Episode Transcript
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Kent Lindstrom (00:02):
Hey guys, it's
Kent. Welcome back. Kent
Lindstrom, I, you know, I was soclose Kent, you know, not the
typical name, Silicon Valley,not that big a place. I thought
maybe, hey, I can just go by onename, like staying like, you
know, Kent, the venturecapitalist,
can't do it. There's anotherone. There's at least two of us
(00:23):
in Silicon Valley. He's great,by the way, I should, I'll have
him on some time, and you canmeet him. Kent Lindstrom, I am a
co founder and a partner of theventure capital firm eight bit
capital, that is a seed stageventure firm here in Silicon
Valley, and and I'm the host ofthis podcast, and I think you
kind of like this one. It has,it has a good vibe. Nick
(00:44):
steriality is my guest, and thissort of has a vibe. He's worked
at venture capital for a longtime. Has the vibe of somebody
looking back at and kind ofcalmly reflecting on a career.
Nick is not old. Nick is notdone, but he's worked at seven,
Rosen at Carlisle group atignition, and has just seen a
few cycles. And, you know, as Itake you on this journey through
(01:08):
Silicon Valley and introduce youto some kind of amazing people,
I think you're gonna like, likemeeting Nick here. This is one
for, you know, the real sort ofventure capital wonks. So people
really want to understand howthe market works and how it's
evolved, and how it's faced offagainst different things
happening across the cycle. So Ithink you're going to like it. I
(01:29):
enjoyed my conversation.Appreciate your being here. Next
story alley, my guest today, youall
Nick Sturiale (01:46):
right, welcome
back to something venture
Podcast. I'm Ken Lindstrom. I amyour host, my guest. I should
have asked you to pronounce it.Is it? Nick sterially, am I
saying that? Right? You'resaying Correct. Excellent. Nick
is a partner at ignitionpartners. He's also been a
partner. He's also been an iconventures, seven Rosen funds and
Carlisle group. He's been doingventure capital for a while, and
(02:07):
we'll get into that. But beforethat, was an entrepreneur, which
we'll also get into, and hasinvested in a number of
companies. You'd know Splunk,you'd know bill.com you'd know
reputation.com but has overall,invested something like or his
companies have raised about $180million and returned over a
billion dollars in capital toinvestors, which is, which is
(02:29):
kind of incredible. So you'vehad quite a, quite a career
there.
I've been very lucky. I've beenvery fortunate. Yeah, well, and
I'd say so normally, you know,when I started this podcast, I
thought talking to venturecapitalists and getting their,
you know, their observationsabout what entrepreneurs should
or should not do was actuallynot that interesting, because
(02:50):
most of them had kind ofridiculous ideas, and nobody
wanted to hear that anyway. ButI think you've had such a
amazing group of companiesyou've invested in. You've
invested over such a
as they say, you know, theproblem, interesting period of
time and so many things. Ithought it'd be interesting to
kind of get, get your sense andyour take on the the market
(03:11):
overall. And, you know, thoseare just kind of some incredible
companies. Man, I just think Italked to somebody who
is@bill.com but now, were youthere? How? What phases were you
there? Were you there? I
Unknown (03:21):
was there before it
went public. I was there. I
think we did the Series C, but Iwas on the board for, I forget,
maybe five years,
Nick Sturiale (03:29):
okay, because
they had the incredible thing
when covid hit, right? They werelike, the they were like, a
zoom.com, on the on the billingside, right?
Unknown (03:38):
Yeah. And they like,
you know, I'm sure Renee could.
They went through a ton ofchallenges building that
company, and I would say Bill isa poster child for just grinding
to get it right over many years.And it was not easy, and there
(03:58):
was not a lot of celebritymoments, until the thing really
reached critical mass, and then
Nick Sturiale (04:04):
I wouldn't ask
you about that. As you know, we
we invest from the from the seedstage, so we go on some kind of
interesting journeys. What doyou think is it isn't what do
journeys of companies look likecompared to kind of what people
think they look like? I feellike there's, there's more
companies that you think,build.com you know, up into the
(04:27):
right or chime or UI path, andthen you talk to somebody who's
not, you know, trying to promotethemselves, and they're like,
Well, you know, we invested whennobody else would, and we kind
of written it off. And what arethe you know, you've seen a lot
of companies, what are the pathsthe companies take? Well,
Unknown (04:45):
I mean, the it's almost
bespoke, you know, the part of
the challenges is that
the media and Zeitgeistunderstanding of what's
happening. It. Tends to blot outhow things got to where they are
right now. And it, it sort of itsort of assumes a way the luck
(05:07):
and timing aspect of a lot ofit, and often, what made the
company successful had nothingto do with its original business
plan, their serendipity thereis, I'm not saying these aren't
smart, thoughtful people. Theyare, but they're no one
understands how much of thepercentage is luck and timing
(05:27):
until they're ahead. And I myanalogy is startups are like
Surfers on surfboards all theway, you know, a mile down the
water, 100 yards off the beach,and we're all looking back,
looking for a wave, yeah, and,and you don't know if the waves
coming your way or for it's ahalf a mile down the ocean. And
so that's the challenges, is,Are you part of the that little
(05:50):
group of surfers that get thewave?
