Howard Marks

Marks calls it second-level thinking. First-level thinking is: "This company has good prospects — I''ll buy the stock." Second-level thinking is: "This company has good prospects, but everyone already knows that.

The stock is priced for perfection. I''ll pass." Being right about fundamentals isn''t enough.

You also have to be right about what the market already knows and what the price already reflects.

His other major concept: risk is not volatility. Risk is the probability of permanent loss of capital.

A bond that drops 30% in price isn''t necessarily risky if the underlying company is sound and will pay the debt back. A bond that barely moves but is issued by a company about to default is extremely risky.

He thinks most investors confuse the two, constantly.

Mark Zuckerberg

Zuckerberg does not invest in the traditional sense — he builds and holds. He controls Meta through a dual-class share structure that gives him roughly 54% of voting power with less than 15% economic ownership, meaning no board or shareholder can remove him regardless of how the stock performs.

He has made massive bets inside Meta — on mobile (right), Instagram (very right), WhatsApp (right), VR/metaverse (wrong so far), and AI (still playing out). His investment thesis is that social connectivity is a fundamental human need and whoever owns the infrastructure owns everything.

Howard Marks

His core ideas, from The Most Important Thing: understand market cycles — everything is cyclical, including investor sentiment, credit availability, and valuations. Recognise where you are in a cycle and position accordingly.

Control risk obsessively — not because you''re afraid, but because avoiding the big losses is the primary driver of long-term returns. Practice second-level thinking — don''t just ask what''s true, ask what''s already priced in.

And be patient. The best opportunities come during crises, when forced sellers are creating discounts that wouldn''t exist in calmer markets.

Mark Zuckerberg

Zuckerberg thinks in decades, not quarters. His core belief is that the most important technology of the next century is whoever connects people at scale — first through social networks, then through AR/VR, and now through AI agents.

He is willing to absorb years of losses on bets he believes in. He says he would rather make a big bet and be wrong than be timid and miss the next platform shift.

Howard Marks

Marks is deeply conservative about the downside. His framework: focus on risk control, not return maximisation.

Superior long-term returns come from avoiding the big losses, not from hitting the biggest wins. This sounds obvious.

Almost no one actually practises it. He has written extensively about how human psychology — overconfidence in good times, panic in bad times — makes sustained risk control incredibly hard.

He''s comfortable in distressed situations that most investors find too ugly to look at. The apparent ugliness is where the value is.

Mark Zuckerberg

Zuckerberg spent $36 billion on Reality Labs — VR and AR — between 2019 and 2023, with little to show in revenue. He did not flinch.

He also bet Facebook's entire business model on going mobile in 2012, acquired Instagram for $1 billion when it had 13 employees and no revenue, and has held through Congressional hearings, advertiser boycotts, and multiple existential challenges from competitors. His personal financial risk is minimized by his dual-class share structure — he controls voting power regardless of what the stock does, so no board or activist investor can force his hand.

He can lose at scale for as long as he believes the thesis.

Howard Marks

He lives in Los Angeles, where Oaktree is based. He is still active as co-chairman and still writing memos — he''s written over 100 since 1990.

He donates meaningfully to Penn and other academic institutions. He gives speeches at conferences and academic events.

He is considerably more understated than many hedge fund managers of comparable success — he''s interested in ideas, not attention. His son Andrew Marks worked in the film industry, which Marks has described as a source of pride regardless of the career choice.

Mark Zuckerberg

He wore the same grey t-shirt every day for years — he said it reduced decision fatigue. He trains MMA and Brazilian jiu-jitsu seriously, competing in actual tournaments.

He wakes up early, spends mornings with his family, and starts work at 8am. He has spoken about designing his schedule to protect creative work in the mornings.

He reportedly does not check email first thing.

Howard Marks

2008–2009. When the financial crisis hit, high-yield bond markets froze.

Perfectly sound debt was trading at catastrophic discounts because panic selling created forced sellers. Oaktree, which had been raising a distressed debt fund precisely for this type of environment, deployed capital aggressively through the crisis.

Fund VI, raised in 2008, became one of the most successful distressed debt funds in history. The returns were exceptional because the panic-induced discounts were exceptional.

Marks had been writing about exactly this type of opportunity for years. When it arrived, he was ready for it.

