Howard Marks: when everyone thinks it is risky, it is less risky
Richard C. Wilson finished a Howard Marks book days before his Billionaire Insights talk and called it priceless for that market. He says it can help an investment team that is unsure what to do, or investors who are holding back. He returns to Marks often in his 2026 sessions.
Risk is upside down
Marks's point, as Richard tells it, is that risk feels high when prices have already fallen, so money goes further. The real risk was during the party, when everyone was excited. Richard says the conviction to act when things are wobbly is where value gets made.
Toxic industries, generational deals
In a 2026 session Richard says Marks finds his best deals when people write off a whole industry. Richard's example is people saying you would be an idiot to invest in multifamily. If many people believe that, some good assets will sell cheap.
Do not predict, look out the window
Richard notes that Marks does not try to predict the future. He tries to see which way the pendulum is swinging.
Let deals come to you
Richard also pulls a positioning idea from Marks. Oaktree's reputation brings it distressed deals where it can add value and set terms. Richard says most investors are not distressed buyers. They can still build a position where good deals in their niche reach them first.
In Richard's words
"The fact that you think it's risky makes it less risky." (Richard C. Wilson, Billionaire Insights talk)
"but to actually have the conviction to invest right now when it's not a sure thing and things are wobbly." (Billionaire Insights talk)
"you need to be able to stick your head out the window and see which way the pendulum is swinging." (2026 event, about 1:24:03)
How to use this
- When your investors hold back because the market feels risky, show them how much further their money goes now.
- Be most careful when everyone around you is excited.
- Make a list of the industries people are writing off, and look for good assets there.
- Build a reputation in your niche so sellers bring deals to you first.
Questions and answers
What does Howard Marks say about risk?
As Richard C. Wilson tells it, Marks says risk is lower when people think it is high, because prices have already fallen. The most risk is present when everyone is optimistic.
Does Howard Marks predict markets?
Richard says Marks does not try to predict the future. He tries to judge which way the pendulum is swinging.
Which Howard Marks book does Richard recommend?
He mentions The Most Important Thing in his August 2026 bootcamp.