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Amy O’Meara Chambers of HealthBridge: “Everything will be okay in the end. If It’s not okay, it’s not the end”

“Everything will be okay in the end. If It’s not okay, it’s not the end.” We all know about the entrepreneur roller coaster, but what most people struggle with is that there isn’t just one. We spend most of our weeks moving from one roller coaster to the next. I’ve heard the quote is often […]

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“Everything will be okay in the end. If It’s not okay, it’s not the end.” We all know about the entrepreneur roller coaster, but what most people struggle with is that there isn’t just one. We spend most of our weeks moving from one roller coaster to the next. I’ve heard the quote is often attributed to John Lennon. My guess it was a wry comment about trying to be happy in a life filled with never ending challenges — like being an entrepreneur


As a part of our series about women who are shaking things up in their industry, I had the pleasure of interviewing Amy O’Meara Chambers.

Amy O’Meara Chambers, JD, is the COO and Co-founder of HealthBridge Financial, Inc. She has over 25 years of experience working in the healthcare industry as an employee benefits attorney, executive, and entrepreneur. Amy is the author of “HSAs for Dummies” and holds a J.D. from the University of Michigan Law School and a B.A. from The University of Chicago.


Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

I started in the employee benefits industry three decades ago, so I have certainly put in my “10,000 Hours.” My first job in the industry was as a health plan underwriter fresh out of The University of Chicago. “Umm…did they just say undertaker?” I remember having to go to the library to look up what an underwriter was after I had accepted the job. A few years later, I went back to school at the University of Michigan Law School with the intention of becoming a globe-trotting litigator. But, what I realized very quickly was that I was more of a lover than a fighter, and there were so many interesting and collaborative things for me to do in the benefits world. I was hooked on healthcare. Since law school graduation in 1996, I have enjoyed a broad career working as an employee benefits attorney, a health plan executive, a product developer, and a business builder in the insurance and healthcare industries. It’s fun at this stage to start disrupting things because I know what needs improving, I know what can be shaken up, and I know what probably needs to stay in place.

Can you tell our readers what it is about the work you’re doing that’s disruptive?

We’ve created a first-of-its-kind benefit designed to help bridge the gap between the high cost of healthcare and a person’s ability to pay for it. We’re also setting out to completely revolutionize the revenue cycle management industry. When a member consumes healthcare, HealthBridge covers the costs immediately on their behalf — co-payment, coinsurance and deductibles. Then, HealthBridge provides the member with a consolidated monthly statement, plus guaranteed, friendly repayment terms, giving them financial security and flexibility. HealthBridge becomes a financial safety net, so that when patients want or need care, they can get it with confidence. Often, people will delay necessary care because they can’t afford the deductible, which has costly consequences. People stay sicker, for longer. Employers lose worker productivity and providers see their outcomes erode. By giving patients financial security alongside the health plan they select, they prevent the unhealthy ripple effect from happening. It’s a game changer — especially as value-based provider reimbursement models continue to expand. HealthBridge benefits every stakeholder — the provider, the patient, the employer, and the payer — so that everyone wins, which is a true rarity in today’s healthcare ecosystem.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Over the last three decades, I’ve made countless mistakes. However, I’m not sure I would categorize any of them as funny. Painful, instructive, necessary — yes. Funny — no. I’m probably too much of a perfectionist when it comes to my work to find my own mistakes very comical. You learn as you grow older that much can be gained from mistakes — like them or not.

We all need a little help along the journey. Who have been some of your mentors? Can you share a story about how they made an impact?

Most of my mentors probably didn’t even know they were my mentors along the way and would probably not accept the label. I have had so many. My favorite one was undeniably my late father who I thought was the greatest entrepreneur of all time. I got to work with him for a few years before his death, and I learned so much just sitting at his proverbial feet. He was so smart and always operated with a spirit of fairness and I hope to always emulate that.

In today’s parlance, being disruptive is usually a positive adjective. But is disrupting always good? When do we say the converse, that a system or structure has ‘withstood the test of time’? Can you articulate to our readers when disrupting an industry is positive, and when disrupting an industry is ‘not so positive’? Can you share some examples of what you mean?

