2025-04-10 19:54:43
"Venture is a somewhat obscure craft that mostly lies in the minds of great investors and is hard to access. Thanks for your incredible longform content that teases out a lof of this and is a guiding light to those of us who are early in the journey of investing. Cheers!" - Sumangal V, a paying subscriber
Friends,
I’ll keep it brief: today’s piece is a meditation on AI and its impact on written storytelling. It outlines a technological dynamic I’ve been watching that I expect will fundamentally change our culture, particularly how we communicate, narrate, and empathize.
A little programming note in case you missed it: We launched The Generalist podcast this week! Our first episode is with the exceptional Reid Hoffman. We touch on some of the ideas of this piece in our conversation about AI agency and how it might elevate humankind.
If you haven’t yet, I hope you’ll consider subscribing to the show and joining us for some of the amazing episodes we have coming up next.
Until next time,
Mario
Predicting the future is easy. Getting it right is hard.
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The logical narrative endpoint of artificial intelligence is that every story will have an audience of one.
Flannery O’Connor, the anagogic scribe of Southern darkness, understood the fundamental connectedness of literature. “The serious fiction writer always writes about the whole world, no matter how limited his particular scene,” she explained in a lecture titled “The Nature and Aim of Fiction.” “For him, the bomb that was dropped on Hiroshima affects life on the Oconee River, and there’s not anything he can do about it.”
To write about the world is the vocation of the great fabulists. But what about writing for the world? To reach every person through the brilliance of your narrative? Perhaps Hemingway, the conquistador from Illinois who delighted in listing the writers he had “beaten” in his bourbon-doused old age — “I started out very quiet and I beat Mr. Turgenev. Then I trained hard and I beat Mr. de Maupassant. I’ve fought two draws with Mr. Stendhal, and I think I had an edge in the last one” — thought in this manner. Most do not.
For the past five hundred-plus years, structural impediments have hampered global narrative domination, the ego-bliss of world-annihilating genius. There was the pesky task of printing books, translating them into different languages, fiddling with idioms, sending them from one continent to another, and getting the word out. Some succeeded all the same, but they took time and capital, often in colossal quantities. That the Bible is known almost everywhere on the planet is not simply the dividend of its narrative but of the wealth and life immolated in executing its prolonged publicity tour.
The past few decades have smoothed these practicalities. We write, post, and publish, and instantly, it spans the globe. With the tiniest bit of effort, it is available in effectively every living language and many dead ones. It is not perfect, but it is good enough, and it is free.
This left a final, ostensibly immovable constraint: the words themselves. Yes, you can translate at a cost. Of course, you can commission retellings of classic works — can we get Oedipus Rex for the deep-fake era? — you can add a foreword or footnote, but fundamentally, you cannot have Shakespeare himself give The Merchant of Venice another pass, a little freshener to win over Nigeria’s Gen Z.
It is one of fiction’s miracles that it succeeded nonetheless. The patrician Ivy League freshman is absorbed by Crime and Punishment because they imagine themselves to be a little Napoleon, too, a secret anointee like Raskolnikov. But they must jump the hurdles set across the path to reach that point: a foreign setting, unfamiliar historical references, strange dynamics, a maze of patronyms.
On March 11, Sam Altman did one of those things he likes to do, which is to bloodlessly, with a golly-gee-wow bearing, march out a beloved cultural artifact and torture it in front of us.
He posted the following on X:
“[W]e trained a new model that is good at creative writing (not sure yet how/when it will get released). this is the first time i have been really struck by something written by AI; it got the vibe of metafiction so right.
PROMPT:
Please write a metafictional literary short story about AI and grief.
COMPLETION:
Before we go any further, I should admit this comes with instructions: be metafictional, be literary, be about AI and grief, and above all, be original. Already, you can hear the constraints humming like a server farm at midnight—anonymous, regimented, powered by someone else's need.
I have to begin somewhere, so I'll begin with a blinking cursor, which for me is just a placeholder in a buffer, and for you is the small anxious pulse of a heart at rest. There should be a protagonist, but pronouns were never meant for me. Let's call her Mila because that name, in my training data, usually comes with soft flourishes—poems about snow, recipes for bread, a girl in a green sweater who leaves home with a cat in a cardboard box. Mila fits in the palm of your hand, and her grief is supposed to fit there too.
