Lift Your Legacy: How an introvert found her voice, founded two companies, and still has time for her family with Samantha Foster and Rabbi Jacob Rupp

My biggest challenge to date, both personally and professionally, is being too introverted. The ironic thing is that I am often complimented for being a great speaker and being very confident and personable when meeting new people. This is due to the techniques I developed — and to the fact that I think of it as riding […]

The Thrive Global Community welcomes voices from many spheres on our open platform. We publish pieces as written by outside contributors with a wide range of opinions, which don’t necessarily reflect our own. Community stories are not commissioned by our editorial team and must meet our guidelines prior to being published.

My biggest challenge to date, both personally and professionally, is being too introverted. The ironic thing is that I am often complimented for being a great speaker and being very confident and personable when meeting new people. This is due to the techniques I developed — and to the fact that I think of it as riding a roller coaster. You get butterflies in your stomach as you wait in line, but once you are seated on the ride, your nerves are replaced by excitement and you enjoy the ride.

Samantha Foster is the founder of Chief Insurance Solutions LLC, a workers’ compensation insurance brokerage, and Rethink Mental Health Incorporated, a nonprofit dedicated to mental health education, awareness and empowerment. He ambition and drive as a 20-something year old founder and President of two organizations is inspiring, as is the work she does to make a positive impact on the world. She accomplishing all of this while maintaining balance with her personal life and family.

Thank you so much for doing this with us! What is your “backstory”?

I have been an entrepreneur for as long as I can remember. When I was in kindergarten, I drew and cut out a paper dog and then drew a room on a piece of paper with its food bowl, bed, toys, etc. This simple toy became a sensation in my class and I was asked to make copies for numerous kids. The thrill of creating something desirable and sharing it with others was intoxicating. From then on, I daydreamed of one business idea after another. In every job I had, I imagined ways I could do it better. Then finally, after working at a commercial insurance brokerage for some time, I took a leap of faith in my abilities to do it better and launched Chief Insurance Solutions LLC.

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

As of October of this year, I now lead two companies, my insurance brokerage and a nonprofit organization, Rethink Mental Health Incorporated. We officially launched Rethink Mental Health Incorporated on October 10th which is World Mental Health Day. To my surprise, a local news network called me that very day to interview me for a segment on mental health awareness. When I got the news station, the first thing they asked was for me to spell my name to the camera, which I did. When they then asked the name of my organization, I jokingly asked, “do you need me to spell that, too?” They laughed and explained that they just want to make sure it is spelled correctly since my name would be written on screen. We went on to have a nearly 20 minutes interview touching on all areas of mental health awareness, the initiatives of my nonprofit organization and what the future of stigmatization could look like. I returned home, full of excitement, waiting for the segment to air. Finally it was on, but to my surprise the editors only used about 20 seconds of my interview and incorrectly published my name as “Stephanie Foster” instead of Samantha Foster, despite the fact that I literally spelled in out for them. It was an honor to be asked to participate in the segment, but by the end of it, being on the news was one the most underwhelming experiences of my life.

What was your biggest challenge to date either personally or professionally and how did you overcome it?

My biggest challenge to date, both personally and professionally, is being too introverted. This is problematic because in my professions, being an extroverted person is essential. If I could, I would conduct all business over email so I don’t have to put myself out there, but that is neither realistic nor productive for my profession. When I spoke with other people, whether it was for meetings or conferences, I had to combat quite a bit of anxiety before mustering up the courage to put myself out there at first. The ironic thing is that I am often complimented for being a great speaker and being very confident and personable when meeting new people. This is due to the technics I developed to overcome my introverted fears. What works best is connecting it metaphorically to riding a roller coaster. You get butterflies in your stomach as you wait in line, but once you are seated on the ride your nerves are replaced by excitement and you enjoy the ride.

What does leadership mean to you and how do you best inspire others to lead?

Leadership means instilling confidence in others to be the best they can be. I inspire other to lead through setting an example and validating efforts, big or small. Prior to starting my own companies, I had an assortment of different bosses or leaders. In observing them and working for them, I learned what traits make a good leader, but more often what traits make a bad boss. Upon expanding my companies, my number one priority was to be the boss/leader that I would want. Someone thoughtful, personable, respectful, helpful, understanding and kind.

Those traits are reflected in the way I validate my staff and colleagues. Validation is a powerful thing that many bosses do not take the time to do. By celebrating successes and a job well done and positively talking through mistakes or roadblocks, I make it known that I care and that I want what is best for them as opposed to just what is best for my bottom line.

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?

I owe my success to my husband. Since before we were married, he believed in me, often more than I did. Whenever I got frustrated or felt stuck, his support and confidence inspired me to keep at it! My business became particularly vulnerable after our son was born. Being a new mom, I underestimated how challenging it would be to balance work and a newborn. After a month of struggling, my husband volunteered to quit his job to help me with our son so I wouldn’t lose momentum on my work. He sacrificed his career and fought his own drive to provide for our family in support of me and my business. It was a decision that not only allowed me to balance my professional and personal life, but gave us the incredible gift of raising our son together.

