Brainstorming $10M+ business ideas with Jess Mah

Steal Jess' Billion-Dollar Startup Playbook [for free]: https://clickhubspot.com/jhm Episode 702: Shaan Puri ( https://x.com/ShaanVP ) boards the private jet of Jess Mah ( https://x.com/jessicamah ) to brainstorm business ideas and talk about her process for vetting which ideas to jump on. — Show Notes: (0:00) Buying a jet (5:37) Barn full of horses (8:44) Business ideas matrix (11:06) Idea: DOGE as a service (13:30) Idea: Vertical agents (16:52) Idea: Cargo ship coating (21:26) Idea: Holy Health (25:07) Building a team with digital twins (28:46) Jess’s 0 - 1 framework (31:09) Worst advice from Silicon Valley (35:44) Find a starving crowd (37:55) Idea: Divorce.fund (38:36) Failures: Credboost (46:08) Ignorant of past, realistic of present, delulu of the future (49:58) Engineering serendipity (56:12) AI for medicine — Links: • Mahway - https://mahway.com/ • YC’s Request for Startups - https://www.ycombinator.com/rfs — Check Out Shaan's Stuff: • Shaan's weekly email - https://www.shaanpuri.com • Visit https://www.somewhere.com/mfm to hire worldwide talent like Shaan and get $500 off for being an MFM listener. Hire developers, assistants, marketing pros, sales teams and more for 80% less than US equivalents. • Mercury - Need a bank for your company? Go check out Mercury (mercury.com). Shaan uses it for all of his companies! Mercury is a financial technology company, not an FDIC-insured bank. Banking services provided by Choice Financial Group, Column, N. A., and Evolve Bank & Trust, Members FDIC — Check Out Sam's Stuff: • Hampton - https://www.joinhampton.com/ • Ideation Bootcamp - https://www.ideationbootcamp.co/ • Copy That - https://copythat.com • Hampton Wealth Survey - https://joinhampton.com/wealth • Sam’s List - http://samslist.co/ My First Million is a HubSpot Original Podcast // Brought to you by HubSpot Media // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Shaan Puri?

  So you're not afraid to share ideas?

• 0:01Speaker 01

  Ah, no, I'm super afraid to share ideas. But that's, I mean, one of my ideas that I'm actively exploring and here I am sharing it with everyone here.

• 0:19Shaan Puri?

  We should, uh, address the elephant in the room. Why are we on, why are we on a plane? So, uh, we're just flexing on everybody now. This is my Ty Lopez. Hey guys, I'm just on my jet. Uh, so, so it's not that.

• 0:31Speaker 01

  Yeah, so this plane, um, it's a Cetacean CG3 Plus. And I fly planes for fun. So it's been my passion and my hobby. I think since even elementary school, I was obsessed with airplanes and, um, it was always my goal to be able to afford to fly one. And, and then I learned, I, I interviewed a bunch of very wealthy people and I said, how do you afford an airplane? Like, how successful do you have to be? And the secret was you don't have to be that successful. You just have to have a big tax bill and good cash flow. And so-

• 1:05Shaan Puri?

  Which takes success to get to that point, but-

• 1:07Speaker 01

  It takes some success, but-

• 1:09Shaan Puri?

  Less than you think.

• 1:09Speaker 01

  A lot less than you think, actually, um, because it's like a house. You could finance it, get, you know, put 20% down and then, you know, the, the rest is-

• 1:18Shaan Puri?

  We'll walk through that in a second. So the, the funny thing was we did an episode, a normal episode where we're on Zoom and it was great. Uh, you can go see it. It's called like Jessma, like high school dropout, you know, blah, blah. We, we, we YouTube'd it to make the title good. But like, you know, I don't know, 300, 400,000 people have, have listened to that interview across all the platforms. And I wanted to do a second one and you were like, hey, I'm in town. If you can kind of meet me here. I was like, all right, let's go. I'll meet you there. And the second thing is you're actually great with tax, tax hacks and you're better than my accountant who I pay. I pay this guy to be like, hey, come up with ideas that I can lower my tax bill legally, but how can I do it? What are the ideas? And he's a idea poor, you're very idea rich. And so I thought, okay, it's kind of fitting because one of the things we'll talk about at the end is your, uh,

• 2:01Shaan Puri?

  you've talked to a lot of rich people and tried to, to learn what are the options, what are the possibilities as far as taxes goes and that's, uh,

• 2:07Speaker 01

  Yeah.

• 2:07Shaan Puri?

  I want to learn that from you.

• 2:08Speaker 01

  Yeah. I mean, we'll talk about- That as relates to business ideas, but as relates to tax ideas, it's actually a pretty similar process. Like I'll just talk to as many people as possible. And I think the mistake people make with taxes is they have their one tax person. And that person worked with their parents and they've been loyal. But actually, this is a very bad place to have loyalty. It's really good to talk to, like, I've talked to dozens of tax-

• 2:33Shaan Puri?

  Promiscuous.

• 2:34Speaker 01

  You want to be very promiscuous here. I've talked to dozens of tax attorneys and tax accountants about their ideas. And I just keep track of all their ideas. And then I talked to all my friends, asked them for their tax ideas and consolidate it.

• 2:45Shaan Puri?

  That's so true. There's like this weird loyalty. It's like, yeah, he's been doing my taxes for four years. Like, yeah, but nothing has changed.

• 2:49Speaker 01

  Yeah.

• 2:50Shaan Puri?

  You want to get ideas from everybody. So let's do this plane real quick. So a plane like this, what does it cost roughly? What do you have to put down? And what is the tax savings or something? This is the mini tax lesson for this plane.

• 3:01Speaker 01

  Yeah, mini tax lesson. And then we go into more detail on this on the last episode I did with you guys. But this is a $12 million plus airplane. And you could put 20% down on the airplane. I got this pre-owned, so saved a few million bucks and it's just as good as new.

• 3:17Shaan Puri?

  So you put down roughly 2 million bucks?

• 3:19Speaker 01

  Uh, yeah, you put down about a few million bucks and then you just pay monthly financing on it. But then you get, uh, you get to write off up to the whole thing. Last year it was 60% upfront, but now with the new administration, it looks like accelerated depreciation is back. So if you bought a $12 million airplane, financed it, you can write off the whole $12 million off your tax bill, even though you only put in 3 million bucks. So you're gonna pay the government or you could buy an airplane. So it looks ridiculous.

• 3:47Shaan Puri?

  $3 million is going out of your bank account.

• 3:49Speaker 01

  Either way, the money's leaving your bank account. So like, it looks lavish. It looks ridiculous. But this is why rich people do these things.

• 3:57Shaan Puri?

  Right.

• 3:57Speaker 01

  And I just wanted to debunk that. A lot of people are scared to admit that. They don't want to share that because they want to flex more. They want to show off. But it's just a practical matter.

• 4:08Shaan Puri?

  Right. And you use it to like, literally be more efficient and go meet people where otherwise you might not have taken that day trip to go do it. Like you came up, you're like, I want to have lunch with you. And so you flew up, we had lunch and you flew out. And I was like, wow. First I felt honored, but secondly-

• 4:22Speaker 01

  Yeah.

• 4:23Shaan Puri?

  Man, there's probably a lot of people that I think I would have kind of amazing opportunities or build a relationship with, but I don't do it because the logistics are actually like in the way. Of course, this is not accessible to most people, but like if you're in that successful entrepreneur bucket, um, it kind of makes sense logistically as well.

• 4:38Speaker 01

  It does, yeah. And you know, we've got Starlink on board, so flying, uh, flying out here, I was able to make five phone calls and be on Zoom and you know, do FaceTime video where I'm like, yo, what's up?

• 4:48Shaan Puri?

  Right.

• 4:49Speaker 01

  And like, it's, it's a practical matter of saving money, but it looks really bad. If you're an operating CEO of a company, you're going to get chat on by your employees, your customers, your investors. And I realized that that would be a problem for me a few years ago. So that's why I stopped being an operating CEO, actually. It, it was really, I had this conflict of like, can I do everything I want to do? And I know it's the right thing to do.

• 5:16Shaan Puri?

  Yeah, I can fit the jet.

• 5:17Speaker 01

  I know I will, well, I know I'll create more abundance.

• 5:19Shaan Puri?

  Right.

• 5:19Speaker 01

  You know, I'll create more value for my companies. But at the same time, I know I'm going to get more flack. I'm going to have more people who want to rip on me, unfortunately. And I'm sure this video will not help with that at all, but like I defend it. It's like a practical matter.

• 5:32Shaan Puri?

  Right. I love that. Unapologetic. So.

