Jess Mah built 10+ companies worth a combined $952 million starting from being a high school dropout who ran a server business as a teenager. The conversation covers her journey from Silicon Valley’s unrecognized entrepreneur to biotech investor, her philosophy of “bold science,” wealth management practices, and what Paul Graham told her about the traits common to the most impressive people he’d ever met.
Speakers: Sam Parr (host), Jess Mah (guest, entrepreneur and founder)
Introduction: Why You’ve Never Heard of Jess Mah [00:00:00]
Sam: All right, this is going to be a special episode. I think the best episodes we do are the ones where we highlight a business or a person who is amazing that you’ve never heard of — and that’s what today’s episode is.
Sam: The person we have on is Jess Mah. She has built herself — I don’t know — 10 companies that have combined worth somewhere around $950 million. And not only has she made a bunch of money or been successful in business, she’s just a force of nature. People that I respect think she’s one of the best entrepreneurs in the world. That’s kind of amazing for somebody whose name you don’t know and who you’ve never really seen do interviews.
Sam: Paul Graham, when he met her and she was at YC, put her on the very short list — a couple of people with Sam Altman and a few others — as the most impressive people, the people he thought 30 years from now will have done the most and gone the furthest.
Sam: I was at a dinner — that’s how I met her — and a friend of mine pointed at her and said, “That woman over there is the best entrepreneur I’ve ever met.” He’s lived in Silicon Valley for 15 years. To say that is high praise.
Sam: So I had to have her on the podcast to talk about everything: from her beginning, where she was basically a loser among losers in school — she talks about how not only was she not cool, even in the Computer Club she got bullied and didn’t fit in — to where she is today, building biotech companies doing crazy stuff.
Sam: I asked her, “Were you like a science genius? How did you know to go into this space?” I think there’s a part of all of us that wants to go do the big, bold, crazy, change-the-world thing but we’re afraid. “Who am I to go do that?” At least, that’s a thought I’ve had. And it was kind of amazing to hear her say she felt the same way. She’s like, “I got a C-minus in biology, and now I have a nine-figure biotech company.” That’s crazy — how she approached it, how she met the scientists, how she got the funding, how she talked herself into doing it from rock bottom.
Sam: The other thing in this episode that I think you’re going to like is she talks a lot about the lifestyle and financial stuff that comes from people who are already really successful. She talks about, “Yeah, I just hop on my jet” — she’s very open about it, and I love that. I hate the billionaire who downplays it and pretends like they’re flying coach. I like to hear what people actually do, how they use money to improve their life, how they architect their businesses. She does all of that, and she’s very open about it.
How They Met: First Impressions and Dog Vests [00:05:00]
Sam: All right, good to see you. I want to tell people the story of how we met. It’s not an extravagant story, but it’s one of those things where I would have bet anything that you’re an interesting person just based on the signals.
Sam: My friend told me, “That woman over there is the most impressive entrepreneur I’ve ever met.” And he just said that without me even asking. I was like, “That’s extreme.” He said, “Yeah, she’s extreme.” Next thing I noticed was you had your dog in the restaurant. I was like, “Okay, that’s awesome.” Then I thought, is this a service animal? This is a nice restaurant. And you said, “Yeah,” and you flashed me this FBI-badge-style service dog vest. I was like, “Did you buy that?” You’re like, “Yeah, you can buy it on Amazon for ten bucks.”
Sam: So there’s all these little signals — somebody who rolls by their own rules, my friend telling me you’re one of the most badass people he’s ever met in entrepreneurship, and then you give your intro and you go, “Yeah, I started this thing, inDinero, which I’ve heard of — and now I sit on the board of like 10 companies. We do bold science bets.” And you didn’t even explain it. I was like, “What’s a bold science bet?” You go, “Like curing cancer, but not the typical way — a different path.” You kind of nonchalantly gave me some answer and I was like, “Say no more. I need to get to know this person.”
Sam: That’s my buildup. That’s my first impression. Tell me what it feels like to hear that — because people never tell you their actual first impressions as they remember them.
Jess: That’s amazing. It was super fun to have that dinner and meet you that night. I just had a good feeling we were going to have a fun time. Normally I don’t go out — I’m kind of a loner. I like to be at home and take it easy after work, and it’s a lot to deal with with 10 companies. We’re going to add more companies this next year and I’m trying to figure out where I want to spend my time as an entrepreneur. That’s an ongoing question. But I’ve heard about you, I’ve seen your podcast, you’re famous — so it’s kind of an honor to be friends with you too.
The HoldCo Model and “Bold Science” [00:08:30]
Sam: One thing that’s cool is you have a holdco. If I were going to name some entrepreneurship trends, there’s a personal holdco model becoming popular. But most people doing the personal holdco are doing what I’d call small-boy stuff — like, “I acquire this little SaaS app,” or “I’m buying a plumbing business and rolling them up.” You have a holdco, but yours is all game-changer, go-big-or-go-home bets. I find that really interesting.
