Chuck Winslow Community Ambassador

03/04/2026

Traveling back to Indianapolis, Indiana, with a layover in Fort Lauderdale, Florida.

I'm looking forward to leveraging my expertise to make a positive impact on the individuals I serve.

03/03/2026

Having a great time in learning new ways to better serve the families and community I’m honored to support!

02/24/2026

Excited to be at Rose Senior Living - Carmel today to be their special guest for Karaoke!

02/20/2026

Most parents protect their home.
Most parents protect their car.

Very few protect their child’s future insurability.

In this video, I break down why life insurance for kids is one of the smartest long-term protection strategies families overlook.

If you’re building a legacy — don’t skip this step.

Message me to learn more.

02/19/2026

02/19/2026

🚀 WE’RE EXPANDING

Golden Years Wealth & Legacy Planning is building a small outreach team on the West Side of Indy.
We’re looking for:

📞 Appointment Setters
🚪 Door Knockers

✔ Leads Provided
✔ Structured call sessions
✔ Assigned door knocking areas
✔ Growth opportunity into a full-time Broker / Agent

Call Schedule: • Mondays 6PM–9PM
• Wednesdays 9AM–12PM
📍 Innovation Blvd – West Side Indy

This is a performance-based opportunity.
No hourly cap. Your income reflects your effort.
Veterans and real estate agents between deals encouraged.

If you’re competitive, coachable, and ready to earn…

📲 Call or text 463-204-8050
Chuck Winslow
Golden Years Wealth & Legacy Planning

02/17/2026

🚨 WE’RE EXPANDING 🚨
100% COMMISSION. NO HOURLY. NO CAP.

Golden Years Wealth & Legacy Planning is building a small, hungry outreach team.

We’re looking for:

📞 Appointment Setters
🚪 Door Knockers

🔥 Leads Provided – You do NOT have to find your own.
🔥 Structured call sessions.
🔥 Assigned door knocking areas.
🔥 Real growth into a full-time Broker / Agent.

Call Sessions:
• Mondays 6PM–9PM
• Wednesdays 9AM–12PM

📍 West Side of Indy – Off Innovation Blvd

This is NOT for:
❌ People who need hourly pay
❌ People afraid of rejection
❌ People who need to be babysat

This IS for:
✔ Veterans
✔ Real estate agents between deals
✔ Competitive people
✔ Anyone tired of capped income
✔ Looking for a Side Hustle

If you want performance pay and a real path into the insurance industry…

📲 Call or text 463-204-8050

Chuck Winslow
Golden Years Wealth & Legacy Planning

02/13/2026

🎧🇺🇸 LET’S KICK THIS OFF THE RIGHT WAY! 🇺🇸🎧

I’m honored to be DJing the Campaign Kick-Off for Travis Hankins as he runs for State Senate – District 31 (Fishers, Geist & North Lawrence)!

This is going to be an incredible night of energy, community, and momentum as we launch this campaign the right way.

📍 Launch Fishers
12175 Visionary Way
Fishers, IN 46038

🗓 Wednesday, February 18th
⏰ 6:00 PM (Doors open at 5:30)

Come out, meet Travis, connect with friends and neighbors, and enjoy some great music while we celebrate the future of our community.

Christian | Conservative | Republican 🇺🇸

Let’s pack the room and show up strong!

Tag someone who should be there 👇

02/10/2026

📚 VOLUNTEERS NEEDED 📚
TURNING PAGES BOOK CLUB WITH CHUCK

I’m launching Turning Pages Book Club with Chuck in senior communities and I’m looking for people who love books and love people.

If you are:
• An avid reader
• A current or retired teacher
• A librarian or former librarian
• Or simply someone who enjoys great stories and conversation

…and you’d be willing to donate a little time to your local senior community, I’d love to connect.

This isn’t about teaching or homework.
It’s about conversation, connection, and shared stories.

📖 Help facilitate relaxed book discussions
📖 Help seniors stay engaged and connected
📖 Make a real difference in your community

👉 Interested? Text “BOOK CLUB” to 463-204-8050
I’ll personally follow up with details.

— Chuck Winslow

02/05/2026

📘 NEW for 2026: Medicare Planning Guide

Medicare can be confusing — and every year it seems to change.

I’ve put together a free, easy-to-understand 2026 Medicare Planning Guide to help seniors, caregivers, and those turning 65 better understand:

Medicare Parts A, B, C & D

Medicare Advantage vs. Medicare Supplement

Prescription drug changes for 2026

Important enrollment periods and deadlines

This guide is educational only, written to be clear, readable, and senior-friendly — no pressure, no obligation.

If you or someone you care about is on Medicare (or turning 65 soon), I hope this helps bring a little clarity and confidence.

👉 Download the free guide here:
https://drive.google.com/file/d/1bM6Gj_J9_KpiCjPtFPq86PZXttMCGEjq/view?usp=sharing

—
Chuck Winslow
Local Ambassador to Seniors & Veterans
📞 463-204-8050