Nick Sturiale (05:53):
Yeah, yeah. I had
Eric paleon recently, and he,
he's, he was talking about, youknow, kind of themes like the
sharing economy, or what, youknow, whatever the current thing
is. And he pointed out, and Iguess they've done analysis on
this, but I guess you can kindof think through too that, that
by the time something becomes anidea like the sharing economy,
(06:16):
the iconic company, and in thatcase, it would be Airbnb is
like, eight years old, yes, ofcourse, right? So Airbnb didn't
go, oh, sharing economy. We havean idea. It was, it was there
already
well. And what made Airbnbsuccessful was not what people
think of it today. And you know,it's the old line, alpha lies in
(06:39):
what the conventional wisdomsays that won't work, right? And
the other, you know, greatcliche is most markets are, why
do I need this that moves into,how did I live without it?
Right? And so most generational,iconic companies are market
(07:00):
builders are market makers, andthey convince a constituency to
go from Why do I need this tohow did I live without it? Yeah,
and that's those are the bigones. And so you have to start
with the idea that theentrepreneur the investors, are
almost drunk with optimism inthe face of tremendous
(07:20):
skepticism.
Yeah. And how did you, so, howdid you come into and I'll ask
you more questions about that ina second. But how did you come
into this? You were anentrepreneur, which I, you know,
you can, you know, I've hearddifferent numbers, but people
kind of conflate operator, whichmeans somebody who had a job,
maybe worked at Facebook, withsomebody who started a company,
(07:41):
took money from investors andreturned it, or did not. I think
it's it's less than 10% ofventure capitalists. How did you
come into this industry when youdid from being an entrepreneur?
So I
Unknown (07:52):
will just make it a
short story. So I was at Cal in
99 2000 at the business school.This is when business bank
competitions were the fashion. Istarted a company with two other
guys in a very geeky technicalspace around metrology,
automation. I know that's toosexy for words. And this is when
(08:14):
you know pets.com was happening.Yeah, we entered the business
bank competition. If you couldfog a mirror you could get in.
We ended up winning thecompetition, and there was a
handful of VCs that were judges,and then we took a seed check
from seven rosem, which ended upbecoming my employer. So I ran
that company for a couple ofyears, got a real CEO in to take
(08:35):
over for me, and we ended upselling the company for
172,000,002 and a half yearslater. So when people say, How
do you get into the venturebusiness? I say, Well, the best
way to do it is to make moneyfor your GPS, right, right?
Nick Sturiale (08:51):
That's
incredible. And so you come into
the so why not start a fourth orfifth company versus becoming,
you know, people ask us this allthe time. And you know, being
venture capital is a lovely job,but why did you kind of say,
Hey, I'm gonna I'm gonna investto let other people do the I
Unknown (09:07):
will say this a little
tongue in cheek, but I my
fundamental attitude, what isthe job with the least amount of
effort that pays the most amountof money? And it always looked
to me from afar, like VC wasthat gig, yeah, like it just
felt like they sat in theiroffices with their feet up and,
you know, cashed distributionchecks. Yeah, of course, after I
got into it, I was like, Holyshit, that
Nick Sturiale (09:30):
was what were you
coming to it? And by the way, VC
should never, should neverreally complain about their job
compared to an entrepreneur. Butas you got into it, what did you
learn where you weren't actuallyputting your feet up on the desk
and, yeah, well,
Unknown (09:43):
you know, one is the
feedback cycle is very slow. You
don't know if you're any good atit for 5678, years, it is a it's
a difficult job internally toits own partnership in terms of
getting your deal done andgetting a track record going,
yeah, and then having theability to. To do the important
things as a company goes throughits challenges at the board
(10:05):
level. Meaning, do you replacethe CEO? Do you change the
strategy? How do you influencepeople indirectly? How do you
know when the company's in deeptrouble and you just kind of
park it? There's just a lot ofpattern recognition development
that is hard to do if you're notin it. Yeah.
Nick Sturiale (10:24):
And do you matter
Unknown (10:26):
the cycle you have to
go through? And
Nick Sturiale (10:28):
how do you feel
you are now? You talk to VCs and
like, their big hit was thefirst thing they did, and some
of them it was like the lastthing they did. Do you Do you
feel you were naive and luckyearly on, and now you're, you
know, know exactly what you'redoing, or how did that kind of
evolve over time?
