Long letter. lots of links. still can’t type. ball up top.

NY CoS/founding biz hires

I’ve got three portfolio companies hiring for founding biz/ops/chief of staff roles in New York right now. Getting the right person to help build each of these businesses is very important to me.

• A defense-adjacent manufacturing platform is looking for a chief of staff to be the engine behind their acquisition strategy. This company is led by a repeat founder who’s building AI to acquire and transform specialized electronics manufacturers. You’ll build growth buyout models that blend traditional GBO mechanics with software-driven operational improvements, lead diligence on targets, structure transactions, and serve as analytical thought partner to the CEO. 5-7 years in IB and/or PE required, industrials/manufacturing experience required.

• A dev tools company betting that the AI platform shift creates a once-in-a-generation opportunity to replace foundational infrastructure is hiring a founding business generalist. The technical founder is building what could become the new standard for how humans and AI collaborate on code. He needs a right hand to run day-to-day operations while he does deep product work and closes F500 deals. Startup background is a must.

• A vertical AI company building a self-driving network of agents for healthcare is looking for a gap filler/an extension of the CEO. This repeat founder has a compelling theory: LLMs make it possible to embed agents directly into existing workflows without behavior change or new tooling. The company is already moving tens of thousands of transactions and expanding fast. Prior startup experience required, open to new/recent grads with the right intensity.

Each of these companies is well-funded and led by a very experienced founder. These are opportunities for ambitious grinders to get in early at companies we’re extremely bullish on. They’re all still operating in stealth so if you’re interested, reply directly with your Linkedin and a one sentence blurb.

It goes without saying that each of these companies is also hiring engineers. The dev tools company in particular is looking for Rust engineers.

Nash equilibrium (defection)

Chris Paik wrote one of my favorite recent overviews/takes of the current venture market in psychology.

TLDR: there’s basically no upside in being disciplined, honest, self-critical, etc and disproportionate upside with relatively minimal downside to doing/being the opposite of all of those. I don’t mean to just totally black-pill everyone. I think it’s possible to carve out a lane doing things “the right way” but it requires having an investment culture and a set of very high-trust LPs. It is objectively harder and only works for the love of the game but may not be the EV-maximizing strategy.

The whole thing is worth reading (it’s two pages)but this section in particular is the most striking to me and gets at one of the core anxieties/debates.

From Chris:

The Nash Equilibrium of Defection

-If You Cooperate (Discipline) and They Defect (Chase): Your competitor wins the “hot” logo. They get the press, the markup, and the reputation for “access.” You are left with a “disciplined” portfolio of obscurities. LPs view you as irrelevant. You fail to raise your next fund.

-If You Both Defect (Chase): You both bid up the asset. Valuations skyrocket, pricing out future upside. Returns for the vintage regress to the mean. However, you both survive to play another round because you both have “access” to the category winners.

In this game, Chasing Momentum is the Nash Equilibrium. The penalty for missing the boat (career risk) is immediate and severe, while the penalty for overpaying (return risk) is delayed by 7–10 years. Therefore, no rational GP can afford to be the only disciplined investor in a momentum market.

Chris and I have yet to have a chance to work closely together though I hope that changes. He seems like a really sharp guy.

The roll-ups are still rolling

I spoke to Madeline Renbarger of Newcomer for her piece about VC-funded buyouts and roll-ups. I’ve written about this many many times before. But I think it’s worth reiterating the difference between what we’re doing and what the mega funds are doing:

The big distinction is leading w capital vs leading w product. We want to fund product companies that go to market by buying operating companies and they want to buy businesses.

We fund product 0 to 1 development to ensure that founders can underwrite transformational outcomes from future acquisitions rather than going on a buying spree before understanding where they are differentiated owners. So often that means a typical seed round upfront.

