[12] At age 12 he moved to Italy for a year to live with his grandfather, Ray DePaulo, who was the commercial minister at the U.S. embassy in Rome.

in history,[12] Ross moved to Baltimore to work at Booker T. Washington Middle School as a Teach for America AmeriCorps Member.

[30] In addition to concerns over countries increasing surveillance capabilities, Ross highlighted cases where businesses prioritized profit motives over the potential harms of technologies.

In 2011, he publicly "criticised the developers of internet surveillance equipment who were willing to sell their services to repressive regimes and allow governments to censor their citizens.”[31] In 2023, Ross was appointed to serve on the Maryland Economic Council by Governor Wes Moore.

[33][34] In February 2018 he announced as his running mate Julie Verratti, a craft brewery co-owner, former Senior Advisor at the Small Business Administration, and LGBT political activist.