Daniel Sergi is a retired CEO with over 45 years of experience in the insurance industry. He held key leadership roles at major global brokerage firms, including Alexander & Alexander & Co., Corroon & Black & Co., and Willis. Beginning his career as an ambitious Account Executive, obtaining his CPCU (Chartered Property Casualty Underwriting) Designation in his late 20’s and also his Security Licenses, Daniel steadily advanced to Executive Vice President & Managing Director, gaining invaluable expertise in client management, sales, strategic planning, and operations.
In 1994, Daniel transitioned from the corporate world to become the proud owner of Wine Sergi & Co., a respected family-owned insurance agency in the Chicago suburbs. As President & CEO, he spearheaded the company’s growth, expanding it from a small, eight-person team to one of Illinois’ largest independent brokerages in Chicagoland with clients located locally, nationally and internationally. This remarkable success led to the firm’s highly strategic acquisition by Acrisure Corp. in 2015. Throughout his career Daniel sat on numerous For-Profit and NFP boards.
Recognized for his visionary leadership, Daniel has received numerous prestigious accolades, including The Business Excellence Award for Leadership, and Lifetime Achievement Award. Under his leadership, Wine Sergi & Co. was consistently ranked among the “Best Places to Work in Illinois,” earning industry-wide respect.
Now retired, Daniel remains actively engaged in philanthropy, offering financial support and volunteer work for his own charity and various other local charitable causes. While he continues serving on corporate boards he enjoys a more relaxed, fulfilling, and balanced lifestyle with his wife Barbara.
What is your typical day, and how do you make it productive?
A Typical Day is waking up early, preparing a pot of coffee, of course, grinding beans first, and sitting down to read my daily Bible scriptures. My eyesight is challenging these days, so my reading is supported by using strong reading glasses and a lighted magnifying glass. Unfortunately, reading times are limited due to this. Then, I plan my day for chores that often change and vary depending on the season. With the farm, there is never a lack of things to attend to for fixing or preparing for the season. I’m currently building benches to set out on the several miles of paths so one can sit, rest, and breathe in all that surrounds you. We have been very blessed to be the stewards of this beautiful and magical property.
How do you bring ideas to life?
Something I always said in business, and it pertains to anything in life as well…Simply: ”Plan the plan, and work the plan”.
What’s one trend that excites you?
Change in the seasons. The soil, trees, pond, type of birds, and animals you see in each season, for example, all creating a seasons trend. Spring is being present and watching everything come awake, through summer’s lively activities, to fall preparedness of winters coming and winter rest of the soil and timber through mother nature eyes.
What is one habit that helps you be productive?
Always have a list of things to do and get out and do them. Whether it is walking the dogs each day, small items as painting a piece of outdoor furniture, building a small table for the garden, to attending to the veggie garden, to walking the ½ mile there and back to get the mail at the road, even when it is cold and snowing out.
What advice would you give your younger self?
Be present and mindful in everything you do. Life itself pulls us away from what really matters in our lives. Sad but true. Then, as human nature has it, we find this out too late in life.
Tell us something you believe almost nobody agrees with you on?
It would be a movie favorite of mine, as no one agrees with me here LOL. The best movie of all time, in my opinion, is : HARVEY. Produced in 1950, black & white, starring James Stewart and of course, his invisible pooka (6 ft tall rabbit) named Harvey. James Stewart played the role of Elwood P. Dowd. Stewart won many awards for the movie as it was a comedy with mild suspense. Elwood was a calm, happy man who was always dressed to the 9’s, always carried a smile, a business card, and a kind word, and had more friends than anyone could count. He asked them over for dinner all the time. His sister once asked Elwood, “Elwood, she said; don’t you have enough friends”, where Elwood replied, with great respect and admiration to his sister, and inquisitive to his sisters question; “Well Veta, I guess I didn’t know you could have too many friends”? Just a kind man with a good heart. More of what this world needs. He was always inquisitive of others, asking how they were doing, about their families, and if they needed anything.