This helps preserve a lot of optionality to either remain a software company, build an operating company, buy operating companies, or some combination thereof. We’ve seen instances where businesses expected to buy companies and instead found that they can succeed by building an operating business themselves without any need for M&A at all. Leading with capital is like building a sales team before you have a product.

from the article:

Slow Ventures has funded several roll-up startups without putting up a lot of upfront capital. Instead, Slow looks to seed companies to build the AI tech needed for these roll-ups, but the founders then raise additional capital to fund these large-scale acquisitions.

Slow invested early in Teamshares, which buys up small businesses using a model that enables employees to gain an equity stake after the owners sell. Teamshares said in November that it plans to go public via SPAC. Slow was also an early investor in Metropolis, which raised a $1.6 billion equity and debt round this fall to roll-up parking lots and automate check-out with AI.

Read the Slow GBO deck here.

Creator 2025

This deck from Megan and the Creator team goes over the five important themes for creators this year:

1. People matter, brands don’t

2. Own the niche, not the category.

3. Build worlds, not products.

4. AI culls the undifferentiated

5. Short the mass market.

From their letter:

In February of this year, we closed and launched Slow Ventures Creator Fund I on the heels of a simple idea: the next great companies would be built by creators. Not celebrities or influencers, these creators are capable builders with real trust, informed insight, big ambition, and an instinctive grasp of community, storytelling, and distribution.

This fund not only represents years of quiet iteration and foundation building, but importantly, is the first institutional fund backing creators directly with seed capital. We are grateful to have LPs like MIT, University of Michigan, TIFF, Rutgers and many others support our pursuit to fund this new path for entrepreneurship.

This deck recaps much of what we’ve observed in our first year: the themes that matter as well as the ones that don’t. The best creator businesses don’t chase views, they expand their niche expertise into new worlds. They turn narrative into community, community into revenue, and revenue into durable companies. Our early investments in Jonathan Katz-Moses, Steven Bartlett, Tayla Cannon (and more!) show that this model unlocks multi-product franchises rooted in trust, mission, and execution.

Technological and cultural shifts have rewritten the means of attention, influence, and consumption, which have fundamentally changed where value is created, captured, and funded. We are in the era of the individual. But in a world of frictionless scale, the winners won’t be the loudest. They’ll be the creators who know exactly why their audience shows up and who leverage their communities to solve real problems.

Cyber Dinner

​AI is breaking $1.5T of security market cap.

​For 30 years, cybersecurity has worked because attacks have had known limitations. Businesses have also had a concept of control: how to secure within a perimeter, how to vet vendors, and how to remediate gaps or accept known risks. The $1.5T security market cap was built on the assumption of visibility and control. That known landscape is gone with AI.

This winter I’m teaming up with ex/ante and Outtake to host a dinner and discussion about the changing threat landscape and how new and existing security companies will meet that.

Sign up to join here.

Abundance

I’ve spent the last year supporting and working with Abundance New York. This is a great organization working to build a more vibrant and dynamic New York led by people who believe our powers are rooted in growth and change.

In 2025 Abundance New York:

• Won high-friction policy fights. Helped get congestion pricing back on track and passed City Charter amendments enabling fast-track rezonings and up to 130% increases in housing capacity.

• Unlocked housing supply. Backed City of Yes and key rezonings in Midtown, LIC, and Jamaica, and pushed the Brooklyn Marine Terminal plan through delivering 6,000 homes (40% affordable).

• Built reach and leverage. Grew to 4,300 members across 45 Council districts, generated ~$800k for aligned candidates, and launched a voter guide viewed 375k+ times that filled a real civic vacuum.

I wanted to share their annual report highlighting all of the great work they’ve done this year and the big wins they’ve put up along with an appeal to join the organization/join the fight for a brighter New York.

And now Ryder Kessler one of the co-founders of Abundance New York is leaving the organization to run for office! I hope you’ll join me in supporting his campaign for NY State Assembly to make the whole state more abundance-filled.

I had wrist surgery on Tuesday and can’t type. Since then, I’m really enjoying wispr for voice to text.

