2025-12-09 21:03:49
“Every single good thing happened in my life on the back of some disappointment or failure. Those rejections became rocket fuel.”
— Aydin Senkut
Two decades ago, Aydin Senkut was a first-time fund manager with a thin track record to show prospective backers. LPs didn’t believe a solo GP, especially one without experience at a legacy firm, could build a lasting franchise.
They were wrong. Today, Felicis is a Silicon Valley mainstay on its 10th fund, a $900M vehicle. Across its history, Felicis has backed a slew of winners, including Shopify, Canva, Crusoe, and dozens of other billion-dollar outcomes. Rather than specialize over time, Aydin has remained a true generalist, investing across markets and cycles. In this conversation, we dig into the frameworks, stories, and philosophies that shaped Felicis into what it is — and where Aydin believes the next decade of technology is heading.
We explore:
How growing up in Turkey with entrepreneur parents shaped Aydin’s approach to risk and investing
Lessons from working alongside Larry Page and Sergey Brin during Google’s early days
Why Felicis deliberately chose a generalist strategy when most VCs were specializing
How international experience became a competitive advantage in finding global winners
The mathematical case for portfolio diversification (50-70 companies per fund)
Why valuation concerns are often overblown when revenue growth is exponential
Felicis’s aggressive AI investment strategy and what other investors are missing
The future of robotics and physical AI through companies like Skild AI
Why learning and adapting rapidly is Felicis’s constitutional principle
(00:00) Introduction
(03:09) How Aydin made his way to Silicon Valley
(06:15) What he learned from his entrepreneurial parents
(08:55) Learnings from the early days at Google
(15:05) The childhood roots of his investing philosophy
(16:31) Why rejection became a catalyst for his venture career
(19:28) Strategy behind Felicis’s first $41M fund
(25:44) How his international background became an investing edge
(28:17) How Aydin approaches diversification at scale
(32:08) How he sizes investments based on conviction
(33:15) Generalist vs. specialist investing
(38:23) Why founders are the foundation
(42:48) Why success may look different than expected
(43:46) The Felicis journey
(48:18) Why Felicis is going all in on AI
(54:54) Why entry point matters less than potential
(57:33) How the AI bubble debate misses the point
(59:47) What makes Skild AI a standout company
(01:04:58) The AI bets Felicis missed
(01:07:55) How missing Airbnb and Uber led to backing Adyen
(01:11:20) Final meditations
LinkedIn: https://www.linkedin.com/in/aydins
Antifragile: Things That Gain from Disorder: https://www.amazon.com/Antifragile-Things-That-Disorder-Incerto-ebook/dp/B0083DJWGO
Clear Thinking: Turning Ordinary Moments into Extraordinary Results: https://www.amazon.com/Clear-Thinking-Turning-Ordinary-Extraordinary/dp/0593086112
Larry Page: https://en.wikipedia.org/wiki/Larry_Page
Sergey Brin: https://en.wikipedia.org/wiki/Sergey_Brin
Eric Schmidt: https://en.wikipedia.org/wiki/Eric_Schmidt
Brian Chesky on X: https://x.com/bchesky
Shane Parrish’s blog: https://fs.blog
Felicis: https://www.felicis.com
Mastering Portfolio Construction: https://www.generalist.com/p/mastering-portfolio-construction
Steve Jobs’s quote on focus: https://www.goodreads.com/quotes/629613-people-think-focus-means-saying-yes-to-the-thing-you-ve
Angry Birds: https://www.angrybirds.com
Rovio: https://www.rovio.com
Adyen: https://www.adyen.com
Canva: https://www.canva.com
Shopify: https://www.shopify.com
n8n: https://n8n.io/
Tines: https://www.tines.com
Crusoe: https://www.crusoe.ai
Supabase: https://supabase.com
Skild: https://www.skild.ai
Anthropic: http://anthropic.com
OpenAI: https://openai.com
Mistral: https://mistral.ai
Airbnb: https://www.airbnb.com
I’d love it if you’d subscribe and share the show. Your support makes all the difference as we try to bring more curious minds into the conversation.
Production and marketing by penname.co. For inquiries about sponsoring the podcast, email [email protected].
2025-12-05 00:19:27
Friends,
This is one of my favorite questions to ask:
If you had the power to assign a book for everyone on Earth to read and understand, what would you choose?
Long-time supporters of The Generalist will know it’s my preferred way to wrap up a Modern Meditations interview or a podcast episode. So, why do I like it so much? Isn’t it just a convoluted way of asking “What’s your favorite book?”
Not quite. (Though that is a pretty great question too, no matter how staid.) There is, I find, something useful about framing the prompt in this way, and asking people not just what books they liked but those they considered deeply important. Plenty of authors can grant us pleasure, but which ones created works that truly merited the world’s attention?