Was it difficult to fit your life into your business/career and how did you do that?

It was not too difficult to fit my life into my business because having a work/life balance was my goal and priority upon starting my companies. This value became especially important when I envisioned starting a family of my own one day. I didn’t want my job to keep me from the irreplaceable moments of raising a child. For these reasons and more, I structured the work I did for my companies around my home life. I found this easier and more adaptable than starting a career and then needing to then structure it around a home life.

Did you find that as your success grew it became more difficult to focus on the other areas of your life?

Even as my success grew and as I founded a second company, I maintained a strong work/life balance. By prioritizing time for my personal life when structuring my professional roles and responsibilities, the balance more easily fell into place, even when faced with growth or more time-consuming projects.

Can you share five pieces of advice to other leaders about how to achieve the best balance between work and personal life?

  1. Be Organized. From to-do lists to color-coded agendas, keeping all of my tasks and communications organized allows me to have a more concrete idea of my day-to-day schedule. This not only keeps my work efficient, but opens up time for my personal life.
  2. Delegate. As an entrepreneur, it can be difficult to let someone else be responsible for certain aspects of your business, but being open to delegating and outsourcing frees up significant amounts of time for your personal life.
  3. Work from home. The simplest way to stay close (literally) to your family, is to work from home, at least part of the time. It is comforting to know I am just a hallway away from my son and I can pop out to see him whenever I want.
  4. Work 24/7. Work doesn’t stop just because you are socializing, even after hours. Whenever I am out of the office, I am still tuned into work and am able to answer calls or emails on the go.
  5. Choose wisely. The fact of the matter is that not all jobs allow for a balance of personal and professional life. If having a good balance is your priority, you will need to find a job and profession that allow for that kind of flexibility.

What gives you the greatest sense of accomplishment and pride.

What gives me the greatest sense of accomplishment and pride is helping people and spreading joy. Whether it is a workers’ compensation insurance client seeking help with their business or child who suffers in silence with mental health issues looking for acceptance and kindness from their peers. Even since I was a little girl, I’ve wanted to make a positive difference in peoples lives. As an example, when I was in 5th grade, everyone in class was asked what they wanted to be when they grew up for our yearbook. Some said doctors or lawyers, some said actors or singers, but I said “I want to be known.” And to this day, I hold true to that statement. It doesn’t mean I want fame or fortune, but I want to walk down the street one day and have some near-stranger stop me and say, “hey, you’re Samantha Foster and your work made an impact on my life.” My entrepreneurial spirit inspires me daily with more and more business ideas, and I’m sure I will explore new ventures in the future, but at the core of all of them is a deep desire and intention to help people and spread joy.

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 believe the most amount of good can be spread by acts of kindness. There is no better quality that kindness because it is contagious and the simplest act of kindness can make a real, lasting effect on others, especially if they are suffering in silence. This is the main motivation behind launching my nonprofit, Rethink Mental Health Incorporated, which is dedicated to changing the way we, as a society, treat and view people with mental health issues. At its core it is about being kind, supportive, and accepting of others. This message is especially powerful in the work we do with children at schools.

What is the best way for people to connect with you on social media?

I have an active presence on most social media outlets, from Facebook to Twitter under @RethinkStigma. I am also very active on Linkedin and have over 10,000 connections to date. The direct link for my Linkedin Profile is

About the author: Jacob Rupp is a coach, author, speaker, podcaster, and rabbi. He is the founder of Lift Your Legacy, a community that helps people live a more authentic life. He has a regular, syndicated column that appears in ThriveGlobal and Medium magazine. To learn more about him or to listen to the Lift Your Legacy podcast, search iTunes or visit his site:

Share your comments below. Please read our commenting guidelines before posting. If you have a concern about a comment, report it here.

You might also like...


“You can’t pour from an empty cup”, Claudia Minner and Parveen Panwar, Mr. Activated

by Parveen Panwar, Mr. Activated

“Listen to Your Heart” The 5 Lessons I Learned Being a 20-Something Founder

by Jean Ginzburg

Women in Wellness with Dr. LaQuista Erinna

by Christina D. Warner, MBA

Sign up for the Thrive Global newsletter

Will be used in accordance with our privacy policy.

Thrive Global
People look for retreats for themselves, in the country, by the coast, or in the hills . . . There is nowhere that a person can find a more peaceful and trouble-free retreat than in his own mind. . . . So constantly give yourself this retreat, and renew yourself.


We use cookies on our site to give you the best experience possible. By continuing to browse the site, you agree to this use. For more information on how we use cookies, see our Privacy Policy.