Unknown (10:48):
Well, I wish I had a
good answer to that, because
every Yeah, the problem is, iseveryone is ego and biases get
involved in how they seethemselves in their own
performance. I will my I willsay, I do think venture is a
generational business, becausetechnology goes through platform
shifts. Yep, and older peoplehave a hard time appreciating a
(11:09):
new platform shift. They just donot, saying you can't be good at
it. But most of us becomesuccessful doing a certain thing
and want to repeat that. Andthat's not the way the industry
works, and so a lot of it ishustle, shoe leather, getting
involved in a couple of dealsthat catch the wave, and then
(11:30):
having your own self awarenessabout getting off that platform
and getting on to the next one,and knowing when to do that. And
it's hard because, you know, abull market ingenious get highly
tied together, and so our brainsdon't want to do that. Yeah.
Nick Sturiale (11:50):
So as you think
about the concept of catching a
wave, which is, you know,starting to, maybe starting to
move before the waves developed,why is it so difficult to find
product market fit. Why isproduct market fit so kind of in
retrospect, it's all superobvious, right? And everybody's
Oh, I knew this and I knew that,but at the time, it's not that
(12:14):
obvious. Yeah,
Unknown (12:15):
I think you could spend
your next 10 podcasts on finding
PMF, and you still would barelyscratch the surface. I will say,
after 25 years and 100 startups,I think the one thing I regret
not studying in college wasbehavioral psychology. I think
when you for example, you knowJeff Jeffrey Moore wrote
(12:40):
Crossing the Chasm, which is,you know, an iconic idea
embedded in that, though thatdoesn't really come out is the
chasm is really about trust.There's a trust chasm, right?
And when you think about ourbiases, whether we're the
entrepreneur selling theirproduct, or the customer's
biases looking at the product.There's, like, a bunch of things
(13:03):
going on. So on the on our side,on the vendor side, we have two
fundamental biases. One iscursive knowledge. We are
intimately familiar with ourproduct, which means we tend to
overvalue its capabilities andundervalue its limitations.
Because it's our baby, you know,we think our baby's a prodigy,
and we don't see the limitationsand and then the other thing is
(13:27):
what I would call the empathygap, meaning we don't walk in
the customer's shoes. We don'tsee what they see. They only
care about themselves, not aboutus, and they might not even use
the product the way we intended,and then they blame us for pile
air, right? So those two thingson our side are serious,
(13:50):
eyesight, line of sight issuesabout seeing where the demand
is, yeah. And then on the otherside you got, there's four
fundamental biases on thecustomer side. One is reactants,
risk, fear, meaning, you know,do I have something to lose? If
I do, I'm going to move veryslowly. If I have nothing to
lose, I might move fast. You'vegot skepticism. Doesn't my other
(14:14):
vendor do this already? Ithought they already did this
inertia, which is a verypowerful thing, which is, I'm
busy. I don't have time to dothis. And then lastly, I think a
big one, is hyperbolicdiscounting. Our brain perceives
value based on how fast thereward of the punishment
(14:36):
happens, meaning, if we get thereward immediately, we value it
massively. If it takes threemonths to get the reward, we
discount the value massively.Same thing on the punishment
side.
Nick Sturiale (14:47):
Yeah, yeah. It's
interesting. You know, I worked
with at one point James curryand San jaski, who, you know,
started NFX, the venture firm.And one of the things that Stan
always said, you know, form ofthat was. Like, when you the
people would create theseproducts, like, kind of consumer
products that were better, youknow, like, kind of better,
(15:08):
like, Hey, this is better thanevite. And he was like, Look,
your thing has got to be 10times better than the other
thing, and 10 times easier.Like, if you want to compete
with a dating site, you need tofind your spouse on it in a
minute, like if you want to beatbeat the incumbent, basically, I
Unknown (15:28):
totally agree. But you
know, the reality is, the one of
that product ain't going to be10 times better, right? You just
it's not realistic. And so thequestion becomes, is there
something, you know, narrowinside of that, that could be
more convenient faster? Is theresome you can't? You got to learn
how to walk before you jog. Andso that's the question is, can
(15:50):
you get a half baked product tohit a convenience value prop
fast? Yeah.
Nick Sturiale (15:57):
And so, how do
you, so an entrepreneur, how do
you parse, you know, it's easyfrom the outside, or you read
the book, and here's how you doit. But how do you know what an
entrepreneur and how does anentrepreneur know when they're
being I feel like this under thepeople started pivoting and
moving off of things quickerthan they used to. On the one
hand, on the other hand, thereis a point where you perceive
(16:20):
just persisting on somethingthat nobody needs. You're
persisting on the, you know,podcast app when, you know,
Apple's got the free podcastingapp and, oh boy, maybe it's time
to move on, right? Yeah,
Unknown (16:34):
that's, you know,
again, it comes back to biases
and behavior. We're optimists.We have a hard time with sunk
cost letting go, you know. Sowe're all replete as human
beings. We are just replete withthis sort of emotional whipsaw
for ourselves. And it shows upin that, I think, on the when do
(16:57):
you know it is hard becausethere's a delay, there's
asymptomatic feedback, right?You do something, it might take
three or four months for thefeedback to really show up,
saying, was that the rightchange of the product or but I
do think, you know, my dad, whenI was growing up, used to say,
watch what they do, not whatthey say, Yeah, which always
(17:19):
stuck with me. And if they areusing something, even if it's
half baked, that tells you alot. If they keep asking for
something and they don't doanything, you know, you don't,
you're you're off, yeah. Sowatch their movement towards the
product, their use of it, theirengagement level, if they churn
out how fast there are proxiesout there.