Mark Zuckerberg

Acquiring Instagram for $1 billion in 2012. Instagram was growing fast, potentially threatening Facebook's dominance with younger users.

Facebook bought it. It now generates an estimated $40-60 billion in annual revenue.

Many consider it the best acquisition in tech history on a return basis — $1 billion in for what became a $100B+ asset.

Howard Marks

By his own account, he''s avoided most of the disasters. His framework is explicitly designed to prevent catastrophic errors.

The closest thing to a meaningful mistake: being too early warning about the dot-com bubble — he published a memo in January 2000 laying out why tech valuations were unsustainable. He was right, but the bubble ran for another three months before collapsing.

Being early is expensive. He''s also honest that avoiding spectacular losses sometimes means missing spectacular gains — that''s the trade-off he''s consciously made.

Mark Zuckerberg

The metaverse bet. From 2021 to 2023, Meta spent over $50 billion on Reality Labs — its VR and metaverse division — and generated minimal revenue.

The division lost $16 billion in 2023 alone. Meta's stock fell nearly 75% at its 2022 trough.

Zuckerberg was widely mocked, called the metaverse a disaster, and faced enormous internal and external pressure. He then pivoted hard to AI and the stock recovered.

The metaverse losses remain one of the most expensive executive vanity projects in corporate history.

Howard Marks

Howard Marks grew up in Flushing, Queens. He studied finance at the Wharton School of the University of Pennsylvania and got his MBA from the University of Chicago Booth School of Business.

He started his career at Citibank, where he ran their bond department and later their convertible securities and high-yield debt portfolios. He moved to TCW Group in Los Angeles in 1985 to manage distressed debt and high-yield bonds.

In 1995, he co-founded Oaktree Capital Management with six colleagues from TCW. The idea: focus specifically on alternative and distressed investments — high-yield bonds, distressed debt, convertible securities, private credit.

Oaktree went public in 2012 and was acquired by Brookfield Asset Management in 2019 for $4.7 billion. Marks stayed on as co-chairman.

Through all of it — from 1990 to today — he was writing the memos.

Mark Zuckerberg

Mark Zuckerberg launched Facebook from his Harvard dorm in February 2004. By the end of 2004, the site had 1 million users.

He turned down a $1 billion acquisition offer from Yahoo in 2006. By 2012, Facebook went public at a $104 billion valuation — the largest tech IPO in history at the time.

The stock immediately fell 50%. It then recovered to become one of the most valuable companies in the world.

In 2012, Facebook acquired Instagram for $1 billion (now worth over $100 billion). In 2014, it acquired WhatsApp for $19 billion.

In 2021, he rebranded the parent company to Meta to signal a pivot to the metaverse — a move that cost over $50 billion in investment and destroyed significant shareholder value before the company course-corrected toward AI.

Howard Marks

Oaktree Capital Management, co-founded in 1995, manages roughly $170 billion across credit strategies. The firm specialises in high-yield bonds, distressed debt, senior loans, convertible securities, and real estate credit.

Distressed debt, in plain English, works like this: when a company gets into trouble, its bonds get cheap. If the company recovers — or even partially recovers — those bonds can multiply in value.

The skill is telling the difference between a company that''s temporarily distressed and one that''s actually going bankrupt. Marks has been making that call for 50 years.

Oaktree was acquired by Brookfield in 2019 for $4.7 billion — a reasonable indicator that the track record speaks for itself.

Mark Zuckerberg

Meta Platforms (CEO and controlling shareholder — holds majority voting control through supervoting shares). Key acquisitions: Instagram (2012, $1B), WhatsApp (2014, $19B), Oculus VR (2014, $2B).

Chan Zuckerberg Initiative (co-founded with wife Priscilla Chan — philanthropic LLC).

Howard Marks

Wharton School of the University of Pennsylvania, BS in Finance summa cum laude, Phi Beta Kappa, 1967. University of Chicago Booth School of Business, MBA, 1969.

He has said that Chicago — where the efficient market hypothesis was gospel — taught him exactly what the prevailing wisdom was, which made it easier to know when to disagree with it.

Mark Zuckerberg

Harvard University — studied computer science and psychology. Dropped out in 2004 to move Facebook to Palo Alto.