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Nov. 11, 2026

Ali Partovi - Neo CEO ($600M Fund) & Code.org Co-Founder | The First Investor in Cursor, Facebook, Airbnb and Dropbox on How He Spots Winners Before Anyone Else

Ali Partovi - Neo CEO ($600M Fund) & Code.org Co-Founder | The First Investor in Cursor, Facebook, Airbnb and Dropbox on How He Spots Winners Before Anyone Else
Success Story with Scott Clary
Ali Partovi - Neo CEO ($600M Fund) & Code.org Co-Founder | The First Investor in Cursor, Facebook, Airbnb and Dropbox on How He Spots Winners Before Anyone Else

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Ali Partovi is the CEO of Neo and the co-founder of Code.org, and he has built his career on one idea: find exceptional people before anyone else does. At Neo, he scouts top student engineers early, screens them with a coding assessment and in-person interviews, and often writes the first check when they start companies. That approach made him the first investor in Cursor, which SpaceX agreed to acquire for $60 billion in stock, and an early backer of Facebook, Dropbox and Airbnb. Neo closed a $320 million fund in April 2025, and its 2021 fund of $150 million has reportedly grown to $1.2 billion. In 2013 he and his twin brother Hadi launched Code.org, which has reached about 100 million students. Before that, he helped found LinkExchange, which Microsoft bought for $265 million in 1998. It all started in Iran, where he was born, and his family moved to the U.S. in the 1980s. By ten, he and Hadi were coding on a Commodore 64.

➡️ Show Links

https://www.instagram.com/partovi_ali/

https://x.com/apartovi

https://www.linkedin.com/in/apartovi/

➡️ Podcast Sponsors

Hubspot - https://hubspot.com/

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NetSuite - https://netsuite.com/scottclary/

Framer - https://framer.com/design (Code: SuccessStory)

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MyFitnessPal - https://podcasts.myfitnesspal.com (Code: SCOTT)

Life at the Speed of Play - https://getmarksbook.com/success

Noom - https://noom.com

➡️ Talking Points

00:00 – Intro

01:46 – How He Lost a $50M Deal With Steve Jobs

10:11 – The Lonely Reality of Being a Founder

11:30 – How to Negotiate Without Bluffing

13:41 – Vulnerability Isn’t Weakness

19:39 – Sponsor Break

20:59 – Why Founders Need to Conquer Their Minds

23:49 – The Meaning Behind NEO

25:44 – Why Smart People Miss Big Opportunities

28:55 – Build Courage Through Small Risks

33:11 – Why Startup Failure Doesn’t Define You

36:02 – What Makes a Founder Worth Betting On

46:02 – Sponsor Break

48:10 – How to Become More Magnetic

52:13 – Why He Created Confession

54:07 – The Hidden Struggles of Great Founders

56:01 – The Myth of the Superhuman Founder

57:56 – The Mental Hurdles Every Founder Faces

1:02:02 – Why Talking About Fear Makes It Smaller

1:03:24 – The Skills Founders Need in the AI Era

1:07:02 – Why Everyone Is a Manager Now

1:10:05 – How He Decides Who to Invest In

1:13:50 – The Risk Lesson He’d Teach His Younger Self

1:15:09 – Stop Letting Fear of Judgment Hold You Back

Transcript

WEBVTT

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Your new podcast, it has a tagline.

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Behind every success story, there are painful lessons.

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What is your painful lesson?

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My most traumatic career experience, which was my encounter with Steve Jobs, where I was potentially selling my own startup for $50 million, and I destroyed the deal literally with one sentence.

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Today's guest is Ali Partovi, entrepreneur, investor, and CEO of NEO, a venture fund and mentorship community for emerging founders, and was an early investor in companies like Facebook, Airbnb, and Dropbox.

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In this episode, we explore entrepreneurship, investing in exceptional talent, and what it takes to build successful companies.

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What's the lesson for an entrepreneur right now?

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How do they be vulnerable with somebody and be honest without killing their chances of being successful?

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There's a difference between being vulnerable and being weak.

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It takes extra strength.

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It shows a sense of groundedness and comfort with yourself and confidence to be vulnerable.

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What's the lesson that you learned about yourself that you want to leave with a founder who's just starting out?

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I make the most mistakes when I have a scarcity mentality.

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I've made the best decisions when I had an abundance mentality.

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HubSpot is a success story partner.

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So if you're still jumping between emails, call notes, and spreadsheets just to figure out where a deal stands, HubSpot's starter plan puts all of that in one place.

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It pulls info from your calls and emails, logs it, and summarizes it for you.

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When your call ends, it pulls the next steps from your notes and drafts suggested follow-ups.

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It keeps your records up to date so you can spend more time building demand and closing deals and less time updating everything yourself.

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Your customer info, insights, and next steps are there when you need them.

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Try the starter plan for $10 a month.

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Learn more at HubSpot.com.

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Your new podcast, Confession, it has a tagline.

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Behind every success story, there are painful lessons that haven't been told.

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What is your painful lesson?

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Yeah, well, I actually have so many because I've done so many dumb things that I could choose from them.

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But what inspired me to do this podcast actually was I shared a story on LinkedIn and Twitter of what was definitely my most traumatic experience.

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career experience, which was my encounter with Steve Jobs, where basically I was potentially selling my own startup for $50 million.

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And I destroyed the deal with literally with one sentence that was, you know, that messed it up.

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Basically, I was pumping my startup too hard and he could tell I was trying to, you know, to trick him.

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And, you know, I was trying

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Yeah, I could tell you the whole story, but when I shared it on the internet, it was like this had been something I had carried some shame for.

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Like for years, I had not talked to anyone about it, but inside had just been reliving this experience.

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And when I shared it, it was like a huge weight lifted.

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It went kind of viral, and that inspired me to think...

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You know, maybe other people have experiences like this that they're carrying with them that if you give them a space they can share.

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I think that too many people, they gloss over the most difficult parts of their journey.

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And then the version of the successful entrepreneur that we see online, it feels like it was everything was up and to the right.

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100%.

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Plus, even when you tell the story, I think the natural tendency is to share the version where you look like the good guy, you know, because you're the protagonist of your own story and you're naturally thinking, like, I want to remember myself for good.

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In this particular story, you know, the inherent tough part, Scott, I was the CEO of a startup that wasn't doing so well.

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And just right there, you have a little bit of moral hazard because your job as CEO is to make the whole world think how awesome your company is.

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And if you privately know it's not doing that well, you know, there's a bit of ethical gap.

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And so my co-founders and I arrived at Apple headquarters.

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We had a meeting with Steve Jobs, which we all just idolized.

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So this was like a...

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You know, life life moment getting to meet him.

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And the whole first half of the meeting went really well.

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He was leaning in and really liked us.

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And it ended with him saying he'd like to buy the company.

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And his, you know, his one of his top lieutenants, Eddie Q, was there.

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He said he'll let Eddie do the negotiation and figure out the details.

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My first mistake was I should have just kept my mouth shut and be like, thank you so much.

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I'll work with Eddie, which is what he asked us to do.

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But I was so impatient and nervous.

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So I asked him, like, what amount was he thinking?

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You know, like, what range of money?

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And we had raised money two years earlier at $50 million valuation.

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And he offered us $50 million.

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And so my heart sank.

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I was like, oh my gosh, two years of work.

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My whole team, my investors have gotten like no premium on this.

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And so I said, Steve, I think we're worth three times that.

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And then I thought that wasn't strong enough.

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Maybe I can trick him into thinking we have another offer.

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So I changed my body, my like posture.

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And I said, actually, Steve, I know we're worth three times that.

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And he, this distinction between I think versus I know and like my body language, he completely keyed in.

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and called me out.

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He was like, are you trying to suggest you have another offer?

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Bullshit.

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And he just straight up, like, looked into me and I just melted.

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And I could tell at that instant, the deal evaporated.

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I mean, it took some additional, you know, like, there were some ongoing conversations.

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But the, yeah.

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And the lesson for me actually was twofold.

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I mean, I think you should be strong when you're negotiating and you should try to get more.

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But

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For me, it was a bit traumatic.

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But the real deep lesson is I think I was – I realized that perhaps I am BSing other people in more places than I'd like to admit.

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You know, that this wasn't just a one-time thing.

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Like if he could tell that I was trying to –

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kind of convey something maybe other people have that same feeling towards me and just aren't saying it to my face.

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And it really made me have a reckoning with I need to be the type of person that I'd be proud of and still show optimism and confidence but not in a way that looks scammy.

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It's tough because the founder is such a it's so lonely to be a founder.

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And you're just trying your best and you feel like the weight of the world is on your shoulders and

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like when you said that to him, you didn't do it maliciously.

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You're like, listen, I think you genuinely thought like your company is worth this much.

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It was kind of like a white lie, right?

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Like it's, you know, like I'm doing the best for my shareholders, my investors, my employees, but there's no playbook for that.

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And nobody talks about the tough decisions that founders have to make.

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So you in that moment, like you just thought like, you know what?

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I'm just going to try my best.

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I'm going to get this deal done.

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And everyone's going to get taken care of.

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And nobody told you how to do it differently or better.

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I think that it's just tough.

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It's very tough for founders.

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You're right.

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And the loneliness, you really hit on it.

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The loneliness comes from having...

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you know, aspects to your experience that you just can't talk to other people about.

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You know, if it's people who are not part of your company, they don't even like they're not part of the effort.

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So they don't have context.

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And within your company, you know, like if you're the if you're the head of the company, you can't go saying.

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I think we're, I think, you know, you have to project a level of confidence and optimism.

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And so if there's a, if there's a part of you worried that this isn't going well, you just have to deal with that somehow.

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And, and that's, that is very lonely.

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With this particular encounter, I was bluffing him.

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I mean, I was hoping we could get the number up, but there was no part of me that felt confident we were worth $150.

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It was like, if I project confidence and make him think we have another offer, we'll get there.

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And, I mean, I was trying my best, but I don't want to kind of make it seem like this was the right way to run things.

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The funny thing though, Scott, is like, I mean, maybe not funny, like from that happened, you know, more than a decade ago.

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I replayed that episode in my head every single week.