Nick Sturiale (17:40):
Yeah, it's
interesting. My partner,
Jonathan Abrams, has startedseveral companies where the
product became popular, and healways pointed out that he'd
have some hey, here's my newthing, you know, consumer thing.
Do you want to try it? And allof his friends were like, Oh, I
love it. I love it. I use itevery day. And he's like, do
they know that I can just lookat the database I know who's
using it and who's not. And soas he built companies, when
(18:01):
people said they were usingnever touch, he's like, that's a
loser. But when he looked andthey were actually coming in
every day, twice, in thedatabase and not telling, was
like, okay, that might be Yeah,that might be a thing.
Unknown (18:13):
I think, yeah, the big
one too. And I wrote a blog
about this recently, I wouldsay, if there's one profound
shortcoming of Silicon Valley iswe're bad at listening. And I
mean listening to understand. Wego into new prospects and we
just aren't selling, yep, and wedon't listen. Look at at body
(18:34):
language tells try to reallyobserve what their reaction is.
We just keep talking until wehope we hit something that they
like, yeah? And so we miss allof the I don't care, signal,
yeah.
Nick Sturiale (18:50):
And you kind of
need a product to do that,
though, don't you like? Becausewe have people kind of ideate
where they're like, I'm justgonna go interview a bunch of
people. Yeah. And that seemslike it's a little too even if
you listen carefully, it's alittle too abstract.
Unknown (19:02):
I It is abstract, but I
think you can. There are ways of
asking empathic questions thatdon't say really what matters to
you. You know, like, if, if youcould change two things about
your job today? What? What wouldyou do? You get your you get you
stop selling and you startasking. I'm not saying you do
have to get a product in frontof them, because then you'll get
the rest of the revealedpreferences. Yeah, but you have
(19:22):
to start with the idea that yourperception of their problem and
their perception of the problemmight
Nick Sturiale (19:27):
be different,
yeah. So advice to an
entrepreneur, so you've come,you've been on a lot of boards,
so you know, companies doingwell enough to get your get your
capital, and now you've got aboard, and I've we've
experienced this to detriment.Frankly, you've got five people
on the board Who all thinkthey're pretty smart. You've
been an entrepreneur. Somebodyelse worked at McKinsey,
(19:49):
somebody else worked at everyonethinks they're smart. And here
you are, and you've never run acompany before. And you look to,
you know, we did this, we wereyoung entrepreneurs. You look.
To your board. You say, Well,you don't ask for advice, but
you get it right. So how shouldan entrepreneur sort of think
(20:09):
about an, you know, an esteemed,successful venture capitalist,
giving them advice?
Unknown (20:16):
Yeah, it's a
challenging one, because you
want to be diplomatic about it,but you also need to parse good
advice from Mike Maples. He'scalled it rock fetching, which
is you should go do this and yourun and get a rock and bring it
back. And it was an absolutewaste of time, right? And so
(20:37):
discerning rock fetching advicefrom, hey, I'm telling you. I'm
telling you something that'sgoing to happen to you in six
months. You might want to justthink about this, right?
Nick Sturiale (20:51):
No, no, I was
gonna say, so you're in a board
meeting. And, you know, peopleare, you know, somebody just got
back from a conference, and sowhat's our China strategy? And
someone else wants a differentconference. What's our mobile
strategy? You know, that's
Unknown (21:05):
our Gen AI strategy.
Yeah, right,
Nick Sturiale (21:07):
whatever it is
today, exactly. Yeah.
Unknown (21:10):
I think you gotta you
tell me more. And then you also
have to say, Look, everythinghas a trade off. Everything has
an opportunity cost. If you wantme to go do this, what do you
want me to stop doing? Yeah, andso don't let them just, you
know, throw out 30,000 footideas that are not practical.
And, you know, force them intothe what do you want me to not
(21:34):
do? Yeah, like, limitedresources I got, I'm under huge
time constraint, and just bringthem in to the decision, don't
let them just throw out uselesson mods.
Nick Sturiale (21:46):
Yeah, it's
interesting. And how, I mean, is
this a reason? Maybe that asecond time entrepreneur has an
advantage, because that's allgreat. But you know, when you
know whoever it is, you know,Doug Leone is saying, Hey, I
think this is a good idea. Youknow, it's a special guy to go,
I don't know.
