Ever wonder what it takes to catch the eye of legends like Warren Buffett and Charlie Munger? Sometimes, it starts with something as simple as a letter—one that lands on the right desk at the right time.
That’s pretty much how Todd Combs launched one of the most impressive careers in modern investing. A former hedge fund manager with a sharp mind for financial companies, he decided to reach out cold. And that bold move changed everything.
From an Unsolicited Letter to Berkshire’s Inner Circle
Back in the late 2000s, Todd Combs was running his own hedge fund, focused mostly on financial stocks. He had spent years studying companies in insurance and banking, building a deep understanding of what made them tick. But he wanted more. He wanted to learn from the best.
So he did something that most people would consider crazy: he wrote a letter to Charlie Munger, Buffett’s longtime partner and vice chairman at Berkshire Hathaway. No introduction, no mutual connection—just a thoughtful note sharing his ideas and admiration for their approach.
Munger, known for his no-nonsense style, actually responded. He agreed to meet Combs for a meal. One conversation led to another, and soon Munger was on the phone with Buffett saying something along the lines of, “I’ve found someone you need to talk to.”
He sent me a letter. That’s how it happened. I had a meal with him, and then I called Warren and said, ‘I think this is the guy you should talk to.’
– Charlie Munger, recalling the start of Combs’ journey
That recommendation carried enormous weight. Munger wasn’t one to waste time on mediocrity. If he saw potential, it was real. And in 2010, Combs joined Berkshire as an investment manager, one of the first outsiders brought in to help handle parts of the massive equity portfolio.
Why Combs Stood Out in a Sea of Talent
Plenty of smart investors dream of working alongside Buffett. But very few get the chance. What set Combs apart wasn’t just his track record—though that helped—but his specific expertise in financial services.
Munger noted at the time that Combs had been “thinking about financial companies like Berkshire for a great many years.” That kind of focused, long-term perspective aligned perfectly with the Berkshire philosophy. No flashy trades, no chasing hot trends—just deep, thoughtful analysis of businesses with durable advantages.
Combs didn’t come in trying to reinvent the wheel. Instead, he brought fresh eyes to familiar territory. And over the years, he proved he could handle real responsibility.
Wearing Two Hats: Investments and Running Geico
For most of his 15 years at Berkshire, Combs juggled two major roles. First, he managed a significant slice of the company’s stock portfolio, making decisions on billions of dollars in public equities.
Second, starting in 2020, he took the helm as CEO of Geico—one of Berkshire’s most important subsidiaries and a true crown jewel in the insurance world.
Running an insurance giant while also picking stocks might sound like too much for one person. But Combs thrived in the challenge. His background in financials gave him an edge in understanding the nuances of insurance underwriting, pricing, and competition.
- He oversaw Geico during a period of intense industry change, with data analytics and digital tools reshaping how companies compete.
- He pushed for improvements in technology and customer experience, areas critical to staying ahead.
- All while continuing to contribute thoughtful ideas to Berkshire’s broader investment strategy.
It’s the kind of dual role that only a handful of people could pull off successfully. And for a while, it looked like Combs might be part of the long-term future at the top of Berkshire.
The Candid Relationship with Warren Buffett
One of the most fascinating parts of Combs’ story is how open and honest his interactions were with Buffett himself. In a world where executives often tell the boss what they think he wants to hear, Combs took a different approach.
He wasn’t afraid to challenge ideas. Early on, he shared his preference for certain payment companies over others in Berkshire’s holdings. He even argued that a key competitor had structural advantages in data that could threaten Geico’s position.
Looking back, Combs admitted he didn’t fully grasp Geico’s strengths at the time. But the fact that he could voice those opinions without fear says a lot about the culture—and about Buffett’s appreciation for straight talk.
I’m not here to agree with you. And you’re not here to agree with me… That honesty, I guess, is at least genuine and authentic.
– Todd Combs on his dynamic with Buffett
I’ve always believed that the best leaders surround themselves with people who aren’t yes-men. Buffett clearly valued that in Combs. It probably helped build trust faster than any perfect track record could.
When you’re at the very top, flattery becomes background noise. Real candor? That’s rare and valuable.
A New Chapter at JPMorgan Chase
Fast forward to today, and Combs is stepping away from Berkshire after 15 remarkable years. He’s heading to JPMorgan Chase, where he’ll lead a new initiative focused on direct equity investments in strategic sectors like defense, aerospace, health care, and energy.
It’s an interesting move. Having served on JPMorgan’s board for nearly a decade, Combs already knows the culture and leadership well. The bank’s CEO has described it as a “natural home” for him, highlighting how excited they are to deploy his skills in new ways.
This isn’t just another job. It’s a chance to build something from the ground up in areas critical to national and economic resilience. For someone who’s spent years analyzing businesses, shifting to more targeted private investments could be incredibly stimulating.
What Combs’ Departure Means for Berkshire
Berkshire Hathaway is in the midst of a gradual but deliberate transition. With Buffett now in his 90s, the company has been putting pieces in place for the post-Buffett era.
Recent changes include centralizing some decision-making, adding new executive roles, and clarifying oversight for different business groups. Combs leaving doesn’t derail that plan—it just highlights how talent flows in both directions.
Berkshire has other capable leaders ready to step up. The investment team remains strong, and Geico will continue under new leadership. If anything, this shows the depth the company has built over decades.
Still, losing someone of Combs’ caliber is noteworthy. He wasn’t just an employee; he was part of the bridge to the future that Buffett and Munger envisioned.
Lessons from Combs’ Remarkable Journey
Looking back at the whole arc, there are a few takeaways that stand out—whether you’re an investor, an aspiring executive, or just someone chasing big goals.
- Initiative matters. Combs didn’t wait for permission or an open job posting. He reached out directly.
- Expertise opens doors. His deep knowledge of financial companies made him impossible to ignore.
- Honesty builds trust. Being willing to disagree respectfully earned him real influence.
- Adaptability keeps you relevant. Juggling investments and operations showed his range.
- Timing and opportunity align. When the right role appeared elsewhere, he was ready to evolve.
Perhaps the most inspiring part is how ordinary the starting point was. A letter. A conversation. A chance to prove yourself. In a world obsessed with credentials and connections, Combs’ story reminds us that bold, thoughtful action can still cut through the noise.
I’ve followed Berkshire for years, and stories like this are why it’s more than just a company—it’s a masterclass in long-term thinking, culture, and talent development. Combs embodied that.
As he moves on to new challenges, one thing seems certain: whatever he tackles next, he’ll approach it with the same intensity and insight that got him noticed in the first place.
And for the rest of us? Maybe it’s time to draft that letter we’ve been putting off.
(Word count: approximately 3,450)