It’s the deployment, dummies

All model development could stop today and we’d still have decades of implementation work to realize the promise of AI. The bottleneck isn’t scaling raw capabilities and the task of our time isn’t developing the machine god. It’s successfully deploying AI throughout the economy to accelerate GDP and raise living standards worldwide.

We’ve done this before, and it took forever

Computerization took roughly two decades. The shift to the cloud is still ongoing after 15-20 years. There’s no reason to think AI will be faster. Most of the economy isn’t using AI at all. A large portion has a top-down mandate to “do AI” but is failing to deploy anything meaningful or quickly. Only a tiny sliver of businesses and developers are credibly AI-native.

Why implementation is failing

Companies that want to move fast can’t. It takes vision and risk. And even when the will exists, organizational inertia, internal politics, patchwork infrastructure, etc. get in the way. It’s not just “change management is hard” (it obviously is).

Most companies don’t have data infrastructure anywhere close to what AI requires. Meanwhile, the complexity of enterprise environments is rising faster than the capabilities and visibility of those tasked with transforming them.

Where I’m looking

• Collaboration: Git was built for scarce, human-written code. Now enterprises are generating more AI code and shipping less of it. Whatever replaces Git will be built for that reality.

• Services: SIs/consultants are a critical chokepoint ill-suited to the task. There’s a huge opportunity to build new service providers on back of new capabilities and power AI transformation, better, faster, cheaper.

• Growth by buyouts: The product company acquires and transforms the operating business directly while owning all the upside.

• Apps: When you’re selling work you can fit within existing workflows like a person, just better, faster, cheaper.

Over the next decade there’s a foundation model-sized opportunity in deploying AI into critical systems throughout our economy and around the world. Developing the technology is not enough.

Cyber Dinner

​AI is breaking $1.5T of security market cap.

​For 30 years, cybersecurity has worked because attacks have had known limitations. Businesses have also had a concept of control: how to secure within a perimeter, how to vet vendors, and how to remediate gaps or accept known risks. The $1.5T security market cap was built on the assumption of visibility and control. That known landscape is gone with AI.

This winter I’m teaming up with ex/ante and Outtake to host a dinner and discussion in NY about the changing threat landscape and how new and existing security companies will meet that.

Apply to join here.

Virtue signaling

Elite consensus is starting to turn on the “anti woke” aesthetic and vice signaling. Sports betting is the canary in the coal mine for the great re-wokening that is coming. Get ready to see CEOs libbing out again within the decade.

New sincerity comes next. Everyone will talk about kindness, craft, moral virtue as the ways to redeem your soul and the character of the nation. Decency will go from being not just not cringe to actively in vogue. Eventually that will metastasize into facsimile and performance and we’ll reach the 2020-style ethics again.

Gen Z pining for peak millennial aesthetics and culture is more evidence of this larger trend. Prepare for libbed out “awesome sauce” imminently.

I Read

• The peasant logic of MAGA politics. On an abundance vs. scarcity mindset and the politics/ sociology of zero-sum thinking

• Tech bros head to etiquette camp as Silicon Valley levels up its style. More fun coverage of our etiquette school this time in the Washington Post. This is definitely a thing! I expect we’ll be taking etiquette school on the road next year. Hitting more cities, more founders, more venues.

• Shock jockey capitalism. Good long peace from Will Manidis on the increasing tendency to compete over “who can say the biggest number” in venture/startups.

• Syria after Assad: A year in numbers. Things in Syria are still really bleak but this is a bit of a white pill with some hope on the horizon starting to come through in the numbers.

• Power Law And The Long Tail - AVC. I was reminded of this (old) piece from Fred Wilson over the last week because of a reference from Euclid Ventures. Even if all of the money gets made on one end of the distribution (the biggest winners), all the time gets put in on the other (with the relative losers). It might seem non-economic to do that but in a business where your reputation and your network are everything, devoting that time does make sense and the emotional investment is so high.

