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<v Speaker 1>This is the Startup Sales Safe podcast.

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<v Speaker 2>Thank you for junion you as a favor like, subscribe

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<v Speaker 2>on YouTube or LinkedIn, and be sure to give us

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<v Speaker 2>your feedback. Hope you enjoyed this episode. Hello everyone, thanks

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<v Speaker 2>for joining us today. Welcome to a brand new episode

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<v Speaker 2>of Startups. They'll say, as always, I'm your host, Anthony Prakash,

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<v Speaker 2>and today I am joined by a very special guest,

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<v Speaker 2>Ernest Sweat. He's joining me from not too far from

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<v Speaker 2>here in the Bay Area. We'll jump into why Ernest

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<v Speaker 2>is here, his mission, and what he is doing very shortly,

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<v Speaker 2>but before that, I wanted to welcome you all to

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<v Speaker 2>the twenty fifth edition of Startups. They'll say, it's this

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<v Speaker 2>very special episode, and I'm so glad that Ernest has

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<v Speaker 2>agreed to be as a guest on this particular podcast.

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<v Speaker 2>I also want to thank all of my previous guests

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<v Speaker 2>we've been on this podcast. It's almost ten months since

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<v Speaker 2>I started this and little did I imagine I'll get

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<v Speaker 2>to a twenty fifth episode. So thanks to all of

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<v Speaker 2>you for your tremendous support. That Ernest welcome to Startups.

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<v Speaker 2>We'll say, thank you.

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<v Speaker 1>For having me, Anthony. I am honored to be your

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<v Speaker 1>twenty fifth guest, and as a fellow podcaster, I think

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<v Speaker 1>people outside of podcasting world don't understand how big of

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<v Speaker 1>an achievement that is. Like it's I can't remember what

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<v Speaker 1>the stat is, but I believe around ninety percent of

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<v Speaker 1>podcast phil Or they stop cease to make a new

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<v Speaker 1>episode after episode ten. So you've already you're in rare air.

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<v Speaker 1>But it's about consistency and keep going.

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<v Speaker 2>Yeah, thank you for that. Honest, I didn't know that statistic.

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<v Speaker 2>I mean, you know, for me, it's just been so

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<v Speaker 2>much fun doing this and just getting to learn from

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<v Speaker 2>people like you. So why don't we just start with

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<v Speaker 2>a little bit of background in your own words about yourself?

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<v Speaker 2>You know whatether, I know you wear a variety of hats.

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<v Speaker 2>The number of hats I can't even imagine. But maybe

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<v Speaker 2>you just talk to people about currently. I know, literally

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<v Speaker 2>you're wearing one, but I mean, in honesty, you're wearing

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<v Speaker 2>so many others. Why don't you just tell us a

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<v Speaker 2>little bit about yourself? Yeah?

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<v Speaker 1>Yeah, So I grew up in Little Rock, Arkansas. I

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<v Speaker 1>start there because I built a lot of kind of

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<v Speaker 1>values and approach to life that I have not just

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<v Speaker 1>because of the place, but more importantly, like my two

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<v Speaker 1>pillars on my parents. And so my father was a

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<v Speaker 1>computer compsigrad who then went to work for the state

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<v Speaker 1>and be the director of it for their workforce development agency.

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<v Speaker 1>And on top of that people talk about the hats

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<v Speaker 1>that I wear. He was also a full time pastor,

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<v Speaker 1>so that whole like, you know, being able to balance

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<v Speaker 1>an act and you can be a full person even

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<v Speaker 1>though as humans we always try to like box people

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<v Speaker 1>in just so we can take on all the information.

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<v Speaker 1>He was living proof of that and inspiration. And then

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<v Speaker 1>my mother who in our own right just like phenomenal person.

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<v Speaker 1>She has always been an educator, and so she taught

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<v Speaker 1>in public schools and Little Rock for about forty years,

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<v Speaker 1>half of that being in Pe. And then around when

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<v Speaker 1>I started going to high school about to go to college,

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<v Speaker 1>she went back to school and then became a science

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<v Speaker 1>teacher in middle school. And so they those careers choices

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<v Speaker 1>of theirs really put it imprint on me and my

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<v Speaker 1>sister is like, you want something where you can earn

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<v Speaker 1>a living but also be able to constantly feed your

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<v Speaker 1>desire to learn, which they had to do in their careers.

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<v Speaker 1>And then the cherry on top is if you can

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<v Speaker 1>find something where you're using those learnings to literally invest

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<v Speaker 1>in other people's success. And so they did that as teachers, preachers,

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<v Speaker 1>government workers. And when I actually found Venture, I was like,

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<v Speaker 1>all right, this is like a through line to kind

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<v Speaker 1>of what our sweat mantra is.

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<v Speaker 2>Beautiful story. I mean, it's amazing how many of us

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<v Speaker 2>get so inspired by our parents. A lot of people,

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<v Speaker 2>I mean even my friends. You know their dads, the doctors,

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<v Speaker 2>they end up being a doctor. The mom's a teacher,

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<v Speaker 2>they end up being a teacher or a nurse. I

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<v Speaker 2>mean during our childhood we don't realize it, but over

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<v Speaker 2>a period of time, I mean we realize that it's

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<v Speaker 2>in our DNA, that's our mission in life as well.

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<v Speaker 2>I mean, so beautiful story. They're honest since little Rock

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<v Speaker 2>and you know your college and I've seen that you've

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<v Speaker 2>been a consultant in a financial services firm. You were

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<v Speaker 2>a founder by yourself, and what you're trying to do

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<v Speaker 2>to pave the way for the next generation of founders.

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<v Speaker 2>So I know it's a long and arduous journey. I'm

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<v Speaker 2>sure right. I mean, you've had a fun, a lot

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<v Speaker 2>of fun along the way to realize saying Okay, I'm ernest.

