Founder Story
A journey of rediscovery, built in real time, shared without filters.
"As you get older, you begin to realize time is getting shorter — and my wife and I want to live a full, exciting life with no regrets. Keep exploring life to its fullest until we can't."
— Curt Roese
The Beginning
In June 2023, at the age of 61, I turned off my computer for the last time as a CFO. After years of building someone else's dream, I was burned out and ready for a change.
My retirement was unexpectedly anticlimactic. There was no gold watch, no grand office party. Working remotely due to COVID meant I simply lost access to company systems, received well-wishes from colleagues, and quietly became "retired."
"What I did not know then was that this was not an ending at all. It was the beginning of the most fulfilling chapter of my life."
The Restlessness
My wife Shari and I sold our condo and bought a house that needed remodeling. The project kept me busy, but I could already feel something stirring inside me. A restlessness. A void that needed filling.
This feeling was not new. From 1998 to 2008, I had experienced the profound satisfaction of building a custom home building company from nothing, growing it into an award-winning business in Central Florida. The 2008 recession took everything, my business and my financial security, but that same year brought me Shari, my incredible wife and soul mate.
One lesson had stuck with me: I wanted to build something of my own again, but this time without the high risk, physical offices, and employees. I dreamed of an online business, though I had no specific plan.
The Decision
As retirement settled in, I began facing my life's regrets. One that had always nagged at me was my college experience. I never felt connected to my alma mater and often joked that if I ever won the lottery, I would get my master's degree at Ohio State.
In January 2024, seven months into retirement, I had a surge of momentum. Instead of talking about "someday," I decided to act. I applied to the University of Florida's Master's in Entrepreneurship program, a highly-rated school with passionate alumni.
I reached out to business contacts for recommendations, worked on my application, and confronted my less-than-stellar 40-year-old GPA head-on. Then came the waiting.
The Leap
Congrats, you are accepted at UF.
When that email arrived in April 2024, I felt both exhilarated and terrified. I had committed to this path in front of family, friends, and business associates. There was no turning back.
Even funnier, I was already on academic probation because of my undergraduate GPA from four decades earlier. But I was determined to prove myself. Shari and I drove to campus, walked around holding hands, took photos, and loaded up on Gator gear from the bookstore.
As August 2024 approached, the nerves intensified. What the hell did I just sign up for? I wondered, laughing at myself.
Back in the Classroom
The education landscape had transformed dramatically since 1984. Everything was now online: classes, syllabi, assignments, and textbooks. After the initial adjustment, I appreciated having access to everything 24/7.
Group projects presented another hurdle: coordinating with team members across different schedules and work ethics. I joked with a professor that "in the real world, I could fire non-performers!" But these experiences pushed me to adapt and grow.
Personal Growth
While diving into my studies, I decided to confront another lifetime regret: my weight and health. This had been a personal struggle affecting my confidence despite my professional accomplishments.
Personal Milestone
Today I am at my lowest weight since 1980, practicing Pilates several times weekly with Shari, and hiking when we are in Blowing Rock, NC. I feel better than I have in decades, a confidence boost that has carried into every part of my life.
The Idea
As part of my entrepreneurship program, many classes required business plans. We could either create fantasy companies or develop actual business ideas.
"It would be insane not to take this amazing opportunity to build something."
One early morning, coffee in hand, I sat at the kitchen counter with a notepad for a brainstorming session. Three hours and about 20 scattered pieces of paper later, the concept for Retirepreneur emerged, though not yet the name.
I realized what I truly wanted: to help people like me create vibrant, fulfilling, financially secure futures. Lives without regrets and full of stories worth sharing with grandchildren.
In a subsequent brainstorming session, the name "Retirepreneur" clicked. I noticed "solopreneur" was popular but not trademarked, and I recognized that people our age want to feel part of something: a group, a lifestyle, a community.
A marketing friend loved the name immediately
Discovered the domain was for sale at $500 and purchased it the same day
Applied for a trademark, approved April 2025. Retirepreneur® is official.
The Validation
I developed a comprehensive business plan exceeding 50 pages, complete with pitch presentations and slide decks. My professor encouraged me to enter the Luby Microgrant Pitch Competition.