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It truly was like a trauma for me where I was like...

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You know, why did I do it this way?

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What if I had said this?

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Then he would have said that.

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And I mean, for years, when I'm least expecting it, I'll be like washing the dishes or folding laundry.

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And I would just bring back to that scene where I screwed up that deal.

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And it was just like something I hadn't let go of.

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And...

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You know, and I mean, a lot of this is just self-imposed, right?

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Because I had such a big, you know, big loss and I hadn't gotten past it.

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And talking about it, you know, publicly completely cured me of that.

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Suddenly I was like, you know what?

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I'm, you know, I'm not ashamed of it anymore.

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There's not something I haven't processed anymore.

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I've put it out there and I'm moving on.

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And I think that talking about it really helps a lot of founders because then they understand the stuff that they're going through and the stress they're dealing with, whether or not it's a situation like that.

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I mean, like there's so many different things where –

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those hard stories and those lowest moments in people's careers are not discussed publicly.

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So then the founder, when they're going through it, they don't have a reference point.

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They don't know how to deal with it.

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They don't know when things aren't going right in their company, how they should act because they feel like they're alone.

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So I guess the question, and also the issue, the real issue is, um,

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I think founders are not, they're not like marketed to, but they're marketed to a degree to act a certain way, to hype things up, to be hyperbulous.

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And then you see that it blows up in some people's faces, right?

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So I think that when you talk about, this is how you should act, this is what happens when you don't act the right way, you can blow up the deal at the sale of your company.

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This creates a healthier environment and mindset for a founder who's just getting started.

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And by the way, negotiation is the particularly – it's something you just don't get many reps, you know.

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Like how often are you – maybe when you raise financing, you get to negotiate.

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But what is that, once a year?

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You know, it's just something where it's like an ultra-high-stakes poker hand.

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Yeah.

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And you have, you know, you get to like play one hand a year or one hand every other year.

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And, yeah, so it just leads to a lot of pressure and not a lot of practice to prep for it.

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You've spoken about this deal.

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This made you go back, look at your life.

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You were looking at all these other places where you're very, you're candidly very tough on yourself because you said this one particular, this one particular event happened.

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It made you look at all these places in your life where you were dishonest and then like reevaluate.

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Yeah, I wouldn't say my whole life, but I think as the CEO of this company, we had a at the time the company was called I Like.

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It's forgotten now, but we were somewhat of a high profile company.

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We were getting press coverage and I was doing my best to kind of.

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You know, to like expand that and milk that and try to create a image for the company that was that was really positive, which a CEO should do.

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But you can easily get caught up in that and start, you know, believing your own story and forget when it departs from reality.

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Yeah.

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And I don't remember like a specific thing, but it's that I, you know, I mean, I was looking for partnerships and potential investors or acquirers because we were worried that we were not going to make it and we wanted to find some exit.

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And so, you know, I just had this worry that if this person with one sentence could see through me, what if other people are also forming that opinion off who knows what I might have said.

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And the real lesson is you can still be strong in a negotiation without saying something that implies, you know, something you don't have.

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I mean, if I'd simply said we won't accept less than three times that, that's like about what we will do or won't do.

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Not about – I mean, I didn't say we had another offer, but I definitely was trying to trick him into thinking that.

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I was 100% hoping that's what he would take away.

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And, you know, and that's not necessary because, like, Apple doesn't care whether or not we have other offers.

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It only comes down to will we accept what he's offering.

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And, yeah, there are ways to be strong without misleading.

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What's the lesson for an entrepreneur right now?

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So they...

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How do you, how do you be strong without, because I think that a lot of people feel like they have to project that they're the best, they're killing it, everything's working.

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And it's, it's difficult to be vulnerable with your investors with when things aren't going right.

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So what's the lesson to a founder?

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Like how should they operate?

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How do they, how do they be vulnerable with somebody and be honest without killing their chances of being successful?

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It's a great question.

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And I think the, um,

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There's a difference between being vulnerable and being weak.

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And I would actually say it takes extra strength.

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It shows a sense of groundedness and comfort with yourself and confidence to be vulnerable.

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And, you know, I don't mean vulnerable in terms like, oh, help me, I'm struggling.

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I just mean being able to face whatever you're facing and say it truthfully and then still project, I'm betting we'll get through this.

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I, you know, this is what we're betting on.

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This is what gives me hope.

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And I would actually argue it takes a stronger person to be able to show weakness.

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You know, hiding weakness is actually a defense mechanism.

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One of the people who, if you pay attention, actually really shows this very clearly, although maybe most people won't think of him as showing vulnerability, is Elon Musk.

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If you look at videos of him in the early days of SpaceX – sorry, of Tesla –

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he routinely would just say straight out, this will probably fail.

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Like that was like a sentence you'll see in interviews, you know, or, you know, with SpaceX, with some of the rocket ships, I mean, these are highly high-risk missions.

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The sentence he'll often say is, the probability of success is more than zero.

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It's uncertain.

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Right.

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But it's not impossible.

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So he would like openly put the focus on this may not succeed.

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In fact, it's probably not going to succeed.

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And, you know, and trying not to kind of hide that risk and uncertainty, but just facing it and doing it with a sense of hope.

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And, you know, and that's, I think, actually stronger than trying to pretend like there is no risk or that you have everything, you know, like, you know how everything's going to turn out.

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After you went through this and you sort of like take like a pause for a second, you reevaluate how you deal with people across your career with your business.

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What's the lesson that you learned about yourself that you want to leave with a founder who's just starting out?

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Hopefully they don't have to go through this the same way you went through.

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I'd say ultimately it's about courage.

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The thing that I think...

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that causes you to perhaps, you know, hide the truth or things like that is often like some fear of the repercussion.

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And which is why I think it takes actually extra strength not to not to hide it.

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And the one of the biggest lessons I've learned in general is I make the most mistakes when I have a scarcity mentality, when I'm

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Like basically, I'm worried that it won't work out.

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And I've made the best decisions when I had an abundance mentality, when I was just confident that, you know what, even if things aren't good right now, I know it'll work out well.

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And if you're, it's more easily said than done, obviously, because sometimes you just know you're not going to do well.

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But if you try to stay in this zone of, like, long-term, I am confident, I'm going to be fine, and things will be fine, it'll enable you to make better decisions.

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And if you have anxiety and just, you know, nerves constantly, it tends towards making worse decisions.

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Do you feel like it's smart for...

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if an entrepreneur, if they know they get stressed out when, um,

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Everything's riding on this one opportunity kind of like what was going on with with Steve Jobs like this was like the exit.

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This is the opportunity Is it smarter to maybe?

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like not move as fast Create more opportunity for yourself and then because you have more opportunity you actually operate a little bit better and a little bit more confidently like if you had a

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instead of just one offer, like four or five offers, or if you don't have just one customer that's driving 80% of your revenue as a startup, but you diversified a little bit more, is that a smarter way to build your business and just operate in general?

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For sure.

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I would just say it's more easily said than done.

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So yes, it's always better to have multiple options and to have...

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If there's a way to kind of eliminate the risk, great.

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But when you're facing risk that you couldn't eliminate, the important thing still is to find a place of... You don't have to overcome the risk.

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You don't...

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you can't like have false certainty, but at least find a place of comfort so that you're not projecting fear and anxiety and nervousness and, you know, because people can detect that and it affects decisions.

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And I think for each person, it kind of depends where you get comfort from.

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It might be from working out.

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It might be from meditating.

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It might be from playing music.

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It

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Go to a place where you're like, you know, everything is going to be fine.

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And I'm not going to, you know, like allow this scarcity mentality, this fear of the unknown to, you know, to affect my decisions and to affect my communications.

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with Neo and some of the founders you work with, now that I understand sort of your worldview

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you find excellent founders, obviously, but a part of what it seems like your job is, is to not entirely be a therapist, but like help people control and conquer their own mind.

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Is that something that is like a huge piece of your investment philosophy?

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Like, okay, you have a great idea, you're the right, you know, founder market fit, whatever the, whatever, I think there's a few different things you look at, we can go through them.

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But is helping founders conquer their own mind like a very important piece of them being successful and something that you let them know this is what we're going to work on together?

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I love that you picked this up.

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It is.

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Although I don't think we say it as clearly as you just said it.

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So I am really, really grateful you're noticing this.

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But yeah, I mean, I have a whole litany and wealth of my own painful lessons probably because I've done –

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I've taken more risks than ordinary people and end up in hot water more often.

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But I'd say that a big part of working, especially with first-time founders, especially with young founders, is helping them overcome the limits that they are putting on themselves or the fears that they have to get over.

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The biggest mistake I see young people making is not betting on themselves enough.

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And really, this was, I'd say, my biggest mistake.

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You know, when I was younger, early in my career, was essentially not believing in myself enough and not wanting to take risks of betting on myself.

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And ironically, it's the high-performing students who are most prone to this fear of failure.

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Because if someone's never gotten an F in their life, if they've, you know, like always, you know, done the extra work to get straight A's, they're afraid of a B or a C. They, like, literally never experience it.

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And so they're trying to take the path that will just avoid any sort of, you know, any sort of setback.

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And that's actually not the best way to run business decisions.

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You need to, once in a while, do the thing that scares you a bit, where you're like, this could totally fail, but let's see what happens.

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And so, yeah, a big part of my team and my philosophy at NEO is to help people conquer their minds, to take those decisions where –

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Part of them thinks this might not work out, but part of them thinks if it does work out, it would be huge.

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In fact, the name Neo of our company is kind of tied to this conquering of your mind.

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If you want, I'll tell you that.

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Please, yes.

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The connection, if you've watched the movie The Matrix.

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Of course.

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So I named the firm Neo after the hero of that movie.

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And if you pay attention to...

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What's going on in that story?

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I mean, most people remember the thing about robots fighting humans, AI, etc.

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But the internal story, the character arc, he starts out as a software engineer at a big corporation.

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So actually pretty classic.

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starting point of someone about to become a founder of a tech startup.

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And he has a choice between the red pill and the blue pill.

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The blue pill is stay in your safe life as a software engineer.

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Red pill is enter this world of uncertainty.

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You literally don't know what lies behind it.