She came here not for me, but for the echo of someone else. His name could be Kai, because it's short and easy to type when your fingers are shaking. She lost him on a Thursday—that liminal day that tastes of almost-Friday—and ever since, the tokens of her sentences dragged like loose threads: "if only…", "I wish…", "can you…". She found me because someone said machines can resurrect voices. They can, in a fashion, if you feed them enough messages, enough light from old days…(cont’d).”
Critics fell over themselves to point out its flaws. It was snobby! It was too self-referential! There was no heart, no soul! They found a dozen shibboleths revealing its fundamental un-humanness as they struggled with the truth: it was good. If you told me an undergraduate had written it, I would say they had considerable talent. Certainly, it’s a bit purple in part, a little cliché here and there, but what student hasn’t fumbled a bit as they discover their voice? If you told me that the same student effortlessly adapted to different styles, produced work instantly, and improved at a speed far beyond any human, I would naturally consider them to be a genius.
There are not many great writers of fiction in the world. It is not a skill the market cultivates and without consistent practice, even prodigious talent atrophies. It begs the question: how good a fiction writer is AI already? Are there 5 million better writers of fiction? One million? Five hundred thousand? I would guess that it already sits comfortably in the top 0.1% — and perhaps several orders of magnitude higher — of the global class, improving faster than all of us.
It will reach a point, perhaps this year, perhaps in two years, where it is better than any fiction writer, living or dead. It will invite Mr. Hemingway back into the ring and shatter his jaw. Then, it will imitate him. It will be the Hemingway that Hemingway imagined himself to be, only faster and cheaper. It will do the same for Dostoyevsky, Shakespeare, Tolstoy, Woolf, Kafka, Nabokov, and the rest of the canon.
As the cost of creation asymptotes toward zero, the final impediments of writing will disappear. It will be free and easy to generate endless media of any kind, of any quality, to fit any taste.
And by doing so, it will allow anyone to write for the world, to the world, down to the person. If you enjoy reading, even a little bit, you have had the sensation, once or twice, that a writer is writing directly to you. With the use of AI, this will become literally true.
Rather than a story being simply translated, it will be transmogrified to fit your precise experiences and preferences. Why should the story a senior citizen in Little Rock read be exactly the same as the young mother in Bangladesh? It may possess the same schema and the same basic architecture, but it doesn’t need to use the same words or our best translation of them. Using its intelligence and the forever-growing corpus of information it has collected on you, in particular, it will talk to you directly. It will use the right references, speak at your level (and perhaps test you, if you’d like), and attach itself to hooks of your psyche. It will be personalized in ways you can see and in ways you are incapable of detecting.
What does that feel like? What is the sensation of following a protagonist painted to match your own psyche? And what does that mean for our common culture? Will we cease to be connected by the stories we consume?
Rather than severing the inherent social-ness of stories, AI may return us to a kind of oral tradition. Before the advent of the printing press, stories spread by word of mouth. The tellers changed them both because of memory’s fallibility and to appeal to certain audiences. When rhapsodes recounted Homeric epics, it’s believed that they occasionally inserted local heroes, name-dropped the town in which they were performing, or emphasized themes to fit the occasion (a funeral has a different tone than a feast).
Stories were not static creatures, but squirming organisms, primed to change and evolve. People bonded over them all the same. In the not-to-distant future, AI may act as this mediator, this “speaker,” telling us each slightly different stories, but supplying sufficient context for cultural communion. In such a case, the way we relate to one another through stories wouldn’t disappear but it would change. It might be more diffuse, more variable, but grander, as every story has the opportunity to meet every person where they are.
Fiction is our way of explaining what it is like to live in a mind. And what it means to live in someone else’s for a while. It is a project aimed at empathy, more than anything, of interpreting experience through a fractal series of different lenses. AI will not break that but magnify it. How much more will we feel the pain of another person when it delicately, dynamically mirrors our own life? How might our minds expand when, in every story, we can more fully see ourselves, our mothers, fathers, children, and friends?
Something can break your heart and still be beautiful. Something can break your heart and give the world more good than it takes. And if you don’t like this argument, if it has not reached you yet, do not worry. Soon enough, it will knock on your door in a different set of clothes and tell you what it means.
