Ross & Paladino met in 2005, when Ross returned to his high school alma mater to teach improv comedy workshops. An initial disdain turned into an inseparable partnership, as the two have been collaborating on laughs, life, and losing at love for the past decade.
Training Wheels initially began pre-production in the summer of 2015, when filmmaker Tyler Bertram was approached to take the visual reins of a Pilot episode. Over the course of the next couple years the trio partnered to film nine episode together, initially on a shoestring budget with the assistance of friends, and later through the generosity of fans through a crowdfunding effort in early 2017. 2018 saw the completion of a 30-min series finale with filmmaker Sean Parker.