Sam and Shaan sit down with Jess, a serial entrepreneur who has co-founded several nine-figure businesses, aboard her private Citation CJ3+ jet. The conversation covers her idea generation process (the “idea hopper”), her framework for evaluating businesses, notable failures, the mindset required to push through hardship, and how she engineers luck through intentional events and networking.
Speakers: Sam Parr (host), Shaan Puri (host), Jess (entrepreneur, guest)
Opening on the Plane — Private Jet Tax Strategy [00:00:00]
Sam: We should address the elephant in the room. Why are we on a plane?
Sam: So we’re just flexing on everybody now? This is my Tai Lopez moment — “Hey guys, I’m just on my jet.”
Jess: It’s not that. This plane is a Citation CJ3+, and I fly planes for fun. It’s been my passion and my hobby since elementary school. I was obsessed with airplanes, and it was always my goal to be able to afford to fly one.
Jess: I interviewed a bunch of very wealthy people and I said, “How do you afford an airplane? 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. It takes some success, but less than you think — a lot less than you think. Because it’s like a house. You could finance it, put 20% down, and the rest — we’ll walk through that in a second.
Sam: The funny thing was we did a normal episode on Zoom and it was great. You can go see it — it’s called something like the high school dropout episode. Like 300–400,000 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. Meet me here.” I was like, all right, let’s go.
Sam: And the second thing is you’re actually great with tax hacks — better than my accountant, who I pay to come up with ideas to lower my tax bill. And he’s idea-poor. You’re very idea-rich. So I thought it was fitting, because one of the things we’ll talk about at the end is your whole thing about learning from wealthy people what the options are when it comes to taxes.
Jess: Yeah. As it relates to tax ideas, it’s actually a pretty similar process to everything else. You just talk to as many people as possible. The mistake people make with taxes is they have their one tax person — that person worked with their parents, they’ve been loyal — but this is a very bad place to have loyalty. I’ve talked to dozens of tax attorneys and accountants about their ideas, I keep track of all of them, and I talk to all my friends and ask for their tax ideas too. Consolidate everything.
Sam: That’s so true. There’s this weird loyalty. Like, “Yeah, he’s been doing my taxes for four years.” Yeah, but nothing has changed. You want good ideas from everybody.
Sam: So let’s do the plane real quick. A plane like this — what does it cost, what do you put down, and what are the tax savings?
Jess: So this is a $12 million-plus airplane. You could put 20% down. I got it pre-owned, so I saved a few million bucks and it’s just as good as new. You put down roughly a few million bucks and then you just pay monthly financing. But then you get to write off up to the whole thing. Last year it was 60% upfront, but with the new administration it looks like accelerated depreciation is back. So if you bought a $12 million airplane and financed it, you can write off the whole $12 million off your tax bill — even though you only put in $3 million.
Jess: So you’re going to pay the government, or you could buy an airplane. Either way, $3 million is going out of your bank account. It looks lavish, it looks ridiculous, but this is why rich people do these things. I wanted to debunk that myth. A lot of people are scared to admit it — they don’t want to share it because they want to flex more. But it’s just a practical matter, right? And you use it to literally be more efficient and go meet people where you otherwise might not have taken the day trip.
Jess: Like, you came up, we had lunch, you flew out. And I was like, wow. First I felt honored, but secondly — there are probably a lot of people I could have amazing opportunities with or build relationships with, but I don’t do it because the logistics get in the way.
Jess: Of course, this is not accessible to most people. But if you’re in that successful entrepreneur bucket, it kind of makes sense logistically as well. We’ve got Starlink on board, so flying out here I was able to make five phone calls, be on Zoom, do FaceTime video. It’s a practical matter of saving money, but it looks really bad. If you’re an operating CEO, you’re going to get shouted on by your employees, your customers, your investors.
Jess: I realized that would be a problem for me a few years ago. So that’s partly why I stopped being an operating CEO. I had this conflict — I know I’ll create more value for my companies, but I also know I’m going to get more flak. I’m sure this video will not help with that at all. But I defend it. It’s a practical matter.
Sam: I love that. Unapologetic.
Jess’s Background: From Inaro to Nine-Figure Co-Founder [00:06:00]
Sam: Enough about the private jet. What I want to talk to you about is what you’re great at — ideas and coming up with new businesses. So the track record: you’ve been an operating CEO. You started a company called Inaro when you were really young. How old were you?
