CEO Knew ‘It Was Time’ and Stepped Onto the Path to Retirement

Mary Starr

When Mary Starr formed The Starr Group, a Milwaukee-based agency specializing in insurance and risk management, the goal had always been for the firm to perpetuate internally and remain independent.

After working with a consultant who told her and her team it could take 10 years to reach the goal, Starr realized it wasn’t going to work out the way they’d hoped.

“It was definitely a process,” Starr said. “We realized things were not where they needed to be. So, we talked to them about … this potential change of direction, and they were all on board.”

The “potential change of direction” involved finding a buyer for the company. The team – which included her husband and her son – began reviewing prospective buyers, starting with a dozen, then whittling it down to five.

The arrival of the pandemic in 2020 complicated things, forcing them to do it virtually – “It was basically business on the top, yoga pants on the bottom,” Starr said with a smile – out of her dining room.

Before getting started, though, they established what Starr called six “non-negotiable” goals, including protecting the team, protecting the company’s culture, the ability to have autonomy and the ability to collaborate.

They found what they believed to be the right buyer in Acrisure, which now partners with The Starr Group to provide insurance and risk management solutions to their clients and allowed Starr to retain her position with the new firm. She stayed on for a bit over four years.

And then …

“It was time to step away, and I stepped away gradually,” she said. “I went part-time October (2024), and then I (retired) full time Jan. 1.”

Starr, who earned a bachelor’s degree in social work, sociology, criminology, with a minor in Spanish from the University of Wisconsin, talked about her career and a variety of other business issues during a recent episode of “CEO Thought Leadership Series on LinkedIn Live,” the discussion series hosted by the National Association for Business Resources.

Produced in conjunction with the Best and Brightest Companies To Work For and Corp! Magazine, the series is hosted by NABR CEO Jennifer Kluge and features business leaders from around the country.

Jennifer Kluge: Was the decision to retire a difficult one?
Mary Starr: This was a huge step for me because I wasn’t necessarily ready to step away. But I knew the timing was right, and I had watched so many business owners hang on way too long, and I made a promise a very long time ago that I would not get in the way of progress. But yes, this has been a huge step.
In the beginning I couldn’t even say the word retire. I would just say every word but retire. My name had been on the building. My name is on the business. It was my identity for 40 years. So this was a huge process. My biggest concern was not having that sense of purpose.

I wasn’t going to leave it to chance. And one that really stood out for me was Rewire, Don’t Retire by Sadler and Myers. And then I began to think about, you know, what are my bucket list items and what do I want to accomplish in this next chapter? And I switched to really looking at it as an opportunity to create a brand new chapter.

My mantra became, this is not happening to me. This is happening for me at the exact perfect time.

Kluge: Two (common non-negotiables) are protect your team and protect your culture. That’s very, very hard to do in an acquisition or a sale. Looking back at it, how do you think those two non-negotiables have played out after the sale?
Starr: I think they played out well for the first four years, and then during this transition to regional platforms, it became a bit muddled and so unfortunately did not end up as strong as it started.

Kluge: Looking back at the whole experience, the work that goes into preparing for sale … Is there anything you would have done differently?
Starr: When I look back, maybe realize the amount of inevitable change, but I don’t think there’s anything I could have done differently that would have prevented that. So going through the process, no, nothing that I would really have done differently.

Kluge: What is the impact of retirement on you as a human, and how can you help others prepare for that transition?
Starr: I can honestly say I’m embracing the next chapter with an open mind, considering my options, chipping away at my bucket list items. And in all honesty, I’m so busy right now I don’t even know how it would fit my previous work into my daily schedule.

Kluge: Can we ask a little bit about what what some of the bucket list items are for you and how you’re attacking those?
Starr: Actually, I’m a very physically active person … I do hot yoga. I (went) on a yoga retreat in this place off the coast of Mexico that you can only get to with a 45-minute boat ride. And then in May, I’m a big hiker biker. I am actually doing the Camino in Spain, so it’s a pilgrimage in northern Spain, where we walk for two weeks and it’s about 105 miles. A very spiritual journey. So I am doing both of those. A couple other, in my background was in social work, and I have this passion to give back.