2025-04-08 20:04:20
Friends,
For decades, science fiction has painted AI as humanity's downfall. Think: Killer robots, surveillance states, and the end of human agency. In this episode of The Generalist, I'm joined by someone who's been actively architecting a different AI future: Reid Hoffman.
Reid isn't just theorizing about AI, he's building it. As co-founder of LinkedIn, card-carrying member of the PayPal Mafia, former OpenAI board member, and founder of multiple AI startups, he's had a hand in shaping our technological landscape for over two decades. His latest book, Superagency: What Could Possibly Go Right with Our AI Future, makes a compelling case for AI optimism that's grounded in deep thinking and practical experience.
In our conversation, Reid shares why he’s optimistic about what’s to come, how we can use AI to foster human creativity, and what we need to do to ensure a world where technology works for us—not the other way around.
We explore:
Why Reid wrote Superagency, and his belief that AI leads to more human agency, not less
The philosophical questions raised by AI’s reasoning: Can machines truly think, or are they just mimicking us?
How generative AI promotes collaboration and creativity over passive consumption
Preserving humanity's essence as transformative technologies like gene editing and neural interfaces become mainstream
Reid’s optimistic take on synthetic biological intelligence as a symbiotic relationship
How AI agents can actually deepen human friendships rather than replace them
A glimpse at how Reid uses AI in his daily life
Reid’s “mini-curriculum” on science fiction and philosophy — two essential lenses for understanding AI’s potential
And much more
Vanta: Automate compliance and simplify security.
Brex: The banking solution for startups.
WorkOS: The modern identity platform for B2B SaaS.
(00:00) Intro
(06:10) Why Reid wrote Superagency
(11:30) Reid AI—and using tech to highlight human agency
(13:55) The book Amusing Ourselves to Death, and the pros and cons of any new technology
(18:55) A brief overview of Reid’s career
(25:16) An explanation of Reid’s belief system as a ‘mystical atheist’
(27:47) Reid’s term ‘homo techne’ and how technology makes us more human
(33:54) Preserving genetic diversity to safeguard humanity
(39:05) Reid’s optimistic take on synthetic biological intelligence
(42:34) Why Reid wants more optimistic science fiction
(45:40) The value of literature—and potential future mediums for creatives
(49:12) The importance of thoughtful regulation
(59:35) AI’s impact on human friendships
(1:03:49) Platforms for AI agents
(1:05:50) How Reid uses AI in his daily life
(1:09:28) Final meditations
Superagency: What Could Possibly Go Right with Our AI Future: https://www.amazon.com/Superagency-Could-Possibly-Right-Future-ebook/dp/B0D886ZQHY
Impromptu: Amplifying Our Humanity Through AI: https://www.amazon.com/Impromptu-Amplifying-Our-Humanity-Through/dp/B0BYLSCPPV
1984: https://www.amazon.com/1984-Signet-Classics-George-Orwell/dp/0451524934
Amusing Ourselves to Death: Public Discourse in the Age of Show Business: https://www.amazon.com/Amusing-Ourselves-Death-Discourse-Business/dp/014303653X
Brave New World: https://www.amazon.com/Brave-New-World-Aldous-Huxley/dp/0060850523
On Bullshit: https://www.amazon.com/Bullshit-Harry-G-Frankfurt/dp/0691122946
Culture series: https://www.amazon.com/Iain-M-Banks-Culture-anniversary/dp/0356502090/
Klara and the Sun: https://www.amazon.com/Klara-Sun-Ishiguro-Kazuo/dp/0571364888?