• 5:34Speaker 01

  Yeah.

• 5:35Shaan Puri?

  Uh, enough about the private jet. It's cool. It's going to make for a great, great chat. First time for the podcast. What I want to talk to you about is what you're great at, which is ideas, um, and coming up with new ideas for businesses. So the track record here is you've been an operating CEO. You started this company called InTinero when you were really young, right? How, how old were you when you started that?

• 5:53Speaker 01

  I was 19 when I started. I knew absolutely nothing. Yeah. And then I built that company up and then started a bunch of other companies. Several of them are nine-figure valuation businesses. I have no unicorns under my belt, so that's a big insecurity of mine right now. I'm going to be super honest about it, like.

• 6:09Shaan Puri?

  That's interesting.

• 6:09Speaker 01

  I don't have a single unicorn, but if you add them all up, I've got, you know, multiple unicorns.

• 6:13Shaan Puri?

  Right.

• 6:13Speaker 01

  So that became my strategy. I decided I'm really not good at building unicorns, but I'm really good at coming up with smaller businesses.

• 6:21Shaan Puri?

  A barn full of horses.

• 6:22Speaker 01

  Yeah, a barn full of horses where I create more.

• 6:25Shaan Puri?

  I think we just coined something there, by the way.

• 6:27Speaker 01

  That was all you. Good work. Um, but yeah, if, if I could just raise less VC money for these companies and just create more of them and not be directly operating in them, then. That could add up to being just as valuable, if not more valuable than if I created one unicorn. Not to mention all my friends who are CEOs of unicorns.

• 6:47Shaan Puri?

  Miserable.

• 6:48Speaker 01

  So miserable and so stressed out. And also, they don't have the ability to live an amazing lifestyle because of all the stuff we talked about. They're scared of the optics. And they own a much smaller percentage of these businesses. Like, a lot of my unicorn CEO friends, they own like 5% of a billion dollar company, which is remarkable amount of money. That's a lot, but, you know.

• 7:11Shaan Puri?

  Yeah, totally. I'm in it for the lifestyle, not the, uh...

• 7:14Speaker 01

  You just have to decide what you're in it for. Just be honest about that.

• 7:16Shaan Puri?

  There's other people who are in it for the impact. That's dope. They, they should do that. They should save the world. I'm on the world. I'm glad that they're saving it.

• 7:22Speaker 01

  Yeah.

• 7:22Shaan Puri?

  I personally don't want to do that with my time. I want to indulge my curiosities, have fun conversations, and just enjoy my life with my kids. Like, that's kind of what I like to do. That's my, that's my gold standard.

• 7:32Speaker 01

  Yeah.

• 7:32Shaan Puri?

  So, your story is basically 19 years old, you start in D'Nero, you run that company, you grow that company. And then you, you, like you said, you transitioned from starting and running companies yourself to now you have this, like, your own hold co where you're, you're incubating or creating companies. And you said that in the last four years, you've started four companies, each worth over a hundred million dollars.

• 7:53Speaker 01

  I've co-founded companies. And when I say co-found, sometimes I didn't do a whole lot. Maybe I helped with idea, I got the early team on board, I got some early funding. And then, on some of them, I'm still really active. And on some of them, I'm not active. And I'm just like a significant shareholder.

• 8:09Shaan Puri?

  Right. All right, hey, real quick, if you're liking this episode with Jess, then we got something cool for you. So, when the episode ended, we asked her, we were like, hey, you were talking about how you have this, this playbook, this recruiting guide, you have this, like, content guide. You have these things. Would you mind sharing one of those with us? And she actually just sent us, like, all of them. So, uh, she wanted the listeners to be able to have them for free. So, they're in the show notes below. It's her talent playbook, it's her recruiting guide. I think it's an operations guide for how she runs her companies. These are straight from her. They're available in the show notes below. Check them out. I mean, somebody's giving you free gold. All you gotta do is take out your hands and just accept the gold. All right, back to this episode. I want to ask you about your idea process because that's amazing to be able to do that. I want to be able to do that. So let's talk about that. Let's talk about ideas.

• 8:54Shaan Puri?

  How do you get ideas to start these companies? And then what are some ideas right now that you're excited about?

• 8:59Speaker 01

  Yeah, let's talk about process first. So I love Y Combinator ideas, the request for startups. And when I was coming up with my first ideas for businesses like Indinero, that was inspired by that list. And it's a list of 100 business ideas where they say, if you build this, we are more likely to fund you.

• 9:20Shaan Puri?

  Right.

• 9:20Speaker 01

  And I really wanted to get into Y Combinator. And then I put together this spreadsheet. So I had this matrix of criteria. And one of my top criteria was complicated enough that other people won't copy me too fast. I think that's really important. If I'm a first time founder, I need to have more legroom. And then another criteria was I can pseudo bootstrapped this. Like I can raise some angel money, but I don't need to raise like $100 million. So like, I'm not going to build Tesla or SpaceX. I want to build something that $2 million could get me very far. My other criteria was I wanted recurring revenue. I wanted something that was sticky, like a must have.

• 10:05Speaker 01

  And so I literally went through every single one of those ideas on the Y Combinator list. And I rank ordered them based on these three criteria. And business accounting and tax management seemed to be the better one for my criteria. And so my process is I, you know, go online and I scrape these ideas. I've even gone to Reddit to look for ideas. I have one-on-one lunches and dinners with people like you. And I just say, hey, like, what are ideas you're exploring? And then we'll just have a brainstorm. But none of the ideas I've actually worked on. Came from me sitting in a room with a whiteboard and just like coming up with stuff.

• 10:43Shaan Puri?

  Yourself.

• 10:44Speaker 01

  Yeah, that's never worked out. I've tried it, by the way, with no success.

• 10:49Shaan Puri?

  Okay, so you you had this thing on your phone. You had like this idea database.

• 10:52Speaker 01

  Yeah.

• 10:53Shaan Puri?

  There's like three hundred ideas.

• 10:54Speaker 01

  Uh huh.

• 10:55Shaan Puri?

  And you promised, you said, I'll show some of them today.

• 10:57Speaker 01

  Yeah.

• 10:58Shaan Puri?

  Even though these are things you might still go do, I think.

• 11:00Speaker 01

  I might still do some of these.

• 11:01Shaan Puri?

  So do you want to give us a couple of them?

• 11:03Speaker 01

  Absolutely. It's called the Idea Hopper. So actually, let me pull it up on my phone.

• 11:07Shaan Puri?

  Okay, great.

• 11:08Speaker 01

  Should we start with the ones we talked about before?

• 11:10Shaan Puri?

  Yeah, she gave me a teaser of like two or three of them that I was like, don't tell me more, but yes.

• 11:15Speaker 01

  Like, should we start with the Doge as a service?

• 11:17Shaan Puri?

  Okay, yeah, I like this one.

• 11:18Speaker 01

  Yeah, it's very trendy right now.

• 11:20Shaan Puri?

  Doge as a service for companies. Explain.

• 11:23Speaker 01

  Yeah, I mean, most companies have so much waste. You have people who barely show up or they're phoning it in. And I have friends who say, oh, yeah, like, like I, you know, my husband quiet quit his job. He's like working two hours a day and no one's tracking it, so he's available to hang out. Those are the people you want to get rid of. So what if you could create a software platform that goes through and tracks who is actually on Slack, who is actually emailing, who is like using their computer? And if not, then they're fired. So Doge is a service for companies.

• 11:55Shaan Puri?

  And so it would be a team of consultants. It'd be a consultants plus AI. How would you do it?

• 12:00Speaker 01

  I think AI could do a lot of it. I also thought that if you're in enterprise, then it's you could sell this to consulting firms like McKinsey or BCG or whoever and say, hey, you guys can offer this to the CFO.

• 12:11Shaan Puri?

  Oh, they're already doing, they're already in there.

• 12:13Speaker 01

  They're already in there and that makes you seem more valuable as a consultant because you could say, hey, we could demonstrate that we'll save you hundreds of millions of dollars. You'll pay us only twenty million dollars. And this AI did all the work.

• 12:25Shaan Puri?

  Yeah, that's actually pretty interesting. I don't think enough tech teams build tools for the consultants who have already done the sale. Because what McKinsey is amazing at is they got this relationship with a Fortune one hundred company. They're on retainer, they're getting paid millions of dollars a year. And if you can sell them a tool that either helps them land and expand that contract or just save overhead in actually like executing that contract, that's going to be pretty valuable. Like if I was like building AI right now, I would not be trying to make something that like I'm going to not only build the tool, but also figure out all of the go to market. Maybe you could actually just sell this to consultants who already have the go to market done.