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<v Speaker 2>This is my mission in life to go help the

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<v Speaker 2>next generation of founders do my own fund. If you

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<v Speaker 2>will talk to us a little bit about you know,

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<v Speaker 2>how did you come to the realization that this is

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<v Speaker 2>what was your calling at least from a professional perspective

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<v Speaker 2>from where you were. I mean, you obviously took your

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<v Speaker 2>first job. I guess that came right out of college

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<v Speaker 2>where you were just tell us a little bit about that.

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<v Speaker 1>Yeah, Like most people, I like finding your and I

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<v Speaker 1>put them one in the same. I think your vocation

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<v Speaker 1>can be a purpose in calling that helps be kind

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<v Speaker 1>of the catalyst to other things that you're passionate about,

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<v Speaker 1>or your influence or even just your responsibility as somebody

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<v Speaker 1>with talent, time and resources. And so for me finding venture,

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<v Speaker 1>it wasn't until of all places, New Delhi, India, where

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<v Speaker 1>I found I was like, oh, this is what I

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<v Speaker 1>want to do for the rest of my life. So

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<v Speaker 1>to not bury the lead. Had experience as an equity

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<v Speaker 1>research analyst, then a failed founder in the world of

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<v Speaker 1>kind of like future of work in at tech and

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<v Speaker 1>that experience in Sunsetting that that company led me to

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<v Speaker 1>go to a business school at Kellogg in the Chicago

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<v Speaker 1>Land area, and I had every intention kind of to

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<v Speaker 1>either kick the can down the road and just be

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<v Speaker 1>like a management consultant, or if I was lucky to

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<v Speaker 1>find a you know, startup, to be the first, second

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<v Speaker 1>or third business hire for them. And I came across

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<v Speaker 1>this opportunity through Kellogg to work at an international venture

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<v Speaker 1>firm and be placed there for the summer, and so

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<v Speaker 1>I applied, I got in, and I was placed in

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<v Speaker 1>New Delhi for an organization called Central Square, which I

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<v Speaker 1>had a venture firm under the Umbrella organ and I

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<v Speaker 1>got placed in New Delhi, India. And so that experience,

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<v Speaker 1>despite in the summer it being one hundred and seventeen

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<v Speaker 1>degrees fahrenheit, you know, it was a blast. I loved it.

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<v Speaker 1>I saw how I could take my experience from equity

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<v Speaker 1>research and apply it to the private markets and just

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<v Speaker 1>the things everything I've been missing in other career stops.

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<v Speaker 1>It answered right. Having the ability to talk to a

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<v Speaker 1>ton of people, having the ability to thesis, build and

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<v Speaker 1>then putting skin in the game. Had everything that I wanted.

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<v Speaker 1>And so that's what really motivated me not to had

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<v Speaker 1>every intention to move back to New York after business school.

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<v Speaker 1>But that gave me the inspiration. I was like, hey,

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<v Speaker 1>maybe I should probably look out to the Bay Area.

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<v Speaker 1>So that's what brought me out to the Bay. It

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<v Speaker 1>made me kind of like zero in to venture got it.

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<v Speaker 2>Got it along the way said and I said, you

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<v Speaker 2>were a failed founder as well, I'm pretty sure you

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<v Speaker 2>maybe think about it, learnings from it, whatnot. And then

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<v Speaker 2>I mean, you obviously to a lot of founders today,

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<v Speaker 2>whether it's just to consult with them or as part

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<v Speaker 2>of your VC role, if you're well, what are the

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<v Speaker 2>sort of learnings that you got being a founder that

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<v Speaker 2>I mean might have formed your principles on? Okam, I mean,

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<v Speaker 2>here are some of the pain points founders go through.

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<v Speaker 2>How can I help circumnavigate some of those things? And

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<v Speaker 2>you know, in today's world.

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<v Speaker 1>And then it's a great question because one thing I

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<v Speaker 1>look for I've always looked for, but I'm really looking

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<v Speaker 1>for now in founders is their ability and their team's

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<v Speaker 1>ability to have learning velocity. And what I mean from

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<v Speaker 1>that is like when they get information from the market

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<v Speaker 1>that might be a hidden insight, or whether they get

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<v Speaker 1>like smacked in the face from competition or a mistake

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<v Speaker 1>with a customer, they're able to take that learning and

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<v Speaker 1>quickly iterate on it to then get escape velocity as

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<v Speaker 1>fast about and so being able to always take information

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<v Speaker 1>figure out what to do next move I needed to

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<v Speaker 1>apply in my own life as well. So yeah, without

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<v Speaker 1>that framework in mind, I came across it. But when

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<v Speaker 1>it looks back at like, hey, my company failed because

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<v Speaker 1>I picked a really tough go to market motion, trying

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<v Speaker 1>to sell through universities or through municipalities. And second kind

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<v Speaker 1>of like a compounding mistake together is if you're going

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<v Speaker 1>to choose that path, you need to have advisors who

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<v Speaker 1>can help you skip steps. And I didn't do that.

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<v Speaker 1>And so ironically enough, as I became a venture capitalist

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<v Speaker 1>and joined a corporate VC out here is my first

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<v Speaker 1>kind of stint as a full time venture capitalist. I

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<v Speaker 1>really got good at like helping companies with go to market,

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<v Speaker 1>helping companies find the advisors that could help them find

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<v Speaker 1>strategic partners or customers, And yeah, I just leveraged the

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<v Speaker 1>hell out of my opportunity working at a large real

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<v Speaker 1>estate company that was in the intersection of logistics and

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<v Speaker 1>real estate and commerce, and not just leverage at brands,

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<v Speaker 1>but really ug in and got my own relationships through

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<v Speaker 1>that organization that could help my portfolio companies and help

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<v Speaker 1>companies that weren't even my portfolio companies but were from

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<v Speaker 1>founders that I respected or that I was trying to

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<v Speaker 1>convince to take my money.