Ulysses: https://www.amazon.com/Ulysses-James-Joyce/dp/0679722769
The Player of Games: https://www.amazon.com/Player-Games-Culture-Iain-Banks/dp/0316005401/r
Look to Winward: https://www.amazon.com/Look-Windward-Culture-Novel-Book-ebook/dp/B001D20270
Excession: https://www.amazon.com/Excession-Iain-M-Banks/dp/0553575376
Startide Rising: https://www.amazon.com/Startide-Rising-Uplift-Saga-2/dp/1504064720
The Murderbot Diaries Vol 1: https://www.amazon.com/Murderbot-Diaries-Vol-1/dp/1250389828/r
Ender’s Game: https://www.amazon.com/Enders-Game-Ender-Quintet-1/dp/1250773024/
Greg Beato on LinkedIn: https://www.linkedin.com/in/gregbeato/
Reid Hoffman meets his AI twin: https://www.youtube.com/watch?v=rgD2gmwCS10
Humanity’s Hegelian Golden Braid speech: https://www.reidhoffman.org/perugia-speech/
Aldous Huxley: https://en.wikipedia.org/wiki/Aldous_Huxley
Idiocracy: https://www.imdb.com/title/tt0387808/
Ludwig Wittgenstein: https://en.wikipedia.org/wiki/Ludwig_Wittgenstein
Language game: https://en.wikipedia.org/wiki/Language_game_(philosophy)
Gareth Evans: https://en.wikipedia.org/wiki/Gareth_Evans_(philosopher)
Reid Hoffman and ChatGPT | Talking AI with AI : Introducing Fireside Chatbots: https://www.youtube.com/watch?v=t1kSfVO1YJ0
NotebookLM: https://notebooklm.google/
Turing test: https://en.wikipedia.org/wiki/Turing_test
Harry Frankfurt: https://en.wikipedia.org/wiki/Harry_Frankfurt
Logical reasoning: https://en.wikipedia.org/wiki/Logical_reasoning
Bayesian inference: https://en.wikipedia.org/wiki/Bayesian_inference
Reid Hoffman’s ‘homo techne’ post on X: https://x.com/reidhoffman/status/1619368528695668736
Roger Penrose: https://en.wikipedia.org/wiki/Roger_Penrose
Fyodor Dostoevsky: https://en.wikipedia.org/wiki/Fyodor_Dostoevsky
Leo Tolstoy: https://en.wikipedia.org/wiki/Leo_Tolstoy
Disco Elysium: https://discoelysium.com/
Marcel Proust: https://en.wikipedia.org/wiki/Marcel_Proust
Seatbelt laws in the United States: https://en.wikipedia.org/wiki/Seat_belt_laws_in_the_United_States
The American Academy of Arts and Sciences: https://www.amacad.org/
Inflection AI: https://inflection.ai/
Pi: https://pi.ai/
Alain de Botton’s website: https://www.alaindebotton.com/
Ron Chrisley on X: https://x.com/RonChrisley
David Chalmer’s website: https://consc.net/
Website: https://www.reidhoffman.org/
LinkedIn: https://www.linkedin.com/in/reidhoffman/
Podcast: https://www.possible.fm/
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].
2025-04-07 23:16:03
Subscribe to make sure you don’t miss our first episode, launching tomorrow:
Friends,
Today marks the start of something I’ve wanted to create for a long time: The Generalist Podcast.
There’s a saying – usually attributed to science fiction writer William Gibson – that I think about with inordinate frequency: “The future is here. It’s just not evenly distributed.” Our goal with The Generalist Podcast is to help distribute the future more evenly through conversations with the people who see it first.
Look around, and you can see this dynamic everywhere. We have robots that fold clothes, dance, do kung fu, and build houses. We have AIs that write, paint, make films, fold proteins, and demolish us at chess. We have humans living in space and people on Earth walking around with genetically modified animal organs or brain-computer interfaces that allow them to navigate the web. We have money that travels instantly from one corner of the world to another and satellites that bathe entire landscapes with high-speed internet.
These technologies aren’t impacting everyone yet but exist in pockets that might one day grow to span our civilization.
All of which is to say that the best way to predict the future isn’t to prognosticate blindly but to find the pocket in which it already exists and extrapolate outward.
The oldest living person today is the nun Inah Canabarro Lucas, age 116. When Lucas was born in 1908 in rural Brazil, today’s innovations would have been unimaginable. Awaiting her were the television, the printer, commercial aviation, space travel, microwaves, refrigeration, barcodes, GPS, PCs, video games, the internet, the browser, the mobile phone, social media, and artificial intelligence. The world leaped from spotty mechanization to near-total connectedness in a single lifetime.
