What if the hardest day of your life as a parent could also be the most transformative day for your business?
Yesterday, I discovered something that no business book teaches you: The moment you let go of what you love most is the exact moment you step into who you’re meant to become.
I dropped my firstborn at college. Filed trademark paperwork. Cried in a parking lot. Built a website. And somewhere between the tears and the tactical work, I stumbled upon the secret of entrepreneurial parenting that changes everything — for your family AND your company.
This isn’t just another founder’s story about “work-life balance.” This is about the raw, messy truth of building a legacy business while watching your legacy walk away.
The Handshake That Changed Everything: When Entrepreneurial Parenting Gets Real
Yesterday was the very definition of bittersweet.
We moved my firstborn, Cameron, into college. I’m profoundly proud of the young man he’s become, but he’s still my baby — and watching him walk away that last time cracked something open in me.
When it came time for goodbye, I didn’t hug him. Instead, I shook his hand. The same way my own dad did when he dropped me at Yale.
I told him how proud I was. How much I loved him. That he should have the time of his life.
Then, once he was out of view, I sat in the backseat of the car and cried like I haven’t cried in years.
Here’s what nobody tells you about entrepreneurial parenting: The skills that make you a great founder — the ability to release control, trust the process, let things grow beyond you — are the exact same skills that break your heart as a parent.
But they’re also the skills that set everyone free.
The Business Milestones Hidden in Personal Pain
That’s the thing about letting go as growth: Milestones expand us. Cameron stepping into his future forced me to step more fully into mine.
And yesterday, even through the emotional fog, the founder in me kept building. Because that’s what we do. We build through the pain. We create through the chaos. And we find meaning in the motion.
Yesterday’s Business Wins (Between the Tears):
- Trademark Protection for the Future: I submitted proof-of-use for AI Alchemy and AI Alchemist. Not glamorous work, but foundational. These aren’t just names — they’re seeds of ideas that will matter five years from now. Protecting them while processing emotions? That’s building a legacy business in real-time.
- The Regulators Baseball Club Evolution: I polished the RBC blog layout and posted the season schedule. Small tasks? Maybe. But credibility lives in the details. The moment I saw that new design, it felt real — like the kind of organization parents would trust with their own Camerons.
- The Tryouts Page That’s Really a Values Statement: Made serious progress on the RBC Tryouts page. But this isn’t just a registration form. It’s a manifesto to parents: We’re not just building baseball players, we’re building better humans through:
- Hustle
- Effort
- Attitude
- Teamwork
The same values I tried to instill in Cameron. The same ones now walking around a college campus without me.
Work-Life Integration: The Founder’s Reality Nobody Discusses
Most people talk about work-life balance like they’re separate entities. But entrepreneurial parenting taught me something different: They’re the same thing.
Your business is your baby. Your baby becomes an adult. Both require you to:
- Build strong foundations
- Trust the process
- Release control gradually
- Celebrate independence as success (even when it hurts)
Yesterday wasn’t about balancing anything. It was about work-life integration at its most raw and real. Filing trademarks while grieving. Building websites while celebrating. Creating the future while honoring the past.
This is founder vulnerability at its core: Admitting that sometimes your biggest business breakthroughs happen in parking lots, through tears, right after your heart breaks wide open.
The Systems That Save Us: Building a Legacy Business Through Life Transitions
So yes, yesterday was about systems, checklists, and websites. But more than that, it was about perspective.
What Building Through Transitions Teaches You:
The Power of Process When emotions overwhelm, process saves you. Every trademark filed, every webpage updated, every system documented — these aren’t just tasks. They’re anchors that keep you moving forward when everything feels like it’s falling apart.
The Compound Effect of Small Actions That blog layout? It might bring in one more family. That trademark? It might protect millions in future revenue. That tryout page? It might find the next Cameron who needs what we’re building.
The Integration of Identity I’m not a founder OR a father. I’m both, simultaneously, always. And the beautiful mess of entrepreneurial parenting means neither role ever turns off. Cameron walking into his dorm influenced how I wrote that website copy. Filing that trademark influenced how I said goodbye.
Letting Go as Growth: The Ultimate Founder Lesson
Here’s what I learned in that parking lot, tears streaming, laptop open, building through the breaking:
Growth always costs us something, and it always gives us more than we expect.
Cameron stepping into his future isn’t a loss — it’s an expansion. My companies stepping into their next phase isn’t separate from this personal milestone — it’s amplified by it.
The Three Transformations of Letting Go:
- Personal Becomes Professional The emotions of dropping your child at college don’t disappear at the office door. They infuse your work with meaning, urgency, and depth. Every business decision now carries the weight of “What legacy am I building?”
- Vulnerability Becomes Strength Admitting you cried in a parking lot while filing trademark paperwork isn’t weakness. It’s the kind of founder vulnerability that builds real connections, real companies, real impact.
- Endings Become Beginnings Cameron’s childhood ended yesterday. But his adulthood began. My role as his daily guide ended. But my role as his foundation began. The old version of my business ended. But the legacy version began.
The Bittersweet Truth About Business Milestones
Yesterday reminded me why entrepreneurial parenting is the hardest and most rewarding path:
- You build companies while building humans
- You create systems while creating memories
- You protect intellectual property while protecting hearts
- You scale businesses while scaling back control
Bittersweet? Absolutely.
But isn’t that the point? The things worth doing always are.
Your Permission to Feel It All
Maybe you’re reading this in your own parking lot, processing your own goodbye. Maybe you’re trying to build something meaningful while life keeps happening around you. Or maybe you’re wondering if it’s okay to file paperwork through tears.
It is.
In fact, it’s the only way that matters. Building a legacy business isn’t about separating your personal and professional lives. It’s about work-life integration that honors both. It’s about letting the messy, beautiful, painful parts of life inform and improve your work.
And… It’s about understanding that the same courage it takes to let your child go is the courage it takes to let your company grow beyond you.
The Future We’re Building (Together and Apart)
My son is stepping into his future. My companies are stepping into theirs. And in both cases, I’m reminded: The work we put in today — the systems, the culture, the values — is what shapes tomorrow.
Cameron doesn’t need me to pack his lunch anymore. But he carries every lesson, every value, every “I love you” with him. The businesses I’m building don’t need my constant control. But they carry the foundation, the vision, the values forward.
That’s entrepreneurial parenting. That’s building a legacy business. And it is the beautiful, bittersweet balance of building and letting go.
Ready to embrace the messy middle of entrepreneurial parenting?
Join me as I document the real journey of building companies while building humans. Subscribe to see how founder vulnerability, business milestones, and letting go as growth create something bigger than any of us imagined.
Because the best businesses aren’t built in spite of life happening. They’re built because of it.