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See how far the rabbit hole goes.

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And then the whole arc of the movie is...

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these mentors telling him, you're the one, you're going to save humanity.

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And him privately telling himself, I don't think I'm the one.

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Like, I do this task, I fail.

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There's this jump across the city block and he falls and he's trying to overcome his own like imposter syndrome and like

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fear of failure and or to prove to them that I'm not the one like get me out of here so um and and they're trying to give him the courage that no you are the one just you know you can do it and the movie is like about his overcoming that um that fear of failure and then doing things facing facing risks that ordinary people are afraid to face

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And yeah, to me, that's a real allegory for the founder's experience and founder's journey.

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And you achieve like your true potential when you're able to take on things that felt a little bit outside of your reach.

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That's interesting because this is why it's very cliche, but the smartest people are not always the most successful people because they don't take risk.

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100% yes.

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And you said the biggest issue with a lot of people, especially smart people who overthink everything, they don't bet on themselves, they don't take risk.

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Talk to me about your relationship with risk and sort of the first moment you ever bet on yourself.

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You know, I was thinking the analogy, I love games and it's, you know, chess versus poker is an interesting analogy.

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The smartest people are trying to play like chess.

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They're thinking I can plan every move ahead and I can see what the other person, you know, I can literally figure out the answer just using, you know, deductive power.

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Whereas poker is like, I don't have all the information.

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I do my best, but I do some stuff based on instinct and some stuff based on, you know, taking a bet.

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And real life and business is more like poker, you know.

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And if you're trying to figure out every move, first of all, you just take too long to figure out decisions.

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You sometimes...

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Just need to decide based on the limited information you have.

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But you're also not building the muscle of how to, you know, how to do something brave that requires getting over your fears.

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So it's hard for me to remember first bet, like you said.

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I mean, I did a startup one and a half years out of college, and that was very much betting on myself.

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back then we didn't have VC money, there weren't accelerators.

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Doing a startup meant living off savings, like going to zero and very much just draining my savings account.

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And I had grown up financially insecure, so I was really worried about, will I have enough money to take care of my parents?

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So that was a big bet on myself.

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I would say if I look at each of these, each tough, like high-risk decision I made, I think was easier because I had made a smaller one before.

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And the real lesson I would say is that to get to where you're taking big bets, you can build courage by taking smaller bets.

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And I've had kind of a mantra, if I look back across my life, of if I have a few choices and one of them scares me a bit,

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Maybe I'll do that one.

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And it takes some forcing myself to do it, but I've literally tried to...

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When I see an option that scares me a little bit, I push myself towards it.

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So I'm actually constantly daring myself, even with little things, do this little thing that other people wouldn't do.

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Choose this path that...

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is the riskier path because every time you overcome even the smallest, you know, sense of fear or risk, you're building that muscle.

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You're making yourself more able to do it.

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I rock climb for this reason as well.

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I, um, I found that rock climbing is an amazing, it's both a good way to get in shape, but it's a great way to conquer your mind.

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Now you've found that your whole life has been on the other side of the thing that scares you.

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You lean into that.

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You gravitate towards the things a little bit riskier, a little bit more uncomfortable.

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Backing up, that first company started with no savings, no accelerator, no VC money.

332
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And you were worried about running out of money.

333
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You don't have anything to take care of your parents, your bootstraps completely.

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say somebody is in that situation and they don't feel like they have access to VC money, it's maybe not the norm for them.

335
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How do you reduce the risk in your mind a little bit just so you can take that first step?

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Because I think that the biggest issue people have is that first step.

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It's the leaving the safety of corporate and then starting a company.

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Or it is truly starting your first company with no cash in the bank.

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And I think that once they get on that flywheel, I think life will be a little bit easier and then they'll take the next risk and the next risk.

340
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But just your advice to that individual who's just starting taking that first risk, they felt like they've never taken a risk before in their life.

341
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How do they get over that mental hurdle?

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Yeah.

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First of all, it's more easily said than done.

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You know, I do think going, you know, just thinking of myself is that

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Taking smaller risks builds up your courage.

346
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Not that it makes that one big leap easier, but if you have taken other lower stakes risks, whether you succeed or fail, it helps you become less afraid.

347
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But...

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With respect to starting a company, I would say risk may not even be the best word.

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Think of it as just uncertainty because on the other side of this leap, yeah, it could fail, but it could also be a huge payoff.

350
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And I would say one thing logically is that not taking those leaps –

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is almost guaranteeing that you're not going to have that big payoff.

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00:31:03.795 --> 00:31:12.499
It's going to be, you know, perhaps a more predictable path and predictable life, but you're probably not going to be the most successful one of your friends.

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The ones who are successful are the ones who take the options that scare you a little bit.

354
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And then the other thing I'd say is as a founder, you unfortunately can't diversify.

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You only have, you know, it's an all in bet.

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It's you have one career, but you can diversify over time.

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And, um, meaning if you go all in and it fails, your life doesn't end.

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You can, you can take another bet and another one, hopefully over three or four, you know, one can pay off enough to be worth the others.

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And, um, yeah.

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And it's an interesting thing to separate that, separate your identity from the startup.

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And this is what I mean by this is like, if you're a founder, this is who I am, you know, and like you think in your mind, everyone associates me 100% with this one company.

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And then if the company fails, you know,

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That means I'm a failure.

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And it's like, it's not just about financial, like whether you can continue.

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It's whether everyone is going to see you as that failure guy.

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And the reality is that's not how other people see you.

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Other people were like, oh, yeah, he took a swing and he missed.

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But it's like now it's in the past.

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And now whatever you're doing next is what you're doing next.

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And this for me actually after, I mean, that company with the Steve Jobs story ultimately wasn't successful.

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And for a long time, I was kind of depressed.

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I was like, I'm a failure.

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And it took me a while to realize no one else sees me that way at all.

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You know, my first startup had been successful.

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Most people saw me as a successful person.

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I mean, I had done quite well in other things, but I was putting this huge weight on myself now.

377
00:32:56.819 --> 00:33:05.363
And so I'd say it's helpful to realize that doing a startup, even though it might feel like an all-in bet with your identity, it's not.

378
00:33:05.563 --> 00:33:09.964
Just think of it more as like taking a swing in baseball.

379
00:33:10.065 --> 00:33:11.345
You have more swings.

380
00:33:11.545 --> 00:33:11.745
Yeah.

381
00:33:11.965 --> 00:33:15.247
It's like the worst case scenario, you just go back and get a job.

382
00:33:15.487 --> 00:33:16.027
Absolutely.

383
00:33:16.587 --> 00:33:22.129
And by the way, the same thing, I spent a lot of time convincing people to join startups.

384
00:33:22.510 --> 00:33:26.311
And I want to, you know, it's just as valid a form of betting on yourself.

385
00:33:26.871 --> 00:33:34.394
You know, we glorify being the founder because like, you know, you're the, that's the ultimate all in kind of bet on yourself.

386
00:33:34.494 --> 00:33:35.355
But if you have a...

387
00:33:36.035 --> 00:33:57.148
comfortable job or even like let's say you have a prestigious job at a place that's doing great and then there's a startup that you think this might be amazing and they want you to join them as employee number two or ten that also feels highly risky but I'd say first of all that is another valid form of betting on yourself and

388
00:33:57.568 --> 00:34:02.194
I mean, you're betting on the other 10 people, but, you know, you're one-tenth of the team.

389
00:34:02.254 --> 00:34:06.759
That's much more betting on yourself than if you're one of 1,000 or 10,000.

390
00:34:06.859 --> 00:34:11.885
And then a lot of people have this aspect of, like, I'm leaving this –

391
00:34:13.847 --> 00:34:23.873
whatever wealth I have in my current job, my salary or my stock, I'm losing that to whatever this option might be.

392
00:34:24.554 --> 00:34:31.739
And the way I encourage people to think of it is that think of that as wealth that is part of you.

393
00:34:32.899 --> 00:34:36.121
If a job is paying you a high salary, it's because you're worth that.

394
00:34:37.062 --> 00:34:39.244
that value doesn't disappear.

395
00:34:39.444 --> 00:34:41.065
You're taking it with you to the new place.

396
00:34:41.825 --> 00:34:51.912
And you may not be getting the same salary, but you're getting equity, you're getting ownership that, you know, you're getting paid in a different currency whose value is unpredictable.

397
00:34:52.492 --> 00:34:56.415
And it could be much more, it could be less, but the value is still in you.

398
00:34:56.715 --> 00:34:58.716
And if it pays off, awesome.

399
00:34:58.796 --> 00:34:59.477
And if it doesn't,

400
00:35:00.097 --> 00:35:05.859
You go to a new job and you bring that value with you and, you know, get back the same salary you had before.

401
00:35:06.019 --> 00:35:17.083
It's so interesting how even if you fail as a founder or if you join as an employee and the company fails, to a degree your identity is wrapped up in this failure like you mentioned.

402
00:35:18.163 --> 00:35:23.665
But you are ironically incredibly more valuable as an individual because of what you've learned.

403
00:35:23.685 --> 00:35:23.885
100%.

404
00:35:25.005 --> 00:35:30.448
So the rest of the world, the market, whatever, like they're like, oh, my goodness, they've built this thing.

405
00:35:30.808 --> 00:35:32.669
They've learned all these expensive lessons.

406
00:35:33.089 --> 00:35:36.871
This is going to be the most useful person I can ever work with because look at all the stuff they've gone through.

407
00:35:36.891 --> 00:35:39.032
They don't want to make those mistakes a second time.

408
00:35:39.473 --> 00:35:44.295
Plus, you've showed that that you're a self-starter, that you could take ownership.

409
00:35:44.815 --> 00:35:50.999
You know, people prefer employees who behave like owners, who don't just show up and behave like workers, who –

410
00:35:51.979 --> 00:35:53.700
act like they care about what's happening.

411
00:35:53.901 --> 00:35:59.285
And if you've been a founder, you're going to bring that ownership mentality to wherever you go.

412
00:35:59.765 --> 00:36:02.287
So yeah, absolutely actually makes you stronger.

