A Play Money Whitepaper
The operating system for the first $2M in funding.
Read the Paper ↓Someone with a big obsession and more courage than sense sees a missing piece of the future and drops everything to build it.
They ship an MVP.
They find early revenue.
Then they need money and we tell them:
Oh, and if it’s not obvious how your business gets to $1B in revenue, don’t even bother.
Pardon my French, but WTAF?
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Where’s Waldo illustration from the whitepaper.
One of the best things to happen to innovation is the explosion of new people allocating capital. Diversity in check writers — by lived experience, geography, and check size — should make innovation flourish.
It hasn’t. Our lack of imagination and basic use of technology turned the explosion in check writers from rocket fuel into a fragmentation tax on founders — and, by default, on financial and societal returns. This tax is not inevitable; it exists because the early capital stack shifted and the infrastructure did not.
Today’s allocators are still running on playbooks built for a world where Sand Hill Road was the only game in town.
But fragmentation isn’t just an infrastructure problem — it’s a behavioral one.
These aren’t separate problems. They’re two sides of a coordination layer that doesn’t exist yet.
Sidebar: Already running a fund? It’s a new channel. Starting fresh? It’s the whole model.
Together, they turn thousands of long-tail checks into one coordinated capital stack, creating a behavioral dataset and coordination layer that gets stronger with every deal flowing through it.
When the long tail runs on one OS, it becomes the market maker — reshaping how new companies get funded and who gets to participate in returns.
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Fragmentation diagram — showing how capital flows scatter across hundreds of disconnected channels vs. coordinated through one OS. The “before/after” of the long tail.
Every successful pre-seed fund eventually scales AUM and moves upstream. As Charles Hudson put it, fund size is strategy. The strategy keeps moving upstream. It’s not a one-time shift — it’s a cycle.3 The funds that happily led $500K seed rounds five years ago now prefer larger, later checks. And the next wave of emerging managers will do the same thing.
As fund sizes grow, managers converge on a few consensus bets that can plausibly hit $10B outcomes. Durable businesses returning 10–50x on sane entry prices go unfunded, not because they’re bad bets, but because they don’t fit the institutional math.
It isn’t just us. Will Manidis recently argued4 that venture capital is trapped in a “doom loop” of oversized funds, broken exit markets, and LP structures that prevent doing the obvious thing. The fix won’t come from the top of the stack. It’ll come from building infrastructure for the capital that already has the advantages institutional VC is trying to manufacture.
Domain experts, emerging fund managers, exited founders, and future customers are willing to back the non-obvious and the non-consensus. This is where alpha lives.5
The founders who used to need $5M to ship now need $500K. They’re building durable, capital-efficient companies that don’t need the traditional VC escalator to get big. For angels, that’s better economics and arguably less risk when companies don’t need to “decacorn out” to make the math work.
The infrastructure hasn’t caught up. Everything about early-stage funding has shifted — who writes checks, how much founders need, what good companies look like. The most valuable capital on the cap table still runs on spreadsheets, group chats, and one-off SPVs stitched together by personal networks.
Public markets already closed this gap. Robinhood‑style apps dropped account minimums, wrapped everything in a mobile‑first experience, and made it normal to buy slivers of stocks instead of whole shares, rewriting the basic terms of how people get started. Early-stage private markets haven’t had that step change yet.
Three-quarters of accredited investors want exposure to early-stage startups. If just 20% of them put $10K a year in, they would dwarf today’s institutional Pre-Seed-to-Series-A firepower.
Jenny Fielding built Everywhere Ventures on exactly this premise — $70M across ten micro-funds, powered by 500+ founders and operators as LPs, not institutions. The dollars and desire are there. The infrastructure to serve them isn’t.
But the capital showing up today isn’t just bigger. It has a new mandate.
The next wave of angels expects their money to multitask: they want financial returns, meaning, and more agency and alignment than institutional capital provides.
Institutional VC is tuned for TVPI and markups on a decade-long fund timeline. Individual investors want their money in motion — realized IRR cycling back into more deals, more founders, more creation.
The real bottleneck is scaling the scarcest resources in the system.
Every actor in the system is spending their scarcest resource on the wrong work.
