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For Joshua O’Gara, CLU®, ChFC®, CFP®, Owner and Founder of O'Gara Financial Group, entrepreneurship runs in the family. Both of his parents were small business owners and O’Gara inherited their drive. His entrepreneurial spirit—along with his college studies in economics and his desire to help people—made a career in insurance and financial services a perfect fit. 

The Keys to Success 

The most important qualities for an agent or advisor, says O’Gara, are tenacity, drive, and curiosity. He explains the importance of curiosity. “You have to be very curious about people, about your business, and about developments in the [insurance and financial services] industry,” he begins. “I think NAIFA is a great way to stay on top of a lot of those developments and stay connected with other advisors in the business to maintain a very strong position in the industry.” 

Over the past 16 years, O’Gara’s career has followed a winding road, he says. Now, he is a multiline agent, and his clients are primarily small companies of blue-collar workers—plumbers, construction workers, and electricians. Collaborating with small companies, he says, allows him to get to know their employees on an individual level. He takes an educational approach to help his clients understand their financial plans and provides a trusted source of information for people often overlooked by professionals who prefer to work with high-net-worth clients.  

Making a Difference 

O’Gara is a passionate advocate for his clients. He talks about one experience working with a client who had an opiate addiction. The man’s insurance company was refusing to pay for in-patient treatment. He had already tried outpatient treatment and was concerned he wouldn’t get the medical care he needed. With O’Gara’s help, his insurance company agreed to cover his in-patient treatment. “That's why I do what I do,” says O’Gara. Who knows what could have happened if he hadn’t gotten the treatment?”  

The Power of Political Advocacy 

Growing up in Boston, O’Gara never considered himself a political person. “Politicians are just crooked” was a common sentiment. However, when O’Gara attended NAIFA’s Annual Congressional Conference in Washington, D.C., he saw the impact NAIFA's political advocacy could have. One of his fellow NAIFA-MA members was running for office, and O’Gara was asked to attend as a voting delegate. When he visited Capitol Hill, he says, he “caught the bug.”  

Talking with elected officials, O’Gara saw the opportunity NAIFA members have to help inform legislation to benefit American consumers. “Sometimes it may feel like we don't make much of a difference. But just being able to put a personal face on the issues that we deal with on a daily basis is extremely important,” he says. “We're never going to agree with our officials about everything, but I think we can agree on more things than we disagree on. And having that opportunity to sit down and have those conversations has proven to be very fruitful—not only in my professional career but personally as well.” 

To those reluctant to get politically involved, O’Gara says, “Give it a shot." He describes the importance of sharing a financial professional’s perspective with elected officials, saying, “There are a lot of issues facing the country right now in terms of financial insecurity. It's really important for professionals to be relaying the message to legislators in terms of how potential laws or bills they're considering could have an impact on our clients. It's never going to be perfect, but if you’re not involved in those discussions, you’ll never have your voice heard. 

The Value of NAIFA 

Through the years, O’Gara has held several leadership positions within NAIFA. He currently serves as President of NAIFA-MA and has served on the National Young Advisor Team Committee and was the Regional Vice Chair of NAIFA-MD's Political Involvement Committee. He is also a NAIFA Financial Security Advocate and a graduate of NAIFA’s Leadership in Life Institute (LILI). The friendships he built through the LILI program, he says, have provided him with an invaluable support network—people he can lean on when times get tough—and great friendships. “My membership dues have been paid for a thousand times over—not only from a monetary perspective but from personal growth as well,” he says. 

The biggest reason to join NAIFA, O’Gara says, is the breadth of knowledge NAIFA members can offer. Being a NAIFA member allows O'Gara to share ideas with those in his area of expertise and learn about other practice areas from those outside of it. He learns the approaches that work for other industry professionals and implements those ideas to take his business to the next level. “[NAIFA] is really valuable because you get a much more well-rounded perspective on not only your practice but the financial services industry as a whole,” says O’Gara. “It's something everyone should be a part of.” 

Outside of the Office 

When he’s not working, O’Gara loves spending time outdoors with his wife and two children. They enjoy hiking, snowboarding, and skiing whenever they can. 

O’Gara also volunteers with Family Movement, a non-profit organization that strives to help Boston’s unhoused population find affordable housing and employment and teaches financial literacy. Typically, after a year or two, program participants are able to start looking at home ownership. “It's great to see the families persevering through some very difficult times over the last couple of years,” says O’Gara. “They've shown amazing resilience and resolved to be able to stick to their goals.” 

For his service to his community and our industry and association, we’re #NAIFAproud to have Joshua O'Gara as a part of our NAIFA family. 

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