A resident of Holland, Massachusetts, Kenneth Denning heads his own investment and management firm and spearheads various real estate development activities. He has operated roughly a dozen successful restaurants and nightclubs, including 36 Luis Street in downtown Hartford, Connecticut. Kenneth Denning has also been successful as a house flipper and real estate developer.
Although he has accomplished much as an entrepreneur, Mr. Denning describes inventing as his “number one passion.” An inventor since childhood, he has acquired numerous patents, which include an oil can with a pull-tab top.
Mr. Denning has established a history of charitable giving, supporting veterans through donations to an American war hero organization and first responders through donations to local police and fire departments. His other major philanthropic efforts focus on fighting pediatric cancer. His contributions have earned him honors from the Connecticut Cancer Foundation, St. Jude Children’s Research Hospital, Shriners Hospitals for Children, and the Dana-Farber Cancer Institute.
What is your typical day, and how do you make it productive?
My day starts with morning exercise and prayers, then I go for a walk with my dogs. When I come back, I have a coffee and start checking the stock market, making phone calls, and checking emails.
How do you bring ideas to life?
I follow through with my ideas and inventions for seeing the future and remain committed to seeing them through.
What’s one trend that excites you?
The real estate market and how it is always evolving across different parts of the country. Not only that, but it’s also influenced by economic conditions, demographic shifts, and societal trends.
What is one habit that helps you be productive?
Always telling myself to finish what I start.
What advice would you give your younger self?
I would emphasize the importance of education: go to college and get a Bachelor’s Degree.
Tell us something you believe almost nobody agrees with you on?
Do not dwell over the past, there is nothing we can do to change it. Your health is extremely important and shouldn’t be taken for granted. I am 69 and feel great, happy to be alive, and healthy and blessed.
What is the one thing you repeatedly do and recommend everyone else do?
Never stop learning, whether that is reading, taking an online class, or doing something to stimulate your mind.
When you feel overwhelmed or unfocused, what do you do?
I meditate and/or go out for a walk with the dogs.
What is one strategy that has helped you grow your business or advance in your career?
I have always looked for new business opportunities through networking. I’ve found that has helped provide insight into business ideas, along with ways to grow my business that I have not necessarily thought of.
What is one business idea you’re willing to give away to our readers?
Turnkey Airbnb Rental Finder. Helping investors buy and manage profitable short-term rentals without the hassle.
What is one piece of software that helps you be productive? How do you use it?
Quickbooks, Microsoft Office, and sometimes AI apps like DeepSeek. Quickbooks allows me to maintain efficiency in running my business and MS Office- I like to focus on Outlook and Excel to remain organized and productive.
Do you have a favorite book or podcast you’ve gotten a ton of value from and why?
My favorite podcast is the Joe Rogan Experience. I find his guests very entertaining and insightful, but his appeal is also in the fact that Rogan’s unique style, diverse guest lineup, and the cultural moment it taps into, is entertaining. Plus, his interview style is not fake, it’s curious, engaging, and natural, and he features high profile and sometimes controversial guests.
What’s a movie or series you recently enjoyed and why?
Recently finished watching the Zero Day series on Netflix starring Robert DeNiro. It shows just how much chaos a cyber-attack can cause to this country if we are not fully prepared for it.
Key learnings
- Small, consistent rituals and accountability (e.g., self-reminders) build long-term efficiency.
- Intellectual agility and exposure to new ideas unlock opportunities.
- Pivoting with a solution-oriented mindset turns setbacks into growth.
- Success hinges on anticipating trends and executing relentlessly.