Real correspondence from the people running real companies — and what it reveals about leadership.
Topic
Capital allocation, margins, and the numbers leaders defend.
40 letters · most recent first
Peter Stern & Matt Fischer & Philip Schiller & Carson Oliver & Adrian Ong ·Apple Inc. / Match Group ·28 JAN 2019
When you're a top customer paying a rack-rate meant for someone else, quantify the mismatch and name the comparable — don't complain, benchmark.
Sam Altman ·OpenAI ·31 AUG 2018
If your mission truly comes first, your legal structure has to prove it — even to yourself.
Ilya Sutskever ·OpenAI ·13 SEP 2017
In a founding negotiation, spelling out who decides what — in writing — is more valuable than any equity number.
David Ebersman & Dan Levy ·Meta (Facebook) ·16 APR 2012
The cost savings will still be there in a year. The momentum won't.
Chip Hall & Chris LaSala & Gargi Sur & Max Loubser & Jonathan Bellack & Roberto Ruju & Barbara B. Piermont & Thomas Jacques & George Levitte ·Google ·4 JAN 2017
The metric you pick isn't just how you measure success — it's the strategy itself.
Sam Bankman-Fried & Ryan Pinder & Daniel Friedberg ·FTX Trading Ltd. ·10 NOV 2022
When you can't save everyone, be honest about who you're choosing to save first — and expect the rest to notice.
Amy Hood ·Microsoft ·26 JUN 2023
When your platform is losing relevance, don't defend it — buy the assets that live on the platforms that are winning.
Elon Musk & Ilya Sutskever ·OpenAI ·13 SEP 2017
Control isn't a feeling — it's a seat count, and smart founders draw the arithmetic before the fight, not during it.
Michael Rapino & David Marcus & Tara Traub & Mark Yovich & Michael Wichser ·Live Nation Entertainment / Ticketmaster ·22 AUG 2022
The moment a client's manager whispers 'double dipping,' you have minutes to build a clear answer — or you have a narrative crisis.
Jim Giles & Eisar Lipkovitz & Jonathan Bellack & Payam Shodjai & Chris LaSala ·Google ·4 NOV 2017
When your product bundles a commodity with something rare, price the commodity like a utility and hide your margin inside what only you can offer.
Jim Giles & Eisar Lipkovitz & Jonathan Bellack & Payam Shodjai & Chris LaSala ·Google LLC ·4 NOV 2017
If the market is racing your margin to zero, either bundle your way out of the fight or pick which piece you're willing to give away first.
Ruth Porat & Jamie Rosenberg ·Google ·21 JUL 2017
The real deal isn't the revenue share — it's what you have to give up to earn it.
Neal Mohan & David Rosenblatt & Marc Schraer & Sean Downey & Andrew Rutledge & Ruth Kirschner ·Google ·13 FEB 2009
When a rival slashes prices out of desperation, the answer isn't matching them — it's reminding your customers what game you're actually playing.
Eugene W. Landy ·UMH Properties, Inc. ·13 MAR 2008
The best time to be bullish on a market is right after everyone else has abandoned it.
Michal D. Cann & John L. (Jack) Wagner ·WASHINGTON BANKING CO ·21 AUG 2008
Knowing when to kill a deal is as valuable as knowing when to sign one.
Steven E. Fass & David T. Foy ·White Mountains Insurance Group Ltd ·10 APR 2006
Risk models are tools, not oracles — and the leaders who survive bad years are the ones who say so out loud.
Jack Dorsey & Sarah Friar ·Square, Inc. ·3 AUG 2016
The real moat isn't the hardware — it's every product a seller adopts after the first swipe.
Square Investor Relations Team ·Square, Inc. ·1 NOV 2016
The strongest growth signal in this letter isn't revenue — it's that larger sellers are choosing Square on product merit, not discounts.
Jack Dorsey ·Block, Inc. ·2 NOV 2023
When the company is growing faster than the business, the fix is a hard ceiling, not a pep talk.
Roku Management ·Roku ·21 FEB 2019
The platform that wins the eyeballs first will collect the ad dollars second — Roku is betting the sequence matters.
DoorDash Leadership ·DoorDash ·15 FEB 2024
Growth and efficiency aren't opposites — they're phases. Knowing which phase you're in is the job.
Tony Xu ·DoorDash ·11 FEB 2025
Profit and growth aren't opposites when capital follows evidence, not enthusiasm.
Richard McCathron ·Hippo Holdings Inc. ·10 NOV 2022
The best risk management happens months before the storm, not during it.
Richard McCathron ·Hippo Holdings Inc. ·6 MAR 2024
Before going on offense, fix the math on the losses you can actually control.
Richard McCathron ·Hippo Holdings Inc. ·2 MAY 2024
Deliberately slowing growth in the short term can be the fastest way to reach sustainable growth — if you're cutting the right risks, not the right customers.
Richard McCathron ·Hippo Holdings Inc. ·8 AUG 2024
The best time to prove your risk controls work is when the whole industry is bleeding — and you're not.
Richard McCathron ·Hippo Holdings Inc. ·7 MAY 2025
The best time to expand is right after you've finished cutting — not before.
Richard McCathron ·Hippo Holdings Inc. ·6 AUG 2025
The smartest asset sale isn't an exit — it's a trade: cash plus a bigger channel.
Matt Fischer ·Apple Inc. ·21 AUG 2018
The moment your partners consistently refuse your terms, you have two choices: lose them or adapt — and waiting too long to decide is its own decision.
Netflix Investor Relations ·Netflix ·21 APR 2014
When you face bigger rivals on every side, define the game by the two things only you can do well.
Reed Hastings & Netflix Leadership ·Netflix ·16 JUL 2020
Formalizing power someone already has is cheaper than losing them — and clearer for everyone watching.
Ted Sarandos & Greg Peters & Spence Neumann & Spencer Wang ·Netflix ·18 OCT 2023
If you want to justify a massive cost center, show how it drives margin expansion at the same time — then the spending becomes the strategy.
Andy Jassy ·Amazon ·11 APR 2024
When your core business gets cheaper to run, every new bet you place gets cheaper to fund.
Andy Jassy ·Amazon ·10 APR 2025
Most companies optimize inside the room they're standing in; the best ones keep asking why the door is locked.
Warren Buffett ·Berkshire Hathaway ·1 MAR 2010
Liquidity is a strategic weapon disguised as a boring balance sheet item — its real return shows up only when everyone else runs out.
Kate Plikus ·Microsoft ·2 OCT 2018
In ad markets, scale isn't just an advantage — it's the price of admission to compete at all.
Jeff Shardell ·Google ·4 JUN 2007
When a partner asks for the same price on a worse deal, the right answer starts with naming what you're actually buying.
Michael Murphy ·Google ·17 MAR 2020
Sometimes the smartest negotiation move is paying your partners less — if you can redirect that money to win the customers who matter most.
Prabhakar Raghavan ·Google ·1 JAN 2019
If your pricing model only has two players in it, you've already mispriced — the third player is the door your customer can walk through.
Jonathan Bellack ·Google ·10 MAY 2018
Every dollar that flows through someone else's exchange is a dollar where you don't set the toll — and Bellack's math shows just how big that toll can be.