Jess: I was 19 when I started. I knew absolutely nothing.
Sam: And then you built that up and started a bunch of other companies. Several of them are nine-figure valuation businesses. You mentioned you have no unicorns under your belt?
Jess: That’s a big insecurity of mine right now — I’m going to be super honest about it. I don’t have a single unicorn. But if you add them all up, I’ve got multiple unicorns worth. So that became my strategy. I’m really not good at building unicorns, but I’m really good at coming up with smaller businesses.
Sam: A barn full of horses.
Jess: Yeah, a barn full of horses. I think we just coined something there.
Sam: That was all you. Good work.
Jess: If I could just raise less VC money and create more companies — not directly operating 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. Miserable. So miserable and so stressed out. And they don’t have the ability to live an amazing lifestyle because of all the optics stuff you talked about. They own a much smaller percentage too. A lot of my unicorn CEO friends own like 5% of a billion-dollar company. That’s a remarkable amount of money, but you know.
Sam: Yeah, totally.
Jess: I’m in it for the lifestyle, not the — you just have to decide what you’re in it for and be honest. There are other people in it for the impact. That’s dope — they should do that, they should save the world. I personally don’t want to do that with my time. I want to indulge my curiosities, have fun conversations, and enjoy my life with my kids. That’s my gold standard.
Sam: So your story is: 19 years old, start Inaro, run and grow it, then transition from operating to your own holdco where you’re incubating companies. You said in the last four years you’ve co-founded companies each worth over $100 million.
Jess: 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, got some early funding. On some I’m still really active; on others I’m just a significant shareholder.
The Idea Hopper: Jess’s Process for Finding Business Ideas [00:10:30]
Sam: I want to ask you about your idea process. Let’s talk about how you get ideas to start these companies, and then what are some ideas right now you’re excited about.
Jess: I’ll talk about process first. I love Y Combinator’s Request for Startups — it’s a list of a hundred business ideas where they say, “If you build this, we’re more likely to fund you.” When I was coming up with ideas for businesses like Inaro, that list was the inspiration.
Jess: 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. That’s really important as a first-time founder. You need more leg room. Another criteria was: I can pseudo-bootstrap this — raise some angel money, but I don’t need to raise $100 million. I wanted recurring revenue, something sticky, a must-have.
Jess: So I literally went through every single idea on the Y Combinator list and ranked them based on those three criteria. Business, accounting, and tax management came out best for my criteria. And my process from there — I go online, I scrape ideas, I’ve gone to Reddit to look for ideas, I have one-on-one lunches and dinners with people where I just say, “Hey, what ideas are you exploring?” and we just 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 myself. That’s never worked.
Sam: Okay. So you had this thing on your phone — this idea database, like 300 ideas. And you promised you’d show some of them today, even though these might be things you still go do.
Jess: I think I might still do some of these. It’s called the Idea Hopper. Let me pull it up on my phone real quick.
Sam: Should we start with the ones you teased before — the Doge-as-a-Service one?
Jess: Yeah, I like this one. So, very trendy right now: Doge-as-a-Service for companies. Explain — most companies have so much waste. You have people who barely show up or they’re phoning it in. I have friends who say, “Yeah, my husband quiet quit his job. He’s working two hours a day and no one’s tracking it.” Those are the people you want to get rid of.
Jess: What if you could create a software platform that tracks who’s actually on Slack, who’s actually emailing, who’s actually using their computer — and if not, they’re fired? A team of consultants plus AI. I also thought if you’re selling to enterprise, you could sell this to consulting firms like McKinsey and say, “Hey, you guys can offer this to the CFO. We can demonstrate we’ll save you hundreds of millions of dollars. You’ll pay us only $20 million, and AI did all the work.”
Sam: That’s actually pretty interesting. I don’t think enough tech teams build tools for the consultants who have already done the sale. McKinsey is amazing at relationships — they’re on retainer, getting paid millions a year. If you can sell them a tool that either helps them land and expand that contract or saves overhead in executing it, that’s going to be pretty valuable. If I was building AI right now, I would not be trying to figure out go-to-market myself. I’d just sell it to consultants who already have the go-to-market done.
Jess: Exactly. And that’s one of my ideas I’m actively exploring — here I am sharing it with everyone.