Unknown (22:05):
Well, at the end of the
day, you know 100 times more
about the business than theboard does you. The board is
three chapters behind. Yes, theyhave pattern recognition. Yes,
they're another company, so theycan provide contextual
observation. But at the end ofthe day, you're in the account,
you're talking to the customeryou're looking at their face,
you have way more knowledge thanthey do, so you help them
(22:27):
understand what they don't seewhen they're offering advice.
That is, it's just maybe it'snot the right time, or it's just
not contextually relevant.
Nick Sturiale (22:37):
Yeah, is there a
form of advice that a VC should
be and by the way, I've heardvery prominent you would know
them, venture capitalists saythat 80% of the advice from
venture is a little provocative,but 80% of the advice from
venture capitalists is damaging.Rock fetching 15% is probably
neutral, and 5% is helpful. Whatdo you think?
Unknown (22:57):
I always want to what
I'd ask Kent is, what percent
was your advice? Was your advicewas that in the 5% of
Nick Sturiale (23:02):
the 80% that's
always five, yeah, of course,
Unknown (23:05):
everybody is above
average in their own
calculation. Yeah. I thinkthere's a lot of truth to that
statement. You know, the thehardest part is they do have
pattern recognition. A lot ofthem do. I always feel like a
(23:27):
VC, in some respects, is likesomeone who is becoming an MD
and is interning in thehospital. The reason why they're
up for 48 hours is they'rewatching a cycle of sickness to
health, and they're seeing thatcycle, and that does become a
useful thing around startupsplacing bets, because they see
sickness to health cycles. Andso there's value there, yeah,
(23:48):
and that's what you're payingfor. But there are a lot of,
let's call them dilettantes,that never ran a company, never
did a startup, never met apayroll, never had to ship a 1.0
release on what you should do,and you have to politely say
thank you and then disregardthem.
Nick Sturiale (24:05):
Yeah, that seems
to be the big one that we saw
where, you know, kind of laying,you know, sometimes you have to
do it, but like, laying offpeople was just a really, you
know, Do this, do that is a verysort of flip, non em fat and not
empathy, which learn English,you know, not empathy for like,
hey, that's, we know it's prettytough, but you've got to do
(24:27):
that. And, you know, so if weneed to take another cycle to
make sure it's the right thingto do, you know, let's take that
cycle, or whatever it is,suppose, like, oh, you know, I'm
playing, you know, successionand deck cut this guy, that guy
sucks and you know, it's easy inthe boardroom, right?
Unknown (24:43):
Yes, you don't, you
don't have to do the dirty deed.
You know, on the other hand,entrepreneurs were all victims
of our optimism. Sometimes fallon to an OPEX for too long when
they know they should havewhacked it six months ago. Yeah.
You know, hope is a strategy. 80that permeates a lot of business
plans. That's right. And sosometimes there's the hard thing
(25:06):
about hard things. And yeah, butI think you you force a board
member who's giving you adviceto clarify their advice, right?
I
Nick Sturiale (25:18):
think that makes
sense too. I think also one
thing that that's helped meWell, now that I am a venture
capitalist, I understand that,is kind of try to understand
where you fit into that person'slife, because you're not their
only company, yes. And so youkind of have to think to
yourself, Okay, am I thisperson's most important company?
Meaning, maybe they're reallythinking about this advice or
(25:39):
not, or am I not this person'smost important company? And they
came up with that idea. Withthat idea about four minutes
into the board meeting. And youknow, if I push back, they'll be
like, Oh yeah, you're right.
Unknown (25:49):
My old partner, Steve
Dow, when I was a seven rows and
said this, and always stuck inmy head is you have to measure
the time delay between when yousuggest an idea to a CEO and the
CEO thinks it's their idea,because CEOs don't really make
moves until they think it'stheir idea. And so a lot of what
a board member should do is bean indirect influencer. You ask
(26:11):
the question that shines thelight on the issue and forces
the CEO to revisit anassumption. Yeah, that's
interesting. That's being aneffective board member is not
opining, but asking a very wellplaced question that sort of
stops the discussion.
Nick Sturiale (26:32):
Is there a
category where a board member or
venture capitalist mightactually have generally good
advice, and I think of likefundraising, for example, where
you know, why would anentrepreneur know? And you might
be able to say to Ron for Hey, Iknow what you're doing is great,
but nobody's going to beinterested in this. Because,
right now, nobody cares about
Unknown (26:50):
this topic, or not a
debt company, right? Yeah,
right.