What is the one thing you repeatedly do and recommend everyone else do?
This took a long time to learn….Take a deep breath, get centered and mindful (with your surroundings and thoughts), and then exhale. Proceed with your day thanking the Creator for all there is, even when things look bleak, knowing He never leaves you and provides for your needs. God is Good.
When you feel overwhelmed or unfocused, what do you do?
I’ve learned to hit the brakes a little. Slowing down doesn’t come naturally to me. I’ve spent most of my life constantly moving, planning, and working on the next thing. But out here, life moves at a different pace, and I’ve had to learn to roll with it. I’ve also realized that conversation is a great cure for feeling scattered. Around here, people don’t rush through small talk. They pull up a chair, sit on the tailgate, and actually talk. I used to be the guy with a checklist, always on the move, but now? I’ll sit with a friend for an hour, maybe two, and just talk about life, faith, or whatever’s on our minds. It’s grounding in a way I never expected.
What is one strategy that has helped you grow your business or advance in your career?
Build real relationships. Not the kind where you shake hands, swap business cards, and move on, but the kind where people actually trust you. Relationships that last for decades.
What is one failure in your career, how did you overcome it, and what lessons did you take away from it?
My greatest failure was not doing a better job in balancing family, faith, and career responsibilities. Careers can pull you away from other very important things and people in life. Don’t forget about the loved ones as you drive forward.
What is one business idea you’re willing to give away to our readers?
Building a successful career can be as easy as starting one hour earlier in the morning and one hour later in the afternoon. In executing your plan, you will gain one full week a month and 12 full weeks a year in productivity and performance. It’s really that easy. It’s amazing what goals you can accomplish. And never eat alone. Whether it is breakfast or lunch, make sure it’s productive with a client or prospective client. And don’t talk about business, it’s about building relationships.
What is one piece of software that helps you be productive? How do you use it?
Alright, I’ll be candid, I’m not the most high-tech guy out there. I spent most of my career relying on handwritten notes, in-person meetings, and good old-fashioned conversations. But if there’s one piece of software that’s actually made my life easier, it’s Google Keep. It’s nothing fancy, but that’s exactly why I like it. It’s basically a digital notepad where I can jot down ideas, reminders, or random thoughts before they disappear from my brain forever. If I’m out walking the farm and remember something I need to do, I just pull out my phone, type it in, and it’s there when I need it later. I also use it to make quick lists—projects around the property, things I need to pick up, even notes for conversations I want to have.
What is the best $100 you recently spent? What and why?
It may sound silly, but we had guests over the weekend for Valentine’s Day. A business relation turned into a long time friend. His wife, daughter, and grandkids were all here for 3 days for a visit. So, the $100 question? Definitely it is buying Valentine flowers for my wife, our women guests and their little daughters for Valentine’s Day. The guys, well they got my own “cold smoked” cheddar cheese. Everyone was happy! But, really, the smiles all around from the ladies and children were heartwarming.
Do you have a favorite book or podcast you’ve gotten a ton of value from and why?
Audio Book: Heaven; by Randy Alcorn
Our life on earth is short, but when we cross, we have eternity in heaven with our Lord. It’s a beautiful thing!
What’s a movie or series you recently enjoyed and why?
Yellowstone: A lesson in life…..This series, to me, was about working hard for what you have, no one giving you anything, achieving the nearly impossible, believing in yourself and others, family challenges, and in the end, the heart, mind & soul ultimately doing the right thing.
Key learnings
- Mindful Living & Present – Slowing down, practicing gratitude, and engaging in meaningful conversations lead to a richer, more balanced life.
- Planning & Action – Productivity comes from structured planning, staying active, and consistently executing tasks, no matter how small.
- Authentic Relationships – Trust and genuine connections matter more than transactions in both business and personal life.
- Faith in our Lord Jesus Christ to guide us.