The best advice Brex founder and co-CEO Henrique Dubugras ever received came from Snap CEO Evan Spiegel: The best CEOs, Spiegel told him, are “extremely authentic to themselves ... If you try to emulate being Elon Musk and you’re not like that, you’re just gonna fail.” This wisdom has empowered Dubugras and his co-founder, Pedro Franceschi, to focus on the places where they can be most effective at Brex, and to be more authentic with their coworkers.

In this episode, Henrique and Joubin discuss coaches vs. therapy, mutual crushes, “hacker famous,” big egos, why missions are overrated, dropping out of college, CEO’s identities, the “Silicon Valley mold,” trojan-horsing Max Levchin, pivoting after two years, going to the ground, compensation and hiring myths, core customers, fixing expense report policies, and joining the Expedia board.

In this episode, we cover:

* Growing up in Brazil and Henrique’s relationship with his mom (01:07)
* The first company he sold, Pagar.me, and his co-founder Pedro Franceschi (07:11)
* Becoming “successful” and why it’s fine to have a different types of motivation (10:35)
* ADHD, dueling superpowers, and focusing on the right things (15:56)
* Being an authentic CEO and not reading books (19:51)
* The radical changes Brex has experienced in the past three years (24:40)
* Brex’s new spend management product and landing initial customers (30:30)
* The messages sent by how Brex structures its employee compensation (34:07)
* How Henrique and Pedro recruited top talent when they were just getting started (38:57)
* Pivoting a $12 billion company: “We can’t do all these things” (43:33)
* The challenges of becoming more of an enterprise company than a Fintech one (50:34)

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