So I’m considering a couple podcasts and I’m doing some work on that. I’m looking at doing some volunteer work in a local correctional institution, helping the grieving of of inmates there. And then, you know, just spending time and staying in the present. I mean, I was going 100 miles an hour for so long that I am just really trying to stay present, reconnecting with family and friends.

I am being cautious not to quickly overcommit on things because I think that’s part of my personality. So right now I would say I’m chipping away and things are going well.

Kluge: So what advice would you give to a whole generation of people still in it to win it?
Starr: My first piece of advice would be to always embrace who you are. We each have our own unique talents, strengths and gifts. I never intended to be in this business. In fact, I was adamantly against being in this business. It was the founders of this business were my mother and father-in-law. My father-in-law would tell me all the time, “Oh, you would be great at this. You should come in the business.” And I used to respectfully listen that my inside voice was definitely saying something different. And my mother in law, sadly, was diagnosed with cancer, and I stepped in temporarily to help out. That was 40 years ago, and I’m still here today.

But the reason is because I stayed true to who I was. I held on to what I was passionate about, and as I said, my undergrad and my graduate degree was in social work and which does not seem to correlate to insurance, but because of that passion I brought in, you know, the caring about other individuals. That’s where our wellness and our corporate initiatives were born.

The second thing I would say would be to embrace challenge. I had so many challenges over the years, and truly from my darkest moments came my greatest growth.

Life is meant to be challenging. Facing your fears is what enables us to grow, and every challenge faced is a character building opportunity. So when you have challenge, embrace them. You will be a stronger person because of it.

Kluge: You’re very passionate about wellness. You are a certified wellness coach. I know you received the Best and Brightest In Wellness award, among other wellness awards. You said that this was your passion as from social work to focus on wellness within your organization. What led you to this and what is the business case for wellness in the workplace?
Starr: The initial seed was planted by David Honeycutt, who was the CEO of the Wellness Council of America at the time. And this goes back all the way to 2017. And he had used the words that the vast majority of cultures are here by default, but only a precious few have been built by design.

And I remember how that resonated with me, the idea of consciously building a culture and how that could overall transform your whole organization, because I believe culture is so vitally important. I always refer to culture as the invisible hand that guides your organization. And as far as the business case, so strong in our in our instance, the biggest impact by focusing on wellness and culture was on employee recruitment, engagement and retention, all of which impacts your bottom line.

Healthy employees are more engaged. They’re more productive, which allows you to be a more profitable organization over hand. And I saw this firsthand, and I had the data to back this up because as our wellness and culture initiatives grew, so did our productivity and our performance indicator numbers, which are those vital business indicator numbers of growth, profitability and customer retention.

Kluge: You have another best practice that I want to make sure we share. You created culture by design. There’s in your definition of culture by design. There’s 15 ingredients to build a fantastic culture. Can you just share a couple of them with us of those 15?
Starr: And this was something that was just created organically over the past 25 years. So, I’ll highlight a few. So the ingredients for building a strong culture. The first one I believe, is you need to start with a true commitment to the value of culture. If you are not truly committed, if you do not see this as a strategic initiative, it will be very hard to dedicate dollars, resources, time.

And it will be very, very hard for this to get off the ground. And then I would say to start the process by taking an honest and honest assessment of your current culture. Look at your strengths, things that you need to build on. Look at your weaknesses. Things that you need to replace or get rid of, get rid of, or to strengthen.

Kluge: What is the hardest part of leading that nobody talks about? You kind of have to just suck it up as a leader.
Starr: For me, it was really setting those boundaries and having a healthy balance of caring for your team, but also knowing you have tough decisions to make on behalf of the entire team. And so is really keeping healthy boundaries so that you’re able to make those tough decisions.