Asking A Billionaire How To Make $1,000,000

Shaan Puri

"So you're not afraid to share ideas?"

Jess Mah

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

Shaan Puri

**We should address the elephant in the room:** why are we on—why are we on a plane? So we're just flexing on everybody now. This is my Tai Lopez: "Hey guys, I'm just on my jet." So... it's not that.

Jess Mah

This plane is a **Cessna Citation CJ3+**. I fly planes for fun—it's been my passion and hobby since, I think, elementary school. I was obsessed with airplanes, and it was always my goal to be able to afford to fly one. Then I learned... I interviewed a bunch of very wealthy people and asked, "How do you afford an airplane? How successful do you have to be?" The secret was: you don't have to be that successful. You just have to have a **big tax bill and good cash flow**.

Shaan Puri

[It] takes success to get to that. But it...

Jess Mah

It takes some success, actually, because it's like a house. You could finance it—put **20% down** and then... the rest.

Shaan Puri

We'll walk through that in a second. The funny thing was, we did an episode—a normal episode—where we were on Zoom, and it was great. You can go see it. It's called something like **"Jess Ma: High School Dropout"**—we YouTubed it to make the title good. I don't know, **300,000–400,000** people have listened to that interview across all the platforms. 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, "Alright, let's go—I'll meet you there." 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—how can I do it? What are the ideas?"

Jess Mah

Uh-huh.</FormattedResponse>

Shaan Puri

He's *idea-poor*; you're very *idea-rich*. So I thought, okay — it's kind of fitting, because one of the things we'll talk about at the end is: you've talked to a lot of rich people and tried to learn what the options are, what the possibilities are as far as taxes go. And that's — yeah, I want to learn that from you.

Jess Mah

Yeah, I mean, we'll talk about that as it relates to business ideas, but as it relates to tax ideas, it's actually a pretty similar process. I'll just talk to as many people as possible. I think the mistake people make with taxes is they have their one tax person, 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—I’ve talked to dozens of... </FormattedResponse>

Shaan Puri

"Tax promiscuous."

Jess Mah

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 suggestions. Then I talk to all my friends, ask them for their tax ideas, and consolidate them.

Shaan Puri

That's so true. There's this weird loyalty — like, "he's been doing my taxes for four years." But nothing has changed. And yeah, you want to get ideas from everyone, so let's do this plan real quick. For a plan like this, what does it cost roughly? What do you have to put down, and what are the tax savings or something? This is the mini tax lesson for this plan.

Jess Mah

Yeah, **mini tax lesson**, and then we go into more detail on this in the last episode I did with you guys. But this is a $12,000,000+ airplane, and you could put 20% down on the airplane. I got this pre-owned, so I saved a few million dollars, and it's just as good as new.

Shaan Puri

So, you put down *roughly* $2,000,000.

Jess Mah

Yeah. You put down about a few million dollars and then you just pay monthly financing on it. But then 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 $12,000,000 airplane and financed it, you can write off the whole $12,000,000 on your tax bill even though you only put in $3,000,000. So you're going to pay the government—or you could buy an airplane, right? It looks ridiculous.

Shaan Puri

Million dollars is going out of your bank account.

Jess Mah

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

Shaan Puri

Right.

Jess Mah

And I just wanted to *debunk that myth*. 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.

Shaan Puri

Right. You use it to *literally* be more efficient and to go meet people where, otherwise, you might not have taken that day trip to do it. You came up and said, "I want to have lunch with you," so you flew up, we had lunch, and you flew out.

Jess Mah

*And I was...*

Shaan Puri

Wow. First I felt *honored*. But secondly—yeah, man—there's probably a lot of people that I think I would have kind of amazing opportunities with or could build a relationship with, but I don't do it because the logistics are actually in the way. Of course, this is **not accessible to most people**, but if you're in that successful-entrepreneur bucket, it kinda makes sense logistically as well.

Jess Mah

It does. Yeah. We have **Starlink** on board, so when flying out here, people want to make five phone calls, be on Zoom, and do FaceTime video. I'm like, "Yo—what's up?"

Shaan Puri

Right.

Jess Mah

And like, 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 shit on by your employees, your customers, your investors. I realized that would be a problem for me a few years ago, so that's why I stopped being an operating CEO. Actually, it was really—I had this conflict of, "Can I do everything I want to do?" I know it's the right thing to do. I know I will... well, I know I'll create more abundance.

Shaan Puri

Right.

Jess Mah

You know, I'll **create more value for my companies**, but at the same time I know I'm going to get more flak. I want to have more people who want to rip on me—unfortunately. I'm sure this video won't help with that at all, but I defend it; it's a practical matter.

Shaan Puri

Right — I love that, *unapologetic*. So yeah, enough about the private jet. It's cool. It's gonna make for a great, great... first time for the podcast. What I want to talk to you about is what you're great at: **ideas**—coming up with new ideas for businesses. So the track record here is you've been an operating CEO. You started this company called *Intonero* when you were really young, right? How old were you when you started that?

Jess Mah

I was 19 when I started. I knew absolutely nothing. Then I built that company up and 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 want to be super honest about it."

Shaan Puri

That's interesting.

Jess Mah

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

Shaan Puri

Right.

Jess Mah

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*.

Shaan Puri

A barn full of horses.

Jess Mah

Yeah, a barn full of horses, where I create. I think we...

Shaan Puri

Just coined something there, by the way.

Jess Mah

That was all you—good work. But yeah, if I could raise less VC money for these companies and create more of them, and not be directly operating them, 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.

Shaan Puri

Miserable.

Jess Mah

So miserable and so stressed out. They don't have the ability to live an amazing lifestyle because of all the stuff you 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 **5%** of a billion-dollar company, which is a remarkable amount of money—a lot, but, you know...

Shaan Puri

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

Jess Mah

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

Shaan Puri

"There's other people who are in it for the *impact*. That's dope. They should do that — they should save the world. I'm on the world [unclear phrase]; I'm glad that they're saving it. Yeah, 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."

