00:00

If you can get into a top twenty university and you have to get going to a ton of debt, it is one hundred percent worth it. In that, if that's the case, It ain't broken. I think it's doing great.

If you can get into a top twenty university and you have to get going to a ton of debt, it is one hundred percent worth it. In that, if that's the case, It ain't broken. I think it's doing great.

00:12

I feel like I could rule the world and know I could be what I want to.

I feel like I could rule the world and know I could be what I want to.

00:17

I put my all in it like today. He's all on a road. Let's travel never looking back.

I put my all in it like today. He's all on a road. Let's travel never looking back.

00:22

Okay.

Okay.

00:24

My first we by the way, you know, when you're listening to this, it's all gonna sound smooth, but we've just recorded this, like, three times because remote work still sucks a little bit.

My first we by the way, you know, when you're listening to this, it's all gonna sound smooth, but we've just recorded this, like, three times because remote work still sucks a little bit.

00:34

But we have Brie here. Brie Brie Kimmell is, an investor in mostly, I think.

But we have Brie here. Brie Brie Kimmell is, an investor in mostly, I think.

00:40

Work work related products. So maybe you could tell us why it's so hard. Alright. Let me just read three things off your little bio thing here that I think are interesting. So,

Work work related products. So maybe you could tell us why it's so hard. Alright. Let me just read three things off your little bio thing here that I think are interesting. So,

00:50

solo capitalist. So you raised your own fund by yourself after never having worked in VC before that. Is that correct?

solo capitalist. So you raised your own fund by yourself after never having worked in VC before that. Is that correct?

00:56

That's correct.

That's correct.

00:57

Okay. Great. Another one. According to this, you have invested in seven unicorns already, which is kinda nutty. What are the seven?

Okay. Great. Another one. According to this, you have invested in seven unicorns already, which is kinda nutty. What are the seven?

01:05

Yeah. So I started work life about a year and a half ago invested

Yeah. So I started work life about a year and a half ago invested

01:09

in Hopin

in Hopin

01:10

Webflow, which was an angel investment from when I was at Zendesk.

Webflow, which was an angel investment from when I was at Zendesk.

01:14

Pipe, public,

Pipe, public,

01:17

a bunch of interesting companies and sort of future workspace.

a bunch of interesting companies and sort of future workspace.

01:20

K. Well, that's pretty impressive.

K. Well, that's pretty impressive.

01:23

Okay. And then another one that's on here that I think is kinda interesting

Okay. And then another one that's on here that I think is kinda interesting

01:27

that I think we should just jump in on. I don't know, Sam, where do you wanna

that I think we should just jump in on. I don't know, Sam, where do you wanna

01:30

start? You wanna start with this? I I wanna start with this. Well,

start? You wanna start with this? I I wanna start with this. Well,

01:33

That's mine. I wanna start with that. That's yours, bro.

That's mine. I wanna start with that. That's yours, bro.

01:37

That's mine. Bree, do you know what this podcast is about

That's mine. Bree, do you know what this podcast is about

01:40

I do know what this podcast is about. I've actually listened to many episodes. I'm a big fan. Great. So we don't need to explain much to you. So Brie. You and what you and go ahead and plug your new podcast. You have, coming out. What what's it called? Oh, we're coming in hot. We're plugging the podcast already. I thought that was gonna come in later. No. No. We do. No. Go ahead. And then people are like, I'm not I'm not gonna click it. And then at the end, they'll do it.

I do know what this podcast is about. I've actually listened to many episodes. I'm a big fan. Great. So we don't need to explain much to you. So Brie. You and what you and go ahead and plug your new podcast. You have, coming out. What what's it called? Oh, we're coming in hot. We're plugging the podcast already. I thought that was gonna come in later. No. No. We do. No. Go ahead. And then people are like, I'm not I'm not gonna click it. And then at the end, they'll do it.

02:02

Yeah. So we're,

Yeah. So we're,

02:04

the first podcast

the first podcast

02:06

after,

after,

02:07

this one to be part of the HubSpot podcast network.

this one to be part of the HubSpot podcast network.

02:10

So myself and my best friend, Alexis Kaye, she's a stand up comedian.

So myself and my best friend, Alexis Kaye, she's a stand up comedian.

02:14

She makes a lot of tech parody videos. We decided to start a business podcast

She makes a lot of tech parody videos. We decided to start a business podcast

02:18

with the fine folks over at HubSpot who have been awesome. They've given us a team, We've interviewed interesting people. It's it's been cool for me because, you know, as you mentioned, I mostly do software investing, and we're actually interviewing a lot of direct to consumer founders and people that I've never met before. And so we have this new podcast coming out called the shakeup where we interview business leaders about very specific decisions that they've made that have changed the trajectory of their company.

with the fine folks over at HubSpot who have been awesome. They've given us a team, We've interviewed interesting people. It's it's been cool for me because, you know, as you mentioned, I mostly do software investing, and we're actually interviewing a lot of direct to consumer founders and people that I've never met before. And so we have this new podcast coming out called the shakeup where we interview business leaders about very specific decisions that they've made that have changed the trajectory of their company.

02:43

So

So

02:44

the awfulist hang on. Hang on. Is that,

the awfulist hang on. Hang on. Is that,

02:47

like,

like,

02:48

is the vibe, like, comedy? Cause she's a comedian? Like, is this call her daddy, or is this like,

is the vibe, like, comedy? Cause she's a comedian? Like, is this call her daddy, or is this like,

02:54

you know, how I built this, or what is this?

you know, how I built this, or what is this?

02:57

It actually that's a really great. That's a really great point. We're somewhere between the two.

It actually that's a really great. That's a really great point. We're somewhere between the two.

03:02

We wanted to make it interesting and educational, and it is more of a business audience. I think in this new era of working from home, unless interesting and entertaining. People don't wanna listen. And so it's not corporate. It's not boring.

We wanted to make it interesting and educational, and it is more of a business audience. I think in this new era of working from home, unless interesting and entertaining. People don't wanna listen. And so it's not corporate. It's not boring.

03:16

One of the most challenging parts of the podcast for me is that it's very hard to get business people off script. They've all gone gone through comms training. They all have, you know, their executive coach, To get them to really open up and share vulnerable moments or to be really open and authentic has been surprisingly really hard.

One of the most challenging parts of the podcast for me is that it's very hard to get business people off script. They've all gone gone through comms training. They all have, you know, their executive coach, To get them to really open up and share vulnerable moments or to be really open and authentic has been surprisingly really hard.

03:36

Sam is really good at it. He, I don't know how he does it, but he he breaks through that every single time.

Sam is really good at it. He, I don't know how he does it, but he he breaks through that every single time.

03:43

But I gotta ask Wait, Sean, you I mean, I I think you're good at You're you're pretty good at that too. I think we both are. You're good at getting them. You're you're good at, like, getting people off the script.

But I gotta ask Wait, Sean, you I mean, I I think you're good at You're you're pretty good at that too. I think we both are. You're good at getting them. You're you're good at, like, getting people off the script.

03:53

Really good at getting people off script,

Really good at getting people off script,

03:55

because Sam will do something like he'll, like, he'll see you and he'll be like, he'll be like, like, yeah, he's like, you're good looking. I mean, like, not traditionally Like, you're you're good looking. So what and then they're like, what are you talking about? And it's like kind of a compliment, a kind of an insult. And then they're just trying to figure out, like, where do I take this? And so then, like, something natural comes out, or he'll be like, you know, ask them about, I don't know, some something weird that sit that's behind them in the room or something like that. And, that usually gets people off So I'm so, so bad at this that I had to bring a stand up comedian to really, like, warm up the guests. I I, like, as an investor, it's a little bit robotic and you tend to ask the same five to ten questions.

because Sam will do something like he'll, like, he'll see you and he'll be like, he'll be like, like, yeah, he's like, you're good looking. I mean, like, not traditionally Like, you're you're good looking. So what and then they're like, what are you talking about? And it's like kind of a compliment, a kind of an insult. And then they're just trying to figure out, like, where do I take this? And so then, like, something natural comes out, or he'll be like, you know, ask them about, I don't know, some something weird that sit that's behind them in the room or something like that. And, that usually gets people off So I'm so, so bad at this that I had to bring a stand up comedian to really, like, warm up the guests. I I, like, as an investor, it's a little bit robotic and you tend to ask the same five to ten questions.

04:31

Right. And so that's Alexis's job. She's world class at getting people you know, maybe flattering them a little bit, maybe flattering herself, maybe complimenting the show, but then finding ways to get people to open up and to to be a little bit less scripted.

Right. And so that's Alexis's job. She's world class at getting people you know, maybe flattering them a little bit, maybe flattering herself, maybe complimenting the show, but then finding ways to get people to open up and to to be a little bit less scripted.

04:44

Is it hard to be on a podcast with somebody who's a professional comedian? Like, I know Sam struggles just dealing with my level of humor in my my month, Alice.

Is it hard to be on a podcast with somebody who's a professional comedian? Like, I know Sam struggles just dealing with my level of humor in my my month, Alice.

04:53

Are you intimidated by your your comedian,

Are you intimidated by your your comedian,

04:56

co host? You know, it has been fun.

co host? You know, it has been fun.

04:58

You know, now that we have a producer as well, you know, the producer is very clear at helping us define our roles. And so, like, I know that I'm not funny. It's not my role to be funny on the show. It's my role to, like, bring in data and research and I get to be the nerdy one, which is great.

You know, now that we have a producer as well, you know, the producer is very clear at helping us define our roles. And so, like, I know that I'm not funny. It's not my role to be funny on the show. It's my role to, like, bring in data and research and I get to be the nerdy one, which is great.

05:14

I don't attempt to be funny at all.

I don't attempt to be funny at all.

05:16

Yeah. That's my strategy. By the way, Sean, they have, like, producers and shit and, like, have, like,

Yeah. That's my strategy. By the way, Sean, they have, like, producers and shit and, like, have, like,

05:26

I call the Alarna, the lady who runs the podcast network at at a hubspot. I'm like, wait. Brie and these folks are getting, like, producers and head shots. Like, I've been using, like, Eric on fiverr, like, to, like,

I call the Alarna, the lady who runs the podcast network at at a hubspot. I'm like, wait. Brie and these folks are getting, like, producers and head shots. Like, I've been using, like, Eric on fiverr, like, to, like,

05:38

rig the stuff together. Honestly, it's I don't even show up to the meeting. So they're probably, like, yeah. Course, you don't get anything. You don't show up to the fucking meeting. Why would we give you any resources?

rig the stuff together. Honestly, it's I don't even show up to the meeting. So they're probably, like, yeah. Course, you don't get anything. You don't show up to the fucking meeting. Why would we give you any resources?

05:47

So, Bree, you've listened to you've listened to a couple podcasts

So, Bree, you've listened to you've listened to a couple podcasts

05:50

I wanna just so what we're gonna do is we're gonna brainstorm a little bit. I know that you who've you've got a couple ideas here that I definitely wanna talk about. I wanna talk about your calendar because, like, when I see that, I just wanna kill myself. I can't believe that that's your calendar. I mean, I'm I'm embarrassed that you saw it, actually. I'm a little bit embarrassed. Oh my god. So I wanna talk about a bunch of stuff. But before we,

I wanna just so what we're gonna do is we're gonna brainstorm a little bit. I know that you who've you've got a couple ideas here that I definitely wanna talk about. I wanna talk about your calendar because, like, when I see that, I just wanna kill myself. I can't believe that that's your calendar. I mean, I'm I'm embarrassed that you saw it, actually. I'm a little bit embarrassed. Oh my god. So I wanna talk about a bunch of stuff. But before we,

06:12

we get into that, can can I tell you guys something that's I've been obsessed with over the past week So there's this new Anthony Bourdain documentary.

we get into that, can can I tell you guys something that's I've been obsessed with over the past week So there's this new Anthony Bourdain documentary.

06:19

I actually don't remember what it's called. Do you know what you guys know what I'm talking about?

I actually don't remember what it's called. Do you know what you guys know what I'm talking about?

06:23

A roadrunner. It's called road roadrunner. Okay. So it came out last week, and it's basically about his last, maybe,

A roadrunner. It's called road roadrunner. Okay. So it came out last week, and it's basically about his last, maybe,

06:31

three or four weeks of life or something like that. And it talks about it seems like details his last four weeks of life and it talks about the the his whole journey and whatever. That's not the point. The point is is at the end, they have this amazing Soundbite. So basically right before he died, he wrote an email to someone it wasn't like a suicide note, but it was like, like, I'm sad, type of thing. And you hear him read that email.

three or four weeks of life or something like that. And it talks about it seems like details his last four weeks of life and it talks about the the his whole journey and whatever. That's not the point. The point is is at the end, they have this amazing Soundbite. So basically right before he died, he wrote an email to someone it wasn't like a suicide note, but it was like, like, I'm sad, type of thing. And you hear him read that email.

