10.16.25 - Warren Buffett had Benjamin Graham. Sheryl Sandberg had Larry Summers. Even Ray Dalio calls Paul Tudor Jones.
None of these people needed someone to teach them the basics. They needed someone to see what they couldn't see from inside their own situation.
The Graham-Buffett Dynamic
Warren Buffett credits Benjamin Graham with giving him more than techniques—Graham gave him an intellectual framework. Focus on intrinsic value. Demand a margin of safety. Treat "Mr. Market" as a servant, not a guide. As Buffett puts it: "Long ago, Ben Graham taught me that 'Price is what you pay; value is what you get.'"
That framework—seeing independent value rather than following market sentiment—became the foundation of Berkshire Hathaway.
Sheryl Sandberg had Larry Summers as her thesis advisor at Harvard, worked as his research assistant at the World Bank, and later served as his chief of staff at Treasury. These weren't just jobs—they were apprenticeships in how decisions get made at the highest levels. The relationship she's credited as formative to her career.
These relationships weren't about instruction. They were about seeing.
The Blind Spots of Success
Most successful people understand this instinctively in their careers. They build boards, advisory groups, peer networks. They know that being inside something makes it impossible to see it clearly.
Yet with personal wealth, that same instinct often disappears.
Maybe money feels too personal to discuss. Maybe after building something from nothing, managing investments seems straightforward by comparison. Or maybe when something's working, it's hard to imagine it breaking.
Two Stories About Perspective
A business owner in his fifties had built $4M in net worth. Disciplined saver. Zero debt. By every measure, crushing it. Eighty-five percent of his wealth sat in his business.
His logic was sound: "My business is stable. I know it better than any investment. Why would I sell and pay taxes just to buy something I understand less?"
Then someone asked him: "What happens if the business has three bad years in a row right when you want to retire?"
The question reframed his thinking. Not because his business was risky, but because he'd never separated his timeline from his business's timeline. He started diversifying gradually. Three years later, when his industry contracted, he had options instead of obligations.
Another story: An executive, sixty-two years old, $6M net worth, still grinding. When asked why she was still working, she said: "I want to hit $8M before I retire."
"Why $8M?" Long pause. "I don't know. It just feels like the right number."
They ran the math together. Her lifestyle cost $200K annually. At a conservative withdrawal rate, $6M already covered it. She was working two more years for a number that had no connection to life.
What Outside Eyes See
Neither of these people lacked intelligence or discipline. They'd built successful careers and significant wealth. But proximity blinds us to patterns.
When you're inside your own situation, certain assumptions become invisible. The concentrated position doesn't feel risky because it's been fine so far. The arbitrary target feels necessary because you've been chasing it for years. The tax strategy you're missing doesn't exist because you don't know to look for it.
The Paradox of Independence
There's profound satisfaction in doing something yourself. In knowing you built it, managed it, succeeded through your own judgment and effort.
But even lone wolves hunt in packs when it matters.
The most independent thinkers—from Charlie Munger to Howard Marks—constantly test their ideas against other perspectives. Not because they lack confidence, but because they know that confidence without verification is just opinion.
They read voraciously. They maintain networks of people who think differently. They actively seek disconfirming evidence. They know that the best decision is rarely the first one you see.
Finding Your Own Graham
The right outside perspective doesn't have to come from an advisor. It might be a peer group. A mentor. A particularly sharp friend who asks uncomfortable questions. Even books that challenge your assumptions.
The source matters less than the practice: regularly stepping outside your own perspective to see what you might be missing.
Some questions worth finding someone to explore:
- What risks have I normalized because they've been fine so far?
- What am I optimizing for, and does it still matter?
- If I were starting from scratch, would I set things up this way?
- What would someone who disagrees with me point out?
The Real Edge
In investing, like in business, the edge comes from asking better questions.
Graham didn't give Buffett answers. He gave him a framework for finding them.
The best investors seek outside perspective not because they need help, but because they know that testing ideas against views they couldn't generate themselves leads to better decisions.
Your wealth is the stored energy of everything you've built. It deserves the same rigor you applied to building it in the first place.