Episode Transcript
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Speaker 1 (00:01):
This is the Startup Sales Safe podcast.
Speaker 2 (00:03):
Thank you for junion you as a favor like, subscribe
on YouTube or LinkedIn, and be sure to give us
your feedback. Hope you enjoyed this episode. Hello everyone, thanks
for joining us today. Welcome to a brand new episode
of Startups. They'll say, as always, I'm your host, Anthony Prakash,
and today I am joined by a very special guest,
Ernest Sweat. He's joining me from not too far from
(00:26):
here in the Bay Area. We'll jump into why Ernest
is here, his mission, and what he is doing very shortly,
but before that, I wanted to welcome you all to
the twenty fifth edition of Startups. They'll say, it's this
very special episode, and I'm so glad that Ernest has
agreed to be as a guest on this particular podcast.
I also want to thank all of my previous guests
(00:47):
we've been on this podcast. It's almost ten months since
I started this and little did I imagine I'll get
to a twenty fifth episode. So thanks to all of
you for your tremendous support. That Ernest welcome to Startups.
We'll say, thank you.
Speaker 1 (01:00):
For having me, Anthony. I am honored to be your
twenty fifth guest, and as a fellow podcaster, I think
people outside of podcasting world don't understand how big of
an achievement that is. Like it's I can't remember what
the stat is, but I believe around ninety percent of
podcast phil Or they stop cease to make a new
episode after episode ten. So you've already you're in rare air.
(01:23):
But it's about consistency and keep going.
Speaker 2 (01:25):
Yeah, thank you for that. Honest, I didn't know that statistic.
I mean, you know, for me, it's just been so
much fun doing this and just getting to learn from
people like you. So why don't we just start with
a little bit of background in your own words about yourself?
You know whatether, I know you wear a variety of hats.
The number of hats I can't even imagine. But maybe
you just talk to people about currently. I know, literally
(01:48):
you're wearing one, but I mean, in honesty, you're wearing
so many others. Why don't you just tell us a
little bit about yourself? Yeah?
Speaker 1 (01:55):
Yeah, So I grew up in Little Rock, Arkansas. I
start there because I built a lot of kind of
values and approach to life that I have not just
because of the place, but more importantly, like my two
pillars on my parents. And so my father was a
computer compsigrad who then went to work for the state
and be the director of it for their workforce development agency.
(02:19):
And on top of that people talk about the hats
that I wear. He was also a full time pastor,
so that whole like, you know, being able to balance
an act and you can be a full person even
though as humans we always try to like box people
in just so we can take on all the information.
He was living proof of that and inspiration. And then
my mother who in our own right just like phenomenal person.
(02:40):
She has always been an educator, and so she taught
in public schools and Little Rock for about forty years,
half of that being in Pe. And then around when
I started going to high school about to go to college,
she went back to school and then became a science
teacher in middle school. And so they those careers choices
of theirs really put it imprint on me and my
(03:00):
sister is like, you want something where you can earn
a living but also be able to constantly feed your
desire to learn, which they had to do in their careers.
And then the cherry on top is if you can
find something where you're using those learnings to literally invest
in other people's success. And so they did that as teachers, preachers,
government workers. And when I actually found Venture, I was like,
(03:24):
all right, this is like a through line to kind
of what our sweat mantra is.
Speaker 2 (03:28):
Beautiful story. I mean, it's amazing how many of us
get so inspired by our parents. A lot of people,
I mean even my friends. You know their dads, the doctors,
they end up being a doctor. The mom's a teacher,
they end up being a teacher or a nurse. I
mean during our childhood we don't realize it, but over
a period of time, I mean we realize that it's
in our DNA, that's our mission in life as well.
(03:50):
I mean, so beautiful story. They're honest since little Rock
and you know your college and I've seen that you've
been a consultant in a financial services firm. You were
a founder by yourself, and what you're trying to do
to pave the way for the next generation of founders.
So I know it's a long and arduous journey. I'm
(04:12):
sure right. I mean, you've had a fun, a lot
of fun along the way to realize saying Okay, I'm ernest.
This is my mission in life to go help the
next generation of founders do my own fund. If you
will talk to us a little bit about you know,
how did you come to the realization that this is
what was your calling at least from a professional perspective
(04:32):
from where you were. I mean, you obviously took your
first job. I guess that came right out of college
where you were just tell us a little bit about that.
