Research report 2026-06-16 – 2026-07-02

How the Smart Money Invests Now

6 min read 5 episodes 1 podcast 6% cited

Updated 2 weeks, 5 days ago

Photo by Anna Tarazevich on Pexels

Overview

Sophisticated investors are concentrating heavily in equities and AI-adjacent bets: Lloyd Blankfein, the ex-Goldman CEO, keeps 98% of his personal portfolio in risky assets with ~75% in single stocks across tech, energy, and financials. Leopold Aschenbrenner, a 25-year-old ex-OpenAI researcher, has grown a hedge fund to ~$5B by betting on AI at a scale most institutional players overlook. Meanwhile, retail platforms like Autopilot ($1.8B AUM) are democratizing institutional strategies — copying politician and hedge-fund trades in real time — while private equity giants like Carlyle Group ($500B AUM) underscore how dominant alternative assets have become.

Most represented

Top voices

  • My First Million 11
  • Warren Buffett 15
  • Nancy Pelosi 12
  • Nick Sleep 10
  • Lloyd Blankfein 10
  • David Rubenstein 10

The arguments

Concentrate in Equities, Ignore Diversification

Lloyd Blankfein's personal portfolio runs 98% in risky assets, mostly single stocks in tech, energy, and financials — a direct rebuke of conventional diversification advice from someone who ran the world's most sophisticated investment bank.

AI Is the Defining Investment Thesis of This Era

Leopold Aschenbrenner, author of the 'Situational Awareness' AI white paper, built a ~$5B hedge fund around AI conviction at age 22, arguing that most institutions still underestimate the speed and magnitude of the transformation.

Retail Can Now Access Institutional Alpha

Autopilot's copy-trading platform lets retail investors mirror politicians and hedge funds using public disclosure data, managing $1.8B without taking custody of funds — pointing to a structural democratization of 'smart money' strategies.

Invest in What You Already Use

Shaan Puri and Aaron Levie argue for a practical heuristic: buy equity in the tools embedded in your own business's P&L that you couldn't switch off, a strategy they claim would have outperformed over a 20-year horizon.

Hard Assets and Alternative Markets Offer Outsized Returns

From campground roll-ups ($20M revenue on $60M raised, portfolio worth $100M+) to a mine turned into a $10B public company (MP Materials), smart money is finding alpha in overlooked physical and alternative asset classes.

Mixed verdict

Private Equity Scale Is Unmatched — But Access Is the Moat

Carlyle Group's ~$500B AUM illustrates how private markets have become a dominant force in sophisticated capital allocation, yet the strategies powering those returns remain largely inaccessible to retail investors without platforms like Autopilot.

The Blankfein Portfolio: Maximum Risk, Minimum Diversification

Lloyd Blankfein — who ran Goldman Sachs through the 2008 financial crisis — keeps 98% of his personal wealth in risky assets, with approximately 75% in single stocks. His concentrated bets span three sectors: technology, energy (rooted in his trading background), and financial services (his professional domain). He trades daily from an iPad, treating market monitoring as background noise rather than high-stakes decision-making.

This posture is analytically striking: a man with access to every asset class, every alternative strategy, and every private deal chooses hyper-concentrated public equities. It suggests that at the highest levels of financial sophistication, conviction in specific sectors — not diversification — is seen as the real alpha generator.

The AI Hedge Fund: Aschenbrenner's $5B Conviction Bet

Leopold Aschenbrenner, a former OpenAI researcher who published the influential 'Situational Awareness' AI white paper, launched a hedge fund at age 22 and has scaled it to approximately $5 billion. His thesis, developed from inside one of the world's most advanced AI labs, is that mainstream institutions still systematically underestimate the pace and magnitude of AI's economic impact.

The fund's scale — $5B at 25 years old — is itself a signal. It reflects institutional capital flowing toward AI-native research talent, not just AI companies. Aschenbrenner's trajectory suggests that deep technical credibility on AI is now a competitive advantage in fund management, not just in product development.

Autopilot and the Democratization of Institutional Strategy

Autopilot has grown to $1.8B in assets under management by letting retail investors automatically mirror the publicly disclosed trades of politicians and hedge funds — without surrendering custody of their funds. The platform's marquee draw: a tracked portfolio of Nancy Pelosi's trades is up approximately 240% over three years, versus 30-40% for the S&P 500 over the same period.

The company's longer-term ambition is structural: it aims to replicate what BlackRock's Aladdin platform does for institutions — a portfolio marketplace generating $6B per year — and make it available to retail investors. Top 'pilots' (portfolio creators) already earn income from the platform, creating a supply-side incentive that solves the cold-start problem most fintech marketplaces struggle with.

This represents a meaningful shift in the investment landscape. Strategies that previously required institutional access, Bloomberg terminals, and compliance teams are now one-click products. The question is whether public disclosure data — inherently lagged — captures enough of the edge to justify the framing.

Invest in Your P&L: The Embedded-Tech Heuristic

Shaan Puri articulates a deceptively simple investment framework he calls 'investing in your P&L': buy equity in the software tools already embedded in your business that you couldn't switch off. Aaron Levie, CEO of Box, validated the logic — Box's own tech stack over 20 years would have outperformed most managed portfolios.

