Podcast Summary: "Maximize Our Assets and Optimize Our Taxes"

Jill on Money with Jill Schlesinger – December 23, 2025
Host: Jill Schlesinger, CFP®
Episode Focus: Financial planning strategies for a high-earning mid-50s couple looking toward retirement, optimizing their assets, and handling tax implications.

Episode Overview

This episode centers on a listener call-in from Dave in North Carolina, who, with his wife, is navigating the complexities of retirement planning, asset diversification, and tax optimization. Dave’s questions span from handling leftover 529 college savings funds, managing concentrated company stock, and reconsidering his relationship with his financial advisor. Jill Schlesinger and her producer Mark provide actionable insights and reassurance, helping Dave streamline and strengthen his financial future, while keeping their advice jargon-free and pragmatic.

Key Discussion Points & Insights

1. Listener Profile & Retirement Outlook

• Dave & Wife: Mid-50s, two financially independent sons in their 20s ([03:00])
• Income: Combined ~$350,000/year, variably dropping as wife winds down self-employment ([04:27])
• Planned Retirement Age: Around 65 for Dave; wife, a few years older, moving part-time ([03:47])
• Spending: $11,000–$12,000/month baseline, up to $13,000–$14,000/month with travel ([10:27])

2. Assets Overview

• Retirement Accounts:
  • Dave: ~$1.7M in traditional 401(k) ([05:11])
  • Wife: ~$650K across SEP IRA & individual 401(k) ([05:13])
  • Additional IRAs and Roth IRAs for both ([05:36])
• Brokerage Accounts: ~$1M in mutual funds ([06:16])
• Company Stock: ~$1.5M, largely through ESPP, largely unrealized gains ([06:28])
• Savings: ~$450,000 in high-yield savings ([07:25])

3. Real Estate Holdings

• Primary Residence: Worth $650K, $120K mortgage at 3% ([07:46], [07:52])
• Rental Property: Also worth $650K, $235K mortgage, 3% rate, historically $10K/year net cash flow ([08:11], [08:45])
• Additional Properties:
  • Shares a beach property (his share: $400K, no debt) ([09:16])
  • Mountain land ($100K), undeveloped ([09:26])

4. 529 Plan & College Savings

• Issue: $105K left in 529 for son who didn’t attend college ([17:06])
• Solution:
  • Annual Roth IRA rollover for son up to $35K ($7K/year), per new laws ([17:12]–[17:34])
  • Remaining funds: Pay tax & 10% penalty to withdraw for non-educational uses, possibly gift to son ([19:26]–[19:40])

5. Tax & Concentration Risk

• Significant Company Stock:
  • Jill warns on over-concentration and urges gradual diversification, mindful of tax implications ([13:17], [14:53])
  • Recommends engaging a fee-only advisor or good accountant for efficient unwinding strategies ([15:53])
• Tax Situation:
  • Dave’s income and dividends keep him in the 24% tax bracket ([12:23])
  • Roth 401(k) and contribution changes for future: Both Jill and Mark recommend moving all retirement contributions to Roth going forward ([21:12]–[21:18])

6. Financial Advisor Relationship & DIY Investing

• Complication: Dave experiences frustration with portfolio complexity and syncing with Quicken ([14:21]–[14:53])
• Advice:
  • If a financial advisor makes things more complicated, consider a simpler, hourly model for planning or move to a DIY model focused on indexing ([15:53]–[16:36])
  • Reassurance: “No financial advisor should be making your life more complicated. It should be less complicated.” — Jill ([14:53])

7. Estate Planning

• Status: Documents need an update; current ones are ~5 years old ([19:55])
• Advice: Refresh estate documents to reflect sons’ maturity and ensure assets are well protected ([19:58]–[20:02])

Notable Quotes & Memorable Moments

• On Financial Independence of Sons:

  • Jill: “First of all, congratulations on having two sons in their 20s who are financially independent. I feel like… that seems like the most miraculous thing of all right now.” ([04:06])

• On Over-Concentration:

  • Jill: “Your biggest risk is concentration in the company… There are people who can help you manage that, either just bite the bullet, sell some every year.” ([13:17])

• On Advisor Complications:

  • Jill: “No financial advisor should be making your life more complicated. It should be less complicated.” ([14:53])

• On Switching to Roth:

  • Jill: “Yeah, I’m going Roth. Mark, aren’t you going all Roth 100%?”
  • Mark: “Especially if you’re going to be there for another 10 years. Absolutely.” ([21:12]–[21:18])

• On Time Horizon for Retirement:

  • Mark: “I don’t even think you need 10 years, but if you want to do 10 years, knock yourself out.” ([13:13])

• On Life Satisfaction:

  • Jill: “Give yourself permission. Once it stops being fun, you will not need to be doing this… You have plenty of money. If it’s not fun, you can stop.” ([21:44])

Key Timestamps

• [02:58] Listener Dave introduces himself & outlines family structure
• [04:27] Income and transition plans as wife winds down work
• [05:11] Breakdown of retirement account balances
• [06:16] Brokerage & company stock detailed
• [07:25] Savings accounts and liquidity
• [07:44] Real estate holdings and mortgages
• [08:45] Rental property cash flow
• [09:16] Additional property—beach and mountain details
• [10:27] Monthly spending breakdown
• [11:54] Dividends and tax bracket
• [13:13] Discussion: Is 10 years to retirement necessary?
• [14:53] Complications with advisor and desire for simplification
• [17:06] 529 plan specifics and Roth rollover solution
• [19:26] Tax treatment of 529 withdrawals
• [19:55] Estate planning reminder
• [21:12]–[21:18] Switching all contributions to Roth

Actionable Takeaways

• Diversify concentrated positions (especially company stock), with careful tax management
• Reevaluate advisor relationships if complexity or costs are disproportionate
• Utilize new 529-to-Roth IRA rollover options for leftover college savings
• Switch new retirement contributions to Roth for post-tax growth
• Refresh estate planning documents to reflect current wishes and asset levels

Episode Tone & Style

Jill’s signature approach is direct, warm, and no-nonsense, delivering complex advice in accessible language. The conversation is upbeat, supportive, and pragmatic, with gentle humor woven throughout.

For More or to Ask a Question

Listeners can submit questions via jillonmoney.com. Jill highlights the importance of seeking help before making big moves, especially when it comes to taxes and asset allocation.

This summary covers all major topics, actionable advice, and memorable moments for listeners seeking to maximize their own assets and optimize their taxes, especially if they see themselves in Dave’s financial shoes.