Large companies rarely make cold acquisition offers. The typical path is a gradual process starting with a partnership or a small investment. This allows the acquirer to conduct due diligence from the inside, understand the startup's value, and build relationships before escalating to a full buyout.

Counter to the adage that "startups shouldn't buy startups," Cursor successfully uses M&A as a core recruiting strategy. They acquire small, talented teams working on complementary problems, viewing acquisitions as a way to onboard the best people who happen to already be working on their own companies.

Stripe's acquisitions of Bridge and Privy follow the Google playbook (e.g., YouTube, Android) rather than the Oracle model. The goal is not to absorb a mature product but to acquire a high-potential team and technology to build a new, strategic business pillar from an early stage.

The success of an AI roll-up hinges on effective technology implementation. Therefore, the primary filter for acquiring a company is not just its financials but whether its leadership and culture are genuinely eager to adopt AI and transform their operations. This cultural fit is non-negotiable.

Bryan Johnson reveals his strategy for Braintree was to first capture the merchant side of the payments market with top-tier clients like Uber and Airbnb. Once that was established, he acquired Venmo to instantly gain the consumer side, completing the two-sided marketplace without the immense cost of building it from scratch.

By building its own financial stack "straight to the metal" on MasterCard, bypassing third-party issuers, Brex gained a crucial advantage. This vertical integration provides the flexibility to launch in new countries with the "flip of a switch" and power complex embedded finance partnerships.

Large financial institutions, which once insisted on building all tech in-house (even email clients), have undergone a cultural shift. Humbling experiences and the clear ROI of AI have made them more open to adopting best-in-class external software, creating a huge market for B2B fintechs.

Brex organizes its AI efforts into three pillars: buying tools for internal efficiency (Corporate), building/buying to reduce operational costs (Operational), and creating AI products that become part of their customers' own AI strategies (Product).

When acquiring a business, don't rely on a single outcome like achieving a growth target. Instead, seek assets that offer multiple ways to win. Even if the primary goal is missed, the acquired data, technology, or talent could create significant value for other business units, providing built-in insurance for the deal.