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
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].
2025-11-11 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].
2025-10-30 21:23:43
“I think your Substack contains simply the best writings about venture out there. You provide a kind of storytelling and thoroughness that no one else does. Thanks :)” — David, a paying member
Friends,
There is a certain category of article that I find difficult to name, but which I always enjoy reading. We might call it a collection of musings, a set of opinions, a list of miscellaneous observations. Alex Guzey calls his version “Lifehacks,” Laura Deming refers to hers as “mental models,” and Nat Friedman prefaces his as “some things I believe.”
Each offers a numbered list of thoughts. Some are simple, others deceptively profound. Part of what is enjoyable about these lists is that the things I find simple, you are likely to find profound, and vice versa. Equally, those that I enthusiastically endorse, you may consider absurd.
Whatever one’s take on the individual insights, as a whole, they represent efficient distillations of someone’s mind. Read them and you feel as if you know the person a little better; as if you have gotten a tour of their inner landscape. More importantly, you start to see your own mind reflected.
Today, I’m sharing my version. It is a collection of observations that are true to me. I would be surprised if, in ten years’ time, I don’t disagree with myself, but for the moment, it is an authentic distillation of my mind. My hope is that it sparks some interesting reflections for you and perhaps introduces some new lenses through which you view your work, goals, and interactions.
If you have one truly good idea in your life, that is more than enough.
To improve your mind, read fiction. We spend the vast majority of our professional lives in pure knowledge-gathering mode; there are different, deeper truths hidden in stories.
“Never quit” is terrible advice. Try lots of things, quit lots of things. Your time is not infinite. Sometimes you have to give up an old dream for a better one to emerge.
It’s more impactful to know your most talented contemporaries than your heroes. Meeting a hero is unlikely to change the course of your life. But if you meet the most talented minds of your generation early, you can spend the next fifty years collaborating with them as they scale.
Status transactions are happening everywhere, all the time. If you’re not attuned to this, you will miss half of what’s happening in a given conversation.
Learning how to ask good questions is a legitimate discipline worth studying. We underestimate how much insight, connection, and alpha are unlocked by the right series of words. Exponents of this art form change the texture of a conversation at any moment.
Resist other people’s attempts to categorize you. They are missing too much context to do so well.
If you want to really remember a book, buy the physical version and read with a pen in your hand.
It is possible to reinvent yourself at any moment. Cultivate a loose attachment to your view of yourself.
Debate is one of the least effective ways of making up your mind on a topic. It is only worthwhile as a theatrical enterprise. (Written debate is better.)
“Where is it written…” Assume that most conventions are arbitrary and illegitimate. Rules are more malleable than we believe.
Imagine “pulling forward” skills from your future self into the present. If you wish you were a better public speaker, imagine the future version of yourself giving that ability to the present version of yourself.
Genius is narrower than we tend to believe. It extrapolates poorly outside a given field, era, or context. A genius pontificating on something outside of their discipline is probably less reliable than a regular person.
Even the best of minds suddenly burn out. (See: Newton, Grothendieck, Fischer.) Before you persuade yourself that there must be some hidden brilliance in a genius’s proclamations, consider this.
Learn keyboard shortcuts; use snippets.
Listening to the audiobook is fine for entertainment, not for retention.
The current founder trend of prioritizing attention above all else misunderstands greatness. No legendary company won through stunts. At some point, you actually have to build something valuable.
It should concern you if you have never failed at something. You should fail badly, relatively often. Otherwise, you are playing it too safe.
The pressure to be “well-informed” has made us more ignorant. Unless you work in one of a small number of professions, there is no value in reading the day’s news. It stales quickly, tends toward the histrionic, and underweights relevant historical context. Much better to scan the headlines every couple of weeks and pick a relevant topic to learn about from higher-quality sources.
We overvalue the freshness of information. Read old books. There is usually a reason they survived.
Amor fati.
