Troutwine earned a perfect score on the Stanford Achievement Test, and graduated high school at the age of sixteen.

[1] While at Yale, Troutwine and Markus Moberg, launched Veritas Prep, a GMAT preparation and MBA admissions consulting company.

[13] Troutwine is an investor and member of the board of directors of the crowdfunding and film distribution platform, Seed&Spark.

[14] Troutwine is also an advisor to SoloPro, a real estate startup venture founded by former US Army Special Forces officer and Duke University professor Tommy Sowers.

[20] In 2014, Troutwine's documentary, Print the Legend, won a special jury award at the 2014 SXSW Film Festival.