I Cried the Whole Ride Home
A childhood memory that changed how I think about wealth
Hi, I’m Chris. I’ve spent the last 25 years building wealth through real estate, business, and hard lessons most people don’t talk about. Here, I share what actually works - how to build wealth, think differently about money, and live a truly rich life.
As a kid, we took one vacation a year, always in the summer. We piled into the car and drove from Pittsburgh to visit my aunt, uncle, and cousins in New Jersey. I got to see the Jersey Shore, which felt magical to a landlocked kid. The ocean felt endless, powerful, alive.
But it only happened once a year, and I still remember staring out the car window on the ride home, tears in my eyes, wishing it didn’t have to end.
Two other trips stand out clearly from my whole childhood: a drive to Niagara Falls and a flight to Disney World. That Disney trip felt monumental. Months of anticipation. I saved every dime and quarter I could find and remember holding $40 in actual quarters, which felt like a fortune at the time. I bought a Goofy hat with an oversized bill and spent the rest on a Mickey Mouse sweatshirt. I loved those things for years, not because they were special objects, but because they were proof. Proof that the trip happened. Proof that the memory was real.
Most of what I remember now lives in photos. Back then, photos lived on rolls of film. You took the picture and hoped for the best, then found out three weeks later someone had blinked.
That Disney trip shaped something in me, though not in the way you might expect. I didn’t grow up wishing my parents had done more. I grew up knowing how much those moments mattered. That awareness turned into a quiet value that now runs through our family. I want my kids to experience more of the world than I did, not because my childhood was lacking, but because exposure expands perspective, and perspective changes how you move through life. Today, that’s a big part of why I love to travel and why I love giving my boys adventures, letting them see new places, different cultures, different ways of living.
The Travel Bug Takes Hold
The travel bug really hit in high school. My mom had worked her way up to become a sales manager at a financial services company and traveled all over the country visiting her sales reps. A few times a year, she took me with her. New airports. New cities. New perspectives and great adventures with my mom. Somewhere in those trips, a quiet belief took root: one day, I want to see more of the world.
My first real adult trip came after college, when one of my best friends and I spent three weeks backpacking across Europe. We stayed in the cheapest hostels we could find. One night, we slept in a stranger’s attic, which was long before Airbnb, back when that actually felt strange. We had no money, so we made it work.
Contrast that with our recent trip to Europe with Jana and the boys. I’m fairly confident we spent more per day on that trip than I spent on the entire three-week backpacking adventure, twenty-five years apart. Both trips were incredible. At 23, I didn’t mind standing in line for hours to save a few dollars. At 49, we paid to skip the lines, and it mattered. We saw more in our first day in Rome than I saw in several days on that first trip, not because the city changed, but because we eliminated hours of waiting. We traded money for time, energy, and presence. Even the food told the story: French fries from McDonald’s back then, actual French food this time.
Money didn’t make the experience meaningful; it removed friction so the experience could be fully lived.
Experiences Don’t Require a Passport
But here’s what I’ve learned about experiences over time: they don't require a passport, and many times they don't even require leaving the house.
When my boys were little, they were obsessed with camo. And I mean fully committed, head-to-toe camo, every chance they got. So I joined them. That became our weekend morning routine: getting dressed in full camouflage and heading out to hide in the woods. The detail that makes this story is that we lived on a golf course, and our backyard bordered a fairway. So on weekend mornings, I’d be out there in the trees in full camo with my boys while my friends and neighbors were playing their rounds and walking right past us. I’m sure some of them thought I was losing my mind. But I was just loving life with my boys, fully present in something that mattered to them because it did. Those mornings weren’t expensive. They weren’t planned. They were just ours.
A meaningful experience can be a family movie night, a hike in the woods, a long walk with nowhere to be, or a board game that runs way past bedtime. What matters isn’t scale; it’s disruption. Too many of us live on autopilot: wake up, work, dinner, screens, bed, repeat. Days blur together, not because life is moving too fast, but because nothing is interrupting the routine. Experiences create contrast. They break the pattern. They force presence.
The Three Layers of Every Great Experience
There are three things I love about travel, and honestly, about most meaningful pursuits in life.
First, having something to look forward to. Anticipation is powerful. It pulls us forward and gives ordinary days a sense of direction.
Second, the experience itself, the trip, the moment, the presence. The reality is that the experience rarely matches the fantasy perfectly, and that’s okay. Growth happens on the journey, and growth equals happiness.
Third, the memory dividends. Long after the trip ends, the experience keeps paying you back through stories, through photos, through moments when you remember who you were and who you were with.
My wife makes printed photo books from our trips and leaves them around the house. Every now and then, on some random weekday, I’ll pick one up and flip through it. In a few minutes, I’m back there: remembering conversations, reliving small moments, feeling grateful all over again. Vacations aren’t an escape from life. They’re an investment in your family’s memory bank, and the dividends show up years later when a photo sparks a story or a moment gets passed down again.
That’s why I love printing photo books from our trips. They aren’t decorations. They’re portals. And these three things aren’t unique to travel. They’re true of anything meaningful: building something, chasing a goal, raising kids, creating a life aligned with your values.
The Real Reason We Build Wealth
As we age, there will be things we can no longer do the way we once did them. Energy changes. Bodies change. Seasons change. But memories remain. And the memories we create become the stories our families tell. They become part of who our kids believe they are. They shape what feels normal, what feels possible.
That’s why we don’t build wealth to escape our past; we build it to expand the experiences we pass forward. Because true wealth, in money, mindset, and meaning, is built through small, consistent decisions that compound over time.
Your Turn + Start Bold
What experiences shaped you growing up, both the ones you had and the ones you wished for? Where might money be able to remove friction from your life right now? What memories are you intentionally building this season?
Start small. Plan one experience you can look forward to. Be fully present when it happens. Capture it in a way you’ll revisit later. That’s how memory dividends compound.
Why We Build Wealth
At BOLD Wealth, we believe money is not the goal. It’s a tool. We build financial wealth not for status or scorekeeping, but to use it as fuel for the parts of life that matter most: family, growth, health, contribution, joy. That’s what it means to minor in money and major in life.