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Dear Shareholder: The best executive letters from Warren Buffett, Prem Watsa and other great CEOs
The shareholder letters of corporate leaders are a rich source of business and investing wisdom. There is no more authoritative resource on subjects ranging from leadership and management to capital allocation and company culture. But with thousands of shareholder letters written every year, how can investors and students of the corporate world sift this vast swathe to unearth the best insights? Dear Shareholder is the solution! In this masterly new collection, Lawrence A. Cunningham, business expert and acclaimed editor of The Essays of Warren Buffett, presents the finest writers in the genre of the shareholder letter, and the most significant excerpts from their total output. Skillfully curated, edited and arranged, these letters showcase the ultimate in business and investment knowledge from an all-star team. Dear Shareholder holds letters by more than 20 different leaders from 16 companies. These leaders include Warren Buffett (Berkshire Hathaway), Tom Gayner (Markel), Kay Graham and Don Graham (The Washington Post and Graham Holdings), Roberto Goizueta (Coca-Cola), Ginni Rometty (IBM), and Prem Watsa (Fairfax). Topics covered in these letters include the long-term focus, corporate culture and commitment to values, capital allocation, buybacks, dividends, acquisitions, management, business strategy, and executive compensation. As we survey the corporate landscape in search of outstanding companies run by first-rate managers, shareholder letters are a valuable resource. The letters also contain a wealth of knowledge on the core topics of effective business management. Let Dear Shareholder be your guide.
504 pages, Kindle Edition
First published April 14, 2020
95 people are currently reading
527 people want to read
About the author
Lawrence A. Cunningham
43 books143 followersLawrence Cunningham, who goes by Larry, has published many books, including:
Berkshire Beyond Buffett: The Enduring Value of Values
The Essays of Warren Buffett: Lessons for Corporate America
Contracts in the Real World: Stories of Popular Contracts and Why They Matter
The AIG Story
He loves teaching (a prawf at GW), windsurfing, reading, and spending time with his wife and two daughters, preferably at the beach.
On Amazon, Cunningham has been ranked one of the top 100 authors in the category of business and investing.
Berkshire Beyond Buffett: The Enduring Value of Values
The Essays of Warren Buffett: Lessons for Corporate America
Contracts in the Real World: Stories of Popular Contracts and Why They Matter
The AIG Story
He loves teaching (a prawf at GW), windsurfing, reading, and spending time with his wife and two daughters, preferably at the beach.
On Amazon, Cunningham has been ranked one of the top 100 authors in the category of business and investing.
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Displaying 1 - 9 of 9 reviews
January 6, 2024
Highly repetitive and unstructured extracts of corporatese that isn't very illuminating the first time around, let alone the number of times it's repeated here. Want to read 10,000 words of Pepsi's CEO repeatedly bragging about reducing water use? No, me neither. IBM's CEO extolling the virtues of cloud? Nope again. Either Cunningham did a bad job of selecting CEO letters, or CEO letters are a poor source of illumination. Certainly he did a poor job of editing them, and he made only a minimal effort at analysing them - and again did so poorly. There's no attempt to parse the letters for gold versus bullshit, perhaps because he can't actually tell the two apart.
October 24, 2025
Just finished Dear Shareholder. Overall, I’d say it’s a mixed experience — parts of it were fantastic, but others felt shallow. The concept of the book is great: curating excerpts from top shareholder letters to show how great executives think about capital allocation, culture, and long-term value creation. But it’s uneven.
The Goizueta, Bezos, and Google sections were disappointingly short — barely scratched the surface of their thinking. The chapters on Indra Nooyi and Ginni Rometty also leaned too heavily into ESG and corporate-speak, the kind of surface-level PR that feels disconnected from true capital stewardship.
That said, there were a few standouts that made the book worthwhile.
Morningstar really impressed me — their clarity about their moat, pricing power, and competitive position was refreshing. They describe their business in the same language a long-term investor would use: network effects, brand trust, and subscription stickiness as compounding advantages. It’s Buffett-like in tone — rational, simple, and self-aware.
Leucadia and Seacor were also excellent. Both reflected a disciplined, contrarian approach to capital allocation — high returns on incremental capital, patience in dislocated markets, and total comfort with being out of step with the crowd. They care more about intrinsic value math than market popularity.
Cimpress stood out for a different reason. I liked seeing the evolution of their letters over multiple chapters — watching a company go from a small print-on-demand business to a genuine capital allocation machine. It’s rare to see that kind of longitudinal record of growth and self-reflection. Cimpress treats capital allocation as the core craft of management.