The finest practitioners of a given discipline are often the worst at articulating their craft. Too much of their skill comes from inherent qualities, or abilities illegible even to themselves. Better to watch these people rather than ask them to explain.
Most modern writing advice is copywriting advice. Be careful.
Striving for legibility is overrated. It is much better to adopt a degree of inscrutability. What you lose in definition, you gain in freedom and flexibility.
If someone tells you to pick between two trade-offs (e.g., speed vs. cost), default to rejecting the premise. Sometimes you really do have to make a choice, but you can find a way to have both more frequently than you expect.
You can neutralize most conversational risks by calling them out. (E.g. “I’m being quite direct here…”; “I recognize this is very persistent of me…”)
There is huge alpha in carefully reviewing the source material. (See: Eli Dourado.)
Question the assumptions and run the numbers yourself. Everyone assumed it was economically infeasible for a private company to build rockets until Elon opened his spreadsheet.
Test out vastly disparate career paths as early as you can. Most people test within an extremely narrow band (e.g., going from banking to consulting to big tech).
If you want to become the best at something, you have to devise a kind of differential training. You cannot achieve something new by adhering to the same path as those before you.
Great things happen at the collision between fields.
The collective opinion on who the “best” is in a given industry is usually spotty or simply wrong. Proximity is often required to assess quality, and the most skilled practitioners may not advertise their approach.
Love is easy. The difference between bad relationships and meeting your spouse is not a matter of degree, but category. Compatibility is unignorable and effortless.
Earning your first $1 on the internet can change your life.
“Art is never finished, only abandoned.”
If you have not changed your mind about something important in the past ten years, you should be concerned.
You cannot have an interesting conversation without an element of risk. One person, or both, must subtly push the boundaries.
Every once in a while, you’re reminded that people perceive the world so differently from you that they may as well be on another planet. This is happening all the time, whether you notice it or not.
Allow yourself to be the dumbest person in the room. You will ask better questions and go to better rooms.
“A Prince who is not himself wise cannot be well advised.”
You become solely responsible for your education once you leave school. You must learn to become your own teacher; most do not.
To make an impact on the world, you must pay a debt to modernity. It is romantic to imagine succeeding just as your heroes once did, but they lived in a different time, in different circumstances. A concession to the present day is necessary.
The same skills that made you a good student may make you a bad employee.
“How you do anything is how you do everything” is a perfect encapsulation of what is not true. Brilliance is context-dependent. Energy is context-dependent. Insight is context-dependent. (See: Jobs’ pathetic job application.)
Set yourself a curriculum. What books do you want to read this year? How can you organize them? What gap in your knowledge still bothers you? These questions are your responsibility to answer.
At some point, you must internalize the fact that people will dislike you through no fault of your own, and that it is not your job to change their minds.
“Real artists ship.”
The first time you think you’ve missed the wave, there are probably still a couple of decades left. (See: the internet, crypto, AI.)
Sleeping on an important decision really does help.
Billions of dollars have been invested in making social media platforms addictive. Relying on willpower alone is a lot to ask. Invest in content blockers as you rewire yourself. Cold Turkey is a good one.
Learn to respect the process of the unconscious mind, especially in creative matters. Sometimes, you cannot chase the answer; you must wait for it to come to you.
You become the stories you tell yourself about yourself.
Respect your process. If you do your best work at 4 AM with a bowl of candied ginger, do that. Give yourself the latitude to be a difficult artist when necessary.
Simply decide that you are willing to go first. That could be raising your hand to volunteer for something, taking the first leap off the high dive, or responding to a question that leaves an awkward silence. You reduce social anxiety and increase your agency by just defaulting to taking responsibility.
2025-10-28 20:03:36
“Psychedelics increase the neuroplasticity in your brain that we can measure. I could look at your brain before and after psychedelics. Before, it looks like an internet map of Africa — some areas don’t have connectivity. Afterward, it looks like an internet map of Europe, with condensed connections everywhere.”