Speaker 1 (04:40):
Yeah, Like most people, I like finding your and I
put them one in the same. I think your vocation
can be a purpose in calling that helps be kind
of the catalyst to other things that you're passionate about,
or your influence or even just your responsibility as somebody
with talent, time and resources. And so for me finding venture,
(05:01):
it wasn't until of all places, New Delhi, India, where
I found I was like, oh, this is what I
want to do for the rest of my life. So
to not bury the lead. Had experience as an equity
research analyst, then a failed founder in the world of
kind of like future of work in at tech and
that experience in Sunsetting that that company led me to
(05:22):
go to a business school at Kellogg in the Chicago
Land area, and I had every intention kind of to
either kick the can down the road and just be
like a management consultant, or if I was lucky to
find a you know, startup, to be the first, second
or third business hire for them. And I came across
(05:43):
this opportunity through Kellogg to work at an international venture
firm and be placed there for the summer, and so
I applied, I got in, and I was placed in
New Delhi for an organization called Central Square, which I
had a venture firm under the Umbrella organ and I
got placed in New Delhi, India. And so that experience,
(06:04):
despite in the summer it being one hundred and seventeen
degrees fahrenheit, you know, it was a blast. I loved it.
I saw how I could take my experience from equity
research and apply it to the private markets and just
the things everything I've been missing in other career stops.
It answered right. Having the ability to talk to a
(06:26):
ton of people, having the ability to thesis, build and
then putting skin in the game. Had everything that I wanted.
And so that's what really motivated me not to had
every intention to move back to New York after business school.
But that gave me the inspiration. I was like, hey,
maybe I should probably look out to the Bay Area.
So that's what brought me out to the Bay. It
made me kind of like zero in to venture got it.
Speaker 2 (06:48):
Got it along the way said and I said, you
were a failed founder as well, I'm pretty sure you
maybe think about it, learnings from it, whatnot. And then
I mean, you obviously to a lot of founders today,
whether it's just to consult with them or as part
of your VC role, if you're well, what are the
sort of learnings that you got being a founder that
(07:12):
I mean might have formed your principles on? Okam, I mean,
here are some of the pain points founders go through.
How can I help circumnavigate some of those things? And
you know, in today's world.
Speaker 1 (07:22):
And then it's a great question because one thing I
look for I've always looked for, but I'm really looking
for now in founders is their ability and their team's
ability to have learning velocity. And what I mean from
that is like when they get information from the market
that might be a hidden insight, or whether they get
like smacked in the face from competition or a mistake
(07:44):
with a customer, they're able to take that learning and
quickly iterate on it to then get escape velocity as
fast about and so being able to always take information
figure out what to do next move I needed to
apply in my own life as well. So yeah, without
that framework in mind, I came across it. But when
(08:06):
it looks back at like, hey, my company failed because
I picked a really tough go to market motion, trying
to sell through universities or through municipalities. And second kind
of like a compounding mistake together is if you're going
to choose that path, you need to have advisors who
can help you skip steps. And I didn't do that.
(08:28):
And so ironically enough, as I became a venture capitalist
and joined a corporate VC out here is my first
kind of stint as a full time venture capitalist. I
really got good at like helping companies with go to market,
helping companies find the advisors that could help them find
strategic partners or customers, And yeah, I just leveraged the
(08:49):
hell out of my opportunity working at a large real
estate company that was in the intersection of logistics and
real estate and commerce, and not just leverage at brands,
but really ug in and got my own relationships through
that organization that could help my portfolio companies and help
companies that weren't even my portfolio companies but were from
founders that I respected or that I was trying to
(09:10):
convince to take my money.
Speaker 2 (09:12):
Got it? Yeah, beautiful. I mean as to how little
little things in life impact us in the long run.
And then you know, you think back and saying, I
had that aha moment from when I was a founder.
You know, how do I ensure that these ten people
ahead of me who are taking my money and my
you know, people who are investing in me, you know,
applied the right way? So as as a would would
(09:33):
you call it? You would call yourself a VC right
now even though you're looking forward to building stress would.
Speaker 1 (09:40):
Yeah, I'm still I'm still investing right now?
