From Chaos to Cadence: How My Virtual Assistant Became My Chief of Staff

The Bottleneck of Being a “One-Man Brand”

For more than a decade, I tried to juggle everything — emcee gigs, entrepreneurship, entertainment, email. Being the personality is what I get paid for, but the piles of logistics and admin kept me from actually showing up as me.

I hired interns, assistants, and eager young professionals across Greenville. They had talent and enthusiasm, but never the time or systems to handle the swirl that is JDew Productions, One Voice, and The Cash Compound. Each brand, each appearance, each client came with a new inbox, a new schedule, a new round of, “Hey, did we ever reply to that?”

And there are only so many hours in a day.

I told myself I just hadn’t met the right person yet. But truthfully, I couldn’t imagine an assistant who wasn’t sitting right across from me. I get energy from people in the room. I couldn’t see how a virtual assistant could possibly match my rhythm or understand my chaos.

Then the flood came.

The Turning Point

Late September 2024 — Hurricane Helene hit hard. My car flooded. My community lost power/internet. My energy drained. My business partners flew off to Germany for a conference, leaving me caring for nephews and a niece, fighting exhaustion, and trying to keep the plates spinning.

In the middle of that storm, I finally said, enough.

I opened onlinejobs.ph, the platform my coach Tim Joiner had told me about, and started searching for a virtual assistant. I didn’t know what half the filters meant, so I just set everything to the highest level possible. Only one candidate showed up.

Tim laughed. “You’re too specific! You should have twenty to choose from!”

But that one candidate turned out to be the one.

Her name was Rye.

She thought my short, one-line email was spam. She was looking for her first virtual-assistant role after leaving her on-site job in the Philippines. Her husband, a seafarer, worked the cargo ships off America’s East Coast. She wanted to work from home, spend time with her dogs, and build something lasting.

I gave her two small projects. She delivered them perfectly in two days. I was sick, tired, and desperate for help. I decided to stick with her.

God’s mercy, plain and simple.

The Transformation of a Year

What Rye does isn’t just task execution — it’s thinking. She knows how I process information, how I like it presented, and how to translate my stream of voice memos, screenshots, and texts into structured systems: email, calendars, Slack, High Level.

Every morning at 8 a.m. Eastern (8 p.m. her time), we meet for our Cadence of Accountability.

We review yesterday’s progress, new tasks, overnight ideas, and my “text-bank” — that wild collection of unread DMs and messages that pile up from clients and collaborators. She keeps me focused, prioritized, and moving forward.

Over the months, Rye evolved:

• Virtual Assistant → Executive Assistant — She started handling not just business logistics but also personal responsibilities, from bill reminders to family scheduling.

• Executive Assistant → Chief of Staff — She began managing other contractors around the world: video editors, marketing specialists, and automation pros. Everything now funnels through her.

She even communicates with our global team in their native tongue — faster, clearer, better. She saves me time, eliminates redundancy, and keeps projects humming.

The biggest surprise? Her dedication to the mission. There are people thousands of miles away who care about your vision as much as you do.

The Ripple Effect

Because of Rye, I can finally show up where it matters most — to my clients, my community, and my kids.

She’s helped me reclaim hours, not just for productivity, but for presence.

I can leave the office earlier. I do car line two days a week now, picking up my kids from school with full focus and a clear mind. That’s priceless.

With her managing archives, emails, follow-ups, and file systems, I get to do more of the right things: the high-value work that pays well and fills me with joy.

If she disappeared tomorrow, sure — it’d hurt. But thanks to the systems we’ve built together, much of what she does lives in SOPs (Standard Operating Procedures). That’s part of her brilliance: she’s made the help she provides repeatable.

Gratitude and Acknowledgment

Rye, I’m thankful for you.

Thank you for your dedication to our long-term goals. Thank you for believing in this mission — and in your own. I admire your dream of building a pet shelter for stray dogs in the Philippines. I believe in that vision as much as you’ve believed in mine.

Because of you, I feel safe. Supported. Heard. You ask clarifying questions instead of assuming. You remember details from months ago. You think ahead.

You’ve made me better — not just more productive, but more present.

On her birthday in September, JDew and AI teamed up to create this song for Rye. It’s a banger!

Growth and Guidance

This year has been shaped by ideas from Dan Sullivan and Dr. Benjamin Hardy (Who Not How, The Gap and the Gain, 10x Is Easier Than 2x), by the strategies of Dan Martell (Buy Back Your Time), and by the mentorship of Tim Joiner, along with the camaraderie of my brothers in business, Jonah and Will.

These books and relationships taught me that the secret isn’t doing more — it’s finding the who that lets you focus on what matters most. Rye has been my “who.”

If you’re an entrepreneur drowning in details, my advice is simple:

Start before you’re ready.

Find good people.

Keep looking until you do.

And build SOPs so your outcomes are clear even when your calendar isn’t.

Lead with outcomes, not orders.

Hire thinkers, not doers.

Empower them to help you win.

The Big Picture

This year has changed everything for me.

Rye isn’t just part of my business — she’s part of my system, part of my sanity, and part of my story.

Here’s to another hundred years of partnership, purpose, and progress.

Thank you, Rye.

Thank you for helping me buy back my time — and build a life worth showing up for.