Frate Luca Pacioli da Borgo Sansepolcro, a polymath and true Renaissance Man, wrote a chapter of his De Divina Proportione treatise on how to construct Roman capitals with compass and ruler. Despite the 500 years that separate us, we’ll use Frate Pacioli’s work as a lens to revisit the perennial debate between technology and the liberal arts, the organic versus the synthetic, the hand versus the intellect. With no pretense of giving definitive answers, we will offer a few perspectives taken from our personal experience and from the history of letterforms, from Roman times to 20th century Italian type.