The insight is behaviorally grounded: the tools a business pays for month after month, despite rising costs and alternatives, are precisely the ones with durable competitive moats. This heuristic converts operational knowledge into investment conviction, giving operators an informational edge that pure financial analysts lack.

Alternative Assets: Hard Goods, Rare Earths, and Roll-Ups

Smart money is also finding outsized returns in overlooked physical markets. Two hedge fund managers bought a mine at the California-Nevada border and built MP Materials Corp into a $10 billion publicly traded company after raising just $20M — a rare-earth play that became a national security asset as the U.S. scrambled to onshore critical mineral supply chains.

In a parallel vein, Josh Weissenstein and his partner Cody have acquired 16 family campgrounds across 10 states, generating $20M in annual revenue on $60M raised, with a portfolio now valued at over $100M. They deliberately target a niche that private equity has historically ignored — family-oriented outdoor hospitality — exploiting fragmentation the same way early roll-up investors did in car washes or veterinary clinics.

Underpinning all of this is the sheer scale of private equity as an asset class: Carlyle Group, co-founded by David Rubenstein, now manages approximately $500 billion in assets. The institutions that built those pools of capital are the benchmark that Autopilot and other platforms are explicitly trying to democratize.

Open questions

Angles still unanswered — threads worth pursuing.

  1. If publicly disclosed congressional trade data generates 240% returns over three years, does that imply market inefficiency, survivorship bias in platform curation, or something more structurally concerning about information asymmetry in government?

    The Pelosi portfolio performance is extraordinary enough that it demands a serious causal explanation — one that has regulatory, legal, and market-structure implications.

  2. At what AUM does an AI-thesis hedge fund like Aschenbrenner's become self-defeating — i.e., too large to take the concentrated positions that generated the edge in the first place?

    The tension between conviction-based concentration and fund size is the central unsolved problem in hedge fund scaling, and AI funds face it faster than most.

  3. Is the 'invest in your P&L' heuristic actually alpha-generating, or does it just replicate a tech-heavy index with higher concentration risk?

    Validating the strategy requires distinguishing between the performance of embedded enterprise software and the broader tech market rally — a test that hasn't been rigorously run.

  4. How does the democratization of institutional strategies via copy-trading platforms change the behavior of the politicians and fund managers being copied — do they adapt once they know retail flows are tracking them?

    If copycat retail capital is large enough to move markets, the original signal deteriorates, creating a reflexivity problem that could undermine the entire category.

  5. What is the next category of fragmented physical assets — after campgrounds and car washes — that private equity hasn't yet targeted, and where does the roll-up math still hold?

    Each successful roll-up category attracts institutional competition that erodes returns; identifying the next uncrowded niche before that happens is the most actionable insight in alternative asset allocation.

References

  1. My First Million How the Ex-Goldman CEO actually invests his own money — Lloyd Blankfein “98% in risky assets: Lloyd Blankfein keeps 98% of his personal portfolio in risky assets, with roughly 75% in single stocks and the remainder in ETFs.”
  2. My First Million How the Ex-Goldman CEO actually invests his own money — Lloyd Blankfein “Tech, energy, financials — 3 core sectors: Lloyd Blankfein concentrates his personal investment portfolio across three sectors: technology, energy (his trading background), and financial services (hi…”
  3. My First Million 3 weird businesses doing $10M, $20M, $30M — Shaan Puri “Leopold Aschenbrenner, a former OpenAI researcher who published the 'Situational Awareness' AI white paper, launched a hedge fund at 22 and has grown it to approximately $5 billion. He found the over…”
  1. My First Million 3 weird businesses doing $10M, $20M, $30M — Brian “Autopilot lets retail investors automatically copy the trades of politicians and hedge funds using publicly reported data — without giving custody of funds away. The platform grew to managing $1.8B i…”
  2. My First Million 3 weird businesses doing $10M, $20M, $30M — Brian “Nancy Pelosi's tracked portfolio is up approximately 240% over 3 years versus the S&P 500's 30-40%. Autopilot bootstrapped its marketplace by manufacturing supply-side content from publicly available…”
  3. My First Million 3 weird businesses doing $10M, $20M, $30M — Brian “Autopilot's ultimate goal is to democratize what BlackRock Aladdin does for institutions — a portfolio marketplace that generates $6B/year — and bring it to retail investors. Top 'pilots' already ear…”
  4. My First Million I dropped out of college and built a $3.6B company from scratch — Shaan Puri “Shaan Puri calls it 'investing in your P&L' — just buy shares in the tools you're already paying for and couldn't switch off. Aaron Levie agrees: Box's tech stack over 20 years would have outperforme…”
  5. My First Million We decoded the business behind this influencer’s perfect life — Shaan Puri “MP Materials Corp: $10B valuation: Two hedge fund managers raised $20M, bought a mine at the California-Nevada border, and built MP Materials Corp into a $10 billion publicly traded company.”
  6. My First Million 3 weird businesses doing $10M, $20M, $30M — Josh Weissenstein “Josh Weissenstein and his partner Cody have acquired 16 family campgrounds across 10 states, generating $20M in annual revenue on $60M raised — with a portfolio worth over $100M. They specifically ta…”
  7. My First Million We found an app that lets you buy anything for $0 — Sam Parr “Carlyle Group $500B AUM: Carlyle Group, co-founded by David Rubenstein, now manages approximately $500 billion in assets — one of the largest private equity firms in the world.”

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