Jess Mah

That's *totally* what I... what I like.

Shaan Puri

"That's my — that's my gold standard." So your story is basically: at 19 years old, you started *Indoneiro*. You ran that company and grew it. Then, as you said, you transitioned from starting and running companies yourself to now having your own holdco, where you're incubating or creating companies. You also said that in the last four years you've started four companies, each worth over $100,000,000.

Jess Mah

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

Shaan Puri

Alright—hey, real quick: if you're liking this episode with **Jess**, we got something cool for you. When the episode ended, we asked her, "You were talking about how you have this playbook, this recruiting guide, this content guide—would you mind sharing one of those with us?" She actually sent us all of them. She wanted listeners to have them for free, so they're in the show notes below. It's her **Talent Playbook**, her recruiting guide, and I think an operations guide for how she runs her companies. These are straight from her and they're available in the show notes below—check them out. Someone's giving you *free gold*; all you have to do is put out your hands and accept it. Alright, back to this episode. I want to ask you about your idea process because that's amazing to be able to do. I want to be able to do that. So let's talk about ideas: how do you get ideas to start these companies, and what are some ideas right now that you're excited about?

Jess Mah

I love **Y Combinator** — *Request for Startups*. When I was coming up with my first ideas for businesses, like **Indoneiro**, that list inspired me. It's a list of 100 business ideas where they say, "If you build this, we are more likely to fund you." I really wanted to get into Y Combinator. I put together a spreadsheet — a matrix of criteria. 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 leg room. Another criterion was that I could **pseudo-bootstrap**: I could raise some angel money, but I didn't need to raise $100,000,000. I'm not going to build Tesla or SpaceX. I wanted to build something that $2,000,000 could get me very far. My other criterion was **recurring revenue** — something sticky, a "must-have." I literally went through every single idea on the Y Combinator list and rank-ordered them based on those three criteria. Business accounting and tax management seemed like the right one for my criteria. My process is: I go online and scrape these ideas. I've even gone to Reddit to look for ideas. I have one-on-one lunches and dinners with people and I just say, "Hey, what are ideas you're exploring?" and we brainstorm. None of the ideas I've actually worked on came from me sitting in a room with a whiteboard and just coming up with stuff.

Shaan Puri

Yourself.

Jess Mah

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

Shaan Puri

Okay, so you had this thing on your phone — this idea database. Yeah? It was like **300 ideas**, right? And you promised, you said, "I'll show some of them today," even though these are things you might still go do, I think.

Jess Mah

I *might* still do some of these.

Shaan Puri

So, do you want to give us a couple of...?

Jess Mah

"Absolutely. It's called the **Idea Hopper**. Actually, let me pull it up on my phone real quick. Great — should we start with the ones we talked about before?"

Shaan Puri

Yeah. She gave me a teaser of two or three of them, and I was like, "Don't tell me more," but yes.

Jess Mah

"Like, we start with the **Doge as a Service**."

Shaan Puri

Okay. Yeah, yeah. *I like, I like this one.*

Jess Mah

So, yeah.

Shaan Puri

So, it's my assumption.

Jess Mah

Right now.

Shaan Puri

Explain *"Doge as a service"* for companies.

Jess Mah

Yeah, I mean, most companies have so much waste. You have people who barely show up or they're phoning it in. I have friends who say, "Oh yeah... my husband *quiet-quit* his job — he's 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 actually using their computer, and if not, then they're fired? Do it just as a service for companies.

Shaan Puri

And so, it would be a team of consultants — consultants plus **AI**. How would you do it?

Jess Mah

I think **AI** could do a lot of it. I also thought that if you're an enterprise, you could sell this to consulting firms like **McKinsey** or **VC** firms—or whoever—and say, "Hey, you guys can offer this to the **CFO**."

Shaan Puri

Oh, they're *already* doing it — they're *already* in there.

Jess Mah

They're already in there, and that makes you seem more valuable as a consultant. You could say, "Hey — we could demonstrate that we'll save you hundreds of millions of dollars. You'll pay us only $20 million, and this **AI** did all the work."

Shaan 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. What McKinsey is amazing at is they have this relationship with a Fortune 100 company: they're on retainer and they're getting paid millions of dollars a year. If you can sell them a tool that either helps them *land and expand* that contract or just saves overhead in actually executing that contract, that's going to be pretty valuable. If I were building AI right now, I would not try to make something where 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.

Jess Mah

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

Shaan Puri

"And so, you're **not afraid** to share ideas? What's your philosophy around that?"

Jess Mah

"No, I'm *super* afraid to share ideas."

Shaan Puri

"Put you on the spot."

Jess Mah

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

Shaan Puri

Okay, I like it.

Jess Mah

I didn't want to be one of those people who said, "Okay, here are my *shittiest* ideas—now you go do the company." I think that'd be just really lame. </FormattedResponse>

Shaan Puri

"Totally. Alright—what else you got? That was just a service. *That's one I like.*"

Jess Mah

So, again, this is the *trendy category*.

Shaan Puri

Okay.

Jess Mah

Okay. Another idea: everyone says "SaaS is dead; agents are the new thing." Well, what if you could build vertical **agent-as-a-service** for an industry? For example, build a library of agents for dental offices, auto mechanics, clothing designers, manufacturers, distributors, etc. There are many industries that need their own very specific library of agents to automate tasks, and you can go really deep there. This is more of a thematic business area, and I think we're going to see thousands of businesses doing this. </FormattedResponse>

Shaan Puri

Right. So, okay—somebody's building a tool. You're saying you don't even have to build the agent. There's going to be somebody who builds an agent that's about picking up a call and booking an appointment. Let's say an **appointment-booking agent**. What you used to have to pay a receptionist to do, now AI's pretty damn good — it's going to be able to do that fully.

Jess Mah

Right, so you have **horizontal companies** right now that sell the **voice agent** for any industry. The problem is, you still have to do a lot of fine-tuning and work for if you're... [sentence unfinished]

Shaan Puri

Dentist

Jess Mah

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

Shaan Puri

Right.

