Insurance 360 Podcast
Insurance 360 is made with insurance professionals in mind. I360 explores everything in the world of insurance sales and marketing. Join the team as we explore, insurance selling ideas, marketing trends, insurance carriers, lead generation methods and more!
If you are now, or are considering selling such products as Medicare Advantage, Medicare Supplements, Prescription Drug plans, life insurance, annuities, final expense and ancillary health products such as dental and hospital indemnity, I360 has you covered.
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Latest Episode
Nightmare On Enrollment Street | Insurance 360 Ep. 34 – HALLOWEEN SPECIAL
Insurance 360 Ep. 34
In this second annual Halloween spooktacular episode of Insurance360, hosts Bob and Rob are replaced by Ted Lasso and the Milburn Pennybags (better known as the “Monopoly Man”), who add a Halloween twist to the show.
This episode tackles the challenges and opportunities present during the Annual Enrollment Period (AEP) for insurance agents. Tech troubles, compliance ghosts, commission cuts, vanishing plans; it’s a haunted house out there for agents, but with training, support, and a dash of creativity, you can conquer your fears this AEP season. Packed with some spooky special guests who come to share tips on overcoming tech troubles, embracing new business practices, and the importance of compliance.
Bob and Rob also dive into the history of Monopoly, its unexpected ties to World War II, and the importance of adaptability in both board games and the insurance industry. The episode concludes with encouragement to seize new opportunities and to keep moving forward, even when facing disruptions.t4Insurance are crucial this AEP
Other Episodes
Disruption = Opportunity | How Top Agents are Thriving in 2026
Insurance 360 Ep. 33
AEP, SARs, Commissions & the Future of Medicare Advantage.
In this special AEP edition of the Insurance360 Podcast, Bob and Rob join special guests, Angela Palo, Jeff Palo, and Nick Palo of the Pinnacle Executive team, in a high-level Pinnacle “Cabinet Meeting” to break down the most critical issues agents and agencies are facing in this year’s Annual Enrollment Period (AEP).
📌 Topics include:
- The fallout from SAR notices and non-commissionable plans
- Medicare Advantage disruption and what it means for agents
- Medicare Supplement (MedSupp) & PDP as key options
- How to pivot with hospital indemnity and ancillary products
- The growing importance of C-SNPs as SEP opportunities
- The 2025 Final Rule: HIDE vs. FIDE explained
- Why technology, AI, and Connect4Insurance are crucial this AEP
3 Bobs, 1 Mission: Survive and Thrive in Medicare 2026
Insurance 360 Ep. 32
Join us for a long-awaited episode of Insurance 360 where we recap our recent successful event in Orlando and discuss the rapidly evolving Medicare industry.
Special guest Bobby ‘Medicare Bob’ dives deep into strategies for preparing for the upcoming AEP, the impact of recent industry changes, and how to leverage technology and telesales to manage your book of business.
Learn valuable insights on Medicare Advantage plans, dealing with decommissioned plans, the rise of HMOs, the importance of ancillary products, and more. This episode is packed with tips to help agents grow their business, adapt to changes, and capitalize on new opportunities in 2026. Don’t miss out!
Medicare Advantage Changes:
From PPO’s to Value-Based Care
Insurance 360 Ep. 31
In this episode of Insurance 360, Dr. Shannon Decker scrubs in with hosts Bob and Rob to examine the evolving world of value-based care.
Together, they diagnose the industry’s biggest shifts, from compliance checkups and the anatomy of risk adjustment to the prescription for stronger star ratings. We explore how AI is becoming the new medical assistant, why telehealth is still in good health, and how chronic condition management is the heartbeat of specialized Medicare plans.
Don’t miss this operating-room view of value-based care — the treatment plan for physicians, patients, and the entire healthcare system.
The Tech Evolution is Here! Don’t Get Stuck In The Past
Insurance 360 Ep. 30
In this episode of Insurance 360, Dalton Miller of RetireFlo joins Bob and Rob to explore key insurance trends and challenges.
They cover AEP prep, carrier changes impacting PPO products, and the role of advanced tools like RetireFlo, Connect4Insurance, and Pinnacle’s CRM BOSS. Dalton shares how agents can stay organized with early planning and tech integration, while the episode also spotlights upcoming events and the Pinnacle–RetireFlo partnership supporting agents and agencies.