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<v Speaker 2>Got it? Yeah, beautiful. I mean as to how little

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<v Speaker 2>little things in life impact us in the long run.

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<v Speaker 2>And then you know, you think back and saying, I

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<v Speaker 2>had that aha moment from when I was a founder.

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<v Speaker 2>You know, how do I ensure that these ten people

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<v Speaker 2>ahead of me who are taking my money and my

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<v Speaker 2>you know, people who are investing in me, you know,

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<v Speaker 2>applied the right way? So as as a would would

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<v Speaker 2>you call it? You would call yourself a VC right

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<v Speaker 2>now even though you're looking forward to building stress would.

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<v Speaker 1>Yeah, I'm still I'm still investing right now?

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<v Speaker 2>Yeah? Yeah, perfect. Yeah. So so we'll talk about stress

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<v Speaker 2>would in a in a little bit and your vision

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<v Speaker 2>for that and everything. But when you invest in a startup,

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<v Speaker 2>if you will honest right, I mean, how much of

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<v Speaker 2>it is pure research numbers and what I mean, the

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<v Speaker 2>tim and the projections and whatnot versus your gut feel

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<v Speaker 2>as a person you know, with whom you're talking to

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<v Speaker 2>sitting on the other side of the table. I mean,

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<v Speaker 2>do you give that any any weight as it all

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<v Speaker 2>from just your individual perspective.

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<v Speaker 1>Yes, it's an asset class that is more of a

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<v Speaker 1>balance between science and art than others. And based on

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<v Speaker 1>how early you're invested, it's going to be more art

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<v Speaker 1>than science. And because there aren't any real numbers to

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<v Speaker 1>dig into, it's just assumptions. Yeah, and so for me,

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<v Speaker 1>because I'm a Series A and Series B investor, there's

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<v Speaker 1>a little bit more data. But what you're trying to

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<v Speaker 1>determine is like what's repeatable and what has the opportunity

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<v Speaker 1>to actually have what you're underwriting against this, Does this

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<v Speaker 1>team have the opportunity to do something special and unique

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<v Speaker 1>and have a venture backable exit and so a lot

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<v Speaker 1>of that, and this is even before you join the board.

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<v Speaker 1>Invest A lot of that is determining is like, hey,

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<v Speaker 1>do you know, I see these numbers, Like, all right,

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<v Speaker 1>what have you learned? What's the learning velocity there? Like

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<v Speaker 1>what have you learned? What are you going to exploit

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<v Speaker 1>because of that? What's going on in the market that

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<v Speaker 1>might influence you? How's that going to you know, contribute

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<v Speaker 1>or restrict your product? Roadmap. But then the other piece

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<v Speaker 1>is just like who are you as a person, what

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<v Speaker 1>motivates you? What does success look like for you? And

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<v Speaker 1>then how have you been able to do those things

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<v Speaker 1>I wasn't able to do as a founder, but like

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<v Speaker 1>build a strong team around you of both employees and

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<v Speaker 1>advisors that give you a competitive advantage, and that really

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<v Speaker 1>speaks to today's time and opportunity.

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<v Speaker 2>Right.

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<v Speaker 1>Your question, Anthony in the beginning kind of like felt

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<v Speaker 1>like it was a great question and normal question, but

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<v Speaker 1>what underline is like, hey, what frameworks are you using?

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<v Speaker 1>Earnest And I'm in a stage now where you have

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<v Speaker 1>to question every framework, even stuff that made you successful

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<v Speaker 1>in the past. You have to question every paradigm because

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<v Speaker 1>we are at a point in history, whether we're talking

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<v Speaker 1>about venture capital or all the way to politics or economics,

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<v Speaker 1>to healthcare, to every function, every industry, We're at a

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<v Speaker 1>time of change where one world is dying and the

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<v Speaker 1>other world is emerging. And so what you need to

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<v Speaker 1>do is see with like I can't I don't know

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<v Speaker 1>who said this quote, but people always talk about history

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<v Speaker 1>doesn't repeat itself in rhymes. You need to understand what's

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<v Speaker 1>the rhyme scheme, what are the invisible truths that are

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<v Speaker 1>non consensus today but will be trends tomorrow. And so

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<v Speaker 1>for me, even thinking about what's the ideal founder that

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<v Speaker 1>creates outlier you know, outcomes, I think that's actively changing too.

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<v Speaker 2>Got it? Got it? Thank you for that. Looks I

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<v Speaker 2>couldn't have framed it the way you framed the question

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<v Speaker 2>about the framework. That's what I was alluding to. That's

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<v Speaker 2>where we are. We see DNA is skicking in. So

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<v Speaker 2>you mentioned the move. You went to India. You wanted

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<v Speaker 2>to be in the Silicon Valley where there's a lot

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<v Speaker 2>of action. From a rec perspective, I mean, do you

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<v Speaker 2>do you feel validated in the fact that you chose

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<v Speaker 2>to be here? And the second part of that question

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<v Speaker 2>and instance, I mean, how has Silicon Valley changed you

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<v Speaker 2>as a as a VC? I mean maybe you wouldn't

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<v Speaker 2>have done certain things, you know, if you were probably

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<v Speaker 2>not looking at the eighteen number of vcs out here.

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<v Speaker 2>And of course the founders are flocking here, especially in

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<v Speaker 2>today's world with AI. I mean just as a person, right,

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<v Speaker 2>I mean, how has Silicon Valley influenced you?

