Rich Habits Podcast - Q&A: Retiring at 54, Becoming an Overseas Landlord & Trading Oil Futures

Hosts: Austin Hankwitz & Robert Croak
Date: January 1, 2026

Episode Overview

This special New Year's Q&A episode of the Rich Habits Podcast dives into listener questions on major financial milestones—including early retirement decisions, moving old 401(k)s, starting Roth IRAs as a young hustler, trading oil futures, becoming a landlord overseas, and managing joint finances for newlyweds. Austin and Robert bring both seasoned perspective and energetic, practical advice for individuals at every wealth-building stage, using real listener scenarios to break down complex decisions into actionable steps. Blending encouragement, honest warnings, and fun banter, the duo offers a blueprint for building lasting wealth through smart habits—while sharing personal stories and a few laughs along the way.

Key Discussion Points & Insights

1. Moving an Old 401(k) and Roth IRA Strategy

Listener: Amber S.
Timestamps: 04:05 – 08:41

• Situation: Amber has $164k in a 401(k) from an old employer (recently moved to John Hancock, underperforming), is age 42, married, and wondering about rolling it into a Roth IRA (which would incur ~$34k in taxes) vs. traditional IRA.
• Advice:
  • Roll over to a Traditional IRA for autonomy and investment control (no taxes or penalties).
  • Start maxing out a Roth IRA going forward for future contributions.
  • Avoid the big tax bill from converting the entire amount to a Roth at this stage—better to split: keep the bulk pre-tax and add future dollars after-tax.
  • Only consider Roth conversion if income exceeds the backdoor Roth IRA threshold (>$236k for married filing jointly).
• Framework: Younger workers benefit more from Roth conversions; older workers should keep pre-tax accounts; at 42, stick with a traditional rollover and Roth contributions.
• Memorable Quote:

  “I’m just going to go off vibes on this one. I’m going to say no. Roll it out into a traditional IRA...and then all your contributions going forward are going to go toward a Roth IRA.” – Austin (07:01)

• Robert’s Endorsement:

  “Get that rolled over. No penalties, no fees, just rock and roll…start maxing out that Roth IRA every year. You still have a really strong horizon to build your wealth.” – Robert (08:17)

2. Starting a Roth IRA as a Young Self-Employed Hustler

Listener: Sam J.
Timestamps: 08:41 – 10:33

• Situation: Sam, 19, California, $30,000 in investments, works odd jobs (“dump runs”), $0 in Roth IRA (no taxable income). Should he pay 15.3% self-employment tax to contribute $7k to a Roth?
• Advice:
  • Pay your taxes. “Let’s not do tax evasion.” – Austin (09:25)
  • Set up a single-member LLC for write-offs on expenses, but ensure reported taxable income covers desired Roth contribution.
  • Document and claim self-employment income to make Roth IRA contributions possible.
  • Don’t overdo write-offs or you’ll limit contributable taxable income.
  • Quote:

    “Do things the right way now, set up that foundation the right way and build your wealth along the way and you’ll do just fine.” – Robert (09:57)

3. Trading Oil Futures & Commodities via CFDs

Listener: Farnaz S.
Timestamps: 11:26 – 15:56

• Situation: Curious about oil pricing for 2026, geopolitical concerns, and trading oil via CFDs.
• Advice:
  • Caution against trading CFDs or oil futures unless highly experienced; high volatility, leverage, and time commitment.
  • Commodities are for traders, not “investing” in the long-term sense—lack dividends, business growth, or predictable returns.
  • If you want exposure or to hedge, stick to broad market ETFs or companies in secular growth sectors instead.
  • Memorable Quote:

    “No one invests in commodities. In general, they trade commodities…things don’t pay you dividends. Things don’t report earnings. Things don’t have profits. They’re just things.” – Austin (13:01)

  • Consider opportunity cost—time and energy spent trading vs. consistent long-term investing.
  • Robert adds:

    "You have to ask yourself, is it worth me spending three, four, five hours a day to do this strategy? Or just invest in dollar-cost averaging." – Robert (15:56)

4. Overseas/Large-Distance Landlording

Listener: E.F.
Timestamps: 16:38 – 19:52

• Situation: Listener considers buying/apartment in Dubai with property management handling tenants/maintenance. Is being an overseas or long-distance landlord wise?
• Advice:
  • For beginners: Avoid international real estate—risks due to legal recourse, contracts, and physical distance.
  • If you must go long-distance, stick to domestic properties within a manageable travel distance.
  • Leverage technology for management within the US, but verify property management firms' reliability.
  • Alternative: Consider REITs or real estate ETFs for passive exposure without complexity/headaches.
  • Quote:

    “If you have something, especially out of the country...another level of long distance, I just don’t like it because if something happens, you have to sue somebody...you’re going to have to go to that country.” – Robert (17:19)

  • Austin: Factor in opportunity cost of your time vs. truly passive alternatives.