Sam: I also think another entrepreneurship trend is doing hard stuff. Elon popularized “you could create the next app and that’s cute, but I’m going to make rockets and electric cars.” Then you have AI and Sam Altman and the cutting-edge science movement. You’re a part of that intersection, and very few people really play that game. So I wanted to learn from you today: why do you play that game, and how do you do it?
Sam: Give people the quick background — how do you introduce yourself when you’re trying to brag a little?
Jess: I’ll be honest, I’m really shy and it’s hard for me to talk about these things, because everyone I meet is so impressive that no matter what, I feel like the dumbest person in the room. But just to catch everyone up: I’m an entrepreneur. I’ve started so many companies. My first company was called inDinero — a financial SaaS company. We do accounting, tax, bill-pay management software and services for businesses. Our customers were companies like Slack, Pinterest, DoorDash, Coinbase. I started that straight out of college.
Jess: I studied computer science at UC Berkeley. When I was a senior, I was running the CS club and I brought in speakers. One of the speakers I brought in was this kid named Sam Altman — he was building a company called Loopt. I said, “Hey Sam, what should I do after college?” He said, “You should do YC.” And he helped review my application, and then the rest is history.
Jess: I did inDinero for 10 years, grew it to a few hundred people, valuation in the hundreds of millions of dollars. But the way I built that business was I didn’t raise traditional venture funding — I didn’t bring in VC capital, only some angel investors. I was able to retain most of the ownership, and it’s a cash-flowing, profitable business to this day.
Jess: There were lots of ups and downs — being weeks away from insolvency multiple times. I always ran things a little too close to the edge, probably because we were undercapitalized. I survived a bunch of near-death experiences with that business. Eventually I realized I didn’t want to be a CEO anymore.
Jess: I grew up with this mindset that you have to be the operator, and if you’re not the CEO and don’t make the company a unicorn, you’re a failure. I Googled the world’s billionaires and thought, “How did these people become billionaires?” Most of them built companies, a lot of them were diversified holding companies, they held on for decades, and many of them weren’t the CEO — they were more like investment managers. Warren Buffett’s a great example. That got me thinking: am I doing this wrong? Am I just listening to Silicon Valley rhetoric pointing me in the wrong direction?
The Turning Point: Loss and Rock Bottom [00:14:00]
Jess: A few years ago I went through a really tough experience. My boyfriend, who I was living with, died very unexpectedly. I was going through a really dark period where I was not able to work. I woke up in the morning super depressed and didn’t want to do anything.
Jess: I thought: what would I do if I was going to die this year? If this was my last year here and I had to make myself happy, what would I do? Running a company was not on the list. So I immediately hired a CEO for inDinero. I had another company I’d started — a litigation fintech company that originates and funds lawsuits. I brought in a friend to run it. And then I’ve started a bunch of other interesting businesses since then.
Jess: I’d rather build quietly, come up with really interesting ideas, find someone to go build them. A good chunk are businesses that just print cash, but a lot of them are bolder. That’s why I got interested in biotech. I thought: what would I do if I wasn’t scared of failure? After my boyfriend died, I thought a lot more about that. I thought, I shouldn’t be scared of trying and failing because I’ve seen rock bottom. My life can’t get any worse than it is today, so I might as well try something.
Sam: That’s an amazing story. “What would I do if I wasn’t afraid of failing” is up there in the pantheon of great questions. I asked myself that same question, and it changed everything. I wouldn’t be doing this podcast if I hadn’t sat down and made a Figma file drawing out a flowchart of my life. I had three paths: start a company, invest, or — and I literally wrote this — “be Tim Ferriss.” And I thought, why don’t I just do that?
Sam: Then I was like, well, what if it doesn’t work? Then I’m just a guy with a podcast. And I thought: am I just not going to do it because I might fail? So I had that talk with myself. The most important talks are not with mentors, they’re with yourself. And it sounds like you had one of those too. Can you talk more about that conversation?
The Beginner Mindset and Overcoming Insecurity [00:19:00]
Jess: A big question I asked myself was: how will I deal with the insecurity of feeling like a beginner and being terrible at something — despite the fact that for the past 10 years I got pretty good at being a CEO? I’m sure you felt the same way. You were a great entrepreneur and then you were getting into building content and interviewing people. That’s a whole new skill set you had to become good at. For a while it’s awkward. I’m sure your first videos were not nearly as good as your recent ones.
Jess: So a lot of the self-talk is: “Oh my God, I didn’t do a good job. I still don’t know what I’m doing. People don’t take me seriously. Do I even take myself seriously?” But meditating on that and thinking, “You know what, it doesn’t matter, because I’m having a great time, I’m learning a lot, and the outcome will work itself out” — that’s how I deal with it.