Jess Mah

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

Shaan Puri

Gotcha.

Jess Mah

Gotcha. *Idea in a nutshell.*</FormattedResponse>

Shaan Puri

Okay, I like that. And you?

Jess Mah

You should do this for an industry you know about. If you're passionate about **dental offices**, then do it in **dental offices**. So that's...

Shaan Puri

**Shout-out** to anyone who's passionate about dental offices. You are — this was your day. You got it.

Jess Mah

I know, but the more recognizable you are, the more boring the better. Yeah, that's the Constellation Software model, right?

Shaan Puri

So, we invested in this company that's *vertical SaaS* which was called **Shop Genie**. We invested in it and, I think, within a year or two they sold for mid-eight figures. What they did was they went to auto repair shops and they were like, "Hey, guess what? Auto repair shops need a **CRM**." There were always CRMs like **HubSpot** and others that work for any type of business, and he's like, "Well, auto repair shops have specific things that are, you know..." [trails off]

Jess Mah

Very specific.

Shaan Puri

For them, so they built a tool that was just for them. Then they went and got about **3,000 to 4,000** auto repair shops in about a year to use it. And, by the way... </FormattedResponse>

Jess Mah

Very sexy business.</FormattedResponse>

Shaan 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. Then all these people, you know, followed on board. That guy makes, like, **$20,000,000** a year as the biggest influencer to other auto repair shop owners. It's really insane.'"

Jess Mah

Oh, wow — there's **riches** in that business idea, yeah.

Shaan Puri

So, what they did was they gave him this tool. It was for booking appointments and then text-message follow-ups, or whatever. What you're saying is: *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...

Jess Mah

"Vertical as agent says the service." [transcription uncertainty: original word "ass" may have been "as" or "SaaS"] </FormattedResponse>

Shaan Puri

Vertical ass. I love it. Alright.

Jess Mah

So, seriously — the more random, the better. If you could apply this to marine shipping or to resource mining, then Constellation will be acquiring and rolling up these *vertical-ass* companies in the next few years. **That's the future.**

Shaan Puri

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

Jess Mah

Yeah, that was another idea I had on my *IdeaHopper*. The idea, in a nutshell, was: could we... Oh, right — it was a coating for these cargo ships.

Shaan Puri

"Coating — like the paint coating."

Jess Mah

To make it more efficient, these ships could go even a few knots faster. That saves a ton of money on fuel, and you wouldn't need to take the ships out of the water as often to recoat them. So this could be **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 the idea or looking at funding something like this many years ago, and the other person just didn't have the money to proceed with it.

Shaan Puri

Right.

Jess Mah

And so, I... I learned about that just from having dinner with someone.

Shaan Puri

Yeah, that's crazy. So, when—let's say you have an idea like that?

Jess Mah

Uh-huh.

Shaan Puri

So, first is, like, where—who the heck even thinks about **cargo ship coatings**?

Jess Mah

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

Shaan Puri

Right, so—you're a *good spotter*, would you say? Or what are you good at? </FormattedResponse>

Jess Mah

I'm good at initiating conversations with people who are likely to have ideas or access to ideas—like you; you have good access to ideas. </FormattedResponse>

Shaan Puri

So, actually, I've sent you an idea before. Now that I think about it, my buddy **James Currier** has this great phrase. He goes, "You wanna turn yourself into an API." What he means by that is: a website has an API which basically says, "Here's what I can offer you." I can give you location data, so you ping me, I give you location data — that's what I'm good at. And, by the way, here's what I wanna get from your API. Right? Here are the things I'm interested in: I'm interested in acquiring geospatial data. So you kinda have made your API like, "Hey, I'm always interested in hearing interesting, kinda weird, off-the-beaten-path ideas." So when I hear one, I think, "Oh, Jess would like this."

Jess Mah

Yeah.

Shaan Puri

Right. So you've put yourself in my mind and associated yourself with: she likes to hear *weird, cool, off-the-beaten-path ideas*. She's good at making them happen. Then, in return, people ask, "What are you good at? 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 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 an idea, she's really good at fleshing it out over lunch—riffing on it—and then being super motivated to say, 'Alright, what are we gonna do to make this happen? Let's push the ball forward.'" So I think you've kind of done that in the idea space, which...

Jess Mah

It's powerful, articulated. Yeah. I get people calling me all the time saying, "Hey, Jess, do you have 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. It's like, alright—yeah, I'll find time to call you back. But it's 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 process. I'm doing the same thing with ideas.

Shaan Puri

Yeah, that's great. My business partner, **Ben** — I was just thinking that while you were talking: his *vibe* is so funny. It's two things. First, Ben always knows a guy. You're like, "Do you know anybody?" He's like, "I know a guy who knows a guy." That's always Ben's thing — he always knows a guy who knows a guy. Second, a lot of people will go to Ben; they'll just text him when something good happens in their life. I'm always like, "Why did they — did you ask?" He's like, "No, no, they just told me, 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. What I realized is I do the same thing with him because he's somebody who makes you feel good when you win. You don't feel like there's any envy, and he's not going to try to take anything from you — he's genuinely pumped for you.

Jess Mah

That's awesome.

Shaan Puri

And because of that, he just gets this wealth of inbound—people who are winning. Which is also great for us as investors, because we're like, "Oh wow, these guys are doing really well. Do they need more capital? Do they need something? Maybe we could help them." That's a *superpower*. So I think there are these *underrated superpowers*. Like the thing you're describing: "I'm good at 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—nobody would even tell you that that's a thing. But you're going to build generational wealth off that.

Jess Mah

Yeah, that's well said. I think it's equally important to know what we're bad at. For me, I realized that I'm *not the best operating CEO* — that's just not my forte. After I realized that and made peace with it, I was able to say, "Okay, well, I'm going to come up with ideas, recruit great teams, and then empower them." That's what I want to figure out how to...

Shaan Puri

Be great.

Jess Mah

Put a worry on, and be great at exactly...