It also opens up the possibility for all kinds of enjoyable subplots. Will someone indulge in the hypothetical chance to promote their own work, thereby locking in a casual 8 billion in new book sales? How might they tilt humanity toward their philosophical or aesthetic preferences? Does it seem utterly unanswerable to them, given the swarm of wonderful books the world contains? Will they reject the premise outright, as a mini-autocracy dressed up as a parlor game? Each of these answers says something, I think, about the way a person reasons.
Over the years, this question has been the source of much joy, intrigue, alpha, and wisdom to me. And so, as we near the end of this year, I took the time to compile every recommendation we’ve received across The Generalist’s written and audio interviews into a single guide, lightly edited for readability. Since it contains no recommendations or musings of my own, I feel I can say with a straight face that it is quite a wonderful document, containing the preferred reads of an eclectic but stunningly accomplished group of people. MacArthur “genius” grantees mingle with multiple Midas List winners, prominent ethical philosophers, legendary entrepreneurs, and extreme biohackers. People who have built new cities sit alongside complexity scientists, a stone’s throw from a computer science legend and former professional poker player. So read on to discover what Alan Kay, Tyler Cowen, Reid Hoffman, David Krakauer, Laura Deming, Bryan Johnson, Katherine Boyle, and others think the world should read.
As you consider how you want to spend your time in 2026, I hope this collection might provide inspiration and open some new avenues for your curiosity to explore.
Two years ago, The Generalist published its case study on Hummingbird. It was the story of a fund that had studiously avoided publicity, while putting together one of the most impressive track records in the asset class, all by focusing obsessively on finding the top 0.1% of founders. It became our most popular piece at the time.
As I shared with readers earlier this year, I became so intrigued by Hummingbird’s psychological approach that I took on a venture partner role. In part, I saw it as a chance to continue studying how the most interesting fund I’d come across functioned from the inside. How exactly did they interact with founders? What questions did they ask? Why? What traits did they look for at an even more granular level?
Since spending more time with the team in this capacity, I’ve been struck by just how deep Hummingbird’s craft goes. (Hopefully, I can share some of these discoveries in a future piece.)
For now, though, an opportunity: Hummingbird opened the application for its analyst program a few weeks ago. It’s exactly the kind of role I would have wanted to discover earlier in my venture career and, based on my experience, a rare one. If you’re interested in learning a differentiated investing lens at one of the best-performing funds in the world, you can apply here.
As you can probably tell from the above, I think it’s a rather good opportunity. Now, onto the piece.
If this is a one-shot opportunity, then I’d probably want to pick a book that has a proven track record for timelessness and universality – in other words, something that I believe could make a lasting impact on the greatest number of readers.
So I think I’d choose Viktor Frankl’s account of his life in a Nazi concentration camp, Man’s Search for Meaning. Originally published in 1946, it’s a book that readers continue to find relevant, decade after decade, because of its emphasis on how, even in circumstances of unimaginable suffering and inhumanity, where despair is a perfectly rational response, we can still find ways to be resilient and resourceful. The key is to maintain hope for the future and a sense of purpose that goes beyond the alleviation of our own suffering and is instead enmeshed in the human connections and relationships that give our lives meaning.
The book I hand out to people is Man’s Search for Meaning by Viktor Frankl. Frankl was a Holocaust survivor, and the book doesn’t detail the horrors of what he endured, but it talks about the insight he had into human nature.
There are competing views of what motivates us. There’s the hedonistic view that we pursue pleasure. Then there’s Adler, who thought we pursue power, and that’s where we derive value and meaning in our lives. Frankl developed logotherapy based on the belief that purpose is what drives us. That purpose could be a mission, a family member, or a pursuit. But there’s something that keeps us going.
Frankl had this insight before he went into the concentration camps, but it was honed by his experience there. He saw, for example, that the death rate in the camp increased around Christmas and the New Year. Not that any of the captives were Christian, but it was a remembrance of time with family. People lost hope during those windows and basically gave up on life because they had no reason to live anymore. Frankl has this phrase, “Someone who has a ‘why’ will bear almost any ‘how.’”
When we think about our own personal life experiences, I think we need to understand meaning. Because money is not going to bring you happiness. It buys luxuries, but it’s not going to bring you happiness. I think it’s very important for people to define their personal happiness.
When it comes to building a company, mission-driven companies just do better. You can’t staple a mission onto a company if it’s inauthentic. It has to be truly authentic. Natera is a good example. It started with the CEO wanting to help people have healthy babies, and though it’s expanded, it remains such a mission-driven company. That mission defines the kind of decisions they make inside the company and gives people comfort when they’re pulling all-nighters or doing incredibly hard work to remember the purpose they’re serving.
