Design by Chris Nicholls
“While entrepreneurship is not as glamorous as Instagram makes it look, it’s also not as daunting in some ways. You have problems and you just have to come up with solutions.”
Eight years ago, Chris Wolpert was faced with a choice.
After building a career in the insurance business with an eye toward owning his own agency, his plans to buy out his retiring partner’s book of business fell through. At home, he and his wife learned they were expecting their third child.
“It was quite easily one of the most stressful periods of my life,” says Wolpert.
In retrospect, it would also become one of the most rewarding; although he knew he could join a big firm or get hired at a carrier, Wolpert chose to continue to pursue his entrepreneurship goals.
“My goal the whole time was that I was going to own an agency,” he says. “I decided that I was going to do this no matter what; if I failed, at least I wouldn’t wonder. Part of the decision was setting an example for my kids.”
Learning to pivot
Wolpert’s original career aspiration was to be a sportswriter. He studied journalism at Washington State University and landed an internship covering the school’s sports teams.
“At the time, it was kind of a dream job for me,” he says. “I got to cover my college’s football team; I got to meet players and coaches. It was super fun.”
To his surprise, though, all of those things became less appealing when he was working late into the night on deadline writing about the team’s wins while his buddies were out celebrating them. Realizing he wasn’t as passionate about his chosen career path as he expected to be, Wolpert pivoted.
He decided to try his hand at insurance, thinking it would be a safe and easy career. He started working in insurance claims, but soon realized it also came with its own set of challenges. So Wolpert transitioned into financial services in 2009, amid The Great Recession, and after “muddling through” for a few years, found himself gravitating toward the employee benefits market.
“At the end of 2010, the Affordable Care Act was being proposed and I had a lot of clients at the time who said they needed help navigating all the new compliance requirements,” he says. “I saw that as my opportunity to really go deep and specialize within group health insurance and explore what this new landscape was going to mean for employers.” Wolpert moved into the benefits space, joining a small agency with two producers and hoping to become a part of the owner’s transition plan. But, once again, things went differently than expected.
A new start
After the deal to buy out his partner fell through, Wolpert founded Tacoma, Washington-based Group Benefit Solutions in 2016, where he juggled learning to be an entrepreneur with being the firm’s only employee and salesperson for two years.
“It was quite a challenge,” he recalls. “There was a point in the early days where I was bringing on clients and losing them almost as fast. It was frustrating.”
But he persevered. Wolpert says the early years of GBS were a process of trying new ideas and finding alternative ways of building health plans that were different from how things had been done for decades.
In the years since then, the firm has gained its footing, experienced tremendous growth and developed an identity as an agency with a mission to eliminate employees’ out-of-pocket costs while guiding them to the highest quality health care available.
One of the most successful growth strategies Wolpert discovered was leveraging partnerships.
Despite its success, the firm still only employs three people: Wolpert, Diane Bendixen, the company’s client success leader, and Wolpert’s wife, Valerie, who works in account management and helps with other tasks. But through the power of several partnerships, GBS is a family business that can offer the capabilities of a large brokerage.
“I've been able to partner with people for benefits technology, non-medical benefits, compliance, marketing and medical management,” Wolpert says. “It's quite a team that we're able to surround our clients with. We can protect them from a compliance perspective, bring them solutions as far as cost-containment, improve outcomes, and offer a very robust set of business solutions around benefits management.”
With the right team and solid processes in place, GBS has not only grown, but has not lost a client since 2019.
Known for spending a significant amount of time getting to know clients, Wolpert strives to bring in clients who are partners in his mission to break the status quo in health care benefits. He says GBS’s philosophy is to bring in “WOW” clients (clients who are great to work with even though they might not be the biggest accounts) rather than “OW” clients (the ones that seem to generate problems at every turn).
Industry influence
In recent years, Wolpert and GPS have also begun to garner notoriety in the industry, speaking at industry conferences and being featured in BenefitsPRO’s Face of Change. Wolpert has embraced a role as both a thought leader and mentor to the wider benefits industry.