Shaan Puri

So, let's do more. **I want more ideas.** Yeah, okay — so you got me going.

Jess Mah

I have this other idea. The code name is **"Holy Hell."** I came up with it 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 medical providers get access to insurance. Then I did some research. I plugged this into **GPT** and realized there are so many other types of practitioners—like chiropractors or physical therapists—who can get insurance reimbursement but are so small they don't have the scale to negotiate with an insurance company on getting reimbursed, so they just charge.

Shaan Puri

Technically, could.

Jess Mah

"Technically, they could."

Shaan Puri

But is it that they don't have the *time* or the *skill*, or do you need to **band them together**?

Jess Mah

Both. So, if you band them together, then they can get some reimbursement. Then you could create — you know — **agents-as-a-service** to support them and create more lock‑in. You could also help them with customer acquisition. So it's gotta be the **full stack**. This other company did that for one of these different verticals, and I heard about it through a friend who heard about the company. 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..."

Shaan Puri

Some similar blueprint, but in a different space that...

Jess Mah

Needs exactly.

Shaan Puri

So you would go—*what would you do for that?* Let's just walk through this. I want to hear: you have that idea. I heard about this with a clue.

Jess Mah

I got a clue because I was having lunch with a friend, and he's like, "These guys are making **$30,000,000** in EBITDA." I'm like, "Alright."

Shaan Puri

And what question are you asking that friend? We were just talking before and I was like, "How the hell do you get this?" I said, "What is your *info diet*? Are you 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."

Jess Mah

Yeah, I mean, none of these come from reading a blog post or watching a podcast. All of 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 just talk to people.

Shaan Puri

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

Jess Mah

"I'd say, 'Yeah—what's the coolest, most interesting, exotic business idea that's minting cash that you've seen recently?' So I'm not asking them for a business idea; I'm asking them for an existing thing you've seen, right? *What's the key to their success?* *Why does no one know about this?* *Why hasn't anyone copied them yet?* *And why is now the right time for that?*"

Shaan Puri

So you're filtering. As they give you the exotic business that's *minting cash*, you're like, "Was there some **secret sauce** that's not replicable?" They know — maybe they're super influential in a community. Okay, that would take forever to build. Could this be done in another space? Does this take $100 million of venture capital, or... yeah? </FormattedResponse>

Jess Mah

"How should they start? And then they're like, 'Oh, yeah — these guys just *bootstrapped* it.'"

Shaan Puri

Right.

Jess Mah

I'm like, "Oh my God... so now my math is really watering."

Shaan Puri

Right.

Jess Mah

"I'm like, 'Okay—what are the other risks here? Can **AI** just replace this in **36 months**?' That's the new risk factor in my criteria that y'all have to ask."

Shaan Puri

For so, you get the clue — you get the clue from the conversation, the *key question*, yeah. Then you get the clue and you run it through your filter mentally, just there. Let's say now you're excited about the idea because you're like "holy health" [unclear phrase]. And you give it — you give it a code name.

Jess Mah

"Is there—everything has to have a *code name*?"

Shaan Puri

Is that why? Is that it? *It makes it real.*

Jess Mah

It makes it feel more *psychologically real*. Then I have something to remind me of the rest of the substance of the idea. </FormattedResponse>

Shaan Puri

Cool.

Jess Mah

And so I'll just throw the idea into *ChatGPT*.

Shaan Puri

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

Jess Mah

Yeah, exactly. I tell everyone: before you tell me anything, *think with AI* as well. And so everyone does that. I say, "Give me like **20 ideas** of potential names for this idea," and then I just pick one. This is the *code name*, and we put it in the idea hopper.

Shaan Puri

Did you see the CEO of Microsoft went on a podcast — I think Borgesh's podcast recently? He had this great line. He goes, "My new workflow is: *think with AI* and then *work with my coworkers.*" He says, "I think people are thinking about, like, AI is gonna replace your coworkers, or your employees — AI is just gonna 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 kinda doing a similar thing.

Jess Mah

Yeah, we definitely do that. What we're trying to do is have all of our meetings recorded. Even if it's in person, we're just, like, turning on Granola and using a big conference speakerphone. It's just recording everything, and we're going to feed it in to create *digital twins* of all of us. Then we'll have, basically, **thousands** of versions of ourselves just brainstorming and sparring with each other — to my God, amazing — refining ideas even further.

Shaan Puri

It's like those little chess arenas or whatever where they train the *AIs* to compete with each other until there's a winner or a *winning strategy*. </FormattedResponse>

Jess Mah

Yeah, and I... I should. How you?

Shaan Puri

Gonna do the *digital twin* thing.

Jess Mah

We're actually doing— we're training one *beast* off of you as well. We're going to have it watch every single video you've been part of so it knows how to think like you. It will be like, "Hey, bring Sean into these conversations. Bring Satya. Bring Suck. Bring Elon. Bring..."

Shaan Puri

That is.

Jess Mah

And I want all of them to help battle-test this conversation.

Shaan Puri

"That's amazing."

Jess Mah

And so that.

Shaan Puri

Way I.

Jess Mah

Don't need to pay for you.

Shaan Puri

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

Jess Mah

I'm bringing you 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. </FormattedResponse>

Shaan Puri

Like, is there a tool to do that, or are you going to make *your own* tool?

Jess Mah

Just to get the transcripts. Once you have the transcripts, you can feed them into any of these.

Shaan Puri

So any LLM will be able to...

Jess Mah

That's going to do a pretty good job. Yeah — we should go into a more advanced conversation on this, but that's...

Shaan Puri

It's interesting. Yeah, it's like... people will—dude, it's *so annoying*. People are using my voice in ads all the time now, and I'm like, "This is wild." I'm like, "How do I sue you? I don't even know who you are."

Jess Mah

Right.

Shaan Puri

Second thing is that... But I'm telling anybody who's doing it: **I'm suing you**. I'm actively working on that. I'm trying to use AI to figure out how.

Jess Mah

"To AI... AI. I judge AI. I'll sue people, yeah, for..." [trails off]

Shaan Puri

Then also, I'm...