• 13:02Speaker 01

  Exactly, that. That's, I mean, one of my ideas that I'm actively exploring and here I am sharing it with everyone here.

• 13:10Shaan Puri?

  Hey, so you're not afraid to share ideas or what's your philosophy around that?

• 13:13Speaker 01

  Uh, no, I'm super afraid to share ideas, um, but

• 13:16Shaan Puri?

  Put you on the spot.

• 13:17Speaker 01

  You just got me really comfortable, so here I am. Um, this is an idea I've been playing around with for a few months and I really like it a lot.

• 13:23Shaan Puri?

  Okay, I like it.

• 13:24Speaker 01

  Um, I didn't want to be one of those people who said, okay, here are my shittiest ideas, now you go do them. Like, I think that'd be just really lame.

• 13:32Shaan Puri?

  Totally. Alright, what else you got? So, go as a service, that's one I like.

• 13:35Speaker 01

  So again, this is the trendy category.

• 13:37Shaan Puri?

  Okay.

• 13:37Speaker 01

  Okay, um, another idea is, uh, you know, everyone says SaaS is dead, agents are the new thing. Well, what if you could build vertical agent as a service for an industry? So, for example, build a library of agents for dental offices or for auto mechanics.

• 13:58Shaan Puri?

  Right.

• 13:58Speaker 01

  Or for, you know, clothing designers or manufacturers or whatever, or distributors. So, there are all these industries, but where they need their own very unique library of agents to automate their tasks. And you can go really deep there. So, this is more of a thematic business area, which will be, I think we're gonna see thousands of businesses doing this.

• 14:19Shaan Puri?

  Right. So, okay, so somebody's building a tool, and so you're saying you don't even have to build the agent. You're like, there's gonna be somebody who builds an agent that's about picking up a call, uh, and booking an appointment, let's say. Appointment, booking, agent. So, what you used to have to have pay a receptionist to do, now AI's pretty damn good, it's gonna be able to do that fully.

• 14:37Speaker 01

  Right. So, you have horizontal companies right now that sell the voice agent for any industry. The problem is, you start to do a lot of fine tuning and work for, if you're

• 14:47Shaan Puri?

  Dentist.

• 14:47Speaker 01

  A dentist.

• 14:48Shaan Puri?

  Right.

• 14:48Speaker 01

  So, what if you, you're a company and you look for all these off-the-shelf tools and make your own agents and plug them all in and tune it just for dentists?

• 14:57Shaan Puri?

  Right.

• 14:57Speaker 01

  And so, it's plug and play. I'm a dental office, I can use your company and it has like 100 different pieces of AI already baked into my workflow.

• 15:05Shaan Puri?

  Gotcha.

• 15:05Speaker 01

  That's the idea in a nutshell.

• 15:06Shaan Puri?

  Okay, I like that.

• 15:07Speaker 01

  And you should do this for an industry you know about. Like, if you're passionate about You know, dental offices, then do it in dental offices. Um, so that's uh.

• 15:15Shaan Puri?

  Shout out to anyone who's passionate about dental.

• 15:18Shaan Puri?

  You are, this was your day. You got it.

• 15:20Speaker 01

  I know, but the more.

• 15:20Shaan Puri?

  We recognize you.

• 15:21Speaker 01

  The more boring, the better. That's the Constellation Software model, right?

• 15:25Shaan Puri?

  Which, so we invested in this company that's uh, vertical SaaS, which was uh, called Shop Genie. They just, so we invested in it and I think within a year or two, they sold for mid eight figures. And what they did was they went to auto repair shops and they were like, hey, guess what? Auto repair shops need a CRM. So there was always CRMs like HubSpot and others that they work for any type of business. And he's like, well, but auto repair shops have specific things that are, you know, uh.

• 15:49Speaker 01

  Very specific.

• 15:49Shaan Puri?

  For them. So they built a tool that was just for them and then they went and they got like 3,000, 4,000 auto repair shops in like a year to use them. And by the way, I was.

• 15:57Speaker 01

  Very sexy business.

• 15:58Shaan Puri?

  Yeah. I was like, dude, how did you get so many shops to use you? And he's like, there's this guy who's like the auto repair influencer. He's like the Kardashian of auto repair shops and he vouched for us. And then all these people, uh, you know, followed on board. He's like, that guy makes like 20 million a year. As their like biggest influencer to other auto repair shop owners. It's like really insane.

• 16:16Speaker 01

  Oh, wow. Such a great business idea. Yeah.

• 16:19Shaan Puri?

  So, so what they did was they give them this tool. And it was like for booking your appointment and the text message follow ups or whatever. And what you're saying is like, and vertical SaaS has been a thing. Constellation Software did it. What you're saying is instead of vertical SaaS, it's going to be like.

• 16:33Speaker 01

  Vertical ass. Each one says a service.

• 16:36Shaan Puri?

  Vertical ass. I love it. All right. So.

• 16:38Speaker 01

  But seriously, and then the more like random, the better. Like if you could apply this to like, you know, marine shipping or to like resource mining. You know, then Constellation will be acquiring and ruling up these vertical ass companies in the next few years. Like that's, that's the future.

• 16:55Shaan Puri?

  What was the marine shipping cargo ship idea you were telling me about?

• 16:59Speaker 01

  Yeah, that was another idea I had on my idea hopper. The idea was in a nutshell, could we, uh, oh yeah, it was uh, coding for uh, these cargo ships.

• 17:09Shaan Puri?

  Coding like the paint coating.

• 17:10Speaker 01

  Uh, but to make it more efficient so that these ships could go even a few knots faster. Um, and that saves you a ton of money on fuel. And then you don't need to like take these ships out of the water as often to recode them. So this could be like millions, if not tens of millions of dollars over a decade for your entire fleet of cargo ships. Totally random idea. I got this from having dinner with someone who was playing around with this idea or looking at funding something like this. Like many years ago, another person just didn't have the money to proceed with it.

• 17:41Shaan Puri?

  Right.

• 17:41Speaker 01

  So my, I like, I learned about that just from having dinner with someone.

• 17:45Shaan Puri?

  Yeah, that's crazy. And so you, let's say you have an idea like that.

• 17:48Speaker 01

  Uh huh.

• 17:49Shaan Puri?

  Uh, so first is like where, who the heck even thinks about cargo ship coatings?

• 17:52Speaker 01

  Definitely not me. I mean, most of these ideas, the, the common theme is I didn't come up with any of these ideas.

• 17:57Shaan Puri?

  Right. So you're a good spotter, would you say? Or what, what are you good at?

• 18:00Speaker 01

  I'm good at initiating conversations with people who are likely to have ideas or have access to ideas. Like you have good access to ideas, so like.

• 18:09Shaan Puri?

  Actually, I've sent you an idea before, and now that I think about it, like, uh, my buddy James Courier has this great phrase. He goes, you want to turn yourself into an API. And what he means by that, he goes, you know, like a website has an API, which basically says, here's what I can offer you. I, I can give you location data. So you, you ping me, I give you location data. That's what I'm good at. And by the way, here's, here's what I want to get from your API, right? Here's the things I'm interested in. I'm interested in acquiring geospatial data. So you kind of have made your API like, hey, I'm always interested in hearing interesting, kind of weird, off the beaten path ideas. So when I hear one, I think, oh, Jess would like this.

• 18:43Speaker 01

  Yeah.

• 18:44Shaan Puri?

  So you've put yourself in my mind and associated yourself with, she likes to hear weird, cool, off the beaten path, you know, ideas that, that, you know, she, she's good at making them happen. And then in return, I, you know, you're like, what are, what are you good at? It's like, what do you offer as your API? It's like, I have a business and I'm trying to recruit a CEO. And I know you've done that a bunch of times. I'm like, oh, if I go to Jess, she's gonna, you know, reduce my error rate and make me go faster at this because she's really going to be helpful and do that. Or if I have another new idea, she's really good at flushing it out over a lunch, like riffing on it and then being like, super motivated to be like, all right, what are we gonna do to make this happen? Like, let's push the ball forward. So I think you've kind of done that in the idea space, which is powerful.

• 19:22Speaker 01

  That's really well articulated. Yeah. Like I get people calling me all the time saying, hey Jess, do you have like five minutes to chat? I have this random idea I want to get your thoughts on and would you build this with me? Or if I did it, would you fund it? I get those calls all the time, multiple times a week. And it's like, all right, like, yeah. I'll find time to call you back, but um it's like what Warren Buffett did. He just got the word out there. Hey, I'm buying businesses. Call me if you're ready to sell and it's a fast, easy process. I'm doing the same thing with ideas.