Speaker 2 (09:43):
Yeah? Yeah, perfect. Yeah. So so we'll talk about stress
would in a in a little bit and your vision
for that and everything. But when you invest in a startup,
if you will honest right, I mean, how much of
it is pure research numbers and what I mean, the
tim and the projections and whatnot versus your gut feel
(10:04):
as a person you know, with whom you're talking to
sitting on the other side of the table. I mean,
do you give that any any weight as it all
from just your individual perspective.
Speaker 1 (10:13):
Yes, it's an asset class that is more of a
balance between science and art than others. And based on
how early you're invested, it's going to be more art
than science. And because there aren't any real numbers to
dig into, it's just assumptions. Yeah, and so for me,
because I'm a Series A and Series B investor, there's
(10:35):
a little bit more data. But what you're trying to
determine is like what's repeatable and what has the opportunity
to actually have what you're underwriting against this, Does this
team have the opportunity to do something special and unique
and have a venture backable exit and so a lot
of that, and this is even before you join the board.
(10:56):
Invest A lot of that is determining is like, hey,
do you know, I see these numbers, Like, all right,
what have you learned? What's the learning velocity there? Like
what have you learned? What are you going to exploit
because of that? What's going on in the market that
might influence you? How's that going to you know, contribute
or restrict your product? Roadmap. But then the other piece
(11:18):
is just like who are you as a person, what
motivates you? What does success look like for you? And
then how have you been able to do those things
I wasn't able to do as a founder, but like
build a strong team around you of both employees and
advisors that give you a competitive advantage, and that really
speaks to today's time and opportunity.
Speaker 2 (11:39):
Right.
Speaker 1 (11:41):
Your question, Anthony in the beginning kind of like felt
like it was a great question and normal question, but
what underline is like, hey, what frameworks are you using?
Earnest And I'm in a stage now where you have
to question every framework, even stuff that made you successful
in the past. You have to question every paradigm because
we are at a point in history, whether we're talking
(12:03):
about venture capital or all the way to politics or economics,
to healthcare, to every function, every industry, We're at a
time of change where one world is dying and the
other world is emerging. And so what you need to
do is see with like I can't I don't know
who said this quote, but people always talk about history
(12:24):
doesn't repeat itself in rhymes. You need to understand what's
the rhyme scheme, what are the invisible truths that are
non consensus today but will be trends tomorrow. And so
for me, even thinking about what's the ideal founder that
creates outlier you know, outcomes, I think that's actively changing too.
Speaker 2 (12:44):
Got it? Got it? Thank you for that. Looks I
couldn't have framed it the way you framed the question
about the framework. That's what I was alluding to. That's
where we are. We see DNA is skicking in. So
you mentioned the move. You went to India. You wanted
to be in the Silicon Valley where there's a lot
of action. From a rec perspective, I mean, do you
(13:07):
do you feel validated in the fact that you chose
to be here? And the second part of that question
and instance, I mean, how has Silicon Valley changed you
as a as a VC? I mean maybe you wouldn't
have done certain things, you know, if you were probably
not looking at the eighteen number of vcs out here.
(13:28):
And of course the founders are flocking here, especially in
today's world with AI. I mean just as a person, right,
I mean, how has Silicon Valley influenced you?
Speaker 1 (13:37):
Wow, that's such a deep question and a great question.
I you know, first I'll start with the first question,
to do I feel validated? You know, like I thinks preferences.
Life is about preferences, and so for me, if you
you know, I had a friend who recently reconnected from
like college where you know, we didn't go to the
same school but we were admitted to the same school
(13:58):
in high school and then just kept in touch, and
you know, she told me, she was like, You've always
been a kind of big city person. And so even
though I grew up in little Rocket's like all right, yeah,
I went to New York next, and then you know,
I went to Chicago, and now I've been in Bay Area.