This week was SF for our small holiday party + some meetings + the etiquette school book launch (more below).

I’m getting wrist surgery next week which will make typing hard. Expect shorter prose.

Pivots: changing the vector or the destination

Pivots can really suck for founders and we don’t want to pressure people to “make it work” when it’s not working/isn’t gonna work. In general, we don’t support people trying stuff just to try it when the original idea has clearly failed

But there’s a lot of space between that and the obvious fact that in very early companies you’re largely betting on people and general directions; the rest is subject to change and experimentation.

So what kinds of pivots should you do/do I (generally) support? I think there’s basically two kinds:

1. Type 1 pivot: change the angle of approach on a consistent vision or focal point. This is just wiggly early stage experimentation and iteration with consistent commitment to a vision of the future.

2. Type 2 pivot: change the end point and thus the way you get there. This constitutes changing the company entirely. It almost never works because you’re starting over at a disadvantage (less money and time).

Much of my investing/process with founders is about working backward from big themes and stories to companies that are worth owning in that future and finally how to start working toward them today. Within that framework, pivoting/changing the angle of approach is a question of “how” not “what” or “why.” So type 1 pivots are not only common but good.

And anecdotally, when founders ask me for an opinion, their pivots usually fail. But when founders tell me about a decision, their pivots usually work/go well.

Make of it what you will but I think it largely comes down to conviction and speed of execution. This is over enough examples and time to be a pattern.

Of Course We’re in an AI Bubble

A couple weeks ago Fred Wilson referenced Evan O’Donnell’s work tracking token usage to demonstrate that we’re not in an AI bubble. He concludes that “The current infrastructure spend rates are justified if the current rate of AI usage continues. If the growth rates start to decline, there could be trouble.”

But this is the wrong mental model/wrong question to ask.

In the 2000 crash, (revenue) multiples were blown out. And again in the 2021 private tech bubble. But here there is no doubt about the (token/revenue) growth being real. The multiples, at least in the public markets, are sane. Instead, this time around the revenue/usage itself is dubious.

No sane person is arguing that AI companies aren’t growing exceptionally quickly: from VC backed apps to Nvidia this is obviously true. The questions are in the retentive quality and earning power of that growth. Valuations, obviously, are forward looking.

In more strictly market terms, Felix Salmon claimed that we’re not in an AI bubble because 1) it’s not a get rich quick scheme 2) there are no greater fools 3) it’s not speculative. This is wrong on all three counts.

1. There are get rich quick schemes. There are ample ways to get rich very quickly from AI investing and many people are cashing in on. These include: selling stock in the hot companies (there are active secondary markets and they function like public companies), raising capital as an SPV provider and charging origination fees (the practice has been widely documented), and most significantly just raising huge sums of capital for funds (mgt fees to invest 500M at a time will make you very rich upon signing the docs).

2. There are greater fools. It’s not strictly speaking “retail” but there is absolutely a retail-like cohort of HNWI clamoring for exposure here. They are/will be the bag holders, as very likely will Joe Public both through the IPO market and government guarantees.

3. It is highly speculative. Just because the speculation is (mostly) happening in private/semi-private markets, doesn’t mean it’s not speculation. With #1 and #2, there are ample opportunities for purely speculative investing.

You don’t need to work my word for this - the inflaters of the bubble will say so themselves! The argument is not that AI is not a bubble but rather whether or not bubbles are good or “worth it.” It’s a Carlotta-Perez-style argument. TLDR bubbles are good/have utility because they lay the groundwork for R&D and buildout of ultimately useful infrastructure.

The question isn’t “are we in an AI bubble.” We are. The question is “so what?” What do you/we do or do differently?

Hamlet’s seed round

Most of the power that matters to businesses building in meatspace lives in four hour council meetings. And most companies only experience local politics as a blunt yes or no on a project. The actual logic sits in badly indexed hearings, PDFs, and livestreams that nobody watches. The arcane obscurity of local council meetings is one of the key mechanisms by which NIMBYism holds back dynamism and abundance.

