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.

dana hollinger

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.

An avid runner, Hollinger craves a competitive challenge, as evidenced by her decision to hang the DHG shingle amid the stratospheric opulence of Beverly Hills. “I actually think being a jock has taught me how to compete and be resilient,” she says.

When she’s not out pounding the pavement or parenting, Hollinger spends the bulk of her professional time helping high-net-worth clients address issues related to wealth transfer, business succession/continuity, financial planning and multigenerational estate planning.

To thrive in the HNW space, observes Hollinger, it’s important to work both on and in your business. That means setting aside time to focus on networking, cultivating relationships and brand-building. Since the types of clients Hollinger targets are largely unmoved by traditional marketing vehicles such as seminars, direct mail and advertising in the media, she finds most of her business through referrals from clients as well as other professional advisors, including those with whom she works as part of clients’ advisory teams.  “I try always to be in front of people and other advisors. Years and years of speaking in front of professional groups, of socializing and building relationships, and strong follow-up. I’m always booking appointments with centers of influence.”

But beyond face time and flesh-pressing, the real fuel for the referral engine that drives a high-net-worth-focused practice like Hollinger’s is trust, which, in the case of clients, links back to her DTRT mantra. “It’s not always about making the sale,” she says. “It’s about honoring your clients’ best interests.”

Trust is central to the identity Hollinger has sought to forge for herself and her practice. “I think I have created a very good brand for myself in the professional community as a woman in a male-dominated field who excels at what she does. People trust in my ability to unravel and solve complex problems, and they also trust in me and my good name.”

Moving the needle

In May 2014, that good name, along with a unique professional skillset, earned Hollinger a nomination to the CalPERS board by California Gov. Jerry Brown.

As steward of more than $290 billion in public employee pension assets, risk management is among CalPERS’ weightiest responsibilities. That plays directly to Hollinger’s strengths. “My orientation,” she says, “is hedging risk.”

Calling Hollinger “very bright and very knowledgeable,” CalPERS President Rob Feckner says the organization will lean heavily on her risk management and life insurance expertise in managing its massive pension portfolio. Hollinger serves on three of the organization’s committees: investment, finance and administration, and board governance. “She’s going to have a full plate,” says Feckner, “and I believe she’s up to the task.”

Hollinger is the first women to represent the life insurance industry on the CalPERS board. “That’s very important to me,” she says. “I want my legacy to be that I helped improve the [California pension] system, but I also want to move the needle by opening the door for other women. That’s important to me.”

As comfortable as Hollinger professes to be working in a male-dominated business, her next frontier — and potentially, the next big growth area for her practice — is all about moving the needle for women.

To that end, she’s in the early stages of building out a segment of her practice to focus on financially empowering women who, she says, too frequently take a back seat in financial decisions. “I see my [female] contemporaries, who tend to defer to others, when it comes to their money. My goal is to help them make more educated decisions, and decisions they’re comfortable with, about their money.”

Hollinger says her plan is to offer a broad spectrum of services to a wide range of women — not just the affluent — via online and brick-and-mortar advisory channels, perhaps aligning with other like-minded advisors to deliver those services.

“I see a shift where the insurance industry is starting to focus more on female clients,” she says. And it’s about time, because when you elevate women, you elevate society.

John Anderson couldn’t have said it more eloquently.

See also: 

That’s rich! Lessons on managing high-net-worth customers

6 celebrity estate planning lessons from 2014

Advisors must better serve women, social media-savvy millennials