to put input in all these
different areas, but you're.
Speaker 1 (37:09):
I mean, I don't know if that's the most accurate
adjective, but I think you are afire starter.
You're the kind of person thatwants to get involved in the
initial stages of the companyProbably that skills too much.
Then you're not interestedanymore and you sort of want to
be a generalist because you likesolving puzzles and that sort
(37:32):
of like hits close to my case aswell, which, like when we
created Marsbase, I was a CMObecause it was in charge of
marketing.
I was not even CEO and, likeyou, I don't like roles.
The reason why I adopted theCEO role and I think that's
something that I've neverexplained, but it's because
potential clients want to talkto the CEO, not to the CMO.
(37:52):
Cmo is kind of like the Ryanairof the C-levels, you know.
It's kind of like a super lowcost or second level, and so
it's more like an outwardslooking title.
Inwards.
The three co-founders are moreor less like CEO-ing around the
company and the three of uscould be the CTO and the CEO and
(38:15):
the something else.
Right?
Speaker 2 (38:17):
Yeah.
Speaker 1 (38:17):
So I sort of understand that.
I see that by being ageneralist and this
entrepreneurial mindset allowsus to create a company, At the
same time, while this is verygood in the initial stages of a
company, eventually you hit alevel in which you sort of
required to change the mindsetand delegate, optimize,
(38:39):
outsource, eliminate, hire forspecialists.
I'm starting to feel like thisin March.
I think we're a little bitearly, but I'm now feeling like
we're required specialists in acouple of areas, have you like?
Is this description accurate orI'm totally?
Speaker 2 (38:56):
off the mark.
No, it's totally accurate.
I'll actually tell you anexperience.
Speaker 1 (38:59):
I had.
Where's the level, where's thelimit?
Speaker 2 (39:02):
Well, I'll tell you an experience I had where.
So when we started our firstcompany in 2004, there were four
founders.
One of the founders was boughtout along the way, so then there
were three of us and thecompany got to a point where it
(39:27):
was getting really big and,frankly, I was getting for lack
of a better term bored.
Like I love the early your term.
Fire starters is great.
I'm going to steal that from you, but I love some of those kind
of like those like early, earlyproblems, and when our, when
that first company got to apoint where the were ones that
(39:50):
just weren't very exciting to me, I, I, I, I felt disinterested,
and I am the kind of personthat I am.
I have a personality flaw whereI have to be all in on
something.
If I'm not all in on something,I you'll lose me.
(40:11):
I just it's just how I am.
I'm like it's.
I have a hard time being reallygiving in when I'm not giving
it all, when I'm not reallyinvested mentally, and so when I
started mentally checking out,it became very clear to my
co-founders, and so I was thefirst of the three of us sorry,
(40:33):
the second of the fourco-founders to exit the company.
And so I exited the company in2009, basically took some time
off, actually got married, andwhen I was thinking about what I
was going to do after that, Ifound myself at this really
tough crossroads, because I'dspent all this time becoming
(40:57):
this really general operator andI had no real specialty.
I wasn't a programmer, I had nokind of like special skills,
and I felt like my two choicesat that fork in the road was I
either start a new company or Iget hired to like run another
(41:21):
company, like in a very kind ofgeneral role, and it was.
It felt very awkward, I feltvery kind of lost because I was
like I don't have anydiscernible skills Like what do
you, how do you apply for a jobwhen you your?
Your last job was, you know,kind of building a company, I
don't know.
It just felt very foreign to me, and so what I ended up doing
(41:46):
was I ended up getting an iPhoneanother amazing window for me
where I got an iPhone and I sawall these apps on the iPhone and
I was like, oh, that's cool, Ican make these.
And so I taught myself how todo that.
And I was like, oh, that's cool, I can make these.
And so I taught myself how todo that.
And then I learned enough thatI then got another job as an
(42:06):
iPhone developer, as an appdeveloper, and that started this
whole other phase where I wentback into engineering.
So like I was out of engineering, I went back into engineering
and I loved it.
I was like as happy as can be.
I, you know, really could justdive into the, into programming,
and I really loved it.