• 19:53Shaan Puri?

  Yeah, that's great. My business partner Ben, I was just thinking while you were talking like, his API is so funny is two things. One, Ben always knows a guy. So you're like, do you know anybody? He's like, I know a guy who knows a guy. That's always Ben's thing. Like, he always knows a guy who knows a guy. And the second thing is, a lot of people will go to Ben, they'll just text him when something good happens in their life. And I always am like, why did they, did you ask? He's like, no, no, they just told me. And like, we just closed this big deal, or we just did this thing, and they haven't announced it. And he's not that close to them. But what I realize is I do the same thing with him because he's somebody that makes you feel good when you win. You don't feel like there's any envy, or he's not gonna try to take anything from you. He's like genuinely pumped for you.

• 20:33Speaker 01

  That's awesome.

• 20:34Shaan Puri?

  And because of that, he just gets this wealth of inbound of people who are winning. Which is also great for us for investing, because we're like, oh, wow, these guys are doing really well. Do they need more capital? Do they need something? Like, maybe we could help them. And that's a superpower. So I think people, there's like these underrated superpowers. Like, the thing you're describing about, I'm good at, you know, maybe having interesting conversations, getting good ideas, and making people feel like they should come to me with interesting ideas. That's not even a skill you could learn in school, or nobody would even tell you that that's a thing.

• 21:01Speaker 01

  Yeah.

• 21:02Shaan Puri?

  But you're gonna build generational wealth off that.

• 21:04Speaker 01

  Yeah, that's well said. I think it's equally as important to know what we're bad at. You know, like, for me, I realized that I'm not the best operating CEO. Like, that's just not my forte. And after I realized that and came to peace with that, then I was able to say, okay, well, I'm gonna come up with ideas and recruit great teams and then empower them. And that's what I'm gonna figure out how to do Kudwari on and be great at. Exactly.

• 21:29Shaan Puri?

  So, um, let's see more. I want more ideas.

• 21:31Speaker 01

  Yeah, okay, so.

• 21:32Shaan Puri?

  You got me going.

• 21:33Speaker 01

  I have this other idea. The code name is Holy Hell. And I came up with this idea because I heard of another business that was minting like tens of millions of dollars in EBITDA within 36 months. And all they did was help one niche of a, like, medical provider get access to insurance. And then I did some research, I plugged this into GPT, and I realized there's so many of these other types of people, like chiropractors or physical therapists, where they can get insurance reimbursement, but they're so small, they don't have the The scale to negotiate with an insurance company on getting reimbursed. So they just charge all cash.

• 22:16Shaan Puri?

  Technically, they could. But is it that they don't have the time or the skill? Or like you need to band them together?

• 22:21Speaker 01

  Both. So if you band them together, then they can get some reimbursement and then you could create, you know, agents as a service to support them, to create more lock-in, and then you could help them with their customer acquisition. So it's got to be the full stack. And this other company did that for one of these different verticals. And I heard about that through a friend who heard about the company. And I'm like, oh, man, that's a great idea. Could I do something adjacent to that? That's not copying them, but similar in some ways.

• 22:48Shaan Puri?

  Similar blueprint, but in a different space that needs it.

• 22:50Speaker 01

  Exactly.

• 22:51Shaan Puri?

  So you would go, what would you do for that? So you would, uh, let's just walk through this. So I want to hear, so you have that idea.

• 22:56Speaker 01

  I heard about this. I got a clue because I was having lunch with a friend and he's like, these guys are making like 30 million in EBITDA. I'm like, all right.

• 23:04Shaan Puri?

  And what question are you asking that friend? Cause we were just talking before and I was like, how the hell do you get this? I go, what is your info diet? That you are getting these ideas that I don't get to hear about? You're doing something different. You know, you're not just consuming the same stuff I am because you're getting different ideas. So can we talk about that real quick? The info diet?

• 23:22Speaker 01

  Yeah, I mean, none of these come from reading a blog post or watching a podcast. All these are from in-person conversations. I think a lot of people are lazy. They just want to come up with stuff by staring at their computer. Nothing good comes out of doing that. If I'm being candid, you have to get out of the building. You have to like just talk to people.

• 23:42Shaan Puri?

  And when you're talking to them, what are you, what are you asking? Like, hey, what's interesting? What have you seen that's, that's cool?

• 23:46Speaker 01

  I say, yeah, what's the coolest? Uh, what's the most interesting exotic business idea that's minting cash that you've seen recently? And so I'm not asking them for a business idea. I'm asking them for what's an existing thing you've seen. It's like, why, what's the key to their success? And why does no one know about this?

• 24:03Shaan Puri?

  Right.

• 24:03Speaker 01

  And like, why hasn't anyone copied them yet? And, you know, why is now the right time for this?

• 24:11Shaan Puri?

  So you're filtering as they're, as they give you the exotic business that's minting cash. You're like, was there some spec, secret sauce that's not replicable? They, you know, maybe they're. Super influential in a community. Okay, that would take forever to build. Could this be done in another space? Is, does this take a hundred million dollars of venture capital?

• 24:26Speaker 01

  Yeah, how much do they start? And then they're like, oh yeah, like these guys just bootstrapped it.

• 24:29Shaan Puri?

  Right.

• 24:30Speaker 01

  Like, oh my gosh, now my math is really watering.

• 24:33Shaan Puri?

  Right.

• 24:33Speaker 01

  Like, okay, and what are the other risks here? Like, can AI just replace this in thirty six months? That's like the new risk factor in my like criteria that y'all have to ask them.

• 24:43Shaan Puri?

  So you get the clue. You get the clue from the conversation. Conversation, key question. And then you get the clue. Then you run it through your filter mentally, just there. Let's say now you're excited about the idea because you're like, um, holy health. And you give it a code name. Is there?

• 24:58Speaker 01

  Everything has to have a code name.

• 24:59Shaan Puri?

  Is, why is that? It makes it real?

• 25:01Speaker 01

  It makes it feel more psychologically real and like, okay, then I have something to remind me of the rest of the substance of the idea. And so I'll just like throw the idea into chat GPT.

• 25:11Shaan Puri?

  Before you even tell your coworkers, you're like, I think with AI first.

• 25:14Speaker 01

  Ah, yeah, exactly. I tell everyone before you tell me anything, think with AI as well.

• 25:18Shaan Puri?

  Yeah.

• 25:18Speaker 01

  And so everyone does that. And I say, give me like twenty ideas of potential names for this idea. And then I just pick one and this is the code name. And then we put it in the idea hopper and then.

• 25:27Shaan Puri?

  Did you see the CEO of Microsoft went on a podcast? I think Dorkesh's podcast, he had this great line. He goes, my new workflow is think with AI and then work with my coworkers. So he goes, I think people are thinking about like AI is going to replace your coworkers. Your, your employees are just going to, AI is going to do a task. He's like, but right now the best use case is me thinking and sparring with AI to get clarity. And then I go work with my coworkers after that. Sounds like you're kind of doing a similar thing.

• 25:53Speaker 01

  Yeah, we definitely do that. And what we're trying to do is, um, have all of our meetings be recorded. So even if it's in person, we're just like turning on granola and having, I have a big, one of those conference speakerphone things. And it's just recording everything and we're going to feed it in to create digital twins of all of us. Then have like basically. Thousands of versions of ourselves just brainstorming and sparring with each other.

• 26:17Shaan Puri?

  Oh my god.

• 26:17Speaker 01

  To refine ideas even further.

• 26:19Shaan Puri?

  It's like those little like chess arenas or whatever where they train the AIs to just compete with each other until like, until there's like a winner, a winning strategy.

• 26:25Speaker 01

  Yeah, and actually you're.

• 26:26Shaan Puri?

  How are you gonna do the digital twin thing?

• 26:27Speaker 01

  We're actually doing, we're actually training one based off of you as well. So I'm, we're gonna have it just watch every single video you've been part of. So it knows how to think like you, be like, hey, bring Sean into these conversations, bring Satya, bring Suck, bring Elon, bring like whoever. And I want all of them to like help battle test this, uh, you know, conversation.

• 26:50Shaan Puri?

  That's amazing.

• 26:51Speaker 01

  And so that way I don't need to pay for you.

• 26:52Shaan Puri?

  You know, that's useful when, if you just ask a question like, oh, what would Elon do in this situation? Or you know, take your most high agency badass friend who's not afraid and seems to have like clarity in the moment of a fog of war. If you just have that friend and you've hung out with them enough and you just literally just ask the question, it's like they're in the room. And I know if that works, then an AI that's actually trained on them is gonna be insane. Do you know how you'll do that? How will you create, like, what are you gonna use to make the me?