06:54

Well, it's not actually him. It's AI. He never actually,

Well, it's not actually him. It's AI. He never actually,

06:58

said that. But he die you know, he wrote the email and then he died. And this company used this technology

said that. But he die you know, he wrote the email and then he died. And this company used this technology

07:03

to to read out the email, and it sounds just like him. If if I wasn't, like, a nerd and researched it, I would have thought that it was him. And I started I started thinking about this I started thinking about a few things. And,

to to read out the email, and it sounds just like him. If if I wasn't, like, a nerd and researched it, I would have thought that it was him. And I started I started thinking about this I started thinking about a few things. And,

07:15

the reason I kinda am parent putting all this is together is I read this story about this guy last named Josh. And, basically, what happened was his girlfriend died, and he used GPT three or g yeah, GPT three, and he loaded up a ton of social media messages, like you know, Facebook messages and tweets and Twitter stuff, or and and and text stuff that she had said, and he put it to GB three and he made a girlfriend who knew she died, and he could talk to her, and and and and and, like, feel like he's still connected.

the reason I kinda am parent putting all this is together is I read this story about this guy last named Josh. And, basically, what happened was his girlfriend died, and he used GPT three or g yeah, GPT three, and he loaded up a ton of social media messages, like you know, Facebook messages and tweets and Twitter stuff, or and and and text stuff that she had said, and he put it to GB three and he made a girlfriend who knew she died, and he could talk to her, and and and and and, like, feel like he's still connected.

07:45

A, do you think this is wrong and creepy? B, that Anthony Bourade thing? That's obviously that's gonna happen. That's that's gonna happen in the future. How movies are gonna are are gonna come about. But three,

A, do you think this is wrong and creepy? B, that Anthony Bourade thing? That's obviously that's gonna happen. That's that's gonna happen in the future. How movies are gonna are are gonna come about. But three,

07:55

When are we gonna start talking to our dead moms?

When are we gonna start talking to our dead moms?

07:58

Fuck.

Fuck.

08:00

Came hot at the end there. Is this crazy? Like, Like, it like, the fact that Anthony Bour Day did this, do isn't it wild that we're gonna be having these conversations? I don't hang around with the smart enough people to be to be who build themselves a free have. Did you ever see that episode of Black Mirror where they did this, basically?

Came hot at the end there. Is this crazy? Like, Like, it like, the fact that Anthony Bour Day did this, do isn't it wild that we're gonna be having these conversations? I don't hang around with the smart enough people to be to be who build themselves a free have. Did you ever see that episode of Black Mirror where they did this, basically?

08:17

So do you watch any Black Mirror, Sam?

So do you watch any Black Mirror, Sam?

08:19

No. It's alright. It's a little bit depressing, but it's, like, too accurate also at the same time. So the in in Black Mirror, they take this to the extreme,

No. It's alright. It's a little bit depressing, but it's, like, too accurate also at the same time. So the in in Black Mirror, they take this to the extreme,

08:27

and basically this girl's living with her boyfriend, and then by the, you know, middle or end of the episode, you realize that this boyfriend is not, like, real. It's basically, like, an AI robot that is just, like, kind of, like, He's not perfect. Like, so it gives her companionship because, like, it's, like, he's still here. He's doing all the things. It sounds like him and it looks like him, but he's not actually human. So it's kind of like, you know, the uncanny valley. It doesn't seem it's not actually the real thing. And so it's kind of depressing for her, to be with this kinda, like, shadow of her boyfriend or whatever. And so there's been a bunch of people trying to do this with GPD three. And, somebody did it with our podcast. I don't know if you saw that. Somebody uploaded my

and basically this girl's living with her boyfriend, and then by the, you know, middle or end of the episode, you realize that this boyfriend is not, like, real. It's basically, like, an AI robot that is just, like, kind of, like, He's not perfect. Like, so it gives her companionship because, like, it's, like, he's still here. He's doing all the things. It sounds like him and it looks like him, but he's not actually human. So it's kind of like, you know, the uncanny valley. It doesn't seem it's not actually the real thing. And so it's kind of depressing for her, to be with this kinda, like, shadow of her boyfriend or whatever. And so there's been a bunch of people trying to do this with GPD three. And, somebody did it with our podcast. I don't know if you saw that. Somebody uploaded my

09:04

a bunch of stories I told or something like that. He put it in. Oh, I saw that. Yeah. And he's like, look, you can ask on a question and then, like, it gives a pretty real like, it's like me when I just bullshit some answer. It's like it bullshits it just as good as I can. I'm like, wow, this is kind of amazing. So I think we're getting

a bunch of stories I told or something like that. He put it in. Oh, I saw that. Yeah. And he's like, look, you can ask on a question and then, like, it gives a pretty real like, it's like me when I just bullshit some answer. It's like it bullshits it just as good as I can. I'm like, wow, this is kind of amazing. So I think we're getting

09:20

we're getting we're getting closer to where that's that's like,

we're getting we're getting closer to where that's that's like,

09:24

it's like the Anthony Bourdain thing where, of course, it's not gonna be fully accurate, but Damn. It's like it feels like magic. It was that this wasn't really a thing five, ten years ago. Bree, what have you seen in that space?

it's like the Anthony Bourdain thing where, of course, it's not gonna be fully accurate, but Damn. It's like it feels like magic. It was that this wasn't really a thing five, ten years ago. Bree, what have you seen in that space?

09:35

Yeah. I mean, one point in that with the ordained piece. I mean, what's interesting there is, you know, he

Yeah. I mean, one point in that with the ordained piece. I mean, what's interesting there is, you know, he

09:43

the question is, are you building a legacy and are you carrying someone's story forward? I think that's really cool. I think if there are sound bites or old songs or if you can take a book that was written a decade ago and then put it in the voice of someone who's already passed away, that can be really cool. I mean, that's really like a strong storytelling angle in a way to really continue their legacy.

the question is, are you building a legacy and are you carrying someone's story forward? I think that's really cool. I think if there are sound bites or old songs or if you can take a book that was written a decade ago and then put it in the voice of someone who's already passed away, that can be really cool. I mean, that's really like a strong storytelling angle in a way to really continue their legacy.

10:04

The

The

10:06

kind of the gray area for me is, you know, for the guy that's created a fake girlfriend that's,

kind of the gray area for me is, you know, for the guy that's created a fake girlfriend that's,

10:12

using previous text conversations, like, I'm a little bit concerned for him in in the long the long term. You know, I think he's maybe

using previous text conversations, like, I'm a little bit concerned for him in in the long the long term. You know, I think he's maybe

10:19

staying in the past as opposed to, like, you know, going through therapy

staying in the past as opposed to, like, you know, going through therapy

10:24

or, you know, spending time with family and friends and then, like, getting back out there again. And so it probably depends on the use case and some of scenarios for these technologies, but I agree. I, love Black Mirror. I've watched them all. Binge watch them all. And, it's really creepy to see that a lot of these things are actually proving to be true. So then I was I was looking around at what other stuff is like this. There's this one called ai writer dot And what you can do is you can look at the variety of different dead authors and dead famous people that they have, and they've uploaded all their personalities. And you could ask Ben Franklin a question. It's pretty amazing. Anyway, I just wanted to tell you all about that. I've I've been obsessing about this. So there's one that, I'm gonna tell you guys about

or, you know, spending time with family and friends and then, like, getting back out there again. And so it probably depends on the use case and some of scenarios for these technologies, but I agree. I, love Black Mirror. I've watched them all. Binge watch them all. And, it's really creepy to see that a lot of these things are actually proving to be true. So then I was I was looking around at what other stuff is like this. There's this one called ai writer dot And what you can do is you can look at the variety of different dead authors and dead famous people that they have, and they've uploaded all their personalities. And you could ask Ben Franklin a question. It's pretty amazing. Anyway, I just wanted to tell you all about that. I've I've been obsessing about this. So there's one that, I'm gonna tell you guys about

11:05

But you,

But you,

11:07

I I almost don't wanna tell you until I lock in my full investment, but, I wanna invest in this company. I saw it. I haven't even had a chance to talk to them yet. But what they're doing is,

I I almost don't wanna tell you until I lock in my full investment, but, I wanna invest in this company. I saw it. I haven't even had a chance to talk to them yet. But what they're doing is,

11:17

they basically made a a a version of deep fake that you can do for yourself so you can thank customers personally

they basically made a a a version of deep fake that you can do for yourself so you can thank customers personally

11:24

for, for a purchase or for anything that they did. So, basically, you record yourself once sitting in a room, like, I'm here. Right? And I say, oh, you know, thanks for leaving that review on iTunes for the podcast cast. Yeah. Or thanks for tweeting out the podcast. And then what what it does is it basically takes me in that scenario and it starts it off with Hey, Sam.

for, for a purchase or for anything that they did. So, basically, you record yourself once sitting in a room, like, I'm here. Right? And I say, oh, you know, thanks for leaving that review on iTunes for the podcast cast. Yeah. Or thanks for tweeting out the podcast. And then what what it does is it basically takes me in that scenario and it starts it off with Hey, Sam.

11:43

You know, saw your review. Just wanna say blah blah blah, but I don't have to record the hey Sam part. The hey Sam part, the personal touch gets basically deep faked in the video, and then it can insert any of the variables. So, like, let's say it's e commerce, I could say, hey, blank name. Right? So it'd be like, hey, Sam, thing, you know, thanks for, thanks for shopping with us. I hope you love the castro mattress that you just bought. Right? And it'll make the whole thing sound pretty seamless. And just input variables

You know, saw your review. Just wanna say blah blah blah, but I don't have to record the hey Sam part. The hey Sam part, the personal touch gets basically deep faked in the video, and then it can insert any of the variables. So, like, let's say it's e commerce, I could say, hey, blank name. Right? So it'd be like, hey, Sam, thing, you know, thanks for, thanks for shopping with us. I hope you love the castro mattress that you just bought. Right? And it'll make the whole thing sound pretty seamless. And just input variables

12:10

from,

from,

12:11

from a database essentially and just turn it into your voice. So I think that's kind of amazing to add a quote, unquote, personal touch that's gonna be, you know, automated. It scales somehow that how do you find that? Scalable.

from a database essentially and just turn it into your voice. So I think that's kind of amazing to add a quote, unquote, personal touch that's gonna be, you know, automated. It scales somehow that how do you find that? Scalable.

12:23

My scout Zach found it and he sent it to me.

My scout Zach found it and he sent it to me.

12:26

I'm really excited for that use case. I'm also really excited to see some of the bloopers. Like, I can't wait to see a person's face say, hey, first name, last name. Right. How's like an email? Day going. Thanks for being a customer. Right. Hey asshole. Thanks for

I'm really excited for that use case. I'm also really excited to see some of the bloopers. Like, I can't wait to see a person's face say, hey, first name, last name. Right. How's like an email? Day going. Thanks for being a customer. Right. Hey asshole. Thanks for

12:41

I find sometimes the automated stuff. I've tried some of these automated gifting services before. And if the database isn't in a perfect form and first name last name isn't spelled right, you end up looking like an asshole, but it can be pretty funny.

I find sometimes the automated stuff. I've tried some of these automated gifting services before. And if the database isn't in a perfect form and first name last name isn't spelled right, you end up looking like an asshole, but it can be pretty funny.

12:53

So, Brie, I have to ask you a question. It this is gonna sound like an insult, which we just told you. I'm apparently going for it. He's about to do the thing. This is not an insult. This is not an insult.

So, Brie, I have to ask you a question. It this is gonna sound like an insult, which we just told you. I'm apparently going for it. He's about to do the thing. This is not an insult. This is not an insult.

13:04

Alright. So I'm looking at work life ventures. So this is this, firm you started in in two thousand nineteen. Before that, you worked at,

Alright. So I'm looking at work life ventures. So this is this, firm you started in in two thousand nineteen. Before that, you worked at,

13:11

I was looking at your LinkedIn. What was it? It starts with a z, the the big software Zendesk.

I was looking at your LinkedIn. What was it? It starts with a z, the the big software Zendesk.

13:17

You had a normal, a good job there. So, like, you are a relatively normal person, but you are investing in, like, the most baller companies at the earliest times.

You had a normal, a good job there. So, like, you are a relatively normal person, but you are investing in, like, the most baller companies at the earliest times.

13:27

How, like,

How, like,

13:28

the the left handed compliment is, like, you're not really, like, a somebody, and yet somehow you already are a somebody. How on earth did you pull this off? As you go from nobody to somebody. I think we can go we can go even even before Zendesk. Before Zendesk, you know, I'd worked at a big tech company. I was at Expedia.

the the left handed compliment is, like, you're not really, like, a somebody, and yet somehow you already are a somebody. How on earth did you pull this off? As you go from nobody to somebody. I think we can go we can go even even before Zendesk. Before Zendesk, you know, I'd worked at a big tech company. I was at Expedia.

13:43

Went to a state school, grew up in Ohio. I mean, we can we can cut the data anyway. I'm a very normal person.

Went to a state school, grew up in Ohio. I mean, we can we can cut the data anyway. I'm a very normal person.

13:50

I live a very normal life. Like, I'm not your, like, venture capitalist that's flying in private jets and, you know, doing all these crazy things. Sure. You might be now. Yeah. You might be now.

I live a very normal life. Like, I'm not your, like, venture capitalist that's flying in private jets and, you know, doing all these crazy things. Sure. You might be now. Yeah. You might be now.

14:02

You said it sounds like you're about to make a killing?

You said it sounds like you're about to make a killing?

14:05

Well, going back to your point, thank you. That wasn't insulting. That's, like, very clearly,

Well, going back to your point, thank you. That wasn't insulting. That's, like, very clearly,

14:10

something you can see from LinkedIn is, you know, I I started out as a marketer,

something you can see from LinkedIn is, you know, I I started out as a marketer,

14:14

started meeting startups on evenings and weekends, started hosting dinners,

started meeting startups on evenings and weekends, started hosting dinners,

14:19

The interesting thing that I don't think a lot of people truly realize until you're on the ground in Silicon Valley is you just end up meeting a lot of people just by proximity.

The interesting thing that I don't think a lot of people truly realize until you're on the ground in Silicon Valley is you just end up meeting a lot of people just by proximity.