Sam: Being okay with being a beginner — that mental prep is important. It’s one thing to say “what would I do if I wasn’t afraid?” but the fear is still going to be there. Fear of being wrong, failing, looking dumb. So that beginner conversation is important. “If I go into this, I’m going to start as a complete beginner. I’m going to get better over time because I’m good at learning. In six months to a year I’ll be competent at this.”
Sam: It reminds me of a story I’ve told on the pod before — Moiz Ali, who created Native deodorant. When he told his friends, they were like, “Cool, random — do you even know anything about deodorant?” He said, “Today I know nothing about deodorant. But in six months I’ll know everything I need to know.” That idea of writing yourself a blank check is really important.
Sam: And you told me that story yourself. I put you on a pedestal — I was like, “You’re doing this because you’re smarter than the rest of us.” And you said, “No. I got a C in biology. I hired a tutor as an adult to learn about this. I watched TED talks and podcasts. I flew out and met the scientists.” Just normal blocking and tackling.
Jess: I still have major insecurities about this. In fact, last night I had my recurring nightmare — getting C’s in school and being very close to flunking and having to repeat a grade. I got C’s in bio in high school. I thought I could do a lot of things with my life, but anything related to biology was not one of them.
Jess: Then when I was on the cover of Inc. Magazine, the woman who was on the cover a month before me was Elizabeth Holmes. When Theranos went under and the whole thing happened, I thought: bio is really hard. I’d be so paranoid and scared. The last woman who tried to do something in biotech got destroyed by the media and is now in prison — that’s not a great inspiration. I had to overcome that, and eventually I decided: you know what, I want to give it a try. So I hired a biology tutor, digested all the information, and brought in people who’d been running biotech companies. That’s really how I operate — just bringing in people smarter than I am.
What Would You Do If You Were a Billionaire? [00:25:30]
Sam: Another question I ask a lot of my best friends: what would you do if you were a billionaire, if you had a billion in hard cash and weren’t allowed to do what you’re doing today?
Jess: I’ll tell a quick story first. When we got acquired by Twitch, first day I thought, “Let me go find my people.” I was in a company of 2,000 and I was like, “Where are the entrepreneurs at?” There was a founder who’d been acquired a few years earlier for around a hundred million, still working there. I took him to lunch and said, “Why are you still here?”
Jess: He said, “It’s going great, we’re working on stuff.” I said, “But is this what you want to do? You’re four years in.” I thought, there’s no way I want to be here in three or four years. So I asked him differently: “If I put a hundred million in your bank account tomorrow, would you show up to work?” He said, “Well, no — I’d buy a ranch, I’d be outside with my four kids, but on the side I’d be building this type of project.” I said, “Okay, so that’s what you really want to do. Let’s at least be honest about it.”
Sam: The most important talks are with yourself. And that question helps expose the gap between what you say you want and what you’d actually do.
Jess: Exactly. And I think a lot of us have so many things we want to create in the world, but it’s dangerous to wait. Life priorities change. I see this with many of my friends — they get married, have kids, get comfortable, they’re building their ridiculous house, and life goes by. It stays a dream. I just couldn’t allow that to happen to myself.
Sam: “It’s dangerous to wait” — I think most people feel like it’d be risky to go do it, and they vastly underestimate the risk of waiting. Because by waiting, you actually get further away from the goal. You fill the space with other activities, other responsibilities. You train yourself not to take action on the things you actually want.
Sam: I remember at Twitch, my new boss came in — Dan, now the CEO — and in our one-on-one he asked me about my career goals. I thought: I can either lie to this guy and say I can’t wait to get promoted from L7 to L8, or I can tell the truth. So I told the truth. I said, “I can’t wait to go build another thing. I don’t see myself here long-term.” He didn’t flinch. He said, “Okay, now that I know that — what do you really want to do?” And I started giving him these pre-requisite steps, and he said, “I’m not really a fan of wanting to do X and doing A, B, and C first. You’re better off just trying to do X.” I was like, you’re right. I was bullshitting myself.
Resourcefulness as the Master Skill [00:33:00]
Sam: It reminded me of that Tony Robbins TED Talk — have you seen it? He goes on stage and says, “I’ve spent my whole life studying what stops people from having what they want.” People in the crowd start saying things like, “I don’t have the time,” “I don’t have the skills.” And Al Gore is there — this was right after he lost the presidential race — and someone’s voice says, “I didn’t have enough Supreme Court Justices.” Tony Robbins goes, “What? Who’s — oh, Al Gore’s here.”