Idea #2: Vertical Agents-as-a-Service [00:17:00]
Sam: You’re not afraid to share ideas?
Jess: No, I’m super afraid to share ideas. But you just got me really comfortable. This is an idea I’ve been playing around with for a few months and I really like it a lot. I didn’t want to be one of those people who said, “Okay, here are my shittiest ideas. Now you go do them.” That would be really lame.
Sam: All right, what else you got?
Jess: Okay, another idea: everyone says SaaS is dead, agents are the new thing. What if you could build a vertical agent-as-a-service for an industry? Build a library of agents for dental offices, or auto mechanics, or clothing manufacturers or distributors. There are all these industries that need their own very unique library of agents to automate their tasks, and you can go really deep there.
Jess: This is more of a thematic business area. We’re going to see thousands of businesses doing this. You don’t even have to build the agent — somebody’s already building an agent for appointment booking. What you used to have to pay a receptionist to do, AI can now do fully. So horizontal companies are selling the voice agent for any industry. The problem is you still have to do a lot of fine-tuning for, say, a dentist. So what if you’re a company that finds all these off-the-shelf tools, builds your own agents, plugs them all in, and tunes them just for dentists? Plug-and-play. I’m a dental office. I use your company. It has a hundred different pieces of AI already baked into my workflow.
Sam: I like that. And you should do this for an industry you actually know.
Jess: The more boring, the better. That’s the Constellation Software model. You know, we invested in this company called Shop Genie — vertical SaaS for auto repair shops. They built a tool just for them, got 3,000–4,000 auto repair shops in about a year. And — this is great — I was like, “Dude, how did you get so many shops?” He’s like, “There’s this guy who’s like the Kardashian of auto repair shops and he vouched for us.” The guy makes like $20 million a year as the biggest influencer to other auto repair shop owners. Wild.
Sam: So what they did was give him this tool — booking appointments, text message follow-ups — and what you’re saying is instead of vertical SaaS, it’s going to be vertical AaaS. As-a-service. Vertical ass.
Jess: I love it. And the more random the better. Marine shipping, resource mining — Constellation is going to be acquiring and rolling up these vertical AaaS companies in the next few years.
Cargo Ship Coating — Finding Ideas from Dinner Conversations [00:22:00]
Sam: What was the marine shipping cargo ship idea you were telling me about?
Jess: The idea was: coating for cargo ships. Like the paint coating. But to make it more efficient so that these ships could go even a few knots faster. That saves a ton of money on fuel, and you don’t need to take the ships out of the water as often to recoat them. Could be millions, if not tens of millions of dollars over a decade for an entire fleet. Totally random idea. I got it from having dinner with someone who was playing around with this many years ago but didn’t have the money to proceed.
Sam: Where who the heck even thinks about cargo ship coating? Not me. So when you have an idea like that — what are you good at? Are you a good spotter?
Jess: I’m good at initiating conversations with people who are likely to have ideas, or have access to ideas. My buddy James Crier has this great phrase — he says, “You want to turn yourself into an API.” A website has an API that says, “Here’s what I can offer you, here’s what I want in return.” You’ve kind of made your API: I’m always interested in hearing interesting, weird, off-the-beaten-path ideas. So when I hear one, I think, “Oh, Jess would like this.”
Jess: And in return, your API is like — I’m trying to recruit a CEO, and I know Jess has done that a bunch of times. She’ll reduce my error rate and make me go faster. Or if I have an idea, she’s really good at fleshing it out over lunch, riffing on it, and being motivated to push the ball forward.
Sam: Yeah.
Jess: I get people calling me all the time: “Hey, Jess, you got five minutes? I have this random idea, would you build this with me or fund it?” Multiple times a week. It’s like what Warren Buffett did — he just got the word out: “Hey, I’m buying businesses. Call me if you’re ready to sell.” I’m doing the same thing with ideas.
Sam: My business partner Ben — his API is two things. One, he always knows a guy. Always. “Do you know anybody?” “I know a guy who knows a guy.” And the second thing: people just text Ben when something good happens in their life. We just closed this big deal — they haven’t announced it — and he’s not even that close to them. But I realize I do the same thing because he’s somebody who makes you feel good when you win. No envy. He’s not going to try to take anything from you. Genuinely pumped.
