Long Strange Trip: CEO to CEO with Brian Halligan

Jack Dorsey (Block CEO) and Roelof Botha (Sequoia partner and Block board member) join to discuss a bold claim they wrote about recently: the traditional corporate hierarchy isn't just inefficient — it's obsolete. Jack made one of the toughest calls in recent business history: cutting 40% of his workforce and rebuilding the company from the ground up around what he calls an AI "intelligence layer." We get into how that conversation went down, the math they used to land on a number, and why he's convinced that acting from a position of strength beats reacting from one of weakness.

Jack breaks down his vision for simplifying into just three roles, and what it means to replace a pyramid org chart with a circle — AI at the center, and people at the edge. Roelof, who helped think through the restructuring, shares his perspective on how AI-native startups are building differently, and what CEO qualities are timeless. 

I've eliminated org charts before. I know how hard this is. But Jack is doing something I never had the tools to pull off. If you're a founder wondering whether your hierarchy is working for you or against you, this one will make you uncomfortable in the best way.

Tom Hale didn't originally set out to be a CEO - then he put it on his bucket list to prove something to himself. Now he runs Oura, the Finnish health tech company behind the most talked-about wearable on the market - the Oura ring. In this conversation, we get into what the job actually feels like from the inside (spoiler: the kibble-to-champagne ratio is not what you think), and Tom shares some of the sharpest frameworks I've heard for scaling a company through the 200-to-2,000 employee gauntlet.

We dig into Oura's controversial pivot to a subscription model - the Reddit flames, the one moment Tom almost blinked, and why he's now calling it an unqualified success. He breaks down the asymmetry between work and headcount that causes politics to metastasize in growing companies, what he looks for in middle managers to keep bureaucracy from setting in, and how he thinks about staying close to customers as layers accumulate between you and them.

We also get into the Gucci partnership, what a Roman emperor has to do with it, and the unexpected retail insight that came out of it. And Tom shares why he sleeps soundly despite Apple being the 800-pound gorilla in wearables.

If you're a founder navigating the messy middle of company building, this one is worth your time.

Kaz Nejatian reveals how he left Shopify to pull off a highly unusual feat: refounding a struggling public company in just 16 days. From first attempting to take the company private and then becoming CEO with an unwavering commitment to prioritizing product, Kaz shares his unconventional playbook and approach to life.

We go deep on why most enduring companies are built on "first derivatives" of their core business and not the obvious thing everyone focuses on. Kaz explains why he reads the Bible every day, how overriding life's defaults requires going full force (not halfway), and why founder mode means taking responsibility for outcomes, not processes.

He breaks down the mechanics of the Opendoor turnaround, why he tethered his compensation to stock performance, and how he’s making the company AI-native. Essential listening for understanding true founder mode, or for anyone building something that matters.

A16z’s Ben Horowitz joins me for a raw, unfiltered conversation on what actually breaks founder CEOs, and what separates the great ones from the rest.

We unpack founder mode, where it works and where people are taking it too far. Ben shares why overly deferring to experienced executives creates politics and fiefdoms, but avoiding senior talent altogether is just as risky. Founder mode is not about micromanaging. It’s really about taking responsibility for outcomes and having the confidence to manage people who may have more experience than you.

Ben goes deep on “constructive confrontation” and why running away from the truth to preserve feelings is one of the most dangerous things you can do in a tech company. He explains why bad news has to travel fast, how decision debt paralyzes organizations, and why hesitation, not lack of intelligence, is what usually gets CEOs replaced.

We also dive deep into hiring, especially the VP of Sales role founders mess up more than any other. Ben breaks down why great sales leaders qualify you in the interview, why references matter more than charisma, and why selling a hard product builds a different kind of operator.

Along the way, we cover the psychology of being a first-time CEO, what Zuckerberg, Jensen, and Elon actually have in common, why culture is defined by behavior not values, and why feeling like you don’t know what you’re doing is more normal than most founders admit.

Bill Anderson runs Bayer, a 160-year-old pharmaceutical giant that had 100,000+ employees when Bill took the helm. In just two years after becoming CEO, he flattened 11 layers of management, expanded managers' direct reports from 6 to 90, and eliminated annual budgeting in favor of 90-day cycles.

Bill offers up some gems on how to scale without becoming bureaucratic, explains why "professional managers" kill startups, why peer feedback beats manager reviews, and why bureaucracy isn’t a virus that infects healthy companies but rather something that grows from within the heart of your org chart.

If you're scaling from 100 to 1,000 employees and want to avoid the death spiral that slows most growing companies, this is essential listening. Bill's created a playbook for organizational transformation that challenges what you think you know about building companies.