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The Legend Michael Mauboussin on Acquired!

We sit down with the one & only Michael Mauboussin to dive deep into his incredible body of work: untangling skill and luck, measuring moats, persistence of returns in venture capital, decision making and — particularly timely — expectations investing and how to think about valuations in the current 2021 market environment. (!!) Michael's work is maybe our most frequent carve out on Acquired, so we're pumped to finally have a chance to interview the man himself. Big thank you to Patrick O'Shaughnessy and Brent Beshore for introducing us all at Capital Camp this year! If you love Acquired and want more, join our LP Community for access to over 50 LP-only episodes, monthly Zoom calls, and live access for big events like emergency pods and book club discussions with authors. We can't wait to see you there. Join here at: https://acquired.fm/lp/ **Sponsors** - Thanks to SoftBank Latin America for being our presenting sponsor for this special episode. If you are an entrepreneur, employee, other investor or simply someone who's interested in learning about the best young companies in LatAm right now, get in touch with them at: https://bit.ly/acquiredsoftbanklatam , and tell them that Ben and David sent you! - You can get learn more about careers at their portfolio company QuintoAndar at https://carreiras.quintoandar.com.br - Thank you as well to Modern Treasury and to Fundrise. You can learn more about them at: - https://bit.ly/acquiredmoderntreasury (and you can find our reverse interview with them at https://www.moderntreasury.com/acquired ) - https://bit.ly/acquiredfundrise **Jobs!** - Big news — we now have a full Acquired Job Board! It's a one-stop-shop with all the very best opportunities from the amazing companies in the Acquired community, including folks like Solana, Italic, Pilot, RabbitHole, Modern Treasury, Vouch, Zapier, Levels and more. AND, if you're more casually open to opportunities, we have a form you can fill out and we'll handpick the best ones and personally send to you as they come up. Check it out at https://www.acquired.fm/jobs **Links:** - Michael's wonderful talk at Google: https://youtu.be/1JLfqBsX5Lc - The new revised edition of Expectations Investing: https://www.amazon.com/Expectations-Investing-Reading-Returns-Heilbrunn/dp/0231203047/ - The Success Equation: https://www.amazon.com/The-Success-Equation-Untangling-Investing/dp/1422184234/ - Measuring the Moat: https://research-doc.credit-suisse.com/docView?language=ENG&format=PDF&sourceid=csplusresearchcp&document_id=1066439791&serialid=4uA2wHojCvFKzqWfwIyDvkSN1pkXRpb43LvyclLcJsk%3D&cspId=null - Public to Private Equity: https://www.morganstanley.com/im/publication/insights/articles/articles_publictoprivateequityintheusalongtermlook_us.pdf *‍Note: Acquired hosts and guests may hold assets discussed in this episode. This podcast is not investment advice, and is intended for informational and entertainment purposes only. You should do your own research and make your own independent decisions when considering any financial transactions.*

Ben GilberthostDavid RosenthalhostMichael Mauboussinguest
Oct 4, 20211h 34mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Michael Mauboussin on expectations, moats, and decision-making in markets

  1. Michael Mauboussin explains the core framework of “Expectations Investing”: prices embed market expectations, so investors should reverse-engineer what must be true and then judge whether those expectations are too optimistic or pessimistic.
  2. He discusses how the shift from tangible to intangible investment (software, R&D, brand, customer acquisition) breaks many traditional accounting-based heuristics and makes cash-flow and unit economics analysis more important than ever.
  3. Mauboussin outlines a structured way to “measure the moat,” connecting strategy to returns on invested capital and clarifying how low-cost vs. differentiation strategies show up in margins and capital velocity.
  4. The conversation broadens to decision-making tools (base rates, pre-mortems, red teams, journaling), complexity and reflexivity (e.g., Tesla), and the skill/luck dynamics that make persistent outperformance increasingly rare in efficient, highly skilled markets.

IDEAS WORTH REMEMBERING

5 ideas

Start with price: reverse-engineer expectations before building conviction.

Mauboussin argues most investors build a valuation from their own assumptions, but the better starting point is asking, “What do I have to believe for today’s price to make sense?” Then compare your expectations to the market’s and act only when you have a meaningful differential view.

Think probabilistically, not point-estimate-ically.

Expectations investing is inherently scenario-based: the current price reflects a distribution of outcomes. Sound decisions come from mapping multiple plausible futures (with probabilities) rather than anchoring on a single forecast.

The economy’s shift to intangibles makes earnings less informative.

Because more investment now occurs in items expensed on the income statement (R&D, software, CAC, training, brand), reported profitability can understate value creation. This strengthens the case for focusing on free cash flow and understanding which “expenses” are really growth investments.

Moats should be grounded in ROIC relative to cost of capital and peers.

A true competitive advantage is both absolute (returns above cost of capital) and relative (better economics than competitors). ROIC provides a quantitative anchor, while industry structure and competitive dynamics explain whether those returns can persist.

Strategy type is often visible in financials via margins and capital velocity.

Low-cost producers tend to show low margins but high capital turnover (sales/invested capital). Differentiators tend to show high margins but lower capital velocity—two paths that can both produce strong ROIC depending on execution and industry context.

WORDS WORTH SAVING

5 quotes

A stock price reflects a set of expectations about future financial performance.

Michael Mauboussin

What do I have to believe for this to make sense?

Michael Mauboussin

The ultimate driver value of business is cash, not accounting earnings.

Michael Mauboussin

In activities where both skill and luck contribute to outcomes, as skill increases, luck becomes more important.

Michael Mauboussin

Extraordinary streaks are a combination of skill and luck.

Michael Mauboussin

Expectations Investing (reverse DCF)Cash flows vs. accounting earningsIntangibles and modern financial statementsMeasuring moats and ROICComplex adaptive systems and real optionsReflexivity in high-flying stocksDecision-making tools: base rates, pre-mortems, red teams, journalsSkill vs. luck, paradox of skill, persistence in VC

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