Sam: Because of that, he gets this wealth of inbound from people who are winning. Which is also great for us for investing — “Oh wow, these guys are doing really well. Do they need more capital?” That’s a superpower. And it’s not a skill you could learn in school. Nobody would even tell you that’s a thing. But you’re going to build generational wealth off that.
Jess: Yeah, that’s well said. I think it’s equally important to know what we’re bad at. I realized I’m not the best operating CEO — that’s just not my forte. And after I came to peace with that, I was able to say, “Okay, I’m going to come up with ideas, recruit great teams, and empower them.” That’s what I’m going to figure out how to be great at.
Idea #3: Holy Health — Insurance Access for Small Providers [00:27:30]
Sam: Let’s do more ideas.
Jess: Okay, I have this other idea. The code name is Holy Health. I came up with it because I heard of another business that was minting like tens of millions in EBITDA within 36 months. All they did was help one niche of medical provider get access to insurance. So I did some research — plugged it into GPT — and realized there are so many other types of providers like chiropractors or physical therapists who can technically get insurance reimbursement, but they’re so small they don’t have the scale to negotiate with an insurance company.
Sam: So they need to band together?
Jess: Both — they don’t have the time or the skill. If you band them together, they can get some reimbursement. Then you create agents-as-a-service to support them, create more lock-in, and help them with customer acquisition. The full stack. This other company did that for one of these verticals. I’m like, “Oh man, that’s a great idea. Could I do something adjacent that’s not copying them but uses a similar blueprint in a different space?”
Sam: So you get that idea — you call it a clue. And before you even get to that, I want to ask: what is your information diet? Because you’re getting ideas that I don’t hear about. You’re doing something different.
Jess: None of these ideas come from reading a blog post or watching a podcast. All of them come from in-person conversations. I think a lot of people are lazy — they just want to stare at their computer. Nothing good comes from doing that. You have to get out of the building. And when you’re talking to people, I’m not asking them for a business idea. I’m asking them, “What’s the most interesting, exotic business that’s minting cash that you’ve seen recently?” I’m asking for an existing thing they’ve seen. Why is it working? What’s the secret sauce? Why hasn’t anyone copied them yet? And then you’re filtering in real time: Is the secret sauce replicable? Does it take $100 million of VC, or could you bootstrap it? Can AI replace this in 36 months? That’s a new risk factor in my criteria now.
Sam: So you get the clue from the conversation, you filter mentally right there. Then you get excited about the idea and you give it a code name. Why does everything need a code name?
Jess: It makes it feel psychologically real. And it gives me something to remind me of the substance of the idea. So I’ll throw the idea into ChatGPT and say, “Give me 20 potential names for this idea.” Pick one. That’s the code name. Then it goes in the Idea Hopper.
Sam: And I saw that the CEO of Microsoft was on a podcast recently and had this great line: “My new workflow is think with AI, then work with my co-workers.” Not AI replacing your co-workers — AI for thinking and sparring to get clarity, then going to work with humans after that.
Jess: Sounds like we’re doing a similar thing. And what we’re trying to do is have all of our meetings recorded — even in-person, we just turn on Granola. And we’re going to feed that into creating digital twins of all of us, then have basically thousands of versions of ourselves brainstorming and sparring with each other to refine ideas. Like those chess arenas where they train AI to just compete until there’s a winning strategy.
Sam: How would you actually do the digital twin thing?
Jess: There’s so much public content for my team members. And I’m making sure they record every single interaction in the company. Once you have transcripts, you can just feed that into any LLM. It’s going to do a pretty good job.
Sam: Dude, people are using my voice in ads all the time now. Like how do I sue you? I don’t even know who you are. But I’m working on it — I’m telling AI to figure out how to find these people.
Jess: Writing style is the other one. People just put in ChatGPT “write this in the style of” and because you’ve written a lot of content publicly, it’s not quite you but it’s like — that’s 18 months away from being better than me. We might need a safe word. Is it human Shaan or AI Shaan?
Sam: Yeah, we’re going to need a code word. But it’s exciting.
Weekly R&D Meetings — Advancing Ideas [00:35:00]
Sam: So you were telling me about your process. You get excited about the idea, you have the code name, you have a meeting with your team. What are you trying to do in that meeting?