They're all different in different ways. But I think it
just speaks to kind of like my preference, and you know,
as somebody who's always had the code switch and you know,
(14:22):
society regionally, whatever I ability, I've always been kind of
like in I've read this book last year called Range,
which speaks about how like generalists will win in a
specialized world, and there was one section about just like
how Charles Darwin would always journal and talk to as
many experts as possible, and he the researcher called him
(14:43):
a professional outsider, so he always would take in new
ideas to like iterate on his own views, but he
always appreciated doing both the both like internal debate as
well as like talking to people who focused on it
the best, you know, instead of just being like a
big city person. I think that's what I aspire to, Like,
I love meeting new people, and this is why this
(15:06):
job is a perfect fit for me, and asset class
is the right fit for me. Is I'm paid to
ask questions and meet people who are thinking big, Like
that's literally at all and so for me they are
the second question about like what it's done to me,
I think it's just like what was already there. It
(15:26):
kind of just made it more prevalent and made me
think of like how my career can be aligned with
kind of high view the world. Things I really appreciate
and this idea of kind of truth and it's always changing.
(15:47):
So I don't know if that answers your question, but
like I.
Speaker 2 (15:50):
Think it does. I mean the way I interpret it is,
I mean, you know too, with the different moves that
you said you're dead, I mean it kind of showed
your mental preference to where you want it to be,
Like you said, you know, it suits the fact that
you want to talk to a lot of people. I mean,
if you're in a small city as you can do
it to a zoom and whatnot. But I mean it's
not like meeting people in person like in a big
(16:12):
city Part one. And again, I also think in the
way I understood what you said is that it also
has brought kind of the best out of you because
it kind of resonates with the energy of the place
as well, right, I mean, which is more that founder
of mentality and that v see mentality and the more
like minded people you meet. I mean it kind of reiterates.
(16:33):
That is how I read it.
Speaker 1 (16:34):
Can I say like a fallo up to that, like yeah, please,
I'm an optimistic realist as well. Though, like it's not perfect.
This is far from perfect. It's a lot of problems
being in the Silicon Valley, especially when you look at
just like how the lack of inclusivity there actually is
in how being like a barn of risk rewards certain
(16:55):
people and won't reward everybody, right, or even my industry
has gotten wider and meller over the last even five years,
and so it's not perfect. And even like I feel
like I'm in a better place now here. I've always
liked it, but like realizing it's unlike like that New
York mentality of like, hey, there are steps to success.
(17:17):
I add the dprogram myself from that and take the
best from that of just like all right, I can
make it anywhere, but also incorporate my southern ability to
sometimes be so naive and my ability to like feel
like I can connect anyone, but more importantly being able
to genuinely disarm people in a way that makes them
feel comfortable, and how we can co collaborate success successfully.
(17:39):
So it's not perfect, and you can be successful a
lot of different ways, but you have to break it.
Break the idea of I need to follow a playbook
because if you ask chat GPT or Soro or an Adali,
I guess to make a picture of a typical VC
is not going to look like me. And so given
that not going, I shouldn't follow a playbook that's set
(18:02):
up for them. That honestly, even for somebody who does
look like that, if they're from a different generation, like
that's still not going to work because things are actively moving.
Speaker 2 (18:10):
Yeah, that's a great point just about inclusivity. And how
people look at us and you know, and I think
coming to your point on the playbook aspect as well,
I mean, you know, just the mentality of the different places.
And I can also tie to as you were saying
thinking about the learning aspect that you mentioned about founders,
you know, how you adapt to the different changes and
(18:30):
how you can help you supercharge es capablocity and all
of that. I'm also a firm believer in lifelong learning.
Unless you have that mindset, you're just not going to grow,
you know, I mean, because the world is changing so fast.
And I've also realized sometimes the hard way, you also
have to unlearn some things as fast as possible if
you think that's not good for you. So as much
(18:51):
as learning is important, I always tell this to my
daughter as well. I mean, whether it's bad habits right, Yeah,
learning is as important in life as learning, but you
need to know to what to unload and what's good
for you. Absolutely part of what you said, I mean
resonated with me that way, because there's a lot of
(19:15):
similarities there.
Speaker 1 (19:16):
Yeah, yeah, it makes me think of this. I was
talking to this LP once who had been at a
large endowment of a university in the East Coast and
see he said he always expected great fund managers to
take like take sixty percent of his advice and know
(19:37):
what forty percent wasn't true or was it didn't serve him? Well,
you know, my first response was like, wow, you think
it's sixty percent? Wow, okay this But what he was
getting at the gist is like, even well thought out
advice isn't always applicable to you, you know what's inside
(19:58):
And even this journey of a pie like it's been
kind of like little tidbits and stories like that that
can show you. Yeah, I had plenty of people who
are well meaning, love me, respect me, think I'm smart
and told me not to do it, and now we're
sixty episodes and it's one of the most shrewd things
I've ever done in my life.