Without financial pressure, I could thoughtfully develop my vision: how to create value for subscribers and members, what content to offer, and how to deliver it.
Created a 10-minute video pitch embedded in a PowerPoint deck
Mantra throughout: "Experience everything you can during this program"
November 2024: Won initial $5,000 Luby Microgrant for the Retirepreneur concept
2025: Awarded an additional $5,000 as Luby recognized measurable progress. $10,000 total.
The Challenge
The Entrepreneurship Program Director encouraged me to enter the Big Idea Gator Business Plan Competition. This would require a 30-minute live presentation, something that terrified me despite decades of confidence in boardroom meetings.
I explained that I was building a lifestyle business tailored to my age and life stage, not a "Big Idea." They insisted I participate anyway. Of the 60 teams that registered, 50 submitted plans by March 2025.
While taking an oral communication class that spring, I struggled to translate my naturally vibrant personality to formal presentations. My brother joked that my practice videos made me look "like a hostage" rather than the engaging person he knew.
The Payoff
On April 16, 2024, I emailed my supporters after being accepted to UF: "I hope to have one more great idea to pursue besides finance spreadsheets."
Exactly one year later. April 16, 2025.
Retirepreneur was selected as one of 16 semi-finalists for the Big Idea Competition. A perfect full-circle moment.
With Shari by my side, I traveled to Gainesville and delivered my 15-minute presentation followed by a 15-minute Q&A. Though I did not advance to the finals, I conquered my fear and gave it everything I had.
Shari and I stayed an extra day to support the finalists, a gesture that did not go unnoticed. During the awards ceremony, I received the Entrepreneurial Spirit Award and an additional $1,000 grant.
Achievements
Accepted into UF's Master's in Entrepreneurship at age 61
Earned straight A's throughout the entire program. 3.94 GPA.
Won $10,000 in Luby Microgrants. $5,000 at selection, $5,000 more recognizing measurable progress.
Selected as semi-finalist in the Big Idea Competition among 60 teams
Received the Entrepreneurial Spirit Award and $1,000 grant
Secured Retirepreneur.com domain and federal trademark
The Milestone
In December 2025, I walked across the stage at the University of Florida and graduated with my Master's in Entrepreneurship at 63 years old. Shari was there. My family was there. All nine grandchildren were there.
Standing in that cap and gown, I was not thinking about the coursework or the competitions. I was thinking about what it meant to do something hard, something most people my age would never attempt, in front of the people who matter most.
If my grandchildren remember one thing about their grandfather (aka Pappy), I hope it is this: he never stopped building. He never stopped trying. And he never let age be an excuse.
That is the real reason Retirepreneur exists. Not just to help you earn more income, but to show your family, and yourself, what is still possible.
What's Next
Today I am building the Retirepreneur platform and Main Street Ledger, a financial education channel covering small business acquisitions, SBA lending, and franchise ownership. The full build is documented in public through this newsletter.
Still Building Newsletter. Monthly founder's journal, first of every month.
Main Street Ledger. YouTube channel covering SBA lending, franchise research, and business acquisitions.
Blog and Resource Library. Evergreen content on consulting, financial mechanics, and second-act business building.
Podcast. Weekly conversations with professionals building second-act income.
LinkedIn. Daily engagement and professional networking.
The Mindset
I have never been more excited about the future. Shari and I have never been more in love or more enthusiastic about what lies ahead.
Do I still get nervous stepping outside my comfort zone? Absolutely. But I have learned that fear does not dissipate with success. It is a constant companion on the path to growth.
The difference now is that I know I can face it. And so can you.
"I am actually a very humble man and I do not want to ever be seen as bragging, or coming off better than anyone. I have the same fears and uncertainties as anyone else. But once I commit, I am all in."
An Invitation
My story is not exceptional. It is a testament to what is possible when you decide to live with no regrets, when you build and create the best life that makes you happy.
And this is only the beginning.
Retirepreneur: Because retirement is not the end of your story. It is the beginning of your next chapter.
Still Building.
Curt Roese, CPA | Founder, Retirepreneur | M.S. Entrepreneurship, University of Florida