Enterpret: Transform feedback chaos into actionable customer intelligence.
Auth0: Secure access for everyone. But not just anyone.
Persona: Trusted identity verification for any use case.
Often called the godfather of NYC tech, Kevin Ryan is one of America’s most influential entrepreneurs and investors. He co-founded MongoDB, Business Insider, Gilt Groupe, Zola, and Transcend Therapeutics, and continues to build and back new companies each year through AlleyCorp. Earlier in his career, he led DoubleClick from a 20-person startup to a global leader, taking it public before its acquisition by Google.
In this episode, Kevin shares his insights on two surprising pockets of the future that he’s betting on: psychedelics for mental health and AI-powered materials science. He unpacks how psychedelics are showing remarkable success in treating depression and PTSD, and why AI may discover revolutionary new materials, from helicopter blades to smartphone glass, that humans never imagined possible.
We explore:
The promising results of psychedelics in treating depression, PTSD, and addiction
How AI is accelerating materials discovery by exploring combinations humans wouldn’t try
The challenges of building successful incubators and why most attempts fail
How MongoDB lost $1 billion before turning a profit (and why it was worth it)
Why e-commerce businesses like Gilt Groupe often struggle against physical retail
How AlleyCorp plans for the future when shaping its investment strategy
What it really costs society to imprison someone for a year
The hard truth about Europe’s tech ecosystem and why it struggles to compete with the US
(00:00) Intro
(04:30) How Kevin collaborated with Scott Adams
(07:11) The origins of AlleyCorp
(08:33) The challenge of incubation
(10:00) Why intellectual flexibility matters
(10:54) What made MongoDB a breakout success
(13:49) How shifting market dynamics hurt Gilt’s business
(16:22) What Kevin would do differently if he built Gilt again
(17:45) Juggling AlleyCorp’s long-term vision with day-to-day demands
(20:26) How to make boards more productive
(22:25) Why Kevin believes investors should also found companies
(24:18) Future spaces Kevin is excited to invest in
(25:52) Kevin’s interest in psychedelics and founding Transcend
(28:20) Psychedelics for mental health
(32:03) How psychedelic therapy is being conducted
(34:11) Transcend’s work and the path to approval for methylone
(37:47) The challenges of psychedelic research
(40:28) How the Trump administration aims to accelerate psychedelic research
(41:50) The size and growth of the psychedelic market
(44:28) Materials science: What it is, its design tradeoffs, and how AI speeds discovery
(49:02) Radical AI’s work creating new compounds
(50:34) The industries Radical AI is targeting
(52:50) The state of European tech and why it still lags behind
(58:26) Final meditations
LinkedIn: https://www.linkedin.com/in/kevinryan3/
How to Change Your Mind: What the New Science of Psychedelics Teaches Us About Consciousness, Dying, Addiction, Depression, and Transcendence: https://www.amazon.com/Change-Your-Mind-Consciousness-Transcendence/dp/1594204225
Breakneck: China’s Quest to Engineer the Future: https://www.amazon.com/Breakneck-Chinas-Quest-Engineer-Future/dp/1324106034
Why We Sleep: Unlocking the Power of Sleep and Dreams: https://www.amazon.com/Why-We-Sleep-Unlocking-Dreams/dp/1501144324
Outlive: The Science and Art of Longevity: https://www.amazon.com/Outlive-Longevity-Peter-Attia-MD/dp/0593236599
Birnam Wood: https://www.amazon.com/Birnam-Wood-Novel-Eleanor-Catton/dp/1250321719
The Odyssey: https://www.amazon.com/Odyssey-Homer/dp/0393356256
Invisible Man: https://www.amazon.com/Invisible-Man-Ralph-Ellison/dp/0679732764
Abundance: https://www.amazon.com/Abundance-Progress-Takes-Ezra-Klein/dp/1668023482
The Optimist: Sam Altman, OpenAI, and the Race to Invent the Future: https://www.amazon.com/Optimist-Altman-OpenAI-Invent-Future/dp/1324075961
