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September 27, 2025 • 51 mins

In this episode of Work, Time & Effort, Chris welcomes back friend and guest Patrick Highland, who not only brings the energy from the sports world but also offers critical insights into something even more personal for many: navigating Medicare.

With Medicare enrollment season right around the corner, Patrick breaks down what most people find confusing — Medicare Supplements, Advantage Plans (HMO & PPO), Part B premiums, and how to truly tailor your healthcare coverage to your life and budget. Whether you’re turning 65 soon, helping a loved one enroll, or just want to save hundreds per month on your current plan, this conversation delivers real value.

You’ll hear:

  • The three tiers of Medicare coverage — from “Cadillac” plans to value-focused options

  • Why choosing the right doctor network matters more than perks like free gym memberships

  • How Patrick saved one client $100/month with a better-fit plan

  • Why October 15 – December 7 is your golden window to make changes

  • The risks of going uninsured — and why some decisions can cost you thousands

  • Tips for staying healthy in retirement and how your plan can help

It’s an informative, eye-opening, and surprisingly entertaining look at the real cost of healthcare — and how to take control of it.

📌 Whether you’re in Sarasota, Bradenton, Tampa or anywhere in Florida — this episode is for you.

Watchdog on Wallstreet: https://watchdogonwallstreet.com/

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