• 27:21Speaker 01

  Well, for me, there's so much public content for my team members. That's why I'm making sure that they record every single interaction in the company with each other. Um, and also.

• 27:30Shaan Puri?

  Is there a tool to do that? Or are you gonna make your own tool?

• 27:32Speaker 01

  It's just Trinola to, to get the transcripts. Cause once you have the transcripts, then you can just feed that into any of these, um.

• 27:38Shaan Puri?

  So any, any LLM will be able to like.

• 27:40Speaker 01

  It's gonna do a pretty good job. Yeah, we should go into more advanced conversation on this, but that's just like 90%.

• 27:46Shaan Puri?

  Do this so annoying. People are using my voice in ads all the time now. And I'm like, this is, this is wild. I'm like, how do I sue you? I don't even know who you are.

• 27:54Speaker 01

  Right.

• 27:54Shaan Puri?

  Second thing is that, um, but I'm going to, anybody who's doing, I'm suing you. I'm actively working on that. I'm telling AI to figure out.

• 28:01Speaker 01

  AI, I think AI will sue people for you. Yeah.

• 28:04Shaan Puri?

  But then also, also, um, what was the other one? Um, oh, writing style. So people will just put in chat, you'd be like, write this in the style, whatever. Cause I've written a lot of content publicly and it's, it's not, it's not me, but it's like, it's definitely kinda close to me. It's like, oh, that's 18 months away from being better than me. So that's definitely happening. You might as well embrace it. We're almost gonna need like a safe word. That's like, is it human Sean that I'm talking to? Or is this AI Sean that I'm talking to? Like, we need a code word.

• 28:31Speaker 01

  I know, but that it's like really exciting. And, um, and so yeah, Satya is.

• 28:36Shaan Puri?

  He's on point.

• 28:37Speaker 01

  He's on point here.

• 28:38Shaan Puri?

  Um, so where was I? So you were telling me about, uh, okay. So we're going through your process. So you get excited about the idea.

• 28:43Speaker 01

  Yeah, you have the clue.

• 28:45Shaan Puri?

  The code name and you then have a meeting with your team.

• 28:49Speaker 01

  Uh huh.

• 28:49Shaan Puri?

  What, what are you doing in that meeting? What, what are you trying to do to advance that idea forward?

• 28:53Speaker 01

  Yeah, every week we have a R and D team meeting is what we just call it. And we talk about the ideas that we're playing with. And the problem here with holy health, because this was a live idea and it still is a live idea. Everything I've shared today is still live, by the way. And, um, the problem is we just had too many of these ideas. I mean, you have hundreds of these ideas and we try to work on too many at the same time. And the problem is then you don't really advance any idea forward enough between each week meeting. And then we lose excitement.

• 29:27Shaan Puri?

  Right.

• 29:28Speaker 01

  So now the new rule is we're going, we're only going to have two and we're going to take them all the way until they're busted. Before you replace and bring in another one.

• 29:36Shaan Puri?

  And so like, what do you do? So you have the meeting, you pitch, you pitch the idea. Do you have a way of kind of pitching it to your team or what? How do you? Well, what's, what's happening in that meeting?

• 29:44Speaker 01

  In that meeting, anyone can pitch, so it's not just me. Um, everyone usually has different ideas and, um, and so, yeah, it's like, hey, here's a AI defensible idea. X, Y, Z. Here's why it's a Maui idea. So we kind of have a common understanding on what a Maui idea is.

• 30:01Shaan Puri?

  Which is roughly what?

• 30:03Speaker 01

  It's roughly an idea that can cash flow. That doesn't require a lot of outside funding. We could fund it ourselves. Um, and where it's like boring and complicated enough where random people are not going to copy us that easily. Or reverse engineer that easily. Um, that, those are Maui ideas and that's what I encourage anyone else to do as well.

• 30:24Shaan Puri?

  Okay.

• 30:24Speaker 01

  Like if you're an auto mechanic expert, then that might be your theme of idea. And we have that for like financial services in particular.

• 30:31Shaan Puri?

  Right. And so you, um, what hap, what do you, where do you leave that meeting? You say, all right, what are we going to do next?

• 30:38Speaker 01

  We say, okay, what are we going to get done to advance this between this week and next week? And we just get very specific and it's like, all right, like person A, you're doing these five things, person B, you're doing these five things. And the next step might be like, okay, let's just go call, like for Holy Health, the next step was let's just call some chiropractors and ask them if they, you know, figure out who accepts insurance and who doesn't and why. And then ask them, why don't they plug into these existing companies that should be that doing something similar? So a lot of it's just like, what are the questions we're curious about?

• 31:12Shaan Puri?

  And psychologically, are you trying to disqualify an idea or are you trying to qualify an idea? Like, what's the mindset? Is it, I'm trying to figure out, is this good or bad? Or is it like, I'm listing the riskiest assumption, I'm doing it? What are you trying to do during that, those next few weeks?

• 31:27Speaker 01

  It's, uh, it's, it's not, we're trying to figure it out or, or disqualify it for say, I think either attitude might be too extreme. It's more like, there might be a creative angle here that no one else has thought through. And so we're not married to this idea. We're holding it very loosely. We just have to figure out like, okay, you might hear an interesting insight from a chiropractor that says, hey, your idea is okay, but what would make it really good is if you also added in all these AI agents to automate away my receptionist and, and then, you know, my customer acquisition is terrible because X, Y, Z. Like, those are the insights we're looking for to then manufacture an upgraded version of the idea. So we assume the first idea is terrible and it's going to go through like 10 pivots.

• 32:08Shaan Puri?

  Right.

• 32:09Speaker 01

  Like,

• 32:09Shaan Puri?

  Which is very useful because that's almost always the case. And if you don't have that attitude, you basically, you hear something really juicy, but you're so locked in. It's like somebody was handing you gold, but you were out there just, you know, searching for bronze. And it's like, are you sure? You sure you want that? I was gonna ask you, you know, you, you're talking a lot about ideas. In Silicon Valley, there's this idea, there's this phrase, which is, you know, ideas are worthless, execution is everything. Do you buy that?

• 32:39Speaker 01

  I think it's BS. I think it's, I think it's some of the worst advice I've ever heard in Silicon Valley.

• 32:45Shaan Puri?

  So what's your take?

• 32:46Speaker 01

  My take is that ideas are really fricking important. And if you have the wrong idea, you'd be a great team and you're screwed. And actually, I modified my thinking on this because I was a scout for Sequoia Capital for many years. And they would show us a bunch of these like great ideas with amazing traction, especially in consumer internet. And then they would ask us, would you invest on this memo, yes or no? And so we would vote and then they'd say, well, here's what happened to that company. It ended up being, you know, a zero, even though it had the best team. The idea was still garbage, so it ended up being a zero. And that was like a common theme I noticed.

• 33:25Shaan Puri?

  So they would train, almost train you on historical memos, basically?

• 33:28Speaker 01

  Yeah.

• 33:29Shaan Puri?

  Oh, wow, that's interesting. But if the traction was great, is it usually the traction or just the team and the thesis was great?

• 33:37Speaker 01

  I mean, the early traction might have been good and the team looks good. But then if you really think through the long term, like, is this idea sticky? After a year or two, will there be copycats? Like, is it like, is there anything that really holds the consumer in? You know, that's where these ideas would then lose steam.

• 33:54Shaan Puri?

  Right.

• 33:54Speaker 01

  And die. And so that kind of helped me think about this a bit differently.

• 34:00Shaan Puri?

  And so you're saying ideas are super important?

• 34:02Speaker 01

  Ideas are really important and the team is really important. They're both really important, but to say, oh, yeah, like ideas are a dime a dozen. Like, really, it's not just the idea. It's like the whole thinking of the business, like doing the calls to like, understand or meeting with the chiropractors in person or the auto mechanic and really figuring out these juicy tidbits that you're not going to find out by sending out a stupid survey or by using chat GPT to tell me, hey, what are the problems that chiropractors have? Like, that helps you build an interview script for what you're going to then talk to them about. But then, you know, you have to show up. So like when I was building Inanero, I would go to Yelp and I would call these CPAs. And I would say, hey, I'm like a 19 year old college kid. I know nothing about business.

• 34:46Speaker 01

  I want to do something to help accountants. Could I come to you, buy you lunch and just like ask you some questions just for 15 minutes? And then you show up, they're not going to kick you out after 15 minutes. 15 minutes is going to turn into two hours and you have your notepad, you're scribbling. Like, they love that. They want to be helpful.

• 35:02Shaan Puri?

