Chuck Winslow Community Ambassador

Chuck Winslow Community Ambassador Contact information, map and directions, contact form, opening hours, services, ratings, photos, videos and announcements from Chuck Winslow Community Ambassador, Medical and health, Indianapolis, IN.

I’m a Community Ambassador dedicated to helping families protect their future — through Medicare guidance, life insurance, trusts, retirement planning, and veteran benefits.

Big day tomorrow.I’ll be sitting down with a local reporter to talk about something that’s been on my heart for a long t...
04/01/2026

Big day tomorrow.

I’ll be sitting down with a local reporter to talk about something that’s been on my heart for a long time — serving our community and giving back in a real way.

We’re also getting ready for an upcoming FREE community meal, and I couldn’t be more excited about it.

Here’s the truth…

A lot of people are going through things you may never see.
And sometimes, the smallest act of kindness can mean everything to someone.

I don’t come from a place where things were always easy.
I’ve seen struggle firsthand — growing up and in my adult life.

So for me, this isn’t just an event…
It’s personal.

It’s about showing people they matter.
It’s about making sure no one feels forgotten.

And it’s about bringing people together — even if just for a meal and a moment.

👉 If you’ve got a heart to serve and want to be part of something meaningful, I’d love to have you join us.

Shoot me a message or drop a comment and I’ll connect with you.

Let’s build something bigger than ourselves.

03/31/2026

🚨 Local Business Owners — Let’s Connect 🚨

I’m making it a priority right now to sit down with local business owners in our community 🤝

Not to sell you anything… but to learn about what you’re currently offering your team and see if there are ways we can strengthen, improve, or add to your benefits — if it makes sense for you.

Part of my new role is working alongside a team that specializes in Group Benefits, and I’m looking to connect the right businesses with the right solutions 💼

But even more important than that…

👉 I want to collaborate with local businesses
👉 Build real relationships
👉 And find ways we can serve our community together

If you own a business, manage a team, or know someone who does — I’d love to connect.

📅 No pressure. No cost. Just a conversation.

Drop a “CONNECT” below or shoot me a message and I’ll reach out personally.

Let’s build something strong in our community 💪

🍷 Join Me & My Great Friends at Rose Senior Living for this FREE Amazing Event! 🍷I’d love for you to come out and join m...
03/30/2026

🍷 Join Me & My Great Friends at Rose Senior Living for this FREE Amazing Event! 🍷

I’d love for you to come out and join me and my great friends at Rose Senior Living, who are hosting us for a wonderful afternoon of wine, food, and great company!

🗓 Thursday, April 2nd
⏰ 3:00 PM – 5:00 PM

We’ll be enjoying a guided wine tasting experience, perfectly paired with delicious bites—from savory selections to sweet treats. It’s a relaxed, fun setting and a great way to spend the afternoon with amazing people.

This is one of those events you don’t want to miss—great atmosphere, great conversations, and even better company.

👉 You MUST RSVP to attend
Comment “WINE” below and I’ll message you personally to reserve your spot.

Spots are limited—don’t wait!

Hope to see you there! 🍷

WEBSITE SOFT LAUNCHHey everyone 👋I’m excited to finally share something I’ve been working on behind the scenes…🌐 My new ...
03/19/2026

WEBSITE SOFT LAUNCH
Hey everyone 👋
I’m excited to finally share something I’ve been working on behind the scenes…
🌐 My new website is live:
👉 ChuckWinslow.com
This has been a passion project of mine—built to be a place where seniors, families, and our community can come to learn, plan, and feel confident about the future.
As many of you know, my mission has always been simple:
🇺🇸 Serve our seniors, veterans, and families
🤝 Be a trusted local resource
📘 Help people understand their options (not just sell something)
On the site, you’ll find information and support around:
✔️ Medicare & Retirement Planning
✔️ Life Insurance & Final Expense Funeral Planning
✔️ Long-Term & Short-Term Care Options
✔️ Legacy & Financial Protection Strategies
⚠️ Quick note (soft launch):
The site is live, but still a work in progress. You may notice a few links, pages, or resources that are still being built out or fine-tuned. More content, tools, and videos are coming soon!
💬 Here’s where I could use your help…
If you check it out, I’d truly appreciate your feedback.
👉 What do you like?
👉 What would you want to see more of?
If you or someone you love has questions about retirement, Medicare, or planning ahead…
📞 Call/Text: 463-204-8050
🌐 Visit: ChuckWinslow.com
My time is always free, and I’m always here to help.
❤️ Thank you for being part of this journey.
Let’s keep building something great for our community.
— Chuck Winslow
Ambassador to Seniors, Veterans & Our Community

Ready to DJ while my seniors drink it up and dance for a few hours!
03/19/2026

Ready to DJ while my seniors drink it up and dance for a few hours!

🎉🍽️ WE’RE GETTING CLOSE!!! 🐣🎉We’re just days away from an incredible night at the 38th Street Library, and I couldn’t be...
03/19/2026

🎉🍽️ WE’RE GETTING CLOSE!!! 🐣🎉

We’re just days away from an incredible night at the 38th Street Library, and I couldn’t be more excited to bring this together for our community ❤️

This is more than just an event…
👉 It’s a night to come together
👉 A night for families
👉 A night where no one goes hungry

🗓 Monday, April 6th
🍽 Free Community Dinner: 5:30 PM – 7:00 PM
🥚 Free Egg Hunt (Kids 12 & under): 7:00 PM – 7:30 PM

Bring your kids, bring your friends, bring your neighbors… or just bring yourself. You are welcome here.

We’ve got great food, fun for the kids, and a whole lot of heart going into this 💛

🙏 And if you’re someone who wants to be part of making this happen…
Want to help? Text (meal) to me at 463-204-8050

Let’s make this something special together.
I’ll see you there 👊

— Chuck Winslow
Local Ambassador to Seniors, Veterans & Our Community
East 38th Street library

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.

Having a great time in   learning new ways to better serve the families and community I’m honored to support!
03/03/2026

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

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

Address

Indianapolis, IN

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Who are we

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Call or text 463-204-8050 we are ready and willing to work hard to earn your business and most of all your respect.