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<v Speaker 1>Wow, that's such a deep question and a great question.

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<v Speaker 1>I you know, first I'll start with the first question,

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<v Speaker 1>to do I feel validated? You know, like I thinks preferences.

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<v Speaker 1>Life is about preferences, and so for me, if you

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<v Speaker 1>you know, I had a friend who recently reconnected from

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<v Speaker 1>like college where you know, we didn't go to the

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<v Speaker 1>same school but we were admitted to the same school

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<v Speaker 1>in high school and then just kept in touch, and

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<v Speaker 1>you know, she told me, she was like, You've always

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<v Speaker 1>been a kind of big city person. And so even

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<v Speaker 1>though I grew up in little Rocket's like all right, yeah,

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<v Speaker 1>I went to New York next, and then you know,

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<v Speaker 1>I went to Chicago, and now I've been in Bay Area.

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<v Speaker 1>They're all different in different ways. But I think it

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<v Speaker 1>just speaks to kind of like my preference, and you know,

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<v Speaker 1>as somebody who's always had the code switch and you know,

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<v Speaker 1>society regionally, whatever I ability, I've always been kind of

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<v Speaker 1>like in I've read this book last year called Range,

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<v Speaker 1>which speaks about how like generalists will win in a

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<v Speaker 1>specialized world, and there was one section about just like

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<v Speaker 1>how Charles Darwin would always journal and talk to as

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<v Speaker 1>many experts as possible, and he the researcher called him

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<v Speaker 1>a professional outsider, so he always would take in new

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<v Speaker 1>ideas to like iterate on his own views, but he

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<v Speaker 1>always appreciated doing both the both like internal debate as

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<v Speaker 1>well as like talking to people who focused on it

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<v Speaker 1>the best, you know, instead of just being like a

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<v Speaker 1>big city person. I think that's what I aspire to, Like,

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<v Speaker 1>I love meeting new people, and this is why this

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<v Speaker 1>job is a perfect fit for me, and asset class

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<v Speaker 1>is the right fit for me. Is I'm paid to

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<v Speaker 1>ask questions and meet people who are thinking big, Like

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<v Speaker 1>that's literally at all and so for me they are

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<v Speaker 1>the second question about like what it's done to me,

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<v Speaker 1>I think it's just like what was already there. It

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<v Speaker 1>kind of just made it more prevalent and made me

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<v Speaker 1>think of like how my career can be aligned with

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<v Speaker 1>kind of high view the world. Things I really appreciate

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<v Speaker 1>and this idea of kind of truth and it's always changing.

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<v Speaker 1>So I don't know if that answers your question, but

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<v Speaker 1>like I.

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<v Speaker 2>Think it does. I mean the way I interpret it is,

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<v Speaker 2>I mean, you know too, with the different moves that

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<v Speaker 2>you said you're dead, I mean it kind of showed

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<v Speaker 2>your mental preference to where you want it to be,

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<v Speaker 2>Like you said, you know, it suits the fact that

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<v Speaker 2>you want to talk to a lot of people. I mean,

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<v Speaker 2>if you're in a small city as you can do

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<v Speaker 2>it to a zoom and whatnot. But I mean it's

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<v Speaker 2>not like meeting people in person like in a big

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<v Speaker 2>city Part one. And again, I also think in the

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<v Speaker 2>way I understood what you said is that it also

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<v Speaker 2>has brought kind of the best out of you because

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<v Speaker 2>it kind of resonates with the energy of the place

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<v Speaker 2>as well, right, I mean, which is more that founder

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<v Speaker 2>of mentality and that v see mentality and the more

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<v Speaker 2>like minded people you meet. I mean it kind of reiterates.

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<v Speaker 2>That is how I read it.

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<v Speaker 1>Can I say like a fallo up to that, like yeah, please,

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<v Speaker 1>I'm an optimistic realist as well. Though, like it's not perfect.

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<v Speaker 1>This is far from perfect. It's a lot of problems

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<v Speaker 1>being in the Silicon Valley, especially when you look at

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<v Speaker 1>just like how the lack of inclusivity there actually is

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<v Speaker 1>in how being like a barn of risk rewards certain

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<v Speaker 1>people and won't reward everybody, right, or even my industry

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<v Speaker 1>has gotten wider and meller over the last even five years,

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<v Speaker 1>and so it's not perfect. And even like I feel

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<v Speaker 1>like I'm in a better place now here. I've always

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<v Speaker 1>liked it, but like realizing it's unlike like that New

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<v Speaker 1>York mentality of like, hey, there are steps to success.

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<v Speaker 1>I add the dprogram myself from that and take the

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<v Speaker 1>best from that of just like all right, I can

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<v Speaker 1>make it anywhere, but also incorporate my southern ability to

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<v Speaker 1>sometimes be so naive and my ability to like feel

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<v Speaker 1>like I can connect anyone, but more importantly being able

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<v Speaker 1>to genuinely disarm people in a way that makes them

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<v Speaker 1>feel comfortable, and how we can co collaborate success successfully.

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<v Speaker 1>So it's not perfect, and you can be successful a

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<v Speaker 1>lot of different ways, but you have to break it.

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<v Speaker 1>Break the idea of I need to follow a playbook

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<v Speaker 1>because if you ask chat GPT or Soro or an Adali,

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<v Speaker 1>I guess to make a picture of a typical VC

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<v Speaker 1>is not going to look like me. And so given

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<v Speaker 1>that not going, I shouldn't follow a playbook that's set

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<v Speaker 1>up for them. That honestly, even for somebody who does

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<v Speaker 1>look like that, if they're from a different generation, like

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<v Speaker 1>that's still not going to work because things are actively moving.