Speaker 2 (20:17):
Yeah, beautiful, great segue. I know you have a lot
of things in progress, but I mean everything is kind
of aligning towards you know, what do you want to
do with stress wood and all of that. How did
all that come to your head and how did you
put that vision together to say, Okay, I mean the
(20:37):
podcast is going to help me with this, you know,
I know you launch something called groundwork, which is not
really blogging or not really you know, write ups and whatnot.
But I mean, you know, I think you mentioned it
as well. It's not a resume, it's not this, it's
not that. But I mean you have a certain vision
for it. Can you paint a picture? And what was
in your head when you kind of put that all together?
(20:59):
I mean I felt like, I mean, there's a lot
of thought gone into that for you to come up
with that, because I mean eventually, I mean, it looks beautiful,
but I mean you probably thought about it for many months,
many years before you came up with that.
Speaker 1 (21:12):
Yeah, I would like to say I did, but it
kind of like it's almost had happened over time, but
there's been a lot of thought in it. But it
does It's not always going to be as sequential as
you think. So like, honestly, the podcast came, you know, first,
and it was a time and period when I was
looking to transition it out of my venture firm and
knew I wanted to stay in the venture but like,
what was that going to look like? Was I going
(21:34):
to join at a level below which I that I
was at? Was I going to work in to have
a seat work in something or vertical that maybe I
didn't feel like I was equipped for, or you know,
actually maybe didn't even believe it. And so after a
lot of conversations and speaking to Alexa as my co
host for Swimming with Allocators, we were having similar stories,
(21:56):
and she said and we were having conversations with LPs separately,
and we both came to this idea of like, hey,
this'd be great to share these conversations because I'm learning
from your conversations as you tell me, and you're learning
from mine. And when she came up with a name,
it was just like, we got to do that. Even
if we suck and don't do more than three episodes,
the name is something we have to try. And so
(22:18):
that gave me the idea of like, all right, just
putting myself out there and learning from other people and
then we'll see what comes from it. And it gives
me a kind of a trojan horse to developing relationships
that will last me the next twenty thirty years. And
then I was able. Actually, the name Stresswood came from
one of the interviews of a knew one to start affirm,
(22:40):
but I didn't know what the name would be and
and I've written about this and this and groundwork, and
so people can go I can share the link that
other people can see. But another conversation helped start something
that then helped me go to work. And so this
balance again of like that I got in research, is like, yeah,
you can be an individual contributor and come up with something,
but I ideas come from like other people other ideas,
(23:03):
and then you put your flavor on it, or you
take analogies from outside of your own industry and apply
it to it, and you'll have breakthroughs. So once I
had the nose I always had the north Star, I
was like, all right, it looks like I'm about to
start affirm. Okay, great, I got a name. Ames make
things real. Yeah, you know the story and uh, you
know the Christian Bible is just like and also the
(23:25):
Jewish face the Torah is like, oh, when Adam is
naming things, now they're realer. For some reason, they were
still there, but like it makes them realer. And so
now the way I'm thinking is like, all right, I
got this north Star. I want to launch fundraising this
period in two years. Now what I need to do
in the meantime in between to actually best position myself.
(23:46):
And so that's why I kind of use the things
that I was doing using insights to have kind of
like these different pillars. And the podcast is a part
of that.
Speaker 2 (23:54):
Yeah, beautiful. I mean the party you said about the
name part of it is so true for me as well.
When I started my podcast, because I have the idea
for six months to do something like this, because I've
always been so interested in talking to people learning from them,
especially the founders and that ecosystem. But once I came
up with a name, and just like you, I mean,
(24:14):
I was driving somewhere, I connected two things and said,
this is the name for my podcast, and then within
two weeks I had my first guest. You know, so
it is it is so true what you said. I mean,
I can totally resonate with that part. So what why
how would you differentiate yourself with the firm you're trying
(24:34):
to build with stress word earnest I mean again based
off of the learnings and you know you're upbringing and
your values and everything. I mean, what what is your
vision for stress word? Yeah?