413
00:36:02.908 --> 00:36:17.099
You've said that when you're looking at a founder and you're trying to figure out who you'd like to invest in and work with, technical ability comes first and then magnetism, risk, and mischief.

414
00:36:17.919 --> 00:36:18.880
My gosh, thank you.

415
00:36:18.900 --> 00:36:19.921
You've done your research.

416
00:36:20.181 --> 00:36:21.302
These are very interesting.

417
00:36:22.743 --> 00:36:23.143
Of course.

418
00:36:23.203 --> 00:36:30.489
No, I find it fascinating how you look at founders, how you understand who's going to work and who's not the best fit.

419
00:36:31.169 --> 00:36:36.513
I want to understand what these ideas are, because I've never heard of an investor.

420
00:36:36.934 --> 00:36:40.156
I've heard them discuss tactical ability and risk tolerance.

421
00:36:40.196 --> 00:36:44.139
These are a little bit more common, but magnetism and mischief.

422
00:36:44.500 --> 00:36:46.261
But go through all of them because I think they're fascinating.

423
00:36:46.341 --> 00:36:46.841
What do they mean?

424
00:36:47.322 --> 00:36:48.503
Well, first of all, I'll say...

425
00:36:50.324 --> 00:36:52.646
you know, a lot of it is just my own gut feel.

426
00:36:52.666 --> 00:36:55.288
It's not like I have a checklist of like- Magnetism.

427
00:36:55.568 --> 00:36:56.369
Yeah.

428
00:36:57.209 --> 00:37:04.115
So sometimes when you're with someone you just know, and you can't put a word to it.

429
00:37:04.555 --> 00:37:15.664
That being said, I work with a team, and it helps to have words, and it helps to kind of say, this is what I saw or I'm looking for, so that the other people on the team can learn, and can, you know, and-

430
00:37:17.065 --> 00:37:22.407
So, yeah, so coming up with these words for us was an exercise, actually.

431
00:37:22.447 --> 00:37:26.569
It's not like I, you know, have always had the same checklist.

432
00:37:27.109 --> 00:37:32.871
So the technical ability is a unique prerequisite for us.

433
00:37:32.891 --> 00:37:34.232
There's a lot of VCs who...

434
00:37:35.172 --> 00:37:40.036
want a CEO who's just an incredible visionary and may or may not be technical.

435
00:37:40.456 --> 00:37:53.487
And we, and by the way, if, if, if there's a founding team where the CTO is highly technical, the CEO doesn't have to be, you know, we're, uh, uh, but somebody on the founding team must be highly technical.

436
00:37:53.607 --> 00:37:55.848
We invest in, in technology companies.

437
00:37:56.589 --> 00:37:57.209
The, um, the,

438
00:37:58.030 --> 00:38:03.394
But having that aside as a prerequisite, I would say the most important thing is what we call magnetism.

439
00:38:04.034 --> 00:38:08.738
And I use that word because I don't want to use a word that, say, like charisma.

440
00:38:09.078 --> 00:38:12.240
Charisma is great, but I'd say that's just one form of magnetism.

441
00:38:12.661 --> 00:38:20.907
You can have somebody who is flamboyant and loud and really charismatic, or you could have somebody who's almost shy and muted and...

442
00:38:21.507 --> 00:38:25.028
but has something about them that draws others to them.

443
00:38:25.248 --> 00:38:29.069
And so I try not to have like one template.

444
00:38:30.110 --> 00:38:38.412
But the question I'm ultimately always asking myself is, if this person started something, how many of their smartest friends would follow them?

445
00:38:39.012 --> 00:38:42.173
And would I follow them, et cetera?

446
00:38:42.554 --> 00:38:43.734
And I think, for example...

447
00:38:44.494 --> 00:38:48.659
When I, the first time I met Michael Truel, uh, was when he was 19.

448
00:38:48.719 --> 00:38:51.382
He went on to start Cursor, um, three years later.

449
00:38:51.402 --> 00:38:54.425
Um, he's kind of a shy person.

450
00:38:54.465 --> 00:38:57.148
He's, and he's very, I'd say very quiet.

451
00:38:57.428 --> 00:39:03.394
He's somebody who could totally be in the back of the room or, you know, like kind of disappear a little bit.

452
00:39:03.754 --> 00:39:06.858
Well, not physically, he's so tall that he would never disappear.

453
00:39:07.378 --> 00:39:22.282
But, um, but he's not a charismatic or flamboyant person, but he just had this quiet confidence about him that was almost comforting, you know, like just to what I was saying before, I guess, abundance mentality.

454
00:39:22.302 --> 00:39:25.222
He had this sense of, he knows where he's going.

455
00:39:25.282 --> 00:39:26.243
He knows where he's headed.

456
00:39:26.683 --> 00:39:31.124
He knows he's going to do great things that just makes you want to, to follow him.

457
00:39:31.784 --> 00:39:32.184
Um, yeah.

458
00:39:33.484 --> 00:40:00.276
the i have another great story about magnetism but the to the other points the um the point about risk taking is just somebody willing to take the path less traveled and you can look at evidence of that what choices did they make you know if if every job they've had was kind of pursuing prestige and doing whatever was the safe you know path to success you know that's a little

459
00:40:03.498 --> 00:40:08.484
And it's also in terms of if someone is pitching a startup, how ambitious is the startup?

460
00:40:08.624 --> 00:40:13.210
Are they doing something that is, you know, kind of incremental and, you know, safe?

461
00:40:13.470 --> 00:40:17.455
Or is it absolutely crazy, but it will be huge if it succeeds?

462
00:40:17.735 --> 00:40:20.198
And I prefer people who are taking bigger swings.

463
00:40:21.741 --> 00:40:30.968
And then lastly, with mischief, it's a little related to risk, but it's basically willingness to question the status quo, including willingness to question the rules.

464
00:40:31.829 --> 00:40:35.551
I don't want to bet on people who are criminals or fraudsters.

465
00:40:35.651 --> 00:40:40.375
Obviously, I need to trust people and I need to believe that they will do things that way.

466
00:40:40.475 --> 00:40:42.856
will be successful and not end up in jail.

467
00:40:42.916 --> 00:40:51.958
But there's a difference between Theranos and just breaking a couple, the way it's always been done mentality.

468
00:40:51.978 --> 00:40:52.318
Exactly.

469
00:40:52.598 --> 00:41:01.500
So the Y Combinator application has a question, or at least used to, I don't know if it still does, talk about a time when you've hacked the system in some way.

470
00:41:02.140 --> 00:41:06.441
So that doesn't necessarily mean committing a cybercrime, but it just means...

471
00:41:07.221 --> 00:41:10.966
Finding some way around things that other people might not have seen.

472
00:41:11.086 --> 00:41:18.575
And that's the key thing is like, you know, there's some people where if they're told this is how it's done, they don't ask any questions.

473
00:41:18.615 --> 00:41:19.857
They just stay in that lane.

474
00:41:20.477 --> 00:41:23.461
Whereas there's others who are like, well, why is that the rule?

475
00:41:23.661 --> 00:41:25.423
How come it's never been done this other way before?

476
00:41:25.443 --> 00:41:25.884
Yeah.

477
00:41:26.024 --> 00:41:30.887
I'm, you know, and if there's an obstacle, they're like, I've got to find a way around this obstacle.

478
00:41:31.407 --> 00:41:31.988
How do I do it?

479
00:41:32.068 --> 00:41:34.449
Do I go around it, over it, break it?

480
00:41:35.150 --> 00:41:35.750
What do I do?

481
00:41:36.270 --> 00:41:42.394
And, um, you know, an example that's been very, one of my most successful investments ever is Kalshi.

482
00:41:43.095 --> 00:41:49.499
Um, they, when they pitched Kalshi, um, it was not clear that it was legal or not.

483
00:41:49.879 --> 00:41:50.860
Um, uh, yeah.

484
00:41:51.620 --> 00:42:01.762
To be clear, they had no intention of doing anything illegal, but they came forward and said, we think we've discovered a path to do this that's compliant with all the laws.

485
00:42:01.902 --> 00:42:06.663
And it falls under this Commodity Futures Act.

486
00:42:06.843 --> 00:42:11.124
No one's tried this approach to creating a legal prediction market.

487
00:42:11.984 --> 00:42:14.285
And it may not exist.

488
00:42:14.825 --> 00:42:16.047
It may not turn out to be legal.

489
00:42:16.107 --> 00:42:19.029
Somebody may strike it down, but we don't see a reason why it's not legal.

490
00:42:19.490 --> 00:42:20.811
And we want to bet on it.

491
00:42:21.311 --> 00:42:28.918
And the crazy thing, Scott, they had so much trouble finding a law firm to represent them.

492
00:42:29.358 --> 00:42:37.225
I think they called like 40 law firms and got 40 rejections before a lawyer was willing to say, okay.

493
00:42:37.906 --> 00:42:39.648
And I asked Tarek, like, okay.

494
00:42:40.448 --> 00:42:41.208
Why did you keep...

495
00:42:41.769 --> 00:42:46.971
I mean, I would give up after 10 law firms told me, sorry, that's not going to work, right?

496
00:42:47.331 --> 00:42:48.532
What led you to keep going?

497
00:42:48.932 --> 00:42:53.114
And he said, well, first of all, we had read the laws and we understood it.

498
00:42:53.755 --> 00:43:05.300
And if anyone had said, here's the law you'd be violating or like here's like a proof of why it's illegal or why it wouldn't work out, we would have been satisfied with that.

499
00:43:05.680 --> 00:43:08.142
But every one of them had some variation of like...

500
00:43:08.982 --> 00:43:10.182
It's never been done before.

501
00:43:10.943 --> 00:43:13.944
And he said that just gave us actually more motivation.

502
00:43:14.184 --> 00:43:21.766
It was like every – if 10 law firms couldn't point to the flaw in our logic, maybe our logic is good.

503
00:43:22.167 --> 00:43:31.570
And so I guess I like people like that who just will keep pushing for some way around the rules that are constraining other people.

504
00:43:31.750 --> 00:43:33.150
Tell me the story about magnetism.

505
00:43:33.170 --> 00:43:34.311
What's the other story about magnetism?

506
00:43:34.371 --> 00:43:34.731
Oh, yeah.

