Rich Habits Podcast – Q&A: Feeling Squeezed, Gambling on Canadian Real Estate, & Off-Market Deals
Hosts: Austin Hankwitz & Robert Croak
Date: September 18, 2025

Overview

In this dynamic Q&A episode, Austin and Robert dig into seven listener-generated questions covering practical side-hustle strategies, feelings of financial “squeeze” despite doing everything right, navigating speculative real estate in Canada, off-market real estate deals, investment options for the self-employed, the risks and rewards of using a HELOC to invest, and how a self-made multi-millionaire should deploy a fresh $1.2 million in capital. The episode combines strategic financial advice, candid anecdotes, and actionable wisdom for listeners at every stage of their wealth-building journey.

Key Discussion Points & Insights

1. Side Hustles for Accountants & the Myth of Entrepreneurial Side Hustling ([02:37]–[07:10])

• Listener Question: John H., a flexible accountant working only 10 hours/week, asks for remote side-hustle ideas, especially as a bookkeeper.
• Austin's Take:
  • Debunks the idea that every side hustle needs to be a complicated entrepreneurial venture.
  • “You don’t have to start a business to do a side hustle. Sometimes people confuse, oh side hustle. That means I gotta go start a… not always.” ([04:09])
  • Highlights low-barrier gig work (Uber, DoorDash, Instacart) as a fast way to earn extra cash without heavy upfront investment.
• Robert’s Advice:
  • Leverage professional skills: “You could go into Facebook groups, spend $5 a day on Nextdoor ads, and I promise you, you could find 20 clients that need help with their bookkeeping.” ([05:12])
  • Suggests accountants network at local business and real estate meetups, and provide value in online community groups instead of just advertising.

2. Feeling Squeezed Even When Doing Everything Right ([07:17]–[11:44])

• Listener Question: AG (age 28, married, $140k household income, no debt except a low-rate mortgage, maxing all tax-advantaged accounts) feels “squeezed” and wonders if it’s lifestyle creep.
• Austin’s Take:
  • Encourages AG to consider reducing aggressive investing to ease short-term discomfort.
  • “You’re probably investing 25, maybe up to 30% of your take home pay… Consider dialing that back maybe to just the match and the Roth IRA.” ([09:32])
  • Reinforces the importance of finding a balance: “Life is more than just numbers on a computer screen going up.” ([11:44])
• Robert’s View:
  • Redefines lifestyle creep: it isn’t just big purchases but also small, repetitive ones (e.g., 13 Stanley mugs).
  • “Little leaks sink ships… people drain their bank accounts month in and month out by the little things.” ([10:49])
  • Stresses intentional spending: “Now you just need to learn how to not waste money.” ([11:30])

3. Gambling on Canadian Real Estate: Sell or Hold? ([11:44]–[17:45])

• Listener Question: PL, age 50 (Toronto), bought an empty pre-construction home in 2020 for $1.3M cash, now worth less, costing $20k/year to keep, and wonders whether to hold for appreciation or cut losses.
• Robert’s Direct Answer:
  • “You have to sell the house… there just isn’t enough appreciation in that market for you to sit and wait and play catch up.” ([14:53])
  • Emphasizes opportunity cost: investing $1M from the sale could yield $100k/year, versus bleeding $20k annually.
  • “Make your money work as hard for you as you work to get it.” ([15:37])
• Austin’s Input:
  • “You’re worth well over $4 million. You can take a $100,000 hit… That’s really going to be able to turbocharge your retirement goals.” ([15:57])
  • Suggests shopping for lower realtor fees to minimize the loss.

4. Investing When Self-Employed: Beyond the 401(k) ([17:45]–[19:36])

• Listener Question: Amy V. asks about best stock market investing options when fully self-employed.
• Austin’s Step-by-Step:
  • Roth IRA or Traditional IRA: “Always encourage people to check out the Roth IRA... up to $7,000 a year.” ([17:52])
  • Solo 401(k): “I do the mega backdoor Roth Solo 401k which means I can turbocharge my retirement investing up to $70,000 a year, which is insane.” ([18:24])
  • Taxable brokerage: For any overflow after maxing retirement accounts.
• Robert’s Plug:
  • Recommends the Rich Habits Network for in-depth weekly guidance for self-employed investors.