14:28

Like, you walk into a dinner, you make one or two connections, you keep checking in with them, you stay in touch,

Like, you walk into a dinner, you make one or two connections, you keep checking in with them, you stay in touch,

14:35

and that's how you build your work. And, you know, everyone there is going somewhere. Like, you don't move to the valley,

and that's how you build your work. And, you know, everyone there is going somewhere. Like, you don't move to the valley,

14:40

pay crazy insane rent prices,

pay crazy insane rent prices,

14:44

to not be, like, in the mix.

to not be, like, in the mix.

14:46

And so I found that, you know, a lot of the things that I did early on as an angel I was really intentional about, like, the angel investment in webflow.

And so I found that, you know, a lot of the things that I did early on as an angel I was really intentional about, like, the angel investment in webflow.

14:56

I had organized,

I had organized,

14:57

a go to market workshop invited webflow. So I had, like, you know, a whole day with the team, which was great. I hosted a couple of no code dinners to spend as much time with them as possible.

a go to market workshop invited webflow. So I had, like, you know, a whole day with the team, which was great. I hosted a couple of no code dinners to spend as much time with them as possible.

15:09

I try to find interesting ways to really build close relationships with a handful of companies. I know we talked about you you mentioned my calendar and how insane it is. I actually don't take that many meetings, and I I rarely do one on one coffees with people, which is really interesting and kind of a different strategy from other VCs, but I try to find interesting touch points that will give me

I try to find interesting ways to really build close relationships with a handful of companies. I know we talked about you you mentioned my calendar and how insane it is. I actually don't take that many meetings, and I I rarely do one on one coffees with people, which is really interesting and kind of a different strategy from other VCs, but I try to find interesting touch points that will give me

15:31

enough of an angle to invest in a company that's starting to work.

enough of an angle to invest in a company that's starting to work.

15:35

So webflow Can I just read your schedule, by the way? Because nobody's looking at this. So let me just take let's just take a Wednesday. Okay. Here's Wednesday just for for people. You You wake up seven AM. Morning block. What what happens in morning block? Are you, in my opinion? Usually, I go to the gym. Usually, I go to the gym.

So webflow Can I just read your schedule, by the way? Because nobody's looking at this. So let me just take let's just take a Wednesday. Okay. Here's Wednesday just for for people. You You wake up seven AM. Morning block. What what happens in morning block? Are you, in my opinion? Usually, I go to the gym. Usually, I go to the gym.

15:51

During COVID, I rode my Peloton, but I'm I'm now back to going to the gym. Right. Okay. Exactly. So we're going up until,

During COVID, I rode my Peloton, but I'm I'm now back to going to the gym. Right. Okay. Exactly. So we're going up until,

15:58

about eight thirty seven to eight thirty, that's, like, get ready to go to the gym. Go to the gym. It says Peloton forty five. Alright. Great. Now we have morning block two. What's happening morning block two? Morning bought too, I send emails to portfolio companies and ask them for ways to help, or sometimes there's project specific tangible projects I have to work on for a specific company. Cool. So thirty minutes there. Then,

about eight thirty seven to eight thirty, that's, like, get ready to go to the gym. Go to the gym. It says Peloton forty five. Alright. Great. Now we have morning block two. What's happening morning block two? Morning bought too, I send emails to portfolio companies and ask them for ways to help, or sometimes there's project specific tangible projects I have to work on for a specific company. Cool. So thirty minutes there. Then,

16:18

okay. Where are we at? So team check ins, we have a one on one with Neil. Great.

okay. Where are we at? So team check ins, we have a one on one with Neil. Great.

16:22

Email processing. I love I love that. You're,

Email processing. I love I love that. You're,

16:26

like, like, an actual machine. I'm a little bit embarrassed right now. This is, like, you're reading my diary. It's, like, No. You put it on the internet. You put it on the internet. I know. I know.

like, like, an actual machine. I'm a little bit embarrassed right now. This is, like, you're reading my diary. It's, like, No. You put it on the internet. You put it on the internet. I know. I know.

16:36

Hearing it out loud makes me sound insane. So thank you. Okay. Print pitch number one. That's twelve fifteen to one. Then we have pitch number one. So you've you do the research before the pitch, then you take the pitch. Oh, yeah. That's interesting. Usually, I start the call And then they see my eyes frantically going around the screen while I'm looking for, like, shit. Did I get who is this? What is the deck? What is the name of this company? And I'll just be like, let's just before we talk about your company, just tell me about yourself while I go look at what company you are.

Hearing it out loud makes me sound insane. So thank you. Okay. Print pitch number one. That's twelve fifteen to one. Then we have pitch number one. So you've you do the research before the pitch, then you take the pitch. Oh, yeah. That's interesting. Usually, I start the call And then they see my eyes frantically going around the screen while I'm looking for, like, shit. Did I get who is this? What is the deck? What is the name of this company? And I'll just be like, let's just before we talk about your company, just tell me about yourself while I go look at what company you are.

17:02

Alright. So so you're doing your research. You do your pitch.

Alright. So so you're doing your research. You do your pitch.

17:05

Next step. So you do immediate follow ups. You do your second pitch, prep second pitch second pitch follow-up,

Next step. So you do immediate follow ups. You do your second pitch, prep second pitch second pitch follow-up,

17:11

text triage. What's that? Like, text, your text messages? Yeah. I am horrible at responding to text messages. I will read them. I will think that I responded and then I'll reply, like, four days later. And so I actually blocked time in my calendar to go through all of the texts that I'm getting throughout the day. Do you actually follow this I do. I do. And I will say for people,

text triage. What's that? Like, text, your text messages? Yeah. I am horrible at responding to text messages. I will read them. I will think that I responded and then I'll reply, like, four days later. And so I actually blocked time in my calendar to go through all of the texts that I'm getting throughout the day. Do you actually follow this I do. I do. And I will say for people,

17:32

that aren't aren't in venture or aren't doing early, early stage startups,

that aren't aren't in venture or aren't doing early, early stage startups,

17:37

A lot of thing is done over text and over phone calls. It's a highly inefficient process. It's not like corporate where

A lot of thing is done over text and over phone calls. It's a highly inefficient process. It's not like corporate where

17:44

you know, everyone's on email and everyone's on slack. It's mostly through one on one text.

you know, everyone's on email and everyone's on slack. It's mostly through one on one text.

17:49

So, we'll just round it off. So we're going email processing part two then ad hoc strategy. What does that mean?

So, we'll just round it off. So we're going email processing part two then ad hoc strategy. What does that mean?

17:56

Ad hoc strategy is, so part of the the goal of work life is we help a lot on go to market. And so typically we're working through various different go to market strategies for certain companies. Gotcha. Then you do a virtual dinner, amazing,

Ad hoc strategy is, so part of the the goal of work life is we help a lot on go to market. And so typically we're working through various different go to market strategies for certain companies. Gotcha. Then you do a virtual dinner, amazing,

18:10

life admin, So that's, like, you know, what, laundry? Was that code for laundry?

life admin, So that's, like, you know, what, laundry? Was that code for laundry?

18:15

When I when I published this, it was around the time I was I had a crazy backlog of just, like, random things. Like, I woke up one morning. It was, like, my driver's license is expired. My passport is expired. I haven't left my house in a year. Like, I need to get my life in order.

When I when I published this, it was around the time I was I had a crazy backlog of just, like, random things. Like, I woke up one morning. It was, like, my driver's license is expired. My passport is expired. I haven't left my house in a year. Like, I need to get my life in order.

18:29

And so that was the week that this set this was screenshots and published. There you go. Alright. E evening block from eight PM to eleven PM, and then what, at bedtime, eleven PM? Yeah. Usually. Okay. Do you think that's amazing. We wanna get weird. I I have an Eight Sleep as well, and so I could probably, like, throw in my sleep data if we wanna get really weird. Do do you so I I,

And so that was the week that this set this was screenshots and published. There you go. Alright. E evening block from eight PM to eleven PM, and then what, at bedtime, eleven PM? Yeah. Usually. Okay. Do you think that's amazing. We wanna get weird. I I have an Eight Sleep as well, and so I could probably, like, throw in my sleep data if we wanna get really weird. Do do you so I I,

18:48

I try to, like, I say no to everything. I think Sean, you might be the same way, but for my I try to have nothing on my calendar. I don't wanna talk to anyone ever.

I try to, like, I say no to everything. I think Sean, you might be the same way, but for my I try to have nothing on my calendar. I don't wanna talk to anyone ever.

18:57

And, like, a meeting to me is, like, a really big deal. Like, I just don't wanna do it. At which, they gave me an EA, and I was, like, oh, so great. First time having a EA? What what do you do? And they were like, oh, like, calendaring. I mean, I manage your calendar. If you wanna book meetings, I'll book them for you. If people wanna book you, I'll do it. And I was like, oh, okay. Alright.

And, like, a meeting to me is, like, a really big deal. Like, I just don't wanna do it. At which, they gave me an EA, and I was, like, oh, so great. First time having a EA? What what do you do? And they were like, oh, like, calendaring. I mean, I manage your calendar. If you wanna book meetings, I'll book them for you. If people wanna book you, I'll do it. And I was like, oh, okay. Alright.

19:16

Look, you're gonna love me. This is the easiest task ever. Somebody asked for a meeting. Just say, hey. He he asked if you could slack him instead. And then if I ask you for a meeting, just say, are you sure? And just delete all the group meetings in the next three weeks. Just delete them and I'll add them back in if they were important. And so, basically, her job was just to make sure nothing gets on the calendar rather than taking things off or rather than putting these on.

Look, you're gonna love me. This is the easiest task ever. Somebody asked for a meeting. Just say, hey. He he asked if you could slack him instead. And then if I ask you for a meeting, just say, are you sure? And just delete all the group meetings in the next three weeks. Just delete them and I'll add them back in if they were important. And so, basically, her job was just to make sure nothing gets on the calendar rather than taking things off or rather than putting these on.

19:39

Do you think that,

Do you think that,

19:41

this calendar has

this calendar has

19:43

being this disciplined? Do you think it's helped you? Because it's I mean, I'm looking at, like, I'm trying to find all the unfair advantages to how you kinda came up so fast. Probably not gonna say it sucks.

being this disciplined? Do you think it's helped you? Because it's I mean, I'm looking at, like, I'm trying to find all the unfair advantages to how you kinda came up so fast. Probably not gonna say it sucks.

19:54

I can tell you I can tell you pros and cons pro pros to the pros to the insane calendar is it did provide a lot of I felt that working from home,

I can tell you I can tell you pros and cons pro pros to the pros to the insane calendar is it did provide a lot of I felt that working from home,

20:04

I am not the best at working from home. I will say that. And so the structure has been really helpful.

I am not the best at working from home. I will say that. And so the structure has been really helpful.

20:09

It's been great. The reason for a lot of the,

It's been great. The reason for a lot of the,

20:14

new routines

new routines

20:15

is because I do have a team now. So I have a team of five people behind the scenes, and so I need to make sure that the the firm is running accordingly. And so I think having that structure is really helpful.

is because I do have a team now. So I have a team of five people behind the scenes, and so I need to make sure that the the firm is running accordingly. And so I think having that structure is really helpful.

20:26

I also find it does help me say no and to have specific moments throughout the day where I text founders or jump on a call, just because I I had talked to a lot of traditional venture capitalists. And if you ask them how they spend their week or if you ask, like, you know, what did on Friday, Friday afternoon, like, what did you do this week? It would all be a blur because there's so much activity and so many things that are happening. And so I found quantifying it a little bit was a nice way for me to at least establish some of these routines. Like, will I continue doing this forever? Probably not. But it's at least something that was helpful,

I also find it does help me say no and to have specific moments throughout the day where I text founders or jump on a call, just because I I had talked to a lot of traditional venture capitalists. And if you ask them how they spend their week or if you ask, like, you know, what did on Friday, Friday afternoon, like, what did you do this week? It would all be a blur because there's so much activity and so many things that are happening. And so I found quantifying it a little bit was a nice way for me to at least establish some of these routines. Like, will I continue doing this forever? Probably not. But it's at least something that was helpful,

20:59

when getting the firm off the ground.

when getting the firm off the ground.

21:01

And, Sam, we were looking at that that spreadsheet of,

And, Sam, we were looking at that that spreadsheet of,

21:05

what do VCs make? I think we should talk about that. So this is one of VCs. This is you wanna pull that. Do. Yeah.

what do VCs make? I think we should talk about that. So this is one of VCs. This is you wanna pull that. Do. Yeah.

21:11

So the the grab the list. The reason why go ahead. You find it, Sean, and then I'll talk the so

So the the grab the list. The reason why go ahead. You find it, Sean, and then I'll talk the so

21:17

brie brie, the one of the reasons why I'm prodding you so much is this whole VC world

brie brie, the one of the reasons why I'm prodding you so much is this whole VC world

21:22

it it kind of,

it it kind of,

21:23

I I just, like, I I can't tell if I'm just low IQ. I just it's really hard for me to understand, like, how the money actually gets in debris's pocket. You know, like, how I understand you invest it. I understand you,

I I just, like, I I can't tell if I'm just low IQ. I just it's really hard for me to understand, like, how the money actually gets in debris's pocket. You know, like, how I understand you invest it. I understand you,

21:36

invest in in in startups and you wait ten years to sell, but, like, sometimes I'm curious, like, Okay. But how much money can you actually make? And so we recently found I have no idea how we how our friend found it, a spreadsheet that I think it's all

invest in in in startups and you wait ten years to sell, but, like, sometimes I'm curious, like, Okay. But how much money can you actually make? And so we recently found I have no idea how we how our friend found it, a spreadsheet that I think it's all

21:50

user submitted salaries

user submitted salaries

21:52

and carry numbers

and carry numbers

21:54

of maybe like a thousand different VCs You wanna read it read that off. Yeah. I'm trying to find it. It's it's a little bit hard to find here while while we're while we're live. But basically,

of maybe like a thousand different VCs You wanna read it read that off. Yeah. I'm trying to find it. It's it's a little bit hard to find here while while we're while we're live. But basically,

22:04

I don't know if you could do it, Sam, if you could find it. But basically, it it broke it down by fun size. So it's like, alright. If, so you were pe people were volunteering their information. Here's what I make as my base come here's what I make as a bonus, and here's what my carry is. And it was like, you know, my fund is zero to fifty million, fifty million to a hundred million, hundred to two hundred fifty million, and then, like, all the way up to a two billion plus fund.

