The PayPal Wars: Battles with Ebay, the Media, the Mafia, and the Rest of Planet Earth Paperback - 2023

Early in his career, Jackson was recruited by Peter Thiel to join the startup team at PayPal, where he oversaw product marketing and designed its revenue model. During Jackson's time at PayPal, the company grew to 25 million users, went public, and was acquired by eBay.

After leaving PayPal, Jackson started multiple venture-backed technology startups. His company CapLinked, whose transaction-management software was called the "go-to place for setting up and closing deals" by the Wall Street Journal. He also co-founded TransitNet, a software company that provides title verification for cryptocurrency. Additionally, Jackson founded World Ahead Media, which he grew to profitability and sold, and served on the boards of multiple organizations.

His book, The PayPal Wars, which chronicles the tumultuous origins of PayPal, won the Writers Notes Book Award and was hailed by Tom Peters as "the best description of business strategy unfolding in a world changing at warp speed."

A frequent commentator on technology and policy, Jackson has appeared on Bloomberg, CNN, Fox News, and MSNBC, and has been the keynote speaker at events hosted by the Cato Institute and Reason Foundation.

Jackson graduated with honors from Stanford University. He lives in Los Angeles with his wife Stacey and their two daughters.