To the Lighthouse is an iconic novel. On one level, it’s about a family, but it’s about much more than that. It’s about death, existence, the human condition – and how we can be so close to someone without really knowing them.
From a formal perspective, Woolf immerses you in her characters’ innermost thoughts without using much dialogue and creates a dreamlike state. From the reader’s perspective, you’re surfing different perspectives, different inner monologues, and the passage of time. Nearly a hundred years after it was published, it’s a work that still feels innovative and disruptive.
I really admire Dan Yergin’s The Prize. It’s a history of the last two hundred years through the lens of the most important industry of that period: oil. It’s got it all: the personalities, business, geology, politics, and wars that defined that period. I think you could do no better in understanding why the world is structured the way it is than by reading that one book.
I’d choose Pale Fire by Vladimir Nabokov. It’s a wild, unusual book by an unusual person and author. It’s structured as a fictional 999-line poem and then a fictional line-by-line annotation of it. It requires a lot of choices at every turn – including how to read it (the poem and then the annotation? Flipping back and forth?). So it makes you work for it. But at heart, it’s an incredible work about the relevance of stories, how thin the line is between our reality and the narratives we tell ourselves, and the importance of those narratives for sustenance. It’s also about imagination and creation, and that whole worlds can be created by powerful ideas. It asks the reader to constantly figure out what is real and what is not, or to give up and accept the uncomfortable state of not knowing, thereby embracing the story. I love reading across genres, but nothing deepens my thinking and takes my mind to new places like great works of fiction.
Practical Ethics by Peter Singer is a really good, no-nonsense approach to thinking about ethics. It really helps show you how to reason about all kinds of issues with an open mind, without assuming that our current ethical intuitions are the be-all and end-all.
In that vein, Derek Parfitt mentions that there’s really only been a couple of generations in which people have made what he calls “non-religious ethics” their life’s work. If you look at the whole history of philosophy, almost all ethical discussions occurred within a religious context where the set of possible answers had to align with what had been thought thousands of years earlier. There had really only been a couple of exceptions. And only a short period of time since that kind of inquiry became more widespread. Parfitt saw that as a reason to be optimistic about the possibility of making substantial moral progress.
I would choose The Giver. It’s required middle school reading in parts of America. That’s actually how I came across it: discovering it when my kids were in school. It’s absolutely astonishing. You’re reading this book set in what is supposed to be a utopia. But partway through, there’s a crack in the facade.
I feel like we’re all living in a bubble of this kind, and every once in a while, there’s a crack. It’s our job to look through the crack and figure out what it means for us and those around us.
I’d pick The Weirdest People in the World by Joseph Henrich. It basically says that the Protestant Revolution changed the way we associated ourselves and each other. We used to be very, very tribal, which impacts trust. The Protestant Revolution forced nuclear families and separation, and those shifts required us to be pro-social.
It has a second thesis on how free markets produce pro-social behavior. The reason I’d choose it is that if you look at the long arc of humanity, the ultimate enemy is entropy. That never goes away, and I don’t think any single tribe solves that. So you need pro-social behavior to actually undertake planetary-level innovation, and to do that, we need to understand how we operate when it comes to trust, coordination, and cooperation.
Beyond that, I’d mention David Deutsch’s The Beginning of Infinity, Taleb’s Statistical Consequences of Fat Tails, Hamming’s The Art of Doing Science and Engineering, Fukuyama’s The End of History and the Last Man.
Fukuyama has since recanted on the view in the book, but it’s this Hegelian take on humanity, the conclusion of which is that liberal democracy is the end of history. I think that’s being questioned right now, but Fukuyama does such a great job of outlining the Hegelian perspective and showing there is this evolution of humans, and we are continuing to get better. Fukuyama thought that maybe we’d arrived; the conclusion now is that we haven’t. But I love the idea that, as a species, we’re improving how we interact, how we make policies, and how we socialize.
2025-12-02 21:03:57
Guru: The AI source of truth for work.
Auth0: Secure access for everyone. But not just anyone.
Prediction markets are no longer a fringe curiosity. They are becoming one of the most revealing instruments in modern finance. Platforms like Polymarket, once a niche corner of crypto, now regularly clear billions in monthly volume as traders speculate on everything from political outcomes to sports to cultural events. Few people saw this future as early, or as clearly, as Joey Krug.
A decade before prediction markets went mainstream, Joey dropped out of college to co-found Augur, the first decentralized prediction market protocol. He later became one of the most influential investors in the category by backing Polymarket at Founders Fund. In this conversation, Joey shares why the moment for prediction markets has finally arrived, what has changed, and how these markets are reshaping information flows across society.