I don't know if you could do it, Sam, if you could find it. But basically, it it broke it down by fun size. So it's like, alright. If, so you were pe people were volunteering their information. Here's what I make as my base come here's what I make as a bonus, and here's what my carry is. And it was like, you know, my fund is zero to fifty million, fifty million to a hundred million, hundred to two hundred fifty million, and then, like, all the way up to a two billion plus fund.

22:25

And,

And,

22:26

and it was it's even there, there's, like, quite a lot of variety. Right? Because not every partner has the same deal, but what it looked to me, like,

and it was it's even there, there's, like, quite a lot of variety. Right? Because not every partner has the same deal, but what it looked to me, like,

22:33

was that

was that

22:35

for small funds,

for small funds,

22:37

and you correct me if I'm if I'm wrong here. But this this was my my summary of, like, you know, five hundred rows of data. Just eyeballing it. It looked like if you work at a small fund, let's call it

and you correct me if I'm if I'm wrong here. But this this was my my summary of, like, you know, five hundred rows of data. Just eyeballing it. It looked like if you work at a small fund, let's call it

22:47

under a hundred million dollars as your fund size.

under a hundred million dollars as your fund size.

22:51

The good news is, you know, you're taking two percent of, let's call it a hundred million. That's two million dollars. And usually, it's just one or two partners, maybe, you know, some some admin people kind of behind the scenes.

The good news is, you know, you're taking two percent of, let's call it a hundred million. That's two million dollars. And usually, it's just one or two partners, maybe, you know, some some admin people kind of behind the scenes.

23:02

But you can you could basically take a a large salary,

But you can you could basically take a a large salary,

23:06

and you have a large percentage of the carry, but you,

and you have a large percentage of the carry, but you,

23:10

but then on the other, it said the small the small funds seem to do pretty well. And then the the really large funds that were, like, a two billion dollar fund, their, you know, their fees itself is insane.

but then on the other, it said the small the small funds seem to do pretty well. And then the the really large funds that were, like, a two billion dollar fund, their, you know, their fees itself is insane.

23:21

Right, two percent of two billion every year that you're taking is is is a large number. And then they're carry,

Right, two percent of two billion every year that you're taking is is is a large number. And then they're carry,

23:27

you know, they're the multiple they're they're expecting to do on a two billion dollar fund. They may they may not five x that fund. They made just two x that fund or three x that fund. And so their carry expectations are different. It looked to me like this. Venture is kinda have, like, a high paying job, maybe four hundred, five hundred thousand dollars a year.

you know, they're the multiple they're they're expecting to do on a two billion dollar fund. They may they may not five x that fund. They made just two x that fund or three x that fund. And so their carry expectations are different. It looked to me like this. Venture is kinda have, like, a high paying job, maybe four hundred, five hundred thousand dollars a year.

23:43

And then if they hit winners, like, you seem to have hit some winners or you have some winners in your portfolio, it sounds like you you you've hit a lot of winners. If those pan out, if Hopin truly does end up as a five to ten billion dollar company,

And then if they hit winners, like, you seem to have hit some winners or you have some winners in your portfolio, it sounds like you you you've hit a lot of winners. If those pan out, if Hopin truly does end up as a five to ten billion dollar company,

23:55

then, you know, you're gonna you're gonna have a a big windfall, which might look more like twenty to fifty million dollars can come your way if these winners pan out and go public and whatnot. So

then, you know, you're gonna you're gonna have a a big windfall, which might look more like twenty to fifty million dollars can come your way if these winners pan out and go public and whatnot. So

24:05

tell me how accurate that is or, like, put differently.

tell me how accurate that is or, like, put differently.

24:09

What are your expectations on? Like, how much you can make doing this thing you're doing now?

What are your expectations on? Like, how much you can make doing this thing you're doing now?

24:14

Yeah.

Yeah.

24:15

Great question. I wanted to touch on something that Sam said as well.

Great question. I wanted to touch on something that Sam said as well.

24:20

What's interesting when you look at venture capital today is when I was initially starting the firm, I went into this with a belief that venture is or traditional venture is on the decline. I saw angel investors that were getting into really great rounds. I saw,

What's interesting when you look at venture capital today is when I was initially starting the firm, I went into this with a belief that venture is or traditional venture is on the decline. I saw angel investors that were getting into really great rounds. I saw,

24:37

solo capitalists or super angels. Like, I know Scott Bellsey has been on the show. Ilaud Gil is a close friend and someone that's deploying a lot of capital. I mean, a capital that looks like almost a large top tier firm. And so I saw that individuals were doing the work that, you know, a twenty to thirty person venture firm were doing.

solo capitalists or super angels. Like, I know Scott Bellsey has been on the show. Ilaud Gil is a close friend and someone that's deploying a lot of capital. I mean, a capital that looks like almost a large top tier firm. And so I saw that individuals were doing the work that, you know, a twenty to thirty person venture firm were doing.

24:58

And so I think it's interesting to see, like, I'm a great case in point where I was in marketing. I went to a state school. I grew up in Ohio. Like, I'm, by no means, a pedigree person, but

And so I think it's interesting to see, like, I'm a great case in point where I was in marketing. I went to a state school. I grew up in Ohio. Like, I'm, by no means, a pedigree person, but

25:08

have been able to build a track record. I have been able to raise outside money, and I think this is just, like, the very, very early days for what's about happen where there will be a lot more people that look like me, and there will be a lot more people that start their own firms

have been able to build a track record. I have been able to raise outside money, and I think this is just, like, the very, very early days for what's about happen where there will be a lot more people that look like me, and there will be a lot more people that start their own firms

25:21

because I think it's one of these things where, like, the nature of venture is changing. And my investors like smaller funds because you have one of those higher return profiles

because I think it's one of these things where, like, the nature of venture is changing. And my investors like smaller funds because you have one of those higher return profiles

25:32

as opposed to some of the larger

as opposed to some of the larger

25:34

institutions

institutions

25:36

that their multiples coming down over time, and many of those LPs are having a hard time getting access to those funds at all.

that their multiples coming down over time, and many of those LPs are having a hard time getting access to those funds at all.

25:43

So a guy like,

So a guy like,

25:45

so who what was the guy's name? Alad Gil, is that how you say his name? I've read a great book by him. I forget operator's manual. I think it was called No. It's some high growth startups or something like that. High growth handbook.

so who what was the guy's name? Alad Gil, is that how you say his name? I've read a great book by him. I forget operator's manual. I think it was called No. It's some high growth startups or something like that. High growth handbook.

25:57

Handbuck, manual handbook.

Handbuck, manual handbook.

25:58

Yeah, it was good. That was a great that was a great book. I had I hadn't heard of this guy, but, like, I see him everywhere. And so is this just basically an incredibly

Yeah, it was good. That was a great that was a great book. I had I hadn't heard of this guy, but, like, I see him everywhere. And so is this just basically an incredibly

26:07

high net worth liquid person who just writes massive checks to

high net worth liquid person who just writes massive checks to

26:11

hundreds of startups a year? Is that just I mean, is it as simple as that?

hundreds of startups a year? Is that just I mean, is it as simple as that?

26:16

In a lot's case, it's a combination of personal capital plus outside money as well. I will say that a lot of the solo capitalists. I mean, even the,

In a lot's case, it's a combination of personal capital plus outside money as well. I will say that a lot of the solo capitalists. I mean, even the,

26:26

you know, my fun size is primarily

you know, my fun size is primarily

26:28

my first check-in. I do a lot of PVs, and I do a lot of follow on investing, and that's with a handful of LPs.

my first check-in. I do a lot of PVs, and I do a lot of follow on investing, and that's with a handful of LPs.

26:34

And so many of us, we kind of publish, here's our core strategy, and then behind the scenes, many of have other playbooks that we're running as well. And have you made have you had any returns so far since since you've started?

And so many of us, we kind of publish, here's our core strategy, and then behind the scenes, many of have other playbooks that we're running as well. And have you made have you had any returns so far since since you've started?

26:47

I have. Those have mostly been on the SPB front.

I have. Those have mostly been on the SPB front.

26:50

You know, I I'm I'm setting up,

You know, I I'm I'm setting up,

26:52

special purpose vehicles where I have one or two LPs where they're It's it's primarily their capital. I might write write a small personal check or something small out of the fund alongside that, but I'm starting to see some returns in companies. However, I will say I'm I'm holding on all of those positions.

special purpose vehicles where I have one or two LPs where they're It's it's primarily their capital. I might write write a small personal check or something small out of the fund alongside that, but I'm starting to see some returns in companies. However, I will say I'm I'm holding on all of those positions.

27:08

What do you think is a re because this is what the thing me and Sam talk about, which is, like, With investing, you have you have illiquidity for a long period of time right now, typically. Right? You should invest in a startup. It might take seven, ten years for it to exit.

What do you think is a re because this is what the thing me and Sam talk about, which is, like, With investing, you have you have illiquidity for a long period of time right now, typically. Right? You should invest in a startup. It might take seven, ten years for it to exit.

27:20

And along the way, you're getting these paper markups. And so I guess, like, give us a sense of if you are if you do go the solo capitalist route, and you've would say you're, like, the success case of going the solo capitalist route. There's a lot of people who could try it may not have the same results as you, but let's say things work out.

And along the way, you're getting these paper markups. And so I guess, like, give us a sense of if you are if you do go the solo capitalist route, and you've would say you're, like, the success case of going the solo capitalist route. There's a lot of people who could try it may not have the same results as you, but let's say things work out.

27:37

How do you think about

How do you think about

27:39

because I think a lot of people are trying to decide. Do I do this? Do I start a business? Do I take a job somewhere? Or do I work at a FANG company? Do I what what do I do? And so What do you think's realistic expectations

because I think a lot of people are trying to decide. Do I do this? Do I start a business? Do I take a job somewhere? Or do I work at a FANG company? Do I what what do I do? And so What do you think's realistic expectations

27:49

for if it works? This is what it looks like over, like, a seven year period. Right? The first five years you're just taking kinda your salary, which might be two hundred fifty thousand, might be a little more, a little less.

for if it works? This is what it looks like over, like, a seven year period. Right? The first five years you're just taking kinda your salary, which might be two hundred fifty thousand, might be a little more, a little less.

28:01

And then, like, But you're hoping by year seven or ten, you're able to get this this type of a personal personal win out of it, which makes your average over the ten years look really good. Guess, can you walk us through the numbers? Because I think for most people, this is just a black box. They don't really understand

And then, like, But you're hoping by year seven or ten, you're able to get this this type of a personal personal win out of it, which makes your average over the ten years look really good. Guess, can you walk us through the numbers? Because I think for most people, this is just a black box. They don't really understand

28:14

how the money would what the money could look like in this, if things work out.

how the money would what the money could look like in this, if things work out.

28:19

Yeah.

Yeah.

28:20

I I'm I'm hearing all sorts of variations to this model. I mean, I have friends who are running

I I'm I'm hearing all sorts of variations to this model. I mean, I have friends who are running

28:26

early stage startup. And they've raised, you know, five to twenty million dollars in their deploying capital while they're operating.

early stage startup. And they've raised, you know, five to twenty million dollars in their deploying capital while they're operating.

28:33

I think that's the best case scenario. I mean, if you're ready to start a startup, and you have CEO potential and you know exactly what you wanna build, that is gonna have a much higher,

I think that's the best case scenario. I mean, if you're ready to start a startup, and you have CEO potential and you know exactly what you wanna build, that is gonna have a much higher,

28:43

you know, your your building a legacy there, you have the ability to hire people. Like, those people will even start startups. Like, I just think there's so many great things when CEOs are active angel investors.

you know, your your building a legacy there, you have the ability to hire people. Like, those people will even start startups. Like, I just think there's so many great things when CEOs are active angel investors.

28:53

That's why I chose to raise from a lot of founders and not traditional LPs or, you know, traditional finance financial institutions.

That's why I chose to raise from a lot of founders and not traditional LPs or, you know, traditional finance financial institutions.

29:01

I think they have a lot more access and they have the ability

I think they have a lot more access and they have the ability

29:05

to invest in startups opportunistically,

to invest in startups opportunistically,

29:07

not as their full time thing while they still have really great access in mind sharing the ecosystem. You know, for individuals like myself, like, you know, I had

not as their full time thing while they still have really great access in mind sharing the ecosystem. You know, for individuals like myself, like, you know, I had

29:16

ten ish years of of tech company experience. I don't even wanna say start up experience because I was at a big company, and then I was at a second more medium sized tech company. In those scenarios, you know, you

ten ish years of of tech company experience. I don't even wanna say start up experience because I was at a big company, and then I was at a second more medium sized tech company. In those scenarios, you know, you

29:28

Your investors are looking for your ability, you know, have you already built a track record? Do you have an ability to invest in really great companies?