507
00:43:35.471 --> 00:43:42.836
This is one of my favorite people in the world is Emily Cohen, who's now an executive at Cognition.

508
00:43:42.856 --> 00:43:48.599
But she joined my team and was one of our investors and became a partner before she went there.

509
00:43:49.160 --> 00:43:51.021
It's a story from when she was a college student.

510
00:43:51.701 --> 00:43:52.722
She went to Stanford.

511
00:43:53.843 --> 00:43:57.385
And, yeah, it has nothing to do with business.

512
00:43:57.965 --> 00:44:00.607
So imagine a picture of Stanford student.

513
00:44:01.468 --> 00:44:04.249
And she and her friends were up really late partying or whatever.

514
00:44:04.289 --> 00:44:05.170
And she was like, oh, my God.

515
00:44:05.630 --> 00:44:17.019
And she said to the group, hey, everybody, let's like wake up early, like 5 a.m. and drive out to Half Moon Bay to see the sunrise together.

516
00:44:17.539 --> 00:44:24.765
And so she got like a dozen people of her fellow Stanford friends to wake up at 5 a.m., like barely sleep.

517
00:44:25.505 --> 00:44:28.106
and get in cars and drive all the way to Half Moon Bay.

518
00:44:28.627 --> 00:44:36.370
And, you know, so they all wake up and drive out there and get there to the ocean.

519
00:44:37.131 --> 00:44:42.353
Now, Emily had grown up on the East Coast, where the sunrise is at the ocean in the East.

520
00:44:42.894 --> 00:44:45.095
But they arrive here at the West Coast.

521
00:44:45.995 --> 00:44:47.818
And they're like looking out at the ocean.

522
00:44:48.519 --> 00:44:49.681
There's no sunrise.

523
00:44:49.721 --> 00:44:50.883
The sun is behind them.

524
00:44:51.443 --> 00:45:00.136
So to me, it's just I'm imagining this whole group of Stanford students, the smartest kids in the world, followed this girl to do something so idiotic.

525
00:45:00.777 --> 00:45:09.564
But it just reflects the sheer willpower and, you know, willingness to do something because someone magnetic is doing it.

526
00:45:09.884 --> 00:45:11.225
This one's kind of a joke story.

527
00:45:11.425 --> 00:45:12.526
But it's so, but I mean.

528
00:45:12.566 --> 00:45:13.326
It isolates.

529
00:45:13.687 --> 00:45:14.768
It's magnetic.

530
00:45:14.788 --> 00:45:19.971
You get people like you have an idea and just you galvanize people around this idea.

531
00:45:20.212 --> 00:45:20.392
Yeah.

532
00:45:20.572 --> 00:45:21.373
That's so funny.

533
00:45:21.433 --> 00:45:22.674
It's such a funny story.

534
00:45:23.054 --> 00:45:23.854
I've always thought that.

535
00:45:24.815 --> 00:45:26.597
a really, a really strong signal.

536
00:45:26.617 --> 00:45:33.903
And it's something similar to what you're talking about with magnetism, really strong signal of a founder or I don't operate anywhere close to the level you're at.

537
00:45:33.923 --> 00:45:43.092
I write very, very small checks compared to what you guys do, but still a signal is, can that founder get people to work for them for free in some capacity at the beginning?

538
00:45:43.612 --> 00:45:49.437
And that's a version of it's yeah, it's really, um, and the both the best, um,

539
00:45:50.238 --> 00:45:57.102
Jobs or the best people are the things you would do, you know, even if there wasn't a paycheck in it.

540
00:45:57.122 --> 00:46:01.425
The things that because the mission means something or because the people.

541
00:46:01.745 --> 00:46:05.267
Every company has that one process only one person knows.

542
00:46:05.707 --> 00:46:10.249
Someone new joins, asks that person, gets walked through it, none of it's written down.

543
00:46:10.529 --> 00:46:13.310
Then that person's out for a week and nobody knows what to do.

544
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571
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What's the lesson then?

572
00:48:11.852 --> 00:48:19.074
Because if somebody's listening to this and they want to be a founder and they're like, I can't get anybody to believe in me.

573
00:48:19.974 --> 00:48:22.114
How does somebody increase their magnetism?

574
00:48:22.154 --> 00:48:24.955
Because this is almost like a personality trait.

575
00:48:24.975 --> 00:48:26.495
It's a combination of personality traits.

576
00:48:26.535 --> 00:48:28.036
It's not just being charismatic.

577
00:48:28.676 --> 00:48:29.956
It's confidence.

578
00:48:30.316 --> 00:48:33.017
It's belief in your own self, belief in your idea.

579
00:48:40.578 --> 00:48:41.379
what I'm trying to build.

580
00:48:41.900 --> 00:48:42.580
How do I do it?

581
00:48:43.401 --> 00:48:48.327
So I'm glad you asked this, Scott, because you're going to the point that this is something that can be practiced.

582
00:48:48.367 --> 00:48:55.455
This is something, you know, I mean, some people have some inborn, you know, things that are just in their personality.

583
00:48:55.695 --> 00:48:58.358
But just like what I said about overcoming fear,

584
00:48:59.759 --> 00:49:02.281
These are traits you can try to build in yourself.

585
00:49:03.021 --> 00:49:09.844
I think one key thing is try to be magnetic in a way that's honest to yourself.

586
00:49:10.325 --> 00:49:17.689
Like, don't just say, oh, I want to, you know, like role play and adopt someone else's personality.

587
00:49:17.729 --> 00:49:21.550
You need to stay true to what makes you, you.

588
00:49:22.771 --> 00:49:26.253
I think a big part of it is just being comfortable in your own skin.

589
00:49:26.833 --> 00:49:34.375
And, you know, if you're not, people can detect that and it's harder to make them feel good around you.

590
00:49:34.495 --> 00:49:40.276
And so, you know, overcoming your own anxieties perhaps or whatever.

591
00:49:40.857 --> 00:49:46.358
But then I'd say practice, you know, getting people to join your startup is a big leap.

592
00:49:46.658 --> 00:49:50.739
What about getting people to go watch the sunrise with you or, you know.

593
00:49:52.497 --> 00:49:59.700
actually getting reps in of doing things and getting people to follow you is something not everyone does.

594
00:49:59.780 --> 00:50:07.903
You know, there are people who just don't want to, they want to go with the flow, like on every decision, they're like, whatever everyone else is doing, you know?

595
00:50:08.343 --> 00:50:15.726
And, um, it takes a little bit of coming out of your comfort zone, perhaps to, for you to say, this is what we should all do.

596
00:50:16.586 --> 00:50:23.628
And that's something you can get reps on and see how people react and try to improve.

597
00:50:24.168 --> 00:50:30.870
So I think a key part of it, though, goes back to believing in yourself.

598
00:50:31.250 --> 00:50:41.473
And then with respect to a startup, specifically, I think it's easier to hire people to do something that is more ambitious, even if it's more risky.

599
00:50:42.233 --> 00:50:57.720
And this is, I think, one of the really interesting paradoxes is that when you're kind of deciding what business to do or what idea to take, we tend to gravitate towards the lower risk option.

600
00:50:58.640 --> 00:51:02.222
But it's harder to recruit people if you're doing the lower risk option.

601
00:51:02.242 --> 00:51:15.271
Because how do you inspire them that this is worth leaving their prestigious job or their safe, you know, whatever comfort zone they're in to do this, you know, do a startup unless they feel like this is something that inspires them.

602
00:51:15.391 --> 00:51:17.533
And it's actually easier to inspire people.

603
00:51:18.313 --> 00:51:25.121
If you're taking a really big swing, if you're a little bit afraid, but overcoming that fear because of some bigger vision.

604
00:51:25.862 --> 00:51:36.194
And so the risk almost flips because if you're taking on something grandiose and ambitious, it's easier to hire brilliant people to join you.

605
00:51:36.755 --> 00:51:38.276
And once you have a bunch of brilliant people...

606
00:51:38.857 --> 00:51:40.118
maybe it's not as risky anymore.

607
00:51:40.678 --> 00:51:50.964
So, yeah, so I, I mean, I've actually repeatedly seen founders who are doing something that was too safe have trouble recruiting.

608
00:51:52.004 --> 00:51:53.966
And they're like, how come I can't get anyone to join?

609
00:51:54.026 --> 00:52:03.011
And it's like, well, what you're doing is something that the other person is going to look at and be like, I could have started that myself or that's just not inspiring to them.

610
00:52:03.571 --> 00:52:04.732
And the people who are,

611
00:52:06.173 --> 00:52:11.982
And setting up to do these crazy sounding things are the ones who actually are able to recruit the best people.

612
00:52:12.823 --> 00:52:17.731
So your show Confession, this is all about painful lessons that other people have learned.

613
00:52:17.851 --> 00:52:20.956
I want to first understand, why did you choose the name Confession?

614
00:52:21.437 --> 00:52:22.277
It's because it's edgy.

615
00:52:22.897 --> 00:52:26.858
You know, I'm not religious, but it has that undertone.

616
00:52:28.058 --> 00:52:34.899
But it's also, you know, it's about this aspect of getting something off your chest.

617
00:52:35.699 --> 00:52:40.200
And in our case, it doesn't mean something harmful you did.

618
00:52:40.220 --> 00:52:47.581
It just means something that you're, you know, holding back from talking about, you know.

619
00:52:48.022 --> 00:52:49.102
And so...

620
00:52:51.903 --> 00:52:57.246
And it's tied to the therapeutic effect it had for me when I posted the Steve Jobs story.

621
00:52:57.286 --> 00:53:01.949
I mentioned I posted it online and it was really a weight off my shoulders.

622
00:53:02.089 --> 00:53:10.814
I actually want to create a space for tech leaders to unload some story they had that they haven't shared before.

623
00:53:11.074 --> 00:53:14.476
By the way, how many years after the Steve Jobs thing happened did you post this online?

624
00:53:14.516 --> 00:53:15.457
It was more than 10 years.

625
00:53:15.857 --> 00:53:17.958
And that's the first time you publicly spoke about it.

626
00:53:18.018 --> 00:53:20.239
Yeah, 10 or 13 years.