Speaker 1 (24:47):
Well, that concept is one in nature and it essentially
like what it is is trees have natural stressors like
when rain, heat, ice, whatever, and those natural stressors create
a certain type of wood and bark that helps them
sustain themselves with more stressors as well as as they
(25:07):
get bigger and bigger, they can hold their own weight.
And Sarah Samuels, who is from any PC, when we're interviewing,
she spoke about this and then she told a juxtaposition
like juxtaposed it to this experiment in the late eighties
early nineties called biosphere to which was like in Arizona,
this dome and was supposed to be like the best
(25:29):
thing for any vegetation, no stressors, no wind, And what
happened is the trees shot up, but then they fell
over on themselves because they didn't have this certain type
of wood and bark that built up resilience and made
them stronger. And so that was just like a light
bulb to me of like as we enter, you leave
the era of growth at all costs and enter an
(25:51):
exciting opportunity. But equally as humans do if you overdo
it in moderation, the proficiency at all costs or productivity
at all. With AI and automation, you need certain type
of founders to be able to navigate those changes. It
was enough when like the market and macro stayed pretty similar,
was always up into the right. But now so much
(26:14):
is changing from a macro climate to demographic factors, and
so you need founders who have resilience, learning, velocity, and
discernment of how to make decisions and how to build teams.
And so what you need is this great combination of
human plus machines and building a firm that lives through
(26:34):
that applies. That is going to be critical. And so
for us, it's really about the team of investors, right.
And there's been questions on like do vcs actually have
that much impact? And I agree with folks like that,
like if we want an analogy, it's like a more
Quincy Jones than Michael Jackson. Right, the founder is going
to be Michael Jackson.
Speaker 2 (26:53):
Yeah.
Speaker 1 (26:54):
But in a little bit that you can do of
a suggestion of like hey, what if that song went
like this, or what if we limit it to only
ten songs versus fourteen and stuff like that that can
make that could prove out to be strong dividends. So
we really want to test this idea of like what
do network effects look like? And I think it's a
combination of having a team that is truly aligned, which
(27:18):
doesn't usually happen in venture capital, and one in which
that is a group of professional outsiders, so people who
are able to gather those hidden insights that AI can't
get and find what's non consensus today that will be
consensus later to help bridge worlds for the firm as
well as their portfolio founders.
Speaker 2 (27:37):
Okay, beautiful, honest, I love the love the story, love
the version. I mean, I'm going to be sharing for
you and everybody that stress that comes to life before
we wrap up. I also want to do everything that
you've seen in this world. I mean both from a
personal perspective, all the founders you've met, being a founder
who started and failed and then where journey on. Any
(28:01):
core principles are advice that you would give to upcoming founders.
Speaker 1 (28:07):
I think, and this goes to investors as well and
literally almost anybody. Be clear on your why and if
your why matches up with what your north star is.
So for founders is like what type of business do
you want to create? Why? Being self aware unlike what
type of product type is that? And why? And not
just going to being weather veins on like creating ais
(28:30):
hot that'll help me get funded instead of like, no,
this is really a problem I want to solve. I
believe I'm equipped to solve it like no one else
and hit a certain mark of exit and success that
is appealing not only to this pilling to me as
well as my team. Not because I think the by
side of whatever market that I'm selling is that's what
(28:51):
they're into, because that could be fleeting. And what we
see now is a lot of growth companies that are
in between kind of two different markets and now trying
to shift again or figure out what they want to be.
So that why is important. And then for the investors,
like why do you want to be a venture capitalist?
Is venture the right asset class for you? Because it's
(29:11):
more of an art than like lower market pe and
so are you an artist? Are you an architect? Or
are you an executor? And let me not like you
have to execute as a fund manager and venture but
it's a little bit different than kind of like the
kind of you know, the digits and kind of like
the financial statements of one asset class and more of
(29:33):
you looking at like being a coach, being a motivator,
diligencing people, which is more soft.
Speaker 2 (29:40):
Yeah. Thanks so much on this. I mean, I couldn't
have said it better. Your experience really comes through in
everything you talk about, I mean, and your thoughts are
like so well taught through so I couldn't thank you
enough for being on my podcast today and wish you
the very best on this.
Speaker 1 (29:56):
Thanks so much again, Thank you, Anthony, I appreciate you.
This is a huge achievement and continue going.
Speaker 2 (30:02):
Thank you very much. Think that