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  • 🚀 Contagious Leadership: 10 must-reads and listens for May

🚀 Contagious Leadership: 10 must-reads and listens for May

May 2026

Hey, it’s Aaron. I’m in Addis Ababa, Ethiopia for a few days of non-profit work. There’s an incredible young filmmaker out of NYU Film School named Josh Leong who I’m very excited to be supporting in his quest to make a movie called LOST BOYS.

It’s a beautifully-written film telling the story of a boy who grew up in the Ethiopian orphanage that my oldest son grew up in. The goal is to really wake people up and get them engaged in solving the global orphan crisis. I’m deeply honored to get to support Josh in helping his vision come to life.

Also — if you’d have told me I’d be Executive Producer of a film, I’d probably have peed my pants laughing at you. But life is strange, and here I am.

This month, I’ve got a mega collection of 10 incredible reads and listens that I think you’ll love.

Once again, I DEEPLY appreciate all the feedback you’ve been giving us on MeetingOS! We’re about to launch a crazy new feature that SAVED my bacon the other day. It’s called Daily Brief. If you want to try it out for free, just reply back and let me know.

Welcome again to all the new folks! I love hearing from you, so send back questions, thoughts, ideas, or just a hello any time by hitting reply.

NEXT MONTH — something very new and big with the monthly email. I really think you’ll like it. Looking forward to sharing it with you.

Remember, great leadership is contagious. Thanks for being here.

Great Reads / Listens of the Month

It was an exceptional month of content. You are not going to want to miss these!

The Algorithm: The Hypergrowth Formula that Transformed Tesla, Lululemon, General Motors and SpaceX by Jon McNeill. One of my mentors recommended this and it did NOT disappoint. I read it in two sittings. Strong writing in story telling mode with real-life examples — no abstract theories here. If you want to think more deeply about how to apply Elon’s algorithm to what you’re building, read this book.

Apple in China: The Capture of the World's Greatest Company by Patrick McGee. This book is absolutely phenomenal in explaining how Apple went from building factories in the United States to becoming absolutely interwoven and utterly dependent on the Chinese Communist Party for its business to succeed. There are no solutions here, just an indictment and awareness of a huge problem for the western world that we really need to solve.

The two leading AI companies, OpenAI and Anthropic, are getting close to going public. Naturally, we have dueling CFO profiles out in public. They are both fascinating because AI hyperscaling is nearly as much a financing challenge as it is a technical one.

OpenAI Wants to Go Public. First Sarah Friar Needs to Get It to Grow Up. The executive who edited Sam Altman’s slide from $1.4 trillion in compute spend to a mere $600 billion gets her moment in the sun.

Friar cuts an imposing figure when she walks into any room. She is known for her strategic acumen and comfort in the corporate norms of Wall Street, including a fondness for scheduled meetings and slide decks that ensure nothing is left to chance. Altman, by contrast, likes to come up with ideas on the fly, and is known to duck out of a room almost as soon as he enters it.

Banks have told both Anthropic and OpenAI that whoever makes it to market first will get to define the new industry. If Anthropic succeeds in pulling off a mega-IPO, it could suck the wind out of OpenAI. There are large pools of cash eager to back new AI companies, and the first mover will get first dibs.

WSJ

Anthropic’s CFO Wields Power Behind the Scenes. CEO Dario Amodei has noted that accurately estimating the massive computing needs the company will need years into the future will comprise the difference between success and bankruptcy. A lot of the responsibility for getting that calculation right lies with Rao.

When Rao joined in March 2024, he inherited a business valued at around $15 billion and generating in the low hundreds of millions in annualized revenue. In some ways, though, it was still run like a research lab.

Anthropic’s board meetings mostly focused on tech, policy and AI safety. Rao introduced a section to look more explicitly at the company’s business and financial performance, including enterprise software metrics and key leading indicators of growth, said one of the people.

To get up to speed, Rao immediately dug into the company’s gross margins and evaluated how to better manage compute for running and training Anthropic’s models. The changes he made had a significant impact. Anthropic jumped from 94% negative gross margins in 2024 to 40% positive gross margins the next year.