Jess Mah

Working on that.

Shaan Puri

Also, what was the other one? Oh—*writing style*. People will just put in chat to me and be like, "Write this in the style 'whatever'," because I've written a lot of content publicly. It's not—it's not me, but it's definitely kind of 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 going to need 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 a real code word.

Jess Mah

I know, but it's like *really* exciting. So, yeah — Satya's... [unfinished sentence]

Shaan Puri

He's on?</FormattedResponse>

Jess Mah

"He's on here."

Shaan Puri

So, where was I? You were telling me about... Okay, so we're going through your process. *You get excited about the idea.*

Jess Mah

"Yeah, you have the clue."

Shaan Puri

You have the code name, and you then have a meeting with your team. Uh-huh. What are you doing in that meeting? What are you trying to *advance that idea forward*?

Jess Mah

Yeah. Every week we have a **R&D team meeting** — that's what we just call it. We talk about the ideas we're playing with. The problem here with *HolyHealth* — because this is a live idea, and it still is a live idea; everything I've shared today is still live — is that we just have too many of these ideas. I mean, we have hundreds of these ideas, and we try to work on too many at the same time. The problem is then you don't really advance any idea far enough between each weekly meeting, and we lose excitement.

Shaan Puri

Right.

Jess Mah

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

Shaan Puri

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

Jess Mah

In that meeting, anyone can pitch — so it's not just me. Everyone usually has different ideas. And so, yeah, it's like, "Here's an **AI-defensible idea**: x, y, z. Here's why it's a **Maui idea**." So we kind of have a common understanding of what a **Maui idea** is.

Shaan Puri

And which is roughly what?

Jess Mah

It's roughly an idea that can **cash flow**, that doesn't require a lot of outside funding. We could fund it ourselves. And it's *boring and complicated* enough that random people are not going to copy us—or reverse-engineer it—easily. Those are my ideas, and that's what I encourage anyone else to do.

Shaan Puri

Well, okay, so...

Jess Mah

If you're an auto mechanic expert, then that might be your theme or idea. We have that for financial services in particular.

Shaan Puri

Right. So, what... where do you leave that meeting? You say, "Alright, what are we gonna do next?"

Jess Mah

We say, "Okay, what are we going to get done to advance this between this week and next week?" We get very specific. It's like, "Alright: **Person A**, you're doing these five things; **Person B**, you're doing these five things." The next step might be, "Okay, let's just go call..." For **Holy Health**, the next step was: call some chiropractors and ask them—figure out who accepts insurance and who doesn't, and why. Then ask them, "Why don't you plug into these existing companies that should be doing something similar?" So a lot of it is just: what are the questions we're curious about?

Shaan Puri

And psychologically, are you trying to **disqualify** an idea or are you trying to **qualify** an idea? What's the mindset: is it, "I'm trying to figure out whether this is good or bad," or is it, "I'm listing the riskiest assumptions and testing them"? What are you trying to do during those next few weeks?

Jess Mah

It's not that we're trying to figure it out or disqualify it per se. 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, 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 then, "my customer acquisition is terrible because x, y, z." 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 ten pivots, right?

Shaan Puri

Which is very useful, because that's almost always the case. If you don't have that attitude, you basically hear something really juicy but you're so locked in. It's like somebody was handing you gold while you were out there searching for bronze. I was gonna ask you... you're talking a lot about ideas in Silicon Valley. There's this phrase: "**Ideas are worthless; execution is everything.**" Do you buy that?

Jess Mah

"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]."

Shaan Puri

"Valley, so what's your take?"

Jess Mah

My take is that ideas are *really freaking important*. If you have the wrong idea, you'd be a great team and you're screwed. Actually, I modified my thinking on this because I was a scout for Sequoia Capital for many years. They would show us a bunch of these great ideas with amazing traction, especially in consumer internet. Then they would ask us, "Would you invest on this memo — yes or no?" So we would vote. Then they'd say, "Well, here's what happened to that company: it ended up being a cro." Even though it had the best team, the idea was still garbage, so it ended up being a cro — and that was a common theme I noticed.

Shaan Puri

So, they would train—*almost* train you—on historical memos, basically.

Jess Mah

Yeah.

Shaan Puri

Oh wow, that's incredible. But if the *traction* was great, is it the use of the *traction* that's good, or is it just the *team and the thesis* that were great? </FormattedResponse>

Jess Mah

I mean, the early traction might have been good, and the team looks good. But if you really think through the long term: is this idea *sticky* after a year or two? Will there be *copycats*? Is there anything that really holds the consumer in? That's where these ideas would lose steam — and die. So that kind of helped me think about this a bit differently.

Shaan Puri

"And so you're saying *ideas* are **super important**?"

Jess Mah

Ideas are really important and the team is really important — they're both really important. But to say, **"ideas are a dime a dozen"**... really? It's not just the idea. It's the whole thinking of the business: doing the calls, meeting with the chiropractors in person or the auto mechanic, and really figuring out those juicy tidbits you won't find by sending out a stupid survey or by using **ChatGPT** to tell you, "Hey, what are the problems that chiropractors have?" That helps you build an interview script for what you're going to talk to them about. But then, you have to **show up**. When I was building in an arrow, I would go to Yelp and call these CPAs. I would say, "Hey, I'm a 19-year-old college kid. I know nothing about business. I want to do something to help accountants. Could I come to you, buy you lunch, and just ask you some questions for fifteen minutes?" Then you show up — they're not going to kick you out after fifteen minutes. Fifteen minutes is going to turn into two hours. You have your notepad, you're scribbling. They love that; they want to be helpful.

Shaan Puri

Right.

Jess Mah

I did a lot of that personally: I just showed up, asked them my questions, and got all these insights. We still do that — I'm still on these calls. Even if it's not in person, you can at least do hour-long (or longer) expert calls. We use **GLG** for this. There's also **AlphaSights**, and they charge a lot. You might be paying $800 to $1,000 to talk to an expert in a very difficult-to-find area. By contrast, for accountants and chiropractors you can just call someone on the internet. But if you want an expert in **titanium mining**, how are you going to find that person? You go to **GLG**, you pay them $1,000, and they'll find the person for you and set up the phone call.

