The Peaks and Valleys of Entrepreneurship

Entrepreneurship isn’t a straight line. It’s a roller coaster — peaks that make you feel unstoppable, and valleys that make you wonder if Publix is hiring (because benefits and free cookies sound pretty good some days).

What matters isn’t avoiding the valleys.

What matters is learning to grow through them and to use them to climb higher.

Early Climb: Creativity + Business.

I started my career in New York in the entertainment industry, working with artists like Billy Joel, Bon Jovi, The Who, Bob Dylan… and yes, even Milli Vanilli.

(And no — they didn’t sing. But they paid on time.)

Those years taught me a truth I still live by:

Creativity and business aren’t enemies — they’re dance partners.

When they work together, you build things that last.

Two Books That Changed My Trajectory

During a career crossroads, my father-in-law recommended a small book: Who Moved My Cheese?

I thought, “What’s a book about mice and cheese going to teach me?”

Turns out: a lot.

The lesson was simple:

1. The world changes.

2. Your life changes.

3. You have to change, too.

Not long after, I read Peaks and Valleys — also by Spencer Johnson.

It taught me perspective: don’t get too high in the highs or too low in the lows. Both are temporary, but the journey is permanent.

Those two books didn’t just inspire me — they pushed me to make significant career decisions and helped me step out of my comfort zone.

The Corporate Peak

I spent years on Wall Street — at AmEx, BNY Mellon, and J.P. Morgan — eventually becoming CFO of TIAA Wealth Management.

We built products that moved markets; one grew to over $52 billion in assets. Our rule was:

“If it can’t generate $100 million, it’s a hobby.”

But even at the peak, something felt off.

I was building great things — for someone else’s dream.

And the message returned:

“Your cheese moved again.”

The Valley

Leaving corporate life wasn’t a leap — it was a free fall.

From billion-dollar budgets to bootstrapping.

From private jets to tech support, asking if I’d tried turning it off and on again.

The valley humbled me.

It tested my confidence, resilience, and patience.

But that’s the truth:

You don’t build resilience on the mountaintop.

You build it in the valley.

Climbing Again: Silicon Beach

When I came to Jacksonville, I saw raw potential everywhere — and no reason this city shouldn’t be a significant innovation hub.

But I also saw a gap in the ecosystem.

Incubators and accelerators do great work, but too often support ends when the program ends. Founders leave energized, then struggle alone.

I also saw pitch events that felt more like reality TV than real help — people playing the “tough investor” role instead of building founders up.

What was missing was what I had in corporate life:

A proper support system — mentors, challengers, cheerleaders, connectors.

So we built Silicon Beach to create that scaffolding around entrepreneurs — through pitch events, partnerships, and real community across founders, universities, students, investors, and leaders.

And my favorite moment never changes:

That spark — when someone realizes,

“I can actually do this.”

The Next Peak: Venture Studio

Now we’re taking the next step.

We’re raising funds to launch Silicon Beach Venture Studio in early 2026.

We’re not an incubator. We’re not an accelerator.

As a venture studio, we build with founders.

We help find customers, shape products, refine pitches, design go-to-market strategies, and guide companies from idea to traction to investment.

Entrepreneurs don’t fail for lack of ideas.

They fail due to a lack of support.

We’re here to change that.

Final Thought

If entrepreneurship has taught me anything, it’s this:

Your last win or failure does not define you — you’re defined by your next move.

Peaks give you confidence.

Valleys give you character.

And the climb is where you become who you’re meant to be.

So wherever you are right now — peak, valley, or somewhere in between — keep going.

Your next peak is closer than you think.