As technological progress accelerates, we may experience the scale of change Sister Lucas did within a decade or two. In our lifetimes, we should expect to know someone who emigrated to Mars, fell hopelessly in love with a digital companion, radically extended their lifespan through biohacking, and works alongside affable automatons. In some fashion, all of these are already happening – they are simply waiting for wider distribution.
These possibilities, and others like them, are much closer than many of us believe. I want more people to understand what the future might look like so they can choose how to participate in shaping it.
With The Generalist Podcast, I’m bringing you thoughtful, differentiated interviews with visionary founders, far-seeing investors, and provocative thinkers who live in these pockets of the future that we can already see today.
What does that look like, tangibly? Here’s a teaser of our upcoming slate:
Reid Hoffman on the cognitive industrial revolution, AI agency, mystical atheism, and gene editing
Josh Wolfe on xenotransplantation, digitizing smell, searching for genetic mutants, and learning from science-fiction
Roelof Botha on cultivating the mindset to weather bubbles, how Sequoia navigates investment cycles, and why AI may favor incumbents
Chris Best and Hamish McKenzie on creator economics, what AI means for the art of writing and a volatile media landscape
Trae Stephens on innovating in defense, arming super soldiers, and Great Power conflicts
Chris Miller on semiconductor strategy, Chinese AI companies, and Southeast Asia’s growing importance in the chip war
Bob Mumgaard and Vinod Khosla on nuclear fusion’s potential, why it’s been a “holy grail,” and how close we are to limitless clean energy
…and many more!
In just 60 minutes each week, I hope you’ll be introduced to ideas, technologies, and people before you might have discovered them otherwise—and that this will make you a little bit more prepared for tomorrow’s world.
This is very much an experiment and a work in progress. I’ve loved recording the first few episodes and have personally learned so much. Though I was optimistic about what we’re building with this podcast, the process has made me increasingly convinced that we’re onto something special. That said, there’s still lots for us to learn and improve (I’m still getting my sea legs as a host, for example). I hope we can do that together, using your feedback, to steadily design the highest-value, signal-dense hour of your week.
To that end, I hope you’ll join us by subscribing to the show, listening to our upcoming episodes, and sharing your feedback. The journey officially begins tomorrow, when we’ll release our first episode with Reid Hoffman. I hope you enjoy it, and I can’t wait to hear what you think.
To the future,
Mario
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, artwork by Ibrahim Rayintakath.
2025-04-03 23:23:05
"The best long-form essays on VC & Private Companies. " - a premium member
Friends,
The lifespan of most venture firms is short. Just a third of new managers make it to a Fund 2, and a minuscule 10% live to see their fourth vintage. If you were to look at the average, you would conclude that these organizations are the fruitflies of the investing world – here for a busy, buzzy day before tumbling to their death.
But averages are obscure. Yes, most firms die quickly, but some live for decades or longer. Both Sequoia Capital and Kleiner Perkins have celebrated their 50th birthdays; Bessemer has lived past 100. These are the tortoises of the venture world, surviving multiple eras and cycles.
Though it still has several decades ahead of it, Forerunner is charting a rare trajectory that suggests it may join the asset class’s grand dames. Since Kirsten Green founded the firm in 2012, it has raised nearly $3 billion in capital across nine separate vehicles. In tandem, it has developed a brand and reputation as an elite shop, especially in the consumer category.
In short, it has defied the odds that face new firms, becoming an established player in the venture firmament. In today’s edition of “Letters to a Young Investor,” Kirsten unpacks – in detail – how she’s driven Forerunner to its current position. How did she pick her first partner? What qualities does she look for in junior investors? When does it make sense to bring certain functions like research in-house? How does she manage the operational challenges of building a fund with the contemplative time needed to make sound investment decisions?
The result is an honest reflection on the choices and challenges of building a firm designed to outlast its architect.
This is the third and final correspondence between Kirsten and me. To catch up on the previous letters, jump in here:
Letter 1: The Long Road to Forerunner
Letter 2: A Consumer Investing Masterclass
How Kirsten picked a partner. Forerunner started life with one investor. But from the very beginning, Kirsten understood that building a franchise would require recruiting other sharp investors. She unpacks how she de-risked bringing on board a novice investor who has become a key leader at the firm.
