Richard Ceffalio Jr. has completed marathons and Ironman competitions, including three marathons in 2024 alone. For Rich Ceffalio, endurance sports are one part of a life built around family, faith, and service to the Chicago area where he grew up.
Born in Chicago in 1972 to an Italian-American family, Richard was raised in a household where Sunday dinners and extended family gatherings were a regular part of life. That upbringing gave him an early sense of loyalty, hard work, and generosity. He attended Notre Dame High School in Niles, Illinois, where his Catholic education reinforced those values, and later studied at DePaul University in Chicago. Community work has been a steady thread for Richard Ceffalio Jr. He received the Outstanding Achievement in Leadership Award from Dreams for Kids, a Chicago nonprofit that creates opportunities for young people facing adversity, including children with disabilities and those from underserved communities. He has also served on the boards of the National Kidney Foundation and the Columbian Club of Chicago.
His volunteer and charitable work covers a range of causes. Richard has supported Elevate Life Church and Toys for Tots, helped with Meals for the Homeless on Thanksgiving, and in 2023 worked at a food pantry sorting, packing, and handing out food to local families. He has donated to relief efforts for California wildfire victims and to Champions in Christ, a nonprofit serving people with special needs and their families, a cause he cares about personally.
Rich lives in Illinois with his wife, Nicole, and their three children. Birthdays, holidays, sporting events, and graduations are occasions the whole household makes time for, and he makes a point of ensuring no one is left out.
Outside of training, Richard Ceffalio Jr. spends much of his free time outdoors. He enjoys boating and fishing, which he finds calming, and plays pickleball with friends and family. He also likes sports cars and long drives on clear days as a way to unwind. The Ceffalio family travels often, and Long Beach has become a favorite place to slow down by the ocean and spend time together.
What is your typical day, and how do you make it productive?
I wake up at 3:15 am every morning; I head to the gym or run. I incorporate workouts, meditation, cardio, weight training, sauna, and cold plunge at 6:45 a.m.; I am at the office attacking my day. I am done with dinner around 5-5:30. I prepare my next day by laying out my clothes for both gym and work. Write out my next day. I review the current day. I unwind with reading and journaling and go to bed by 8:30 pm.
How do you bring ideas to life?
I write the idea down in plain words before I talk about it with anyone. If I can’t explain it in two or three sentences, it isn’t ready. Then I find the smallest version I can try and get it in front of the people it’s meant to help. Most ideas change once they meet real feedback, and that’s fine. I don’t wait for certainty before starting. A clear direction and a willingness to adjust are enough.
What’s one trend that excites you?
AI taking over the repetitive parts of work. A lot of people worry it will replace judgment, but I think it does the opposite. When software handles the routine tasks, the things only people can do become more valuable: listening, building trust, and making a call when the information is incomplete.
What is one habit that helps you be productive?
Training. I’ve run marathons and done Ironman races, including three marathons in 2024, and I treat workouts like meetings I can’t cancel. The discipline carries over into everything else. When you’ve already done something hard that day, the rest feels more manageable, and you’ve kept one promise to yourself.
What advice would you give your younger self?
Slow down. Most decisions aren’t as urgent as they feel. Taking a day to think rarely costs anything, and it often saves a lot. I’d also tell myself to invest in relationships early, because they grow in value over decades.
Tell us something you believe almost nobody agrees with you on?
Something I learned from Inger, my significant other. Slowing down is often the fastest way forward. Most people admire speed, and speed has its place. But I’ve seen more good work ruined by rushing than by patience. Taking the time to think, listen, and wait for the right moment is usually treated as a weakness. I think it’s one of the most underrated skills a person can have.
What is the one thing you repeatedly do and recommend everyone else do?
I only promise what I know I can deliver. Most people overpromise because they want to be liked in the moment. When you say less and do exactly what you said, people learn they can count on you. That kind of trust takes years to build and is easy to lose.
When you feel overwhelmed or unfocused, what do you do?
I get outside. A run, time out on the water, or a long drive on a clear day resets me faster than anything else. Then I write down the two or three things that actually matter that day and let the rest wait. Feeling overwhelmed usually comes from treating everything as equally important, and it almost never is.
What is one strategy that has helped you grow your business or advance in your career?
Staying rooted in my community. I grew up in Chicago, and being part of the same place for a long time means people know you beyond your job title. The relationships you build through charity work, serving on boards, and everyday life last longer than any marketing.
What is one failure in your career, how did you overcome it, and what lessons did you take away from it?
Early in my career, I was a people pleaser. A client asked me to do something I knew was wrong—ultimately, to commit perjury. I refused, but my mistake was that I wasn’t firm and unequivocal enough in saying no. When I wouldn’t do what he wanted, allegations were made against me that I believed were unwarranted.
I overcame it by sitting in the fire, leaning on my faith, and refusing to compromise who I was. It taught me one of the most important lessons of my career: learn to say no. You can serve people without pleasing people. Stand in your integrity, no matter what it costs you.
I also learned that a reputation can take decades to build and minutes to put at risk. Protect it accordingly.
What is one business idea you’re willing to give away to our readers?
A small-group training program for working professionals, built around accountability. The same group meets early each week, and after every workout there’s a short conversation about one goal outside the gym. People stick with fitness when someone expects them to show up, and the same is true for career goals. Put the two together and people would keep coming back.
What is one piece of software that helps you be productive? How do you use it?
An app or tool you use every day, and how it helps.
What is the best $100 you recently spent? What and why?
Personal is great here. Something for the family, a race entry, gear for the boat, anything.
Do you have a favorite book or podcast you’ve gotten a ton of value from and why?
As a man thinketh James Allen – you are truly the sum of all your thoughts, and there is power in the tongue
What’s a movie or series you recently enjoyed and why?
Top Gun – I enjoyed the action and pushing the envelope and being the best of the best
Key learnings
- Clear direction matters more than certainty when turning an idea into action.
- Promising less and delivering exactly what was said builds more trust than big commitments.
- Patience is an underrated advantage, and most decisions are less urgent than they feel.
- Discipline built through physical training carries over into professional life.
- As AI takes on routine work, human judgment and relationships become more valuable.