Hamlet is trying to flip that. Take the raw exhaust of local democracy and turn it into something you can actually reason over when you decide where and how to build. Hamlet ingests agendas, minutes, and meeting video across cities and turns them into structured intelligence. Covid put local government online and LLMs made their proceedings parsable.

Customers developing data centers, energy projects, and housing use Hamlet to see when issues, parcels, or asset types they care about show up on an agenda. They can search across transcripts, pull exact quotes, and understand how individual councilmembers think about a given use. Hamlet helps critical industries build better, faster, and with more community engagement/support.

Over time, Hamlet is building a local decision graph and operating system for doing business in cities: agents and tools on top that handle site selection, risk scoring, and briefing prep. It also helps unblock a major artery of permitting, community engagement, and local development. If you care about an abundant future in the real world, you have to care about councils, boards, and the information systems that sit on top of them.

We are excited to share that we have led Hamlet’s seed round, with participation from Animo and Crosslink. Hamlet has raised nearly $10M to date.

Hamlet CEO Sunil Rajaraman is the most Abundo-pilled founder we have backed to date. Sunil is a repeat founder and seasoned operator, having founded or helped build Scripted, GoodRx, and Metromile. Most importantly, he has real vision and conviction for making local government a more effective, operable interface for operators and communities.

You can read more about the company in Techcrunch and you can watch Hamlet TV on Apple TV and Youtube. Hamlet TV is hilarious - it’s just the most out of pocket moments from local council meetings as a compilation.

Links

• How this 21-year-old college student used AI to build ‘Learning with Lyrics’. This is my favorite instagram account right now.

• You’re on Ozempic? How Quaint. We’re all gonna be on GLP-1s and they’re gonna be better and better (they might not even technically be GLP-1s pretty soon).

• Democrats have their own extremist problem.

Etiquette Guide

Slow’s Etiquette Guide for modern business has launched on Amazon! Tech and startups aren’t outsiders anymore. We’ve won.

Slow is doing important work to make sure people show up accordingly with poise and grace suitable to the task of running the world. The titans of industry used to build museums and cultural institutions. Etiquette school might be the start of reviving that noblesse oblige among founders.

Returning the subject of important narratives again and the criticality of good storytelling from last week.

I think if I’ve made one consistent mistake over the last couple years it’s been assuming that the components of an idea/business/valuation are 75% inherent/intrinsic qualities and 25% narrative.

In retrospect, I think I got that backwards (or worse). Narrative is everything. After all, startups are mostly just stories about the future.

Maximizing valuation is not unto itself a winning strategy but crowning yourself a winner clearly is. Remember, markets are reflexive so the winners win because they’re gonna be winners.

The missing piece that most companies get wrong is that to the extent they have a nominally compelling narrative at all, their narratives are entirely inward-facing (ARR growth, markups) instead of outward facing (vision of the future, stakes and consequences). That’s the difference between narrative weight and mere hype.

Whether you have $10k or $10M of revenue, on the scale of what you need to accomplish (hundreds of millions growing to billions), it all rounds to zero. What matters is putting up proof toward something important and greater than yourself: vision and a story for the how the world changes when (not if) you win, and just as importantly what happens if you don’t.

When you only have internal milestones, vision, and focus (look at how much we raised), you’re only as good as your latest announcement; you own nothing.

Narratives and storytellers that win can make the case for why they own the future.

H/t to Ashley Meyer and Beezer Clarkson for talking through this with me

More YC / Garry Drama

Garry Tan and I got into a bit because he insisted that YC isn’t about building what’s fundable but rather about pursuing passion, left of center ideas, and truth.

Methinks the lady doth protest too much

Here’s the truth about Y Combinator.

YC has helped start any number of great companies. YC is good!