We explore:
The experimental mindset that led Joey from horse-racing predictions to mining bitcoin in high school
Why Augur was the right idea at the wrong moment, and what it taught Joey about timing and infrastructure
The product, liquidity, and founder-market fit signals that persuaded Founders Fund to back Polymarket
Why resolution is the hardest problem in prediction markets, and how Polymarket approaches it
How crypto treasury companies are emerging as a major force and where ETFs fit in
Why mimetic behavior drives entire sectors and how savvy investors read those waves
The rise and fall of Operation Choke Point and its impact on crypto
How Founders Fund reframed Joey’s approach to evaluating founders, markets, and structural shifts
(00:00) Intro
(04:10) How Joey began making predictions with horse racing
(08:00) Why Joey began coding with Applesoft BASIC
(09:32) How Joey first discovered crypto
(11:06) Why Joey dropped out of school to pursue crypto
(12:52) The origins of Joey’s interest in medical school
(16:15) How Joey spends nights and weekends splitting time between biotech and trading
(17:18) The early influences behind Augur’s creation
(19:40) Why prediction markets captivated early crypto thinkers
(23:26) The unlock crypto created for prediction markets
(29:22) How Polymarket began and why Joey decided to back it
(32:11) What made Polymarket the right team
(35:25) The FBI raid and how Shane responded
(38:20) Why Joey expected Polymarket’s volume to hold after the election
(40:20) The trend toward duopolies in financial markets
(42:37) What sets Polymarket’s product design apart
(45:25) How to keep prediction markets clear and unambiguous
(48:31) The rise of crypto treasury companies and FF’s work with BitMine
(51:26) The value of crypto treasuries and the role of ETFs
(54:33) The mimetic rise of crypto treasury companies
(57:03) Joey’s take on where the crypto market stands now
(1:00:23) Why Founders Fund is bullish on ETH
(1:03:03) Operation Choke Point, regulatory whiplash, and the end of the crypto crackdown
(1:06:04) Where the Clarity Act falls short
(1:08:56) How Joey’s thinking has evolved since joining Founders Fund
(1:13:21) Final meditations
LinkedIn: https://www.linkedin.com/in/joeykrug
Zero to One: Notes on Startups, or How to Build the Future: https://www.amazon.com/Zero-One-Notes-Startups-Future/dp/0804139296
The Power Law: Venture Capital and the Making of the New Future: https://www.amazon.com/Power-Law-Venture-Capital-Making/dp/B094PSKDZV
More Money Than God: Hedge Funds and the Making of a New Elite: https://www.amazon.com/More-Money-Than-God-audiobook/dp/B004AUQPF0
The Alchemy of Finance: Reading the Mind of the Market: https://www.amazon.com/Alchemy-Finance-Reading-Mind-Market/dp/0471043133
Dan Romero’s website: https://www.generalist.com/p/dan-romero
Sean Parker on LinkedIn: https://www.linkedin.com/in/parkersean
Volodymyr Zelenskyy: https://en.wikipedia.org/wiki/Volodymyr_Zelenskyy
Micree Zhan on LinkedIn: https://www.linkedin.com/in/micree-zhan-305a1817a
Tom Lee on X: https://x.com/fundstrat
Michael Saylor’s website: https://www.michael.com
Peter Thiel on X: https://x.com/peterthiel
No Rivals: The Prophet (Part I): https://www.generalist.com/p/founders-fund-1
No Rivals: The Disciples (Part II): https://www.generalist.com/p/founders-fund-2
Founders Fund: https://foundersfund.com/
The Kentucky Derby: https://www.kentuckyderby.com
Applesoft Basic: https://en.wikipedia.org/wiki/Applesoft_BASIC
Bitcoin: A Peer-to-Peer Electronic Cash System: https://www.ussc.gov/sites/default/files/pdf/training/annual-national-training-seminar/2018/Emerging_Tech_Bitcoin_Crypto.pdf
Ethereum Whitepaper: https://ethereum.org/whitepaper
Atypical Hemolytic Uremic Syndrome: https://my.clevelandclinic.org/health/diseases/atypical-hemolytic-uremic-syndrome
Soliris: https://www.drugs.com/soliris.html
Alexion: https://alexion.com
Augur: https://en.wikipedia.org/wiki/Augur_(software)#References
The Future of Farcaster with Dan Romero: https://www.generalist.com/p/dan-romero
Polymarket: https://polymarket.com
Kalshi: https://kalshi.com
Alchemy: https://www.alchemy.com
Pantera Capital: https://panteracapital.com
CME Group: https://www.cmegroup.com
CBOE: https://www.cboe.com
BitMine: https://www.bitminetech.io
Workrise: https://www.rigup.com
Clarity Act of 2025: https://www.congress.gov/bill/119th-congress/house-bill/3633
Joining Founders Fund: https://medium.com/@joeykrug/joining-founders-fund-4c3544633081
I’d love it if you’d subscribe and share the show. Your support makes all the difference as we try to bring more curious minds into the conversation.
