Pierce had small roles in Little Big League (1994), Ripper Man (1995), Problem Child 3: Junior in Love (1995), Three Wishes (1995), Earth Minus Zero (1996), and The Ride (1997).

[6] Pierce retired from acting at 16 and joined as a minor partner with Marc Collins-Rector and Chad Schackley in establishing Digital Entertainment Network (DEN), which raised $88 million in venture capital.

[8] DEN was one of a crop of dot-com startups that focused on the creation and delivery of original video content online in the late 1990s[9] before the wide adoption of broadband internet access.

[16] Pierce founded ZAM, a network of websites oriented around massively multiplayer online role-playing games (MMORPG), such as World of Warcraft, Star Wars: The Old Republic, Rift, EverQuest, etc., in 2003.

[19] Pierce joined other Southern California angel investors, including MP3.com's Michael Robertson, SOA Software's Eric Pulier and William Quigley, and Jim Armstrong of Clearstone Ventures.

[22] In late April 2012, Titan Gaming announced that it would be rebranded as Playsino to embark in a complete makeover, with Pierce as the new CEO and $1.5 million of new funding.

[23] IMI exchange was subsequently acquired by Moda Inc.[24] Pierce has been a guest speaker at the Milken Global Conference,[25] Singularity University,[26] and the California Institute of Technology.

[30] In March 2014, Pierce and a group of investors filed an offer to purchase the assets of Mt Gox using a Cypriot entity called Sunlot Holdings Ltd.

[36] In a February 2018 issue of Forbes magazine, Pierce was named in the "top 20 wealthiest people in crypto" with an estimated net worth between $700 million and $1.1 billion.

[39] In 2020, a court permitted the Attorney General of New York to pursue a claim that Bitfinex, an affiliated exchange, did not disclose the loss of commingled funds.

[30] By March 2018, Pierce's role at Block.one had changed to chief strategy officer and he resigned from the company that month to pursue community building.

[40] Pierce led an international delegation to El Salvador in June 2021, to advise the Salvadorian government on their formal adoption of Bitcoin as their national currency.

[46][47] Pierce is the vice chair and spokesperson of the U.S. Marines Toys for Tots Foundation of New York, Long Island, and Puerto Rico.

[64] Stating that the war on drugs has failed, he advocates ending federal enforcement and to pardon and expunge all non-violent cannabis crimes.

[66] The Free & Equal Elections Foundation hosted the Second Open Presidential Debate on October 8, 2020, in Denver, Colorado, with participation limited to candidates on the ballot in at least eight states.

[72] In November 2021, Pierce filed a statement of organization with the FEC and later confirmed he was considering a 2022 run for the United States Senate to replace retiring Vermont senator Patrick Leahy[73] After news reports indicated Pierce could lose his federal income tax-free status as a Puerto Rico resident by running in Vermont,[74] he did not file to qualify for the ballot.

""[77] In 2017, he relocated to Puerto Rico along with other traders, becoming the leader of a group focused on creating a cryptocurrency based local economy on the island, capitalizing on the aftermath of Hurricane Maria.