Alexandra Eidenberg of The Insurance People: “Work ethic, connections, the will to persevere, the ability to see light at the end of tunnels, and good wine”

Work ethic, connections, the will to persevere, the ability to see light at the end of tunnels, and good wine. Any business is only as strong as its leader which means you have to be mentally and physically ready to take on the roller coaster ride that is business ownership and entrepreneurship. There is no […]

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Work ethic, connections, the will to persevere, the ability to see light at the end of tunnels, and good wine. Any business is only as strong as its leader which means you have to be mentally and physically ready to take on the roller coaster ride that is business ownership and entrepreneurship. There is no boss and there is no schedule. You have to self motivate and build the ladder as you climb it and take folks up it with you. Many days are tough, sometimes money is tight, sometimes you lose clients, deals or friends and it’s a balance that is amazingly beautiful but also hard. Knowing folks to lean on, learn from and contact to grow your business is key and being able to leverage your network be it your parents, best friend, old colleagues or Twitter fans is a must. And good wine or whatever it is you prefer to drink be it coffee, tea, beer or wine. You have to remember that with the roller coaster comes grace for yourself and those around you. Always remember to relax, recenter and enjoy the moments. I prefer mine with wine and coffee. However you take yours, just make sure to create that space for yourself.


As a part of our series about “Why We Need More Women Founders”, I had the pleasure of interviewing Alexandra Eidenberg.

Alexandra Eidenberg is a small business owner, community activist, mom of 4 kids, wife and lover of all things food and running. Alexandra owns The Insurance People, an insurance agency that specializes in health insurance for individuals and small businesses. When she is not working the insurance lines she is a fierce advocate for women and children wearing the hat of IL State Chair of Vote Mama, Co-Chair of Membership for Invest to Elect, and Executive Board Member of New Trier Democrats.


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 was born and raised in Chicago and am a product of Chicago Public Schools. I worked retail for years and my core genius has always been sales. I got involved in the community at a young age, and as I got older, I wanted to live more passionately. I knew there had to be a way to combine community and business allowing me to use my sales skills.

Can you share the most interesting story that happened to you since you began leading your company?

Owning a business is like building a plane while flying it. It is always interesting. That said, I think growing my family alongside my business has always been interesting. My business was my first baby and then I had twins followed by two more children within three years. Being a mom changed everything for me. It made me stronger, wiser, and smarter. I work smarter and I teach my team to do the same. It is about work-life balance amidst the craziness.

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?

Mistakes in my industry tend to not be funny. I always say I make insurance fun and inviting but really it is a very stressful industry that is hyper regulated. We bring as much fun juice to the party as we can, but at the end of the day, it is still insurance. So the funniest mistake we probably made early on was renting out our office to a group of folks that played poker super late at night. At the time it seemed like a great way to help afford the rent. In the end, we realized we were sharing the office with stoners. That relationship ended very quickly!

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?

I am grateful for my team. Every day. All Day. My team is my greatest asset and I love them. They work super hard and totally embody the work hard play hard mentality. I have been very lucky to meet amazing business coaches and seasoned business owners that have supported me and rooted me on, but at the end of the day, my team is why I am successful. They are just the best!

Ok, thank you for that. 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?

As a women’s rights activist, the numbers always pain me! The stats always show that us gals are not where our male counterparts are and it stinks. I think it comes down to the basics though. Most women are more risk averse, crave stability and have imposter syndrome. This keeps us from taking the big leaps it takes to be business owners and entrepreneurs.

Can you help articulate a few things that can be done as individuals, as a society, or by the government, to help overcome those obstacles?

I am big on legislating everything but you can’t legislate personalities and societal norms that have been created over generations. I think what we can do is lead by example. Show other women the way, take them up the ladder with us, open doors for them and show them that it is possible. When folks do not see people like them in places of business ownership or leadership they can’t envision themselves there. As business owners the more young women we can show the way, the better. I have the pleasure of leading my daughters Girl Scout Troop and I am constantly teaching business and leadership skills.

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

Let’s be honest ladies, we are super bad ass! Women rule the world even if we are not getting the credit for it. We harness energy, power, brilliance and beauty and when we are seen and heard we do amazing things. It is the latter that is harder. Being seen and heard is difficult, and once that is mastered, you can accomplish anything.

What are the “myths” that you would like to dispel about being a founder? Can you explain what you mean?

I am not sure about any myths but I think it is important to know that the harder and smarter you work the more successful you will be. It is also important to know when to throw in the towel or say no. Saying no at the right time is critical.

Is everyone cut out to be a founder? In your opinion, which specific traits increase the likelihood that a person will be a successful founder and what type of person should perhaps seek a “regular job” as an employee? Can you explain what you mean?

Not everyone likes working their tail off for a dream or a vision. Being a business owner is a 24/7 job. You either love the hustle or it’s not for you.

Ok super. Here is the main question of our interview. Based on your opinion and experience, what are the “Five Things You Need To Thrive and Succeed as a Woman Founder?” (Please share a story or example for each.)

Work ethic, connections, the will to persevere, the ability to see light at the end of tunnels, and good wine. Any business is only as strong as its leader which means you have to be mentally and physically ready to take on the roller coaster ride that is business ownership and entrepreneurship. There is no boss and there is no schedule. You have to self motivate and build the ladder as you climb it and take folks up it with you. Many days are tough, sometimes money is tight, sometimes you lose clients, deals or friends and it’s a balance that is amazingly beautiful but also hard. Knowing folks to lean on, learn from and contact to grow your business is key and being able to leverage your network be it your parents, best friend, old colleagues or Twitter fans is a must. And good wine or whatever it is you prefer to drink be it coffee, tea, beer or wine. You have to remember that with the roller coaster comes grace for yourself and those around you. Always remember to relax, recenter and enjoy the moments. I prefer mine with wine and coffee. However you take yours, just make sure to create that space for yourself.

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

Everything is about family and community. Insurance is insurance but family and community are everything. I spend the majority of my time helping people and fighting for equity in our communities. When you treat the community well your community treats you and your business well. I spend a lot of time and energy taking my kiddos out and about to fight for democratic values like the right to choose, gun violence prevention, environment, and education equity. I also invest in local causes and candidates to make sure our communities have leaders that care about all of our communities.

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.

#DemForLife like the side of my glasses read. The movement is political energy and in the direction that serves all our communities and environment. As a business owner, community activist, and mom of 4 I know my purpose is to bring communities together to serve and be stronger together. I preach it and practice it.

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.

Wowza, if I could have lunch with that special someone. I would love to have lunch with Kamala Harris. The woman is a rockstar and I am so grateful she is our vice president.

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

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