Production and marketing by penname.co. For inquiries about sponsoring the podcast, email [email protected].
2025-11-20 22:42:23
Friends,
Where have the heretics gone?
There is a feeling in the venture landscape at the moment of intense, ferocious orthodoxy. Everyone agrees that AI is a significant technology. The question of its impact is only one of degree. Does it count as heresy to simply pay more for the same company everyone agrees is compelling? Equally, is there any originality in sniffing that prices are too high?
AI is not the only example. To a lesser extent, the same can be said of sectors once considered untouchable. With the exception of contrarians like Founders Fund, VCs of the 2010s balked at backing defense and industrial companies. Now, they are in fashion. The result is that the space for heresy has shrunk.
Of course, this is very good news, for it is usually in periods of fervid homogeneity that a new paradigm emerges. Only when everything looks dull and solved is it possible for an idea to emerge and flip the perspective.
Floodgate founder Mike Maples, Jr. has made a career out of finding unlikely ideas, primed for major impact. More than many other VCs, he has made a concerted effort to uncover what it takes for an idea to be truly “different.” And so, in this edition of “Letters to a Young Investor,” I asked for his thoughts on what constitutes a true heresy and where investors might find them in the age of AI.
You’ll find an honest appraisal of the difficulty of thinking differently and what it takes to translate that into investing decisions.
What you’ll learn:
The three ingredients of heresy. Heresy isn’t just about inverting the consensus position. To find a truly heretical idea, Mike argues that a founder needs to have gone through (i) a different life experience that allows them to (ii) see something others don’t, and then must (iii) have the courage to act on it.
Using AI to solve a problem. Many of the companies gaining attention in AI are using the technology for its own sake, not to solve a real problem. Mike is increasingly excited by founders from the material sciences and drug discovery spaces that have been able to leverage modern AI to solve problems they’ve thought about for years.
Finding “new scarcities.” Every new technology creates a new scarcity. As Mike explains, when computation became cheap, software became scarce, given how important and useful it had suddenly become. Similarly, AI has commoditized some forms of cognition while others remain unsolved.
Investing in the “capability cycle.” Rather than trying to time the hype cycle, Mike recommends focusing on how the underlying capabilities are progressing. Then, find the entrepreneurs who have waited their whole careers to build something that new capability unlocks.
Recognizing heresy. It is difficult to summon heretical ideas unbidden. However, Mike has learned to recognize it when he sees it, noticing the mix of excitement and discomfort such ideas tend to produce.
As a refresher, “Letters to a Young Investor” is a series designed to give readers like you an intimate look at the strategies, insights, and wisdom of the world’s best investors. We do that via a back-and-forth correspondence that we publish in full – giving you a chance to peek into the inbox of legendary venture capitalists. Here’s a selection of previous correspondences:
To access today’s correspondence and unlock the full collection, join Generalist+ today. For the price of a business lunch, you’ll unlock a lifetime of distilled investing wisdom.
Great ideas aren’t hard to come by. Follow-through is what’s rare.
And when you’re reviewing the business plans of dozens of companies, it becomes clear which of them are able to put their vision and plans on paper — and which are getting a little lost along the way.
That’s why Mercury created their free business plan template. It’s designed to help founders map out their goals and strategy in a fully customizable way. Share it with the companies in your portfolio to help structure their thinking about the future — and make your next check-in even more productive.
Mercury does business banking* differently. They go beyond banking to help businesses operate like pros at every stage with resources just like this.
*Mercury is a financial technology company, not a bank. Banking services provided through Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.
Subject: AI Heresies
From: Mario Gabriele
To: Mike Maples, Jr.
Date: Tuesday, October 28, 2025 at 5:00 PM GMT
Mike,
The English writer Graham Greene addressed the matter well: “Heresy is another word for freedom of thought.” Greene spoke from experience. His novel The Power and the Glory, chronicling the struggles of a Mexican “whisky priest,” was viewed as so heterodox by the Catholic Church that it considered issuing a blanket ban.
In a previous conversation, you mentioned the topic of “heresy” and its role in the context of startups. That immediately intrigued me. It is, after all, an emotive, laden word. Reading your last letter, I began to see how it might fit into your model of investing. This notion seemed to be embedded in your recollections of Airbnb, Figma, Twitter, Applied Intuition, and Twitch; that a kind of profound dissidence is not merely intriguing, but required for a truly outlier outcome.
In one sense, venture investors have articulated a version of this wisdom for some time. A good student of startups now knows that it is not enough to be right – you must be contrarian and right. If your company advances a consensus view of the world, even in success, it will struggle to make a big enough impact. But from your work, it’s clear that you think about heresy at a deeper level, taking inspiration from historical figures like Galileo. I’d be keen to hear what this word means to you as an investor, and what distinguishes authentic heresy from mere originality.