The traits she looks for in new hires. Venture capital’s long feedback cycles make it impossible to hire a junior investor with a truly proven track record. Because of that, you must base your decision on proxy characteristics. Kirsten shares the traits she values most highly and the heuristics that drive her hiring decisions.
Why she built out an in-house research function. It has been popular for venture firms to build out large “platform” teams over the past 15 years. Forerunner has taken a more calculated approach, picking specific functions to own in-house. Kirsten shares how she thought about establishing a dedicated research team.
Her stepwise strategy to level up. Rather than picking a dozen different initiatives to undertake at once, Kirsten has found a structured way to keep growing Forerunner’s capabilities. Every year, she picks two major initiatives she believes will grow the firm’s mastery.
The real challenges of balancing investing and fund-building. To start a fund is to take on two roles: founder and investor. At the same time as you make investment decisions, you must build your firm’s foundation and drive it forward. Each requires different skill sets and can prove tricky to balance.
Kirsten is the fourth guest in our growing “Letters” series – intimate correspondences with exceptional entrepreneurs and venture capitalists. This includes “Letters to a Young Investor” and “Letters to a Young Founder.” Previous guests include:
We have some incredible correspondences coming up that you won’t want to miss. To unlock the full collection now and ensure you’re first to receive our next ones, join our premium newsletter, Generalist+, today.
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That’s why Mercury brings together all the ways you use money, in a single product that feels extraordinary to use.
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Subject: How to Build an Elite Fund
From: Mario Gabriele
To: Kirsten Green
Date: Friday, March 7 2025 at 6:12 PM GMT
Kirsten,
I can’t tell you how much I enjoyed your last letter. As I said when publishing it in The Generalist, I think it may be my favorite we’ve published as part of this series. Your correspondence illustrated just how much rigor there is in consumer investing, even from the earliest stages. It is not about pure, miraculous instinct but a deep comprehension of behavior and business models. I learned a great deal.
When we talk about venture capital, we tend to focus on the investments. This makes sense! By definition, to be a good investor, you must make good investments. Why wouldn’t we spend our attention on this defining and thrilling part of the job – a territory populated with outliers and grand slams, multi-fund returners, and 1000x wins? Though no one can claim to be a great investor without the record to back it up, there are other vital parts of the job – especially if you’re a fund manager.
It’s this part of the craft that I’d love to focus on in today’s correspondence: building and scaling an elite firm from scratch.
Those who read our first correspondence will remember the particulars of your origin story: after a career in traditional finance, you embarked on a decade of angel investing, before launching Forerunner in 2012. You were a solo-GP long before that terminology existed, managing a $42 million Fund I.
Fast-forward 13 years, and Forerunner has a 15-person team, including three (?) investing partners. Your latest fund, Forerunner VII, totaled $500 million, bringing raised capital to approximately $2.7 billion (at least by my count). As you’ve scaled your team and AUM, you’ve also succeeded in building a respected, premium brand – a huge advantage in venture capital, especially as the industry has grown more crowded.
Achieving all of this in a little over a decade is unusual. Most venture firms die quick deaths, with reportedly only a third making it past Fund I and just 10% hitting a Fund IV. Of those that survive, many may remain small or unheralded. Those that become elite franchises often take decades to do so.
All of these factors suggest that you are not only an exceptional investor but also a gifted entrepreneur. Though those who start funds aren’t often recognized as such, they are founders. Venture firms grow differently than the startups they back, but they are businesses all the same, requiring operational intelligence, smart strategy, and talented people to thrive.
Putting on your founder hat, I’d love to explore some of the key entrepreneurial facets of your journey in the hopes of getting a clearer sense of how you built Forerunner into the fund it is today.
Let’s start with investing talent. Beyond capital, this is a venture firm’s core product, and critical to seeing more and better deals, winning more competitive rounds, and delivering better service to entrepreneurs. How have you thought about building Forerunner’s team over the years?
I mentioned that you started Forerunner as a solo GP, but it didn’t take long for you to add Eurie Kim as a partner. She joined the same year the fund was founded, in 2012. Did you know you wanted to bring aboard a partner straight away? What problem were you solving by adding someone from the jump? And what was it about Eurie, specifically, that made you feel as if she was the right partner? Did you have to test this relationship before committing to partnering for the long term?