YC’s value proposition is making only moderately credentialed young people (recent stanford grads, big tech engineers, etc.) look maximally legible to the capital markets. It’s a factory line that takes in engineers and manufactures buzzy seed rounds.

That is a useful function in the market and society. As a result of their work in templatizing and productizing company building, there are more companies. The SAFE alone has created tens or hundreds of billions of value in the world. Why lie?

All the values Garry is espousing are genuinely great: funding illegible ideas, doing your life’s work, bucking consensus, etc. We strive to do that work here at Slow but it’s not the only worthwhile approach. YC is doing something very different and doing it very successfully.

YC is the startup navy. They take young people and give them process, structure, rules, and scale to win. It’s not possible to operate at that level of scale (hundreds of companies at a time, nearly 1000 per year) and remain an independent boutique. It beggars belief that you can be BOTH the biggest AND the the most artisanal.

And funding “plenty” of non-consensus things doesn’t really mean anything when you operate at that scale; there is always random variance in numbers that large.

So if YC is the navy (process-optimized, standardized, sequenced, moving in unison) we’re looking for pirates.

• Founders who wage asymmetric war

• Founders who have a lot of fun

• Founders who accept cast offs with open arms

• Founders who don’t give a shit what you think

At the end of the day we’re all capitalists in the business of (hopefully) making money. That is nothing to be ashamed of and no one should hide from what they do well. We believe that it is on its own a worthy goal and that startups, by dint of existing and succeeding, are good for the world. We’re not bashful about that.

Ban sports betting apps

Sports betting is one the biggest challenges to my generally libertarian attitude. I had no idea how big the latent demand would be and how much damage it would do - couldn’t conceive of it. Total L for “don’t yuck their yum” school of social policy.

I would happily accept more casinos in exchange for banning FanDuel, draft kings, etc. And no, sports betting via “event contracts” on Kalshi, Polymarket, Robinhood are not better.

For all the ways that casinos in NYC would be an eyesore and body blow to the social fabric, the current omni presence of online casinos are worse.

If people want to bet, fine. But make them leave the house and see the sun each time they do. No more infinite access. Make it a concerted vice bounded by place and with appropriate indignities instead of a lifestyle.

Ban sports betting apps. Ban sports betting ads. It’s a tumor that has to be cut out.

New seed rounds

In 2018, a typical SF/NY Series A was 8 on 32 post with 500k-1M of revenue in ~1-2 years.

Today a typical SF/NY seed is 6 on 30 post with 500k-1M of revenue ~6 months.

Most seed investors are momentum Series A investors now. Adjust your frameworks accordingly.

Creator Fund: Tayla Cannon

For as long as we’ve been working together, Megan and I have been talking about creator-led healthcare practices and the opportunity for providers with big audiences to build big businesses. Now Megan is live with the latest creator fund investment in Tayla Cannon, a physical therapist building both a media brand and software platform for other PTs (and much more over time).

She deeply understands both sides of her community and her vision addresses their pain points. The PTs are burned out, trading time for money with no path to sustainable impact, looking to scale their practices virtually while delivering high-quality, consistent care. The patients are active who don’t want pain dictating their training or life and are seeking proactive, progressive care — not just five exercises to do at home.

Our investment will support Tayla as she grows her community and leadership in the space while accelerating the infrastructure she’s building to deliver on her vision of modern physical therapy.

You can read more about the investment in Techrunch and in you can read the full investment memo in Megan’s newsletter.

Oceans: next frontier

Angele, the associate at Slow who wrote the previous nuclear waste deck is back with her maritime security thesis.

TLDR -

1. The Oceans Are Infrastructure. Subsea cables, ports, offshore energy, and shipping routes quietly power the global economy, but remain largely invisible until something breaks.

2. Threats Are Rising and Becoming Harder to Detect. Maritime risk is increasingly asymmetric: from sabotage and illicit activity to autonomous swarms operating far from shore.

