Long Strange Trip: CEO to CEO with Brian Halligan

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.

I didn’t think Parker Conrad would get up off the mat when he got ousted from his previous startup, Zenefits. No one in Silicon Valley did. Instead, Parker let his rage propel him into an all-consuming mission to prove the haters wrong and build Rippling, a $17 billion juggernaut that blows his prior success out of the water. Parker has advice for founders: from productively harnessing the chip on your shoulder, to maintaining fast operational velocity to why you need founder-minded people on your team instead of manager-minded people—even among your managers. And yes, he spills the dirt on Deel.  Parker is one of the new greats who is tearing up the old CEO rulebook and writing his own. - Brian Halligan, Sequoia Capital

Brian Halligan–Sequoia partner and co-founder and longtime CEO of HubSpot—is on a quest to uncover the new rules of CEO-ing from the best CEOs in the world, from hypergrowth AI-native startups like Lovable and ElevenLabs to scaleup juggernauts like Robinhood and Rippling, to 150-year-old behemoths like Goldman Sachs.Watch at:  https://www.youtube.com/sequoiacapital