Um, but but um, you're right,you can the entrepreneurial
(42:35):
journey.
You can find yourself in kindof odd, odd, odd spots.
You know, um, and I I don'tknow.
I just feel very fortunate thatI've been able to kind of like
figure things out and getthrough different kind of
valleys or kind of connectvalleys in the career.
And so if you look at my resumeor you look at my LinkedIn,
it's not going to be the mostbeautifully manicured timeline,
(43:00):
right, it's like it's got somespots here and there like
they're.
Speaker 1 (43:06):
Anybody that tells?
Speaker 2 (43:07):
you.
Otherwise is probably lyingbecause, like the reality is
like you're right as anentrepreneur, if you have, you
know, it's like I've had a tinybit of success and a ton of
failure and you know and, and,and.
So have most people.
So it's like anybody that tellsyou that it's all good and
they're killing it and all thisother bullshit.
(43:29):
It's like most likely a lie.
Speaker 1 (43:31):
But in the corporate industry, you know, gap years or
sabbaticals are seen as aperceived as something lazy or
perceived as something negative,whereas when I see that in
serial entrepreneurs, taking gapyears means you've had success
because otherwise you would havechained, you would have
concatenated companies becauseyou were failing.
(43:52):
So I need to start fast becauseI'm running out of money.
If you take, more often thannot, gaps of two or three or
four years, like in your case,that means you were a little bit
well off, so that means youcould actually spend or at least
afford that time.
Or because you didn't includeyour freelancing gigs, as you
(44:12):
mentioned.
Right, but at least it givesyou the impression that, wow, he
really took time to enjoyhimself.
Think, maybe, experiment, livea little bit of life, travel
around get some experiences andthen, you know, create something
new.
Speaker 2 (44:29):
And I don't know.
We've been very fortunate tohave that.
Yeah, I mean, we're veryfortunate to be able to live in
this great city.
We're, you know, fortunate tobe able to spend a lot of time
with our kids.
We're fortunate that, you know,we don't have to work multiple
jobs, which a lot of people do,and so we recognize that it's
(44:50):
definitely a special time.
Speaker 1 (44:52):
But it's funny because you said you didn't want
to be the CTO and you wanted tokind of like, didn't want to
box yourself into just being theCTO and not being able to work
in other areas of the company.
Yet in one of your most recentjob experiences return mates you
were the CTO, right?
So how did that happen?
Like why, in that case?
Speaker 2 (45:12):
Well, again, it's because it's just timing.
So what had happened is so wesold the first company Lease360,
that got renamed to Velocify.
That company sold in 2017, 13years later, and so everybody
(45:36):
did very well.
I started doing a lot of kindof family planning, estate
planning and talking to a lot ofadvisors around what to do with
money and investments and stuff, and just it's because the way
my mind works, I started usingall this software that these big
(45:59):
banks and were giving me tokind of get visibility into my
assets and things, and I waslike, man, this software sucks.
And so I basically was like I'mjust going to create my own.
And so I basically spent abouta year and a half building a.
(46:23):
It's essentially like a familyoffice platform for me and my
family and it's like mint onsteroids, because at that time
there was mint and then therewas this other platform called
personal capital and then therewere all these kind of
institutional platforms and Ineeded something in between,
because I've got assets thatnone of these things could
(46:44):
manage, like crypto, and I'vegot a bunch of these angel
investments and I just had, Iwanted things done in a certain
way.
So the product guy in me waslike, fuck it, I'll build my own
platform.
And so what happened is I waslike, okay, I haven't programmed
forever, I've got to relearnhow the kids are doing this now.
(47:04):
So I basically said, well, Idon't want to learn front end,
I'll just do the back end,because the back end was always
more natural to me.
So I got a front end developerin Ukraine and me and this guy
basically built this platformthat, by the way, I still use
today to manage all of myfamily's affairs.
(47:25):
It's really awesome.
And so when I was kind of donebuilding that, this opportunity
came around where a good friendof mine knew a couple
entrepreneurs in LA that werelooking for a technical person
to join their team, and it justhappened that I had been.
