Podcast Summary

Podcast: Ready For Retirement
Host: James Conole, CFP®
Episode: This Is What a $10M Retirement Actually Looks Like
Date: January 4, 2026

Episode Overview

In this episode, James Conole, CFP®, dives into the realities of retiring with an eight-figure portfolio. Using a detailed case study, he dispels common myths about “ultra-wealthy” retirements (think yachts and excess) and lays out what it actually means—practically, emotionally, and financially—to transition into retirement with $10 million or more. The analysis covers cash flow, expenses, portfolio withdrawal rates, tax implications, estate and gift planning, and the psychological burdens of significant wealth.

Key Discussion Points and Insights

1. Common Sources of Eight-Figure Retirement Wealth

• Most people with $10M+ in retirement assets didn’t accumulate their wealth through lavish spending or inheritance.
  • Usually comes from:
    • Selling a business
    • Equity compensation in a successful public company
    • Occasionally inheritance, but that’s less typical
  • Quote [00:52]: “People at this level… got there because they grinded. They started a business, ran a business, sold a business and... there’s this windfall that they know can radically transform what life looks like.”

2. Case Study: Roger and Catherine

• Profile:
  • Ages: 62
  • ~ $7M in stock portfolio (from equity comp), additional retirement accounts, and a primary home with a mortgage.
  • Not living lavishly before retirement—focused on wealth accumulation.
• Goals:
  • Retire at 65.
  • Spend $10,000/month ($120K/year), inflating with cost of living.
  • $25,000/year for travel (especially in early “go-go” years, up to age 75).
  • Health care planning before and after Medicare.
  • Collect Social Security at age 70.
• Financial Structure:
  • Still earning salaries for three more years.
  • Mortgage paid off by 2034.
  • Social Security begins at age 70.

3. Cash Flow & Expenses in Retirement

• Transition: Income from salaries stops at 65, then they bridge with portfolio withdrawals until Social Security at 70.

  • Breakdown [05:00]: “So net flows means all of that needs to come from their portfolio… that net flow drops at age 70. And that’s simply because Social Security kicks in.”

• Expenses

  • Adjusted for inflation yearly.
  • Some expenses (like travel, mortgage) are time-limited or decrease over time.
  • Quote [04:21]: “Some of these expenses are adjusted with inflation. Some—like the mortgage—go away, some don’t.”

• Taxes Remain a Factor

  • Federal taxes increase significantly at 75 due to required minimum distributions (RMDs).
  • Importance of tax-efficient withdrawals and planning ahead.

4. Withdrawal Rate & Portfolio Sustainability

• Initial Withdrawal Rate: About 2% of portfolio value before Social Security starts.
• Becomes More Sustainable: Drops below 1% when Social Security kicks in and portfolio grows.
• Impact of RMDs: At age 75, forced IRA withdrawals increase outflows but don’t necessarily reflect needed spending (can be reinvested).
• Projection: By age 95, their liquid investment portfolio could exceed $90 million, not counting their home.
  • Quote [12:45]: “By age 95, they’re expected to have almost $90 million in their liquid portfolio, which by the way does not even factor in any of the value of their home.”

5. Psychology of Wealth and Spending

• Challenge: Transitioning from building wealth to enjoying/spending it purposefully is hard.
  • Many go into retirement unsure how much to "allow" themselves to spend.
  • Quote [02:16]: “A lot of people that have this level of wealth… their first question is, I have no idea how much I can even think about spending in these years.”
• Advice: Don’t default to arbitrary numbers. Instead, start with real-life dreams and values (e.g., family experiences, philanthropy, lifestyle upgrades), then use those to inform spending goals.
  • Explore higher spending scenarios (e.g., increase to $15K/month living, double travel budget) and model sustainability.
  • Quote [17:10]: “Don’t think in terms of $15,000 per month or $12,000 per month. Think in terms of what do you actually want to do… and work backwards.”

6. Investment, Tax, and Estate Planning Implications

• Portfolio Construction:

  • Balance between growth and conservatism based on needs and risk.
  • Consider alternative assets for tax efficiency or added stability.

• Tax Strategies:

  • Roth conversions during “tax planning window” (early retirement years before RMDs or Social Security).
  • Use highly appreciated stock as gifts (more advantageous than giving cash, due to basis step-up and capital gains avoidance).
  • Advanced tactics: Use of donor advised funds for strategic giving and potential tax offsets.
  • Quote [21:13]: “What if we gift a large amount to a donor advised fund? That donor advised fund becomes like our family foundation…”

• Estate and Gifting:

  • Plan to minimize estate taxes and instill family values through giving.
  • Make strategies that sync with overall family legacy goals.

7. The Unique Burdens of Extreme Wealth

• Anxiety Shifts: Less worry about “will I run out of money," more about “how do I not make a big mistake?”

  • Quote [23:46]: “There’s a much greater chance that the anxiety, the burden of having that money and not wanting to make a mistake… That is going to be the main thing that you’re thinking about.”

• Final Encouragement:

  • Spend intentionally on things that matter most—time, experiences, relationships, generosity.
  • Seek help with sophisticated planning to avoid costly mistakes.
  • Vista Private Wealth at Root Financial: Designed for those with $10M+ grappling with these unique challenges.

Memorable Quotes with Timestamps

• “Most people think a $10 million retirement means yachts, first class travel, never having to think about money again. But the reality is that’s not what a $10 million retirement looks like at all.”
  — James Conole [00:00]

• “Their first question is, I have no idea how much I can even think about spending in these years.”
  — James Conole [02:16]

• “By age 95, they’re expected to have almost $90 million in their liquid portfolio…”
  — James Conole [12:45]

• “Don’t spend money wastefully. But we need to make sure that you’re fully spending anything you might want to spend, to give like you want to give, to spend like you want to spend…”
  — James Conole [18:38]

• "There’s a much greater chance that the anxiety, the burden of having that money and not wanting to make a mistake… That is going to be the main thing that you’re thinking about.”
  — James Conole [23:46]

Timestamps for Key Segments

• 00:00–02:10: Common characteristics of $10M+ retirees; case study introduction
• 02:11–06:00: Roger & Catherine’s background, goals, and initial retirement plan
• 06:01–10:00: Cash flow transition, expenses, mortgage payoff, and inflation
• 10:01–12:45: Taxes, RMDs, net portfolio withdrawals, and Social Security timing
• 12:46–16:53: Portfolio sustainability, withdrawal rate analysis, and long-term wealth growth
• 16:54–22:50: Spending beyond basics, philanthropic planning, donor advised funds, and advanced tax tactics
• 22:51–End: The emotional side of wealth; unique burdens; summary & call to intentional planning

Conclusion

James Conole’s detailed walkthrough clarifies that an ultra-high-net-worth retirement is less about endless luxury and more about purposeful living, complex planning, and the emotional responsibility of stewardship. For $10M+ retirees, the greatest challenge is often psychological—ensuring resources are used to deepen life satisfaction and minimize avoidable risks, rather than simply amassing ever-growing balances. Real planning is about aligning money with meaning, not just comfort or status.