Sequoia CEO coach: Why it’s never been easier to start a company, and never been harder to scale one | Brian Halligan (co-founder, HubSpot)

**Brian Halligan** (0:00)
The thing about being a founder, CEO, is there's no one there to rescue you. Your parents aren't going to rescue you. Your VC is not going to rescue you. That kind of hits you when you hit your first crisis.

**Lenny Rachitsky** (0:08)
Starting a company has never been easier. Scaling one into a durable, high-impact organization has never been harder.

**Brian Halligan** (0:13)
The number of companies formed is going to mushroom over the next 10 years relative to the last 10 years. It's just going to be hard to stand out and really accelerate.

**Lenny Rachitsky** (0:20)
What's most different about what it was like to be a CEO maybe 10, 20 years ago versus today?

**Brian Halligan** (0:25)
There's a massive tax and optionality when you can move this fast and try a lot of things. It puts pressure on the CEOs to be faster and better decision-makers.

**Lenny Rachitsky** (0:35)
A lot of people in the world want to be founders. They want to be CEOs.

**Brian Halligan** (0:38)
I don't think anyone can do it. People talk about 996 It's way more than that. Founders are seven days a week. They're always on. I text on the nights. It's full contact.

**Lenny Rachitsky** (0:46)
Do you feel like there are specific profiles or traits to be successful?

**Brian Halligan** (0:50)
I look for four things. I call it my luck algorithm.

**Lenny Rachitsky** (0:56)
Today, my guest is Brian Halligan, co-founder and longtime CEO of HubSpot. I asked Brian to come on this podcast because he is, more than anyone I have met, a student of the job of a CEO. After leaving HubSpot last year, he became the in-house CEO coach at Sequoia where he brings together dozens of top CEOs to learn from each other. He does one-on-one coaching with some of the world's top CEOs. He also hosts a popular podcast called Long Strange Trip where he interviews some of the world's most successful CEOs. In this conversation, we unpack what it takes to be a successful CEO in today's era. Let's get into it after a short word from our wonderful sponsors. Applications break in all kinds of ways. Crashes, slowdowns, regressions, and the stuff that you only see once real users show up. Sentry catches it all. See what happened, where and why. Down to the commit that introduced the error, the developer who shipped it, and the exact line of code all in one connected view. I've definitely tried the five tabs and slack thread approach to debugging. This is better. Sentry shows you how the request moved, what ran, what slowed down, and what users saw. Seer, Sentry's AI debugging agent, takes it from there. It uses all of that Sentry context to tell you the root cause, suggest a fix, and even opens a PR for you. It also reviews your PRs and flags any breaking changes with fixes ready to go. Try Sentry and Seer for free at sentry.io/lenny and use code Lenny for $100 in Sentry credits. That's S-E-N-T-R-Y dot I-O slash Lenny. This episode is brought to you by Datadog, now home to Eppo, the leading experimentation and feature flagging platform. Product managers at the world's best companies use Datadog, the same platform their engineers rely on every day to connect product insights to product issues like bugs, UX friction and business impact. It starts with product analytics, where PMs can watch replays, review funnels, dive into retention and explore their growth metrics. Where other tools stop, Datadog goes even further. It helps you actually diagnose the impact of funnel drop-offs and bugs and UX friction. Once you know where to focus, experiments prove what works. I saw this first hand when I was at Airbnb, where our experimentation platform was critical for analyzing what worked and where things went wrong. And the same team that built experimentation at Airbnb built Eppo. Datadog then lets you go beyond the numbers with session replay. Watch exactly how users interact with heat maps and scroll maps to truly understand their behavior. And all of this is powered by feature flags that are tied to real-time data, so that you can roll out safely, target precisely, and learn continuously. Datadog is more than engineering metrics. It's where great product teams learn faster, pick smarter, and ship with confidence. Request a demo at datadoghq.com/lenny.
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Brian, thank you so much for being here. Welcome to the podcast.

**Brian Halligan** (4:02)
Thanks for having me, Lenny.

**Lenny Rachitsky** (4:04)
It's my pleasure. I want to start with something that I've heard your board members, the way they described you, is someone with a perpetual state of constructive dissatisfaction. Do you think this is a core foundational kind of trait of successful CEOs, successful leaders?