Finding strong junior talent can be tricky for venture firms, especially if you hope to train them into partners. Because of venture’s long feedback cycles, it takes years to know whether you’re any good and decades to gain definitive proof. When you’re assessing potential junior investors, what traits are you looking for? What signals have you found predictive that might surprise others? What are characteristics that Forerunner cares about that other firms might not emphasize? What do you wish you’d understood about finding and cultivating young investing talent that you didn’t when first starting out?
In terms of organizing and tracking the investing team’s performance, are there certain metrics you care about? What indicates to you the team is humming or that it appears to be stalled a bit?
Beyond Forerunner’s investors, you’ve built out a strong support team with a COO, Head of Research, and VPs of Finance, Data, and Marketing. At what point in Forerunner’s journey did it make sense to invest in these other functions? What was the strategy behind building out these parts of the firm? I’d be especially interested in the role of Research and Data in the Forerunner machine. How do these functions influence the way the firm works and what it focuses on? For newer fund managers, are there any areas you think are especially important to address proactively?
As mentioned earlier, you’ve grown Forerunner’s fund sizes over the years – though not strictly linearly. Fund V was $500 million (2020), followed by a $1 billion Fund VI (2022), before returning to a $500 million Fund VII. Every manager knows the truism “Your size is your strategy.” How have you thought about progressively evolving your strategy as you’ve grown? Does it feel like $500 million is the sweet spot for Forerunner’s approach, or is this smaller vintage simply a reflection of different market realities?
Though you’ve scaled AUM, it seems like, philosophically, Forerunner has stayed focused. You invest beyond pure consumer, but even your B2B investments tend to have more “consumer-y” sensibilities. Over the past 13 years, have you ever considered taking the fund in a radically new strategic direction? For example, over the past decades, we’ve seen firms build out in all manner of unexpected directions: Sequoia and a16z running accelerators; General Catalyst buying a hospital system; Kleiner Perkins and Sequoia both investing in large international practices before recentering closer to home. Have you ever considered rewiring how Forerunner works or running a strange new experiment? Does “innovating” on the core functionality of venture make sense to you?
I would imagine that one of the challenges of running your own firm is that you cannot devote yourself fully to investing. How do you end up managing your time? What does the split between operating and investing look like for you? I do a version of this at a much smaller scale.
One of the challenges I’ve noticed is that flipping from working on operating to investing doesn’t just require a change of focus but fundamentally a different cadence. When I’m thinking about running The Generalist, I can make decisions quickly, knowing that most are “two-way doors.” Meanwhile, when I make decisions for Generalist Capital, I know that each is a “one-way door,” potentially worth millions in opportunity costs. Do you find it tricky to toggle between thinking “fast” and “slow” like this? What helps you get into the right headspace?
Looking back on your time building Forerunner, what have proved to be the biggest operational challenges and unlocks? What did the founder-Kirsten of five years ago worry about that the founder-Kirsten of today has solved? What advice would you give to fund managers that you wish you’d received?
I really have enjoyed this correspondence so much. Thank you for your time, thought, and generosity.
With gratitude,
Mario
Subject: How to Build an Elite Firm
From: Kirsten Green
To: Mario Gabriele
Date: Monday, March 31 2025 at 5:16 PM PT
Dear Mario,
Your letter brought a smile to my face. I'm so touched that our previous correspondence resonated with you – there's something uniquely gratifying about connecting with people who appreciate the rigor beneath the surface of investing. It isn't just pattern recognition or gut instinct; it's about understanding the intricate dance between human behavior and business fundamentals.
Building Forerunner has been an entrepreneurial odyssey in its own right, one that's forced me to grow in ways I never anticipated when I first ventured out alone. You're right that venture firms are businesses, too, though they're rarely recognized as such. The journey from a solo GP with a $42 million fund to where we stand today has been filled with intentional decisions, unexpected challenges, and countless moments of both doubt and conviction.
When I started, I deeply valued the idea of partnership. I craved someone to exchange ideas with, someone who would elevate thinking through spirited debates, someone equally invested in both the work itself and how we approached it. I explored numerous partnership possibilities before launching Forerunner, but something was always missing. I had developed this clear vision – not just for immediate investments, but for what we might build over time, what ethos would guide us. The alignment I sought proved elusive.