The epilogue tied everything together nicely. It describes what separates first-rate managers from the rest: patience, modesty, clarity, and a deep understanding of capital allocation, buybacks, acquisitions, and people. These companies are “wonderful” not because they’re flashy, but because their leaders compound value through intelligent restraint and long-term thinking.
“Wonderful companies run by first-rate managers have modesty, openness, and command in communication — with a clear understanding of capital allocation, buybacks, acquisitions, and management of people.”
Some sections I photographed are worth keeping close:
1992 – Investing
• Emphasizes reinvesting cash flow into high-return opportunities.
• Looks for businesses with low capital intensity, pricing power, and distinctive quality.
• Strong reminder that saying no matters as much as saying yes.
“Knowing when to say ‘no’ is just as important as knowing when to say ‘yes.’”
2000 – Tumult
Written during the dot-com bubble — still feels timeless. It warns against financial euphoria and reminds investors that economic gravity always reasserts itself.
“Economics has its own gravitation-like forces that work over time and can only be ignored at investors’ peril.”
There’s also a nice reflection on productivity — that America’s true strength is self-renewal, not blaming others (in that case, Japan). And a nod to how innovation, like the early internet, was reshaping everything — but still subject to valuation discipline.
The epilogue ends with a line I really liked:
“Some books are to be skimmed, others read quickly, and a few endlessly examined. This one falls into the last category.”
That’s true — but only for the best parts. I’d put Dear Shareholder in the “selectively examined” category. When it hits, it really hits — especially the letters that combine clear thinking with humility and discipline. The rest serves as a reminder of how easily shareholder communication drifts into noise when management loses focus on capital allocation and true compounding.
Main takeaway: The best letters — Morningstar, Leucadia, Seacor, Cimpress — show that clarity, candor, and discipline are timeless. The others prove how rare those qualities actually are.
The Goizueta, Bezos, and Google sections were disappointingly short — barely scratched the surface of their thinking. The chapters on Indra Nooyi and Ginni Rometty also leaned too heavily into ESG and corporate-speak, the kind of surface-level PR that feels disconnected from true capital stewardship.
That said, there were a few standouts that made the book worthwhile.
Morningstar really impressed me — their clarity about their moat, pricing power, and competitive position was refreshing. They describe their business in the same language a long-term investor would use: network effects, brand trust, and subscription stickiness as compounding advantages. It’s Buffett-like in tone — rational, simple, and self-aware.
Leucadia and Seacor were also excellent. Both reflected a disciplined, contrarian approach to capital allocation — high returns on incremental capital, patience in dislocated markets, and total comfort with being out of step with the crowd. They care more about intrinsic value math than market popularity.
Cimpress stood out for a different reason. I liked seeing the evolution of their letters over multiple chapters — watching a company go from a small print-on-demand business to a genuine capital allocation machine. It’s rare to see that kind of longitudinal record of growth and self-reflection. Cimpress treats capital allocation as the core craft of management.
The epilogue tied everything together nicely. It describes what separates first-rate managers from the rest: patience, modesty, clarity, and a deep understanding of capital allocation, buybacks, acquisitions, and people. These companies are “wonderful” not because they’re flashy, but because their leaders compound value through intelligent restraint and long-term thinking.
“Wonderful companies run by first-rate managers have modesty, openness, and command in communication — with a clear understanding of capital allocation, buybacks, acquisitions, and management of people.”
Some sections I photographed are worth keeping close:
1992 – Investing
• Emphasizes reinvesting cash flow into high-return opportunities.
• Looks for businesses with low capital intensity, pricing power, and distinctive quality.
• Strong reminder that saying no matters as much as saying yes.
“Knowing when to say ‘no’ is just as important as knowing when to say ‘yes.’”
2000 – Tumult
Written during the dot-com bubble — still feels timeless. It warns against financial euphoria and reminds investors that economic gravity always reasserts itself.
“Economics has its own gravitation-like forces that work over time and can only be ignored at investors’ peril.”
There’s also a nice reflection on productivity — that America’s true strength is self-renewal, not blaming others (in that case, Japan). And a nod to how innovation, like the early internet, was reshaping everything — but still subject to valuation discipline.
The epilogue ends with a line I really liked:
“Some books are to be skimmed, others read quickly, and a few endlessly examined. This one falls into the last category.”
