Why I built what I built, and the “what if” that won't leave me alone.
The Plight of the Seller
Most people don't fully understand what it means to build a business over decades. They picture the storefront, the website, the team. What they miss is the weight of it, the years of compounding decisions, the personal capital risked, the holidays sacrificed, the identity slowly fused into the work.
Most of these owners don't have a 401k. They don't have a portfolio of investments quietly accruing in the background. What they have instead is this business that they have poured themselves into. This is the retirement plan. This is the savings account.
And over time, it becomes their identity. They don't know what life even looks like after they close up shop, and it often becomes easier not to think about exit planning, or what their business is worth, or the things they need to do to prepare for an exit, because what comes next, even after a successful outcome, is like looking down a dimly lit pathway into obscurity.
I understand this because I lived through it with my father.
My Dad, Miami, and a Love for Costa Rica
When I was younger, my Dad was a successful entrepreneur. He had built a profitable travel agency based in Miami, along with a tourism operation primarily built around experiences in Central and South America.
In particular, being a Costa Rican immigrant, he loved for people to see the land he grew up in: the beautiful rainforests, volcanoes, and beaches that Costa Rica had to offer.
He was a white-glove type of business owner. He wanted his clients to have a premium experience and to know that he was with them every step of the way. Sometimes he would even travel to the country himself to make sure everything went smoothly. That was his passion. The business and the man were inseparable.
The Diagnosis, and the Slow Goodbye
Then one day he was diagnosed with prostate cancer.
His health deteriorated slowly at first, then more rapidly. He eventually was not able to run his business and was somewhat in denial along the way that things wouldn't return back to normal. That denial is something I now recognize in a lot of owners I meet. It's not weakness. It's love. When something is that intertwined with who you are, admitting you can't keep doing it feels like admitting something much bigger.
By the time he faced the reality that he could no longer run his business effectively, he turned to family and friends to see who might take it over.
I was young, with little business experience, and living on the other coast at the time. And as is common, the next generation is often not willing or not able to take on their parent's business. The lives of the children have usually moved in their own directions by then, different cities, different careers, different dreams. The succession plan that exists only in a parent's heart rarely survives contact with reality.
The World He Didn't Know Existed
He didn't even know there was such a thing as M&A, business brokers, or investment bankers. That was a foreign world to him, meant, in his mind, for much larger enterprises. Boardrooms in New York, not a travel agency in Miami.
So instead, he ended up winding his business down.
I wish I could say this is rare. But sadly, this is far too common. It's the norm. Owners build something reputable, cash-flowing, full of relationships and goodwill, and all of a sudden, for a variety of reasons, they see winding their company down as their only option. The doors close. The phones stop ringing. The employees scatter. The institutional knowledge evaporates. And what remains is a Google listing that says “permanently closed.”
Why I Really Built Iconic
The story I often tell when I talk about why I built Iconic is around the massive opportunity around putting private wealth to work in cash-flow businesses, in building technology solutions that matter. About the silver tsunami. All of that is true. It's the version that fits neatly on a pitch deck.
But the real story is the one that has stuck with me for many, many years. A “what if” scenario that gnaws at me constantly.
What if my Dad would have been able to sell his business? How would that have made his final years easier for him and his family.
What if the people who worked for him could have continued to do so under a new manager, someone willing to build upon the foundation he laid?
What if there had been someone whose job it was to walk into his office, sit across from him, and say: you have built something real, and it is worth something, and there is a path forward that doesn't end with the lights being turned off?
That Is the Work
Iconic exists, in the end, because of a story that never got its better ending. Every owner we work with is, in some quiet way, a chance to write a different version of the one my Dad lived through.
To help owners see what they've built. To help them understand what it's worth. To prepare them for what comes next so the pathway forward feels less dim. And to make sure that what they spent a lifetime creating doesn't just quietly disappear when they're ready, or forced, to step away.
Part of that work is showing owners that exiting does not have to be the end. It can be the beginning of understanding how to start a new chapter. Not the cliche of sipping mai tais on a beach somewhere until the days blur together. Something more meaningful than that. A new purpose. A new problem to solve. A board seat, a nonprofit, a passion project, more time with grandkids, the book they never wrote, the mentorship they never had time to give. And alongside that new chapter, the financial freedom that finally lets them and their families make decisions from a place of choice rather than necessity. That is what a thoughtful exit can unlock. Not an ending, but the first real opening in decades.
That is the work. That is why I built Iconic. And it's the part of the story I think about most.