Your investors are looking for your ability, you know, have you already built a track record? Do you have an ability to invest in really great companies?

29:35

And so that's one thing to consider. I actually spent,

And so that's one thing to consider. I actually spent,

29:39

about two solid years of blogging,

about two solid years of blogging,

29:42

tweeting,

tweeting,

29:43

you know, really investing in building my personal brands so I could gear up to go and raise outside money. So I think you have to build a really strong case if you wanna raise from out from outside investors.

you know, really investing in building my personal brands so I could gear up to go and raise outside money. So I think you have to build a really strong case if you wanna raise from out from outside investors.

29:54

The one thing that I will say,

The one thing that I will say,

29:57

you know, Angelus and Carter have made this incredibly easy. Think the forcing function and venture, which has caused, you know, the ability for anyone to become a VC or to raise their own fund is these platforms, which

you know, Angelus and Carter have made this incredibly easy. Think the forcing function and venture, which has caused, you know, the ability for anyone to become a VC or to raise their own fund is these platforms, which

30:08

based basically connect you with investors. They make it really easy to manage, like, your back office and, you know, you don't have to do what lawyers and all of that stuff. Right. That's the hack. You you don't you dodge my question on how much money you can make, but that's okay. Maybe you don't maybe maybe you don't wanna answer that question. No. Let's go into it. I think this is fun. I mean, this is this is the the title of the podcast. So I think I think we should go into it.

based basically connect you with investors. They make it really easy to manage, like, your back office and, you know, you don't have to do what lawyers and all of that stuff. Right. That's the hack. You you don't you dodge my question on how much money you can make, but that's okay. Maybe you don't maybe maybe you don't wanna answer that question. No. Let's go into it. I think this is fun. I mean, this is this is the the title of the podcast. So I think I think we should go into it.

30:29

I would say so every solo capitalist does it differently.

I would say so every solo capitalist does it differently.

30:32

Some people are purely one person

Some people are purely one person

30:36

they're pocketing all the management fees. They're taking all the carry. I'm actually seeing today, you know, if you're raising a

they're pocketing all the management fees. They're taking all the carry. I'm actually seeing today, you know, if you're raising a

30:41

five

five

30:44

to ten to maybe even twenty five million dollar fund. If you're doing something on AngelList, that's a true solo capitalist fund,

to ten to maybe even twenty five million dollar fund. If you're doing something on AngelList, that's a true solo capitalist fund,

30:51

you can actually take two point five to three percent management fees.

you can actually take two point five to three percent management fees.

30:54

What I did for mine is I did two percent management fees the way that

What I did for mine is I did two percent management fees the way that

30:59

I thought about it because And and the this is a rolling fund?

I thought about it because And and the this is a rolling fund?

31:03

It could be a traditional fund or it could be a rolling fund. So the rolling fund means that structurally you're able to

It could be a traditional fund or it could be a rolling fund. So the rolling fund means that structurally you're able to

31:10

talk about your fund broadly. You're able to market your fund, which historically,

talk about your fund broadly. You're able to market your fund, which historically,

31:15

you know, you weren't able to market your fund when you're actively fundraising.

you know, you weren't able to market your fund when you're actively fundraising.

31:19

You know, if someone has distribution, if you have a podcast,

You know, if someone has distribution, if you have a podcast,

31:22

you know, if you're an active angel investor and you already have great deal flow or you're leaving a high growth startup and you have a great network, rolling funds are great because you can market it, and you can constantly be bringing in new LPs. It's not something where you go out, you raise money, you ask a bunch of people for money, you know, maybe a handful of people say, yes. You do a first close. You go out and ask more people for money. You do a second close. Like, that historically has been a really time consuming process. And as a solo capitalist, how you spend your time is your strategy. And so you don't wanna spend the majority of your week meeting with investors and you're not meeting with startups.

you know, if you're an active angel investor and you already have great deal flow or you're leaving a high growth startup and you have a great network, rolling funds are great because you can market it, and you can constantly be bringing in new LPs. It's not something where you go out, you raise money, you ask a bunch of people for money, you know, maybe a handful of people say, yes. You do a first close. You go out and ask more people for money. You do a second close. Like, that historically has been a really time consuming process. And as a solo capitalist, how you spend your time is your strategy. And so you don't wanna spend the majority of your week meeting with investors and you're not meeting with startups.

31:54

And so it can be,

And so it can be,

31:56

something that really impacts the business model. And so I think that the rolling fund works well if you already have distribution.

something that really impacts the business model. And so I think that the rolling fund works well if you already have distribution.

32:03

If you don't have distribution, you, you know, wanna experiment with raising outside money, oftentimes, the people that are doing this really well are individuals

If you don't have distribution, you, you know, wanna experiment with raising outside money, oftentimes, the people that are doing this really well are individuals

32:10

that

that

32:11

have a valuable network. I mean, maybe they're leaving Stripe or Airbnb or one of these companies where they have a very entrepreneurial culture and the people know, that used to sit across me at work or or likely likely to go leave and start a startup, and they're gonna be able to raise from top tier funds. Like, that's one of strategy as well, where seen many of them go out and raise some outside money or,

have a valuable network. I mean, maybe they're leaving Stripe or Airbnb or one of these companies where they have a very entrepreneurial culture and the people know, that used to sit across me at work or or likely likely to go leave and start a startup, and they're gonna be able to raise from top tier funds. Like, that's one of strategy as well, where seen many of them go out and raise some outside money or,

32:31

you know, there's

you know, there's

32:32

a lot of the startups that have been really successful in the last generation, their alumni actually have WhatsApp groups, and they've created their own syndicates where you can co invest alongside the Airbnb mafia

a lot of the startups that have been really successful in the last generation, their alumni actually have WhatsApp groups, and they've created their own syndicates where you can co invest alongside the Airbnb mafia

32:41

or there's a Stripe group or that's somewhere where I spend a lot of my time where I help a lot of the alumni groups build their first syndicate, and that's been a ton of fun because you get to meet the whole company and you get to really know, understand who are some of the,

or there's a Stripe group or that's somewhere where I spend a lot of my time where I help a lot of the alumni groups build their first syndicate, and that's been a ton of fun because you get to meet the whole company and you get to really know, understand who are some of the,

32:56

power builders, I guess, I would call them, inside the company who are most likely to leave and start something So so what would you say the the potential earning then is for a solo,

power builders, I guess, I would call them, inside the company who are most likely to leave and start something So so what would you say the the potential earning then is for a solo,

33:06

capitalist

capitalist

33:08

to go back to Sean's question? Yeah. It it depends on your goals. I mean, I'm seeing solo capitalists that are going out. Maybe you start with a ten to twenty five million dollar fund one.

to go back to Sean's question? Yeah. It it depends on your goals. I mean, I'm seeing solo capitalists that are going out. Maybe you start with a ten to twenty five million dollar fund one.

33:19

For how quickly,

For how quickly,

33:20

the fundraising climate is moving today, you know, in the next twelve months, you could go out and raise, you know, forty eight to sixty million dollar fund too.

the fundraising climate is moving today, you know, in the next twelve months, you could go out and raise, you know, forty eight to sixty million dollar fund too.

33:29

The interesting thing is, like, this isn't purely a new model. I think what's changed is that the type of people that are starting funds

The interesting thing is, like, this isn't purely a new model. I think what's changed is that the type of people that are starting funds

33:37

do look very different from the last generation.

do look very different from the last generation.

33:40

Like, I look at,

Like, I look at,

33:42

Idon, Sandcut at Felis. You know, he was a super angel and then started Felisa Ventures.

Idon, Sandcut at Felis. You know, he was a super angel and then started Felisa Ventures.

33:47

Mike Maples, who's been on the show, you know, Mike was a super angel and then he started floodgate. I think what's different today is how fast, you can make money because there are SPVs

Mike Maples, who's been on the show, you know, Mike was a super angel and then he started floodgate. I think what's different today is how fast, you can make money because there are SPVs

33:57

and ways for individuals to invest in later stage companies. Like, early stage is one thing, but I think later stage is where a lot of people are finding

and ways for individuals to invest in later stage companies. Like, early stage is one thing, but I think later stage is where a lot of people are finding

34:05

great returns in a short amount of time. So you have your twenty five million dollar fund as the operator. What do you expect your your your pay to be?

great returns in a short amount of time. So you have your twenty five million dollar fund as the operator. What do you expect your your your pay to be?

34:15

It's a good question. I mean, as as you said earlier, I mean, a lot of people are holding for the long term, and so I wouldn't bank on carry in the first, you know, seven to ten years,

It's a good question. I mean, as as you said earlier, I mean, a lot of people are holding for the long term, and so I wouldn't bank on carry in the first, you know, seven to ten years,

34:25

but you do get a a reasonable salary because many solo capitalists are due taking two point five to three percent management fees. So two point five two point five percent of twenty five is is what? I don't even know. I can't do math in my head.

but you do get a a reasonable salary because many solo capitalists are due taking two point five to three percent management fees. So two point five two point five percent of twenty five is is what? I don't even know. I can't do math in my head.

34:39

So that's a this is a great line. Go ahead. On Palm's podcast, you know, somebody asked him this question. They're like, wait, if somebody has a hundred thousand Bitcoin and Bitcoin goes to seven hundred fifty thousand, how much is that worth? And he just goes, I don't do public math.

So that's a this is a great line. Go ahead. On Palm's podcast, you know, somebody asked him this question. They're like, wait, if somebody has a hundred thousand Bitcoin and Bitcoin goes to seven hundred fifty thousand, how much is that worth? And he just goes, I don't do public math.

34:52

I think of what? They're like, what what did you just say? He goes, I don't do public math. You don't do math in public? He's like, yeah. I don't do public math. And I just was like, that's actually a great policy. I don't do public math.

I think of what? They're like, what what did you just say? He goes, I don't do public math. You don't do math in public? He's like, yeah. I don't do public math. And I just was like, that's actually a great policy. I don't do public math.

35:03

So two two point five of twenty five is so, yeah, have six hundred and twenty five thousand dollars a year in salary off a twenty five million dollar fund. And then the carry a fee. Sorry. And then if that and if your solo that, yeah, that's a great living. And then what what what would you estimate you could do at your fund? Three exit, four exit. We have, like, a target?

So two two point five of twenty five is so, yeah, have six hundred and twenty five thousand dollars a year in salary off a twenty five million dollar fund. And then the carry a fee. Sorry. And then if that and if your solo that, yeah, that's a great living. And then what what what would you estimate you could do at your fund? Three exit, four exit. We have, like, a target?

35:22

Right now, it's north of five x.

Right now, it's north of five x.

35:25

Damn. Alright. So five x. So that's a hundred,

Damn. Alright. So five x. So that's a hundred,

35:28

for a hundred well, I can't. I don't It's a hundred twenty five million. A hundred twenty five million. You pay you pay back the twenty five first. So now there's a hundred million of profit of the hundred twenty hundred million of profit. You keep twenty percent. That's twenty million. So you might make twenty million at the sort of in the in the termination of the fund basically after after ten years.

for a hundred well, I can't. I don't It's a hundred twenty five million. A hundred twenty five million. You pay you pay back the twenty five first. So now there's a hundred million of profit of the hundred twenty hundred million of profit. You keep twenty percent. That's twenty million. So you might make twenty million at the sort of in the in the termination of the fund basically after after ten years.

35:46

That sounds amazing. Right?

That sounds amazing. Right?

35:48

It's it's amazing. It's amazing. I also fine. I mean, when once you get into this world,

It's it's amazing. It's amazing. I also fine. I mean, when once you get into this world,

35:56

typically you'll see that's that's the core fund, and the core fund is, like, your v one. Like, that's the first thing you do to build a track record and to, like, get in the game.

typically you'll see that's that's the core fund, and the core fund is, like, your v one. Like, that's the first thing you do to build a track record and to, like, get in the game.

36:05

Where people

Where people

36:06

start to make a lot of money and make a lot of money in the short term is what I mentioned doing SPVs

start to make a lot of money and make a lot of money in the short term is what I mentioned doing SPVs

36:11

or even buying secondary one of the things that I've been doing a lot over the last

or even buying secondary one of the things that I've been doing a lot over the last

36:16

year, year and a half is one of the things that holds people back from starting a startup is the fact that they're

year, year and a half is one of the things that holds people back from starting a startup is the fact that they're

36:23

illiquid and sitting on a lot of equity at their last startup. And so there are a lot of VCs that are exploring, like, what would it mean to

illiquid and sitting on a lot of equity at their last startup. And so there are a lot of VCs that are exploring, like, what would it mean to

36:30

buy shares from, you know, employees

buy shares from, you know, employees

36:33

to then put them in business. And so that's another way to think about it as well. I think there's different playbooks that you can layer on top of each other. Once the fund is in a good place, then you can get more creative with SPVs or you can get more creative with even buying employee shares and companies that still have a lot of upside.

to then put them in business. And so that's another way to think about it as well. I think there's different playbooks that you can layer on top of each other. Once the fund is in a good place, then you can get more creative with SPVs or you can get more creative with even buying employee shares and companies that still have a lot of upside.

36:51

You know, and so I think that becomes pretty creative as well.

You know, and so I think that becomes pretty creative as well.

