"Rebelling against authority is an American trait."
This country was founded by outlaws.
Our culture was formed by them. Our economy was built by them. The future will be created by them too.
Outlaws of history are not meant to be for everybody. They are spiky, top-percentile on a trait or obsession that separates them from their peer class. The maverick mentality required to make somebody truly exceptional in any field often alienates them from the crowd.
If you study some of the most iconic entrepreneurs of the last generation, almost all of them went through periods of being completely misunderstood before becoming totally understood.
Henry Ford was called a socialist for doubling worker wages and instituting the 8-hour work day. The wage hike eliminated turnover, attracted the best workers, and seeded the American middle class - which then bought every Model T he could build.
Walt Disney mortgaged his house to finish Snow White (a film projected to lose money). It became the highest-grossing film in history at the time, and Disney used the proceeds to build a studio campus and start work on Pinocchio, Fantasia, and Bambi simultaneously.
Elon split his last $40m in 2008 to save Tesla (running out of cash + weeks from bankruptcy) and SpaceX (three consecutive rocket failures and one launch attempt left before going under). Both companies today are worth a combined $1.5 trillion.
Travis Kalanick launched Uber in cities where the service was explicitly illegal. The Uber playbook - launch first, apologize later, weaponize user demand against regulators - became the template for an entire generation.
We think the best entrepreneurs share two traits: high rebellion (distaste for authority) + high commerciality (creating more value than capturing) = high return on luck.
The quadrant most of venture capital has been competing inside for the last decade has been the upper left. The pattern-matched founder. The Stanford CS dropout, the second-time exit, the well-networked technical hire from a hyperscaler. These are real assets. The industry has bid their valuations up accordingly.
The lower right quadrant produces some of the most fascinating people in history but very little economic value. Pirates. Mafia heads. Criminals. The romantic ideal of rebellion without the discipline that turns it into something (legal) the world can use.
The interesting quadrant is the one in the upper right. The people who scored well on both axes - who had orthogonal paths, refused to do things the way they were supposed to be done, and who built businesses that changed industries.
"It's better to be a pirate than join the navy."
Jobs was an outlaw. So was Rockefeller. So was Disney. So was Ford. So is Bezos. So is Jensen. So is TK. So is Musk.
If people weren’t naturally drawn to these types of individuals, we wouldn’t make them mononyms.
The next era of iconic founders will look no different.
Outlaw is a $10m investment firm that will become the chief capitalist to the upper-right quadrant. We invest as early as possible, and we make it our job to turn these people and their companies into the iconic names of the decades to come.
Below is how we got here, more on what we believe, and why we think now is the right moment to do this.
TL;DR
The fund in four bullets
For readers who skim, here's the 30-second version:
Out-of-distribution people → out-of-distribution companies. We invest in individuals before we invest in companies, and the bulk of our underwriting goes towards the founder(s).
API to the network. Six years of writing has created an army of 20k investors, founders, and operators who align with our worldview, trust us, and can act as an extension of our team when it comes time to work.
The pursuit of 1.5% of a $5b business. Outlaw I is a $10m pre-seed fund. 40 investments, $100k-$200k initial checks, 20% reserved for follow-ons.
We are raising under 506(c), which means we can talk about this in public. Most of the time, a new fund gets announced after it’s closed. We’re still fundraising while actively deploying, and there are still ways to get involved.
Only accredited investors are eligible, and all prospective LPs should know that investing in venture capital funds is inherently risky and illiquid. We are not registered as an investment adviser and this email is not investment advice. This fund is adhering to a traditional fee structure (2% management fee, 20% carry), and we are holding our next close on May 31.
How we got here
I consider myself a student of the internet, and Outlaw is a byproduct of remixed ideas from a collection of teachers.
Permissionless leverage
Traditional wealth was built on top of two forms: capital and labor. These are permissioned forms of labor and require buy-in from lenders or partners (capital) and employees or contractors (labor).
Naval introduced me to the idea of building wealth through new forms of leverage: products with no marginal cost of replication. Code. Media. Anything that compounds without consent. Jack Butcher's visual treatment of the same idea reinforced it further.
If you look at most of the wealth generated since the start of the century, it has come via these new forms of leverage.
That led me to go down the rabbit hole of research to understand the deeper history of these new permissionless forms of leverage - specifically media.
1996: Bill Gates published a short essay called Content Is King, arguing that over a long enough time horizon, the real money on the internet would be made by people who controlled distribution, not people who controlled production. This post was controversial at the time because most attention was still being monetized through ads.
2008: Kevin Kelly's 1,000 True Fans named the unit economics. You don't need a million fans, you need a thousand who care. (Side note: the economics can be much smaller (selling $1m product to 1 person) if your audience construction and offer positioning is done right.)