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<v Speaker 2>Yeah, that's a great point just about inclusivity. And how

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<v Speaker 2>people look at us and you know, and I think

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<v Speaker 2>coming to your point on the playbook aspect as well,

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<v Speaker 2>I mean, you know, just the mentality of the different places.

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<v Speaker 2>And I can also tie to as you were saying

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<v Speaker 2>thinking about the learning aspect that you mentioned about founders,

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<v Speaker 2>you know, how you adapt to the different changes and

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<v Speaker 2>how you can help you supercharge es capablocity and all

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<v Speaker 2>of that. I'm also a firm believer in lifelong learning.

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<v Speaker 2>Unless you have that mindset, you're just not going to grow,

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<v Speaker 2>you know, I mean, because the world is changing so fast.

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<v Speaker 2>And I've also realized sometimes the hard way, you also

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<v Speaker 2>have to unlearn some things as fast as possible if

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<v Speaker 2>you think that's not good for you. So as much

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<v Speaker 2>as learning is important, I always tell this to my

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<v Speaker 2>daughter as well. I mean, whether it's bad habits right, Yeah,

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<v Speaker 2>learning is as important in life as learning, but you

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<v Speaker 2>need to know to what to unload and what's good

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<v Speaker 2>for you. Absolutely part of what you said, I mean

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<v Speaker 2>resonated with me that way, because there's a lot of

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<v Speaker 2>similarities there.

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<v Speaker 1>Yeah, yeah, it makes me think of this. I was

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<v Speaker 1>talking to this LP once who had been at a

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<v Speaker 1>large endowment of a university in the East Coast and

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<v Speaker 1>see he said he always expected great fund managers to

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<v Speaker 1>take like take sixty percent of his advice and know

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<v Speaker 1>what forty percent wasn't true or was it didn't serve him? Well,

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<v Speaker 1>you know, my first response was like, wow, you think

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<v Speaker 1>it's sixty percent? Wow, okay this But what he was

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<v Speaker 1>getting at the gist is like, even well thought out

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<v Speaker 1>advice isn't always applicable to you, you know what's inside

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<v Speaker 1>And even this journey of a pie like it's been

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<v Speaker 1>kind of like little tidbits and stories like that that

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<v Speaker 1>can show you. Yeah, I had plenty of people who

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<v Speaker 1>are well meaning, love me, respect me, think I'm smart

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<v Speaker 1>and told me not to do it, and now we're

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<v Speaker 1>sixty episodes and it's one of the most shrewd things

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<v Speaker 1>I've ever done in my life.

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<v Speaker 2>Yeah, beautiful, great segue. I know you have a lot

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<v Speaker 2>of things in progress, but I mean everything is kind

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<v Speaker 2>of aligning towards you know, what do you want to

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<v Speaker 2>do with stress wood and all of that. How did

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<v Speaker 2>all that come to your head and how did you

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<v Speaker 2>put that vision together to say, Okay, I mean the

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<v Speaker 2>podcast is going to help me with this, you know,

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<v Speaker 2>I know you launch something called groundwork, which is not

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<v Speaker 2>really blogging or not really you know, write ups and whatnot.

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<v Speaker 2>But I mean, you know, I think you mentioned it

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<v Speaker 2>as well. It's not a resume, it's not this, it's

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<v Speaker 2>not that. But I mean you have a certain vision

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<v Speaker 2>for it. Can you paint a picture? And what was

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<v Speaker 2>in your head when you kind of put that all together?

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<v Speaker 2>I mean I felt like, I mean, there's a lot

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<v Speaker 2>of thought gone into that for you to come up

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<v Speaker 2>with that, because I mean eventually, I mean, it looks beautiful,

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<v Speaker 2>but I mean you probably thought about it for many months,

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<v Speaker 2>many years before you came up with that.

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<v Speaker 1>Yeah, I would like to say I did, but it

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<v Speaker 1>kind of like it's almost had happened over time, but

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<v Speaker 1>there's been a lot of thought in it. But it

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<v Speaker 1>does It's not always going to be as sequential as

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<v Speaker 1>you think. So like, honestly, the podcast came, you know, first,

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<v Speaker 1>and it was a time and period when I was

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<v Speaker 1>looking to transition it out of my venture firm and

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<v Speaker 1>knew I wanted to stay in the venture but like,

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<v Speaker 1>what was that going to look like? Was I going

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<v Speaker 1>to join at a level below which I that I

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<v Speaker 1>was at? Was I going to work in to have

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<v Speaker 1>a seat work in something or vertical that maybe I

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<v Speaker 1>didn't feel like I was equipped for, or you know,

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<v Speaker 1>actually maybe didn't even believe it. And so after a

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<v Speaker 1>lot of conversations and speaking to Alexa as my co

419
00:21:52.680 --> 00:21:55.839
<v Speaker 1>host for Swimming with Allocators, we were having similar stories,

420
00:21:56.039 --> 00:21:59.480
<v Speaker 1>and she said and we were having conversations with LPs separately,

421
00:22:00.039 --> 00:22:02.400
<v Speaker 1>and we both came to this idea of like, hey,

422
00:22:02.440 --> 00:22:05.039
<v Speaker 1>this'd be great to share these conversations because I'm learning

423
00:22:05.039 --> 00:22:07.079
<v Speaker 1>from your conversations as you tell me, and you're learning

424
00:22:07.119 --> 00:22:09.079
<v Speaker 1>from mine. And when she came up with a name,

425
00:22:09.240 --> 00:22:11.279
<v Speaker 1>it was just like, we got to do that. Even

426
00:22:11.359 --> 00:22:14.799
<v Speaker 1>if we suck and don't do more than three episodes,

427
00:22:14.839 --> 00:22:18.119
<v Speaker 1>the name is something we have to try. And so