  Right.

• 35:02Speaker 01

  And I did a lot of that personally. Like, I just showed up and asked them my questions and then got all these insights. And we still do that. I'm still on these calls. Okay, like, even if it's not in person, if you could at least do like hour long plus, you know, expert calls, like we use GLG for this. There's also like Alpha sites and they charge you a lot. You know, you might be paying 800 bucks or a thousand dollars to talk to an expert in a very difficult to find area. Versus like accountants and chiropractors, like you could just call someone on the internet. But if you want to find like an expert in titanium mining, how are you going to find that person? You go to GLG and you pay them a thousand bucks, they'll find the person for you, set up the phone call for you. And we do that all the time.

• 35:48Shaan Puri?

  The way you're talking about ideas and markets, it reminds me of, there's a story of this marketer. And the marketer goes to, I think, a seminar or something like that, there's other marketers there and he goes, "Okay, um, we are gonna, let's pretend we're opening up a hot dog stand." And he's like, "So, I can get," he's like, "I'm a genie, I will give you anything you want to make your hot dog stand the most successful you can make it." So he goes, "What do you want?" And so first person, "What do you want?" The guy's like, "Uh, I want the best ingredients, best buns." He's like, "Got it, best buns." "You, what do you want?" He's like, "No, no, no, buns, that's foolish." "In the food business, location is everything." So location, "All right, I got you this corner spot in a high-traffic area." "Cool, uh, location, you got it, what do you want?" And each person had like your best branding, best whatever.

• 36:33Shaan Puri?

  And he goes, "Um, I have one thing that I think will beat all of you if we all, if we all did the same thing and that we all got our wish granted." He goes, "All I want is a starving crowd." And, um, if you're a marketer, like, you're gonna spend a lot of time and energy trying to sell something, the absolute best decision you can make upfront is finding a starving ravenous crowd. And it sounds like, you know, when you say ideas, really the idea, you know, what's underneath an idea is a customer or a set of customers who have like a real pain and like a desire to solve that pain, you know, like they are, they are hungry. And they're hungry for something and if you just show up with even decent buns and hot dogs, like, they'll buy it, you know, instantaneously. It's okay if it's a little cold, it doesn't matter.

• 37:15Speaker 01

  Yeah, that's a great story. It's, uh, it's about like, how cute is this problem? And ideally, um, one hallmark of a Maui idea is the customer doesn't have to pay anything. So in holy health, You don't pay to be on our platform. By being part of our platform, you make more money. You get more customers and we'll take a cut of that in exchange for helping you grow your business.

• 37:39Shaan Puri?

  So you like that model because there's no friction.

• 37:41Speaker 01

  I love that model. It's like, why would you say no to that? It's like you're just saying no to more business.

• 37:46Shaan Puri?

  Yeah, that's like those companies that um they'll negotiate with all vendors on your behalf and like whatever we save, we'll take 20%. You're saving nothing today. If I save you any money, I'll take 20%. And it's like, okay, go have at it. You, you were talking about, you had a couple of other ideas. You had like a divorce one. What was that one?

• 38:02Speaker 01

  Oh yeah, that is like um I had so many friends getting divorced and still do. And people say they need an advance on their alimony or like there's gonna be uh or their money gets tied up and locked up because they're in divorce proceedings and they're really rich. They're really successful, but they can't tap any of their own capital while it's all tied up. So what if you could just give them some of their money back and so that was just like a funny random.

• 38:24Shaan Puri?

  Like a creative financing around either the window of a divorce or the alimony.

• 38:29Speaker 01

  We called it divorce dot fund.

• 38:32Shaan Puri?

  Didn't go forward with that one?

• 38:33Speaker 01

  No, I mean, people talk about it and we still joke about it, but there are other ideas that we got more excited about, so.

• 38:40Shaan Puri?

  So let's talk about failures because one of the things you said to me before this.

• 38:42Speaker 01

  So many failures.

• 38:43Shaan Puri?

  You were like, I like your podcast, but you know, sometimes you listen to people and it just sounds like it's, I had this idea, it worked, I'm so great, you know, like that's a podcast problem. And you were like, I want to be super honest about things we're trying that are not working or failures I've had. Where do you want to start?

• 39:00Speaker 01

  Yeah, I mean, I would start by saying when I use YouTube and I have all these entrepreneur business podcasts, I spend a lot of time flipping through and I think, man, like I'm not doing enough, like I'm not good enough. Even when like I watch your podcast, I think that. And I think that a lot of people, you know, probably share that view. And, and, and the people you interview, I know a lot of these people, these are my friends. I know what they're secretly struggling with.

• 39:28Shaan Puri?

  Yeah.

• 39:28Speaker 01

  And they're not necessarily sharing all of that. And I think that's just important to know. So in my case, it looks like I am good at coming up with these things and having success, but most of the time, they're total duds. And one example is we had this idea, we called it cred boost. Terrible idea in hindsight. I'm so embarrassed to share this, but I'm going to share it anyway. And the idea was. Um, we're going to help you like improve your credit and repair it and you know, we had the customer acquisition funnel going and it was high churn, low price point, very high regulation by the FTC, you know, it, it, it got compared to credit repair businesses too much and you know, my idea was we're going to boost your credit, not repair, just repair

• 40:11Speaker 01

  your credit and it could have made some money, but we just got bored with that. And so I burned a few hundred thousand bucks experimenting with that and then I put in the wrong team. So I made so many mistakes on that. That was an early incubation that went nowhere. And this other idea was we're, we're going to help veterans of the US military, um, find new jobs and we're going to get paid by Vet Tech and the GI Bill to do that. And we could do this all online. So it's virtual, it's scalable and we're helping veterans. So it felt like it was a really good idea. Yeah. And the veteran, all they have to do is say yes. So we launched all these ads, all these veterans signed up. They're like, hell yeah, I could double my salary, make more money and do this all online from the comfort of

• 40:56Speaker 01

  my home. And, um, and our payment mechanism was this thing called Vet Tech, V E T T E C. And it had bipartisan, you know, acceptance. Everyone loved it, but it's got stuck. It got approved by the House and never went up to the Senate and the money dried up and we were like, all right, we'll get renewed imminently. And 18 months after that, still not renewed today, still not renewed. And we're like, okay, well, the hep business died just because of that. And then I tried to pivot it. I'm like, oh, can I get the GI Bill to pay for it? But then the GI Bill requires in person and then after that we lost interest. Like I was the only one excited about this. Still like, guys, we've got to help the veterans. My team's like, we have other ideas that will make more money, Jess,

• 41:40Speaker 01

  and we want to make money. Like, all right, I'll come back to this when the time's right.

• 41:44Shaan Puri?

  So swings and misses for sure. I want to show you this. Uh, I want you to read this. This is from a talk you gave.

• 41:50Speaker 01

  Oh man, 2011.

• 41:52Shaan Puri?

  This is when it hurts, but not just because an idea is wrong. Sometimes it's even when the idea is right and you're running a company. Can you, can you read this?

• 42:00Speaker 01

  Yeah. I wrote this to my mom and my dad on Saturday, June 4th, 2011 at 5:56 a.m. So I was up all night. I couldn't go to sleep. I was so upset.

• 42:11Shaan Puri?

  Subject line.

• 42:12Speaker 01

  Kind of sad. I feel like I'm Bernie Madoff, reached on the outside but completely broken on the inside. There's just a lot of pressure right now because the company is running dry on money in the next nine months, nine or so months. And we really need to produce this summer or else we're royally screwed. This was about a year after Y Combinator for me. Anyway, I want to start seeing a therapist or something because this is just no way to live. I have no idea how you handle this entrepreneur job, Jess. And my mom, she's an entrepreneur. She came here.

• 42:45Shaan Puri?

  Do you remember sending that?

• 42:46Speaker 01

  I do. I absolutely remember that. I remember the night. I remember how I was just like very upset because I had all these hoops and expectations on myself. And, you know, Paul Graham even, he was my mentor. And he's like, you're going to be one of the greatest entrepreneurs of all time. You, Patrick Hollison and Sam Altman. And I'm still the least successful today. And I still think about that often. And.

• 43:11Shaan Puri?

  That weight was on your shoulders.

• 43:13Speaker 01

  That weight was fully on my shoulders. It still is on my shoulders. And, um, and my mom called me and she said, hey, like, I love you no matter what, even if you're a total business failure, I'll still love you. And then I just cut all my expenses, cut my burn, moved into a tiny apartment with my business partner and, and then just slowly crawled out, out of the hole. And then, yeah, we grew in and out to, you know, it's a few hundred employees, profitable, good business, not a unicorn. But it gave me all the training and spiritual training.

