Confessions of a Hollywood elite advisor

Counting some of Hollywood’s biggest names among her clients, it’s little surprise that Beverly Hills-based Dana Hollinger’s guiding mantra also happens to be the title of a 1989 Spike Lee film.

Do the right thing. That four-word credo was first proffered to Hollinger by the man she proudly calls her mentor, the late California billionaire businessman and philanthropist John E. Anderson, for whom the University of California Los Angeles named its graduate school of management, and with whom Hollinger regularly discussed life and business as one of 30 or so women he invited to be part of Club 1800, an informal group of female business and community leaders.

“John [Anderson] changed my life. It was like being mentored by the Coach Wooden of billionaires,” she says, referring to another UCLA icon, legendary basketball coach John Wooden. “[Anderson] taught me to always do the right thing; he taught me to try to do things that make the world a better place; and he taught me that everything you do should be profitable.”

Now the 56-year-old Hollinger is out to change lives herself and make the world a better place — and to be profitable in the process. She’s doing so not only via Dana Hollinger Group, the life insurance-focused estate planning and financial planning firm she founded in Beverly Hills in 2007, but also in her new role as a member of the Board of Administration at CalPERS (California Public Employees’ Retirement System), the organization that manages retirement benefits for more than 1.7 million California public employees.

From fantasy to new reality

Hollinger, who began her career as an attorney, might never have found her way into the life insurance business, nor into the affluent market, were it not for an out-of-left-field encounter with legendary professional sports agent Dennis Gilbert.

After meeting Gilbert, a life insurance-focused advisor whose work with athletes led him to become a sports agent, at an early 1990s business function at which he was a speaker, the two struck up a friendship that eventually led to Hollinger becoming Gilbert’s partner in a fantasy baseball league. “We would meet once a week to talk about our fantasy team, and he’d always ask me, ‘Did you ever think about selling insurance?’”

She hadn’t, but the lifestyle nevertheless appealed to Hollinger at a time when she and her then-husband were considering starting a family. “I looked at the life insurance industry and thought I could have more of a life than if I continued to practice law, because carriers aren’t open on weekends,” she recalls with a tinge of laughter.

Eventually, she yielded to Gilbert’s prodding and in the mid-1990s, earned her state life insurance license and then took a position as an agent for Nationwide Provident. Now she and Gilbert work in the same rarified Beverly Hills air, although Hollinger says she largely eschews professional athletes as clients. “As a woman, I realized I wasn’t going to make it with [male professional athletes]. They want to get their people around them, and most of those people are men.”

So instead of targeting athletes, Hollinger zeroed in on the life insurance needs of business owners. Then, after leaving Nationwide in 2005, she began honing her focus on high-net-worth clients as a producer at Succession Capital, working with AIG offshoot AI Credit on complex life insurance premium funding cases. “That put me in the uber-high-end market,” she says. “It changed who I was talking to.”

It also helped further develop the skillset and the perspective she has been drawing upon to thrive in the affluent market. “I was there to see why things went awry for families that didn’t have adequate life insurance to cover estate tax liability.”

Hollinger says focusing largely on difficult-to-finance cases gave her a keen understanding of not only the applications for life insurance as a risk-management and wealth-transfer tool for the wealthy, but also of how life insurance dovetails with other assets inside a portfolio, including real estate and a range of investment vehicles commonly used by HNW clients, such as private placements.

These skills have helped Hollinger differentiate herself in a market crowded with advisors angling for the affluent. “Most [life insurance-focused advisors] don’t bring that kind of expertise to the table,” she says. “I’m respected and I’m looked up to because of it.”

But to build a successful life insurance practice around high-net-worth clients, the “soft” people skills have to match the hard. Following her move into insurance, Hollinger shared an office with her fantasy baseball co-owner Gilbert. “What I learned there — and what sports agents do really well — is that you have to service your clients. Dennis taught me to take care of your people.”

Hollinger’s work alongside Gilbert, and later with Succession Capital, also opened her eyes to the importance of teamwork in serving ultra-affluent clients.  “Anybody who’s that wealthy works with a team of advisors,” she explains. “So you have to be comfortable working with other professionals — trust and estate attorneys, CPAs, business managers, those types of people.”

As valuable as Hollinger’s two-year stint at Succession Capital was in sharpening the skills she’d need to succeed in the HNW segment, it left her feeling burned out. So in 2007, she returned to the agency world with AXA Equitable Life.

Four more years as a captive agent left her craving true independence. “I really felt the only way I was going to get my shot was to start my own independent practice,” she explains. “One thing I had going for me was a good network and people skills. Why would I want to give those to a company other than my own?”

HNW headway

Dana Hollinger didn’t rise to the top of a male-dominated field by being passive. Rather, she seems unafraid to seek out new frontiers, whether it’s diving into the geekish world of fantasy baseball, pivoting professionally from law to life insurance, bonding with a billionaire, taking her practice independent, as she did in 2011, or raising a teenage son as a single mom, all while running a business and serving in a vital government-appointed post.