I just spent a year and a halfgetting up on like the latest
(47:49):
and greatest in development, andso it was like, oh well,
charles can help you, becausenot only does he have all this
experience building companiesand he can invest in the company
, but like he can literally rollup his sleeves and like build
the whole thing by himself.
So that's what I did.
I joined these guys in LA and,despite having a family and and
(48:11):
you know a wife and three kidsin San Diego.
I took the train up to LA, uh,twice a week, would stay on the
the founder's couch.
I literally, you know, I'm, I'ma, I'm an older guy and I'm,
you know, sleeping on this guy'scouch and we're building this
product day and night.
It was super fun.
It was like this, really cool,like renaissance, and in that
(48:33):
role I was, you know, like I wasthe CTO.
I built the kind of whole firstnot the first data version of it
before I came, but we rebuiltthe whole platform, hired the
team, but with those guys theywere really great guys.
They're just fantasticentrepreneurs and I think that
they knew that I had a lot ofexperience to bring to the table
(48:56):
and they never treated me likea CTO.
They always treated me like anequal.
They always, you know, theygave me tons of equity and they
always asked for my opinion oneverything from legal to
strategy and I was able to helpthem because I had kind of been
through all that.
But then, yes, I still did allthe engineering and built out
(49:19):
that team.
But again, it was one of thesethings where it was like right
place, right time, you know,like if you came to me right now
and somebody wanted me to bethe CTO, I'd be like I can't do
it.
I don't know.
I don't even have VS Code on mylaptop anymore.
Speaker 1 (49:35):
But five years ago you know fairly enough, you
mentioned like when you startedwas 20 years ago, there was no
Stack Overflow, it was not evenclose to getting started.
But five years ago we had StackOverflow, we had Google, we had
Reddit, we had all of thesedocumentation everywhere.
(49:58):
Nowadays you even have, like,if I wanted to become the CTO of
something, I would be going tochat GPT, basically just asking
questions, cursor, blah, blah,blah.
How did you do it five yearsago?
Because, after so many years ofnot actually being in the
trenches, so much of technology,what was the thought process?
What tools did you use?
Was it books?
Was it courses, was it, I don'tknow, diy everything?
(50:22):
No, courses, was it?
Speaker 2 (50:22):
like I don't know diy everything or no.
Actually I I'm trying to thinkof how I figured it out, but um,
the technology changes a lotlike five years ago.
Speaker 1 (50:31):
You know containers where, everywhere, but like 20
years ago, that technologydidn't exist.
How did you bring up to catchup with everything?
Speaker 2 (50:38):
I'm trying, I, I, so I was.
I talked with a developer, Iwas talking with a guy and we
were I was trying to think of'scalled AppSync, and it was
(51:04):
basically a way to you know,it's kind of one of you know how
AWS has all these integratedproducts.
It was a way where you couldreally quickly launch a.
It's essentially like a GraphQLserver that talked to a.
(51:24):
At that time you could use, youknow, different databases, but
I think we used like a Postgresdatabase and it made it just
made development super easy.
It was like, as you know, likewith development, it's all about
like layers of abstraction,right, like you've got bare
metal, like you've got the baremetal and then you've got like,
(51:45):
how many layers of abstractionare you at Right, like um, and
so this was a tool that waspretty far removed and and and
made it really easy to kind ofbuild, spin up a backend.
I.
I had never used GraphQL before, so I had to learn GraphQL and
that was a fun thing, but I alsoanother theme that I will share
with you is because I'msomewhat of a.
(52:06):
I like to torture myself.
I always force myself to likelearn something new.
So, like, for some godforsakenreason.
I decided, oh, I'm going to dothis thing in GraphQL.
And I had never even heard ofGraphQL.
But I was like, oh, I love it,it's super cool, it looks super
elegant and it was hard as shitto figure out, but once I
(52:28):
figured it out it was super cool.
And so sometimes when peopleask me like, oh, how did you
choose to do this?
It was like, well, I talked toa guy and he kind of turned me
onto this thing and I've alwaysloved AWS and they seem to have
nice tools.
And I just started playing withit and I was like, okay, cool,
this works.
