Waymo and Whimsy

This chapter humorously delves into the expansion of Waymo, the autonomous vehicle company, alongside discussions about its name and user experiences. The speakers speculate on the company's growth, legal challenges, and transition into various urban landscapes, while also engaging in a playful debate about a potential sequel to 'Happy Gilmore.'

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Art Levy, Chief Business Officer at Brex, the $12.3 billion modern finance behemoth, breaks down why we’re seeing a Golden Age of M&A, with mega-acquisitions, reverse acqui-hires, and aggressive consolidation across the AI landscape. From Meta’s $14B 49% stake in Scale AI, to Google’s $32B Wiz deal, & Stripe’s aggressive crypto rail strategy, Art offers a sharp view into the strategies behind the biggest moves in tech & finance.

We go deep on:

• The rise of “tuck-in” M&A (Scale AI) + strategic AI consolidation

• Best & worst practices for M&A

• Brex’s growth: 80% YoY enterprise revenue growth, 140% NRR, $100B+ in TPV run rate

• Their structural advantage vs. Ramp, Amex, & legacy banks

• The rise of crypto rails (Stripe’s acq of Bridge & Privy)

• Raising $1.5B & the road to IPO

Brex has evolved far beyond its startup roots, now powering financial operations for over 200 public companies, including leading global players like Arm, Anthropic, eToro, Neuralink, Scale AI, Wiz, etc. Plus 1 in 3 venture-backed startups in the U.S. use Brex. With multiple $100M+ revenue lines, Brex combines a globally distributed payments platform with spend management software, banking infrastructure, and AI-powered automation. The company is redefining what it means to be mission-critical infrastructure for modern CFOs — with durable revenue streams, strong retention, and a clear path to IPO.

Brex Funding Stats:

• Last valuation: $12.3B, primary round done in late 2021

• Investors: YC, DST Global, Greenoaks, Tiger Global, Ribbit, TCV, Kleiner Perkins, IVP, Lone Pine, GIC, Baillie Gifford, Madrone Capital Partners

• Total funding: $1.5B; did a tender offer in early 2022 for $250M at same $12.3B valuation.

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Chapters:

(01:13) Massive AI Consolidation

(04:41) Art Levy's Journey to CBO at Brex

(08:28) Brex's $12.3B Evolution & Path to IPO

(14:18) Current State of M&A (Meta, Stripe, OpenAI)

(24:00) Meta's Strategic Moves in AI

(37:32) Best & Worst Practices for M&A

(50:00) 3 Types of M&A

(52:22) Brex's M&A & Partnership Approach

(53:35) Brex's Modular Product Strategy