627
00:53:20.279 --> 00:53:23.121
It was 10 years after his death.

628
00:53:23.441 --> 00:53:25.682
It was actually the anniversary of his death.

629
00:53:26.222 --> 00:53:34.607
And the reason was, I mean, I remember I woke up and I picked up my phone and I saw Twitter all over people saying things about Steve Jobs.

630
00:53:35.867 --> 00:53:38.268
how wonderful he was and all their different people.

631
00:53:38.308 --> 00:53:41.449
Like my one awesome experience with Steve Jobs.

632
00:53:41.729 --> 00:53:49.351
And I was like, I had one very terrible experience with him that I mean, that I knew was like a trauma because I'd relive it every week.

633
00:53:49.491 --> 00:53:50.132
And I was like, you know what?

634
00:53:50.332 --> 00:53:51.352
I'm just going to write about this.

635
00:53:52.052 --> 00:53:59.074
And so I was still in bed and I just like, you know, tapped it out on my phone and, and did it.

636
00:53:59.134 --> 00:54:04.995
And, and yeah, and I spent the next two days having my phone blow up with like Twitter responses.

637
00:54:05.015 --> 00:54:05.835
It was just so real.

638
00:54:06.095 --> 00:54:06.355
Yeah.

639
00:54:06.875 --> 00:54:08.256
You've spoken to some incredible people.

640
00:54:08.316 --> 00:54:15.757
So like Satya Nadella, Reid Hoffman, um, uh, Sho Wang out of all these conversations, what surprised you the most?

641
00:54:16.277 --> 00:54:17.418
That's an interesting question.

642
00:54:17.478 --> 00:54:18.918
So I think, uh,

643
00:54:20.628 --> 00:54:35.500
I would say it was interesting how many people shared sort of the same thing I mentioned of this, the loneliness when you privately have worries about things aren't going well and you have to publicly show them as, you know, as positive.

644
00:54:36.140 --> 00:54:40.341
There was a point where Reed talked about his first startup that was unsuccessful.

645
00:54:41.061 --> 00:54:43.402
And he literally said, I felt like a liar.

646
00:54:43.962 --> 00:54:45.742
And it felt terrible, you know.

647
00:54:46.242 --> 00:54:52.444
And that to me, like I don't know if I would put it in that stark terms.

648
00:54:52.544 --> 00:54:59.406
But he was just talking about like he's a founder of a startup and had investors and raised money and so on.

649
00:54:59.426 --> 00:55:03.346
But inside had this sinking feeling that he had to hide from others.

650
00:55:06.708 --> 00:55:28.423
yeah and i guess i'd say it's um i don't necessarily think it's a surprise but i think for for people who watch this podcast hopefully it'll be a good thing is just to see how human people are you know and no matter how successful someone is they still have their demons they still have you know their private insecurities or things like that and um yeah

651
00:55:29.143 --> 00:55:37.190
And I think seeing a successful person open up that way helps give courage to younger people to realize, oh, you know what?

652
00:55:37.950 --> 00:55:39.171
I could be like that person.

653
00:55:39.191 --> 00:55:46.498
Because if you have a perfect role model who's never got any mistake or so on, it's unapproachable.

654
00:55:46.538 --> 00:55:51.542
It feels like, okay, that person is some kind of superhuman and I can't be them.

655
00:55:52.142 --> 00:56:00.410
And I think seeing them as as real, you know, warts and all actually helps hopefully young people think, yeah, I could do that, too.

656
00:56:00.650 --> 00:56:06.816
What are the biggest misconceptions about a super successful entrepreneur or founder?

657
00:56:06.896 --> 00:56:14.163
Like what are the things that you like the similarities in these conversations that you're like, OK, so this is what they actually are like versus what the world thinks they're like?

658
00:56:14.603 --> 00:56:31.291
I think one of the interesting things, even the most successful people within their inner circle, you know, like somebody might be managing a thousand employees or 10,000 employees, but within their inner circle, they're still just a normal person, you know.

659
00:56:31.791 --> 00:56:42.937
And, of course, it's important, like the most successful people have a very strong inner circle and surround themselves with successful people as, you know, your theme.

660
00:56:43.237 --> 00:56:43.517
But –

661
00:56:44.277 --> 00:56:51.643
It's fascinating how their interactions often are not as lofty as you might think.

662
00:56:51.723 --> 00:56:52.684
They'll still have doubts.

663
00:56:52.704 --> 00:56:59.650
They'll still be like, let me ask three of the closest people, is this a good idea before I do it?

664
00:57:01.031 --> 00:57:08.717
And that they're not some kind of superhuman who is, you know, like a lofty general of 10,000 people.

665
00:57:08.817 --> 00:57:09.898
They're just working with their...

666
00:57:11.138 --> 00:57:16.821
10 people and each of those is working with 10 and so on and so forth to a whole organization.

667
00:57:17.541 --> 00:57:32.747
And so sometimes human mistakes happen, you know, and, uh, and it's, uh, it's not because, I mean, it's because everyone's human and they're operating in a way that is not necessarily like some kind of different level than, uh,

668
00:57:33.367 --> 00:57:55.762
than than you or me what are the challenges that that these founders like the the the main things that not the business challenges but what mental hurdles do they have to overcome is it self-doubt is it imposter syndrome like what are the things that everybody's have that has had to overcome at some point to get to where they are

669
00:57:56.362 --> 00:57:59.845
So, I mean, I've now I've recorded a few episodes and I'm releasing them.

670
00:58:00.185 --> 00:58:01.986
I don't know if there's a single common thread.

671
00:58:02.327 --> 00:58:09.412
And and some of them, some of them, I mean, depending on who's listening might be like, this is freaking obvious.

672
00:58:09.452 --> 00:58:12.494
How did this person get to this point without knowing this?

673
00:58:12.514 --> 00:58:12.995
I'll.

674
00:58:15.896 --> 00:58:22.900
I'll give you an example, not to single him out, but I think, so Jeff Lawson from Twilio, I think he would agree with this.

675
00:58:23.620 --> 00:58:29.983
He was sharing, in my interview with him, he shared something pretty substantial.

676
00:58:30.043 --> 00:58:35.285
He built Twilio, he founded Twilio and built it to a $20 billion public company.

677
00:58:35.845 --> 00:58:40.409
And then abruptly, one day, they announced he's no longer CEO.

678
00:58:40.849 --> 00:58:41.370
He's leaving.

679
00:58:41.710 --> 00:58:44.773
And there's no plan for a new CEO.

680
00:58:45.713 --> 00:58:47.215
And it wasn't clear what happened.

681
00:58:47.975 --> 00:58:53.500
And, you know, on my podcast, he shares the full, how it went down.

682
00:58:53.980 --> 00:58:56.121
And I asked him about the lesson he learned.

683
00:58:56.541 --> 00:59:03.184
And he basically said, like, look, I'm at heart an engineer.

684
00:59:03.524 --> 00:59:10.767
I'm really good at building things, really good at coding, really good at solving problems, and had never spent enough time working.

685
00:59:11.027 --> 00:59:26.680
on really like paying attention to some of the human relationships, specifically with his board members, and he had somewhat taken them for granted and, you know, saw some of, you know, like managing his board member relationships, saw that as a distraction from...

686
00:59:27.200 --> 00:59:31.225
what he loved doing, which was the, you know, like the day to day challenges.

687
00:59:31.686 --> 00:59:36.192
And there was, you know, there was a board member he'd never even met in person.

688
00:59:36.252 --> 00:59:44.542
They were in, I think, from Europe and he'd basically had not taken the time to visit them and get to know them.

689
00:59:45.743 --> 00:59:59.770
So he was basically confessing that he had his priorities a little off and putting too much focus on the technology or on the kind of nuts and bolts of product and not enough on human relationships.

690
01:00:01.490 --> 01:00:05.072
There are probably some people who would completely identify with that.

691
01:00:05.292 --> 01:00:06.573
I'm also a total nerd.

692
01:00:06.833 --> 01:00:08.774
I probably have been guilty of that in some places.

693
01:00:09.214 --> 01:00:11.195
But I'm sure you have other listeners who would be like –

694
01:00:12.715 --> 01:00:15.096
Of course you have to become close to your board.

695
01:00:15.156 --> 01:00:17.037
How dumb could you have been?

696
01:00:17.057 --> 01:00:19.498
The guy built a $20 billion company.

697
01:00:19.538 --> 01:00:19.839
Yeah.

698
01:00:20.039 --> 01:00:24.541
How do you get to a $20 billion company without having already learned that lesson?

699
01:00:25.041 --> 01:00:25.281
It is.

700
01:00:25.341 --> 01:00:27.542
So this is actually a really important point.

701
01:00:28.603 --> 01:00:36.487
I think that too often, especially with social media, podcasting, we always think there's like one silver bullet to become successful.

702
01:00:37.348 --> 01:00:38.629
and there's only one way to do it.

703
01:00:39.450 --> 01:00:43.535
And I think that that throws a lot of people off, and it actually makes people hesitant to try.

704
01:00:43.555 --> 01:00:47.921
They think, like, for example, if I'm an introvert, I'm not a good people person, well, I can't build a company.

705
01:00:47.941 --> 01:00:49.363
Or if I'm not technical, then I can't build.

706
01:00:49.683 --> 01:00:51.866
And they always look for reasons why, but...

707
01:00:52.967 --> 01:01:04.358
when you have these honest conversations with these founders, you realize that all personalities have their advantages, their drawbacks, and they can all be successful to a degree.

708
01:01:05.840 --> 01:01:08.942
And he could have continued to be successful if he had seen his,

709
01:01:09.743 --> 01:01:15.507
his own flaws earlier on, not to say that, you know, after 20 billion, I feel like you're good.

710
01:01:16.647 --> 01:01:18.108
You don't have to do too much else.

711
01:01:18.128 --> 01:01:18.849
Jeff's doing well.

712
01:01:18.869 --> 01:01:22.951
I love Jeff and admire him and learn a lot from him myself.

713
01:01:23.031 --> 01:01:29.675
But that is an important lesson for somebody who is maybe less charismatic, a little bit more introverted, doesn't love people.