And you know, kind of off wewent and then, you know, the
(52:49):
front end was all you know,react and TypeScript and
JavaScript, but I was not on thefront end of that side.
But yeah, I mean the tools.
Now ChatGPT, I haven't.
I know that you're super deepin the ChatGPT and, by the way,
I use ChatGPT and Perplexitypretty much all like a lot every
(53:11):
day.
I've actually used it a lotmore since I met you.
You've definitely inspired meto use those tools more and I,
the more I use them, the more Ithem I'm.
I'm still kind of like not surewhich one I love better chat,
gpt or perplexity, um, but um,they're amazing, so good, and so
I'm not really sure how guysare using them today.
(53:33):
I mean, I know there's thingslike copilot and, and
everybody's got a, a companionor a tool.
I'm not sure how people areusing it today.
I don't know if developers aresaying like, hey, write me a,
you know, write me some functionto do this.
That'd be amazing.
But, like I, I never had theopportunity to do that and I, I
I'm not.
You know, I've got kind ofmixed feelings on it a little
(53:54):
bit well, I mean you should try.
Speaker 1 (53:57):
You should try it.
It's interesting.
It's not going to solve all theworld's problems, but at least
it helps you get rid of theblank canvas syndrome.
And, for instance, I'm kind oflike the super, like a person
that finds a lot of trouble indeciding the stack of things or
how to organize project foldersand stuff like that, because I'm
(54:18):
you know, I'm kind of like this, I'm a perfectionist, so it it
is helping me to get rid ofperfectionism.
Just because it's like get shitdone right.
It's like, oh, I want this.
It's like that Boom, no excuses, it's done already.
You can debate whether youwould reorganize.
You know the assets here andthese other like organization of
folders.
Speaker 2 (54:38):
Right, you're doing PTSD, talking about folder
structure?
Speaker 1 (54:48):
Exactly no, but that's the thing like for me, it
up until now it would have beenan excuse, or, oh, I don't know
.
React I'm not going to start aproject until I master react and
I start with.
No, it's not, I need a reactproject for this.
Like boom, it gets it done, andlike you start building on
something, so it activates acertain part of your brain where
you are able to kind of likecorrect, connect and um, and
maybe like calibrate if you want, instead of figuring out the
(55:09):
stuff.
That it's kind of like it'sbinary, it's done or it's not
done, but uh, it doesn't reallyrequire a lot of gray matter,
right?
So, um, the more mechanicaltasks you don't need to figure
out.
Then after that you can perfectit to your brain's content and
whatnot, right, and so it.
It works precisely like that.
Hey, now write a controller thatdoes this.
(55:29):
Or I want to rewrite the viewsand react instead of like pure
rails application, whatnot.
It will do it, but because youand I have got the domain
expertise, we're able to see allthe implications, because the
the problem with this kind of AIis like it really does that,
but because it's an AI, it justexecutes.
Like the context is prettylimited and so some of these
(55:55):
decisions doesn't like itdoesn't take into account
long-term vision, whereas youwould do it.
So it gets the job done forthat context, for that specific
prompt.
But maybe this changes too muchin the backend or changes other
parts of the application that,if you're able to spot it,
(56:17):
you're like, yeah, but don't dothis, don't do that.
You should actually scope like azero in, like a little bit,
limit more the scope of theprompt, otherwise it will just
touch the entire application andyou don't want that Like, oh,
write me just a model and doonly this, but do not
specifically do the blah blah,blah, blah, blah.
(56:37):
So the more accurate you are.
That's why I've been writing alot about spaghetti prompting
lately, because there's acorrelation between spaghetti
prompting and spaghetti codingand I think that it actually
happens.
Same with AI.
I see a lot of people who arelike, oh, yeah, I got an app in
React running in 10 minutes andlike, look at this.
(56:58):
But yeah, great, that's a zeroto one, but the one to five it's
going to take forever becauseyou will be iterating 10,000
times.
It will not work and then youwill ask it to solve this bug,
but because it doesn't reallyunderstand everything and you
don't understand what the AI isdoing, you're not able to
correct it and therefore youwould be just beating around the
bush all the time.