The Information

How Nadella and Altman Averted a Legal War Over AWS. For years, executives at Microsoft have become accustomed to tussling with OpenAI over the terms of the companies’ complicated business partnership, which gave Microsoft exclusive rights to sell OpenAI’s technology to cloud customers. Then two months ago, the ChatGPT maker announced a surprise deal to sell its AI to businesses through Amazon, a Microsoft archrival. While OpenAI thought its contract with Microsoft allowed for the Amazon arrangement, Microsoft disagreed.

Several senior Microsoft executives were unsure how to interpret the OpenAI-AWS announcement and voiced concerns that it would run afoul of the existing agreement with Microsoft, according to the person familiar with the company’s thinking.

Microsoft said publicly several weeks later that it was “confident that OpenAI understands and respects the importance of living up to [its] legal obligation.”

The brewing fight led to a series of meetings between Altman and Nadella that aimed to resolve the potential legal concerns.

One factor that aided the talks was Microsoft’s diminishing reliance on OpenAI’s technology, which it gets for free, to power its products. Microsoft has become one of Anthropic’s biggest customers, by using Anthropic to power features in Microsoft’s Copilot AI products. Copilot automates tasks like scheduling Teams meetings or creating financial models in Excel. Anthropic models in some instances worked better than OpenAI’s.

The Information

Should AI and Christianity Mix? Pat Gelsinger and Gloo Holdings Sure Think So. Pat is one of the smartest technical minds on earth. Many would argue his only fault as Intel’s CEO was not being aggressive enough about cost-cutting and layoffs, and he laid the groundwork that now has Intel stock up 5x from its recent lows. Now he’s tackling how to make sure AI centers on human flourishing. It’s a fascinating story.

Gelsinger’s public embrace of his new role at Gloo coincides with a broader religious resurgence in Silicon Valley. For decades, as he rose through the ranks at Intel and then the software giant VMware, Gelsinger was one of few openly Christian executives in Silicon Valley and would regularly post Bible verses on X. He seemed like an oddity: At the time, technology and religion were seen as unmixable forces. But in recent years, that perception has softened, with a growing number of the tech elite publicly embracing their faith.

With Gelsinger and Scott Beck, the company’s cofounder and CEO, at the helm, Gloo takes a maximalist approach to melding AI and Christianity together. More broadly, though, the religion’s faithful remain divided over how to approach AI—a tension reflected in Gloo’s own data. A February study by Barna Group, a research firm owned by Gloo, found that under a third of U.S. adults trust spiritual guidance from AI the way they would from a pastor.

The Information

Snapchat CEO Evan Spiegel: Distribution is the Moat. One of the few people in the world who has scaled a lasting consumer social product talks with Lenny about how he’s running Snapchat differently in an era where software itself is no longer a moat.

Why Elon Outcompetes Everyone. Eric Jorgenson, the author of “The Book of Elon,” goes deep on what Elon Musk does differently. I’m not particularly interested in replicating 120-hour weeks and sleeping on the factory floor, but I’m always intrigued by many of the other factors of how Elon focuses on one big lever and jumps up and down on it until it moves.

Brian Chesky and AI Founder Mode. I’ve admired the creator of AirBNB for a long time. He’s an artist and a designer first and foremost, and he recently put to words what many founders have felt: professional management can be the death knell for any company that should still be in an innovative phase. This interview by Patrick O’Shaugnesshy is a tour de force.

Having Kids by Paul Graham. PG essays are always fascinating reads. He’s an insightful writer and has a tendency to boil down a topic to the essential but complete things you need to consider to understand it. He departs from tech frameworks to a fascinating topic — having kids — and does a great job capturing the wonder of it all. I’m quite confident a large number of tech bros were scratching their heads in confusion on this one. 😂 

If you have a suggestion for a great read or listen of the month, hit reply and let me know — if I love it, I’ll give you credit in next month’s email!

If I can help, let me know.

That’s it for this month! As a reminder, I am coaching five CEOs or leadership teams. That’s all I have time for, but I’m having fun doing it, and it’s allowing me not to pay myself a lot from the new company while we are in the build phase. 😉 

I don’t think I could have been nearly as effective for my team without the help of a CEO coach. There’s just something about having someone who has walked that journey before as a “safe” sounding board who you can speak freely to.

At the moment, all of my coaching slots are full, but I always build a wait list because a few of my coaching engagements are for six to nine months at a time. If you want to discuss, click here to learn more about my approach, and hit reply if you’d like to talk about it.