More than luck — with Kevin Tostado

Step into any insurance professional’s office and you’re likely to see a display of the awards they have received over the course of their career. Sales awards, industry honors, certificates from their professional associations — you can find them hanging on the walls or arranged on a shelf.

But not many professionals in the insurance business can boast of winning an Emmy Award. Kevin Tostado is perhaps the only one.

Tostado is a Financial Adviser in San Diego, Calif. offering investment advisory services through Eagle Strategies LLC, a Registered Investment Adviser and a Registered Representative offering securities through NYLIFE Securities LLC. Eagle Strategies and NYLIFE Securities are New York Life Companies. But he also is the owner of Tostie Productions, an Emmy Award-winning, high-definition production company that he founded 21 years ago. Tostie Productions’ mission is to make innovative films and videos that inspire, provoke and entertain their audience.

Tostie Productions produced an Emmy award-winning documentary, “Under the Boardwalk: The MONOPOLY Story,” which was a bestselling title on Amazon and iTunes and was at one point the No. 2 most-streamed title for all of Netflix in the U.S. The television version of “Under the Boardwalk” received four regional Emmy Awards, including Outstanding Achievement in Documentary, Directing, Editing, and Musical Composition/Arrangement. Tostie Productions also helped produce the feature comedy “Eternity: The Movie,” a film about the rise and fall of a fictitious 1980s rhythm and blues band.

The filmmaking bug bites

Tostado said he always had an aptitude for math and science, and that led him to study electrical engineering at Olin College of Engineering in Needham, Mass. But the filmmaking bug bit him while he was in college, and he decided to make that his career. It was a natural next step for someone who enjoyed acting in plays during summer camp and studying photography in high school.

“As I was graduating from high school, I realized that film is the intersection of drama and photography,” he said. 

While he was a student at Olin, he enjoyed filming various aspects of campus life, editing the film and compiling DVDs to sell at cost. 

“I wanted to document what was happening around campus,” he said. “In my junior year, a friend and I decided that the video the school was showing prospective students when they tour the campus was designed for prospective investors or donors to the school. It wasn’t done from a student’s perspective. So we thought we would take all the footage we had been shooting and edit it into a 15-minute piece about student life at our college.”

He said the college admissions department staff liked the finished product and showed it to all incoming students for the next few years.

“My friend and I had such a good experience doing this that we thought we should make a feature film next,” he said. “So the summer before our senior year, we wrote a script together and shot it over the weekends during the fall and winter with college students as the cast and crew. We made the entire feature film for $500. It was a coming-of-age story, loosely inspired by some events that happened to the two of us and one other friend.”

The film was submitted to  several film festivals and eventually was shown at a small festival in California, where it won awards for best feature and best cinematography. 

Tostado said the experience inspired him to set aside the idea of becoming an electrical engineer and focus on filmmaking instead.

“I figured I had my engineering degree to fall back on if things didn’t work out,” he said.

Taking a chance on Monopoly

Tostado began working for a San Diego TV station that was producing telenovelas, serial dramas that are popular with Hispanic viewers. From there, he started producing TV commercials and music videos, and eventually he decided he was ready to create another feature film. He chose to focus on the game of Monopoly — specifically, the U.S. and world Monopoly championships that occur every few years.

“No one had explored this topic in depth before,” he said. “I knew there are a lot of Scrabble competitions out there, but I didn’t realize there was a competition for Monopoly. I didn’t realize there was a competition where you could win money.”

Before creating the documentary on Monopoly, Tostado said, he thought the popular board game is more a game of chance than a game of strategy. But he soon learned there was more to Monopoly than a lucky roll of the dice.

“Monopoly is a game that involves your interpersonal skills,” he said. “Luck is always a component of the game, and you will have some games where the dice don’t go your way. But even if you land on only a few properties and they’re not what you’re looking for, if you’re a good trader — if you’re able to negotiate with other people around the table, pick someone else and make them the common enemy — you make some trades in your favor and give yourself an advantage that you might not have had otherwise.”

Tostado said the people most likely to win Monopoly at the competition level are the ones with the best communication skills.

“If you are the type of person who keeps to yourself, you won’t win that many games. You’ll win based on luck, so maybe when you play a four-player game, you might win one in four games. The people who are the best communicators routinely win more than half their games.”

Tostado said he has written a few scripts that haven’t been produced yet. “Maybe I’ll come back to them in the future, when my kids have grown up,” the father of three said.

He is no longer actively producing any films as he concentrates on his career with New York Life.

A new puzzle to solve

Tostado and his wife had their youngest child at the beginning of the COVID-19 pandemic, and he realized he needed to shift careers. He wanted something that would provide the flexibility he needed as a parent as well as a more sustainable income. He earned an MBA online and passed the FINRA Series 65 exam because he wanted to learn more about investing.

New York Life reached out to him and said he would be a good fit for a career with the company. 

“This was not something I initially considered for myself, but it turned out to be a good move for me,” he said. 

“I really enjoy the social aspects of this job. I get to meet with a lot of different people, and every person I encounter is like a new puzzle to solve because everyone’s situation is unique. I enjoy having conversations with people to figure out what we offer that can be the right fit for them and help them get some peace of mind.”

Tostado works with many young parents who are getting settled in their careers and realize they have loved ones to protect. 

“If, God forbid, something happens to them and they don’t come home, what can I do to make sure their loved ones won’t be hurting financially?” he said. “Obviously, I can’t help too much with the emotional burden of losing a loved one, but if I can help on the financial side and help them to have that peace of mind, knowing that if something were to happen we have life insurance or income protection solutions so they’re not in a position where they can’t pay the mortgage or other expenses their family faces.”

Tostado also works with small-business owners, and he has found a niche working with the owners of San Diego’s many microbreweries.

“One of the projects that I worked on as an independent film producer was a documentary about the microbreweries of San Diego County, Calif.,” he said. “We have more than 150 breweries in San Diego right now. 

“One thing I learned while working with them was that they have employees. They need to offer benefits as well. But because a lot of those businesses are so focused on making sure that the next beer gets finished in time so they can keep the taps flowing and the doors open, they’re not taking the time to think about what the future of their company is. They don’t have the time to make sure that they’re providing enough benefits to their employees to be able to make sure that they won’t leave to go to the company across the street that’s offering better benefits. So helping these microbrewery owners recruit and retain employees for their benefits is something that I enjoy doing.”

Tostado is active in the San Diego affiliate of the National Association of Insurance and Financial Advisors. His service to the organization and to his profession earned him one of NAIFA’s 4 Under 40 Awards in 2024. 

Will Tostado ever give up the insurance business to go back to producing films? 

“I’m still a member of the Producers Guild of America, but I don’t want this to take away from what I’m doing for my clients,” he said. “When my kids are older, I might do some creative writing for fun. And if someone wants to produce a script that I’ve written — great! But right now, my focus is on my financial practice and serving my clients to the best of my ability.”

Susan Rupe is editor in chief, magazine, for InsuranceNewsNet. She formerly served as communications director for an insurance agents' association and was an award-winning newspaper reporter and editor. Contact her at [email protected].