Sam: And then Robbins basically slaps all their answers. He says everything they listed is a resource they lacked — money, time, capital, Supreme Court Justices. He says the only thing you actually need is resourcefulness. That is the master skill. The ability to go get the resources you need when you need them. If you are motivated enough, charismatic enough, playful enough, convincing enough, determined enough — can you not get everything you want? Is there really anything outside of you?
Jess: That’s exactly what I’m saying with the manifestation studio concept. Instead of “do I have what it takes, financially or skill-wise” — you create the time by hiring better experts to do the work, and you manufacture the money by raising it. In my case I’ve got a multi-person investor relations team with connections to tons of billionaires and family offices. That’s going to be a four-person capability within the next year. So instead of a holdco, let’s call it a manifestation studio.
The Science of the Future: What’s Coming [00:37:30]
Sam: Let’s talk about crazy science dreams. You have ideas, you’re talking to scientists all the time. What are some things in the future that you’re excited about that aren’t just pipe dreams — where there might actually be a pathway?
Jess: Test-tube babies — I actually think that is very viable. I know of several scientists doing portions of this. For example, taking genetic material from someone who wants to be the mother — not the father — and creating an egg out of it. I think we’ll see that within the next five years. The artificial embryo, Avatar-style, is harder. I’ve met scientists who’ve gotten to maybe six weeks before the whole thing falls apart, but it will get better. The implications are huge. Imagine women not having to deal with egg extraction if they’re having trouble conceiving.
Jess: What’s also realistic: extending our lives by 30%. We need to be prepared to live to 120 or longer. Right now the ceiling in our heads is 90. We’re not thinking about the exponential rate of change. I’m talking to a lot of longevity scientists, I’m seeing the data — it’s compelling.
Sam: What’s the short version of how we get that extra 30%? Drugs, diet, reversing aging, young blood?
Jess: Probably a combination. And all these projects fall under what I call “bold science.”
Sam: Define that.
Jess: There are so many companies working on very incremental stuff — extend your lifespan by three to six months, which means more time in the hospital taking chemo drugs. I’d rather go to hospice than prolong my suffering. What if instead of patching the problem — putting a bandage on a gunshot wound — you could get to the root cause and reverse cancer?
Jess: Right now everything in cancer is about killing cancer cells through chemo, radiation, surgery, CAR-T therapies. But what if killing cancer is the wrong approach? What if cancer happens because your cells are trying to protect themselves, and instead of killing them, you could rehabilitate them and get them to integrate back in with their surroundings? We’re working on a company around that. That’s what I mean by bold science — a complete step change, a different point of view on the problem.
Getting on the Plane [00:43:00]
Sam: One thing you said that I liked when we were talking before — you said, “I get on the plane every time.” What do you mean by that?
Jess: There’s a successful entrepreneur I know who lives in Vegas. I live in LA. I just said, “Hey, tell me a time and place on Sunday or Monday and I will fly to Vegas just for the meeting and then fly home.” Tuesday, same thing — Patrick Collison from Stripe asked me to hang out, and I just got on my jet and flew there for dinner and flew back. You don’t need a jet for this. Buy a Southwest ticket. Get creative about it.
Jess: I had Delian Asparouhov do this for me. He literally flew in from South America and went straight from the airport to dinner with me — the first time we’d ever had a one-on-one. It really made an impression. I thought: this guy went out of his way to do this. He is a hundred times more important than I am, and he did that. It made me want to be friends with this person.
Jess: And I have another billionaire I hit it off with at a group dinner. We had two hours and he just talked about the meaning of life, all his regrets, all the things he’d do differently. He said, “Everyone wants me for my money but no one asks me these questions.” I said, “Where do you live? I’ll visit you.” He said, “The Bahamas.” I said, “Great, I’m visiting you.” We booked it. I’m seeing him for dinner in three weeks, and I’m going just to see him.
Sam: My uncle calls it “belly to belly.” He says you’ve got to meet belly to belly. And it’s not just face-to-face — it’s: I am flying five hours out of my way to see you. There’s no better signal.
Jess: A zoom call is a one. An in-person visit is a ten. That’s how wide the delta is.
Sam: And this only works if you’re already successful, right? Like people want to meet you because you’ve made it?
Jess: I was getting meetings like this when I was 16 and knew nothing. I cold-emailed Justin and Emmett from Justin.tv. I said, “Hey, I’m this idiot 16-year-old. I think you are brilliant and I’m willing to fly to you. I want to be a fly on your shoulder and see you do your work.” And if you pull up the Justin.tv archives, you’ll actually see me driving him around San Francisco and going to a poker game with him — all because I was willing to do that. Mark Benioff replied to me too. I was a 16-year-old nobody.
Spotting Talent and Early Life: The Server Business [00:50:00]
Sam: I think one of the valuable things in life is to become a good evaluator of people — like an NBA general manager spotting talent. When I met you, I really felt like this might be someone operating at a different level. So I asked you: if I met you when you were 13 years old, what would I have seen? Would there have been any signals?