• 43:45Shaan Puri?

  Right.

• 43:45Speaker 01

  To pursue entrepreneurship and be comfortable with mistakes and failure.

• 43:50Shaan Puri?

  Were you, uh, at that time? I guess like, what was the conversation with yourself to like? Because you're like, I did these things. I lowered my burn. I did this, I did this. So those are the actions. But before the action comes, some, there's some inner monologue. There's some conversation you got to have with yourself. And I, I love the inner monologue because. Your whole life gets dictated by this tiny little voice in your head that nobody hears. It's the one telling you how to feel, what to do, where to stand, what to say. And I think training that and learning how to like, kind of uh, improve that inner monologue is so important. And you, it gets better in moments like this, right? That's when it gets, that's the muscle building for that, that inner monologue. Do you, do you remember kind of what you were telling yourself at that phase?

• 44:33Shaan Puri?

  You, you wrote this, your mom tells you something, what'd you tell yourself?

• 44:36Speaker 01

  I distinctly remember what the monologue was that whole evening, which is, I am destined for greatness and I am not producing my best work right now. I am not showing up at my best, I'm not playing to win. And I'm, I'm falling behind and I need to diagnose what went wrong and I need to keep on trying and I will not accept or tolerate failure. That was, was going through my head.

• 44:58Shaan Puri?

  Were you listening to a song at that time? Where'd that come from? That was fire.

• 45:01Speaker 01

  No.

• 45:02Shaan Puri?

  How'd you get yourself into that state? From kind of sad to like, kind of kick ass?

• 45:06Speaker 01

  No, that was sad though. That was not, it was not an empowered attitude. I was, I was thinking that and, but because I knew that that was my situation, then it went from like, all right, like I need to do all this or I'm screwed. And then like, all right, I'm really sad and I gotta process my emotions.

• 45:23Shaan Puri?

  Right.

• 45:24Speaker 01

  Just get it out of me and, you know, be honest with myself that I'm struggling. I need to ask for help and I didn't have a great community. Cause back at that time, you, you know, as an entrepreneur, you want to show off, you want to posture, you want to seem like you're better than everyone else. And then after that, I realized I could just be honest and also have friends. And I told all my girlfriends and ends up more people were struggling than I realized. More of my Y Combinator batchmates were also running out of money. And if we look back today, most of the companies from that batch did not make it. Most of them went BK and then people took normal jobs or started new companies and then eventually found success.

• 46:04Speaker 01

  And so, yeah, I still think about that. I still have thoughts like that today. It's not, it's a work in progress.

• 46:10Shaan Puri?

  Right. You know, I've, I've done whatever 600 of these episodes and at certain point, you know, you'd have to be sort of stupid to not realize like there's a mindset amongst the common mindset that I think great entrepreneurs have, and I've distilled it down into this. I think a great entrepreneur's mindset is they're ignorant of the past because it's already done. If they live there, they'll die there. If you just stay stuck on, well, I've been failing for five years. Then you will feel like a failure and you won't be able to win. So you're ignorant of the past. Realistic about the present, which is kind of what you said, like, I'm not showing up at my best. I'm not putting in all the effort. I'm not doing the obvious things that I should be doing right now.

• 46:51Shaan Puri?

  But I'm also not, it's not over. And so if they don't make it worse than it is, they don't make it better than it is. I see it as it actually is. So ignorant of the past, realistic about the present and delusional about the future. You have to have that delusion because if you're just realistic and practical about the future, you don't do anything great.

• 47:05Speaker 01

  Yeah, that's really well articulated. I think also going through moments like that. I remember then talking to my business partner and we did a full postmortem. We listed out every single strategic and tactical mistake and thing we did wrong. And what we would do different if we went back in time. And I wish I wrote this somewhere because it was a long list. I mean, it's like I would do everything different if I could go back in time was the attitude. And even today, I was talking to, or yesterday I was talking to one of my colleagues. And the number of bad ideas we funded and experimented with.

• 47:47Speaker 01

  And our process flaws, you know, we, we would also do everything different going three years back if we could. But we're talking about this constantly and that goes back to what we talked about at first, quote, worry. So every week. What if we bake this into our workflow? No matter how good things are, let's still reflect on all the mistakes we made so that we can improve and not repeat that again. It doesn't have to be when times are tough and when you're about to run out of money that you're reflecting on, like, everything.

• 48:15Shaan Puri?

  Yeah, yeah. No old mistakes. It's kind of like, it's the no new friends. It's the no old mistakes is what you want. You don't want to keep making those same mistakes again. You said something when you were talking about like, I'm not, you said, I'm not showing up the way you do. You said, I'm not playing to win.

• 48:27Speaker 01

  Yeah.

• 48:27Shaan Puri?

  That's something, while I was talking to your boyfriend before this, and he goes, I asked him, I said, what's a, what's a Jess-ism? Meaning like, if you talk to people enough, you sort of see their, the things they repeat, the things that are like their philosophy that they're like actually operating on. And he go, he said something like, um, play to win, don't play not to lose. Explain that.

• 48:46Speaker 01

  I think that came from this story that I just shared where I, one of my problems was I was playing not to lose, so I was in a scarcity mindset. And when I'm running out of money and I'm in scarcity mindset, um, I mean, there's research that talks about how your IQ drops by a lot during those periods. And so I'm not gonna think outside of the box. And, um, playing to win means I'm optimistic, I'm delusional about the future of it, right? So I, I see a lot of my friends who are just like playing it too safe. They're not, they're not trying new things. Um, and so you can't do the same thing you've been doing and expect a completely different outcome.

• 49:27Shaan Puri?

  Right. Well, it's an example, maybe non-business related, where in your life, you're playing to, you had the moment where you're like, ah, I need to play to win here instead of play not to lose.

• 49:36Speaker 01

  In my personal life, like, uh, for example, with the airplane, you know, this is a physical manifestation of that attitude.

• 49:42Shaan Puri?

  Hmm.

• 49:43Speaker 01

  And why it's really fun to share that with everyone today. Um, it's easy to say, I'm gonna be frugal, I'm gonna save the money, I'm gonna let it compound, I'm gonna invest it in my other businesses. Or, you know, screw it, I'm playing to win here. This is gonna manifest way more abundance for me than if I don't.

• 50:02Shaan Puri?

  You had told me something when we were at lunch that inspired me. You met somebody, I think, who threw a great event and you hired this person. You were like, hey, here's a budget and I will pay you whatever you're making at your job. I'll pay you that or more, whatever. You're like, I want to have four events a year in these four cities with the most like inspiring, fun people in my like that I want to create. I'm going to engineer some serendipity, some luck, some fun, some cross pollination of people and ideas four times a year in these in these places. And I remember I've told probably five people this because you need some resources to do it. Yes, of course, of course, like, don't, if you're in the YouTube comments, don't be that guy who's like, oh, it must be nice to have money. Great. There's a version of this in your life, too. You can take people out to dinner, right?

• 50:46Shaan Puri?

  It doesn't have to be a grand event. But I was like, that is an investment that I don't even have a line item for.

• 50:53Speaker 01

  Yeah.

• 50:53Shaan Puri?

  Right? I kind of know if I did it, probably really good, I would A, have a lot of fun and B, like, yeah, I do think good things would happen. But you took almost like intentional business capital allocation approach to the like luck and fun part of your life, which I think most people leave untouched. Luck and fun is just something that either happens or doesn't happen. It's not, I don't use my business brain for that. I use this other part of my brain. It seemed like you almost used your that same brain for both.

• 51:18Speaker 01

  Yeah, because I wanted to kill two birds with one stone or three birds with one stone because I want to have fun. I want to do more business, meet cool people. But I also had this friend who hated her private equity job and really wanted an excuse to leave. And so I was able to present that to her. The vision was four events a year with, you know, the most successful entrepreneurs and investors I know. And we're launching the first one literally today. That's exactly what I'm flying off to after we're done. And then the vision is we'll do a summer thing, a fall thing, et cetera. But it was really expensive. And so what she and I decided to do was we would help her find other work. Other events, so I'd set her up with my other friends throwing events.

• 51:59Shaan Puri?

  Right.

• 52:00Speaker 01

  She would charge per event and she would get paid based on the revenue coming in to the events. So it's all variable versus her being on my payroll.

• 52:09Shaan Puri?

  Right.

• 52:10Speaker 01

  And so for this event, what I did is I called a bunch of my friends. I said, hey, you gotta pay something because I have hard costs here and they paid in and then she only paid herself after there was a profit. So you could get creative about this. For the ideas, we were talking about earlier and my whole team, a bunch of these people are on contract. I found them on Upwork.