Speaker 2 (57:19):
So that's why I'm skeptical but optimist.
Speaker 1 (57:22):
Yeah, before wrapping it up, because we're close to
an hour now and I want you tohave some kind of space to give
advice to aspiring entrepreneurswho might be looking for
somebody like you, like youspecifically speaking about like
technical enough to run as aCTO, but who can decide whether
(57:43):
to be the CTO, the operationsguy or these fire starters who
get shit done.
Basically, where do you findpeople like you?
Speaker 2 (57:52):
Yeah, I mean, I think it was the question where do
they find people like me?
Speaker 1 (57:57):
Yeah, and more importantly, how do they keep
you around in these companies?
Speaker 2 (58:01):
What I'm most interested in doing right now is
until I have some inspirationto able to bring to kind before
they even have anything right, Ithink.
(58:50):
I think one of the interestingthings that I found here in
Barcelona is my sense is thatthe investors are a little bit
more conservative here.
They want to see some things.
They want to see kind of moreprogress where, like I, want to
back people based on them as aperson and not what I think that
(59:16):
they're building.
Because a lot of times, like Igot this question recently from
Notch Merner they said do youinvest based on product or do
you invest on person?
And my answer is person all day, because the product is going
to change and the bestentrepreneurs that I've backed
have always had changes in theirproducts.
It's just the nature of it.
(59:37):
It's an organic thing.
If you invested based on aproduct and then the product
changes, you might get kind ofdisappointed, whereas I want to
invest in people who have athesis and have a, an idea of
how they want to solve a problem, but, by the way, like that,
the way you solve that or wayyou approach that thesis might
change.
And so you know what I'mlooking for in this ecosystem
(01:00:01):
and the conversations that Ilove to have are just with
people who are trying to buildstuff and who are inspired to
build things, and I don't onlydo technology investments One of
my best investments is a beautycompany in Los Angeles but I
want to meet and be inspired byother builders and I want to be
(01:00:24):
basically the first check.
I want to invest before anybodyelse invests, because it's at
that point that I can help themost.
It's at that point that I canhelp with all the things, from
helping them legally or helpingthem do advice on hiring and
advice, obviously, on technology.
But you know, the bigger acompany gets, the less they need
(01:00:45):
, they need me and also the lessI get.
I'm interested, right.
So, like you know, one of thethings that I'm trying to do is
is is just talk to as manyinteresting people as I can who
are building cool things and andmy advice is always free
(01:01:06):
building cool things and and myadvice is always free and if I'm
, if I, if I'm excited enough,I'm going to want to, I'm going
to want to, I'm going to want to, you know, back it up with with
some money, and I'm at a reallyfortunate place right now where
, you know, I can support otherentrepreneurs, which I think is
super cool, and and and I I kindof consider it like planting
seeds, like I want to plantseeds and I want to water them,
(01:01:26):
and that's what I'm really goodat, um, and I'm really good at.
I think I'm really good at umbetting on people Like I.
I I have an intuition aboutpeople and I feel like I'm I I
have a pretty good track recordof of, of betting on the right
people, um, and so that's, youknow, it goes full circle to why
(01:01:50):
I reached out to you originallybecause, like you know, when I
met you, you're an amazingperson.
You're, you know, you're verymodest person, but you know,
you're one of the mostwell-connected people in this
town and so, like there's somany great people here and I
just want to hear what peopleare up to and if somebody needs
support, before some they need acheck and before other people
write a check, like I want totalk to them because I probably
(01:02:18):
will take more risks than otherswill, and part of that is
because there's a littlesomething off with me.
Speaker 1 (01:02:27):
There's quite a lot of things to unwrap here, but
basically, thank you for thekind words.
The respect is mutual.
That's one Second.
The interest the thing that youmentioned about keeping you
interested is very importantbecause I think one of the most
common mistakes entrepreneurs dowhen hiring or when trying to
fish for technical profiles islike oh, they want somebody to
(01:02:49):
produce code or hire engineers.
And it's like well, that is notinteresting.
Most technical people, they'renot driven by money or
aspirations or fame or whatever.
They just want to solve realproblems.