36:54

Let's switch gears to ideas. So what spaces, what ideas,

Let's switch gears to ideas. So what spaces, what ideas,

36:59

do you have that you think people should be building in or you you see interesting stuff? So give me a sense of, like, it can either be a specific idea or it could be kind of like a trend you're noticing. What what do you got? Yeah. It's interesting. I tend to look at what are

do you have that you think people should be building in or you you see interesting stuff? So give me a sense of, like, it can either be a specific idea or it could be kind of like a trend you're noticing. What what do you got? Yeah. It's interesting. I tend to look at what are

37:12

the smartest people that I know thinking about are working on,

the smartest people that I know thinking about are working on,

37:16

I consistently

I consistently

37:17

see,

see,

37:18

a lot of people are moving into crypto and into climate change. I think these are two areas that you can't really ignore.

a lot of people are moving into crypto and into climate change. I think these are two areas that you can't really ignore.

37:25

And I'm also seeing people leave very well paying jobs that have a lot of equity to work on things like climate change. And so I do think that there are trends that are starting to bubble up that have maybe been

And I'm also seeing people leave very well paying jobs that have a lot of equity to work on things like climate change. And so I do think that there are trends that are starting to bubble up that have maybe been

37:36

either underserved by venture, underfunded, rather. And so it does seem like there's a lot of things that are happening, especially during COVID. I feel like

either underserved by venture, underfunded, rather. And so it does seem like there's a lot of things that are happening, especially during COVID. I feel like

37:45

during the pandemic,

during the pandemic,

37:46

people started reexamining what matters like, you take away the fancy office, you take away all the perks, you

people started reexamining what matters like, you take away the fancy office, you take away all the perks, you

37:54

take away the ability to, you know,

take away the ability to, you know,

37:57

physically

physically

37:58

see your team. And so I'm I'm seeing a lot of people that are leaving to work on things that they actually care about, which is really interesting. Not to say that they won't make a lot of money, but to say that there are new opportunities and new types of companies that people truly wanna build. And so that's been something that I've been thinking about. So what, what's some of the climate yeah. I was gonna ask about climate change and climate tag. That's interesting. Give us a cool idea in climate change that you've seen or you have.

see your team. And so I'm I'm seeing a lot of people that are leaving to work on things that they actually care about, which is really interesting. Not to say that they won't make a lot of money, but to say that there are new opportunities and new types of companies that people truly wanna build. And so that's been something that I've been thinking about. So what, what's some of the climate yeah. I was gonna ask about climate change and climate tag. That's interesting. Give us a cool idea in climate change that you've seen or you have.

38:23

Yeah. I mean, today, it feels like it's very early days. I'm I'm seeing a lot of companies that are thinking about carbon offset or they're coming up with ways for corporations

Yeah. I mean, today, it feels like it's very early days. I'm I'm seeing a lot of companies that are thinking about carbon offset or they're coming up with ways for corporations

38:33

to

to

38:34

be,

be,

38:35

think more

think more

38:36

think in more sustainable ways.

think in more sustainable ways.

38:40

I will say, I mean, a lot of the stuff that's directly related to climate change, I probably don't see because I do a lot of workplace and future of work stuff. I think a lot, I think we're gonna see more specialized firms that are focused on climate change or that are focused on front tier tech. The cool thing about being a solo capitalist and having more of a on, like, this is my area of expertise and this is where I can add value means that when I get together for dinners with other, new solo capitalist or new funds, they're specialized in their own way. And so I do like spending time with experts on climate change and frontier attack. Like, there's so much happening in space right now. Do I have the, you know, the experience or the network to really dig in? Not at this time, but I love hanging out with people that are working on space tech.

I will say, I mean, a lot of the stuff that's directly related to climate change, I probably don't see because I do a lot of workplace and future of work stuff. I think a lot, I think we're gonna see more specialized firms that are focused on climate change or that are focused on front tier tech. The cool thing about being a solo capitalist and having more of a on, like, this is my area of expertise and this is where I can add value means that when I get together for dinners with other, new solo capitalist or new funds, they're specialized in their own way. And so I do like spending time with experts on climate change and frontier attack. Like, there's so much happening in space right now. Do I have the, you know, the experience or the network to really dig in? Not at this time, but I love hanging out with people that are working on space tech.

39:24

And what,

And what,

39:25

in in the work life portfolio,

in in the work life portfolio,

39:28

so future of work, what's,

so future of work, what's,

39:31

What's an idea that that our company that you're excited about that's not already,

What's an idea that that our company that you're excited about that's not already,

39:36

like, well known? It hasn't hasn't had that breakout moment where raises a huge round. So people in tech find out, or everybody's already using it like Slack or something like that. So what what's an example of a company that you think is super cool? Give us one from your portfolio.

like, well known? It hasn't hasn't had that breakout moment where raises a huge round. So people in tech find out, or everybody's already using it like Slack or something like that. So what what's an example of a company that you think is super cool? Give us one from your portfolio.

39:50

Yeah. Absolutely.

Yeah. Absolutely.

39:51

One thing that's not obvious about the work life portfolios, I do spend a lot of time in education and reskilling. I think this is a really important thing where even from your earliest days, like, kids are brought up being asked by their parents, like, what do you wanna be when you grow up? And I think this is sort of a question that historically,

One thing that's not obvious about the work life portfolios, I do spend a lot of time in education and reskilling. I think this is a really important thing where even from your earliest days, like, kids are brought up being asked by their parents, like, what do you wanna be when you grow up? And I think this is sort of a question that historically,

40:09

you know, kids have been taught to do very normal jobs. They're like, well, you should be a teacher, you should be a doctor, you should do, like, these very traditional things.

you know, kids have been taught to do very normal jobs. They're like, well, you should be a teacher, you should be a doctor, you should do, like, these very traditional things.

40:18

There was an interesting,

There was an interesting,

40:20

study that I read when I was, just thinking about work life, building out the first version of the pitch deck, where kids today, there are, you know, kids would rather be YouTubers

study that I read when I was, just thinking about work life, building out the first version of the pitch deck, where kids today, there are, you know, kids would rather be YouTubers

40:30

than they would be astronauts. Like, maybe that change that that changes today because we're now going to space and so space is very cool again.

than they would be astronauts. Like, maybe that change that that changes today because we're now going to space and so space is very cool again.

40:37

But what's interesting there is there isn't really

But what's interesting there is there isn't really

40:41

education that aligns to that. You know, I think the textbook education is you memorize something, you take the task and you forget about it. Like, my recall from elementary school, middle school, high school, is

education that aligns to that. You know, I think the textbook education is you memorize something, you take the task and you forget about it. Like, my recall from elementary school, middle school, high school, is

40:52

zero. Like, I studied for a test. As soon as the test was done, I didn't think about that topic again.

zero. Like, I studied for a test. As soon as the test was done, I didn't think about that topic again.

40:58

But am seeing new platforms and new styles of learning that kids are being taught based on the things they're interested in.

But am seeing new platforms and new styles of learning that kids are being taught based on the things they're interested in.

41:05

I invested in a company called Primer

I invested in a company called Primer

41:08

which is essentially online education.

which is essentially online education.

41:10

I think we're thinking about, like, do we call it homeschooling? I think homeschooling tends to have a fairly negative or, you know, neutral depending on who you are. But the concept is can, you know, eight to ten kids get together and can they learn video game line? Can they learn about, you know, certain types of writing? Can they build their own websites? Like, what are these tangible skills that are aligned to the hobbies and interests of kids that they develop at a very young age. And can they build their own network or community of other like minded kids so they actually care about school.

I think we're thinking about, like, do we call it homeschooling? I think homeschooling tends to have a fairly negative or, you know, neutral depending on who you are. But the concept is can, you know, eight to ten kids get together and can they learn video game line? Can they learn about, you know, certain types of writing? Can they build their own websites? Like, what are these tangible skills that are aligned to the hobbies and interests of kids that they develop at a very young age. And can they build their own network or community of other like minded kids so they actually care about school.

41:43

When I've read so I've been thinking about this whole school thing. It's both Shaan and I have invested in a little bit of it. Shaan teaches a course. I've taught a course of four I've been thinking about school for a little while, and I've actually completely changed my opinion.

When I've read so I've been thinking about this whole school thing. It's both Shaan and I have invested in a little bit of it. Shaan teaches a course. I've taught a course of four I've been thinking about school for a little while, and I've actually completely changed my opinion.

41:56

It was one thing. Now it's the total opposite.

It was one thing. Now it's the total opposite.

41:58

The whole, like, I think that the the everyone talks about education's broken, it's broken, this and that. I think only part of it is. For the top thirty universities,

The whole, like, I think that the the everyone talks about education's broken, it's broken, this and that. I think only part of it is. For the top thirty universities,

42:10

I think are doing

I think are doing

42:12

just wonderful stuff. And here's why Shaan, if, well, you you're different. I didn't go to, like, a fancy school. Brie, if you could have graduated

just wonderful stuff. And here's why Shaan, if, well, you you're different. I didn't go to, like, a fancy school. Brie, if you could have graduated

42:20

if you had to graduate with a quarter of a million dollars in debt, but you could have gone to Harvard. Would you?

if you had to graduate with a quarter of a million dollars in debt, but you could have gone to Harvard. Would you?

42:28

I actually think I would, to be honest. It's totally worth it. I completely agree. It's one hundred percent worth it. It's one hundred percent worth it. If you could get into a top twenty university and you have to get go into a ton of debt, It is one hundred percent worth it. And that if that's the case, it ain't broken. I think it's doing great. If someone's willing to, like, go into the a crippling amount of debt, And go ahead, Scott. Why why okay. Okay. Great. Why do you think it's worth it? Because you learn so much from those great Harvard classes? No. Right? That's not the reason why. You don't learn the the school's not about learning. Cool. So you get the stamp that says I went to Harvard. Yes. So now every time a guy likes Sam or me looks at you, we say, oh, Okay. Yeah. You perk up a little bit. And then the second thing is you get the network. Right? So you're gonna bump into, you know, the next Winkle Voss and Zuckerberg and whoever else, that's on on your campus at that moment. Right? Those are the two reasons, the stamp and the network.

I actually think I would, to be honest. It's totally worth it. I completely agree. It's one hundred percent worth it. It's one hundred percent worth it. If you could get into a top twenty university and you have to get go into a ton of debt, It is one hundred percent worth it. And that if that's the case, it ain't broken. I think it's doing great. If someone's willing to, like, go into the a crippling amount of debt, And go ahead, Scott. Why why okay. Okay. Great. Why do you think it's worth it? Because you learn so much from those great Harvard classes? No. Right? That's not the reason why. You don't learn the the school's not about learning. Cool. So you get the stamp that says I went to Harvard. Yes. So now every time a guy likes Sam or me looks at you, we say, oh, Okay. Yeah. You perk up a little bit. And then the second thing is you get the network. Right? So you're gonna bump into, you know, the next Winkle Voss and Zuckerberg and whoever else, that's on on your campus at that moment. Right? Those are the two reasons, the stamp and the network.

43:22

Yes. The problem is that there's schools like Belmont University where I went that cost fifty thousand dollars a year. And then they're, like,

Yes. The problem is that there's schools like Belmont University where I went that cost fifty thousand dollars a year. And then they're, like,

43:29

Fuck Belmont. I mean, who's no one knows what Belmont is. They do it provides zero value.

Fuck Belmont. I mean, who's no one knows what Belmont is. They do it provides zero value.

43:34

Like, there's no point. If you go to Belmont, you should quit right now. Yeah. And, basically, the only way that we should solve education, I think, is by letting those businesses just go out of business and die and then keeping the top twenties. The top twenty ish.

Like, there's no point. If you go to Belmont, you should quit right now. Yeah. And, basically, the only way that we should solve education, I think, is by letting those businesses just go out of business and die and then keeping the top twenties. The top twenty ish.

43:48

I agree with that. I mean, the liberal arts schools are hurting a lot. I think the forty, fifty, sixty thousand dollar a year school. I mean, I I grew up in Ohio and there's no shortage of, like, liberal arts colleges that have a beautiful campus, but, you know, is it the type of school that someone's going to pull your resume and put it at the top of the pile, or in the era of today, we have AI that's scanning resumes and they're scanning specifically for Harvard Stanford, MI T. Like, those are the people that have the one up. And so I I do agree with that.

I agree with that. I mean, the liberal arts schools are hurting a lot. I think the forty, fifty, sixty thousand dollar a year school. I mean, I I grew up in Ohio and there's no shortage of, like, liberal arts colleges that have a beautiful campus, but, you know, is it the type of school that someone's going to pull your resume and put it at the top of the pile, or in the era of today, we have AI that's scanning resumes and they're scanning specifically for Harvard Stanford, MI T. Like, those are the people that have the one up. And so I I do agree with that.

44:20

Yeah. That's nice. Well, I think I think but you're saying, you know, you you've you changed your opinion. Did you think that before that Harvard was a waste of money? Did you really think that's it? It was, like, good old hunting. Like, you know, like, Yeah. Like, you're gonna go. You know, for, like, for, like, eight eight dollars of late fees, you know, yada yada yada.

Yeah. That's nice. Well, I think I think but you're saying, you know, you you've you changed your opinion. Did you think that before that Harvard was a waste of money? Did you really think that's it? It was, like, good old hunting. Like, you know, like, Yeah. Like, you're gonna go. You know, for, like, for, like, eight eight dollars of late fees, you know, yada yada yada.

44:37

Yeah. I mean, you want that romantic crap to to be true, but it's not. My wife went to an Ivy League School. I was such a redneck when she said she went to Penn. I was like, Oh, is that where that football rapist coach went? That sucks.

Yeah. I mean, you want that romantic crap to to be true, but it's not. My wife went to an Ivy League School. I was such a redneck when she said she went to Penn. I was like, Oh, is that where that football rapist coach went? That sucks.