• 52:28Shaan Puri?

  Yeah.

• 52:29Speaker 01

  Okay, like you could do this.

• 52:31Shaan Puri?

  What type of person, like what skill set do they have that you found out? You said like Fiverr or Upwork?

• 52:35Speaker 01

  Yeah, like one's a product management UI UX thinker. One is a financial services guy. One was an intern of mine. He was at UCLA and he asked me to speak to his entrepreneur club. And then he said, hey, could I like take you to lunch? I want to get some advice from you. What should I do after college? I'm like, just intern for me and I'll teach you the ropes. And then he was so good that now he's full time with us. But he's probably one of my best idea sparring partners. And then here, this event planning person, I met her from the Burning Man community. These people are everywhere around you. They don't necessarily have a fancy, specific resume and they're fun. I love them. We work well

• 53:20Speaker 01

  together. That's more important than the resume.

• 53:23Shaan Puri?

  Right. I met a friend recently who told me this. He said something in passing. He goes, I was at this event and then there was this guy who was, he was dressed differently, blah, blah. And me and my friend, we collect eccentric people. So we went over to him and had a chat. I kind of paused him. I was like, that's kind of a cool thing you just said, like, I collect eccentric people. I don't do that. And I was like, but what do I collect? Like if I just put myself in there, if I said, what am I a collector of? So like for me, I'm a collector of what I call golden nuggets. It's like, I can have this conversation with you and I'm just looking for two, three, four things. Like I don't need. Two hours or 90 minutes of a conversation to be perfect. I need three ideas that spark something, three golden nuggets that will change my way of thinking or acting. Uh, so I'm a great collector of those. I'm also a collector of like young talent.

• 54:07Shaan Puri?

  Like I see somebody who's young, who's hustling or is talented in some way. I will like, kind of really help them out because I want to A, stay young myself and be helpful. But B, I kind of want to be able to connect dots between young people and good opportunities or young people and funding or whatever it is. Uh, and so I think there's this interesting idea of like figuring out what is it that you collect? Like some dudes collect stamps, some dudes collect bugs. What is it that you collect? So like for you, what do you, what would you say you collect?

• 54:34Speaker 01

  I would say I collect interesting people with outside of the box ideas who also like to have fun. That is the key intersection I'm looking for.

• 54:42Shaan Puri?

  That's your Venn diagram.

• 54:43Speaker 01

  Exactly. Cause I think you could find interesting people where they're not fun. It's very transactional. They're just in it to make money themselves. But then the problem with that is then I can't do any business with them. So that's. So then my idea was, okay, how do I bring more of these people together so that we can have more serendipity? Oh, I'll just create my own event and then bring them there and then have a bunch of my people also, you know, talking to them, getting their ideas and seeing where we could partner on stuff.

• 55:08Shaan Puri?

  Right, right. Engineering the serendipity. Our buddy Nick Gray does a like no cost, low cost version of this. So he used to do a renegade museum tour. So he like, he loved museums. So his Venn diagram was like fun people who are interested in like, you know, going to a museum on a Friday night. And he would host his, he wasn't a part of the museum. He would just take people on a tour because he knew the museum better than the tour guides. And he would take them on a fun version of the tour. They'd like have a drink outside after, uh, beforehand. They would go in and they would like do little fun things at the different stations. So like that was one thing he did. Another way he engineered serendipity is he would throw these like singles events. Where he himself was looking to date somebody, but he's like, well, I could just kind of do that. I can swipe left or right. Or like, is there something I could do more creative?

• 55:51Shaan Puri?

  That will not only help me find someone amazing, but maybe even like a bunch of our friends find somebody amazing. And he started hosting these singles events. And again, the, it's a pizza budget. It's not like it's super fancy.

• 56:01Speaker 01

  It doesn't have to be fancy.

• 56:02Shaan Puri?

  Doesn't have to be fancy, right? Uh, and I feel like I need to say that because we're sitting on this like jet, but like.

• 56:06Speaker 01

  I mean, most of the stuff we do is like very cheap, cost effective and peace for itself and sometimes makes a profit, you know?

• 56:11Shaan Puri?

  So like, but just taking that intensity to engineering some serendipity. I kind of love that. Uh, before we leave, what do you, just leave me with what are you currently nerding out about?

• 56:19Speaker 01

  Um, I've been spending a lot of time thinking about like cancer and oncology. I've been thinking a lot about longevity and you know, we're still funding a lot of the research with Mike Levin, who's my favorite scientist of all time. He's the bioelectricity ninja. And I've been nerding out on this a bit more because I was mentioning to you before we got here, I've been in a bit of a sad mood this week. I had a friend die of cancer a few days ago. Never smoked a cigarette in her life and had stage four lung cancer. And, um, and it's just more examples of this in my life. Every year or two, I lose a friend like that.

• 57:01Speaker 01

  And, and so it's not necessarily going to make money. It's not gonna improve my lifestyle, but I'm just like, I got to nerd out on it.

• 57:09Shaan Puri?

  Right. Is there exciting progress in the cancer oncology stuff right now? Like, is there something, is there a new paradigm or a new pathway that's interesting?

• 57:18Speaker 01

  Yeah, like with Mike, we, he talks about how he's been able to use bioelectricity to normalize cancer cells. So everyone right now in the field is talking about how do you kill cancer, right? You think about chemo, radiation, it's really painful on the patient, but if you could just normalize cancer and not have to kill it, that's gonna be a lot more comfortable.

• 57:40Shaan Puri?

  Kind of makes it like a normal, non-cancerous cell, basically?

• 57:42Speaker 01

  It's still gonna be cancer, but it's more benign, essentially. So that's really cool research. He's got a lot of great stuff on longevity, making lab, uh, animals live longer. Um, I don't think he wants me to talk about it publicly yet, but...

• 57:56Shaan Puri?

  How insane is the AI, uh, AI for medicine and biology? How is insane is that gonna be?

• 58:03Speaker 01

  I think it's gonna be amazing. I think it's also gonna be a lot harder than people think. Cause you have AI that's coming up with all these ideas, but the bottleneck is still regulatory, still FDA, it's still getting a clinical trial put together.

• 58:17Speaker 01

  That's one area where we're gonna see slower progress than everyone is bragging about. Whereas, you know, with everything else we discussed with digital twins, if we could have the two of us brainstorm ideas, there's no bottleneck there.

• 58:27Shaan Puri?

  Right, right, right.

• 58:28Speaker 01

  Like, the only bottleneck is like spitting up the computer and then us pulling the trigger to fund ads or fund whatever. But in health and bio, it's people's lives are at stake. It's gonna go slow still, I think, unfortunately.

• 58:41Shaan Puri?

  Okay, well, where should people find you and what should they send you?

• 58:45Speaker 01

  Yeah, um, if you have any exotic, outside-of-the-box business ideas you wanna run by me and, um, I'd love to discuss that with you, uh, shoot me a note. And I am on LinkedIn. LinkedIn, um, just search Jess Ma. And, um, I've posted on my blog there almost every week, uh, partially using ChatGPT to come up with my blog posts. But I still review it. I'm like, hey, write me a blog post that's 2950 characters long, cause the LinkedIn limit's 3,000. In my voice about X, Y, C, X, Y, C and insert these anecdotal stories. And, uh, and then like within two minutes, I have a blog post.

• 59:25Shaan Puri?

  That's amazing.

• 59:25Speaker 01

  Yeah. But so I post there and these are real life stories in my life. And, uh, just send me a message on LinkedIn. Would love to hear from people. And also the last pod we did, I made a bunch of friends.

• 59:37Shaan Puri?

  Oh, great.

• 59:37Speaker 01

  Like, people just cold emailed me and I'm like, yeah, I'll grab lunch with you. I'll grab dinner with you. And two people I met from the pod are coming to my retreat.

• 59:46Shaan Puri?

  That's a, that's amazing to hear. That's a, a point of pride for us is like, we want it today. If somebody comes on the podcast, they, you should get more kind of inbound messages from this than any other podcast you go on. And the second would be that the people who message you are people you would actually wanna talk to.

• 1:00:01Speaker 01

  Yeah.

• 1:00:01Shaan Puri?

  That would be the goal, right? That if we're doing that, we've kind of built the right tribe here, so.

• 1:00:05Speaker 01

  Yeah, you've done a great job with that. Real community, so thanks for having me here.

• 1:00:09Shaan Puri?

  Well, cheers.

• 1:00:10Speaker 01

  Cheers.

• 1:00:11Shaan Puri?

  All right, here we go.