Rich Habits Podcast Summary — Q&A: Investing While Unemployed, Attending College in an AI-First World, & Selling $250K of Microsoft
Hosts: Austin Hankwitz & Robert Croak
Date: January 22, 2026

Episode Overview

In this lively Q&A episode, Austin and Robert address a range of financial questions from their audience, focusing on practical money management during unemployment, portfolio allocation strategies, the real value of college in a changing AI-driven world, and maximizing the value of side hustles and LLCs. The hosts provide real-world advice, share personal experiences (and mistakes), and discuss how to adopt a rich mindset, regardless of current circumstances. Their dynamic (35-year age gap, with Robert's seasoned business wisdom and Austin's millennial/Gen Z entrepreneurial lens) ensures perspectives are both time-tested and fresh.

Key Discussion Points & Insights

1. Investing While Unemployed

(Starts: 03:15)

Question: Listener Hanson was laid off with a six-month emergency fund, $86k in investments, $25k in a Roth IRA, minimal debt, and asks if he should pause investing during his job search.

• Austin’s take:

  • Treat unemployment as a financial emergency; preserve cash flow.
  • "When times are lean, you need to get very lean."
    — Austin [05:30]
  • Pause investment contributions (not stop) until employment is secured.
  • Focus on survival mode: "You don’t need to be going on vacation. You don’t need to be eating out."
    — Austin [05:38]

• Robert’s advice:

  • Shift mindset from waiting for the perfect side hustle to finding immediate work: "You're looking for a job. I don't care what the job is. You're looking for money and there's money everywhere. You just got to go out and get it."
    — Robert [06:30]
  • Don't let ego prevent you from taking work "below" your previous level—income is essential, and it’s temporary.
  • Avoid the trap of complicated side hustles that require ramp-up; prioritize immediate cash (retail, rideshare, etc.) over launching new ventures.

• Both emphasize not to sell long-term investments for short-term needs and to leverage AI tools like ChatGPT for job applications and resume optimization.

2. Building a Long-Term Portfolio (For a 38-Year-Old Investing for 10 Years)

(Starts: 11:53)

Question: Lee B. plans to invest a lump sum ($15k, then $5k/month) in US ETFs (VOO, SCHG, SCHD) and asks about portfolio allocation.

• Robert’s advice:

  • At 38, include more growth/tech exposure (QQQ, AIQ), not just dividend-focused funds.
  • Reduce SCHD (dividend ETF) to a smaller slice (<15%) unless there are special circumstances; favor S&P 500 and Nasdaq.
  • "Weighting is very important... Too many people don't understand the importance of the weighting..."
    — Robert [14:27]

• Austin’s contribution:

  • Understanding and managing ETF overlaps to avoid redundancy (e.g., owning SPY and VOO).
  • "Having the right names... is less important than having the right weightings..."
    — Austin [13:15]
  • Add diversification with thematic ETFs (aerospace/defense – XAR; Bitcoin ETF – IBIT, if desired) but keep core bets on major indexes.

• Practical Lesson: Weighting = portion (%) of each asset in your portfolio. Use simple analogies (pizza slices) to understand allocation. Overlapping investments hurt returns.

3. Lease vs. Buy: The Luxury Car Dilemma

(Starts: 19:04)

Question: Lori S. (age 59) can pay cash for a new luxury car or lease while investing the cash. She asks for guidance.

• Robert’s stance:

  • If you like getting a new car every 2-3 years, lease.
  • If you want to buy, "You buy used," not new, and not with cash.
  • "I would keep leasing. Get the 12,000 mile lease and if you own a business, you can write it off..."
    — Robert [22:00]

• Austin’s take:

  • Avoid tying up cash in a depreciating asset; that cash can double in the market over six years.
  • The decision depends heavily on net worth: "If you've got millions... go buy the used car... If you’re living below your means, neither—buy reliable, affordable used and invest more."
  • Wonderful illustration of opportunity cost.

4. How To Use an LLC for Side Hustle Success

(Starts: 27:19)

Question: John D., a multi-hyphenate creative, just formed an LLC. He feels spread thin and wants to know how to focus and leverage his business structure.

