If that weren't enough, and true to his family heritage being the son of the son of a boat captain, he's also been a fisherman and a bar owner-barkeep.
In his spare time, he confesses to playing the ponies during thoroughbred race season in Del Mar.
Why so productive?
“My dad told me, 'You only have so many sunrises to look at, where you going to spend 'em, and how are you going to spend 'em?' ” noted Theodore adding his dad's other piece of advice was, “Don't spin your wheels.”
Theodore's all tread when it comes to purpose and profession, and he leaves it all on the road.
A local product of Point Loma cluster schools including Cabrillo, Dana and Point Loma High, the 54-year-old Theodore graduated from Mesa College with a telecommunications major.
It served him well on his first post-collegiate job as a DJ in San Clemente.
But Theodore said he really got into radio as “a link to go into acting.” Which he's done. Though it took awhile.
Theodore just finished shooting the independent film “66 and Nowhere,” playing a Chicago mobster, Johnny Gaglione, which was released April 20 and will play at Ken Cinema in Kensington. He also will be busy filming that movie's sequel titled “The Gaglione Brothers Hit Hollywood,” which will begin filming in September of this year.
How Theodore was able to break into acting he attributes, in part, to his gift for doing accents which, during the interview with the Peninsula Beacon, switched, in turns, from Italian to French, to Asian Indian to a Texas drawl.
“We only had two days of shooting — we did everything in one take,” noted Theodore about “66 & Nowhere.” He added he has the lead for the sequel for the next gangster film that he characterized as “kind of a cousin of 'Get Shorty.' ”
Theodore said he loves Point Loma. But he's quick to tell you he misses the way it used to be pointing out, “I just want to make it look better?”
What's wrong with how it looks now?
“When I was growing up, all the homes had Spanish tiles on their roofs,” Theodore said. “I want to see the tiles back on the roofs. It was really beautiful. Now it's just a mish-mosh of everything.”
Theodore said when he was growing up the Village of Point Loma was really a village.
“We had the culture of family,” he said. “When I grew up it was a community. It's very detached now.”
A sales associate with Coldwell Banker based in their Shelter Island office, Theodore's also is a talk show host Saturdays and Sundays, from 8 to 10 a.m. on www.WSRadio.com, an Internet talk radio station.
Of his real estate expertise, “The Captain” commented, “I do just about everything on land. I try to make Point Loma look a lot better than surrounding areas.”
Of his radio work, he noted, “We do horse races, sports, real estate, investments — everything in life. We've had a ball with it.”
Like the Spanish tile roofs he'd like to see come back, Theodore added that same sentiment applies to his neighbors — and their descendants. He said it's sad to see older Point Lomans “passing away and their kids selling their properties and leaving town and never coming back.”
Theodore's a big fan of the recent redevelopment of Liberty Station noting, “They'e done more in the last two years than they did in the first 20. It's now a mecca and centerpiece of the area.”
Theodore added he believes strongly that the transformation of Liberty Station could well carry over into the rest of the community.
Looking ahead, Theodore intends to do exactly what he's been doing. That is, to “keep on going.”
“The day you stop moving, is the day you die,” he said. “You have to stay active.”