5. Off-Market Deals & Real Estate Cash-on-Cash ([20:47]–[26:44])

• Listener Question: Miguel, first-time investor in Detroit, finds a four-plex off-market deal and compares it to index funds.
• Austin’s Math:
  • “$4,000 rent/month, $2,200 mortgage, $600 expenses… $1,200/month cash flow. Cash on cash return: 18.7%.” ([21:32])
  • Highlights tax advantages and suggests: “You’re going to be pretty much doing twice as good as the market does.” ([22:52])
• Robert’s Caution:
  • “Don’t just take the word of whoever’s selling this to you… do some comps… get and pay for an inspection.” ([24:01])
  • Advises automating investment of real estate cash flow (max out Roth IRA, invest the rest).
• Finding Off-Market Deals:
  • “You have to do the work… Most of my best real estate deals… came from me having an idea, driving an area, finding the property.” ([27:12])
  • Encourages networking in local meetup groups and engaging the real estate community.

6. Should I Use HELOC Debt to Invest for Yield Arbitrage? ([28:43]–[33:47])

• Listener Question: SK has $1.2M in home equity and considers pulling $600k via HELOC to invest in high-yield ETFs, using dividends to cover the debt.
• Austin’s Caution:
  • “What happens if… the markets next year fall by 30%?… Now you missed nine HELOC payments, now they’re going to take your home.” ([30:07])
  • Warns about distribution volatility: “This sounds like a get rich quick scheme… I like to be disciplined. I like to be normal. I like to just get rich slow.” ([31:52])
• Robert’s Reality Check:
  • “I don't know of any HELOCs below 7%. If you’re finding a HELOC at 5%, I don't know where you're getting it, please tell me...” ([32:24])
  • Recommends getting an actual HELOC quote, ensuring true numbers make sense, and being mindful of both principal and interest obligations.

7. Deploying New Millions: Portfolio Construction for the Well-Off ([33:47]–[42:12])

• Listener Question: E (47, single mom, entrepreneur, multi-millionaire, $1.2M sale pending) wants to know how to invest proceeds and minimize fees.
• Austin’s Core Wisdom:
  • Focus on portfolio percentages, not dollar amounts: “If you can focus on keeping things proportional and in percentages, that is the way to succeed.” ([34:07])
  • “65–85% invested into well diversified index funds… 15–35% into other sectors like precious metals, crypto, speculative ETFs.” ([35:18])
  • Suggests draining high-yield savings and checking accounts to proper emergency fund levels; invest the rest.
• Robert’s Practical Tips:
  • “Negotiate with [your advisor] where their fee breaks are… always get a second opinion, make sure you’re diversified.” ([38:16])
  • For real estate, recommends using LLCs, a holding company, and a revocable trust for asset protection.

Notable Quotes & Memorable Moments

• Austin (on side hustles): “You don’t have to start a business to do a side hustle… you can make your first $15 literally in the next 20 minutes on one of these apps.” ([04:03])
• Robert (on lifestyle creep): “Little leaks sink ships… I don’t care what other financial people say… that’s bullcrap.” ([10:49])
• Austin (on investing aggressively): “Life is more than just numbers on a computer screen going up.” ([11:44])
• Robert (on offloading bad real estate): “Make your money work as hard for you as you work to get it.” ([15:37])
• Austin (on risky arbitrage): “This sounds like a get rich quick scheme... I like to just get rich slow.” ([31:52])
• Robert (on thoroughness in real estate deals): “Don't just take the word of whoever's selling this to you… do some comps… get and pay for an inspection.” ([24:01])
• Austin (re portfolio management for the wealthy): “Just think about percentages and ratios. Don’t think so much about the dollar amount because the dollar amount for you is only going to get bigger.” ([35:18])
• Robert (on legal structures): “For the real estate, I don't know if you have individual LLCs for each property… I would make sure to have a holding company… and a revocable trust…” ([39:44])

Timestamps for Key Segments

• [02:37] – Side hustles & bookkeeping as an accountant
• [07:17] – Feeling squeezed despite high income & good habits
• [11:44] – Toronto real estate dilemma: hold or sell at a loss?
• [17:45] – Retirement investing options when self-employed
• [20:47] – Analyzing a Detroit off-market multifamily deal
• [28:43] – Using a HELOC to invest: risks & rewards
• [33:47] – Managing millions after an entrepreneurial exit

Tone & Takeaways

Throughout the episode, Austin and Robert are candid, practical, and supportive. They demystify financial complexity, reinforce the value of simple, proven strategies, and remind listeners to stay grounded in fundamentals even as their net worth grows. Whether advising rookies or seasoned millionaires, their mantra is clear: be intentional, avoid shortcuts, and don’t let finance get in the way of enjoying life.

A must-listen for anyone wanting actionable, real-world advice on building and preserving wealth, avoiding costly detours, and creating a legacy of financial security—without losing sight of what matters along the way.