Amy O’Meara Chambers of HealthBridge

There are so many good reasons why women should become founders. I think that women are hardwired to be entrepreneurs. In my opinion, empathy — or, understanding your customer — is the most important quality of an entrepreneur. Empathy is at the heart of all design. According to research on this subject, we are often more empathetic than our male counterparts.

As a part of our series about “Why We Need More Women Founders”, I had the pleasure of interviewing Amy O’Meara Chambers, JD.

Amy is the co-founder and COO of HealthBridge Financial, Inc. HealthBridge has set out to revolutionize the way individuals pay for and manage high out-of-pocket healthcare costs. Amy 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 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.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

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.

Is there a particular podcast or book that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

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.

Do you have a favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life or your work?

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 have you used your success to make the world a better place?

I believe that I have — or, at least that was my goal in starting HealthBridge. I have been fortunate to experience a series of successes throughout my life — first as a student, then as a lawyer, then as a business executive, and now as an entrepreneur. Lots of hard work paired with a lot of good luck along the way. All of it has led me to this moment in my career. With HealthBridge, I have the opportunity to change the face of healthcare in a way that benefits all of the participants in the healthcare ecosystem — healthcare providers, insurers, employers, and, most importantly, every American who worries about affording healthcare when they need it for themselves or for their family members. I am honored by the opportunity to do this important work.

Let’s now jump to the primary focus of our interview. According to this EY report, only about 20 percent of funded companies have women founders. This reflects great historical progress, but it also shows that more work still has to be done to empower women to create companies. In your opinion and experience what is currently holding back women from founding companies?

It’s not a pipeline problem. Women represent 56% of college students (and, let’s be clear, you do not need a degree in order to start a business), 40% of full-time MBA programs, and over half the workforce. I believe the percentage of female founders should catch up to male founders over the next decade if we can close three gaps that I believe have held women back from founding companies:

  • First, it’s a vision problem — and only time will close this gap. It’s hard to envision a career path that has never been revealed to you and that seems unfamiliar. I didn’t become a founder until I had worked for other people for nearly 25 years. I was born in the late 1960’s — just as married women began to enter the workforce. For women of my generation, there was no blueprint for a bold career choice like starting a company. My mother went to an all-girls high school that had three tracks — secretarial, nursing, and teaching. She had one friend who went to college. And, while everyone in my generation was college-bound, I can’t say that I knew a single woman, when I was growing up, who led a company, let alone started one. I have such hope for these young women as they see more women starting and leading companies. My daughter and her friends now major in entrepreneurship, start businesses while still in school, compete in pitch contests and connect in start-up incubators. They can envision the path to starting a company because they have seen other women taking what was once the road less traveled.

  • Second, it’s a financial issue — also curable over time. Starting a company takes capital. If you want to maintain a strong equity stake, you will use a lot of your own; and, even if you are using someone else’s capital, founders understand that you must have a nest egg to withstand the financial storms that will inevitably arise. Women are just now in positions to accumulate the wealth necessary for them to take big financial risks. Female wealth that is accruing every day will accelerate the rise of the female founder.

  • Third, it’s a network gap — and we can fix this now. Female founders need access to business leaders willing to give women what they need most — their first customer. As business leaders become more intentional in championing women founders when making buying decisions, we will see the numbers change. Same goes for venture capital — the more venture firms that seek to fund women founders, the more we will come to the table to start companies. Together we can close this network gap by supporting practices of inclusion and continued emphasis on representation within the business and start-up community.

Can you share with our readers what you are doing to help empower women to become founders?

I try to put my time and money where my mouth is. Over the last decade, I have advised a number of female founders as well as enrolled in a women’s year-long program aimed at supporting the female entrepreneur. I also recently invested in a female-founded company — putting first money in and lending my experience in this early stage. The woman leading this new company is a new mom with two small children. She is brilliant and much braver than I was at her age. I couldn’t be prouder of her or more excited about what she is building.

This might be intuitive to you but I think it will be helpful to spell this out. Can you share a few reasons why more women should become founders?

There are so many good reasons why women should become founders. I think that women are hardwired to be entrepreneurs. In my opinion, empathy — or, understanding your customer — is the most important quality of an entrepreneur. Empathy is at the heart of all design. According to research on this subject, we are often more empathetic than our male counterparts.

The woman founder often makes a better story. Startups start as stories. We tell these stories to investors and ultimately to our first customers. Because female founders have often taken a different path to entrepreneurship than their male counterparts, these stories are often more interesting and more genuine.

Female founders also bring unique perspectives to markets — particularly those that are male dominated. This diversity of viewpoint often creates new solutions that can revolutionize industries. We often create the change that we desire to see in this world.

Ok super. Here is the main question of our interview. Can you please share 5 things that can be done or should be done to help empower more women to become founders?

We can accelerate the growth of female founders by:

  1. Put female business leadership on display in early education. Highlight success stories. Show our girls how it’s done and how to get there. Give them a vision for their future self.
  2. Earmark venture funding for women. We make great portfolio investments. An investment in a female founder today paves the way for more to follow.
  3. Support startup ecosystems for women. Give women a place to collaborate and create networks that will help them navigate the difficulties of entrepreneurship.
  4. Support programs that are proactive in ensuring that corporations use women-owned, women-founded, women led companies for the procurement of goods and services. Also, urge companies to become a first customer for female founders and celebrate those that do.
  5. Bridge the female representation gap in senior leadership throughout US companies. The widespread positive impact that equality in the boardroom can achieve is almost immeasurable. We all know that in the end, when women benefit, we all benefit.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number 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.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

I would love to meet Anne Wojcicki, co-founder and CEO of 23andMe. I’ve long had an interest in genomics and was part of a startup that attempted to marry genetic testing with employer-sponsored health plan management. I marveled at 23andMe when it first hit the market. It was extraordinarily difficult to launch, I’m sure, and I can almost hear all the doubters who told her that the federal and state regulations, as well as Americans’ fierce protection of privacy, would make her product a non-starter. But look what she’s been able to do! It’s hard to find a person nowadays who hasn’t mapped their genetics with 23andMe.

How can our readers further follow your work online?

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

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.