2019: Li Jin's Passion Economy showed the infrastructure had arrived. Making money on the internet is now a career path.
2020: Nathan Barry's Billion Dollar Creator made the case that most creators are criminally under-monetized. The biggest ones don't sell attention back to brands; they use it to build something that compounds. Multiple billion dollar companies have been built off the back of attention.
It seemed like the pattern was clear: we are all underestimating the opportunity to monetize writing published on the internet.
This led me to my next major rabbit hole: finding specific pieces of writing responsible for billions of dollars in economic value.
Billion dollar PDFs
To quote Jeremy Giffon, “A charming feature of the late stage information economy is that every few years someone writes a Billion dollar PDF.” In other words, every few years, somebody writes specific artifacts that rewire how the world thinks → rewires what gets built → rewires where capital flows.
Some pieces that drive this point:
Type of leverage | Example | What it did |
Created an asset class | $2T market from 9 pages | |
Built a movement | Reorganized AI policy discourse in months | |
Defined a category | Gave VC its decade-defining thesis | |
Started a religion | Built Berkshire's brand and attracted permanent capital | |
Named a market structure | Reshaped how operators thought about platforms |
The Nike Manifesto (1977), What Happened to the Future? (2011), Facebook's Little Red Book (2012), Airbnb’s Culture Doc (2013), We Don’t Sell Saddles Here (2014), Tesla’s Master Plans (2006 and 2016), Mission Focused Companies (2020), The Great Online Game (2021), and Endgame (2021) do more of the same.
Each of these was, and continues to be, a billion dollar PDF.
The most valuable writers in the world are architects more than they are predictors. They name the future they want to live inside, and then they take the first position inside it.
The first lesson was that writing is a strategic instrument more than it is a marketing function. The second lesson was that in order to capture the most from authoring a billion dollar PDF, you have to position yourself accordingly.
That brought me to the venture-specific version of the same question: who, inside this asset class, was already operating the model?
Narrative capital
I will never forget the feeling of first discovering some of the original VC bloggers.
When I discovered the writing of people like Bill Gurley (Benchmark), Fred Wilson (USV), Mark Suster (Upfront), and Tomasz Tunguz (Theory), it felt like I had unlocked the hidden secrets of the startup universe. I became an information sponge.
After a while, I began to realize why each of them was investing so much into building a writing portfolio. Their investing is a byproduct of their writing, and writing flywheel compounds the investing flywheel.
Writing gives poor thinking nowhere to hide, and many of the best investors in the world have given people a first-person view into how their mind works. Writing can be used to build a thesis, explain investment decisions, make predictions about where the world is going, and establish credibility in an industry where the natural disposition is skepticism. Like investing, a writing portfolio compounds with better ideas, higher-quality audiences, and a larger surface area for luck.
I owe these OG VC bloggers a ton of credit. Without them, I probably would never have started writing myself.
I figured if they're doing it, I should start doing it too.
Building Confluence
All of the above should set the stage for the belief that the investment firm of the future will be built on the back of a writing portfolio.
I began writing in 2020. At the time, my ideas were not good, I was writing into the void, and it was not clear whether I was building something or wasting time. This piece would not exist if I let any of that stop me from publishing.
Over the past six years, I made the decision to build Confluence in public. The writing flywheel has given thousands a front row seat into how my mind works when it comes to different aspects of investing.
Personal stories like the viral listicle of takeaways on my time in venture and a collection of lessons learned since becoming a GP
Frameworks adopted from studying some of the most iconic venture investors of all time
Proprietary data on things like industry comp and emerging managers that would be very difficult to be recreated
Red flags and consensus things I disagree with
Collections of lessons from $5b founders
A history of the asset class to reasonably predict the next 50 years of venture
A deep dive on my thesis
Redacted LP letters
650+ newsletters later, the writing has attracted a loyal audience of GPs, LPs, venture-backed founders, and operators into our orbit. Today, the newsletter reaches roughly 20,000 weekly readers and generates several million impressions each year.
This audience is a collection of people who have watched my evolution of thought over time and have chosen to continue tuning in week after week. The best people self-select on worldview, and these stories, along with hundreds of others, gave me a name, a following, and a foot in the door of rooms I otherwise had no business being in.
In May 2025, I wrote a piece called Narrative Capital. The argument was that media brands are good at the things investment firms are bad at (distribution, idea creation, brand, talent access) and investment firms are good at the one thing media brands cannot do (maximize equity value). Marrying the two is how a lot of wealth will be built this decade.
A month later, I wrote Audiences and AUM where I gave examples of funds built on top of a writing portfolio and made the case that writing flywheels and investing flywheels are interrelated. That was the realization that reframed what I had spent the previous six years building.
Confluence was not a newsletter. It was the early infrastructure of the firm I had not yet started.
The thesis
Fund I is one core belief, expressed through four investment theses.