Sam: On my side, I was a totally unimpressive 13-year-old. There were no signals. But I’ve met a lot of people who, as teenagers, were flipping things on eBay or building a product. You have an amazing backstory.
Jess: When I was 13, I started a dedicated server and colocation business because that’s what I thought you did in high school. I don’t know why, but I thought it was kind of normal. I found it on internet forums. I thought: this is a commodity business, but I could probably figure out how to do it and make a few bucks to offset my gaming server expenses. That was the goal — just make $10,000 a year so I didn’t have to work at the mall or rake leaves.
Sam: Did you know somebody else doing it? Why would you think that was normal?
Jess: I genuinely don’t know. I just found it on forums and thought, “Okay, I can do this.”
Sam: Were you cool in school? Popular? Smart? Who were you?
Jess: Total geek loser. I had no friends. I went to the Computer Club at my high school — all the nerds who also had no other friends, so they had to be friends with each other. They were making fun of me and bullying me. I was literally at the bottom of the bottom totem pole. I thought, I have to get out of here as soon as possible.
Jess: So I ended up dropping out of high school halfway through my sophomore year. But I got into this really cool program called Simon’s Rock College — going to college early. That really saved me. I was bored in high school, I wasn’t doing well, I had no friends, I couldn’t relate to anyone. All the other girls and guys were interested in things I had no interest in.
Sam: So when you said you’d love to create a school for people like us — I immediately thought, I want to create that school too. Let’s go meet and put together a game plan for what that would look like without having to wait until we’re sitting on a billion in cash.
Jess: Yes. Done. Belly to belly, booked.
Sam: Tell me about the server business. Did you make the 10 grand?
Jess: I was making hundreds of thousands of dollars a year off of it. I was making more money than my teacher. I remember in biology class at 8 AM, I can’t pay attention because I’m answering customer service and sales emails. I had five hours of sleep because I was up until 3 AM. And to make myself feel better I thought, well, at least I’m making more money than my biology teacher while I’m asleep. Moral victory.
What Jess Learned from Justin Kan, Benioff, and YC [00:58:00]
Sam: When you were meeting Justin Kan, Mark Benioff, all these YC founders — did you learn anything? Did any stories stick with you?
Jess: What I got out of it was: there are other people like me who are a little crazy, who are willing to approach life and entrepreneurship in an unconventional way, who are willing to do the hard things. When I saw Justin, when I saw Steve Huffman at Reddit, I realized I don’t need to wait until I’m older to start doing this. I also don’t need to have money or a proven track record first. It was always more about mindset and psychology than tactics.
Billionaire Secrets: Taxes, Advisors, and the Right People [01:01:00]
Sam: I want to get into what you called “billionaire secrets.” You’ve met a bunch of super-rich people and the way they think is a little bit different. One of the things you mentioned was taxes. What’s different about the way the most successful people you know think about money?
Jess: Tax optimization is a really big deal. If half your money is going to Uncle Sam, it’s going to massively impact your compounding. Run a compound interest calculator and see the delta.
Jess: These billionaires employ the best tax strategists in the world. Eventually I said, “Can you introduce me to your tax person?” That person works with 30 other billionaires and has saved them collectively hundreds of billions in taxes. Now I have a whole collection of these intros. I call multiple tax professionals and combine their advice, then merge it together. I think that’s the next level.
Jess: Most people just pick one person and say, “I’ve been working with Betty for 10 years.” Well, Betty doesn’t work with billionaires. Time for a new tax accountant. I literally had this conversation with someone over lunch last week and he texted me right before this call saying, “Oh my God, this is going to make me millions of dollars more over the next few years.”
Sam: I feel like if I talk to another tax person or lawyer, I’m cheating on mine. And that’s such a dumb way to think about it. It’s your job to get the best opinion possible. They may also not specialize in the newer things you’re doing — real estate deals, M&A. You should be talking to people who really understand that.
Jess: Multiple opinions are better than one, and specialties matter. Also, the person doing your tax strategy tends to give you most of their strategic thinking in year one, and then you just become the client they stamp every year. So you need to keep dating in order to have fresh ideas coming in.
Sam: You said people should be spending a certain amount of time on taxes based on what the math tells you, and what they actually spend is less than 0.1%.
Jess: Way less. If taxes impact half your income potentially, and you invest even 5 or 10% of your time this year to finding five amazing tax strategists and getting all their advice — that’s a 100-fold return. It’s the highest-ROI investment you can make. It’s way better than investing in the stock market. And your taxes are always your biggest expense. Even 10% sounds like overkill — that’s 36 days out of the year. You don’t need that much. Even five days in the year to do this gets you a lot.