Jess: Every week we have an R&D team meeting where we talk about the ideas we’re playing with. The problem with Holy Health was we just had too many ideas. We have hundreds of them and we try to work on too many at the same time. So then you don’t really advance any idea forward enough between meetings and you lose excitement. The new rule is we’re only going to have two ideas at a time, and we’re going to take them all the way until they’re busted before we bring in another one.
Sam: What do you do in that meeting?
Jess: Anyone can pitch. It’s not just me — everyone usually has different ideas. And it’s like, “Hey, here’s an AI-defensible idea. Here’s why it’s a Maui idea.” We have a common understanding of what a Maui idea is.
Sam: Which is roughly what?
Jess: An idea that can cash flow, doesn’t require a lot of outside funding, we could fund it ourselves, and it’s boring and complicated enough where random people are not going to copy us easily. Those are Maui ideas. And that’s what I’d encourage anyone to do — if you’re an auto mechanic expert, that might be your theme of ideas.
Sam: And where do you leave that meeting?
Jess: We get very specific about what we’re going to get done between now and next week. Person A, you’re doing these five things. Person B, you’re doing these five things. For Holy Health, the next step was: let’s just call some chiropractors and figure out who accepts insurance and who doesn’t and why. And psychologically — are you trying to disqualify the idea or qualify it?
Sam: What’s the mindset?
Jess: Neither extreme. We’re not married to the idea. We’re holding it very loosely. We might hear an interesting insight from a chiropractor that says your idea is okay, but what would make it really good is if you also added AI agents to automate away my receptionist and my customer acquisition. Those are the insights we’re looking for to manufacture an upgraded version of the idea. We assume the first version is terrible and it’s going to go through like 10 pivots — which is almost always the case. And if you don’t have that attitude, you’re basically holding on to bronze when someone’s handing you gold.
Ideas Versus Execution: The Great Debate [00:39:00]
Sam: 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: I think it’s BS. Some of the worst advice I’ve ever heard.
Sam: What’s your take?
Jess: Ideas are really freaking important, and if you have the wrong idea, even a great team is screwed. I modified my thinking on this when I was a scout for Sequoia Capital for many years. They would show us these great ideas with amazing traction, especially in consumer internet, and ask us: would you invest on this memo, yes or no? We’d vote, and then they’d say, “Here’s what happened to that company.” It ended up being a zero. Even with the best team. The idea was still garbage.
Jess: They were training you on historical memos.
Sam: Wow. That’s incredible.
Jess: Even if early traction was good and the team looked great — 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 holds the consumer in? That’s where these ideas would lose steam and die. So, yeah — ideas super important. They’re both really important. But to say “ideas are a dime a dozen” — like, it’s not just the idea, it’s the whole thinking about the business.
Jess: Doing the calls, meeting with chiropractors or auto mechanics in person, really figuring out these juicy tidbits you’re not going to find by sending out a stupid survey or asking ChatGPT what problems chiropractors have. That helps you build an interview script. But then you have to show up. When I was building Inaro, I would go to Yelp and call these CPAs and say, “Hey, I’m a 19-year-old college kid. I know nothing about business. I want to do something to help accountants. Can I come by, buy you lunch, and ask you some questions for 15 minutes?” And then you show up — they’re not going to kick you out after 15 minutes. That turns into two hours.
Jess: We still do that. I’m still on these calls. If you can’t meet in person, do hour-long expert calls. We use GLG for this. There’s also Alpha Sites. You might be paying $800–$1,000 to talk to an expert in a difficult-to-find area, like titanium mining. GLG will find the person, set up the call.
The Starving Crowd and the Holy Health Model [00:44:00]
Sam: The way you talk about ideas and markets reminds me of this story. A marketer goes to a seminar, there are other marketers there, and he says, “Okay, let’s pretend we’re opening up a hot dog stand. I’m a genie. I will give you anything you want.” First person: “Best ingredients, best buns.” He says, “Got it.” Next person: “Location is everything. Corner spot in a high-traffic area.” Each person has a wish. And then one guy says, “I have one thing that will beat all of you.” 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 selling something — the absolute best decision you can make up front is finding a starving, ravenous crowd. Even with decent buns and hot dogs, they’ll buy it instantaneously.
Jess: That’s a great story. It’s about how acute is this problem. One hallmark of a Maui idea is the customer doesn’t have to pay anything. 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 take a cut of that. I love that model — why would you say no? You’re just saying no to more business.
