Episode 7 — Being Yourself Is Less Risky Than You Think

What this episode is about:
Why leaning into who you really are isn’t reckless — and how authenticity compounds trust, relationships, and long-term success.

Most people think being themselves in business is risky.

They think standing out is risky.
They think showing personality is risky.
They think being different is risky.

My experience has been the opposite.

Trying to be someone else is far riskier.

There was a moment in a boardroom at Aloha Petroleum that crystallized this lesson for me.

I was sitting at a long, polished conference table — the kind you expect in a major petroleum company.

Across from me was Butch Galdeira, a senior executive at the time.

My brother Joe was next to me.

We were already working with Aloha on pump-top advertising, and I was walking through a PowerPoint I had made.

Halfway through, I could feel it.

The slides were fine.
The message was fine.

But it felt stale.

I hesitated.

This would be the first time I had ever rapped in a boardroom — especially at a company of this scale. It could have gone sideways fast.

But a friend inside the organization had told me earlier, “You need to meet Butch! You guys will get along.”

That gave me just enough of a safe space to trust my instincts.

I’ve always had a tendency to be bold — not in an offensive or intrusive way, but in my own way.

Positivity, friendliness, and a little hip‑hop entrepreneurial edge.

I’ve always believed in asking for forgiveness instead of permission — when the moment is right.

So I read the room.

It was just the three of us.
No audience.
No ego.

I asked Butch if it would be okay if I kicked a rap.

He said, “Go ahead.”

I started with:
“We started at the pump, now it’s time to pump it up.”

And then I went straight into a verse from my song “Remnants.”

When I finished, Butch looked at me and said:

“This is the best meeting I’ve had all year!”

That meeting didn’t just lead to a deal.
It led to a real relationship.

What makes that moment even more meaningful in hindsight is where Butch is today.

He went on to become the President of Diamond Bakery — one of Hawaii’s most iconic brands, with over 100 years of history.

The leaders who recognize authenticity, creativity, and conviction tend to rise.

And the relationships built when you’re being yourself don’t just last — they compound.

For a long time, though, I didn’t fully lean into that side of myself.

I’ve always been a good communicator, but I held back my hip‑hop side.

Even when I launched my podcast in November 2019, I was more sanitized than I needed to be.

My first episodes were with friends from Entrepreneurs’ Organization (EO), including Juno Chung.

EO is full of serious operators, and at first I felt like I needed to live up to a certain “professional” standard.

But the more I got to know everyone, the clearer it became:

Everyone was unique.
Everyone stood out.
That’s why they were leaders.

I realized I didn’t need to blend in.

In Hawaii especially, I dressed the part — Aloha shirts, slacks, leather shoes — looking like I could be a lawyer or executive downtown.

I still dress well today, but now my long‑sleeve Aloha shirts stand out. That’s my uniform.

I can wear it anywhere — work, court, church, weddings, funerals.  (Yes, I go to all of those… but that’s a story for a different time)

What I was really holding back wasn’t how I dressed, it was my voice.
My art.
My hip‑hop identity.

Rap wasn’t mainstream in Hawaii when I was younger.

The culture leaned more Jawaiian and Reggae, or the executives we’re too old to appreciate hip hop.

But now, at 43, I’ve come into my own.

No one is watching you as closely as you think.
Everyone is too busy worrying about themselves.

If a young entrepreneur asked me how to be themselves without being reckless, I’d say this:

Know the room.
Understand consequences.
Think long‑term.

Authenticity doesn’t mean offending people or being careless.

Wisdom matters.

But don’t suppress who you are.

Because the biggest risk in business isn’t being yourself —
it’s trying to be somebody else.

You can’t keep up the act forever.

You can only be second‑best at being someone else.
But you can be world‑class at being you.



If you’ve read this far, you might enjoy my music too.
Check it out at https://ctzns.co