Rich Habits Podcast

Episode: Q&A: Retirement Investing for Entrepreneurs, Medical School Debt, & Our Favorite Books and Podcasts
Hosts: Austin Hankwitz & Robert Croak
Date: December 25, 2025

Overview

In this Q&A edition of the Rich Habits Podcast, Austin and Robert dive into real-life listener questions touching on financial stability, early retirement planning, entrepreneurship, medical school debt, real estate strategies, emotional vs. mathematical money decisions, and their top book and podcast recommendations from 2025. Their advice is a mix of practical investing strategies, strong stances on financial products, and emphasis on aligning money choices with personal happiness and long-term vision.

Key Discussion Points and Insights

1. Maximizing Financial Stability for Tech Professionals

[05:54 – 10:53]

Listener Profile (EC):
- Mid-to-late 40s couple, 2 kids, high-tech salary ($210K gross), substantial equity in home, strong retirement balance.
Robert’s Advice:
- Focus on diversification for stability, not just aggressive growth.
- Consider diversifying into real estate (REITs or platforms like Fundrise) and precious metals.
- “Don’t go so diversified that you get yourself in harm’s way and lose that comfort that you’ve already built...” (Robert, 06:26)
Austin’s Tactical Suggestions:
- Reduce overexposure to employer stock—move toward broad index funds or low-volatility assets.
- Keep 4-6 months’ expenses in a high-yield savings account to fortify against tech industry volatility.
- Recasting a low-rate mortgage can lower monthly payments without refinancing (especially if job security is uncertain).
- “Having that low monthly payment for your mortgage could be a really good idea.” (Austin, 09:25)
- Strongly advised against paying off a 2.6% mortgage early: “…at 2.5% I don’t think it makes any sense in the world to do that.” (Austin, 08:40)

2. Retirement Savings and Taxes for Entrepreneurs (LLC & S-Corp Scenarios)

[12:00 – 16:33]

Listener Profile (John):
- Farm manager advised by his boss to form an LLC, pay himself a salary/dividends, and use a SEP-IRA for tax benefits.
Robert’s Analysis:
- Setting up an LLC with S-Corp election is only worthwhile when earning $80K-$100K+ annually due to operating costs.
- You “can open an LLC and make it an S election later...but you can’t open an S corp and move it to an LLC.”
Austin’s Dive into Tax Strategy:
- As an S-Corp, pay self a “reasonable” salary and take remainder as (lower-taxed) distributions.
- Example: $100K profit, $60K salary (full payroll taxes), $40K dividends (federal tax only), yielding significant tax savings—netting a few thousand dollars in savings after S-Corp costs.
- SEP IRA allows up to 25% of salary to be contributed, further reducing taxable income.
- Cautions that the setup is most beneficial once income and savings goals are high enough to justify complexity.

3. Emotional vs. Mathematical Reasoning when Paying Off Low-Rate Mortgages

[17:27 – 22:57]

Listener Profile (Jay):
- 33-year-old couple, million+ net worth including investments and a $400K S-Corp distribution. Considering paying off $175K mortgage at 3% for peace of mind.
Austin’s Core Advice:
- “Personal finance is personal.” (Austin, 17:59)
- Emphasizes emotional factors can trump math—if paying off debt feels best, do it.
- “...you figure it out along the way and you do what you want to do. Would I do it? Probably not. Would Robert do it? Definitely not.”
Robert on Arbitrage:
- Math strongly favors investing “arbitrage” over paying off 3% debt (SP500 returns likely much higher).
- Advises using a calculator or ChatGPT to assess the compounding difference when investing vs. paying off the mortgage.
- “If the S&P makes 8, 9, 10, 11, 12% a year and you can borrow money for 3%, I’m always going to borrow money and keep chunking away into my investment portfolios.” (Robert, 21:27)
- Final message: As long as you understand your numbers and the emotions, you can’t really lose.