That’s true — but only for the best parts. I’d put Dear Shareholder in the “selectively examined” category. When it hits, it really hits — especially the letters that combine clear thinking with humility and discipline. The rest serves as a reminder of how easily shareholder communication drifts into noise when management loses focus on capital allocation and true compounding.
Main takeaway: The best letters — Morningstar, Leucadia, Seacor, Cimpress — show that clarity, candor, and discipline are timeless. The others prove how rare those qualities actually are.
July 24, 2025
I have read letters from Jeff Bezos, Warren Buffett, and the original sources are always better because you get to see the whole picture and progression of a company from the ground up. This book just cherry-picked a few from some companies that you may or may not be interested in.
What I like to do is just go on Amazon and use the Kindle version's read sample button so you get access to the entire table of contents if you scroll up a little bit. Then you will see what kind of companies are covered in this one. I didn't care about Coca-Cola or Pepsi. I don't know why both had to be included in this one. I was very interested in Constellation Software, Amazon, Google, yet the rest is a little bit of a hit and miss depending on what you want.
But I've already read Buffett's letters for like 2,000 pages. Overall, it's not the most life-changing thing, but I think it was worth it. But it dragged on a little bit too long, and I kinda don't see why these specific letters were picked from each company. I mean they'll try to go for those where something interesting happened, but it is very very subjective. At least you get to learn about the corporate culture and capital allocation philosophies of these leaders and managements. And I'm sure some financial knowledge will rub off on you.
What I like to do is just go on Amazon and use the Kindle version's read sample button so you get access to the entire table of contents if you scroll up a little bit. Then you will see what kind of companies are covered in this one. I didn't care about Coca-Cola or Pepsi. I don't know why both had to be included in this one. I was very interested in Constellation Software, Amazon, Google, yet the rest is a little bit of a hit and miss depending on what you want.
But I've already read Buffett's letters for like 2,000 pages. Overall, it's not the most life-changing thing, but I think it was worth it. But it dragged on a little bit too long, and I kinda don't see why these specific letters were picked from each company. I mean they'll try to go for those where something interesting happened, but it is very very subjective. At least you get to learn about the corporate culture and capital allocation philosophies of these leaders and managements. And I'm sure some financial knowledge will rub off on you.
March 25, 2021
This books is very relevant for aspiring long-term value investors. There is a lot you can learn from the best minds in business and this books is just that. A key thing that this book sort of does is that it gives a timelapse view of their own thoughts and growth (in knowledge) and insight and that is quite something to learn and understand.
There are quite a few gems like Why dividends aren't necessarily good, Why Stockbuy backs are good but companies can make evil use of them , How to think about the future and worry less about the next quarter or even year, How to think about fluctuations in stock prices - things that are explained really well by the authors.
I would just take a point down for areas where I felt should have been edited out like that section in IBM and few other companies where I felt the analysis or the articulation was a bit mundane and text-book Annual report speak.
There are quite a few gems like Why dividends aren't necessarily good, Why Stockbuy backs are good but companies can make evil use of them , How to think about the future and worry less about the next quarter or even year, How to think about fluctuations in stock prices - things that are explained really well by the authors.
I would just take a point down for areas where I felt should have been edited out like that section in IBM and few other companies where I felt the analysis or the articulation was a bit mundane and text-book Annual report speak.
December 7, 2024
Highlights how unique Buffett is in applying shareholder friendly policies, consistently over a long period of time. Even case studies included in the book as exemplary have instances of making changes to suit management when existing policies no longer suit or become less attractive. Great section on Mark Leonard of Constellation Software. Interesting comments on p224 about acquisitions providing better IRR than internal R&D and sales and marketing projects. Hires internally because mutual trust and loyalty take years to build and newly hired smart and/or manipulative mercenaries can take years to identify and root out. Considered sell side analysts models OK, but future organic growth rate assumptions were too low.
April 29, 2023
Really enjoyed this compilation.
I initially read it out of interest of Prem Watsa, views on capital allocation, but within I found so much more from the various investors and CEOs.
Definitely would recommend.
I initially read it out of interest of Prem Watsa, views on capital allocation, but within I found so much more from the various investors and CEOs.
Definitely would recommend.
May 5, 2024
Phenomenal book filled with alpha-generating investment wisdom. This book deserves shelf space. Not a book you read just once.
October 18, 2025
Hagiographic, common sense. The good thing about this book is that it shows the importance of writing a transparent shareholder letter. Otherwise just read Buffett if you want to learn how and why.
June 6, 2021
Good compilation of shareholder letters. Great indication of great companies.
Displaying 1 - 9 of 9 reviews