About 5 Brokerage

Twenty years of hard cases. One AI employee per producer.

Based in Naples, FL, we've spent two decades designing and placing complex insurance for fiduciaries, families, and businesses. 5 Brokerage and the FIVE Agent are how we bring that back office to every producer.

Tuesday · 2:00–3:30 PM

FIVE on shift

You: kitchen table with the Hendersons

Phone face-down. Ninety minutes, fully present.

Meanwhile, FIVE

2:06 PM
APS received for Williams, T. Matched and sent to underwriting.
2:18 PM
Signed HIPAA form from Okafor filed. Requirement cleared.
2:31 PM
Paramed exam confirmed for Patel, Tuesday 8:00 AM at home.
2:47 PM
Labs back for Chen. Last open requirement cleared.
3:12 PM
Commission posted: $18,750 from John Hancock (Johnson, M.).
3:24 PM
Recap drafted for the drive home. One item waiting for your OK.

While you were with the Hendersons

FIVE cleared 3 requirements, confirmed an exam, and posted $18,750 in commission.

Why we built 5B

The best hour of your week is across a kitchen table. Everything else should run itself.

For twenty years we've placed complex cases for producers and fiduciaries. We watched great advisors lose their evenings to portals, spreadsheets, and status calls, and we watched AI companies build software for home offices instead of for them.

So we built the back office we wished our producers had: a brokerage with a FIVE Agent for every agent, comp you can read up front, and the humans behind it when a case gets hard.

Placing complex cases: 20+ years
Contracted and ready: 50+ carriers
You own every client: Your book

Leadership

The people behind FIVE.

Your cases are designed, advocated, and placed by a team with deep carrier relationships, not a call center.

Bill Beynon

Co-Founder

For over 25 years Bill has been at the forefront of estate planning and complex insurance solutions, leading a team of more than 50 professionals serving high-net-worth individuals, businesses, and families.

MDRT Top of the Table and Forum 400 since 2006
Recognized among Forbes’ Top Financial Security Professionals
Named to The Naples 100
Co-author of Wisdom in Wealth

Blaine Ferguson

Co-Founder

A former U.S. Marine Corps officer and helicopter pilot awarded four Air Medals, Blaine retired as a Major in 2001 and now guides the firm’s strategic vision, direction, and oversight.

MDRT Top of the Table, 2010–present
U.S. Senate Military Academy Selection Board (USNA)
Committee member, Red Sox Foundation & MGH Home Base Program

Charles Rainbolt

President

Before joining the firm, Charles was a Case Manager at Potomac Partners and previously Director of Operations at International Media Group.

Vivien Preece

Director of Insurance Services

Vivien was previously Director of New Business at Universal Insurance Services of Florida (an NFP firm) and Director of Risk Management at Forman and Associates, and began her career at Genworth Life.

Devon Preece

Senior Underwriter

Devon’s background spans underwriting and new business at Universal Insurance Services and The Smith Companies, plus hospital experience at Naples Community Hospital.

Tyler Knight

Chief of Staff

Tyler supports the executive team with data analysis, reporting, and account maintenance, and leads firm-wide initiatives to improve operations and optimize the firm’s tech stack.

What we believe

How we work with producers.

Integrity first

Trust is the foundation of every fiduciary relationship. We're transparent about comp, affiliations, and how FIVE handles data.

You own the client

We run the back office. The relationship, and the credit, stay with you.

Advanced markets depth

Premium finance, multi-generational split dollar, and estate equalization, with people who have designed them for decades.

Technology that earns its keep

FIVE exists to give you back hours, not to add another login. If it doesn't save you time, we fix it.

Join 5 Brokerage

Your night shift starts tonight.

Apply in five minutes. We'll review your practice, show you the full comp grid, and have your FIVE Agent working your first case within days.

Apply to join Book a live demo