Shaan Puri

Right.

Jess Mah

And we do that all the time.

Shaan Puri

The way you're talking about ideas and markets reminds me of a story about a marketer. He goes to a seminar with other marketers. The speaker says, "Let's pretend we're opening up a hot dog stand." Then the speaker adds, "I'm a genie—I will give you anything you want to make your hot dog stand the most successful you can make it." He asks, "So, what do you want?" One person says, "I want the best ingredients, best buns." The genie replies, "Got it—best buns." Another person says, "No, no—buns are foolish. In the food business, location is everything," and the genie answers, "Alright, I got you: this corner spot in a high-traffic area." Each person asks for the best branding, the best whatever. Finally, one person says something that he thinks will beat all of the others if everyone got their wish granted. He says, "All I want is a **starving crowd**." If you're a marketer, you're going to spend a lot of time and energy trying to sell something. The absolute best decision you can make up front is finding a starving, ravenous crowd. When you talk about ideas, what's underneath an idea is a customer—or a set of customers—who have a real pain and a desire to solve that pain. They are hungry. If you just show up with even decent buns and hot dogs, they'll buy it instantaneously. It's okay if it's a little cold; it doesn't matter.

Jess Mah

Yeah, that's a great story. It's about how acute this problem is. Ideally, 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.

Shaan Puri

So, you like that model because there's *love*—**no friction**, that.

Jess Mah

**Model** — it's like, "Why would you say no to that? It's like you're just saying no to more business."

Shaan Puri

"Yeah, that's like those companies that negotiate with all vendors on your behalf. They'll say, 'Whatever we save, we'll take 20%.' Or, 'You're paying nothing today; if I save you any money, I'll take 20%.' And it's like, 'Okay, go have at it.' You were talking about—you had a couple other ideas. You had a divorce one. What?"

Jess Mah

Was that one? Yeah — that was like... I had so many friends chanting "divorced," and still do. People say they need an advance on their alimony, or their money gets tied up and locked up because they're in divorce proceedings. They're really rich, really successful, but they can't tap any of their own capital while it's all tied up. So what if we could just give them some of their money back? And so that was just, like, a funny, random...

Shaan Puri

*Creative financing* around the window of a divorce—or the alimony.

Jess Mah

"We called it *divorce.fund*."

Shaan Puri

"Didn't go forward with that one."

Jess Mah

No, I mean, people talk about it and stuff. We still joke about it, but there are other ideas that we got more excited about, so...</FormattedResponse>

Shaan Puri

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

Jess Mah

So many failures.

Shaan Puri

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

Jess Mah

Yeah. I mean, I would start by saying: when I use **YouTube** and watch all these entrepreneur/business podcasts, I spend a lot of time flipping through and I think, "Man, I'm not doing enough; I'm not good enough." Even when I watch your podcast I think that. I think a lot of people probably share that view. And the people you interview—I know a lot of them. These are my friends. I know what they're secretly struggling with, and they're not necessarily sharing all of that. I think that's important to know. In my case, it looks like I'm good at coming up with these things and having success, but most of the time they're total duds. One example: we had this idea we called *CredBoost*. Terrible idea in hindsight. I'm so embarrassed to share this, but I'm going to share it anyway. The idea was: we're going to help you improve and repair your credit. We had the customer-acquisition funnel set up—**high churn, low price**. It faced very high regulation by the **FTC** and got compared too much to credit-repair businesses. My pitch was, "We're gonna boost your credit, not just repair it." It could have made some money, but we got bored with it. I burned a few $100,000 experimenting with that, and then I put in the wrong team. I made so many mistakes on that. That was an early incubation that went nowhere. Another idea was: we're going to help veterans of the U.S. military find new jobs, and we'd get paid by VetTech and the **GI Bill** to do that. We could do this all online—it's virtual and scalable—and we're helping veterans. It felt like...

Shaan Puri

It was.

Jess Mah

Really good. Yeah, yeah — and the veterans, all they had to do was say yes. So we launched all these ads; all these veterans signed up. They were like, "Hell yeah — I could double my salary, make more money, and do this all online from the comfort of my home." Our payment mechanism was this thing called **VetTech** (spelled v e t t e c). It had bipartisan acceptance — everyone loved it. But it got stuck: it was approved by the House and never went up to the Senate, and the money dried up. We thought, "Alright, well it'll get renewed imminently." Eighteen months later, still not renewed — today, still not renewed. We were like, "Okay, well the hat business died just because of that." Then I tried to pivot. I thought, "Can I get the **GI Bill** to pay for it?" But the GI Bill requires in-person attendance, and after that we lost interest. I was the only one still excited about this, like, "Guys, we gotta help the veterans."

Shaan Puri

Right.

Jess Mah

My team's like, "We have other ideas that will make more money." "Justin, we wanna make money." *Yeah.* "Alright, I'll come back to this when the time's right."

Shaan Puri

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

Jess Mah

Oh man — it's not just 2011.

Shaan Puri

This is when it hurts... but not just because an idea is wrong. Sometimes it's even when the idea is *right*. </FormattedResponse>

Jess Mah

Yeah.

Shaan Puri

"And you're running a company. Can you—can you read this? I want you to read that."

Jess Mah

I wrote this to my mom and my dad on **Saturday, 06/04/2011 at 5:56 AM**. I was up all night; I couldn't go to sleep. I was so upset.

Shaan Puri

**Subject line.**

Jess Mah

Kind of sad. I feel like I'm *Bernie Madoff* — rich 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 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.

Shaan Puri

Wow

Jess Mah

And my mom—she's an entrepreneur. She came here. I absolutely remember that night. I remember how I was just very upset because I had all these hoops and expectations on myself. And, you know, Paul Graham—he was my mentor—and he said, "You're gonna be one of the greatest entrepreneurs of all time: you, Patrick Collison, and Sam Altman." I'm still the *least successful* today, and I still think about that often...