428
00:22:18.519 --> 00:22:21.680
<v Speaker 1>that gave me the idea of like, all right, just

429
00:22:21.720 --> 00:22:26.039
<v Speaker 1>putting myself out there and learning from other people and

430
00:22:26.039 --> 00:22:28.319
<v Speaker 1>then we'll see what comes from it. And it gives

431
00:22:28.359 --> 00:22:31.640
<v Speaker 1>me a kind of a trojan horse to developing relationships

432
00:22:31.640 --> 00:22:34.119
<v Speaker 1>that will last me the next twenty thirty years. And

433
00:22:34.880 --> 00:22:37.720
<v Speaker 1>then I was able. Actually, the name Stresswood came from

434
00:22:37.720 --> 00:22:40.720
<v Speaker 1>one of the interviews of a knew one to start affirm,

435
00:22:40.799 --> 00:22:42.920
<v Speaker 1>but I didn't know what the name would be and

436
00:22:42.839 --> 00:22:45.119
<v Speaker 1>and I've written about this and this and groundwork, and

437
00:22:45.200 --> 00:22:46.920
<v Speaker 1>so people can go I can share the link that

438
00:22:46.920 --> 00:22:51.000
<v Speaker 1>other people can see. But another conversation helped start something

439
00:22:51.039 --> 00:22:52.960
<v Speaker 1>that then helped me go to work. And so this

440
00:22:53.160 --> 00:22:56.200
<v Speaker 1>balance again of like that I got in research, is like, yeah,

441
00:22:56.240 --> 00:22:59.319
<v Speaker 1>you can be an individual contributor and come up with something,

442
00:22:59.680 --> 00:23:03.039
<v Speaker 1>but I ideas come from like other people other ideas,

443
00:23:03.039 --> 00:23:05.160
<v Speaker 1>and then you put your flavor on it, or you

444
00:23:05.200 --> 00:23:08.799
<v Speaker 1>take analogies from outside of your own industry and apply

445
00:23:08.839 --> 00:23:11.240
<v Speaker 1>it to it, and you'll have breakthroughs. So once I

446
00:23:11.279 --> 00:23:12.640
<v Speaker 1>had the nose I always had the north Star, I

447
00:23:12.720 --> 00:23:13.720
<v Speaker 1>was like, all right, it looks like I'm about to

448
00:23:13.720 --> 00:23:16.559
<v Speaker 1>start affirm. Okay, great, I got a name. Ames make

449
00:23:16.680 --> 00:23:20.559
<v Speaker 1>things real. Yeah, you know the story and uh, you

450
00:23:20.599 --> 00:23:24.119
<v Speaker 1>know the Christian Bible is just like and also the

451
00:23:25.079 --> 00:23:28.680
<v Speaker 1>Jewish face the Torah is like, oh, when Adam is

452
00:23:28.759 --> 00:23:31.880
<v Speaker 1>naming things, now they're realer. For some reason, they were

453
00:23:31.880 --> 00:23:34.079
<v Speaker 1>still there, but like it makes them realer. And so

454
00:23:34.400 --> 00:23:36.440
<v Speaker 1>now the way I'm thinking is like, all right, I

455
00:23:36.480 --> 00:23:39.960
<v Speaker 1>got this north Star. I want to launch fundraising this

456
00:23:40.200 --> 00:23:42.799
<v Speaker 1>period in two years. Now what I need to do

457
00:23:42.839 --> 00:23:46.200
<v Speaker 1>in the meantime in between to actually best position myself.

458
00:23:46.240 --> 00:23:48.240
<v Speaker 1>And so that's why I kind of use the things

459
00:23:48.240 --> 00:23:51.000
<v Speaker 1>that I was doing using insights to have kind of

460
00:23:51.000 --> 00:23:53.680
<v Speaker 1>like these different pillars. And the podcast is a part

461
00:23:53.720 --> 00:23:53.880
<v Speaker 1>of that.

462
00:23:54.160 --> 00:23:56.960
<v Speaker 2>Yeah, beautiful. I mean the party you said about the

463
00:23:57.079 --> 00:23:59.680
<v Speaker 2>name part of it is so true for me as well.

464
00:23:59.680 --> 00:24:02.759
<v Speaker 2>When I started my podcast, because I have the idea

465
00:24:02.839 --> 00:24:05.160
<v Speaker 2>for six months to do something like this, because I've

466
00:24:05.240 --> 00:24:08.799
<v Speaker 2>always been so interested in talking to people learning from them,

467
00:24:08.880 --> 00:24:12.880
<v Speaker 2>especially the founders and that ecosystem. But once I came

468
00:24:12.960 --> 00:24:14.559
<v Speaker 2>up with a name, and just like you, I mean,

469
00:24:14.599 --> 00:24:17.200
<v Speaker 2>I was driving somewhere, I connected two things and said,

470
00:24:17.200 --> 00:24:20.319
<v Speaker 2>this is the name for my podcast, and then within

471
00:24:20.359 --> 00:24:23.200
<v Speaker 2>two weeks I had my first guest. You know, so

472
00:24:23.440 --> 00:24:25.680
<v Speaker 2>it is it is so true what you said. I mean,

473
00:24:25.720 --> 00:24:29.799
<v Speaker 2>I can totally resonate with that part. So what why

474
00:24:30.119 --> 00:24:34.920
<v Speaker 2>how would you differentiate yourself with the firm you're trying

475
00:24:34.920 --> 00:24:38.720
<v Speaker 2>to build with stress word earnest I mean again based

476
00:24:38.759 --> 00:24:42.359
<v Speaker 2>off of the learnings and you know you're upbringing and

477
00:24:42.400 --> 00:24:45.559
<v Speaker 2>your values and everything. I mean, what what is your

478
00:24:45.640 --> 00:24:47.000
<v Speaker 2>vision for stress word? Yeah?