More concretely, I’d be interested in hearing how you think about heresy in the context of AI. On the one hand, the AI world remains roiled by disagreements. Deeply felt philosophical differences animate pockets of the industry. On one end of the spectrum are accelerationists who believe human flourishing and national competitiveness require us to hit the gas; on the other end are “doomers” who believe the end is nigh. In the middle sit a wide range of builders and researchers who see both real risk and immense possibility.
While this debate plays a critical role in the zeitgeist, it doesn’t especially seem to perturb the direction of capital allocation. Seemingly without exception, venture investors are keen to invest in the current wave, even as technological breakthroughs appear to slow and valuations inflate. A grand financial consensus has appeared to form in the private markets, with the only real discussion being the degree to which AI will change everything.
Over the past six months in particular, this seems to have created a culture of orthodoxy and replication. Every few days, we see a new prompt-to-code product or browser agent released. Each week, an “AI for X” vertical takes the stage. Nearly all seem to receive backing from credible investors ready to believe that this one, this umpteenth iteration, will be the winner. (From stage right, Peter Thiel shouts “mimesis!”) Some of these startups will undoubtedly work, and a sparse few may succeed outlandishly. But when creative homogeneity seems to have taken so firm a hold, where is the space for heresy? Amid glossy uniformity, what does “different” look like today?
As you know better than I do, true heresy is not merely the repudiation of the old model. There is little value in simply declaring AI to be moribund. The real breakthrough will come from introducing a new paradigm; by arriving orthogonally, carrying a strange truth. Where might this come from? It is usually not the job of investors to come up with heresies, but the best tend to be gifted at knowing where it might originate. What dynamics are you heeding? As greater sums are ploughed into escalating an existing paradigm, where have you started directing your attention?
It is a kind of market parlor game to compare eras. But given that you lived through the dotcom boom and bust as an entrepreneur, I wonder what rhymes with that era you hear today. Does this remind you of the late-90s or do the comparisons obscure rather than reveal?
More tactically, how have you sought to play the AI revolution at Floodgate? What is the kind of risk you’ve been happiest buying? You’ve written about the importance of timing in startup success. How much do you think about timing technological cycles as you deploy capital? Is it useful to have a sense of this in your head, or does the game return, unerringly, to listening and paying attention to special people when you come across them, regardless of the market’s machinations?
With gratitude,
Mario
Subject: AI heresies
From: Mike Maples, Jr.
To: Mario Gabriele
Date: Thursday, November 13, 2025 at 12:24PM PT
Dear Mario,
Your letter about heresy arrived at a weird moment for me. Or, maybe it’s not weird at all. Maybe you chose these questions because all of us are in a weird moment.
I’ve been sitting with your Graham Greene quote and your questions for more than two weeks now. (Sorry about that.) One reason is that something keeps bothering me: If heresy is freedom of thought, then do I actually have any heresies left in me?
Or, do I just have a bunch of sophisticated-sounding opinions that I’ve convinced myself are heresies because they buy me status at dinner parties and keynote pitches?
I keep feeling that there’s a bigger question behind your questions. Am I, or the broader VC industrial complex I’m part of, actually spotting genuine heresy anymore? Is it possible that “seeming contrarian” has become the new orthodoxy?
The honest answer is that I don’t know.
And that’s scary to say because they tell me my job is to spot non-consensus futures. Let me see if I can work through this honestly, including the parts where I’m confused.
Here’s how I think about it: Contrarians say everyone thinks A, so I’ll say B. That’s still playing the same game, and just taking the opposite position. Heretics are saying something different. They’re saying the whole A/B way of thinking about the problem is broken. Usually it’s because they’ve seen an anomaly that the old pattern can’t explain.
With Airbnb, Brian, Joe, and Nate didn’t start by thinking about hospitality. They were broke friends trying to pay next month’s rent. Renting their apartment to strangers seemed like an easy way to make fast money. But when they offered their apartment to guests, they noticed something surprising: if you make staying with strangers feel meaningfully human, people will choose it. That insight didn’t fit any existing pattern.
This is what I’m trying to figure out: is heresy a cognitive difference (seeing something others don’t see) or a courage difference (acting on something others won’t act on) or a life experience difference (seeing something because you experienced something a whole bunch of other people are about to see?)
And actually (this is where I think I’ve been wrong) maybe genuine heresy requires all three. You need the perceptual difference to notice something meaningful, the relevant experience to know when that perception matters, and the courage to act on it. Which might explain why heresy is so rare.
You can see all three in the Airbnb story: You notice what others overlook. You act before anyone else believes or cares. Your life circumstances exposed you to this truth first.