The Gods of New York: Egotists, Idealists, Opportunists, and the Birth of the Modern City: 1986-1990: https://www.amazon.com/Gods-New-York-Idealists-Opportunists/dp/052551063X
Eliot Horowitz on LinkedIn: https://www.linkedin.com/in/eliothorowitz
Dwight Merriman on LinkedIn: https://www.linkedin.com/in/dmerr
Fred Wilson on LinkedIn: https://www.linkedin.com/in/fredwilson
Jamie Dimon on LinkedIn: https://www.linkedin.com/in/jamiedimon
Joseph F. Krause on LinkedIn: https://www.linkedin.com/in/josephfkrause
Jorge Colindres on LinkedIn: https://www.linkedin.com/in/jcolindres
James Baldwin: https://nmaahc.si.edu/explore/stories/introduction-james-baldwin
Dilbert: https://dilbert.com
Peanuts: https://www.peanuts.com
DoubleClick: https://en.wikipedia.org/wiki/DoubleClick
MongoDB: https://www.mongodb.com
Business Insider: https://www.businessinsider.com
Zola: https://www.zola.com
Gilt Groupe: https://en.wikipedia.org/wiki/Gilt_Groupe
AlleyCorp: https://alleycorp.com
Oracle: https://www.oracle.com
SAP: https://www.sap.com
Snowflake: https://www.snowflake.com
John Deere: https://www.deere.com
Tech:NYC: https://www.technyc.org
Stepful: https://www.stepful.com
Yale Program for Psychedelic Science: https://medicine.yale.edu/psychiatry/research/clinics-and-programs/psychedelic/
Transcend: https://transcendtherapeutics.com/
A Multi-Site Phase 3 Study of MDMA-Assisted Psychotherapy for PTSD (MAPP1): https://clinicaltrials.gov/study/NCT03537014
Ibogaine treatment outcomes for opioid dependence from a twelve-month follow-up observational study: https://pubmed.ncbi.nlm.nih.gov/28402682/
Methylone: https://www.sciencedirect.com/topics/medicine-and-dentistry/methylone
Radical AI: https://www.radical-ai.com
Uala: https://www.uala.com.ar
Noma: https://noma.dk
Revolut: https://www.revolut.com
Monzo: https://monzo.com
Here’s What Happens When You Give People Free Money: https://www.wired.com/story/sam-altmans-big-basic-income-study-is-finally-out
Altered States and Social Bonds: Effects of MDMA and Serotonergic Psychedelics on Social Behavior as a Mechanism Underlying Substance-Assisted Therapy: https://pmc.ncbi.nlm.nih.gov/articles/PMC11378972/
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2025-10-23 20:32:01
“I’m new to VC and you’ve given me access to learnings from the best of the best! Appreciate you!” — Zhu, a paying member
Friends,
At its core, “Introduction to Poetry” by Billy Collins is about the difference between the drive to define something and the drive to understand it. In a few sparse lines, Collins contrasts the way he wishes readers would appreciate poetry with the manner in which so many do so. Rather than appreciating its contours and marveling over its intricacies, most readers prefer to pummel a poem for information. Instead of holding it to the light “like a color slide” or “waterski[ing]” across its surface, they “begin beating it with a hose/to find out what it really means.” In their drive to define the work in front of them – to analyze and probe it – Collins’ readers neglect its beauty, and miss what really makes it tick.
Though Collins is talking about poetry, he could just as well have been describing any craft. No matter the discipline, there is always this tension between defining and understanding, controlling and observing, grasping and witnessing.
When it comes to the craft of venture capital, Mike Maples, Jr. is one of its great appreciators. Over the past two decades, the Floodgate co-founder has built a remarkable track record by attuning himself to the frequency of great entrepreneurs, observing their quirks, and seeking to understand. As Mike himself describes it, his praxis is not about thinking faster or exhaustively analyzing a market, but simply listening differently. That approach has allowed Mike to make many outlier investments long before they broke out, backing Twitter, Twitch, Okta, and Applied Intuition in their messy infancies.