479
00:24:47.000 --> 00:24:51.799
<v Speaker 1>Well, that concept is one in nature and it essentially

480
00:24:51.920 --> 00:24:55.480
<v Speaker 1>like what it is is trees have natural stressors like

481
00:24:55.880 --> 00:25:00.200
<v Speaker 1>when rain, heat, ice, whatever, and those natural stressors create

482
00:25:00.240 --> 00:25:03.079
<v Speaker 1>a certain type of wood and bark that helps them

483
00:25:03.799 --> 00:25:07.440
<v Speaker 1>sustain themselves with more stressors as well as as they

484
00:25:07.440 --> 00:25:09.880
<v Speaker 1>get bigger and bigger, they can hold their own weight.

485
00:25:10.039 --> 00:25:13.480
<v Speaker 1>And Sarah Samuels, who is from any PC, when we're interviewing,

486
00:25:13.599 --> 00:25:18.200
<v Speaker 1>she spoke about this and then she told a juxtaposition

487
00:25:18.640 --> 00:25:22.480
<v Speaker 1>like juxtaposed it to this experiment in the late eighties

488
00:25:22.480 --> 00:25:26.319
<v Speaker 1>early nineties called biosphere to which was like in Arizona,

489
00:25:26.440 --> 00:25:29.640
<v Speaker 1>this dome and was supposed to be like the best

490
00:25:29.720 --> 00:25:33.279
<v Speaker 1>thing for any vegetation, no stressors, no wind, And what

491
00:25:33.440 --> 00:25:35.640
<v Speaker 1>happened is the trees shot up, but then they fell

492
00:25:35.680 --> 00:25:39.000
<v Speaker 1>over on themselves because they didn't have this certain type

493
00:25:39.000 --> 00:25:42.160
<v Speaker 1>of wood and bark that built up resilience and made

494
00:25:42.200 --> 00:25:44.960
<v Speaker 1>them stronger. And so that was just like a light

495
00:25:45.000 --> 00:25:48.680
<v Speaker 1>bulb to me of like as we enter, you leave

496
00:25:48.759 --> 00:25:51.960
<v Speaker 1>the era of growth at all costs and enter an

497
00:25:51.960 --> 00:25:54.839
<v Speaker 1>exciting opportunity. But equally as humans do if you overdo

498
00:25:54.880 --> 00:25:59.480
<v Speaker 1>it in moderation, the proficiency at all costs or productivity

499
00:25:59.519 --> 00:26:02.680
<v Speaker 1>at all. With AI and automation, you need certain type

500
00:26:02.680 --> 00:26:06.920
<v Speaker 1>of founders to be able to navigate those changes. It

501
00:26:07.039 --> 00:26:10.759
<v Speaker 1>was enough when like the market and macro stayed pretty similar,

502
00:26:11.039 --> 00:26:14.079
<v Speaker 1>was always up into the right. But now so much

503
00:26:14.160 --> 00:26:19.200
<v Speaker 1>is changing from a macro climate to demographic factors, and

504
00:26:19.240 --> 00:26:22.920
<v Speaker 1>so you need founders who have resilience, learning, velocity, and

505
00:26:23.000 --> 00:26:26.279
<v Speaker 1>discernment of how to make decisions and how to build teams.

506
00:26:26.359 --> 00:26:29.920
<v Speaker 1>And so what you need is this great combination of

507
00:26:30.119 --> 00:26:34.720
<v Speaker 1>human plus machines and building a firm that lives through

508
00:26:34.759 --> 00:26:37.880
<v Speaker 1>that applies. That is going to be critical. And so

509
00:26:38.079 --> 00:26:41.480
<v Speaker 1>for us, it's really about the team of investors, right.

510
00:26:41.519 --> 00:26:44.119
<v Speaker 1>And there's been questions on like do vcs actually have

511
00:26:44.200 --> 00:26:46.000
<v Speaker 1>that much impact? And I agree with folks like that,

512
00:26:46.079 --> 00:26:48.640
<v Speaker 1>like if we want an analogy, it's like a more

513
00:26:48.720 --> 00:26:52.319
<v Speaker 1>Quincy Jones than Michael Jackson. Right, the founder is going

514
00:26:52.359 --> 00:26:53.160
<v Speaker 1>to be Michael Jackson.

515
00:26:53.279 --> 00:26:53.440
<v Speaker 2>Yeah.

516
00:26:54.359 --> 00:26:56.200
<v Speaker 1>But in a little bit that you can do of

517
00:26:56.240 --> 00:26:58.839
<v Speaker 1>a suggestion of like hey, what if that song went

518
00:26:58.960 --> 00:27:01.400
<v Speaker 1>like this, or what if we limit it to only

519
00:27:01.480 --> 00:27:05.160
<v Speaker 1>ten songs versus fourteen and stuff like that that can

520
00:27:05.319 --> 00:27:08.359
<v Speaker 1>make that could prove out to be strong dividends. So

521
00:27:08.720 --> 00:27:11.440
<v Speaker 1>we really want to test this idea of like what

522
00:27:11.519 --> 00:27:14.240
<v Speaker 1>do network effects look like? And I think it's a

523
00:27:14.240 --> 00:27:18.440
<v Speaker 1>combination of having a team that is truly aligned, which

524
00:27:18.720 --> 00:27:21.720
<v Speaker 1>doesn't usually happen in venture capital, and one in which

525
00:27:21.799 --> 00:27:24.960
<v Speaker 1>that is a group of professional outsiders, so people who

526
00:27:24.960 --> 00:27:27.920
<v Speaker 1>are able to gather those hidden insights that AI can't

527
00:27:27.960 --> 00:27:31.200
<v Speaker 1>get and find what's non consensus today that will be

528
00:27:31.279 --> 00:27:35.279
<v Speaker 1>consensus later to help bridge worlds for the firm as

529
00:27:35.359 --> 00:27:37.519
<v Speaker 1>well as their portfolio founders.

