“We had some land outside of town that had a barn on it, and I'd get up at 5 o'clock in the morning and drive out there and take care of the animals, and then drive back, shower, go to school, go to football practice, and when I was done with football practice, I’d drive out to the barn and take care of the animals again,” says Hamilton. “It was a long day.”

That type of hustle and entrepreneurial spirit are, perhaps, a product of a bygone era. He says he feels caught somewhere between two generations – not Gen X but not quite a millennial. He didn’t have the internet until his freshman year of college or a cell phone until his junior year, and says he had to be committed and disciplined to keep up with all the things he did.

“It required me to really pick what was important to me and dedicate myself to it.”

Higher education

“I wanted to be a rancher when I grew up,” Hamilton recalls. As a child, he had his eye on attending Texas A&M University, just an hour and a half away from his hometown, but his family wanted him to go to school further away. He initially planned to study agriculture, but a family friend who worked as an energy commodity trader convinced him to study finance instead.

“He told me, ‘You can do agriculture with a finance degree,’” recalls Hamilton. “He said finance is the study of money and every organization in the world needs to know how to manage money. That convinced me to try it.”

Hamilton attended Hardin-Simmons University in West Texas, a small private school where he played football and was a four-year varsity letterman. He was able to study finance and economics, while also studying agriculture at a sister school through a dual-credit program.

This focus on finance and economics ultimately drove the trajectory of his career.

Beginnings in banking

Hamilton started his career as a commercial banking officer and spent 12 years ascending in the banking industry before making a change to insurance.

“If you told me 20 years ago I'd be in this business, I would have said you were crazy, because I didn't know anything about health insurance,” Hamilton says. “In fact, I had friends who were in the business, and whenever open enrollment came up, I used to call them to help me figure out what plans I should buy. I didn't like insurance; it was confusing and it was expensive.”

Instead, he excelled at his work in finance, which included working with one of the biggest insurance brokerages in the United States on its acquisition strategy. He enjoyed the moving parts of private equity, capital and debt raising that were involved with acquisitions and was fascinated by all of the questions that went into making an acquisition work.

“I was looking at it more from enterprise-level economics,” says Hamilton. “I never really asked the question of how it works for the client.”

He started thinking about the end-user experience around 2013, just a few years after the Affordable Care Act passed, when he was helping raise debt and equity for a $600 million syndicated transaction involving five banks.

“Everybody started getting cold feet, and they were worried that the ACA was going to harm the earnings of these brokerages,” says Hamilton, who was then working as the vice president of commercial banking at BBVA, a global financial services group. He also started hearing from other stakeholders that the ACA would be a boon to the health insurance business and grow the earnings of brokerages.

So he began talking with his clients about how they managed the increasing costs of health insurance. One client told him they simply budgeted for increases every year and hoped the carrier and the broker brought them rates close to what they budgeted. He was astonished that companies could accurately predict their prices for plastic and metal two or three years out, but couldn’t figure out the health care piece. He was even more surprised when they told him there was nothing else they could do.

Insurance rabbit hole

This line of inquiry led him down a rabbit hole of learning how the insurance industry is designed and why health care insurance costs always go up. He compares trying to understand cost increases to using a thermometer to diagnose a fever: You know the temperature is rising, but you don’t know if it’s because you have COVID, the flu, or a kidney infection.

“The way most employers react to rising health insurance costs is to just change insurance companies, reduce the benefits, or raise co-pays and deductibles,” Hamilton says. “That's like taking Tylenol to treat the flu; but if you've got an infection and you don't get it diagnosed properly, that infection can spread and cause bigger problems.”

The underlying problem, he says, is that the major insurance providers are not incentivized to lower health care costs. In fact, they are disincentivized, because their profit margins are capped on the insurance portion of their business. So it makes sense that they would want premiums to increase so their profit is based on a larger number.

In addition, Hamilton says they have increasingly become vertically integrated – owning pharmacy benefit managers and health care providers and controlling the distribution of expensive drugs – which allows them the freedom to charge whatever they want.

“They can overcharge the insurance company to show lower earnings, which they use to justify higher premiums, but they don't tell you they made a bunch of money on the medications that were filled and through their health care providers. To me, that's a conflict of interest.”

Transitioning to insurance

Hamilton said it was a lightbulb moment when he realized that addressing this misalignment could reduce the cost of health care, which would in turn reduce the cost of insurance for employers. His focus in the beginning was not on helping employees with health care as much as helping employers lower costs so they could be more profitable.

His transition to the insurance industry came in 2015 when he joined Gus Bates Insurance, Investments & Consultants as a senior consultant. There he spent three years focused on helping clients maximize the value of their employee benefits programs and designing custom benefits programs.

“I didn't know what it was going to look like when I got into the business,” he says. “But the longer I worked, the more I realized how far these misaligned incentives and conflicts went.”

His quest to fix the health care system led him to Carrollton, Texas-based agency Hotchkiss Insurance, where today he is a partner and the employee benefits practice leader. He leads a team of consultants and specialists focused on helping companies improve performance and profitability, while helping them build customized health plans that leverage independent pharmacy benefits managers. His goal is to help employers understand what they are buying and how much they are paying for it, which is difficult information to access with traditional health care benefit plans.

“Once you know what you're buying and what you're paying, you can determine if it is a good price,” says Hamilton. “It's not about reducing benefits; it's about making sure we're buying the right thing and paying the right price.”

The payoff

Hamilton’s approach has proven to be beneficial for clients of all sizes. Keating Auto Group, which owns new and used car dealerships across Texas, brought Hamilton on as its benefits advisor in 2019 and say he has been a catalyst for the continual evolution of the company’s health plan.

“He introduced us to a handful of new programs which have proven to save our plan money year after year,” says corporate HR director Taylor Barton. “The programs include B-Smart cancer infusions, direct primary care, direct contract agreements with hospitals near our dealerships, a foundation that directly supports plan members and reduces our plan costs, PBM programs that also help our members save, and a new physical therapy program we are excited to add this year. We are a self-funded plan, so the constant advancement and introduction of cost-saving programs allow us to keep our premiums low for members and costs low for our plan.”

Beyond his innovative approach to health plan management, Hamilton also works to raise awareness for the industry at large, says Spencer Smith, SVP at Pareto Health, a risk financing platform for employee health benefits focused on lowering health care costs for small and mid-size employers.

Hamilton regularly shares content through social media channels under the Benefits Insider brand, which provides the perspective of someone with inside knowledge of the industry. He is also active in the TRUE Network, which facilitates collaboration among employee benefits firms on best practices in consulting, operations, sales, leadership and agency management. Smith says Hamilton is a source of information for his peers, including his competitors, and regularly meets with them to discuss ideas.

“He has the confidence that he is one of the best in the industry and doesn't perceive sharing ideas with industry peers as a threat,” says Smith. “True to his nature, he wants everyone to be better for the greater good.”

Hamilton’s appetite for information about how to improve the health care insurance market is evident when he interacts with colleagues.

“I think there's such a need in our industry,” says Hamilton. “Change is scary and it can be hard, but my goal and my charge to the rest of the industry is that the people who are doing the right kind of work should be willing to teach others how to do it as well.”

The 2025 Advisor of the Year will be announced at the BenefitsPRO Broker Expo, May 6-8, 2025 in Boston, MA. The winner will be further profiled after the announcement.