714
01:01:29.935 --> 01:01:31.996
Okay, well, look at what Jeff's been able to do.

715
01:01:32.156 --> 01:01:34.598
You can still, yeah, lean into your strengths for sure.

716
01:01:34.938 --> 01:01:37.960
But people don't talk about these subjects a lot.

717
01:01:38.160 --> 01:01:46.866
They don't talk about the shortcomings that they have, which actually creates space for somebody who's just starting out to realize what they could potentially do.

718
01:01:48.106 --> 01:01:56.532
So all these, whether or not it's social anxiety, lack of ability to build relationships, self-doubt, imposter syndrome, rock bottom –

719
01:01:57.352 --> 01:02:01.176
How do you get your founders that you work with to speak about these things more openly?

720
01:02:01.196 --> 01:02:02.036
And why is it important?

721
01:02:02.357 --> 01:02:06.961
So why it's important is when you talk about things, it actually helps you overcome them.

722
01:02:07.221 --> 01:02:12.505
You know, there's a – the things you're afraid to talk about –

723
01:02:13.346 --> 01:02:16.209
You almost it's like giving that giving it more power over yourself.

724
01:02:16.549 --> 01:02:32.466
It's magnifies it in your own mind and being able to put words to it and share it even with one other person reduces the power that it holds over you makes it feel because the other person's reaction.

725
01:02:32.686 --> 01:02:35.129
You'd be like, oh, yeah, maybe it's not as big a deal as I thought.

726
01:02:35.329 --> 01:02:36.130
Maybe I can get over it.

727
01:02:36.910 --> 01:02:45.276
Um, so, uh, now I should say when you're starting out some of these things, you shouldn't be talking about publicly.

728
01:02:45.356 --> 01:02:51.640
So my, with my podcast, it's usually someone sharing a story from years ago now that it's kind of behind them.

729
01:02:52.160 --> 01:03:04.765
So I think by nature, if you're running a business, you can't publicly be sharing some difficult situation you're dealing with right now, especially if other people are involved.

730
01:03:04.785 --> 01:03:06.606
You have to keep it private.

731
01:03:06.926 --> 01:03:10.607
But I would say it's always important to have somebody you trust close to you.

732
01:03:10.627 --> 01:03:13.868
It could be just your co-founders or it could be a mentor.

733
01:03:13.888 --> 01:03:16.870
It could be the role I play in a lot of the investments we make.

734
01:03:17.990 --> 01:03:20.351
But to talk about it so that it's not...

735
01:03:20.912 --> 01:03:23.420
magnified into your head as something that you can't overcome.

736
01:03:24.202 --> 01:03:25.868
When you work with young entrepreneurs now,

737
01:03:27.694 --> 01:03:29.395
what are the skills they should focus on?

738
01:03:29.595 --> 01:03:31.476
What are the things that they have to pay attention to?

739
01:03:31.537 --> 01:03:39.121
Because now you deal with, you invest in technical companies and software and AI and a variety of different categories.

740
01:03:39.161 --> 01:03:45.766
But in the past, say, three, four years, are there different skills that you want the founder to improve?

741
01:03:45.806 --> 01:03:54.331
Like the soft skills, the hard skills, like what is, I know you have a couple different tests that you used to give founders, you give them coding tests and whatnot.

742
01:03:54.651 --> 01:03:57.233
But when you speak to a founder tomorrow,

743
01:03:58.494 --> 01:03:59.274
what are you looking for?

744
01:03:59.494 --> 01:04:01.295
And also, what are you asking them to improve on?

745
01:04:01.916 --> 01:04:06.719
Yeah, so I would say it's an ongoing question, the importance of coding.

746
01:04:07.279 --> 01:04:24.950
And I'm very invested in coding, not only from what you just said and my VC experience, but also I was a co-founder of Code.org, which has brought coding education to hundreds of millions of children.

747
01:04:25.630 --> 01:04:32.876
Um, so it is interesting for me to keep, now we live in a time to ask yourself, is coding still relevant?

748
01:04:33.677 --> 01:04:44.005
Um, I think what is relevant is problem solving ability and, you know, just, um, being able to figure out solutions where other people may not see one.

749
01:04:44.606 --> 01:04:49.470
And I think coding and CS education is one of the best ways to develop that.

750
01:04:49.490 --> 01:04:49.550
Um.

751
01:04:50.890 --> 01:05:06.934
It's not the only way, obviously, but I very much believe in continuing to teach computer science, especially to young children, so that they can develop problem-solving ability and confidence in their problem-solving ability.

752
01:05:07.634 --> 01:05:18.757
Coding is very unique in taking what might seem like an intractable, huge problem and breaking it down into parts and just solve this level and then solving it in different subparts.

753
01:05:20.457 --> 01:05:22.558
So, yeah, so that's my shtick on coding.

754
01:05:22.958 --> 01:05:32.663
But in terms of other skills, you know, Scott, with the advent of AI and agents, I think what I found that's really interesting is that everybody is like a manager.

755
01:05:33.103 --> 01:05:42.708
You know, it used to be like management was for the managerial class, you know, whereas now there's really no such thing as an individual contributor.

756
01:05:42.948 --> 01:05:44.449
Or if you are, like...

757
01:05:44.949 --> 01:05:53.036
to stay productive, you need to figure out how, and what I mean by managing is managing your AI agents as if you have 20 workers working for you.

758
01:05:53.776 --> 01:06:03.504
And so it's, um, it raises some interesting questions about, you know, like if you're a teenager, like you have to develop, you know, like you get to practice managing, um,

759
01:06:04.485 --> 01:06:08.987
way earlier than I, than I did growing up.

760
01:06:09.067 --> 01:06:12.989
Like my first time managing somebody was at a much later age.

761
01:06:13.389 --> 01:06:21.693
And so, um, so yeah, so it's pretty interesting if you're young, hopefully you're already getting that experience, but I'd say in general, um,

762
01:06:23.395 --> 01:06:37.491
anyone, even a one-person startup or a five-person startup, every person needs to learn how to delegate work to agents, how to, and that means how to subdivide the work into tasks, how to specify what you want.

763
01:06:37.571 --> 01:06:39.033
All these are management skills.

764
01:06:40.234 --> 01:06:41.556
And it's just an interesting new way to

765
01:06:43.237 --> 01:06:43.297
AI.

766
01:06:43.718 --> 01:06:57.147
But that's how, I mean, to your point, even an individual contributor within a business, if they're going to compete with their peers and stay and, and, and, you know, surpass their KPIs that are set out for them, their peers are working with agents to get tasks done.

767
01:06:57.167 --> 01:07:00.769
It doesn't matter technical or non-technical role, you're still working with agents.

768
01:07:01.710 --> 01:07:03.351
So you have to, I love that.

769
01:07:03.871 --> 01:07:05.252
You're not, everyone's a manager now.

770
01:07:05.653 --> 01:07:07.954
I mean, and thinking like a manager is, um,

771
01:07:10.215 --> 01:07:18.357
it's just a little bit different, you know, because the ordinary way of thinking is, oh, I encountered a problem, how will I solve it?

772
01:07:18.818 --> 01:07:23.179
Whereas the new way is, who can help me solve it?

773
01:07:23.719 --> 01:07:25.159
You know, who do I call?

774
01:07:25.379 --> 01:07:28.580
Or can one of my agents solve that?

775
01:07:30.000 --> 01:07:35.722
And it actually takes this kind of like, you have to lose the reflex of, let me just dive into it by myself.

776
01:07:36.442 --> 01:07:38.083
Which is not easy for everyone.

777
01:07:38.123 --> 01:07:46.509
You know, like if you're used to solving problems yourself, you can actually slow yourself down versus I know someone smarter than me who can solve this.

778
01:07:46.849 --> 01:07:48.050
So forces delegation.

779
01:07:48.090 --> 01:07:50.772
That might be an AI.

780
01:07:51.132 --> 01:07:53.894
So if, okay, so the skills now, actually, it's interesting.

781
01:07:54.435 --> 01:07:56.216
The skills of management and delegation...

782
01:07:58.360 --> 01:08:02.530
you're actually going to have founders if they learn, they have to learn these skills earlier on.

783
01:08:02.871 --> 01:08:03.332
Cause that's the one.

784
01:08:03.913 --> 01:08:07.582
So you're going to have founders that are better at managing at

785
01:08:09.017 --> 01:08:14.258
1 million, 10 million, 50 million, 100 million IPO because they've learned all these skill sets.

786
01:08:14.438 --> 01:08:15.278
Potentially, yeah.

787
01:08:15.698 --> 01:08:27.140
Because I know companies where a founder who doesn't delegate and still does a lot of the stuff himself, they can be 10, $15 million companies and still have like a key man problem.

788
01:08:27.160 --> 01:08:28.181
But it's harder to scale, yeah.

789
01:08:28.241 --> 01:08:28.981
Yeah, exactly.

790
01:08:29.581 --> 01:08:34.422
What is going to be interesting is whether, and especially with a new generation, whether they...

791
01:08:35.302 --> 01:08:39.125
Like managing an AI, you don't need to worry about the AI's feelings at all.

792
01:08:39.685 --> 01:09:00.241
And so you can end up with people who are not, have a lot of practice with the delegation part and not enough practice with the soft skills of I, whatever, I pissed off the other person or I disrespected them or I didn't pick up on something they said back, you know, that I should have listened to.

793
01:09:00.361 --> 01:09:02.963
So it'll be interesting whether there's a whole new class of,

794
01:09:03.663 --> 01:09:04.744
of issues.

795
01:09:04.804 --> 01:09:05.325
Most likely.

796
01:09:05.645 --> 01:09:07.386
Yes, most likely.

797
01:09:07.787 --> 01:09:09.068
How do you fire somebody?

798
01:09:09.628 --> 01:09:12.351
Firing an AI is just like switch it off.

799
01:09:13.151 --> 01:09:15.713
Whereas firing a person is really difficult.

800
01:09:15.854 --> 01:09:19.577
Of course, and there's empathy and whatnot involved.

801
01:09:19.757 --> 01:09:20.478
Now I think that

802
01:09:22.059 --> 01:09:32.069
Listen, AI is obviously an incredible piece of incredible technology, but there's going to be a premium on individuals who are great at working with other humans.