4. Financial Planning for Young Doctors with Debt & SMA Accounts

[23:21 – 27:53]

Listener Profile (Max B):
- 25-year-old about to finish med school, $100K debt, $60K invested, military-bound (VA loan likely), considering advisor suggestion of Separately Managed Accounts (SMAs).
Austin’s Strong Warning:
- “Kind of weirded out that a CFP…[is] trying to pump you into an SMA.” (Austin, 25:06)
- Explains SMAs are high-fee, actively managed accounts: “...charging you one, one and a half percent on your money to hopefully outperform the S&P500. Like that’s what it is, right?”
- Recommends staying with low-cost index investing—“Just go put money in the S&P and the NASDAQ…close your eyes for 20 years. You’re going to be a millionaire.” (Austin, 26:23)
On Real Estate via VA Loans:
- Robert: Buy only if you’ll hold 5-7+ years; otherwise, rent and keep investing. VA loans require at least 1 year in-residence before renting out.

5. Saving for Real Estate without Sacrificing Investment Base

[27:54 – 32:19]

Listener Profile (Jordan H, 24):
- Civil engineer, $80K/yr, building 401k, brokerage, has $12K student debt (4%), $15K left on truck loan, passionate about real estate, wants to buy a duplex.
Robert’s Caution:
- Advises patience: “I think you’re a little early. I would not consider buying a piece of real estate at this point in your career until I had the base built.” (Robert, 30:37)
- “Get your base built…$50K, $80K, $100K invested across all your accounts” before diverting savings to a real estate down payment.
- If insistent, use FHA/5% down loans and avoid big renovations.

6. Recommended Books, Podcasts & Tools of 2025

[34:40 – 38:36]

Robert’s Picks:
- Tools: Seeking Alpha, Public.com’s Generated Assets, Google Finance’s new beta platform.
- Podcasts: All In, Dumb Money (Chris Camillo), Chris Camillo’s interviews.
- Books:
  - The Richest Man in Babylon
  - Atomic Habits
  - Think and Grow Rich
  - Zero to One (Peter Thiel)
  - One Up on Wall Street (Peter Lynch)
Austin’s Additions:
- Podcasts: The Rundown (Public), Social Currency (Sammy Cohen), Tiger Sisters (mindset), Joe Rogan & Naval Ravikant’s “How to Get Rich” (Ep. 1309), and Naval’s YouTube content.
- Books: Millionaire Mission (Money Guys), Little Book of Common Sense Investing, Five Types of Wealth (Sahil Bloom).
- Favorite Quote: “If you want to really get rich in life, you have to provide value to people at scale. You have to stop trading time for money.” (Naval Ravikant, via Austin, 37:52)

7. Young Listener Trapped in Whole Life/Indexed Universal Life (IUL) Policy

[38:53 – 45:20]

Listener Profile (Crystal C, 19):
- Paying $1,200/mo into a 10-pay half-million dollar life policy; also has a Roth IRA; works as insurance cold caller; considering entrepreneurship.
Austin & Robert’s Unapologetic Advice:
- “You’re just doing it wrong…and I don’t mean that in a mean way. I mean it in a mathematically factual way.” (Austin, 39:21)
- Condemnation of whole life/IUL as “investment”—high fees, illiquidity, most benefits accrue to the insurance company/agent, not to the individual.
- “Would you rather have $7 million that’s your money…or half a million that’s not your money (you have to borrow it out, it doesn’t go to your heirs)?” (Austin, 42:44)
- Robert: “If it was truly an investment and you missed three payments, your money would still be there and still be growing. But unfortunately...it’s not really an investment.”
- Strong recommendation to cancel and redirect payments into a market index fund—potential for millions by retirement if starting young.