3. Autonomy Is the Next Great Accelerator. Advances in compute, sensing, and connectivity are lowering the cost of persistent presence and persistent threats.

4. Gaps Remain Hidden in Plain Sight. Defense investment has taken off, but navies won’t be enough. Securing the seas will also require bringing innovation and next-gen ISR capabilities to the “coast guard” and asset level.

Angele is very sharp and well connected around deep tech and critical industries. One to watch.

I’ve been thinking about the necessity and discipline of only working on/backing important stories. Embedded in that are two concepts:

1. You need really compelling stories (and storytelling) to win

2. Plenty of things can be good businesses but very few can be important companies

As markets and the information environment becomes more reflexive (the winners win because they’re winners), you need early proof that what you’re doing matters to attract capital, then team, then customers beyond the earliest believers that each accords. That requires narrative as an interface with which to interact and through which to understand a company and idea.

Narrative precedes you into every conversation, stands in for you when you can’t be in the room, and is what you leave behind.

The most vital component of that narrative is an answer to the question “why does this matter? Why is this important?”

After all, the most painful way to fail is to win a race with no prize. If you’re doing unimportant work, you can “win” and still lose.

And it’s not even clear that important work is harder or less likely to succeed. Maybe from a standing start important work requires more effort (moving a mountain vs a bowling ball). But when you’re working on something important you can muster more resources to build real momentum that accumulates and sustains you through adversity. Remember: P=MV aka momentum requires mass, not just velocity.

Building companies that matter/working on important stories and ideas attracts catalytic materials (namely talent and capital) necessary to succeed, at least once you can articulate the narrative such that it presages your victory as weighty and inevitable. The alternative is low odds which drive lower for want of resources to win a meager prize.

Even allowing that important things are 2x as hard (not sure I accept that), the rewards are much greater than 2x as big. There is no expected value in unimportant endeavors - not on a relative basis.

But what does important look like? Is there a falsifiable test? At this point I have a working framework and a few ideas (some of which are tautological with the above) for how to identify importance:

1. Narrative potential energy - big ideas that can be expressed clearly enough that they can take on a life of their own.

2. Start at the end - articulate a vision for why winning matters and what a maximally successful version of your idea looks like. Assume you’ve already won - how has the world changed/how have you changed it? Has power shifted or the earth moved?

3. Surface area - To be important is to have reach and the potential to compound. Companies don’t compound by doing more of the same but by doing/enabling something new, time and time again.

4. Losers and villains - Losers or villains are necessary tension to express importance. A company that rewires markets has to catalyze a power shift: either by taking power from or empowering someone else, ideally both. It’s why “historically low software penetration but now we can do AI” is such a snoozy, unimportant framing for a company.

5. My feelings don’t care about your facts - As soon as you start using TAM math (X percentage of Y market at Z rate) to explain why something matters, you’ve already lost the argument. The math should be self-evident and come at the end.

I’m willing to accept that my 5 part working rubric is wrong but the premise behind it is not.

Any undertaking that isn’t important and can’t articulate a narrative for itself will be constrained by a lower bound of inputs, momentum, and expected value. Backing or working on unimportant stories might “work” but it systematically removes you from compounding upside.

Play important games, win important prizes.

Vice Signalling

If the 2010s were the decade of virtue signaling culminating in 2020’s culture war bonanza, then the last 5 years have marked a dark turn toward “vice signaling.” Now being bad is good and so much of contemporary culture feels like a competition to more brashly signal cruelty, vice, and contempt. The return to calling people “gay” and “retards” is the clearest sign of this culture shift but it is one of many.

For all the ways virtue signaling is/was inauthentic and annoying, even pretending that you care about the world is clearly better than dismissively cackling that of course you don’t. Being bad feels fun and dangerous but actually doing bad is, of course, bad!

The spirit of vice signaling has infused our politics, business, art, and markets. It is the dominant note growing louder over the last few years as backlash to the prior decade of virtue signaling.