There’s far less room for heretical insight in AI than most people admit. Most debates, like big vs. small models, open vs. closed source, and agents vs. assistants, are just different moves inside the same game. If history rhymes, the real opportunities will emerge from somewhere surprising, from a place or anomaly everyone has dismissed.
Something else is happening too. The founders raising money aren’t necessarily the ones who’ve noticed something true about the world. They’re the ones who can tell a good story about platform shifts and timing. That part sounds like 1999 all over again.
Here’s the scary part: a well-told story can sound exactly like an insight. It has the same structure and words. But real insight comes from noticing something specific about reality. Story increasingly comes from noticing what gets funded.
2025-11-18 21:03:15
“Close to one-third of all of India’s consumer deposits, which is about $1 trillion, comes from the diaspora. So 1% of the population contributes to 30% of deposits.”
GoFundMe Giving Funds: One Account. Zero Hassle.
Guru: The AI source of truth for work.
Persona: Trusted identity verification for any use case.
In the summer of 2022, Parth Garg woke up in Bangalore to discover that his co-founder had fled the country and emailed their investors to tell them their company was dead. Just over three years later, Aspora is one of fintech’s fastest-growing startups. The company, which makes it faster and cheaper for India’s diaspora to send money home and access banking services, now processes close to half a billion dollars in volume every month and has earned a $500 million valuation with backing from elite investors like Hummingbird Ventures, Sequoia, and Greylock.
In this conversation, Parth shares his journey from physics prodigy to fintech founder, offering insights into what it really takes to build resilience as a founder and how to create a culture where feedback flows freely, even without a co-founder to provide checks and balances.
We explore:
The moment when Parth discovered his co-founder had left the country and told investors the company was shutting down
How Parth’s childhood moving between cities in India and later to the UAE shaped his adaptability and entrepreneurial mindset
His journey from physics prodigy to startup founder, including early ventures before Aspora
The process of discovering product-market fit through structured experimentation after the initial business model failed
Why the Indian diaspora represents a massive, underserved financial opportunity (1% of the population contributing 30% of deposits)
How stablecoins dramatically reduced Aspora’s working capital requirements and transformed their business model
The regulatory landscape for fintech and crypto in India and the impact of the GENIUS Act in the US
Aspora’s vision to become a comprehensive cross-border bank serving multiple diaspora communities globally
(00:00) Intro
(03:53) How Parth felt when his co-founder fled the country
(07:04) Parth’s early days in India and the UAE
(09:37) Parth’s love of physics and competitiveness
(12:15) The not-so-straightforward path from studying physics at Stanford to entrepreneurship
(14:13) Parth’s physics heroes
(16:24) The gap year that sparked Parth’s entrepreneurship journey
(18:36) Parth’s first startup: selling near-expired groceries
(21:58) Moving back to the United States and founding Vance
(28:00) Joining YC and finding early backers
(31:14) How Parth realized Vance needed to pivot
(35:22) How Parth moved forward after his co-founder fled
(37:37) Building psychological safety and open debate at Aspora
(40:15) How conversations with immigrants inspired Aspora’s idea
(45:13) How stablecoins solved Aspora’s biggest operational challenges
(46:57) Aspora’s current scale and why India was the perfect starting point
(51:34) How Aspora builds loyalty in a low-switching-cost market
(52:42) The GENIUS Act and the real opportunity in stablecoins
(55:52) The evolution of crypto and stablecoins in India
(56:50) The importance of partnerships for scaling Aspora in India
(58:18) The next phases of Aspora’s growth
(01:00:04) The role of Aspora’s new bets team
(1:01:20) Final meditations
LinkedIn: https://www.linkedin.com/in/parth29
“Surely You’re Joking, Mr. Feynman!”: Adventures of a Curious Character: https://www.amazon.com/Surely-Youre-Joking-Mr-Feynman/dp/0393355624
Elon Musk: https://www.amazon.com/Elon-Musk-Walter-Isaacson/dp/1982181281
Carl Sagan’s website: https://carlsagan.com
Isaac Newton: https://en.wikipedia.org/wiki/Isaac_Newton
Leonard Susskind: https://sitp.stanford.edu/people/leonard-susskind
Richard Feynman: https://en.wikipedia.org/wiki/Richard_Feynman
Firat Ileri on LinkedIn: https://www.linkedin.com/in/ilerifirat
Akshay Mehra on LinkedIn: https://www.linkedin.com/in/akshaymehra-
Lee Kuan Yew: https://en.wikipedia.org/wiki/Lee_Kuan_Yew
Dee Hock: https://en.wikipedia.org/wiki/Dee_Hock
Dark Energy Spectroscopic Instrument: https://www.desi.lbl.gov
Club Rise: https://clubrisead.wordpress.com
Amway: https://www.amway.com
Shorooq: https://www.shorooq.com
Starbucks, a Tech Company: https://www.generalist.com/p/starbucks-a-tech-company
Y Combinator: https://www.ycombinator.com
Hummingbird VC: https://www.hummingbird.vc
Zip: https://zip.co
GENIUS Act: https://en.wikipedia.org/wiki/GENIUS_Act
Stripe completes Bridge acquisition: https://stripe.com/newsroom/news/stripe-completes-bridge-acquisition
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2025-11-11 21:03:43
“We’re trying to solve Earth. Some people are trying to go to Mars… but we are trying to make Earth the most prosperous place possible — and that is all about governance.”