Notable Quotes & Moments

“Personal finance is personal.” – Austin (17:59) & Robert (22:57)
“If the S&P makes 8, 9, 10, 11, 12% a year and you can borrow money for 3%, I’m always going to borrow money and keep chunking away into my investment portfolios...” – Robert (21:27)
“Would you rather have $7 million that’s your money…or half a million that’s not your money?” – Austin (42:44)
On SMAs/advisor fees:
- “Avoid paying high fees as long as you possibly can, especially at 25 years old.” – Austin (25:47)
On S-corps & business strategy:
- “There are a lot of benefits to this and [your boss] is spot on with paying yourself first and then paying yourself the rest in dividends at the end of the year.” – Robert (12:50)
On insurance and investment scams:
- “Guess what? They’re making themselves millionaires off the backs of hardworking people...” – Robert (44:47)

Key Timestamps

05:54 – Financial Stability Q&A (Tech Family)
12:00 – S-Corp/LLC Strategies & SEP IRAs for Entrepreneurs
17:27 – Should You Pay Off a 3% Mortgage for Peace of Mind?
23:21 – Young Doctor: SMA Accounts, Student Debt, Renting vs Buying
27:54 – Real Estate Investing for Young Professionals
34:40 – Hosts’ 2025 Book, Podcast, and Tool Recommendations
38:53 – 19-Year-Old Listener in a Whole Life Policy Trap

Final Thoughts & Takeaways

Diversification is key for stability—but don’t overdo it.
Never rush into real estate before building a solid investment base.
Low-cost index investing beats almost anything, especially when young.
Be wary of high-fee “investment” products—know who’s really getting rich.
Emotional satisfaction sometimes justifies “illogical” financial moves, as long as you understand the cost.
Focus on personal financial literacy and align your money choices with your unique life goals and mindset.

End of Summary

Rich Habits Podcast

Episode: Q&A: Retirement Investing for Entrepreneurs, Medical School Debt, & Our Favorite Books and Podcasts
Hosts: Austin Hankwitz & Robert Croak
Date: December 25, 2025

Overview

Key Discussion Points and Insights

1. Maximizing Financial Stability for Tech Professionals

[05:54 – 10:53]

Listener Profile (EC):
- Mid-to-late 40s couple, 2 kids, high-tech salary ($210K gross), substantial equity in home, strong retirement balance.
Robert’s Advice:
- Focus on diversification for stability, not just aggressive growth.
- Consider diversifying into real estate (REITs or platforms like Fundrise) and precious metals.
- “Don’t go so diversified that you get yourself in harm’s way and lose that comfort that you’ve already built...” (Robert, 06:26)
Austin’s Tactical Suggestions:
- Reduce overexposure to employer stock—move toward broad index funds or low-volatility assets.
- Keep 4-6 months’ expenses in a high-yield savings account to fortify against tech industry volatility.
- Recasting a low-rate mortgage can lower monthly payments without refinancing (especially if job security is uncertain).
- “Having that low monthly payment for your mortgage could be a really good idea.” (Austin, 09:25)
- Strongly advised against paying off a 2.6% mortgage early: “…at 2.5% I don’t think it makes any sense in the world to do that.” (Austin, 08:40)

2. Retirement Savings and Taxes for Entrepreneurs (LLC & S-Corp Scenarios)

[12:00 – 16:33]

Listener Profile (John):
- Farm manager advised by his boss to form an LLC, pay himself a salary/dividends, and use a SEP-IRA for tax benefits.
Robert’s Analysis:
- Setting up an LLC with S-Corp election is only worthwhile when earning $80K-$100K+ annually due to operating costs.
- You “can open an LLC and make it an S election later...but you can’t open an S corp and move it to an LLC.”
Austin’s Dive into Tax Strategy:
- As an S-Corp, pay self a “reasonable” salary and take remainder as (lower-taxed) distributions.
- Example: $100K profit, $60K salary (full payroll taxes), $40K dividends (federal tax only), yielding significant tax savings—netting a few thousand dollars in savings after S-Corp costs.
- SEP IRA allows up to 25% of salary to be contributed, further reducing taxable income.
- Cautions that the setup is most beneficial once income and savings goals are high enough to justify complexity.