44:50

And then she was like, no. It's part of the Ivy League. I'm like, I really don't know what that means. I think I've heard about that in, like, a Harry Potter book, but,

And then she was like, no. It's part of the Ivy League. I'm like, I really don't know what that means. I think I've heard about that in, like, a Harry Potter book, but,

44:58

and, like, then I met her friends, and I was like, well, this is totally worth it. One hundred percent worth it when I was good. I actually I have a bit of FOMO. I I very rarely have FOMO, but going back to

and, like, then I met her friends, and I was like, well, this is totally worth it. One hundred percent worth it when I was good. I actually I have a bit of FOMO. I I very rarely have FOMO, but going back to

45:10

my crazy psychotic calendar.

my crazy psychotic calendar.

45:12

The virtual dinner on Wednesdays is with friends that are VCs that all went to Stanford GSB together. And so I'm the only non GS beer on this virtual dinner we used to meet and have dinner in person. We weren't always internet friends, but What's interesting there is once you start having dinner and getting to know them, you're like, shit. I could have been, like, hanging out with you for two years all the time, like, grabbing lunch, hanging out, white boarding, coming up with startup ideas. Like, the whole concept to me makes a ton of sense because once you start start spending time with,

The virtual dinner on Wednesdays is with friends that are VCs that all went to Stanford GSB together. And so I'm the only non GS beer on this virtual dinner we used to meet and have dinner in person. We weren't always internet friends, but What's interesting there is once you start having dinner and getting to know them, you're like, shit. I could have been, like, hanging out with you for two years all the time, like, grabbing lunch, hanging out, white boarding, coming up with startup ideas. Like, the whole concept to me makes a ton of sense because once you start start spending time with,

45:43

friends that do have an Ivy Lake education. You just feel a little bit jealous because they got to hang out a lot more.

friends that do have an Ivy Lake education. You just feel a little bit jealous because they got to hang out a lot more.

45:49

When I was at college. So I went to Duke, which is kind of like more like more like what you're talking about, Sam. And,

When I was at college. So I went to Duke, which is kind of like more like more like what you're talking about, Sam. And,

45:56

I remember after my halfway through my freshman year or something. I called my dad And I was like, hey,

I remember after my halfway through my freshman year or something. I called my dad And I was like, hey,

46:01

you know, before I came here, we had been thinking, like, should I go to state school, like, I go to University of Texas,

you know, before I came here, we had been thinking, like, should I go to state school, like, I go to University of Texas,

46:07

or should I go to Duke? And, like,

or should I go to Duke? And, like,

46:09

you know, I'm not doing so great here. Like, I kind of, like, you know, I'm, like, a b minus student type of thing. And I was, like, I'm, I'm at first, I wasn't trying. Now I'm trying, but I'm still a b minus student even are trying because, like, the kids here are just, like, everyone here is, like, the smartest kid from their their high school. So, like, they're they're all smarter than me, and then they all already work harder than me. I'm just, like, learning to work hard.

you know, I'm not doing so great here. Like, I kind of, like, you know, I'm, like, a b minus student type of thing. And I was, like, I'm, I'm at first, I wasn't trying. Now I'm trying, but I'm still a b minus student even are trying because, like, the kids here are just, like, everyone here is, like, the smartest kid from their their high school. So, like, they're they're all smarter than me, and then they all already work harder than me. I'm just, like, learning to work hard.

46:31

And so I told him I was like, you know, I feel like if I stay here, I'm just gonna kinda be, like, in the middle of the pack.

And so I told him I was like, you know, I feel like if I stay here, I'm just gonna kinda be, like, in the middle of the pack.

46:37

And I started telling him, I I was like, he's like, well, why do you,

And I started telling him, I I was like, he's like, well, why do you,

46:41

like, you know, I I think you're being hard on yourself. And I was like, no. No. No. Like, my friend, Tafiq is, like, super genius and, like, during the summers, you know, I go home and play NBA two k, and he goes and drives, like, you know, an ambulance on the warfront in Palestine, like, helps people. And, like, my other friend over here, he's doing this other thing. And so I was trying to say that as, like, you know, I'm not really one of them. I think you're wasting a lot of money sending me here. Like, this I'm not gonna be a winner here. I'm gonna be like,

like, you know, I I think you're being hard on yourself. And I was like, no. No. No. Like, my friend, Tafiq is, like, super genius and, like, during the summers, you know, I go home and play NBA two k, and he goes and drives, like, you know, an ambulance on the warfront in Palestine, like, helps people. And, like, my other friend over here, he's doing this other thing. And so I was trying to say that as, like, you know, I'm not really one of them. I think you're wasting a lot of money sending me here. Like, this I'm not gonna be a winner here. I'm gonna be like,

47:10

average or below average as far as the rest of the kids here. And he goes,

average or below average as far as the rest of the kids here. And he goes,

47:14

you're not there for grades.

you're not there for grades.

47:16

You're there because

You're there because

47:17

Tophique is your friend next to you, and that guy's your friend next to you, and that guy's your your friend over there,

Tophique is your friend next to you, and that guy's your friend next to you, and that guy's your your friend over there,

47:22

you being friends with these people, you're not even gonna realize it, but your whole what you think is normal is actually gonna be excellent. Because it's just gonna seem totally a excellent will seem average to you just by spending four years with these people. So don't stress yourself out about the grades. Don't don't worry about all that. You're doing the right thing just by being by being, like, five feet away from all these other people. And I was like, man, that was, like, you know, that's, like, dad hits you with some wisdom. And I didn't even really realize it at the time. I was just like, okay. I guess I'm staying here. But now when I look back, I'm like, wow, that was actually, like, kind of a stroke of genius.

you being friends with these people, you're not even gonna realize it, but your whole what you think is normal is actually gonna be excellent. Because it's just gonna seem totally a excellent will seem average to you just by spending four years with these people. So don't stress yourself out about the grades. Don't don't worry about all that. You're doing the right thing just by being by being, like, five feet away from all these other people. And I was like, man, that was, like, you know, that's, like, dad hits you with some wisdom. And I didn't even really realize it at the time. I was just like, okay. I guess I'm staying here. But now when I look back, I'm like, wow, that was actually, like, kind of a stroke of genius.

47:54

And, on his part.

And, on his part.

47:56

And and so to bring it all back, whenever I hear people talk about, like, the future of education, ed education's broken. I'm like,

And and so to bring it all back, whenever I hear people talk about, like, the future of education, ed education's broken. I'm like,

48:02

Maybe,

Maybe,

48:03

like, it's broken in the sense of, like, I think people shouldn't pay for this stuff unless it is of this caliber,

like, it's broken in the sense of, like, I think people shouldn't pay for this stuff unless it is of this caliber,

48:09

but also I think that a lot of people approaching this this this market, they think, like, well, I just need to make, like, a better mouse trap or like, I need to, just like make it so you can learn more important stuff. And I'm like, I don't think that's actually the right way to go about this. The mistake is

but also I think that a lot of people approaching this this this market, they think, like, well, I just need to make, like, a better mouse trap or like, I need to, just like make it so you can learn more important stuff. And I'm like, I don't think that's actually the right way to go about this. The mistake is

48:26

man, the class we're still teaching, you know, these classes and they were teaching it from textbooks. How boring? I'm gonna teach it. I'm gonna teach better subjects in a better way. And the problem is that people don't choose to go to college

man, the class we're still teaching, you know, these classes and they were teaching it from textbooks. How boring? I'm gonna teach it. I'm gonna teach better subjects in a better way. And the problem is that people don't choose to go to college

48:38

for the classes. They don't choose to go to college with the information. They go because they want the stamp. And they want the social experience, and then they want, you know, the parents need that as an insurance policy.

for the classes. They don't choose to go to college with the information. They go because they want the stamp. And they want the social experience, and then they want, you know, the parents need that as an insurance policy.

48:49

And, you know, so college does many things. And then they solve only the information problem but they don't have a credential. They don't have the social experience. They don't have it for the other five reasons that people actually go to these places. So that that ends up being a big problem.

And, you know, so college does many things. And then they solve only the information problem but they don't have a credential. They don't have the social experience. They don't have it for the other five reasons that people actually go to these places. So that that ends up being a big problem.

49:02

Bree. What of I'm looking at your portfolio right now. Of all these, what do you think is gonna be the biggest hit?

Bree. What of I'm looking at your portfolio right now. Of all these, what do you think is gonna be the biggest hit?

49:10

Right now, Hopin's the most obvious.

Right now, Hopin's the most obvious.

49:13

This is a really special company

This is a really special company

49:16

you know, when they initially raised their first round of funding, I believe they had around four employees.

you know, when they initially raised their first round of funding, I believe they had around four employees.

49:22

I caught up with Johnny last week in there at eight hundred and eight hundred and twenty.

I caught up with Johnny last week in there at eight hundred and eight hundred and twenty.

49:27

So I invested a little over a year ago. They're now valued at five point six five b

So I invested a little over a year ago. They're now valued at five point six five b

49:34

and so they're really building

and so they're really building

49:36

a a really disruptive

a a really disruptive

49:39

platform.

platform.

49:40

I say platform because initially they started out as a way for

I say platform because initially they started out as a way for

49:44

companies and festivals and publications

companies and festivals and publications

49:47

to host conferences online.

to host conferences online.

49:49

They've since then moved into streaming, they're moving into all forms of virtual collaboration and even hybrid collaboration

They've since then moved into streaming, they're moving into all forms of virtual collaboration and even hybrid collaboration

49:57

where

where

49:57

Hopin is being used at in person events as well. And so I feel like this is a company that has

Hopin is being used at in person events as well. And so I feel like this is a company that has

50:03

uncapped upside.

uncapped upside.

50:05

They're making a lot of acquisitions.

They're making a lot of acquisitions.

50:07

You know, they

You know, they

50:09

I've only been around for two years.

I've only been around for two years.

50:12

You know, Johnny was initially based in London. He built Hopin because he had an illness where

You know, Johnny was initially based in London. He built Hopin because he had an illness where

50:19

He had a compromised immune system. He couldn't go to networking events. He was, you know, in his

He had a compromised immune system. He couldn't go to networking events. He was, you know, in his

50:25

early ish mid twenties.

early ish mid twenties.

50:27

And so he built the technology because he needed it. And so, like, the team itself is in it for the right reasons and moving really quickly. And so that's one that I'm super excited about.

And so he built the technology because he needed it. And so, like, the team itself is in it for the right reasons and moving really quickly. And so that's one that I'm super excited about.

50:37

You know, but there are a couple of other ones where

You know, but there are a couple of other ones where

50:41

their stealth They don't have a website yet. They're building quietly behind the scenes, and I'm very excited for those companies to come out as well.

their stealth They don't have a website yet. They're building quietly behind the scenes, and I'm very excited for those companies to come out as well.

50:49

But you can't talk about those right now. I can't talk about those ones. What are they doing?

But you can't talk about those right now. I can't talk about those ones. What are they doing?

50:54

I think two two themes that I'm really excited about. The first one is disrupting venture capital,

I think two two themes that I'm really excited about. The first one is disrupting venture capital,

51:01

and that's controversial because I myself am a venture capitalist, but a number startups that I've invested in are non dilutive ways for

and that's controversial because I myself am a venture capitalist, but a number startups that I've invested in are non dilutive ways for

51:09

people to raise money. Like, I think venture has a very they look for very specific things. Typically, it's more it's more,

people to raise money. Like, I think venture has a very they look for very specific things. Typically, it's more it's more,

51:16

software focused business models,

software focused business models,

51:19

you know, typically it's founders that are in an ecosystem where there are a lot of VCs. I think that's changing, but it's gonna take some time for that to change.

you know, typically it's founders that are in an ecosystem where there are a lot of VCs. I think that's changing, but it's gonna take some time for that to change.

51:28

What's interesting to see is I was a first money an investor in a company called PIP,

What's interesting to see is I was a first money an investor in a company called PIP,

51:33

PIP is non dilutive capital for software companies or now any companies with recurring revenue. That one that that that one's gonna make you a bundle. How how do you end up as the first money in pipe? How does that happen? Yeah.

PIP is non dilutive capital for software companies or now any companies with recurring revenue. That one that that that one's gonna make you a bundle. How how do you end up as the first money in pipe? How does that happen? Yeah.

51:45

I am excited to tell you the story because it's it's it's a typical

I am excited to tell you the story because it's it's it's a typical

51:49

what happened was I was in LA for my birthday.

what happened was I was in LA for my birthday.

51:53

So my birthday is September twelfth. I heard about pipe on September tenth, something like that.

So my birthday is September twelfth. I heard about pipe on September tenth, something like that.

51:59

I was at drinks with friends. They're like, you gotta meet this guy, Harryhurst. He's very

I was at drinks with friends. They're like, you gotta meet this guy, Harryhurst. He's very

52:04

charismatic.

charismatic.

52:05

He's building something in SAS. Like, you gotta meet this guy.

He's building something in SAS. Like, you gotta meet this guy.

52:08

And so I had called a few investors. I was emailing people. I'm like, hey, you know, how do I get an intro to Harry?

And so I had called a few investors. I was emailing people. I'm like, hey, you know, how do I get an intro to Harry?

52:14

Wasn't happening. Wasn't happening. And then finally, on my birthday,

Wasn't happening. Wasn't happening. And then finally, on my birthday,

52:17

I tracked down his phone number.

I tracked down his phone number.