Nick Sturiale (26:53):
Or, you know,
hey, four months isn't really
enough to raise your next round.And you know those types of
advice, yes, yeah. I
Unknown (27:01):
think that's an obvious
one, where operating ideas might
have been bad, but their adviceon a round will be very good,
because they're living in it,right? All their portfolios
going through financing and so,and there is a lot of value in
the currency of what's gettingraised and why? Yeah. So
Nick Sturiale (27:20):
I'm interested in
the role of the CEO, founder,
CEO, as they go through thephases. Because we come in at
the seed stage. And, you know,people are doing what they do at
the seed stage, which isanything they can to survive and
get to the a stage with four orfive people, which is the, you
know, whatever the managementchallenge of four or five people
is, how do you, how do you seethe role of and by the way,
(27:43):
there was a shift, you know,used to be that, you know, the
startup guy would kind of getthe company to a certain place,
and he'd fire that guy and bringin the, you know, quote, real
CEO that, you know, Andreessen,kind of changed that a little
bit. Or a lot of venture firmsfirst round kind of came in and
said, hey, you know, we'refounder first, and the founder
should go the whole way. But ina world where you believe, maybe
(28:04):
you don't believe it, that thefounder should go the whole way,
how is the role changing from aseed stage investment to a
series a investment to, youknow, Series B investment?
Unknown (28:14):
Yeah, I would. This is
the hardest question. Because on
the one hand, a founder, CEO,that goes the distance the
returns to the investor are offthe charts. So it's not as
though investors look and say,Oh, we're just going to bring in
somebody. As soon as you get toa stage, there's, there's no
reason do that. And by the way,most boards are very passive.
(28:36):
Hate making a change, often dragtheir feet. But on the other
hand, you know this, and being aCEO is an incredible breadth and
depth of skills and the demandson the role change as the
company stage changes. And sowhat made you good as a seed CEO
is irrelevant for the one forthe product market fit stage.
(29:00):
And so that's the challenges,does the person that was, let's
call it, the technology pioneer,does do they really understand
how to commercialize and alsostart to build an organization
where they're not the heroanymore? I call it. Can you go
from, if you're piloting aplane, are you flying by side?
Are you flying by instrument?Right? And and often, though,
(29:23):
those people have troublemorphing into that, you know,
they still want to fly by siteand see everything and touch
everything, and you can, ifyou're 100 people,
Nick Sturiale (29:32):
yeah, yeah. My
understanding is the Google guys
had a conversation at somepoint, I think maybe with John
Doar, where they were going totry to do it themselves. And he
was like, Well,
Unknown (29:44):
my CEOs and see if you
think you're that. Yeah,
exactly. Well, that seemsMcNeely and I talked to a bunch
of others, and they came backand said, Cal, you're right.
Nick Sturiale (29:53):
That does seem to
be the method. And boy boards
can bring in terrible executiveswho you. Have the skill set of
being good at getting boards tobring them in, but they can also
introduce you to people whereyou think you're doing marketing
pretty well, and you meetsomebody, you're like, oh, oh,
that's what a good person'slike,
Unknown (30:11):
well and but the hard
person is, and I'm guilty of
this too. We've brought we'vebrought in CEOs that were
disasters. Yeah, you know thatwe thought were good, and for
whatever reason, they were a badfit. And so we in the category
of making things worse. We did,yeah? So it's, it's, it's never
obvious and it's neverfoolproof, yeah, you know, but
(30:35):
LPS pay us for speed, you know?They want to get put the money
on they want it back faster,right? So we do have an
obligation. We have anobligation of urgency, not just
to sit back and hope
Nick Sturiale (30:47):
that's right.
Yeah. I mean, the thing that
I've experienced was sort ofpeople who are in famous, you
know, famous company executive,right, who has seen a lot of
growth and when, like, it isreally good at getting the
reason they're in that job isthey're good at getting that
job, and they're good in a room.They go talk to the board, oh my
gosh, this guy's so impressive.And they show up at your
(31:09):
startup, and they're like, youknow, they can't do anything for
less than $600,000 a year, andthey can't do anything with less
than 20 people and an executiveassistant. And a year later, you
know, the entrepreneurs, like,did that guy actually grow
Google? Or was Google justgrowing and they figured out how
to get a job at Google?
Unknown (31:27):
Yeah. So that is, the
other issue is, were you the
cause, or were you there, right?And I have had you, we've both
had that experience. You hire,let's call it the celebrity. It
turns out to be a diva, right?And and really doesn't want to
do the work, wants to be amonarch, yeah,
Nick Sturiale (31:48):
yeah, that's
right. And by the way, that
works, that works in SiliconValley, if you sort of hop from
one company to another, whereyou can sort of, you know, you
go from Yahoo to Google toFacebook to Uber, and, you know,
you're the kind of AssistantGeneral Counsel, and, you know,
like you got the resume, it justbuilds on itself. But, you know,
(32:10):
then you go to a startup andyou're like, What the hell is
this? What
Unknown (32:13):
they're, they're
absolutely, like a fish out of
water. They don't know how tofind product market fit. They
really don't know how to scalethe org. They're, you know,
they're just, they're designed,and also they know how to spend
money. They're really good atthat. Oh, boy, yeah, that is the
hard part about just hiring aCEO as an alchemy in and of
Nick Sturiale (32:35):
itself. Yeah,
yeah. I've seen more success
with kind of interesting CEO,you know, where you sort of hire
somebody who failed at a similarcompany, but boy, they were, it
was just there was, youunderstand why they failed, and
there's a chip on theirshoulder, and they're like, I'm
not, you know, it's like they'veplayed level two of the game
once before, and they're like,I'm not opening that door this
(32:56):
time. And, you know, they takeyou to level three, yeah.
