Rich Habits Podcast — Q&A: Separating From Active Duty, Buying Airbnbs To Lower My Taxes, & Living With My Girlfriend

Hosted by Austin Hankwitz and Robert Croak
Date: August 21, 2025

Episode Overview

In this engaging Q&A episode, hosts Austin Hankwitz and Robert Croak answer real listeners' financial questions—ranging from relationship-based money decisions, optimizing debt management, and choosing investment strategies, to leveraging real estate for tax advantages. The conversation is candid, practical, and occasionally direct, as both hosts draw from personal experience and their distinct perspectives—Robert as a decamillionaire business veteran and Austin as a millennial entrepreneur.
Theme: Helping listeners implement "rich habits" through honest, scenario-based financial guidance that demystifies the journey to financial independence.

Key Segments & Insights

1. Living with a Girlfriend, Shared Expenses, and the Mortgage (03:06)

Question from Derek J.:
Should Derek reinvest the $1,650/month his girlfriend pays toward the mortgage to pay it off faster, or should he invest it elsewhere?

• Austin’s Advice (03:40):

  • Caution with cohabiting finances:
    "This is your girlfriend, right? You guys are not fiancé, not married... You guys are roommates. Until you’re married, you should be saying 'I have,' 'she has,' not 'we have.'"
    (04:00)
  • Do not combine finances prematurely.
    "Do not combine your incomes until you are married. Robert and I have seen it 100 times... It’s a terrible situation." (04:23)
  • Treat her payments as you would any roommate's.

• Robert’s Two Approaches (05:21):

  • Option 1: Pay down the mortgage if the interest rate is high (6.75%+).
  • Option 2: Preferable to invest the cash into index funds and ETFs unless the mortgage rate is high.
  • "I would probably rather see you put the money building up your base, building up your investments, and just paying the normal payments on the house." (06:25)

• Austin on Investment Opportunity (06:47):

  • "The Nasdaq is up just over 10% year to date… If you used money to pay down that mortgage, you would be leaving money on the table..."
  • If aggressively paying off the mortgage, maintain investment contributions in parallel.

2. Should I Use My Cash to Pay Off Student Loans? (07:41)

Question from Mike (07:41):
At age 40, Mike asks: Should I use my $57,000 in liquid cash to pay off $57,000 of student loans?

• Austin’s Framework (08:15):

  • If you have as much already invested (Mike has $89K in a 401(k)), using cash to pay off loans is OK.
  • Unlock future investing power:
    "Now you will free up a $1,134/month payment... Use that to invest, not lifestyle creep." (09:41)
  • "You will be a multimillionaire in retirement if you follow this plan." (11:58)

• Robert’s Encouragement (10:40):

  • "Mike, welcome to the party… You’re not late. You have plenty of years ahead to build wealth."
  • "You can't out-invest high interest debt... We always want the arbitrage of our money going in our favor."
  • Set up auto-investing so it's consistent and not consumed by lifestyle inflation. (11:49)

3. Investing at All-Time Highs—Should I Wait? (11:58)

Question from Eric G. (11:58):
Bought stocks and crypto at/near all-time highs. Did I make a mistake?

• Robert’s Long-Term Mindset (12:58):

  • Don't focus on finding a "deal" or worry about buying at all-time highs for established companies.
  • "I don't care what the stock price is, I care about where I believe it's going in three to five years." (13:36)
  • "I've bought Nvidia, Palantir... Amazon, near or at all time highs for years because I've been dollar cost averaging..." (13:55)

• Austin’s Data-Driven Reassurance (14:22):

  • "Bears sound smart, bulls make money." (14:23)
  • Investing at all-time highs has historically outperformed other entry points (shows S&P data since 1989).
  • "All-time highs are bullish. There's nothing bearish about an all-time high... The key: Have a long investment horizon.” (15:54)

• Robert’s Cautionary Note (16:20):

  • Avoid new, hyped “penny stocks” at all-time highs; the strategy is for longstanding, quality companies.

4. Separating From Active-Duty Military vs. Staying for the Pension (17:02)

Question from Brendan B. (17:02):
At a career crossroads: Should I stay six more years for a military pension, or leave for higher earnings in the private sector?

• Robert’s Perspective (18:32):

  • Leaning toward private sector for higher (and safer) earnings potential; relates personal experience of a friend lost close to retirement.
  • “You would be better off financially in the private sector because you'd be making more money and be able to invest it more as long as you stay consistent.” (19:23)
  • Pension = safer, but private sector = more potential wealth and personal safety.

• Austin’s Math Breakdown (19:51):

  • Compares pension to $1.3M invested for a 4% withdrawal—frames opportunity cost.
  • By leaving, with higher salaries and strategic investing, Brendan could build up more than the pension's value (using rule of 72 for market doubling).
  • "Your $52,000/year will not grow exponentially. But invested money can, and could be inherited by your family." (21:23)
  • On legacy: "When you die, your spouse, your children… they might not get $52,000/yr, but they will get a $4M inheritance..." (21:40)
  • Key Takeaway: Math suggests the private sector wins—if disciplined with saving and investing.