As part of The Generalist’s “Letters to a Young Investor” series, we’ll explore the nuances of Mike’s craft. To learn how one of the best early-stage investors of the past twenty years spots the future and identifies anomalies, read on. To enjoy the full correspondence and the rest of The Generalist’s exclusive interviews, join as a premium member for just $22/month. For the price of a single business lunch, you’ll unlock the strategies of some of the world’s best investors, founders, and operators.
VC checks may be shrinking, but ambition is on the rise.
Mercury’s 2025 data report, The New Economics of Starting Up, surveyed 1,500 early-stage founders across funding, AI adoption, hiring, and more. For investors, it’s a signal worth watching. Founders aren’t slowing down — they’re rewriting the playbook.
Here’s a preview of what they learned:
Self-funding is the number one avenue for accessing capital — even for tech companies, with half likely to bootstrap.
87% of founders are more optimistic about their financial future than they were last year, despite prevailing uncertainties.
AI isn’t stymying job growth, like headlines would have you assume. 79% of companies surveyed, who have adopted AI, said they’re hiring more because of it.
Mercury believes banking* should do more for the builders of the next great companies. Like, provide the intel you need to adapt in this market.
*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: Finding pattern breakers
From: Mario Gabriele
To: Mike Maples, Jr.
Date: Tuesday, October 7 2025 at 4:20 PM BST
Mike,
I’m sitting down with a cup of coffee, a stack of notes, and a well-worn copy of Pattern Breakers to begin this correspondence with you. It’s one that I’ve been looking forward to for some time, admiring your career for many years. That’s as much to do with the respect with which other investors talk about your work, as the formidable string of winners you’ve backed. You have always struck me as a true venture craftsman, with an unfakeable obsession for startups.
Reading Pattern Breakers only makes this sincere fascination more evident. I wish more exceptional investors would take the time to transcribe and distill their insights so thoughtfully. As you know better than I do, so much of early-stage investing relies on intuition and subtle signaling – a reality which often makes it difficult for even great practitioners to articulate their work. That can lead to the impression that venture capital is pure luck. No one can deny chance’s role, but to minimize it to spinning a roulette wheel misses the hazy art that the best have mastered.
Pattern Breakers is an insightful articulation of your version of the craft. It outlines the lessons you’ve deduced across twenty years of investing and countless hours of further research. It contains many wonderful observations I find myself mulling over regularly. One particular favorite is that great startups force a choice, not a comparison. As you note, Airbnb did not try to build a better version of the Four Seasons, but competed on entirely new terrain. While the Four Seasons promises to deliver a high-quality, consistent experience, Airbnb offers authenticity, giving travelers the chance to “live like a local.” Neither is inherently superior. Rather, they appeal to different customers and sensibilities. I’ve found myself returning to this heuristic repeatedly since I learned it.
To set the stage for our conversation, I’d love to dig into Pattern Breakers more deeply and examine the philosophies animating your investing. Rather than asking you to rehash the book’s major points (which I recommend readers enjoy wholesale), I wondered if we might try to understand its ideas “in action,” so to speak.
To paint a familiar scenario: Imagine a founder has walked into Floodgate’s offices to pitch you for the first time. How do you go about assessing whether you might have a pattern-breaking business on your hands?
I am sincerely interested in this at the most granular possible level. Do you prefer to sit directly across from an entrepreneur or kitty-corner to them? Do you prefer going for a walk to a formal pitch? Does it help you ask better questions to review materials beforehand, or do you want to hear everything fresh? To what extent are you analyzing small clues about their posture, attire, speaking speed, and so on? Are there any initial indicia that excite you? These might sound frivolous to some readers, but I’m increasingly of the opinion that these little details really influence the conversation you’re able to have.