Sam: It’s like those companies that negotiate with all your vendors and take 20% of whatever they save you. If you’re saving nothing today and I save you anything, I’ll take 20%. Okay, go have at it.
Idea #4 and Failures — DivorceF Fund and More [00:46:30]
Sam: You had a couple other ideas. There was a divorce one?
Jess: Yeah. I had so many friends getting divorced. People need an advance on their alimony, or their money gets tied up in divorce proceedings — they’re really rich and successful, but they can’t tap any of their own capital while it’s locked up. What if you could just give them some of their money back? Creative financing around either the window of a divorce or the alimony. We called it DivorceF Fund. Didn’t go forward with that one. People joke about it, but we got more excited about other ideas.
Sam: So let’s talk about failures. One of the things you said to me before was: you like this podcast, but sometimes you listen to people and it sounds like, “I had this idea, it worked, I’m so great.” You wanted to be super honest about things that aren’t working or failures you’ve had. Where do you want to start?
Jess: When I use YouTube and I have all these entrepreneur business podcasts, I spend a lot of time flipping through and thinking, “Man, I’m not doing enough. I’m not good enough.” Even watching your podcast. And I know a lot of these people — these are my friends. I know what they’re secretly struggling with. And they’re not necessarily sharing all of that.
Jess: So 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 called it Cred Boost. Terrible idea in hindsight. I’m embarrassed to share it but I will. The idea was to help you improve your credit and repair it. We had the customer acquisition funnel going but it was high churn, low price point, very high regulation by the FTC. It got compared to credit repair businesses too much. We burned a few hundred thousand bucks experimenting with that.
Jess: Another one — we were going to help veterans of the US military find new jobs and get paid by a program called VRRAP and the GI Bill to do it. All online, virtual, scalable. Veterans signed up enthusiastically. The payment mechanism was this thing called VRRAP — bipartisan acceptance, everyone loved it. But it got approved by the House and never went to the Senate. Money dried up. 18 months later, still not renewed. We tried to pivot to the GI Bill but that requires in-person. And eventually we lost interest.
The Email to Mom at 5:56 AM [00:52:00]
Sam: I want you to read this. This is from a talk you gave — not 2011 as in today, 2011 as in when it hurts.
Jess: I wrote this to my mom and my dad on Saturday, June 4th, 2011 at 5:56 AM. I was up all night. I couldn’t sleep. I was so upset. Subject line: “Kind of sad.”
Jess: “I feel like I’m burning — 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 months or so, and we really need to produce this summer or we’re royally screwed. This was about a year after Y Combinator for me. Anyway, I’m going 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.”
Jess: My mom — she’s an entrepreneur. I absolutely remember that night. I was very upset. I had all these hopes and expectations on myself. Paul Graham was my mentor, and he said, “You’re going to be one of the greatest entrepreneurs of all time — you, Patrick Collison, and Sam Altman.” And I’m still the least successful of that group today. I think about that often.
Sam: That weight was on your shoulders.
Jess: Totally on my shoulders. It still is. My mom called and said, “Hey, 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 slowly crawled out of the hole. Then we grew Inaro to a few hundred employees, profitable, good business — not a unicorn, but it gave me all the training and spiritual training to pursue entrepreneurship and be comfortable with mistakes and failure.
The Entrepreneur’s Inner Monologue [00:56:00]
Sam: At that time — what was the conversation with yourself? Because before the actions come, there’s some inner monologue. Your whole life gets dictated by this tiny little voice in your head that nobody hears — the one telling you how to feel, what to do, where to stand. Training that voice, improving it — that muscle builds in moments like this. Do you remember what you were telling yourself?
Jess: I distinctly remember what the monologue was that whole evening: “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. I’m falling behind. I need to diagnose what went wrong and I need to keep trying. I will not accept or tolerate failure.”
Sam: Were you listening to a song? Where did that come from?
Jess: No — and it wasn’t empowered at all. It was sad. I was thinking that, and because I knew that was my situation, it went from “all right, I need to do all this or I’m screwed” to “I’m really sad and I have to process my emotions. Be honest with myself that I’m struggling. Ask for help.” And I didn’t have a great community back then because as an entrepreneur you want to posture, you want to seem like you’re better than everyone else. But then I realized I could just be honest and I’d still have friends.