5. Should I Sell a Paid-Off Rental to Diversify? (22:37)

Question from Ross C. (22:37):
Should Ross and wife sell a paid-off townhome (~$400K value) to invest elsewhere or buy more real estate?

• Robert on Diversification (23:52):

  • "I believe you're very heavy in real estate... I'd like to see you migrate some money into a more diversified portfolio." (23:59)
  • Suggests selling, investing proceeds in precious metals, index funds, crypto for balance.

• Austin on Execution (25:03):

  • Take advantage of capital gains tax exclusion; roll profits into markets (VOO, QQQ, etc.).
  • "You're not going to go buy $350,000 on day one... Take 3, 6, up to 9 months to dollar cost average in." (27:40)
  • Selling rental (with adequate return) often outperforms holding, especially if you've already built real estate wealth elsewhere.

6. Entering Real Estate for Tax Strategy, ARBNB, and Bonus Depreciation (28:21)

Question from Dr. K.R. (28:21):
Physician earning W-2 income, considering short-term rental/LLC for tax benefits: thoughts and pitfalls?

• Robert’s Warnings and Recommendations (30:04):

  • "It's not what you make, it's what you keep, and this strategy helps you keep more."
  • Urges caution and professional advice: “Do NOT do it alone... Find a consultant or someone that can help you and go from there.” (31:32)
  • Confirm real estate professional participation and understand recent legislative changes.

• Austin on Reality Checks (31:55):

  • Recommends Michael Elefante’s consulting as a resource.
  • Cites real-world examples of people losing money due to unprofitable Airbnbs.
  • "People think their Airbnb is just going to pay for itself… You gotta be careful." (32:44)
  • Key Pitfall: The "easy" tax-saving narrative is overhyped; deep knowledge/pro guidance is crucial to avoid costly mistakes.

7. What to Do with Extra Saved ‘Tax Money’ from a Business (34:53)

Question from Adrian H. (34:53):
Business owner, tax account surplus—should the $14K excess stay in a high-yield savings account or be invested?

• Robert’s Advice (35:11):

  • "Any overage that you have above and beyond the taxes that you set aside... I would love to see that into those ETFs and index funds..."
  • "If it's in a traditional brokerage account, you can take that money anytime you want..." (36:27)
  • Keep a sensible cash buffer for business, but invest the rest for growth.

• Austin’s Practice (36:51):

  • Personally keeps exact tax amount in high-yield savings, but would invest the "excess" if confident in estimates.
  • "You don't have to perfectly optimize every last penny... nobody's reality is perfect." (38:17)
  • In short: Park the surplus in investments, but err on the side of safety with tax liabilities.

Notable Quotes

• On mixing finances with a partner:
  Austin: "Until you guys are married, I want you guys to be using 'I have this invested, she has that saved.' You guys are not together in the eyes of the law..." (04:00)
• On investing at market highs:
  Robert: "I don't care what the stock price is, I care about where I believe it's going in three to five years." (13:36)
• Long-term investment philosophy:
  Austin: "Bears sound smart, bulls make money." (14:23)
• On late financial bloomers:
  Robert: "You're not late. You have plenty of years ahead to build wealth if you follow the plan..." (10:39)
• On private sector vs. military pension:
  Austin: "Your $52,000 a year will not [grow], but $2M will double again to $4M... your spouse, your children... will get a $4M inheritance." (21:40)
• On short-term rentals for taxes:
  Robert: "I don't want you just jumping in, not knowing the rules... this is a tremendous way to move forward and save money on taxes, but... spend a little more time..." (30:44)
• On business cash management:
  Austin: "You don't have to perfectly optimize every last penny... we're all gonna leave money on the table some way, somehow, somewhere." (38:17)

Timestamps for Key Questions

• [03:06] — Girlfriend living together, shared mortgage/invest vs. paydown
• [07:41] — Pay off student loans with cash savings?
• [11:58] — Investing at all-time highs or waiting for a dip?
• [17:02] — Stay in military 6 more years or jump to private sector?
• [22:37] — Should we sell a paid-off townhome to diversify?
• [28:21] — Short-term rentals as tax strategy for high-income docs
• [34:53] — Should business excess tax funds be invested?

Tone & Language

Conversational, direct, no-nonsense but supportive. Both hosts are candid with opinions, balancing tough love (especially around relationships and money) with encouragement and proven frameworks. Listeners are encouraged to seek professional advice for nuanced situations, illustrating that financial literacy is a journey undertaken together.

This summary is intended to provide a clear and actionable recap for those who haven’t listened, spotlighting the episode’s most valuable insights and memorable wisdom.