In January 2020, we announced that Visa was acquiring Plaid for over $5 billion, which was the result of months of negotiations and interest from Visa as an investor.

After the acquisition fell through, Plaid's business continued to grow significantly, leading to a valuation of $13 billion in a subsequent fundraising round.

I faced significant challenges raising $3.8 million to buy Starbucks, including competition from investors who wanted to take over the company without due diligence.

The decision to pursue an acquisition with Google was driven by the need for legal support, as YouTube was too small to effectively manage the impending copyright battles alone.

The internet has effectively removed intermediaries in many sectors, but the payments and finance sectors remain dominated by traditional systems like Visa, which extract significant fees.

With Zip2, we built incredible technology, but it never really got used as we intended. I wanted to go direct to consumers instead of being constrained by our customers, which led to the creation of X.com, which became PayPal.

When I became CEO, the dotcom bubble was bursting, antitrust issues dominated the company's culture, and we faced a significant accounting headache that affected profitability.

The emotional response from employees during the acquisition announcement was intense, as many had invested years into the company and had their identities tied to its success.

Negotiating the acquisition of DoubleClick by Google was about unlocking value for both sides, not just about price.