52:19

I text him. I'm like, hey,

I text him. I'm like, hey,

52:21

here's, like, here's who I am, here's what I do. I'm in LA, and it's my birthday. Can I come to your office?

here's, like, here's who I am, here's what I do. I'm in LA, and it's my birthday. Can I come to your office?

52:28

And so

And so

52:29

he,

he,

52:30

you know, we ended up meeting in the middle. He's like, okay,

you know, we ended up meeting in the middle. He's like, okay,

52:33

you don't have to come to our office. We can go to Soho House. And so we we caught up on my birthday. I was super excited about what he's building.

you don't have to come to our office. We can go to Soho House. And so we we caught up on my birthday. I was super excited about what he's building.

52:41

I committed on the spot. I, you know, started the process to wire the money from the parking lot. Like, I'm sitting there on my birthday late to my own birthday, laptop out, doing all of the things to get ready to wire money for this company because I knew if I waited, it wasn't gonna happen.

I committed on the spot. I, you know, started the process to wire the money from the parking lot. Like, I'm sitting there on my birthday late to my own birthday, laptop out, doing all of the things to get ready to wire money for this company because I knew if I waited, it wasn't gonna happen.

52:57

You know, founders are meeting so many angel investors and so many VCs through the process where sometimes I'll to founders and they're like, yeah. Room are so excited to work with you. Two days later, they're like, oh, I completely forgot because it's been a whirlwind.

You know, founders are meeting so many angel investors and so many VCs through the process where sometimes I'll to founders and they're like, yeah. Room are so excited to work with you. Two days later, they're like, oh, I completely forgot because it's been a whirlwind.

53:09

And so I wanted to make sure that that email was sent that we started the process and that I was gonna keep bothering Harry. Like, frankly, we didn't have a relationship, so I was bugging the shit out of him so I could invest in the company. But okay. So take it even a step further. This even though I've I lived in Silicon Valley in San Francisco for eight years, and I felt like I was, you and I probably shared so many friends. Technically, I guess, I was kinda part of it, but not really. But it all, like, this guy Harry, how does he even create this much hype for you to chase him down like that?

And so I wanted to make sure that that email was sent that we started the process and that I was gonna keep bothering Harry. Like, frankly, we didn't have a relationship, so I was bugging the shit out of him so I could invest in the company. But okay. So take it even a step further. This even though I've I lived in Silicon Valley in San Francisco for eight years, and I felt like I was, you and I probably shared so many friends. Technically, I guess, I was kinda part of it, but not really. But it all, like, this guy Harry, how does he even create this much hype for you to chase him down like that?

53:40

There are a couple things. So Harry,

There are a couple things. So Harry,

53:44

it's a disruptive model. I will say that, you know, we've seen,

it's a disruptive model. I will say that, you know, we've seen,

53:50

new ways for founders to raise money, but oftentimes there's misalignment because you'll have

new ways for founders to raise money, but oftentimes there's misalignment because you'll have

53:56

ways for founders to raise money, but it's on unfavorable

ways for founders to raise money, but it's on unfavorable

54:00

terms. No. But it'd be, like, like, sophisticated investors. And so for Harry, he the the initial concept was enough where where investors, like, oh, we need to catch up with him and, like, learn what's going on here. It sounds like you were the first money in, but people were telling you, you gotta meet with this guy. Who are those people? Why were they even saying they weren't already investors in the company,

terms. No. But it'd be, like, like, sophisticated investors. And so for Harry, he the the initial concept was enough where where investors, like, oh, we need to catch up with him and, like, learn what's going on here. It sounds like you were the first money in, but people were telling you, you gotta meet with this guy. Who are those people? Why were they even saying they weren't already investors in the company,

54:19

what was he, you know, who who are these people that were giving you this great tip that you were like, oh, okay. I gotta I gotta meet this guy. And if if they hadn't already invested, because I that makes sense when somebody's invested. They say, hey. I I just invested this thing. It's great. Or you should check it out.

what was he, you know, who who are these people that were giving you this great tip that you were like, oh, okay. I gotta I gotta meet this guy. And if if they hadn't already invested, because I that makes sense when somebody's invested. They say, hey. I I just invested this thing. It's great. Or you should check it out.

54:33

But that wasn't the case here.

But that wasn't the case here.

54:35

That wasn't the case. There were a lot of people that were trying to meet pipe.

That wasn't the case. There were a lot of people that were trying to meet pipe.

54:39

You know, I think A lot of ways when you're fundraising for a company, I always encourage founders, like, many of them get discouraged in the beginning. They're like, no one cares. Like, no one cares until everyone cares. And that's how it always works. Like, the last twelve hours of fundraising is always a mess because once people

You know, I think A lot of ways when you're fundraising for a company, I always encourage founders, like, many of them get discouraged in the beginning. They're like, no one cares. Like, no one cares until everyone cares. And that's how it always works. Like, the last twelve hours of fundraising is always a mess because once people

54:57

Once someone hears that someone else is investing or someone else is interested, it just all snowballs into, like, a huge amount of texts and phone calls and emails

Once someone hears that someone else is investing or someone else is interested, it just all snowballs into, like, a huge amount of texts and phone calls and emails

55:05

And so in Harry's case, he's he's a brilliant fundraiser. I mean, if you look at the cap table, he's raised from the CEO

And so in Harry's case, he's he's a brilliant fundraiser. I mean, if you look at the cap table, he's raised from the CEO

55:13

or, you know, one of the co founders every major SaaS company. And so I give him a lot of credit for that. From the earliest days,

or, you know, one of the co founders every major SaaS company. And so I give him a lot of credit for that. From the earliest days,

55:21

you know, he

you know, he

55:22

had a conversation

had a conversation

55:23

with David Sachs. So, you know, David had started Gamma and and and David was very interested in it. For the same reason that I was interested. For me,

with David Sachs. So, you know, David had started Gamma and and and David was very interested in it. For the same reason that I was interested. For me,

55:32

As a first money and investor,

As a first money and investor,

55:34

pipe is a great resource where when a company hits a certain inflection point and they're thinking about raising more money,

pipe is a great resource where when a company hits a certain inflection point and they're thinking about raising more money,

55:41

It's great for me. It's great for the founders. It's great for anyone that's been involved from the very beginning to introduce options of non dilutive financing.

It's great for me. It's great for the founders. It's great for anyone that's been involved from the very beginning to introduce options of non dilutive financing.

55:51

It's more upside for us. It's better for employees, like, all the way around. I'm like, I wanna spend time with this company and ultimately get work life companies to use it when it makes sense.

It's more upside for us. It's better for employees, like, all the way around. I'm like, I wanna spend time with this company and ultimately get work life companies to use it when it makes sense.

56:00

And so that was part of it as well. So then it was basically so did did he know David?

And so that was part of it as well. So then it was basically so did did he know David?

56:07

I believe

I believe

56:08

Harry meant

Harry meant

56:10

someone on David's team that's LA based. And just like a cold email or something? Something like that.

someone on David's team that's LA based. And just like a cold email or something? Something like that.

56:16

So that that's kind of interesting. So, like, I mean, it's just like a it's a huge game of telephone and it's fascinating. This is just a fascinating thing. What what is pipe valued at two or three billion dollars?

So that that's kind of interesting. So, like, I mean, it's just like a it's a huge game of telephone and it's fascinating. This is just a fascinating thing. What what is pipe valued at two or three billion dollars?

56:28

North of two now. Yeah. Okay. So they don't have that much revenue. Like, everyone, it's

North of two now. Yeah. Okay. So they don't have that much revenue. Like, everyone, it's

56:34

it's just crazy that you could say that they're probably gonna grow into that and become way bigger, but they created all this off of, like, a really good story and very strategically

it's just crazy that you could say that they're probably gonna grow into that and become way bigger, but they created all this off of, like, a really good story and very strategically

56:44

getting in the right years, and I think that's incredibly fascinating and really, really cool. It also just speaks to the amount of capital that's available in the ecosystem right now. I think oftentimes these value are getting out of hand because there's so much demand from the last round or there

getting in the right years, and I think that's incredibly fascinating and really, really cool. It also just speaks to the amount of capital that's available in the ecosystem right now. I think oftentimes these value are getting out of hand because there's so much demand from the last round or there

57:00

is so much money where investors

is so much money where investors

57:03

would rather pay a high pay a premium

would rather pay a high pay a premium

57:06

to have exposure to the company and to share in some of that upside than waiting until, you know, a traditional milestone or metric or

to have exposure to the company and to share in some of that upside than waiting until, you know, a traditional milestone or metric or

57:14

moment in time where historically they would have fundraised,

moment in time where historically they would have fundraised,

57:17

like, to give you context and I and I don't say this,

like, to give you context and I and I don't say this,

57:20

as someone who wants to brag by any means, but when invested on pipe. It was at, like, a nine post.

as someone who wants to brag by any means, but when invested on pipe. It was at, like, a nine post.

57:26

And now they're worth north of two billion. And so that's not saying, like, wow, you're a world class investor, like, you've changed this company,

And now they're worth north of two billion. And so that's not saying, like, wow, you're a world class investor, like, you've changed this company,

57:34

but it's to say that when you have a big vision, you have a good team that's building it, when you have a founder that's exceptional at fundraising, like, investors will come to you, and they'll come to you even before,

but it's to say that when you have a big vision, you have a good team that's building it, when you have a founder that's exceptional at fundraising, like, investors will come to you, and they'll come to you even before,

57:45

you know, the next financing round because they wanna get in. So how much you're gonna make off that one?

you know, the next financing round because they wanna get in. So how much you're gonna make off that one?

57:50

I'm holding.

I'm holding.

57:52

It's hard to say. I'm holding. Just what's your stake worth?

It's hard to say. I'm holding. Just what's your stake worth?

57:57

I don't know if I'm allowed to say that. Am I I'm not sure what the rules are. I don't know if I'm allowed to say

I don't know if I'm allowed to say that. Am I I'm not sure what the rules are. I don't know if I'm allowed to say

58:04

that.

that.

58:05

Did, a hundred and fifty k and then I'm continuing to follow on? Well, so, like, there's a lot of math here that involves dilution, but you just told us the you you just told us to you know, the variables, we could do the math. But but we don't do public math if you recall. So We don't do public math.

Did, a hundred and fifty k and then I'm continuing to follow on? Well, so, like, there's a lot of math here that involves dilution, but you just told us the you you just told us to you know, the variables, we could do the math. But but we don't do public math if you recall. So We don't do public math.

58:22

You the number, but we don't do public math. We should we should write it.

You the number, but we don't do public math. We should we should write it.

58:25

You could do, like, all this evaluation. Might be like, well, if it's worth, two billion and you invested at ten ten million dollars. I mean, like, in a hundred and twenty five grand, like, you know, you could do the math. It's it's a whole lot. I just don't know. You know, don't don't do math. It has on so on paper, it has returned the fund. And so I I have returned the fund in the the first year and a half.

You could do, like, all this evaluation. Might be like, well, if it's worth, two billion and you invested at ten ten million dollars. I mean, like, in a hundred and twenty five grand, like, you know, you could do the math. It's it's a whole lot. I just don't know. You know, don't don't do math. It has on so on paper, it has returned the fund. And so I I have returned the fund in the the first year and a half.

58:47

Which is an interesting point. I I think a lot of,

Which is an interesting point. I I think a lot of,

58:50

investors are very quick to scale a fund size. Like, they wanna go out and raise a hundred million dollar fund. For fund one to raise a little bit north of ten million and to return it in the first year and a half, like, that's a pretty safe bet.

investors are very quick to scale a fund size. Like, they wanna go out and raise a hundred million dollar fund. For fund one to raise a little bit north of ten million and to return it in the first year and a half, like, that's a pretty safe bet.

59:02

And one where I didn't overextend myself in a way where it could impact my reputation.

And one where I didn't overextend myself in a way where it could impact my reputation.

59:07

That's something that I do encourage people. I'm like, start with where you are today.

That's something that I do encourage people. I'm like, start with where you are today.

59:11

And find ways to keep building concentration over time, do SPVs, buy secondarily, do whatever it takes to, like, hit that annual number that you need to make to be happy.

And find ways to keep building concentration over time, do SPVs, buy secondarily, do whatever it takes to, like, hit that annual number that you need to make to be happy.

59:20

Don't necessarily overextend yourself and go out and try to raise a hundred million dollar fund. I wouldn't have been able to raise a hundred million dollar fund, but I I have been able to return it on paper very quickly.

Don't necessarily overextend yourself and go out and try to raise a hundred million dollar fund. I wouldn't have been able to raise a hundred million dollar fund, but I I have been able to return it on paper very quickly.

59:30

Right. Well, congratulations.

Right. Well, congratulations.

59:32

And so, we should wrap it up a little bit over over time and we saw her calendar. So we know we're we're eating into like a Peloton class or like a meeting or or email processing, maybe. We don't know exactly which one. But Tuxing triage. Tuxing.

And so, we should wrap it up a little bit over over time and we saw her calendar. So we know we're we're eating into like a Peloton class or like a meeting or or email processing, maybe. We don't know exactly which one. But Tuxing triage. Tuxing.

59:46

Yeah. I I I'm only I'm behind on my text.

Yeah. I I I'm only I'm behind on my text.

59:49

Alright. So we won't we won't keep you any longer. Alright. So so Breann Campbell, where should people find you? And they should go let's is is the podcast live yet? Can they go subscribe,

Alright. So we won't we won't keep you any longer. Alright. So so Breann Campbell, where should people find you? And they should go let's is is the podcast live yet? Can they go subscribe,

59:58

on the feed? Yeah. Subscribe to

on the feed? Yeah. Subscribe to

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