Health Optimization: Coaching, Nutrition, and Exosome IVs [01:10:00]
Sam: What about your psychology and mindset — do you do anything to make sure the little voice in your head is saying the right stuff?
Jess: I have two coaches I talk with each month. I think of it like going to the gym or taking a shower — even if I think I’m happy or in a good mindset, I still go to make sure my head is screwed on properly. Costs a ton of money, but it pays for itself right away.
Jess: I also have my CEO group — YPO, Young Presidents’ Organization. You think you don’t have time for it, but you don’t have time not to.
Jess: Health stuff too. What if you could optimize through better nutrition and nootropics and IVs — not just your longevity, but your mental acuity? I work with five concierge doctors to come up with my own custom plan. I’m actually going to put something together I can share with my friends so anyone I care about can get on the same program. It includes supplements, custom compounding into just two pills. And then doing exosome IVs once a quarter.
Sam: What is that — exosome IVs?
Jess: The science is still a little up in the air, so I want to be transparent about that. It’s not necessarily a fountain of youth, but the belief is that if you’re bringing in stem cells through an IV, it will help lower your biological age, give you more energy, and help with autophagy — your body’s ability to clear out old and dying cells. More energy means more brain power, more brain power means more ability to create things in the world. And if you could improve your mental function and energy by 25% — is that worth maybe $20,000 to $25,000 a year? You don’t need to do a Brian Johnson where you’re spending a million dollars a year. You can get 80% of the results for a fraction of the cost.
Sam: Good. I’m going to hit you up for some recommendations.
Jess: I’ll eventually pull all this feedback together and share it publicly for free, so you guys don’t need to pay for your own concierge doctor. It’s not that personalized — 90% of what I’m doing anyone else should just be able to do on their own.
Sam: Give me the quick rundown from most impactful to more fringe.
Jess: Honestly, it’s hard to know exactly where the impact is. I’m a fan of berberine — I’m sure people have talked about that on your pod before. I’m a fan of adding in a whole list of supplements and nootropics that I can publish for you. Having them all compounded into a few compact pills makes it easier. I have a friend who has his own compounding setup, so I get it at cost, and my plan is to work with him so my friends can get what I take without a huge markup. And then peptides for the more advanced stuff — some are injectable, so consult a doctor on those. I’d benchmark using the TruDiagnostics biological age test, before, during, and after, to see how you’re doing.
The Manifestation Studio: Being Non-Operational [01:18:00]
Sam: What are the other categories of billionaire secrets?
Jess: I think those are the big ones. The other one is what you talked about — being non-operational. Create a vehicle that creates all your other vehicles. Every project needs a vision, capital, and an operator. My job is to be able to create those packages. That’s the higher-leverage way to operate — not going every day and turning the crank myself.
Sam: And billionaires have a different mindset about buying expensive things, right? You think they waste money on boats and planes, but a lot of it is taxes.
Jess: I have a friend buying a $30 million yacht right now and he found a way to get a $30 million write-off. He’s going to charter it out for a bit, and the bank will finance 80% of it — he’s only putting 20% down. Net-net, it’s cash-flow positive for him to buy the yacht. The operational costs are largely offset by the charter.
Jess: People do this with planes too. I did this with my airplane. I had a bigger write-off from buying the airplane than what I put down in cash. Let’s say you buy a plane for $5 million and the bank finances most of it, so you put a million down. You could get a $5 million year-one write-off — that was accelerated bonus depreciation. The rules are changing — this year it’s only 80% you can deduct upfront, then 60%, then 40%, then 20% over subsequent years. But the tax benefit is still real, and if it enables you to do more of what you want, there’s that incalculable benefit on top of it.
Sam: And the rare-car thing — I was surprised to learn there’s a whole class of really expensive cars where you basically get to drive for free, because they hold or increase in value.
Jess: Exactly. People I know with exotic cars have driven them for a year and sold them for the same cost or more, because other people want access but don’t have the relationship with the manufacturer or weren’t willing to wait four years on the waiting list. Once you start to play, it’s like a snowball — you use money to buy something that makes you more efficient, that’s a tax write-off, and that holds value. All those gains accumulate.
Sam: Some people hate that and think it’s unfair. I don’t give a moral opinion either way. You can choose to benefit from it, ignore it, or be upset about it. You have choices.
Jess: What’s cool is people can learn about mindset and how to get there — that’s what you’re doing with your podcast. Money is this taboo thing. Nobody’s supposed to share what they make, what they invest, what they do with taxes. It’s a real shame, because it means it’s very hard to learn. Until someone cracks it open and starts sharing, then more people start sharing, then you start to learn faster.