3. Emotional vs. Mathematical Reasoning when Paying Off Low-Rate Mortgages

[17:27 – 22:57]

Listener Profile (Jay):
- 33-year-old couple, million+ net worth including investments and a $400K S-Corp distribution. Considering paying off $175K mortgage at 3% for peace of mind.
Austin’s Core Advice:
- “Personal finance is personal.” (Austin, 17:59)
- Emphasizes emotional factors can trump math—if paying off debt feels best, do it.
- “...you figure it out along the way and you do what you want to do. Would I do it? Probably not. Would Robert do it? Definitely not.”
Robert on Arbitrage:
- Math strongly favors investing “arbitrage” over paying off 3% debt (SP500 returns likely much higher).
- Advises using a calculator or ChatGPT to assess the compounding difference when investing vs. paying off the mortgage.
- “If the S&P makes 8, 9, 10, 11, 12% a year and you can borrow money for 3%, I’m always going to borrow money and keep chunking away into my investment portfolios.” (Robert, 21:27)
- Final message: As long as you understand your numbers and the emotions, you can’t really lose.

4. Financial Planning for Young Doctors with Debt & SMA Accounts

[23:21 – 27:53]

Listener Profile (Max B):
- 25-year-old about to finish med school, $100K debt, $60K invested, military-bound (VA loan likely), considering advisor suggestion of Separately Managed Accounts (SMAs).
Austin’s Strong Warning:
- “Kind of weirded out that a CFP…[is] trying to pump you into an SMA.” (Austin, 25:06)
- Explains SMAs are high-fee, actively managed accounts: “...charging you one, one and a half percent on your money to hopefully outperform the S&P500. Like that’s what it is, right?”
- Recommends staying with low-cost index investing—“Just go put money in the S&P and the NASDAQ…close your eyes for 20 years. You’re going to be a millionaire.” (Austin, 26:23)
On Real Estate via VA Loans:
- Robert: Buy only if you’ll hold 5-7+ years; otherwise, rent and keep investing. VA loans require at least 1 year in-residence before renting out.

5. Saving for Real Estate without Sacrificing Investment Base

[27:54 – 32:19]

Listener Profile (Jordan H, 24):
- Civil engineer, $80K/yr, building 401k, brokerage, has $12K student debt (4%), $15K left on truck loan, passionate about real estate, wants to buy a duplex.
Robert’s Caution:
- Advises patience: “I think you’re a little early. I would not consider buying a piece of real estate at this point in your career until I had the base built.” (Robert, 30:37)
- “Get your base built…$50K, $80K, $100K invested across all your accounts” before diverting savings to a real estate down payment.
- If insistent, use FHA/5% down loans and avoid big renovations.

6. Recommended Books, Podcasts & Tools of 2025

[34:40 – 38:36]

Robert’s Picks:
- Tools: Seeking Alpha, Public.com’s Generated Assets, Google Finance’s new beta platform.
- Podcasts: All In, Dumb Money (Chris Camillo), Chris Camillo’s interviews.
- Books:
  - The Richest Man in Babylon
  - Atomic Habits
  - Think and Grow Rich
  - Zero to One (Peter Thiel)
  - One Up on Wall Street (Peter Lynch)
Austin’s Additions:
- Podcasts: The Rundown (Public), Social Currency (Sammy Cohen), Tiger Sisters (mindset), Joe Rogan & Naval Ravikant’s “How to Get Rich” (Ep. 1309), and Naval’s YouTube content.
- Books: Millionaire Mission (Money Guys), Little Book of Common Sense Investing, Five Types of Wealth (Sahil Bloom).
- Favorite Quote: “If you want to really get rich in life, you have to provide value to people at scale. You have to stop trading time for money.” (Naval Ravikant, via Austin, 37:52)

7. Young Listener Trapped in Whole Life/Indexed Universal Life (IUL) Policy

[38:53 – 45:20]