We’re reaching the apex of vice signaling and at the start of a vibe shift back toward virtue. People are being confronted with the fruits of nihilism, cynicism, and cruelty and the worm is starting to turn.

The signs are signing and I expect sincerity, virtue, morality will be cool again by 2027.

Get ready to lib out with me.

VCs hiring VCs

I’ve been running this hiring survey for venture funds looking to hire investors and a talent survey for the other side. If you’re interested in potentially getting matched with/intro’d to opportunities, please fill it out. It’s all double opt in and I have a pretty good slate of opportunities right now.

Note: I’m not going to share the whole list for the sake of trust and anonymity.

I Read

A SF VC in NYC

Like de Tocqueville capturing the unique spirit of America as an outsider in 1835, Nikhil nails the New York startup spirit from his seat in SF:

I do believe that San Francisco and Silicon Valley continue to have the highest concentration of the most ambitious founders, and likely always will. But NYC has plenty of founders with world class ambition, and most let their businesses speak for themselves, which feels different from a lot of what we see in SF.

Perhaps one of the keys is that NYC has many people, not just startup founders with world class ambition — arguably the highest concentration of any city anywhere. You may be a great founder, but you’re around great artists, bankers, chefs, lawyers, and more. When everyone around you is reaching for the top, it can’t help but raise the collective ceiling. Everyone honing their craft, finding their footwork in every field, in the city that never sleeps.

The Monks in the Casino

It’s very clear by now that legalizing online sports betting was a colossal mistake. It’s one of the shot calls I’ve gotten most wrong. I couldn’t have foreseen how it would be so quickly normalized and omnipresent.

If everything is becoming television, and everything on television is trying to become gambling, then the end point is not hard to see: On every screen, a casino.

This shift has moral as well as economic consequences. When a society pushes its citizens to take only financial risks, it hollows out the virtues that once made collective life possible: trust, curiosity, generosity, forgiveness.

Peter Thiel: Capitalism Isn’t Working for Young People

Thiel with some of the most cogent writing about NY’s Mayoral race. I don’t agree with all (many? most? any of?) his conclusions but I definitely think he’s right about diagnosing the mood in America.

But to Mamdani’s credit, he at least talked about these problems. So my cop-out answer is always to say: The first step is to talk about the problems, even if you don’t know what to do about them. There’s been a failure of, let’s say, the center left-center right establishment to even talk about them.

I don’t know if I would say that young people are pro-socialist. I would say they are less pro-capitalist than they used to be. If capitalism is seen as an unfair racket of one sort or another, you’ll be much less pro capitalism. So in some relative sense, they’re more socialist, even though I think it’s more just: Capitalism doesn’t work for me. Or, this thing called capitalism is just an excuse for people ripping you off. [...]

Maybe we should look for solutions outside the Overton Window. And that includes some very left-wing economics, socialist-type stuff. I don’t think those ideas will ultimately work, but they’re more than whatever was on offer. Cuomo did not have a plan for housing. He didn’t even think it was an issue. And of course, he’s been in politics and government for many, many years, so it’s hard not to ask: Why is he going to do something now, if he hasn’t done anything before? So, I’m not optimistic about Mamdani, but if you score it relatively, this is the kind of thing that’s going to happen if you look outside the Overton Window for solutions.

The Sierra Club Embraced Social Justice. Then It Tore Itself Apart.

The problems at the Sierra club are a pretty good encapsulation of so much of what has plagued organizations on the left. Very much parallel to the mistakes the ACLU made over the last few years. Focused organizations are effective organizations and you need big tents on single issues vs the omnicause. Let the main thing be the main thing.

It drove away longtime volunteers who loved the club’s single-minded defense of the environment, by asking them to fully embrace its pivot to the left. Some even felt they were investigated by the club for failing to go along. Many hard-core supporters felt the Sierra Club was casting aside the key to its success: It was an eclectic group of activists who had one, and sometimes only one, cause in common.