Conor McGregor and the Bitterness vs. Inspiration Choice [01:30:00]
Sam: There’s this Conor McGregor quote where he talks about going from plumber to highest-paid athlete in five years. There were guys who’d been fighting in cage matches for $20,000, paying for their own flights and hotels, left with two grand after medical bills, and they were very bitter at McGregor. Someone asked him in an interview, “Do you ever think about toning it down?” And he said, “No. Some people see this and they take inspiration — that’s who I was. I saw people doing things and I took inspiration. Other people see things and they get bitterness, and they will end up bitter. It’s not my job to figure out which path they go down.”
Sam: That kind of freed me up to talk about things on this podcast that you’re supposed to downplay. When I was growing up I couldn’t wait to hear that someone had a private chef, or whatever. I don’t feel bad that I don’t have one — it just puts a new thing on my list that would be awesome to work toward.
Jess: I love that. It is difficult to struggle with the feeling of jealousy versus aspiration. But one trick: if you’re surrounded by people who are more successful than you, instead of envying them, interpret it as a good sign. This means more success and more happiness is coming my way, now that I’m able to attract these people into my life.
Jess: I remember having to deal with that when I was a coming-up entrepreneur who knew absolutely nothing, and Drew from Dropbox and Sam Altman were coming to speak to us CS students. The gap felt very wide. But just having them there, saying, “Email us if you have any questions, we’re here for you” — it made it easier to focus on the education instead of the envy.
Sam Altman: What Jess Observed [01:35:00]
Sam: Can I ask you one more thing? Sam Altman is now this extremely interesting public character. Very few people actually know him. You’ve had interactions with him. Can you give me your impressions?
Sam: I remember reading Paul Graham’s essays ten years ago where he said the five most impressive people he’d ever met included Sam Altman — when he was just doing Loopt, no track record. It was just very apparent in meeting him. Did you get that sense?
Jess: I actually had a one-on-one with Paul Graham about 13 years ago. And I asked him: “Who do you think will be the most successful people you’ve ever met — who will that end up being 30 years from now?” Sam was on the list. I’m not going to share who the others were, but they’re all doing extremely well.
Jess: What a question that was, by the way. And I asked Paul: what are the things in common with these people? What do you see? And for him, it was less about intelligence. It goes back to the common theme we’ve had throughout this conversation — grit, being willing to be unconventional, trying different approaches, collecting ideas from multiple fields and merging them together to come up with something better than any single domain expert could. And how they show up and what they’re willing to do to meet the right people.
Jess: That reinforced my wanting to have the policy of just get on the plane. It’s a trait that successful people perceive will lead to you being destined for greatness. I don’t think I’m destined for greatness, but — what if I could manufacture other people thinking I’m destined for greatness? Maybe I’ll create that reality somehow. Eventually it walks like a duck, talks like a duck — hey, it became a duck.
Sam: So those traits: resourcefulness and willingness to make things happen. Collecting ideas from multiple spaces and synthesizing them past what any single domain expert can reach. And wanting to meet the right people, asking the right questions, being willing to go to certain lengths to do it. Did I miss any?
Jess: Just to build on that third one — how do you make yourself interesting enough at a dinner party that they’d want to invite you back? How do you broaden your field of knowledge to be someone a king or president would want to call upon for feedback? Paul Graham has this huge library and has read most of it. He’s just fascinated by so many topics. That left an impression on me: should I just learn about random things that have nothing to do with my day-to-day business? Because they’ll help with that third category.
Sam: I went to a farming conference two years ago — the best conference I’d been to in five years. I’d only been going to tech conferences. Nothing new, same thoughts, same types of people in the same bubble. At this farming conference in Kansas City I was piecing together two ideas — one from tech, one from a farmer I met. That’s actually where we created the Milk Road. The name came from a dairy farmer sitting next to us. If I hadn’t stirred the pot in that exact way, maybe the answer would have been different.
Jess: That’s super cool. And I’d love to download from you what’s on your list of the next areas you want to learn about. For me it’s been bio lately, but I want to broaden it even further.
The Bioelectricity Companies: Mike Levin and Astonishing Labs [01:44:00]
Sam: Give us an example of one of the bio companies you founded — the problem, the solution, the rough stage.
Jess: The high level: I set up a holding company for biotech venture creation centered around a scientist named Mike Levin. If you search his name, he has a TED Talk and a three-and-a-half-hour interview with Lex Fridman that I highly recommend — you will get sucked in.
Jess: Mike got his PhD in genetics at Harvard and then devoted his entire career to proving that genetics are actually not that relevant in the big scheme of things. It’s this other thing — bioelectricity — that dictates how long we live, whether or not we get cancer, how our limbs and body shape form. Genetics are like the hardware layer of biology. He says biology is the software.
Sam: You told me this at that dinner. You said people think DNA says what ends up manifesting — and it turns out that’s not quite right. I went and watched his TED Talk. He talks about how they’re able to grow an arm on an animal’s back, grow a third eye, show all these amazing phenotype outputs without any genetic modification.
