Long Strange Trip: CEO to CEO with Brian Halligan

This might be my favorite episode yet. Harvey’s Winston Weinberg is the canonical 2026 hypergrowth CEO. He takes us inside what it's really like to scale from zero to $190M run rate in just a few years. What stands out? His obsessive intensity and willingness to do uncomfortable things on a weekly basis. Winston shares how he cold-messaged thousands of lawyers to land his first customers, why he deliberately chose the hardest enterprise law firms as his first target customers, and how he thinks about hiring and org structure when everything breaks every four months. We also explore his unconventional background - he wasn't a developer, was new to the legal industry, and figured out sales from scratch. It's raw, honest, and incredibly practical for any founder navigating (or hoping to navigate) the chaos of hypergrowth.

Nikesh Arora is one of the most fascinating CEOs in tech. He didn’t come up through cybersecurity. He wasn’t a founder. And when he took over Palo Alto Networks, he openly admits he didn’t know what cybersecurity even meant. Today, under his leadership, Palo Alto has become one of the most successful platform companies in enterprise software. In this episode, Nikesh and I go deep on what it actually means to be a modern CEO. We talk about why founders should sometimes not listen to customers, why most M&A fails, and how Palo Alto built a multi-platform business by betting big (and early) on second acts. Nikesh breaks down his very unconventional approach to acquisitions, where founders run the acquiring company’s teams, not the other way around. He explains how platform companies are built one decisive product insight at a time, why “more features” is often a trap, and how great CEOs balance product obsession with go-to-market reality. We also spend time on leadership psychology: imposter syndrome, conviction, risk appetite, and how to project confidence while you’re still figuring things out, and how to remain physically and emotionally healthy while you do it. If you’re a founder, an operator, or an aspiring CEO thinking about second acts, platforms, or scaling yourself along with your company, this episode is a masterclass.

David Solomon, CEO of Goldman Sachs, says that no easy decisions reach the CEO’s desk - only “51/49” decisions. When I was leading HubSpot, I described the job as “choosing between two shitty options.” David discusses some of the tough calls he’s had to make in the CEO seat, including the difficult decision to wind down Goldman's consumer banking ambitions. His perspective coming from a 156-year old banking giant is a little different than the common Silicon Valley wisdom. Hear why he thinks experience is vastly underrated in Silicon Valley, why "smart enough" matters more than being the smartest person in the room, and why serendipity and timing play bigger roles in being a great CEO than people realize. David reflects on mentorship from Lloyd Blankfein and Hank Paulson and how he thinks apprenticeship culture will evolve with AI. There are some great, unexpected lessons here for founders who are scaling, confronting the messy reality of building enduring companies.

This one’s a treat: two AI-native CEOs building some of the world’s fastest-growing startups from outside of Silicon Valley.  Mati and Anton are navigating a world that’s moving 10X faster than it was when I was CEO of HubSpot. We dig into the realities of what it’s like scaling today: managing co-founder relationships when you're the only person you can complain to, delegating while staying in founder mode, building exec teams that blend experience with homegrown talent, and why lightweight planning rhythms are key when the AI tech stack changes every six months.  Both share tactical advice on managing chaos, from email triage systems to no-meeting days. They open up on Europe's advantages (hungry talent, less competition) and disadvantages (thinner executive bench), the 9-9-6 work culture debate, and why the next generation of European founders could finally build trillion-dollar companies. I thought these guys shared an honest look at what it really takes to lead through hypergrowth these days.

When Intuit was born, the world ran on DOS. Forty years later it is a $180 billion powerhouse serving millions of small businesses, and Sasan Goodarzi has led its evolution from boxed software to an AI-driven platform.  I’ve always admired Intuit’s track record with SMBs. I even had the chance to shadow one of its former CEOs, the legendary Brad Smith.In this episode, Sasan and I talk about what it takes to reinvent a legacy company, what he learned shadowing Amazon’s Andy Jassy, and why curiosity and grit matter more than raw talent. We talk about how to run a grown-up company without losing speed, from the mechanisms Intuit uses to challenge its own assumptions to the ways he stays close to customers through “follow-me-homes.” Sasan also shares his approach to winning in the SMB market, building effective channel partnerships, and creating second acts that actually succeed. He even tells the story of how Intuit was four years late to SaaS and still managed to come out stronger. Sasan shows that if you love the customer problem and keep disrupting yourself, you can stay young even after 40 years in business.