“Chris frequently attends conferences and meetings as a guest speaker,” says Bendixen. “He takes time away from his own business and family to inspire other advisors, new and old, to do their very best and to stay motivated. I hear him frequently taking calls from other brokers and business owners who are looking for advice and inspiration. He will always drop what he's doing to take the time to connect and help.”
As for his thoughts on the direction of the industry, Wolpert says he thinks the Consolidated Appropriations Act (CAA) is set to disrupt the industry in the same way that ERISA changed the landscape for workplace health and retirement plans in 1974 and the Pension Protection Act disrupted the retirement planning industry in 2006.
“I really see it as an area of opportunity,” he says. “I think the CAA could end up being one of the most disruptive things that we've seen.”
A day in the life
When the pandemic hit in 2020, GBS was ahead of the game, because Wolpert built the agency from the ground up to operate remotely.
“I wanted to build a business around my lifestyle, rather than the other way around,” he says. “I wanted to have the structure and flexibility so that if one of the kids gets sick, I can drop what I'm doing and go pick them up from school. Our lifestyle doesn't have to interrupt or be dictated to us by our business and our professional lives.”
For Wolpert, that means being there to get his kids on the bus for school and off the bus at the end of the day, as well as taking time to work out first thing in the morning and completely unplug during his lunch hour while getting some fresh air and taking his dog for a walk. He is also a coach on his kids’ soccer teams, which he says not only challenges him, but brings him great joy.
Wolpert balances his work and family responsibilities to support his wife’s entrepreneurial pursuits. In the evenings, Wolpert makes dinner and helps his kids with homework while his wife runs practices, camps and clinics at the competitive cheerleading gym she has owned for more than a decade.
“I took a lot of inspiration from watching Valerie and realizing that while entrepreneurship is not as glamorous as Instagram makes it look, it's also not as daunting in some ways,” he says. “You have problems and you just have to come up with solutions. It's no different than if you're a W2 employee or you're working for somebody else. The stakes are much higher, but everything can be figured out.”
Bringing creativity to insurance
Although he decided a career in sports writing wasn’t for him, Wolpert says he learned valuable skills while studying journalism that he has been able to apply to the benefits business. He developed tools during his college classes that have helped him become an effective communicator, whether through slide decks, marketing events, participating on podcasts or speaking at events. He learned the importance of understanding his intended audience and how to reduce noise factors so he can get his message across and keep people’s attention.
“I think that entrepreneurship is very much an exercise in creativity, although most of us maybe don't think of it that way,” he says. “Sometimes when you're getting into process and procedure, you start to lose a little bit of that creativity, but I think one of the things that I'm good at is being able to see where creativity can exist and where it can help inform the processes that we’re putting in place.”
To distinguish himself in a crowded and competitive market, for example, Wolpert decided to write a book about building a health plan in the post-ACA environment. The goal was to create a cornerstone for his marketing strategy and build credibility.
“I got done with the outline and I realized, this is really boring,” Wolpert says. “I don’t even want to write this book, so nobody’s going to want to read it.”
Instead of giving up on the idea, however, Wolpert decided to pivot. Inspired by an idea he heard on a podcast, Wolpert began outlining a comic book about an HR director and CFO tasked with finding ways to control their health care costs in their workplace kingdom.
The comic book, titled “Hit Zero: The Quest to make Healthcare a Controllable Expense,” was released in 2021, and a sequel is in the works this year.
Wolpert has also flexed his creative muscles by helping to produce a documentary due out this spring called “It’s Not Personal, It’s Just Health Care,” which portrays the various challenges facing the health care and benefits industries, as well as the solutions that are making a difference across the nation.
Wolpert also regularly posts videos of himself reciting fables, which he started doing to engage with his audience. The process has helped him build discipline in posting on social media and to learn more about video editing. But most importantly, putting himself on camera was a way of pushing himself.
“In order to grow professionally, I think you first need to grow personally,” he says. “And in order to grow personally, you have to get out of your comfort zone. That's where real growth happens.”
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Chris Wolpert is passionate about using creativity to educate and create change
Chris Wolpert is passionate about using creativity to educate and create change
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Photography by Tom McKenzie
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