Listener Profile (Crystal C, 19):
- Paying $1,200/mo into a 10-pay half-million dollar life policy; also has a Roth IRA; works as insurance cold caller; considering entrepreneurship.
Austin & Robert’s Unapologetic Advice:
- “You’re just doing it wrong…and I don’t mean that in a mean way. I mean it in a mathematically factual way.” (Austin, 39:21)
- Condemnation of whole life/IUL as “investment”—high fees, illiquidity, most benefits accrue to the insurance company/agent, not to the individual.
- “Would you rather have $7 million that’s your money…or half a million that’s not your money (you have to borrow it out, it doesn’t go to your heirs)?” (Austin, 42:44)
- Robert: “If it was truly an investment and you missed three payments, your money would still be there and still be growing. But unfortunately...it’s not really an investment.”
- Strong recommendation to cancel and redirect payments into a market index fund—potential for millions by retirement if starting young.

Notable Quotes & Moments

“Personal finance is personal.” – Austin (17:59) & Robert (22:57)
“If the S&P makes 8, 9, 10, 11, 12% a year and you can borrow money for 3%, I’m always going to borrow money and keep chunking away into my investment portfolios...” – Robert (21:27)
“Would you rather have $7 million that’s your money…or half a million that’s not your money?” – Austin (42:44)
On SMAs/advisor fees:
- “Avoid paying high fees as long as you possibly can, especially at 25 years old.” – Austin (25:47)
On S-corps & business strategy:
- “There are a lot of benefits to this and [your boss] is spot on with paying yourself first and then paying yourself the rest in dividends at the end of the year.” – Robert (12:50)
On insurance and investment scams:
- “Guess what? They’re making themselves millionaires off the backs of hardworking people...” – Robert (44:47)

Key Timestamps

05:54 – Financial Stability Q&A (Tech Family)
12:00 – S-Corp/LLC Strategies & SEP IRAs for Entrepreneurs
17:27 – Should You Pay Off a 3% Mortgage for Peace of Mind?
23:21 – Young Doctor: SMA Accounts, Student Debt, Renting vs Buying
27:54 – Real Estate Investing for Young Professionals
34:40 – Hosts’ 2025 Book, Podcast, and Tool Recommendations
38:53 – 19-Year-Old Listener in a Whole Life Policy Trap

Final Thoughts & Takeaways

Diversification is key for stability—but don’t overdo it.
Never rush into real estate before building a solid investment base.
Low-cost index investing beats almost anything, especially when young.
Be wary of high-fee “investment” products—know who’s really getting rich.
Emotional satisfaction sometimes justifies “illogical” financial moves, as long as you understand the cost.
Focus on personal financial literacy and align your money choices with your unique life goals and mindset.

End of Summary

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Q&A: Retirement Investing for Entrepreneurs, Medical School Debt, & Our Favorite Books and Podcasts

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Summary

Rich Habits Podcast

Overview

Key Discussion Points and Insights

1. Maximizing Financial Stability for Tech Professionals

2. Retirement Savings and Taxes for Entrepreneurs (LLC & S-Corp Scenarios)

3. Emotional vs. Mathematical Reasoning when Paying Off Low-Rate Mortgages

4. Financial Planning for Young Doctors with Debt & SMA Accounts

5. Saving for Real Estate without Sacrificing Investment Base

6. Recommended Books, Podcasts & Tools of 2025

7. Young Listener Trapped in Whole Life/Indexed Universal Life (IUL) Policy

Notable Quotes & Moments

Key Timestamps

Final Thoughts & Takeaways

Summary

Rich Habits Podcast

Overview

Key Discussion Points and Insights

1. Maximizing Financial Stability for Tech Professionals

2. Retirement Savings and Taxes for Entrepreneurs (LLC & S-Corp Scenarios)

3. Emotional vs. Mathematical Reasoning when Paying Off Low-Rate Mortgages

4. Financial Planning for Young Doctors with Debt & SMA Accounts

5. Saving for Real Estate without Sacrificing Investment Base

6. Recommended Books, Podcasts & Tools of 2025

7. Young Listener Trapped in Whole Life/Indexed Universal Life (IUL) Policy

Notable Quotes & Moments

Key Timestamps

Final Thoughts & Takeaways