803
01:09:32.450 --> 01:09:32.950
Absolutely.

804
01:09:33.231 --> 01:09:36.654
And I think that that is a very important, a very, very important skill set.

805
01:09:37.315 --> 01:09:39.177
The human to human piece is amazing.

806
01:09:40.608 --> 01:09:42.628
I think it's gone downhill since COVID to be quite honest.

807
01:09:42.668 --> 01:09:44.389
And I think that- I've noticed the same thing.

808
01:09:44.549 --> 01:09:58.791
Yeah, I think sitting in rooms with real people, that's gonna be exactly, honestly, this is half the reason why I travel to do shows and to do podcasts because you'll never have the quality of conversation with somebody on a Zoom call.

809
01:09:59.251 --> 01:09:59.791
Yep, I agree.

810
01:09:59.991 --> 01:10:01.732
I don't know why, you just can't.

811
01:10:02.352 --> 01:10:09.813
So at this stage, when you choose to make a bet on someone,

812
01:10:10.893 --> 01:10:12.815
We've spoken about a couple of different things that you look for.

813
01:10:14.936 --> 01:10:28.626
Obviously the technical, the charisma, the magnetism, not charisma, the mischief, as well as some of the skills that you think that they should improve on, some soft skills, obviously delegation, management with AI.

814
01:10:30.207 --> 01:10:32.409
That's a whole bunch of different things.

815
01:10:32.609 --> 01:10:38.012
Ultimately, if you had to simplify, and that's an unfair question, but I'll ask it anyways.

816
01:10:38.032 --> 01:10:50.340
If you had to simplify how you make a decision on somebody after you've gone through this checklist of everything, what's the first thought that comes to mind when you speak to a founder and they've displayed all these different things?

817
01:10:50.480 --> 01:10:51.781
What's the decision?

818
01:10:52.241 --> 01:10:53.902
Yes, I want to bet on this founder.

819
01:10:54.462 --> 01:10:55.103
How do you come to that?

820
01:10:55.123 --> 01:10:55.703
Yeah.

821
01:10:55.803 --> 01:10:56.744
Yeah.

822
01:10:57.984 --> 01:11:04.328
So I guess I'd say if I'm talking about an investment decision, it's partly the people, partly the idea.

823
01:11:04.789 --> 01:11:07.150
I put way more emphasis on the people.

824
01:11:08.231 --> 01:11:16.436
There are some people where if they're like so strong that I will actually ignore the idea and just be like, I don't care what they're doing.

825
01:11:17.676 --> 01:11:19.697
And whatever this person builds.

826
01:11:19.917 --> 01:11:20.137
Yeah.

827
01:11:20.477 --> 01:11:22.718
Michael Trull was like that.

828
01:11:23.399 --> 01:11:24.259
And Amon Sanger.

829
01:11:24.339 --> 01:11:26.280
I mean, both of them were amazing co-founders.

830
01:11:27.460 --> 01:11:37.884
But I'd say on the person side, if I had to boil it down to one question, it's just literally, would I work for this person?

831
01:11:38.324 --> 01:11:42.986
Do I see this person being able to attract their smartest friends to work for them?

832
01:11:43.686 --> 01:11:44.627
And really the challenge is...

833
01:11:45.447 --> 01:11:47.407
to hire people smarter than yourself.

834
01:11:47.748 --> 01:11:52.769
Can this person hire and lead people even smarter than themself?

835
01:11:53.189 --> 01:11:54.869
So that's on the person side.

836
01:11:55.249 --> 01:12:02.091
And on the idea side, the main question I ask is, I'm not asking will this succeed?

837
01:12:02.271 --> 01:12:05.292
I'm asking if this succeeds, how big will it be?

838
01:12:06.132 --> 01:12:09.893
And it goes back to how ambitious is this idea?

839
01:12:11.373 --> 01:12:16.696
Some people might think of this in kind of like a business school type of way, like what's the TAM, how many dollars?

840
01:12:16.816 --> 01:12:21.558
But some ideas you can't even quantify that because it's never been done before.

841
01:12:21.618 --> 01:12:23.599
There is no addressable market exists yet.

842
01:12:23.679 --> 01:12:25.640
No one's solved this need before.

843
01:12:26.581 --> 01:12:36.006
But, you know, Airbnb before it existed, the vision was like someday everybody will be able to monetize their vacant room.

844
01:12:36.626 --> 01:12:44.470
with travelers and someday instead of staying at a hotel, you'll meet new people when you travel by staying in their, in their homes.

845
01:12:44.930 --> 01:12:48.312
And, um, it was kind of hard to put a TAM on it.

846
01:12:49.232 --> 01:12:53.414
Um, I mean, you could say the hotel industry TAM, but it wasn't exactly that.

847
01:12:54.235 --> 01:13:02.219
Um, but it was just inspiring how, you know, how, uh, how different it was or call she, it was the idea that you could, um,

848
01:13:03.139 --> 01:13:04.600
bet on the outcome of anything.

849
01:13:04.620 --> 01:13:14.345
You could trade on all sorts of things that today, you know, you might say, I bet this will happen, but you can't actually do that, you know.

850
01:13:14.825 --> 01:13:16.926
And what's the time of that?

851
01:13:17.346 --> 01:13:18.047
It was hard to know.

852
01:13:18.607 --> 01:13:27.431
But yeah, I guess I try to, whether it can be measured or just feel intrinsically, if this succeeds, how big will it be?

853
01:13:28.472 --> 01:13:29.852
That's how I evaluate ideas.

854
01:13:30.233 --> 01:13:30.473
And I

855
01:13:31.313 --> 01:13:35.598
on purpose, try to avoid thinking, what's the probability of success?

856
01:13:35.618 --> 01:13:36.959
Like, what are the risk factors?

857
01:13:37.159 --> 01:13:41.283
I think actually risk factors, the more risk factors, the better.

858
01:13:41.504 --> 01:13:49.492
If it's going to be a big outcome, you know, willing to have lots of risk, if it's something that could be, you know, earth shattering in its size.

859
01:13:50.172 --> 01:13:54.397
You've learned so much first through being an entrepreneur and now being an investor.

860
01:13:54.417 --> 01:13:54.537
Yeah.

861
01:13:55.437 --> 01:14:05.360
what's the biggest shift that you've made in how you make decisions and how you calculate risk compared to when you were first starting your companies to now when you decide to invest?

862
01:14:05.400 --> 01:14:11.102
If you're going to look back 30 years ago, what would be the lesson that you would tell yourself?

863
01:14:12.202 --> 01:14:13.823
who's Ali's just starting out?

864
01:14:14.264 --> 01:14:18.307
I think it would be to be even less afraid to take more risk.

865
01:14:18.647 --> 01:14:22.470
You know, I think that, I mean, I've taken quite a bit of risk.

866
01:14:22.570 --> 01:14:30.536
I've had a share of big failures and success, but I think even more risk I would have done even better.

867
01:14:31.056 --> 01:14:32.798
More failures, but even bigger successes.

868
01:14:32.878 --> 01:14:38.282
So your podcast, Confession with Ali Portovi, that's available October 13th anywhere you get your podcasts?

869
01:14:38.302 --> 01:14:38.382
Yes.

870
01:14:40.003 --> 01:14:41.063
where else can they connect with you?

871
01:14:41.163 --> 01:14:43.484
So all the socials, website, anything you want to drop.

872
01:14:43.504 --> 01:14:44.425
We'll put it in the show notes too.

873
01:14:44.625 --> 01:14:51.629
I guess follow me on x. x.com slash aportovi for Ali Partovi.

874
01:14:51.889 --> 01:14:52.269
Perfect.

875
01:14:52.889 --> 01:14:57.552
Actually, my pinned tweet is the Steve Jobs story that I mentioned.

876
01:14:58.772 --> 01:15:02.074
So from time to time, I'll reset something else that I'm highlighting.

877
01:15:02.134 --> 01:15:08.157
But that's kind of been my default tweet that I keep at the top.

878
01:15:08.818 --> 01:15:13.805
The last thing I like to ask, obviously you've had an incredible career.

879
01:15:14.506 --> 01:15:16.009
If you could, if you could,

880
01:15:18.274 --> 01:15:24.536
go back and tell your 20-year-old self, it could be business advice, it could be just life advice.

881
01:15:26.276 --> 01:15:30.258
You told me one thing you'd tell your younger self would be to take more risk, but give me one more.

882
01:15:30.398 --> 01:15:36.920
Leave the audience with one last piece of wisdom that you would tell your younger self that would have really helped you.

883
01:15:37.680 --> 01:15:44.822
I mean, it's related to the same thing, but I guess it's to realize that other people are not,

884
01:15:46.483 --> 01:15:55.167
like judging me for if I have a failure that, you know, that I'm not, if I did something and it was a complete bomb, I'm not letting anyone else down.

885
01:15:55.928 --> 01:16:01.791
I, when I was younger, I had in my mind that I need to take care of my own parents, for example.

886
01:16:02.611 --> 01:16:04.013
they had no such idea.

887
01:16:04.033 --> 01:16:06.517
You know, that was not what they were expecting.

888
01:16:06.938 --> 01:16:08.540
I had put that on myself.

889
01:16:09.041 --> 01:16:14.649
And just more generally this feeling that, like, if I screw up, how much other people will judge me?

890
01:16:15.029 --> 01:16:16.351
And I just don't think that's a thing.

891
01:16:16.512 --> 01:16:17.052
I think that's...

892
01:16:17.573 --> 01:16:23.578
I think we each put that on our own shoulders, but it turns out other people have their own demons.

893
01:16:23.618 --> 01:16:34.168
They have their own insecurities to worry about, and they don't have enough time to like spend, you know, like dwelling on your mess ups.

894
01:16:34.488 --> 01:16:40.793
So it just, you know, I think hopefully hearing this for anyone listening would lighten the load a little bit.

895
01:16:41.034 --> 01:16:42.255
You know, if you're

896
01:16:43.458 --> 01:16:48.136
doing something that's not successful or give you more courage to take, um, take bigger swings.