Unknown (32:59):
And again, it comes
back to success is still a
function of, you're on thesurfboard and the wave came,
yeah? And you don't have controlover where the wave came, and so
people presume that they werewave generators, yeah,
Nick Sturiale (33:13):
right. Well, you
know, let me wrap up a little
bit as you kind of look acrossthis sort of career of, you
know, this market crash andbanks failing, and all, you
know, all the different thingsthat have happened. And, you
know, venture changing, I thinkmost notably, there being a lot
of new entrants into into thebusiness. How do you think it's
changed better for worse overtime?
Unknown (33:37):
It's May I was better
and worse. Always an IB holder.
I think it's, it's hard tofathom, if you've been in the
Valley for 30 years, it isreally hard to fathom what it
was like 30 years ago versustoday. Yeah, it just is. It's, I
would what I would say is thattechnology now is the base
(33:57):
industry of the United Statesand of the world, and the valley
is the epicenter of it, and ithappened in the last 30 years. I
mean, look at the top fivemarket cap companies. Yeah, 40
Scotland. So it is when you livein it you can't see how big the
trees have become, yeah, andwhere they were. And so I would
say the biggest thing, and thisis maybe looks to the Gen AI
(34:20):
startups, the big mistake thatstill happens is that technology
hysteria generates a flashcrowd, which generates
investors. And what isn't beingdone well is figuring out how to
make it commercially relevant toa business, user or consumer.
And so there's a lot of becauseit's Gen AI, it's by definition,
(34:42):
good, yeah, and that's justnobody cares whether it's Gen AI
or ml or behavioral datascience. All they care about is
whether it makes their lifeeasier faster, whether it
advances their career or getsthem from not being yelled at,
right? And so people have.Startup entrepreneurs had better
understand, how do I translatethis into what the customer
(35:06):
actually cares about? Yeah?
Nick Sturiale (35:09):
Yeah. I think
that's right. I use the example
in mobile when, you know, kindof the iPhone came out and you
could do payment and geolocationon the phone, and there was an
app called Foursquare where youkind of check in, you become the
mayor of a place. And they werelike, What do you know? That
idea came from? What do you dowith this technology? I can
locate something. And then youhad Uber, where somebody just
(35:30):
started with, like, I can't geta cab. Yes. How can I? Oh,
shoot, there's this technologyhere I can use, and I think with
generative AI. My guess it withAI in general. My guess is the
big companies outside of theplatform infrastructure, things
will be people say, I'm tryingto solve this problem. I
couldn't solve it for oh, now Ican solve it in healthcare or in
(35:51):
FinTech or in, you know,whatever they're focused on.
Unknown (35:54):
I ask entrepreneurs.
Tell me, don't tell me what the
what's under the hood. Tell mewhat I can do today that I
couldn't do yesterday? Yeah? Andthey struggled to answer that
question. Yeah. Oh yeah. Thereis, there is the gap you have to
figure out. Yeah.
Nick Sturiale (36:12):
Well, for us,
that was all of web three. You
know what? I could put mymortgage on the blockchain.
Yeah. Never knew. Awesome. Neverknew I wanted that, but
apparently it's
Unknown (36:23):
a solution in search of
a problem. And and because of
the scale of the ventureindustry and scale of the
valley, you got a lot morecandidates chasing the same sort
of mysterious notion of whatthey should be, yeah,
Nick Sturiale (36:38):
and well, and
what do you make of the kind of,
it's been interesting that whenI started, well as an
entrepreneur, they're kind ofventure capital stars. It was
guys like John Doar, Mike Moritzor whatever. And now we kind of
have a different kind of, it'skind of evolved. It's
interesting. You've got, like, Iguess, on the young side,
somebody like Harry Stebbingswith a podcast, or, you know,
(36:59):
David Sacks, who's become famousfor having a podcast his
political views. What do youkind of make of that? Yeah, Reid
Hoffman in the middle sort ofthing. Yeah.
Unknown (37:11):
So I The problem is I
will sound like a crotchety old
man, get off my lawn when I saythis. Right? I think it's very
dangerous to become apersonality or a media thing.
Because what happens is youstart to act like the thing that
keeps you, keeps your attentionas a media thing, and that is
(37:32):
separate from being an investor.And so you start to perform as a
media person instead of being aninvestor. And those are two
different things. Yeah, on CNBChas not a thing to do with
actually, astute investing,right? And that's the that's the
(37:54):
trap.