Shaan Puri

So that weight was on your shoulders. </FormattedResponse>

Jess Mah

That weight was fully on my shoulders. It still is on my shoulders. Then my mom called me and she said, "Hey, I love you no matter what. Even if you're a *total business failure*, I'll still love you." I just cut all my expenses, cut my burn, moved into a tiny apartment with my business partner, and then slowly crawled out of the hole. We grew into, you know, a few hundred employees — a profitable, good business. Not a unicorn, but it gave me all the training and spiritual training.

Shaan Puri

Right.

Jess Mah

To pursue entrepreneurship and be comfortable with mistakes and failure.

Shaan Puri

Were you at that time? I guess, what was the conversation with yourself? Because you're like, "I did these things, I lowered my burn, I did this, I did this"—those are the actions. But before the action comes, there's some **inner monologue**. There's some conversation you gotta have with yourself. 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. I think training that—learning how to improve that inner monologue—is so important. And it gets better in moments like this, right? That's when it gets... that's the muscle-building for that inner monologue. Do you remember what you were telling yourself at that phase? You wrote this, your mom tells you something—what did you tell yourself?

Jess Mah

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 falling behind. I need to diagnose what went wrong, and I need to keep on trying. I will not accept or tolerate failure." That was what was going through my head. Were you?

Shaan Puri

Listening to a song at that time. Where'd that come from? That was *fire*.

Jess Mah

No, it was.

Shaan Puri

"Just how did you get yourself into that state — from kind of sad to, like, kind of **kick-ass**?"

Jess Mah

No — that was *sad*, though. It was not an *empowered* attitude. I was thinking that. But because I knew that was my situation, it went from, "Alright, I need to do all this or I'm screwed," to, "Alright, I'm really sad and I have to process my emotions."

Shaan Puri

Right.

Jess Mah

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

Shaan Puri

Right. You know, I've done, whatever, 600 of these episodes. At a certain point, you'd have to be sort of stupid to not realize there's a common mindset that I think great entrepreneurs have. I've distilled it down into this. I think a great entrepreneur's mindset is: - **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. - **Realistic about the present**, which is kind of what you said: > "I'm not showing up at my best. I'm not putting in all the effort. I'm not doing the obvious things I should be doing right now." But it's also not over. They don't make the situation worse than it is, and they don't make it better than it is. They see it as it actually is. - **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. </FormattedResponse>

Jess Mah

"Yeah, that's really well articulated. I think, also, going through moments like that—I remember talking to my business partner and we did a full postmortem. We listed out every single strategic and tactical mistake, every thing we did wrong, and what we would do differently if we went back in time. I wish I had written this somewhere because it was a long list. I mean, the attitude was, *'I would do everything different if I could go back in time.'* Even yesterday I was talking to one of my colleagues about the number of bad ideas we funded and experimented with, and our process flaws. We would also do everything differently going three years back. That's correct—we could—but we're talking about this constantly, and that goes back to what we talked about at first: **kodawari**. 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 them. It doesn't have to be only when times are tough or when you're about to run out of money that you're reflecting on everything."

Shaan Puri

Yeah, yeah — **no old mistakes**. It's kinda like the "no new friends" idea: it's the "no old mistakes" of what you want. You don't want to keep making the same mistakes again. You said, when you were talking, "I'm not—" you said, "I'm not showing up the way I need to." You said, "I'm not playing to win." That's something. While I was talking to your boyfriend before this, I asked him, "What's a Jess-ism?" Meaning, if you talk to people enough, you sort of see the things they repeat — the things that are their philosophy, that they're actually operating on. He said something like, **"Play to win. Don't play not to lose."** Explain that.

Jess Mah

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

Shaan Puri

Right. What's an example—maybe non-business-related—where, in your life, you had the moment when you thought, "Ugh, I need to *play to win* here instead of playing *not to lose*?"

Jess Mah

Personal life — for example, with the airplane: this is a *physical manifestation* of that attitude, and that's why it's really fun to share it with everyone. Today, it's easy to say, "I'm going to be frugal. I'm going to save the money. I'm going to let it compound. I'm going to invest it in my other businesses." Or, "No — screw it. I'm playing a win here." This is going to manifest way more **abundance** for me than if I don't.

Shaan Puri

Or you had told me something that, when we were at lunch, 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 in your job — I'll pay you that or more," or whatever. You said, "I want to have four events a year in these four cities with the most inspiring, fun people. I want to create — to engineer some serendipity, some luck, some fun, some cross-pollination of people and ideas four times a year in these places." I remember. I've told probably five people this because, wow, you need some resources to do it. Yes. Of course, of course. And, 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; 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.

Jess Mah

Yeah

Shaan Puri

Right. I kinda know—if I did it really well, I would: **a)** have a lot of fun, and **b)** yeah, I do think good things would happen. But you took almost an *intentional business capital-allocation approach* to the luck-and-fun part of your life, which I think most people leave untouched. Luck and fun are just things that either happen or don'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 that same brain for both.

Jess Mah

Yeah, because I wanted to kill two birds with one stone—or three birds with one stone. I want to have fun, do more business, and meet cool people. But I also had this friend who hated her private equity job and really wanted an excuse to leave, 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. We're launching the first one *literally today*—that's exactly what I'm flying off to after we're done. Then the vision is we'll do a summer thing, a fall thing, etcetera. But it was really expensive. So what she and I decided to do was help her find other work, other events. I'd set her up with my other friends throwing events.

Shaan Puri

Right.

Jess Mah

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

Shaan Puri

Right.

Jess Mah

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

Shaan Puri

"What type of person — like, what skill set do they have that you found out? You just said, 'like *Fiverr* or *Upwork*.'"