5. Choosing a Solo 401(k) Provider & Small Business Retirement Strategy

Listener: Shane W.
Timestamps: 20:12 – 22:25

• Situation: Two small businesses, two rental properties, IRA with $190k, spouse with corporate job.
• Advice:
  • Solo 401(k): Great for self-employed with no non-spouse employees; recommend carry.com (C-A-R-R-Y).
  • If possible, consider Mega Backdoor Roth strategy (need a salary, not just self-employment income).
  • Keep maxing out IRAs as well; don’t overcomplicate the approach—simplicity works.
  • Robert:

    “Always, always do that. You want to make sure you get as many benefits as you can every single year...just don’t get too fancy.” – Robert (22:06)

6. Combining Finances as Newlyweds

Listener: Chase M.
Timestamps: 24:22 – 31:28

• Situation: Engaged couple, both 20, still in college, investing in Roth IRAs/brokerage. How to handle finances—joint or separate post-wedding?
• Advice:
  • Max out each Roth IRA—keep accounts separate as individuals, but align on approach for “double-dipping” advantage.
  • Combining finances means being aligned—joint account for household expenses, discuss budget and goals together each month.
  • Maintain some separate accounts for flexibility/hobbies if desired, but prioritize transparency and joint planning.
  • Big Issue: Communicate about financial philosophies before marriage—address differences (spender vs. saver) early.
  • Quote:

    “When I talk about combining finances, I don’t mean so literally...I more mean it in a sense of every month, you and your fiancé or your spouse now sit down and say ‘cool, we are combining.’...We’re on the same page with money, right?” – Austin (25:49)
    “The biggest takeaway…was alignment. But I’m going to back the train up…Before your knee hits the ground, you need to have this [money] conversation.” – Robert (28:14)

  • Avoid forcing a money-obsessed mindset on a more relaxed partner; balance saving/investing with enjoying life.
  • Real story: Spouse with too much control creates resentment; strive for transparency and shared decision-making.

7. Selling a Rental Property at Retirement

Listener: Pia
Timestamps: 31:28 – 36:45

• Situation: Husband, 54, wants to retire early after 25 years as a teacher; they own a rental (now worth $600k, bought at $180k), currently netting ~$2k/mo (condo, $200 HOA, $1,400/mo mortgage at 3%). Should they sell to invest in stocks/bonds, or keep for rental income?
• Advice:
  • Condos appreciate less than single-family homes—selling & investing is a viable, often better, path to generate income, especially with a pension in place.
  • Net proceeds after taxes would be ~$500k; invested at 8–10% could generate $40–50k/year, exceeding current rental yield.
  • Use part of windfall to enjoy retirement, but focus on income-generating investments (ETFs, T-bills, e.g., NEOS funds).
  • Don’t retire with a mortgage if avoidable, but don’t drain investments just to pay off house right away (“don’t be net worth rich but cash poor”).
  • Quote:

    “Real estate doesn’t always go up in value…there are other ways to invest money and make more money with your money. In this instance, I would probably sell it because condos do appreciate less…” – Robert (32:41)

  • Plan for mortgage freedom by 65–70 if possible.

Notable Quotes & Moments

• On Commodities:

  “No one invests in commodities...things don’t pay you dividends. Things don’t report earnings. Things don’t have profits. They’re just things. And the price of that thing goes up or down again as a function of supply and demand for that thing.”
  – Austin, on oil speculation (13:01)

• On Financial Alignment in Marriage:

  “The biggest takeaway from your breakdown...was alignment. But...you need to have this [money] conversation because...one of you might be a spendthrift and one of you might be really frugal and you want to make sure you’re on the same page...”
  – Robert (28:14)

• On the “Get Rich Slow” Philosophy:

  “Just don’t get too fancy. It’s not necessary. Austin laid out the blueprint. Hope this helps and just keep rocking and rolling and do things right.”
  – Robert, on retirement accounts (22:06)

Practical Tools & Resources

• Public.com: Investment platform with customizable “Generated Assets”—create your own indices based on any prompt or strategy.
• Carry.com: Recommended Solo 401(k) provider for entrepreneurs without employees.
• NEOS Funds: ETFs for efficient, monthly income.
• REITs & Real Estate Crowdfunding: For passive real estate exposure.

Summary Table of Major Listener Questions

| Topic | Listener | Timestamp | Hosts’ Key Take | Decision/Action | |------------------------------|------------|------------|-----------------|-------------------------------------------| | Old 401(k) Roll Over | Amber S. | 04:05 | Traditional, not Roth, rollover | Keep bulk in IRA, max Roth IRA moving forward | | Roth IRA for Self-Employed | Sam J. | 08:41 | Pay taxes, LLC | Legitimize income, contribute to Roth IRA | | Trading Oil Futures/CFDs | Farnaz S. | 11:26 | Too risky/complex| Stick to long-term investments and ETFs | | Overseas Landlording | E.F. | 16:38 | Avoid, esp. abroad | Stick to domestic, use REITs for easy exposure | | Solo 401(k) Setup | Shane W. | 20:12 | Carry.com, keep simple | Max solo 401(k), IRA, no extra employees | | Combining Newlywed Finances | Chase M. | 24:22 | Align, communicate | Max each Roth, combine budgets, open dialogue | | Sell Rental for Retirement | Pia | 31:28 | Sell, invest proceeds | Target income-generation, use suitable ETFs |

Final Words & Community Spirit

• The hosts reiterate the power of community, growth mindset for 2026, and plans for the "Rich Habits Rodeo" live event.
• They express gratitude to their listeners, encourage active involvement in the network, and urge listeners to check out resources and previous episodes.

End of Summary