530
00:27:37.720 --> 00:27:40.839
<v Speaker 2>Okay, beautiful, honest, I love the love the story, love

531
00:27:40.880 --> 00:27:43.319
<v Speaker 2>the version. I mean, I'm going to be sharing for

532
00:27:43.400 --> 00:27:48.319
<v Speaker 2>you and everybody that stress that comes to life before

533
00:27:48.319 --> 00:27:50.359
<v Speaker 2>we wrap up. I also want to do everything that

534
00:27:50.400 --> 00:27:52.640
<v Speaker 2>you've seen in this world. I mean both from a

535
00:27:52.680 --> 00:27:56.799
<v Speaker 2>personal perspective, all the founders you've met, being a founder

536
00:27:56.920 --> 00:28:01.119
<v Speaker 2>who started and failed and then where journey on. Any

537
00:28:01.279 --> 00:28:07.640
<v Speaker 2>core principles are advice that you would give to upcoming founders.

538
00:28:07.160 --> 00:28:10.279
<v Speaker 1>I think, and this goes to investors as well and

539
00:28:10.400 --> 00:28:13.240
<v Speaker 1>literally almost anybody. Be clear on your why and if

540
00:28:13.279 --> 00:28:15.920
<v Speaker 1>your why matches up with what your north star is.

541
00:28:16.200 --> 00:28:18.599
<v Speaker 1>So for founders is like what type of business do

542
00:28:18.640 --> 00:28:22.000
<v Speaker 1>you want to create? Why? Being self aware unlike what

543
00:28:22.039 --> 00:28:25.400
<v Speaker 1>type of product type is that? And why? And not

544
00:28:25.640 --> 00:28:30.039
<v Speaker 1>just going to being weather veins on like creating ais

545
00:28:30.119 --> 00:28:32.880
<v Speaker 1>hot that'll help me get funded instead of like, no,

546
00:28:33.000 --> 00:28:35.160
<v Speaker 1>this is really a problem I want to solve. I

547
00:28:35.200 --> 00:28:37.559
<v Speaker 1>believe I'm equipped to solve it like no one else

548
00:28:37.680 --> 00:28:41.200
<v Speaker 1>and hit a certain mark of exit and success that

549
00:28:41.359 --> 00:28:44.640
<v Speaker 1>is appealing not only to this pilling to me as

550
00:28:44.680 --> 00:28:47.920
<v Speaker 1>well as my team. Not because I think the by

551
00:28:48.079 --> 00:28:51.359
<v Speaker 1>side of whatever market that I'm selling is that's what

552
00:28:51.400 --> 00:28:54.279
<v Speaker 1>they're into, because that could be fleeting. And what we

553
00:28:54.319 --> 00:28:56.440
<v Speaker 1>see now is a lot of growth companies that are

554
00:28:56.640 --> 00:28:59.960
<v Speaker 1>in between kind of two different markets and now trying

555
00:29:00.240 --> 00:29:04.039
<v Speaker 1>to shift again or figure out what they want to be.

556
00:29:04.440 --> 00:29:06.720
<v Speaker 1>So that why is important. And then for the investors,

557
00:29:06.960 --> 00:29:08.839
<v Speaker 1>like why do you want to be a venture capitalist?

558
00:29:09.160 --> 00:29:11.680
<v Speaker 1>Is venture the right asset class for you? Because it's

559
00:29:11.680 --> 00:29:15.240
<v Speaker 1>more of an art than like lower market pe and

560
00:29:15.319 --> 00:29:18.200
<v Speaker 1>so are you an artist? Are you an architect? Or

561
00:29:18.240 --> 00:29:20.839
<v Speaker 1>are you an executor? And let me not like you

562
00:29:20.920 --> 00:29:23.160
<v Speaker 1>have to execute as a fund manager and venture but

563
00:29:23.480 --> 00:29:26.319
<v Speaker 1>it's a little bit different than kind of like the

564
00:29:26.880 --> 00:29:30.279
<v Speaker 1>kind of you know, the digits and kind of like

565
00:29:30.519 --> 00:29:33.559
<v Speaker 1>the financial statements of one asset class and more of

566
00:29:33.599 --> 00:29:36.720
<v Speaker 1>you looking at like being a coach, being a motivator,

567
00:29:37.519 --> 00:29:39.799
<v Speaker 1>diligencing people, which is more soft.

568
00:29:40.039 --> 00:29:42.319
<v Speaker 2>Yeah. Thanks so much on this. I mean, I couldn't

569
00:29:42.319 --> 00:29:45.319
<v Speaker 2>have said it better. Your experience really comes through in

570
00:29:45.400 --> 00:29:48.880
<v Speaker 2>everything you talk about, I mean, and your thoughts are

571
00:29:49.000 --> 00:29:51.640
<v Speaker 2>like so well taught through so I couldn't thank you

572
00:29:51.759 --> 00:29:55.000
<v Speaker 2>enough for being on my podcast today and wish you

573
00:29:55.240 --> 00:29:56.160
<v Speaker 2>the very best on this.

574
00:29:56.400 --> 00:29:59.039
<v Speaker 1>Thanks so much again, Thank you, Anthony, I appreciate you.

575
00:29:59.359 --> 00:30:02.200
<v Speaker 1>This is a huge achievement and continue going.

576
00:30:02.359 --> 00:30:03.839
<v Speaker 2>Thank you very much. Think that