And if the problems are notinteresting, they will not join
your company.
So, and if the company theymight have a short-term problem,
it's okay, but then you willnot keep these people for very
(01:03:12):
long because, like, the interestdissipates over the years.
So, yeah, you raise a reallyinteresting point.
And the other thing that I thinkis really interesting from your
profile as well and that'ssomething that I also share in
my sort of pitch when I'mpitching entrepreneurs where I
want to invest, in whom I wantto invest, is I'm a technical
(01:03:34):
person.
Right, and precisely, there arenot so many CTOs or technical
people investing that can audityour technology, that can vouch
for your architect, or that canhelp you hire a CTO investing
that can audit your technology,that can vouch for your
architect or that can help youhire a CTO that can help you
audit or inspect your API orsort of like figure out
integrations and stuff like that.
So I think that's actually avery good value proposition for
(01:03:56):
an angel investor.
That sort of distinguishes usfrom other profiles.
Before we wrap it up and we'reway over time, but this is
getting very interesting andthis is a signature question of
the podcast is what has beenyour most expensive technical
fuck up so far has to be yours.
We have to own up to it mostexpensive, yeah one big fuck up
(01:04:22):
that he like, oh jeez, it kindof like wiped out production
database or I mean, don't worry,no pressure, somebody set their
office on fire and so you'renot going to top that one
Pressure's off.
Speaker 2 (01:04:35):
Hmm, I gotta think about this one.
I mean, most of my fuck-ups arenot technical.
Most of my fuck-ups are humanfuck-ups.
Speaker 1 (01:04:51):
Okay.
Speaker 2 (01:04:58):
Let's go for that one , and the most kind of issues
I've had in my career, the mostkind of challenges I've had in
my career, are not technicalones, they're people ones and
they're mostly focused aroundjust having high EQ or, in my
(01:05:19):
case early on in my career,having very low EQ.
And so when I was building myfirst company, I really was not
concerned with the human side ofthings.
I was trying to build a greatproduct and I was trying to
build a really successfulcompany, and I didn't really
give a shit about how peoplefelt, or I didn't really care
(01:05:41):
about how people thought aboutme, and I think that created a
lot of issues for me, because,you know, building companies is
a a human endeavor, right?
Like?
I don't care how technical theproduct is or the software is or
(01:06:02):
whether it's quantum computing.
Humans are building thesethings.
These humans need their act,and it took me a long time to
figure this out and I'm stillfiguring it out how to be a more
emotionally intelligent person,how to really understand the
(01:06:28):
lens of the people that areworking with you and working for
you.
That changed everything for me.
So, like, I've never burned anoffice down, I've never deleted
a production database.
But I have, you know, reallykilled some relationships.
I've, I've, I've turned a lotof people off.
I've been a complete asshole.
(01:06:50):
Um, you know, uh and uh it'ssomething that I've worked on
for the last 15 years is reallytrying to be a, uh, more
emotionally intelligent person,a more understanding person and
um, and yeah, I'd, I'd saythat's, that's my, those are my
(01:07:17):
big fuck ups and and and that'sthe stuff that I kind of try and
work on.
Speaker 1 (01:07:21):
Thanks for sharing, thanks for opening up.
You've been extremely generouswith your time and with your
advice.
Any parting words?
I'm rolling out the carpet foryou, so 30 seconds.
How can we help you back?
Speaker 2 (01:07:33):
Yeah, I mean.
I just say, if anybody listensto this pod and is trying to
build some stuff, whether you'rein Barcelona or not, I'd love
to talk to you.
I'd love to share with youanything I can and, like I said,
I'll share with anybody forfree.
I'll tell you my unfilteredthoughts and if you're doing
something really exciting, I'dlove to invest.
Speaker 1 (01:07:57):
And we will see you building something.
If you don't find anybody elsedoing something interesting,
We'll see Charles if you don'tfind anybody else doing
something interesting.
Speaker 2 (01:08:03):
We'll see.
Speaker 1 (01:08:05):
Charles, thank you very much.
Speaker 2 (01:08:06):
Thanks, alex, great to see you Awesome.
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