

Long Strange Trip: CEO to CEO with Brian Halligan
The CEO rulebook is getting rewritten. Brian Halligan, Sequoia partner and co-founder and longtime CEO of HubSpot, sits down with some of the CEOs who are defining the new one—from hypergrowth AI-native startups to 150-year-old behemoths. Whether you’re an early-stage founder or a scale-up CEO, Brian will be digging for advice you can use on the long strange trip of your own CEO journey.
Episodes


Databricks’ Ali Ghodsi Never Wanted to Be CEO. Now He’s Among the Best
Scaling a technology company requires relentless focus on a single, primary bottleneck, such as shifting from product-led growth to enterprise sales. Effective leadership demands extreme pickiness in executive hiring, utilizing rigorous reference checks to minimize false positives. Strategic pivots, like the transition...

The Philosopher CEO | Clay Co-Founder Kareem Amin

Kalshi’s Tarek Mansour vs. the Federal Government

David Senra: Mute the World and Build Your Own

Notion’s Ivan Zhao: The Refounder
The transformation of SaaS companies into AI-native organizations requires a "refounding" mindset and the adoption of agile, "jazz band" operational structures. Moving away from rigid, hierarchical "marching band" models, companies must embrace a technology-first approach where AI facilitates information flow and decis...

Surviving Twitter's Growing Pains: Ex-CEO Dick Costolo
Scaling a hypergrowth organization requires shifting from consensus-based decision-making to a "bias to yes" culture, where decisions are pushed down the stack to designated responsible individuals. Maintaining velocity demands solving operational bottlenecks through direct control rather than layering on restrictive p...

What Founders Can Learn About Excellence From MIT President Sally Kornbluth
Sally Kornbluth, President of MIT and a distinguished biologist, navigates the complexities of leading a premier global institution through high-stakes crises and the evolving landscape of higher education. Maintaining institutional excellence requires a relentless commitment to meritocracy, exemplified by MIT’s refusa...

Jack Dorsey: Every Company Can Now Be a Mini-AGI
Organizational structures must evolve from traditional, lossy hierarchies toward "intelligence-based" models that leverage AI to facilitate real-time information flow and decision-making. By treating a company as a "mini-AGI," leaders can replace rigid management layers with a system where customer data serves as the p...

Oura’s Tom Hale: What People Don’t Tell You About Being CEO
Scaling a company through the "messy middle" of 200 to 2,000 employees requires maintaining a non-hierarchical culture while resisting the influx of bureaucratic "bozos." Oura CEO Tom Hale emphasizes that leadership success hinges on high-level visibility, direct engagement with employees, and a relentless focus on cus...

The Most Founder Mode CEO Working Today Isn’t the Founder: Opendoor’s Kaz Nejatian
"Founder mode" demands that CEOs take absolute responsibility for outcomes rather than merely managing processes, often requiring a "re-founding" approach to reverse corporate stagnation. This leadership philosophy prioritizes truth and long-term value creation over short-term metrics or conventional management structu...

Ben Horowitz On What Makes a Great Founder
Great tech companies rely on founder-CEOs who prioritize bluntness and constructive confrontation to ensure bad news travels fast. Effective leadership requires the confidence to make decisive choices, avoiding the common traps of over-deferring to subordinates or hesitating during uncertain times. Hiring, particularly...

Bayer’s Bill Anderson: Turning a 168 Year-Old Tanker Like a Speedboat
Large-scale organizational bureaucracy stems from internal design choices, such as excessive management layers and rigid functional silos, rather than external infection. To maintain agility while scaling, companies must shift from command-and-control structures to models that empower employees to own the business. Bay...

The Wartime CEO: Vlad Tenev of Robinhood

Harvey CEO Winston Weinberg: Why You Should Reinvent Yourself Every 4 Months

Palo Alto Networks’ Nikesh Arora: Why Context Switching is a CEO’s Most Critical Superpower

Goldman Sachs CEO David Solomon: What Startup Founders Get Wrong About the CEO Job
David Solomon, CEO of Goldman Sachs, discusses leadership, culture, and decision-making in established companies. Solomon emphasizes the importance of experience and judgment, especially during challenging times, and shares his approach to balancing the needs of clients, shareholders, and employees. He recounts Goldman...

Scaling AI Rocketships: ElevenLabs’ Mati Staniszewski & Lovable’s Anton Osika

Intuit CEO Sasan Goodarzi’s Grown-Up CEO Playbook

Parker Conrad’s Revenge Fantasy
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