298. Ask Tori: Investing and Retirement

Summary of 298. Ask Tori: Investing and Retirement

by Her First $100K

37m•September 8, 2026
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Overview of Her First $100K: “298. Ask Tori: Investing and Retirement”

In this Q&A episode, Tori Dunlap answers listener questions about investing, retirement, mortgage payoff vs. investing, old retirement accounts, and what to do if you’re invested through a high-fee broker like Edward Jones. Her central message is consistent throughout: stay the course, prioritize long-term investing, and avoid letting fear or bad financial advice derail your progress.

Main Topics Covered

Mortgage Payoff vs. Investing

  • Tori says that for most people, investing is the better use of extra cash than paying off a low-interest mortgage early.
  • Her reasoning:
    • Mortgage rates are often lower than expected long-term stock market returns.
    • Time in the market matters more than aggressively eliminating “good debt.”
    • Paying off a mortgage early can feel emotionally satisfying, but it may cost you years of compounding.
  • She draws a clear line between:
    • High-interest debt like credit cards, which should be addressed first
    • Lower-interest debt like mortgages, where investing usually makes more sense

What Retirement Looks Like Logistically

  • Retirement money is not usually pulled out all at once.
  • Tori explains that people should plan years in advance, not just a few months before retiring.
  • Common strategy:
    • Gradually move money into lower-risk vehicles like CDs or other safer accounts
    • Use a CD ladder so funds become available over time
  • She notes that:
    • Pulling everything out at once can create a tax nightmare
    • You generally want your investments to keep growing while you’re transitioning into retirement

Old 401(k)s / 403(b)s After Changing Jobs

  • Tori strongly recommends not leaving retirement money with a former employer.
  • Better options:
    • Roll it into a new employer’s retirement plan
    • Or roll it into an IRA you control
  • Why consolidate?
    • Easier to manage
    • Less risk of losing track of old accounts
    • More control over your investments
  • She also mentions a tool called Capitalize, which can help locate and roll over old accounts.

Getting Out of Edward Jones

  • Tori is blunt: she thinks Edward Jones charges excessive fees and is a poor choice for many investors.
  • If you’re there and want out, she suggests moving your money to one of three paths:
    1. DIY investing platform like Vanguard, Fidelity, or Charles Schwab
    2. Robo-advisor like Betterment, Wealthfront, Acorns, etc.
    3. A guided investing education program like Stock Market School
  • She advises that if there’s an exit fee, it may be worth paying to get your money out of a high-fee situation.

Key Financial Takeaways

1. Don’t change your strategy because the market feels scary

  • Tori says her advice does not change based on elections, recessions, or market volatility.
  • Her core guidance remains:
    • Keep an emergency fund
    • Pay down credit card debt
    • Keep investing consistently

2. Fear is not a financial strategy

  • She pushes back on panic-driven thinking, especially around recessions and political uncertainty.
  • Her message: don’t let fear pause your financial progress.

3. Compound growth is powerful

  • Delaying investing by even 10–15 years can significantly reduce long-term wealth.
  • She emphasizes that starting earlier matters more than trying to “perfect” your debt payoff strategy.

4. High-fee accounts can quietly drain wealth

  • A major theme of the episode is the danger of fees eating into returns.
  • She encourages listeners to regularly check:
    • Account fees
    • Management fees
    • Hidden broker costs

Retirement and Account Management Tips

For retirement withdrawals

  • Plan ahead, ideally 5–10 years before retirement.
  • Use safer vehicles for money you’ll need soon.
  • Don’t assume retirement means liquidating everything immediately.

For Roth IRAs

  • Tori reminds listeners that Roth IRA contributions can be withdrawn penalty-free.
  • Earnings may be subject to penalties if withdrawn before age 59½.

For old employer plans

  • Rollovers are usually better than leaving money behind.
  • Consolidation can reduce confusion and make your finances easier to manage.

Resources Mentioned

  • Free investing workshop: Stock Market Secrets / free stock market workshop
  • Capitalize: Helps find and roll over old retirement accounts
  • Squarespace, Rocket Money, LinkedIn, NetSuite: sponsors mentioned during the episode

Bottom Line

This episode is a practical, no-nonsense guide to handling common investing and retirement dilemmas. Tori’s advice boils down to:

  • Invest early and consistently
  • Don’t let fear or shame control your money decisions
  • Consolidate old accounts
  • Avoid high-fee financial products
  • Plan retirement well in advance