I love this question because “disruption” in healthcare is often a dirty word. So I don’t often use it. Every healthcare employee will tell you that their to-do list is a mile long. Plus, because of its complexity, you cannot change things in healthcare on the fly without risking adverse impacts downstream. That’s why I’ve been dedicated to effectuating positive change in healthcare without creating chaos in the system. My co-founder and I had two design principles going into HealthBridge — first, whatever we created had to benefit all of the healthcare stakeholders (no zero-sum games), and second, whatever we created had to ride on the current healthcare “rails” — meaning using in-place technology, process and procedure. Being innovative in healthcare without being seen as disruptive is key to gaining traction for your product.

Can you share 3 of the best words of advice you’ve gotten along your journey? Please give a story or example for each.

“Everything will be okay in the end. If It’s not okay, it’s not the end.” We all know about the entrepreneur roller coaster, but what most people struggle with is that there isn’t just one. We spend most of our weeks moving from one roller coaster to the next. I’ve heard the quote is often attributed to John Lennon. My guess it was a wry comment about trying to be happy in a life filled with never ending challenges — like being an entrepreneur

“ Tell a good man very little and a bad man nothing.” This is the one that I love and probably repeat the most. It originated with my grandmother. You use it when you are posing the question “how much should I disclose?” in a situation where there is conflict. Consider the recipient of the information. Bad men, disclose nothing; everyone else, very little. You’ll thank me for this one.

“Beware of experts.” It’s difficult, but be wary of the “experts” that suggest they know more about your business than you do. It seems like a perfectly rational approach to appoint authorities the task of evaluating your business. However, I’ve found that “experts”, as a group, are perhaps the least suited to identify new ideas or assess your startup

We are sure you aren’t done. How are you going to shake things up next?

I’m totally hooked on this new member financial experience area. I started my career designing high deductible health plans, and I hope to go out figuring out how to help people navigate and pay for them. This is just the beginning of this all-important space and my co-founder and I plan on being its thought leaders.

In your opinion, what are the biggest challenges faced by ‘women disruptors’ that aren’t typically faced by their male counterparts?

I am fortunate that healthcare is filled with women leaders, so when it comes to most of my meetings with healthcare stakeholders, I usually see myself reflected around the room. Because I’ve worked in the industry for so long, it is rare that I am not met with respect. When it comes to the venture capital world, it’s the rare event when I stare into a webex and a female face stares back at me. With that said, while it may be a little more difficult to navigate the small talk that starts each pitch (I’m not sure that I’ve ever watched an entire football game and I definitely don’t fly fish), I have to say that once we start talking shop, we all just become experts in our respective areas.

Do you have a book/podcast/talk that’s had a deep impact on your thinking? Can you share a story with us?

I’m a podcast and YouTube junkie. Not a day goes by that I don’t dial up an inspirational or educational one. How did we live without them? For entrepreneurs, I recommend NPR’s “How I Built This,” VC:20, Masters of Scale, The Life Coach School, Impact Theory, and the Stanford GSB Series.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I would create a movement that encourages local companies to work with early-stage startups. More important than capital, entrepreneurs need that first customer. Entrepreneurs have amazing ideas to bring to the world. But, companies are often so reluctant to give those ideas a chance. I would love to find a way to reward companies that give them a safe space to test their wares. Entrepreneurs like me could always have a job with a nice salary and benefits, but you want us out there doing what we do best — creating.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

My favorite Life Lesson Quote is: “A setback is a setup for a comeback.” You have to believe that the universe is for you, so no matter the setbacks you face, you must always tell yourself that good things are right around the corner. Many things are working for your good in the background. We all suffer setbacks, but the optimistic person knows that it’s hard to keep a good (wo)man down.

How can our readers follow you online?

The best way to follow me online is on LinkedIn and on our company’s website: www.myhealthbridge.com

This was very inspiring. Thank you so much for joining us!

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