• Robert’s advice:

  • Beware of "shiny ball syndrome." "Two or three of these items are probably more of a distraction and less of an income earning strategy for you."
    — Robert [29:18]
  • Track time/earnings for each pursuit; cut the least productive.
  • Avoid commingling personal/LLC funds—keep accounts separate for both legal and business clarity.

• Austin’s coaching:

  • Choose one area to go “all in” for 12 months.
  • "Any growth at all compounds... zero does not compound. Zero will stay at zero forever."
    — Austin [31:41]
  • Document the journey (Instagram, TikTok) — that transparency attracts community and opportunities.
  • Maximize LLC by writing off business expenses (portion of apartment, cell phone, tools, supplies, etc.).

• Memorable Quote:
  "Don't be a jack of all trades and a master of none."
  — Robert [34:56]

5. Is College Still Worth It in an AI-First World?

(Starts: 35:29)

Question: Carson B. — is higher education still valuable or cost-effective with rapid AI disruptions?

• Robert’s overview:

  • College worthwhile only for specialized degrees with staying power.
    "So many jobs that currently you would want a college degree for are going to be gone in five years because of AI..."
    — Robert [35:51]
  • White-collar jobs (e.g., law, some medicine) are vulnerable, but healthcare (like nursing), skilled trades, or highly specialized technical roles remain strong bets.

• Austin’s framework:

  • Analyze the Return on Investment: "Don't borrow more (in loans) than you expect to make in your first year out of college."
  • Community college + transfer can hugely reduce costs without sacrificing earning power.
  • There’s value in the college experience (if family pays), but not if self-funding with no payoff.
  • "Go to college to learn to, to do a job in the future and make sure that that job... you have a clear path to do that job..."
    — Austin [39:16]

• Alternatives to College (If Skipping):

  1. Try different trades/industries to discover strengths, then climb that path (e.g., retail to management, skilled trades).
  2. "Buck the system" — become an entrepreneur leveraging AI and free/low-cost knowledge. Examples: content creation, dropshipping, online service businesses.
  3. Companies are increasingly hiring based on skill, not degrees.

• Memorable Example:
  "There's a guy on TikTok named Morris Made... making leather belts in his garage... over one and a half million dollars worth of revenue."
  — Austin [46:15]

Notable Quotes & Memorable Moments

• "Your bills do not care. All they care about is you paying them."
  — Robert [09:04]

• "Any growth at all compounds... zero does not compound. Zero will stay at zero forever."
  — Austin [31:41]

• "Don't be a jack of all trades and a master of none."
  — Robert [34:56]

• "Go to college to learn to do a job in the future and make sure that job... you have a clear path to do that job."
  — Austin [39:16]

• “The opportunity to make money is so abundant right now... College is not the only way.”
  — Austin [46:15]

Timestamps for Major Segments

| Segment | Timestamp | |------------------------------------------------|---------------| | Q1: Investing While Unemployed | 03:15–11:53 | | Q2: 10-Year Portfolio Planning & Weightings | 11:53–19:04 | | Q3: Lease vs. Buy (Luxury Car Dilemma) | 19:04–27:19 | | Q4: Maximizing Side Hustles/LLC | 27:19–35:29 | | Q5: College Value in an AI-First World | 35:29–47:25 | | Wrap-up, encouragement, and final thoughts | 47:25–48:38 |

Takeaways for Listeners

• Prioritize cash flow and financial flexibility when facing unemployment — survival mode trumps “status,” and instant income is better than slow-building side hustles.
• For 10-year investing horizons, favor growth and mainline index exposure over income/dividends until closer to retirement; mind your portfolio weightings!
• Don’t sink big capital into depreciating assets if it jeopardizes investment growth — especially when retirement nears.
• Go deep, not wide: focus your career/side hustle energies on one thing at a time for maximum compounding effect.
• The college equation isn’t one-size-fits-all: do the math, know your end goal, compare alternatives, and understand the new world of AI-driven disruption.
• Entrepreneurship, trades, and self-driven learning are viable (and in many cases, preferable) paths to financial success.

Overall Tone:
Encouraging, practical, candid, and full of actionable advice — with a strong emphasis on the importance of adaptability, humility, and intentionality in building rich habits for any financial circumstance.