The core belief is that out-of-distribution companies are created by out-of-distribution people.
Contrary to popular belief, we believe the true secrets of scale are rare, they are guarded by those who have experienced them firsthand, and they cannot be prompted. Power laws at the individual level are not (yet) consensus, but that is where we believe the majority of true venture alpha lives.
The founders in the Fund I portfolio will be a reflection of this belief.
We are naturally drawn to spiky founders, and we believe the best entrepreneurs are able to combine distaste with authority + high commerciality.
Fund I will back founders building in the categories below.
Artificial labor markets. We see these as the new labor markets, and the TAM is all white-collar work. We think revenue-per-employee is becoming the new North Star metric for most companies, and team construction, fundraising cadence, GTM motion, and comp structure are all downstream of that shift.
The token revolution. Every business is becoming a token factory - supplying, building, or orchestrating the data, identity, money, and expertise that feed agents. Tokens are how the world becomes legible to machines. Once you see tokens as the DNA and feedstock of AI, you stop asking what features does this product have and start asking what streams of tokens does this product control. The companies that win the next decade will be the ones that own the most valuable token streams.
Software 3.0. Natural language is the new programming interface, and agents are the new developers. The entire dev tools stack (IDEs, deployment, observability, testing, debugging) is being rebuilt from first principles, and Agent Experience now matters as much as Developer Experience.
The modernization of the private investment firm. The private markets in 2026 are at the same inflection point traditional finance was at in 1984. The asset class has scaled from cottage to massive over thirty years, and the pressure to perform has translated into a pressure to spend on workflow software. The best funds today operate more like software firms than like financial services businesses, and there is a high correlation between firms that have rebuilt modern workflows and firms that have distributed capital and raised fresh funds.
The flywheel
Newsletter flywheel: ideas → content → audience → trust → opportunities
Fund flywheel: finding (heavily boosted by audience and opportunities created in fund flywheel), picking (improved with ideas strengthened judgement via writing), winning (improved as newsletter asset differentiates from other investors who provide capital only), and helping (talent pipeline, distribution-as-a-service, downstream capital available to portfolio)
$5b businesses are not built without combining forces of leverage (code, media, labor, capital). We think of the firm as a product, and we have architected the firm to build leverage for each company we work with.
Our audience does four things for the fund.
Finding. Confluence is a content magnet for people who see great companies first. The audience is primarily GPs and investors, but it includes founders and quality operators. The newsletter generates several hundred high-quality opportunities per year through the network - investor referrals, founder referrals, content inbound, and curated talent nodes at companies like Ramp, Cursor, and Decagon.
Picking. Six years and four million words of writing have sharpened a specific kind of pattern recognition. We have met with thousands of founders over the better part of the past decade, and the quality bar continues to reorient up. We do not compete on trying to see more deals than other funds. We compete on being able to move quickly when one of them shows up.
Winning. The best founders (especially at inception) pick their investors based on a) their proof of work and b) their ability to help. Published pieces on worldview help drive alignment before any call. The ability to use the newsletter to creatively help founders post-investment positions well against more commoditized capital that wants a place on the cap table.
Helping. When a founder takes a check from Outlaw, three things activate immediately:
Distribution. Company deep-dives, founder interviews, "confidential" memos, and other content forms reach 20,000 high-signal readers. Many of them manage portfolios. Most of them are people the founder would otherwise spend months trying to get a meeting with.
Talent. A layered recruiting service hits the operator network - thousands of senior people who read the newsletter and trust the source.
Capital. Six years of relationship-building with GPs and partners at 200+ venture firms. When a portfolio company is ready for a Series A, we act as an API to the network and introduce them to the three or four investors most likely to lead the round.
The content flywheel also creates a natural recruiting pipeline for the future investment team beyond fund I.
As our flywheel matures, we want to become the obvious steward for the types of founders we target throughout different fund cycles.
The fund
Fund Size | $10m |
Management Fee (Annual) | 2% |
Carried Interest | 20% |
# of Companies | 40 |
Reserves | 20% |
The fund objective is to own 1.5% of a $5b business.
The strategy is built around a two-tier structure.
Discovery layer: We will write 40 pre-seed checks into companies that we believe have a realistic trajectory into becoming category-defining businesses by 2036 (ideally sooner).
Concentration layer: We will reserve five checks (20% of the fund) to invest into the highest-conviction names, with the benefit of 12 to 18 months of inside information from being on the cap table before any of the downstream financing signals are public.
If you are a verified accredited investor and would like to review the memo, the deck, the LPA, or the fund's full closing documents, fill out our LP interest form and we can set up a call.
Why now
On one side, the world we grew up in no longer exists.