Jess: Exactly. When they saw a tadpole growing an eyeball, the bioelectric signature of the cells in that area changed. The question was: what if we create that same bioelectric signature but on another part of the body? Not only does it grow an eyeball there, but it grows a connection to the spinal cord. You don’t have to micromanage biology. If you tried to do that through genome modification, there’d be no way. So logically: genetics are therefore not the end-all be-all.
Jess: I heard about this, it blew my mind. I asked, “Does he have a commercialization partner?” The answer was: it’s still in the lab, and there was no one commercializing it yet. Paul Allen was funding the whole lab, and then Paul Allen tragically passed away and the funding dried up. He needed money, he needed people to help him make it a real biotech company.
Jess: So I met him through a friend. My friend mentioned Mike over lunch and I thought: this is brilliant. Could we fly out and meet Mike next week? I’ll clear my calendar and spend a few days with him. I met Mike, spent some time with him, and realized this is really compelling.
Jess: Then I hired a guy named Tom. Tom had taken a drug called Elosulfase Alpha from lab all the way through FDA approval — full approval — for $16 million, which is absolutely crazy. In the drug world, it normally takes hundreds of millions to get something approved. But his drug actually worked. It was putting patients in full remission — the first eight out of nine patients who would otherwise be dead within months were going into remission. So I brought him in to do due diligence on all of Mike Levin’s science and figure out a strategy for turning these into real biotech companies.
Jess: My contribution: I have 12 people who work with me at my holding company — or whatever you want to call it. For me it’s just an extension of me. If there’s something I want to manifest in the world, I have a team of brilliant people who will figure out how to make it happen.
Sam: So what are you actually building?
Jess: We’ve created several companies under this structure. The first company is called Sju, and it essentially helps overcome drug resistance. Concretely: if you’re taking drugs for leukemia and they’re working, there may come a day when they stop working. When they stop working, there are sometimes no other viable options, which means the patient is going to die — when a month earlier, the drugs were fine. That’s one company.
Jess: There’s another company developing programmable human biobots. There was actually an article about this in Nature recently, and that company is called Anthrobot. CNN is also posting their interview with Mike about that.
Mission Over Money: What Drives Bold Bets [01:54:00]
Sam: Is all your bio stuff under this lab with Mike Levin, or are there other bio bets?
Jess: At that dinner we were talking about pregnancy and I said something in passing — like, in the next ten years or so, women may not need to birth a baby. You could grow a baby in a fish tank. Just swab two people’s mouths, put it in the machine, and the baby starts to grow. No sperm, no egg — just raw genetic material. I don’t think that’s the next ten years, probably not even twenty, but I have random ideas like that. What would be cool is to find who’s doing that research and fund it. If no one is, put together a team and try it ourselves. It’ll likely lose money and fail, but it’s fun.
Jess: I know your whole podcast is about making money, compounding cash flow, and all of that. But what if we could have fun doing this? Being mission-oriented makes you think bigger, think more grand about what the world could become. That makes you more likely to end up like Elon. It’s not as sexy as saying “we’re making money,” but maybe it’s more sexy, I don’t know.
Sam: When Facebook was going public, Zuckerberg wrote that letter to shareholders — The Hacker Way. He said: “We don’t build products to make money. We make money to build great products.” If the first-order priority is funding bold science that might change everything, even though it has a high likelihood of failure and might take many years and a lot of money — that is the version of “we don’t do that to make money, we make money so that we can do that.” That’s actually a lot more attractive and sexier to most people if they step back for a minute.
Jess: A lot of the “money first” thinking comes from insecurity — wanting that success, wanting that win under your belt, wanting that safety in the bank account. I don’t think anyone, if they looked at their life honestly, would say, “I’m so glad I devoted it to maximizing how much money I made.” A lot of people would be more inspired by what you’re doing now — what’s fun, what’s interesting, what gets me out of bed in the morning. That’s exciting. And if done well, it can change the world in the non-cliche way.
Jess: I literally had this nagging feeling in my soul that I was wasting my capability. I’m sure a lot of people feel that way.
Closing: Where to Find Jess [02:00:00]
Sam: Awesome. Sounds like we’ve got another couple of conversations to have. Thank you for coming on. Where should people go find you?
Jess: I’m on my website, mwe.com. I’ve got a Twitter — Jesa. And JMAofficial on Instagram. If people want to reach out, you can guess my email address — which is actually what I’ve done with Mark Benioff and everyone else. That’s a good filter: you don’t want the inbound that’s easy. You want the inbound from someone who can at least figure out an email address. It’s not that hard. I literally emailed every permutation I could think of — Mark.Benioff, MBenioff — and most bounced, and one worked.
Sam: That’s awesome. Thanks for doing this. You’re great.