Jess: I told all my girlfriends, and it turns out more people were struggling than I realized. More of my Y Combinator batchmates were running out of money. Most of the companies from that batch didn’t make it. People went bankrupt, took normal jobs, eventually started new companies and found success. I still think about that. I still have thoughts like that today. It’s a work in progress.
Sam: I’ve done over 600 of these episodes and you’d have to be sort of stupid at this point not to realize there’s a common mindset among great entrepreneurs. I’ve distilled it down to this: great entrepreneurs are ignorant of the past — because it’s already done, and if you live there you’ll die there. Realistic about the present — like you said, I’m not showing up at my best, I’m not doing the obvious things I should be doing. But it’s not over. Don’t make it worse than it is, don’t make it better than it is. See it as it actually is. And then 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.
Jess: That’s really well articulated. I also remember talking to my business partner and doing a full postmortem. We listed out every single strategic and tactical mistake and what we would do differently. I wish I’d written it down because it was a long list. And even today, yesterday I was talking to one of my colleagues about the number of bad ideas we funded and our process flaws — we would do everything differently going three years back.
Jess: That goes back to what we talked about earlier — Kodawari. What if we bake this into our workflow every week? No matter how good things are, let’s still reflect on the mistakes we made so we can improve and not repeat them. It doesn’t have to wait until you’re about to run out of money.
Sam: No old mistakes. It’s like “no new friends” — it’s “no old mistakes.” You don’t want to keep making the same mistakes again.
Play to Win, Not to Not Lose [01:02:00]
Sam: You said something — “I’m not playing to win.” I was talking to your boyfriend before this and I asked him what’s a Jess-ism — the things you repeat, the things that are like your actual philosophy. He said something like: “Play to win, don’t play not to lose.”
Jess: That came from this story I just shared. One of my problems was I was playing not to lose — I was in a scarcity mindset. When you’re running out of money and you’re in scarcity mindset, there’s research showing your IQ drops significantly during those periods. You’re not going to think outside the box.
Jess: Playing to win means I’m optimistic. I’m delusional about the future. 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.
Sam: What’s an example outside of business where you’re playing to win instead of playing not to lose?
Jess: The airplane is a physical manifestation of that attitude. It’s easy to say, “I’m going to be frugal, let it compound, invest it in my other businesses.” Or, screw it — I’m playing to win here. This is going to manifest way more abundance for me than if I don’t.
Jess: Or — you told me something when we were at lunch that inspired me. You met somebody who threw a great event and you hired this person. You were like, “Here’s a budget. I want to have four events a year in these four cities with the most inspiring, fun people in my world. I’m going to engineer serendipity, luck, fun, cross-pollination of ideas.” I’ve told five people this story.
Sam: I kind of know if I did it I’d have a lot of fun and good things would happen. But you took an almost intentional business capital allocation approach to the luck and fun part of your life. Most people leave that untouched. Luck and fun is just something that either happens or doesn’t. You used almost stone-cold business thinking because you wanted to have fun and meet cool people.
Jess: I also had this friend who hated her private equity job and really wanted an excuse to leave. So I was able to present her with this vision: four events a year with the most successful entrepreneurs and investors I know. We’re launching the first one literally today — that’s exactly where I’m flying after we’re done.
Jess: The vision is a summer thing, a fall thing, et cetera. But it’s expensive. So she and I decided she would find other work, other events. I’d set her up with my friends throwing events. She’d charge per event and get paid based on revenue coming in — all variable, not on my payroll. For this event, I called a bunch of friends and said, “You got to pay something because I have hard costs.” They paid in, and she only paid herself after there was a profit.
Jess: You could get creative about this. For the ideas we talked about earlier, a bunch of my team are on contract. I found them on Upwork. One’s a product management / UI-UX thinker, one is a financial services guy, one was an intern of mine — a kid at UCLA who asked me to speak to his entrepreneur club and then said, “Hey, could I take you to lunch? I want advice. 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 and probably one of my best idea sparring partners. And the event planning person — I met her from the Burning Man community. These people are everywhere around you. They don’t necessarily have a fancy resume, and they’re fun. That’s more important than the resume.