GoFundMe Giving Funds: One Account. Zero Hassle.
Guru: The AI source of truth for work
Tezi: The AI agent for recruiting high-quality candidates quickly.
What if you could redesign the rules of society? Not tweak the margins, but start over entirely. That’s the question driving Erick Brimen, founder and CEO of Próspera, a private charter city in Roatán, Honduras. Próspera is a radical experiment in governance: a platform that lets governments and entrepreneurs build cities with new legal systems, regulatory frameworks, and institutions from the ground up. Brimen believes that governance itself can be innovated upon. That cities, like software, can be upgraded. His goal isn’t just to build one new jurisdiction, but to create an operating system for hundreds of prosperous, self-governing communities around the world. In this conversation, Erick and I explore what it really takes to build a modern Singapore from scratch — and why better governance might be humanity’s most powerful lever for progress.
Together we explore:
How Brimen’s childhood in Venezuela shaped his understanding of governance and poverty
The historical precedents for charter cities like Dubai, Singapore, and Hong Kong
Why common law, trusted dispute resolution, and dynamic governance are essential foundations
How Próspera’s Governance-as-a-Service model aligns incentives between governments, operators, and residents
The current state of Próspera in Honduras, including its three hubs and economic impact
The political challenges Próspera has faced and how international arbitration has protected the project
Why regulatory innovation enables industries like biotech, crypto, and advanced manufacturing to flourish
How the model could be applied to “catch-up growth,” industry diversification, and accelerating growth in developed nations
The vision for a modern Hanseatic League of charter cities operating on shared governance principles
(00:00) Intro
(04:10) An overview of Próspera and charter cities
(06:43) City of Próspera vs. the platform
(08:06) How growing up in Venezuela shaped Erick’s entrepreneurial vision
(12:36) The limits of seasteading and why Erick took a different path
(15:20) The opposing philosophies that shaped Erick’s path
(16:16) The moment that reshaped Erick’s understanding of poverty
(19:57) The limits of learning from Dubai, Singapore, and Hong Kong
(23:01) Building on the DIFC blueprint
(25:12) From Arizona to Honduras: how Próspera built its first city
(30:36) Why Honduras won
(32:12) Inside the ZEDE framework
(36:56) Próspera’s business model
(43:45) Conditions on the ground in Honduras
(47:14) A quick summary of how it works
(48:24) Quick stats on Próspera’s scale and financing
(50:47) What years of preparation made possible
(52:44) The scale and purpose of Próspera’s three hubs
(58:12) Próspera’s 10-year vision
(1:01:12) The people Próspera was built to serve
(1:04:10) Why less regulation unlocks more innovation
(1:05:58) Próspera’s political headwinds
(1:12:36) Why Erick remains optimistic that things will work out in Honduras
(1:14:44) Addressing criticism of ZEDEs and Próspera
(1:18:08) What’s next, and why the U.S. may be the greatest opportunity
(1:22:30) Final meditations
LinkedIn: https://www.linkedin.com/in/erickbrimen
Website: https://www.erickbrimen.com
Atlas Shrugged: https://www.amazon.com/Atlas-Shrugged-Ayn-Rand/dp/0451191145
Doug Ducey on X: https://x.com/DougDucey
Peter Thiel on X: https://x.com/peterthiel
Marc Andreessen on X: https://x.com/pmarca
Bryan Johnson on X: https://x.com/bryan_johnson
Paul Romer on X: https://x.com/paulmromer
Próspera: https://www.prospera.co/en
Hanseatic League: https://en.wikipedia.org/wiki/Hanseatic_League
Seasteading: https://en.wikipedia.org/wiki/Seasteading
The Seasteading Institute: https://www.seasteading.org
DIFC: https://www.difc.com
ZEDE: https://en.wikipedia.org/wiki/Zone_for_Employment_and_Economic_Development
The Federalist Papers: https://guides.loc.gov/federalist-papers/full-text
Don’t Die: The Man Who Wants to Live Forever on Netflix: https://www.netflix.com/title/81757532
I’d love it if you’d subscribe and share the show. Your support makes all the difference as we try to bring more curious minds into the conversation.
Production and marketing by penname.co. For inquiries about sponsoring the podcast, email [email protected].