We could spend a full other letter on questions alone. Which are among your favorites? (Bezos reportedly loved, “Are you a lucky person?” for example.) Which questions give you signal most frequently? You’ve noted before that you liked to ask, “Is this from the future?” What does that question tell you? How long does it take to realize a business might be truly special? How long do you take to make up your mind? What does your internal process look like to get to conviction? How much still, after all these years, comes down to feel? How much time do you spend analyzing the person versus the idea?
While reading your book, I found myself thinking about the tension between assessing an idea and assessing a person. Pattern Breakers covers both, but at least in my reading, it is primarily interested in the characteristics of game-changing ideas. You elegantly outline the importance of a startup building on (1) an “inflection” – some material technological, commercial, or sociological change, and (2) an “insight” around it. Lyft is a good example: Logan Green and John Zimmer recognized that smartphones with GPS were an inflection point, and then had the insight that this might enable a new kind of taxi network.
But you’ve remarked that 80% of your best investments came from pivots. Which makes me wonder: what signal do you get from a startup idea, knowing that it’s liable to change? Is it simply a proxy for a founder’s insightfulness and acuity? Are you using the current canvas to understand how their mind works? Or do you need to sincerely feel as if there’s an inflection and insight at the heart of it?
More broadly, what do you look for in a person? You’ve written about the importance of disagreeableness. Do you try to test for that explicitly? How so? Are there certain patterns you’ve noticed recur across outlier people? What shared alleles might you find if you put Ev Williams, Emmett Shear, Todd McKinnon, and Logan Green under a microscope? I am certain they have more differences than similarities, but equally convinced that there must be some unifying quality.
With much appreciation from one venture “anorak” to another,
Mario
Subject: When Tomorrow Shows Up Early
From: Mike Maples, Jr.
To: Mario Gabriele
Date: Friday, October 17 2025 at 7:40 PM PST
Dear Mario,
I really like your questions, because they get to the messy part of seed investing. It’s not about spreadsheets or pattern-matching. It’s about sensing whether someone is already living in the future and inviting the rest of us to catch up. You’re not just asking about mental models. You’re asking about the feel.
One of the first times I felt the future, I was in a Palo Alto cafe, and a 23-year-old Justin Kan walked in. He had a webcam strapped to a baseball cap and a mess of wires leading to a backpack. I was already skeptical. And that was before he said he planned to livestream his life. All of it. Twenty-four hours a day, like an internet reality TV show. It almost sounded like a prank.
But then he spun his laptop around, and there I was, live on the internet.
Suddenly, it felt different, and my curiosity started to take over. “How did you do that, and what’s in your backpack?” I asked. Justin opened it, and inside was a Linux computer, a video encoder, EVDO cellular hardware, and some Python code held together mostly with duct tape and conviction. But it actually worked, and keep in mind this was in 2007. YouTube had only existed for 18 months. Most people still had flip phones.
The cafe hadn’t changed, but my sense of possibility had. It didn’t feel like a pitch anymore. It felt like stepping through a portal to a different future. He wasn’t selling me. He was already living in a different reality and offering me a fleeting glimpse. And even though there were many pivots and years between Justin.tv and what became Twitch, the basic insight that millions of normal people would want to stream content was right, no matter how heavily disguised it was in the initial idea.
For a long time, I confused being early with being smart. Seeing things first felt like a superpower. But the seed investors that are rewarded most are not the futurists who can predict. They’re the ones who notice. Catching radically new futures feels less like investing and more like witnessing.
There are a few small habits I find helpful when I’m trying to catch a pattern-breaking future described by a founder:
Don’t label startups. The moment you call something “Uber for X,” you lose too much resolution to see what’s truly different about it. Labels turn messy ideas into something that fits into our current understanding, but they make you believe you understand things you don’t. The best startups break the current patterns of our current understanding. When you jump too quickly to a label, you’re more likely to miss the small, magical details that matter most.