Collecting Eccentric People and Engineering Serendipity [01:10:00]
Sam: I met a friend recently who said something in passing: “Me and my friend, we collect eccentric people.” And I paused on that — “I collect eccentric people.” I don’t do that. What do I collect? So if you said, what are you a collector of?
Jess: For me, I’m a collector of what I call golden nuggets. I can have this conversation with you and I’m just looking for two, three, four things. I don’t need two hours to be perfect. I need three ideas that spark something, three golden nuggets that will change my way of thinking or acting. I’m also a collector of young talent. I see somebody who’s young and hustling or talented in some way, and I’ll really help them out. I want to stay young myself, and I want to connect dots between young people and good opportunities or funding or whatever.
Jess: There’s this interesting idea of figuring out what is it that you collect. Some dudes collect stamps, some collect bugs. What is it that you collect? So for you — what would you say?
Sam: I would say I collect interesting people with out-of-the-box ideas who also like to have fun. That’s the key intersection. You can find interesting people where they’re not fun — very transactional, just in it to make money. But then 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? I’ll just create my own event and bring them there.
Jess: Engineering the serendipity.
Sam: Our buddy Nick Gray does a low-cost version of this. He used to do a renegade museum tour — he loved museums, so his Venn diagram was fun people who are interested in going to a museum on a Friday night. He wasn’t part of the museum, he just took people on a tour because he knew it better than the tour guides. Fun version, a drink outside beforehand. Another thing he does is throw singles events. He was looking to date someone himself, but thought, “Could I do something more creative that not only helps me find someone amazing but maybe helps a bunch of friends find someone amazing too?” Started hosting singles events. Pizza budget. Doesn’t have to be fancy.
Sam: Just taking that intensity to engineering serendipity — I kind of love that.
What Jess Is Nerding Out On: Cancer, Longevity, and Bio-Electricity [01:15:30]
Sam: Before we leave — what are you currently nerding out on?
Jess: I’ve been spending a lot of time thinking about cancer and oncology. Longevity. We’re still funding a lot of research with Mike Levin, who’s my favorite scientist of all time — the bio-electricity ninja.
Jess: 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. Stage four lung cancer. And this keeps happening — every year or two I lose a friend like that. It’s not necessarily going to make me money or improve my lifestyle, but I just have to nerd out on it.
Sam: Is there exciting progress in cancer oncology right now? A new paradigm or pathway that’s interesting?
Jess: With Mike, he talks about how he’s been able to use bio-electricity to normalize cancer cells. Everyone in the field right now is talking about how do you kill a cancer — chemo, radiation, really painful on the patient. But if you could just normalize cancer and not have to kill it, that’s going to be a lot more comfortable. Make it more benign essentially. Really cool research. He’s got a lot on longevity too — making lab animals live longer.
Sam: How insane is AI for medicine and biology going to be?
Jess: I think it’s going to be amazing, but also a lot harder than people think. AI is coming up with all these ideas, but the bottleneck is still regulatory — FDA, getting a clinical trial together. That’s one area where we’re going to see slower progress than everyone is bragging about. Whereas with everything else we discussed — digital twins, brainstorming ideas — there’s no bottleneck. The only bottleneck is spinning up the computer and us pulling the trigger to fund something. But in health and bio, people’s lives are at stake. It’s going to go slow, unfortunately.
Closing — Where to Find Jess [01:19:30]
Sam: Where should people find you and what should they send you?
Jess: If you have any exotic, out-of-the-box business ideas you want to run by me, shoot me a note. I’m on LinkedIn — just search Jess Ma. I post on my blog there almost every week. Partially using ChatGPT to draft posts, but I still review it. I say, “Hey, write me a blog post that’s 2,950 characters long in my voice about XYZ, and insert these anecdotal stories.” Within two minutes I have a blog post.
Sam: That’s amazing.
Jess: And from the last pod we did, I actually made a bunch of friends. People cold-emailed me and I’m like, “Yeah, I’ll grab lunch with you.” Two people I met from that episode are coming to my retreat.
Sam: That’s a point of pride for us — if somebody comes on this podcast, they should get more inbound messages than from any other podcast they go on. And the people who message should be people you’d actually want to talk to. If we’re doing that, we’ve built the right tribe here. Great community.
Jess: Thanks for having me here.
Sam: Awesome. Well, cheers.
Jess: Cheers.
Sam: All right. Here we go.