Founders should spend their best hours catering to the needs of customers, not VCs. They should be able to effortlessly access the connections, expertise and amplification of their Angels.
Local ecosystem builders should anchor in education and community, not cat‑herding small checks and gatekeeping myriad investor intros.
Specialist GPs — the fund manager who spent fifteen years in supply chain, or the former founder and FDA reviewer now writing checks in medtech, should spend their time identifying, diligencing, and accelerating companies in their lane, not running the generic fund machinery that has nothing to do with their actual edge.
A lot of emerging fund managers think they would like to start a fund because they enjoy investing in startups. But as a fund manager, investing is probably only 20% of the job. The bulk of it is fundraising, portfolio support, fund ops, and marketing.
Remember the early days of AngelList? Naval, hand-picking his favorite deals every week and sending them straight to angels. (My startup was one of them.) The whole ecosystem was paying attention at once — and the angel was at the center of it.
Then the market grew, and that experience fragmented. Each tool grabbed a piece. Most of them stopped building for the angel altogether.
Made it easy to close deals — but they’re optimized for middlemen and one-off transactions, not angels building portfolios. Transactions without insight.
Surface more deals faster, but they don’t help the best allocators build a following or help investors learn from the people worth following. Discovery without compounding human expertise.
It’s great how Ryan Hoover’s Product Hunt for Startups rally social proof around founders. But the capital still lands as one-off bets. They’re planting a bunch of trees that aren’t adding up to a forest. Social proof without industry leverage.
Even the best programs, like Hustle Fund Commons, sit alongside investing, not inside it. Every week we see investors who’ve taken every course freeze before their first check. Education separated from the decision itself doesn’t build conviction. Learning without action.
Groups like Decile and Recast make it easier to spin up a fund, but they still assume the answer is “become a fund manager.” Specialist GPs are the scarce resource; their taste should be the product. Replication without reinvention.
Lots of trees. No forest.
We started by doing one thing very well.
Each investor sees one deal a week. Always on Thursday. Specialist-vetted, highly curated. Angels invest alongside the most inspiring early-stage fund managers and a growing crop of specialist GPs. Short-form video brings founders to life, and everything you need to say yes is in one place. We wrap it all in snack-sized education, in plain English. And it’s always free to lurk and learn.
It feels like an engaging consumer experience, not an old-school diligence room chore. That simple formula turns a spark of interest into repeat check-writing.
The Thursday drop isn’t a gimmick – it’s a habit loop that does two things. It teaches us how each investor makes decisions. And it gives specialist GPs a way to showcase their expertise and build a following.
What emerged were two core systems: a Conviction Engine and a Fluid Fund. Together, they form the operating system.
The OS is live, by the way. Get on in here →
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Figure-8 flywheel diagram — Conviction Engine on one loop, Fluid Fund on the other, showing how they feed each other. The behavioral dataset at the intersection.
The most persuasive signal for a new angel isn’t facts, data, or what other investors are doing. It’s seeing their own patterns reflected back to them.
65% of angels are structured thinkers9 but they lack a clear rubric. The Conviction Engine watches how each actually engages: what they click, watch, skip, ask, follow, and fund. It learns not just which deals to show them, but how they get to yes.
From The Founder
I thought I was biased towards a founder energy that mimicked my own. I was wrong. Turns out what grabs my gut is a founder talking about their customer with above-average specificity. A customer-fluency thesis I never named.
I used to think my interests were eclectic. They’re not. 60% of my bets cluster around waste-to-value business models across verticals.
I stared at a climate deal five times. I couldn’t walk away but couldn’t pull the trigger either. I didn’t know what was blocking me. The system did. It noticed a pattern in my questions across other deals. Apparently I ask about playbooks and industry economics. So it surfaced the specialist GP’s evaluation framework alongside parts of the founder interview and assembled a mental model for me that I didn’t even know I was looking for.
Yes, I wrote the check.
The Engine learns which expert lens unlocked which investor’s conviction, and makes that match faster next time. Over time, it stops being an expert’s rubric and becomes theirs, reflecting back a thesis they didn’t know they had, connected to the specialist voice that makes it click.
