Penna was a longtime employee and representative of the MacGregor Golf Company. After years of working for MacGregor, Penna started his own company and manufactured his own golf clubs. A stretch of road in Jupiter, Florida, where his company was located is named after him. Penna used the spelling of his name as an attention-getter, and was known for having a taste for fine clothing. Penna displayed an ability for concentrated problem-solving in improving golf club performance which led to his success as an equipment representative, a golf pro, and also as the producer of his own line of golf clubs.