Purchasing power will continue to go down. Housing will continue to become more expensive. Most labor will continue to be displaced either by AI, offshoring, or as a short-term cover by management teams touting “AI efficiencies”. The old American Dream of working a decent job, finding loyalty through an employer, paying off a reasonable mortgage, and letting that housing asset compound as your primary source of wealth is no more.The veil has been lifted, and people are being pushed farther out on the risk curve to afford the lives we once had.
The new American Dream is going digital. The land of opportunity is the internet. The Golden Era for builders is already here. Capital, infrastructure, and distribution barriers are no longer bottlenecks. The entire creative stack is accessible to anyone. There is now status that comes with being a founder. More people are entering the arena, and more will follow.
On the other side, the feast-or-famine nature of venture capital fundraising is rapidly killing off mid-market firms. The “messy middle” can't compete with the tier one shops on one end, and they are too awkwardly large to compete with solo capitalists and emerging manager crowd on the other. The industry structure has already split with a few very few large generalists and a lot of smaller specialists. Many of these smaller funds have tapped out of existing capital pools, re-up rates have dropped, and the window to build a brand that survives the funds 3–5 mid-market valley of death is closing quarter by quarter.
Legacy platform venture firms are raising record amounts, registering as RIAs, and launching alternative product lines. From my conversations with the founders and architects of these firms, everyone is circling the same idea space.
The industry is cementing, and it feels like the time to build is now or never.
Lessons from the greats
Outlaw is built on the shoulders of giants, and we have spent a decade of research borrowing concepts from notable GPs who came before us.
Don Valentine taught us about ego death, maintaining common sense in a field of geniuses, and how to build a firm that outlasts you.
Michael Moritz taught us the value of orthogonal frameworks.
Doug Leone taught us how to build a culture of winning.
Josh Kushner taught us about the value of conviction, how to maintain firm DNA through scale, and the alpha of hiring non-obvious investor talent.
Bill Gurley taught us about asymmetric regret and solving the principal-agent problem.
Bob Kagle taught us about venture firm flywheels and recruiting as the ultimate multiplier.
Fred Wilson taught us about the power of writing, how to develop a thesis, and how to say "no" to more capital.
Marc Andreessen taught us about ambition.
Peter Thiel taught us what to ignore.
Jeff Horing taught us the value of investor talent programs.
John Doerr taught us about execution and hubris.
Neil Mehta taught us about craftsmanship.
Micky Malka taught us about adaptability.
Graham Duncan taught us that talent is the best asset class.
Orlando Bravo taught us about finding great partners.
Steve Schwarzman taught us about pursuing financial opportunity.
The guiding question we kept returning to after studying all of these GPs and the firms they built: what would the investment firm of the future look like if it were created from scratch in 2026?
The initial chapters of Outlaw will incorporate a small, thesis-driven strategy pioneered by specialist firms like USV, Mucker, Benchmark, and others. Firm architecture has been designed after capital agglomerators such as Thrive, Sequoia, a16z, and Founders Fund in order to build a partnership that outlasts any one person - myself included.
The LPs
Most fund announcements have a tendency to name drop their LP base. That is not our style, and it isn’t the style of our LPs either.
We are backed by a collection of families and individuals who were able to find independent conviction, believe in the strategy, and have chosen to partner with us for the years to come. A few of them you would recognize. Most of them you wouldn't.
No single LP represents more than 15% of committed capital. Our base is composed of family offices that have spent the last decade backing emerging managers, operators from category-defining technology companies, GPs and partners at multi-stage venture firms, and a handful of founders who built and exited their own companies before deciding to back ours.
How to get involved
We are still closing the fund and we are still building the firm. There are three ways to be part of the next chapter.
Invest. Fill out our LP interest form, and we will follow up. We are optimizing the LP base for fit over speed - we would rather have the right partners for the next decade than the fastest closes for this fund.
Pitch. Tell us what you're working on, what stage you're at, and how you found us. We can move quickly when we have conviction.
Refer. Intros are the highest-signal source we have, and the best founder referrals consistently come from other founders. If someone you would personally vouch for is working on something in stealth, send them our way. We owe you a meeting in return.
One last ask
Fund announcements fall flat when the GP is the only one rallying the troops. We’re trying to make this announcement as big as possible, and we could use your help.
If any part of our story resonates, one of the most impactful things you can do is tell your friends about it.
Everybody shares things differently; here are things we have found that work the best:
Post / quote on X: Quote tweet our announcement (linked) with your perspective. (We have found that quick personal stories of how you found us, what you have learned from us, why you pay attention to us all work well. If you’re in a rush, even something quick goes a long way.)
Engage: Like and comment the post to boost visibility.
Share: Forward / tag the news to any founders, investors, operators, or allocators who you think would resonate with the message we are trying to send.
If you’ve made it all the way to the bottom of this email, thank you. None of this would have been possible without people like you.
