7-19-25 Candid Coffee - Retirement Blueprint

If you fail to plan, you plan to fail in retirement. Richard Rosso and Jonathan Penn address the thorny questions around preparing for retirement.

INTRO
3:55 Retirement is Qualitative: New Retirement Mentality
8:00 The Pre-Retirement Blueprint Agenda
9:15 What to Do for a Living in Retirement
11:00 Our Right Lane Strategy: Variable assets
13:15 The Impact of Large Losses in Retirement
16:45 The Blueprint Strategy
18:20 Begin a Formal Retirement-Planning Exercise
23:00 Taking Social Security Properly
26:30 - Medicare: Know Your Choices & Enrollment Periods
31:00 Mind the Gap in Medigap
32:00 Higher-earning vs lower-earning spouse
35:30 Is initial enrollment period a similar window around your retirement date? (Stan Stinson)
40:31 Max Out Your Health Savings Account
42:00 What Should Asset Allocation Look Like 5-years from Retirement?
44:45 Expenses in Retirement - Five Must-see Charts for Retirement Distributions
46:35 Chart #1: Valuation Levels Are Extremes
47:30 Chart #2: Stocks are Expensive
48:50 Chart #3: Where You Retire in a Market Cycle is Luck
49:10 Chart #4: Never Doubt "Regression to the Mean"
49:50 Chart #5 Bear Markets Occur 40% of the Time
52:10 Consider Housing in Retirement
54:50 Long Term Care Costs
56:45 Why Buy & Hold is a Flawed Theory
58:20 Risk Management is Achievable
1:00:45 The Math of Loss
1:02:00 The Need for a Comprehensive Financial Plan
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