Jess Mah

Yeah. One's a product-management, UI/UX thinker. One is a financial-services guy. One was an intern of mine—he was at UCLA. He asked me to speak to his entrepreneur club, and then he said, "Hey, could I take you to lunch? I want to get some advice from you—what should I do after college?" I said, "Just intern for me and I'll teach you the ropes." He was so good that now he's full-time with us, and he's probably one of my best partners for borrowing ideas. Then there's this event-planning person I met through 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 together. **That's more important than the resume.**

Shaan Puri

Right. I met a friend recently who told me this. He said something in passing: "I was at this event... there was this guy who was dressed differently," and my friend and I—**we collect eccentric people**—so we went over to him and had a chat. I kind of paused him and thought, "That's kind of a cool thing you just said: 'I collect eccentric people.'" I don't do that. I was like, *what do I collect?* I just put myself in a position of asking, "If I said, 'What am I a collector of?' what would I say?" 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. 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. So I'm a great collector of those. I'm also a collector of young talent. If I see somebody who's young, who's hustling or who is talented in some way, I will really help them out because I want to: a) **stay young myself** and be helpful, and b) be able to **connect dots** between young people and good opportunities—or young people and funding, or whatever it is. So I think there's this interesting idea of figuring out: what is it that you collect? Some dudes collect stamps, some dudes collect bugs. What is it that you collect? So, for you, what would you say you collect?

Jess Mah

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.

Shaan Puri

"That's your **Venn diagram**."

Jess Mah

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

Shaan Puri

**Right, right — engineering the serendipity.** Our buddy **Nick Gray** does a no-cost/low-cost version of this. He used to run *Renegade Museum Tours*. He loved museums, so his Venn diagram was "fun people" who were interested in going to a museum on a Friday night. He would host the tours — he wasn't part of the museum — because he knew the museum better than the official tour guides. He took people on a more playful version of the tour: they'd have a drink outside beforehand, go in, and do little fun things at the different stations. Another way he engineered serendipity was by throwing singles events. He himself was looking to date someone, but instead of just using an app and "swiping left or right," he created a creative alternative that could help him find someone amazing — and maybe help a bunch of his friends find someone too. These were low-budget affairs — "it's a pizza budget," not something super fancy.

Jess Mah

It has.

Shaan Puri

*To be fancy,* right? It does. I feel like I need to say that because we're sitting on this jet... but, yeah.

Jess Mah

I mean, most of the stuff we do is very cheap and cost-effective. It *pays for itself* and sometimes even makes a profit, right?

Shaan Puri

Know, so, like—just taking that intensity to *engineering some serendipity*. I kinda love that. Before we leave, just leave me with this: what are you currently *nerding out* about?

Jess Mah

I've been spending a lot of time thinking about cancer and oncology. I've been thinking a lot about longevity, and we're still funding a lot of the research with **Mike Levin**, who is my favorite scientist of all time. He's the *bioelectricity ninja*, and I've been nerding out on this a bit more. I mentioned to you before we got here that I've been in a bit of a sad mood this week. I had a friend die of cancer a few days ago — she never smoked a cigarette in her life and had stage four lung cancer. It's just more examples of this in my life; every year or two I lose a friend like that. So it's not necessarily going to make money or improve my lifestyle, but I'm just like, I gotta nerd out on it.

Shaan Puri

Right — is there exciting progress in the cancer/oncology field right now? Is there something — a *new paradigm* or a *new pathway* that's interesting?

Jess Mah

Yeah. With Mike, he talks about how he's been able to use *bioelectricity* to normalize cancer cells. So everyone right now in the field is asking, "How do you kill a cancer?" Think about chemo and radiation—they're really painful for the patient. But if you could just normalize cancer and not have to kill it, that's going to be a lot more comfortable.

Shaan Puri

It makes it like a normal, *non-cancerous* cell, basically.

Jess Mah

It's still going to 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 animals live longer. I don't think he wants me to talk about it publicly yet, but...

Shaan Puri

"How insane is the **AI**? AI for medicine and biology—yeah, for **AI**, how insane is that going to be?"

Jess Mah

I think it's gonna be amazing. I think it's also gonna be a lot harder than people think, because 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. That's one area where we're going to see slower progress than everyone is bragging about. Whereas, with everything else we discussed with digital twins — if you could have two of us brainstorm ideas, there's no bottleneck there.

Shaan Puri

Right, right.

Jess Mah

Right. The only bottleneck is spinning up the computer and then us pulling the trigger to fund ads or fund whatever. But in health and bio, **people's lives are at stake**, so it's going to move slowly still, I think — unfortunately.

Shaan Puri

Okay, well, where should people find you, and what should they send you?</FormattedResponse>

Jess Mah

Yeah, if you have any exotic, outside-of-the-box business ideas you want to run by me, I'd love to discuss them. Shoot me a note. I am on **LinkedIn**—just search **"Jess Ma."** I post on my blog there almost every week, partially using **ChatGPT** to come up with my blog posts, but I still review them. I'm like, "Hey, write me a blog post that's **2,950 characters** long because the LinkedIn limit's 3,000, okay? In my voice, about X, Y, C, and insert these anecdotal stories." And then, within two minutes, I have a blog post.

Shaan Puri

That's amazing.

Jess Mah

Yeah, so I post there. These are **real-life stories** from my life. Just send me a message on **LinkedIn** — *would love to hear from people*. Also, from the last pod we did, I made a bunch of friends.</FormattedResponse>

Shaan Puri

Oh.</FormattedResponse>

Jess Mah

Great — people just *cold-emailed* me, and I'm like, "Yeah, I'll grab lunch with you. I'll grab dinner with you." Two people I met from the pod are coming to my retreat.

Shaan Puri

That's amazing to hear. That's a point of pride for us. We want it to be that when somebody comes on the podcast, they should get more inbound messages from this than from any other podcast they go on. The second measure is that the people who message you are people you would actually want to talk to. That would be the **goal**, right? If we're doing that, we've kind of built the **right tribe** here. </FormattedResponse>

Jess Mah

Yeah. I'm glad job — you're with that real community, so thanks for having me here.

Shaan Puri

Awesome. Well, **cheers, cheers.** Alright, here we go.