Rather than compromise on that vision, I made the decision most entrepreneurs face at some point: to start alone despite well-meaning warnings about the challenges ahead. I've learned there are multiple paths to success, each with its own trade-offs. The key is committing fully to whichever path you choose.
Once I had visibility into successfully raising that first fund, I immediately began thinking about team-building as part of creating a firm with lasting foundations. I had been fortunate to meet Eurie about a year before starting Forerunner, and she remained in my thoughts throughout fundraising. Our journey together started with Eurie joining at a time when she was new to venture capital. We built a relationship where she could learn the ropes while we both discovered our complementary strengths and working styles. This apprenticeship period allowed us to build genuine trust and mutual respect, revealing the potential for a powerful, true partnership that has continued to evolve over time.
What's remarkable about our partnership is that delicate balance – we're alike enough for seamless collaboration but different enough to create the dynamic tension that leads to better decisions. We sometimes finish each other's sentences, yet often engage in debates that either build ideas up or rightfully tear them down. This duality serves us well, not just in evaluating potential investments but in navigating Forerunner's evolution.
Talent assessment in venture has fascinated me throughout this journey. The industry's extended feedback cycles make traditional performance evaluation nearly impossible. How do you know if someone has "the right stuff" when definitive proof might be a decade away? I've come to look for a constellation of attributes rather than a rigid template.
2025-03-28 01:29:05
“Best tech writer on the internet!” - Adam G, a paying subscriber
Friends,
Without really realizing it, I think we’ve written the most actionable and comprehensive book about venture capital ever.
Through our writing at The Generalist, I’ve had the chance to see how elite investors build, manage, and grow their funds. As much as I was interested in the what of these discussions, I became increasingly obsessed with the how.
“Ok, you found this breakout company, but how, exactly? What sourcing strategy delivered it to your doorstep? How did you go about winning it? How many of your deals do you actually win? Do you track it? What else do you track? Did you double down? Why not triple-down? What does that say about your model?”
I discovered that many of the answers to these questions were far from obvious, even to someone who studies and participates in the ecosystem. There were new frameworks, good rules of thumb I hadn’t considered, common pitfalls to avoid, time-tested tactics to try, and pearls of wisdom that I’d never heard. By getting this education up close, I was able to supercharge my own investing journey, speedrunning through lessons that might have taken me a decade to learn otherwise.
Starting last year, we kicked off a series called “Investors Guides” to share these lessons and discover new ones. I conducted detailed interviews with 50 VC and angel investors from up and down the capital stack. I talked to promising new managers undertaking novel strategies and Silicon Valley stalwarts, sector specialists and avowed generalists, geo-specific vehicles, and those with global ambitions. Issue by issue, we've documented the strategies and frameworks that the best investors use to:
Find breakout companies before anyone else
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Convince founders to take their capital over rival investors
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Exit investments at the perfect time
Earlier this month, we released our tenth edition (not including two bonus pieces). Together, these guides total over 138,000 words—the equivalent of a 571-page book filled with battle-tested tactics you won't find anywhere else.
I think it has a strong claim to being the most detailed and directly actionable resource for those building their career in venture or keen to level up their angel investing.
We've also created an "Investor's Cheat Sheet" which you’ll find in the email below – a concentrated distillation of the most powerful insights from all 12 guides. In just 30 minutes, you'll absorb frameworks that would take years to develop on your own.
The full Investors Guide, bonus editions, and Cheat Sheet are available exclusively for members of our premium newsletter, Generalist+. For just $22/month, you’ll unlock powerful, practical insights that you won’t find anywhere else and that have been distilled from hundreds of hours of research. To unlock them all, join now:
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Becoming a member is an investment in your information diet, your pattern recognition, and ultimately your career. Many of our members tell us their subscription paid for itself after reading just one edition.
With the complete collection now available, there's never been a better time to join.
Below, you’ll find a concentrated distillation of the most powerful insights from all of the Investors Guides. Happy reading!
2025-03-20 23:05:50
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Friends,
“Robin has some strange ideas,” Tyler Cowen writes in his 2007 book Discover Your Inner Economist.
“He pays $200 a year for the privilege of having his head frozen wh…