The result? 58% of investors make multiple investments.10
To monetize that today, they need to raise a fund or cat-herd SPVs. The Fluid Fund turns their judgment into a capital base without the fundraising overhead. Their reputation, and the capital that follows it, grows with every deal.
What’s better is the GP isn’t just funneling capital to their portfolio of founders. They are assembling a support network of engaged investors behind them.
The OS maps which angels have the connections, expertise, or amplification each company needs when they ask. Founders funded by a Fluid Fund get more GP attention and more angel leverage, without the GP having to play middleman.
The Conviction Engine pools capital and expertise. The Fluid Fund lets the right GPs claim it.
Already running a fund or syndicate? The Fluid Fund isn’t a replacement. It’s a new channel. No fund? It works as your whole model too.
Investors are already lining up for the Fluid Fund without knowing it.
The Fluid Fund sits in exactly that whitespace.
In Action
The best climate founders seek out Andrew for his expertise. He has a deep thesis in the space, a strong network, a clear rubric for picking companies, and a track record of improving their trajectory when he gets involved. The companies he finds need bigger checks than he can write on his own.
Four months on Play Money, he’s moved $500K into his top climate bets with fund-caliber economics — carry and management fees that match or exceed what a traditional fund structure would deliver. His capital base grows with every deal — not just from investors he brings, but from the platform’s own growth matching new investors to his track record. He could turn this into a fund if he wanted to. But why would he?
He spends his time finding companies and helping them win. The platform handles everything else.
Every deal on the OS represents a coordinated capital stack, not scattered one-off checks. With scale the platform stops just serving the market and starts shaping it.
That clout shows up in two ways.
The first is the power to reshape terms. This capital doesn’t just invest differently, it can set different terms. Catherine Bracy named the deeper problem in World Eaters:
“The venture capital approach to investing has crowded out other forms of capital that could support sustainable startup development. What results is an unhealthy monoculture where only one kind of company can be successful.”
— Catherine Bracy, World Eaters
A single angel can’t reshape terms. But thousands of coordinated long-tail checks can evolve deal structures that let companies grow on their own terms instead of getting force-fed or starved by the VC playbook and keep investor money in motion when the rocketship doesn’t pan out.
YC proved that a single structure, the SAFE, could become an industry default when enough capital adopted it. We’re dogfooding this ourselves with the SeriesSAFE, an iteration on the YC SAFE that grants investors QSBS qualified equity from Day 1. Early days, but the experiment is live.
The second is exit coordination. Individual angels and most emerging fund managers don’t have the scale or expertise to figure out – or execute on – the best time to exit. In a bifurcating capital market where IPOs aren’t the only (or best) way out, that’s a real disadvantage.
But long-tail checks coordinated on one OS? That’s the foundation for institutional-grade portfolio management, the kind only big funds have had access to. This is how everyone else gets there.
It also happens to look a lot like an early-stage index fund, one of the best performing structures in venture. Just ask the team behind AngelList Access Fund.
This is what industrializing the artisan tier looks like (h/t Charles Hudson)12: Turning thousands of small checks into a professionally managed asset class with the clout to match WITHOUT sacrificing the diversity of conviction, specialist judgment, and founder alignment that make long-tail capital the best capital on the cap table.
Every investor, every GP, and every community that plugs in makes the OS smarter and the network more valuable. That’s the flywheel:
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How Money Compounds flywheel diagram from the whitepaper.
Early participants shape the dataset, get the best matching, and build track records while the platform is still small enough to give them outsized visibility. The OS gets more valuable with every node. So does your position on it.
If you’re an emerging fund manager, exited founder, or domain expert tired of running fund machinery instead of finding winners, the OS is live.
Just ask Andrew Eil.
If you’re a community leader who wants to activate the capital ecosystem for your city, university, or passion area, we built the infrastructure so you can flex real power for the founders that matter most to you.
Just ask Josh Carter in Oregon.
If you’re an angel group ready to get 30% more of your members investing and double the capital raised from your diligence with zero-effort syndication, this is how that happens.
Just ask Girl Math Capital.
When the long tail runs on one OS, it becomes the market maker, reshaping how new companies get funded and who gets to participate in returns.
Notes