Nick Sturiale (37:54):
Yeah, it's, I
find it wildly entertaining
though.
Unknown (37:59):
Yeah, it is. You just
don't want to be like, You got
to jump on a topic and then ownit to be, to be in the
zeitgeist. But that really islittle to do with, like, I
believe a big backlash is comingon. Gen, AI, right? But these
people that, but to talk, youhave to talk about it if you're
going to be on podcasts.
Nick Sturiale (38:18):
Yeah, and the bad
and the backlash being what that
AI is not a real thing, or thatwe're going to go
Unknown (38:26):
through. It turns out
it's really hard. It has
hallucinations. Yeah, debuggingthe hallucination causes other
hallucinations. And so yes,there's going to be huge impact.
And yes, it is coming, but it'snot going to, we're going to,
we've over forecasted the shortrun, and we've under forecasted
the long run, and we're about togo into this cognitive
(38:48):
dissonance of over forecastingthe short run. Yeah,
Nick Sturiale (38:51):
I think that's
right. I've been around for, you
know, different technologyemergence, like the, you know,
the emergence of the Internet,and it was, I mean, not the
emergency, the emergence of whenyou might use the internet, like
around mosaic, and you use it,you're like, this, I don't know
what's gonna happen, but thisisn't, this is something. This
is like, it's incredible. I'mlogging into servers in other
countries, incredible. And withGen AI, like, I do the Google
(39:15):
search, and the Gen AI kind ofgives me a fine answer. I think
when I search for myself, Ifounded Airbnb or something like
that, which not accurate. So, sothere's that, like, it doesn't
blow me away that
Unknown (39:28):
way, we're just gonna,
we're gonna go through the drop
of disillusionment and then comeout of it. It's just that we've
got 3000 companies and atrillion dollars chasing it
right now. Yeah, that's right,expecting a 24 month ROI, yeah,
disappointed, yeah, right now,the reason it's the picks and
shovels, it's Nvidia, yeah,it's, you know, it's, it's the
guys building theinfrastructure. Yeah, they're,
(39:50):
they're consultants. They'regetting the money.
Nick Sturiale (39:52):
Yeah, good Lord,
we should have all this invested
in Nvidia. Like, yeah, why gothrough all this? So, so this
is, this is fantastic. What doyou as you kind. Of look
forward. What are you kind oflooking forward to in the world
of, you know, investing orstartups, or what do you what do
you kind of see in the futurehere?
Unknown (40:08):
Wow, it's so hard.
Because, you know, at my age, I
struggle with, it's kind of a01, thing you you either in the
business, you are hostile whenyou were there, are you're
toast. You can't do a point fiveeffort, and startups, you will
get crushed. And so the hardpart about doing what we do is
(40:31):
it's an all in gig, yeah, andit's hard to sort of and, but
there's a 23 year old gen AIentrepreneur. Want to listen to
a 60 year old VCs. They're onmultiple times. Probably not,
Nick Sturiale (40:44):
yeah. Well,
there's, it seems like there's a
lot of VCs who do point five it,though, because the way the
economics of the thing work,and, you know, the legacy, and
they've been around and, youknow, I mean, you know,
benchmarks got it set up acertain way. I think at
ignition, you guys have it setup a certain way. But some
people have it set up so you canhang around for a long time.
Unknown (41:05):
And I would submit that
there are a handful of VCs that
do very well in their 50s and60s, but generally their crime
is behind them. Just because ofthe way you operated when you
were 30 is so different thanwhen you've made some money and
you have a name and you know,you think you've got a an
(41:29):
efficiency model. Yeah, itreally is about shoe leather and
hustle and being outfield, yeah.
Nick Sturiale (41:36):
Well, stay tuned.
So how do people like you know
you've you've written blogs andyou have thoughts and things
like that. How would peoplefollow your your thinking in
this world, LinkedIn or Twitteror you?
Unknown (41:47):
Yeah, I mean, I, I've
posted a few things. I'm not a
prodigious writer. I'm becauseI'm at the end stage of my
career. I'm starting to writesome stuff down, just because
you do get scar tissue patternrecognition after doing it for
25 years, and often people arevery careful about what they
say, because they're trying toraise a new fund or do a new
deal. And I don't have thatproblem anymore, so I'll start
(42:11):
posting some stuff, but most ofmine, it goes back to what have
I learned? And it is. It's aboutour brain. Yeah, and
understanding how our brainoperates is a really important
insight into building a story.Yeah? All
Nick Sturiale (42:26):
right. Well,
thanks so much for doing this.
Thanks
Unknown (42:28):
Kent, yeah. All right.
Nick Sturiale (42:30):
Nick story alley
has been my guest. Something
about your podcast. Talk to youNext time
Unknown (42:42):
you