Rich Habits Podcast — Episode 143: "Side Hustles That Actually Work"

Hosts: Austin Hankwitz & Robert Croak
Date: November 10, 2025

Overview & Main Theme

This episode of the Rich Habits Podcast dives deep into side hustles—specifically, "low friction" gig economy opportunities that regular people can realistically start right away to boost their monthly income. Hosts Austin Hankwitz and Robert Croak break down why side hustles are critical, how to pick the right ones, and the blueprint for actually making extra income (think from $200 to $2,000+/month), all while fitting these hustles around your life sustainably. The episode also addresses listener questions on wealth building, market timing, and diversification.

Key Discussion Points & Insights

1. The Gig Economy & The Case for Side Hustles

Timestamps: 00:46–03:25

• Rapid Growth: The gig economy is booming. Nearly 5.5% of US workers hold multiple jobs, and 39% of Americans have a side hustle.
• Income Ceiling: Expense-cutting only goes so far, but “your income has no ceiling.” – Austin (02:07)
• Compounding Advantage: Small extra earnings invested wisely make a big difference over time.

“There’s always sort of a floor to how low you can cut your expenses, but your income has no ceiling. ... Your income is your greatest wealth-building tool.”
— Austin (02:07)

2. The “Low Friction” Side Hustle Framework

Timestamps: 03:25–05:21

• Principles:

  1. Leverage what you already have (skills, assets, network).
  2. Minimal startup cost (“start this week with no money”).
  3. Flexible hours — fits around your life, not vice versa.

• Sustainability: These aren't about burning out doing Uber Eats 12 hours a day; they're about realistic, sustainable extra income.

“If your side hustle is making you miserable or it’s destroying your relationships, it is not worth it.”
— Austin (04:35)

3. Five Side Hustles That Actually Work

Side Hustle #1: Tutoring & Test Prep

Timestamps: 05:21–07:28

• How It Works: Use your subject expertise—no teaching degree needed.
• Earnings: $25–$75/hr standard; $50–$100+/hr for SAT/ACT prep.
• How to Start: Begin with friends/family, local groups, online platforms (Wyzant, Tutor.com).
• Pros: Flexible, can scale rates as you build testimonials, work from anywhere.
• Cons: Can be seasonal; don’t limit yourself to academics—teach anything you’re good at.

“If you’re a teacher of any kind, this sounds like a no-brainer to me.”
— Robert (06:09)

Side Hustle #2: Local Freelance Services

Timestamps: 07:28–10:43

• Scope: Covers everything from graphic design to bookkeeping to web/AI automation.
• Real Example: Connor from the Rich Habits Network made $80k in 2025 in his local area doing web/graphic design and automation, alongside a 9–5.
• Earnings: $25–$100/hr; small business clients may pay $500–$2,000+/mo for ongoing services.
• How to Start: Focus on local businesses (not Fiverr/Upwork), network in your area, build relationships.
• Pros: Recurring income, scalable; being personable means you can charge more.
• Cons: Requires hustle upfront, but becomes easier once you land clients.

“Don’t start by going to Fiverr or Upwork… you’re now competing globally on price.”
— Austin (08:38)

Side Hustle #3: Task-Based Gigs

Timestamps: 10:43–12:41

• Platforms: TaskRabbit, Handy.com, or flyers/community boards.
• Types of Tasks: Moving help, yard work, furniture assembly, handyman services.
• Earnings: $30–$60/hr on platforms; $100–$300 for a single moving job.
• How to Start: Sign up online or spread the word locally/church bulletins.
• Pros: “Always a job if you’re willing to work”; quick cash, highly flexible.
• Cons: Physical work, trading time for money.

“If you have a good attitude, show up on time and you’re willing to work, there will always be a job for you.”
— Robert (11:05)

Side Hustle #4: Pet Services

Timestamps: 12:41–15:42

• Opportunities: Dog walking, pet/house sitting.
• Earnings: $15–$40 per walk, $25–$75 per day/visit, $50–$100/night for overnight stays.
• How to Start: Use apps (Wag, Rover), build up reviews, then move direct with clients to avoid platform fees.
• Pros: Great for animal lovers, consistent with recurring relationships.
• Cons: Requires reliability; biggest demand around holidays (where you can charge premium rates!).

“There’s a woman in my building ... she’s going to make over $80,000 this year walking dogs.”
— Robert (15:42)

Side Hustle #5: Renting Out Assets

Timestamps: 17:31–19:34

• Assets: Parking spaces, spare storage/rooms, cars (Turo), backyard for events (Peerspace), tools.
• Earnings: Parking $100–$500/mo; Airbnb spare room $500–$2,000/mo; Turo car $300–$1,000/mo; tools $50–$300/mo.
• How to Start: List on relevant platforms (SpotHero, Neighbor.com, Turo, Facebook Marketplace, Airbnb).
• Pros: Often passive; income from stuff you already own; “frictionless.”
• Cons: Some risk (insurance, strangers); know the platform’s policies.

“You have things people want and want to use. ... This requires the least amount of active work, which is beautiful.”
— Robert (18:17)

4. Implementation Advice & Mindset

Timestamps: 19:34–21:43

• Pick just ONE side hustle to start based on your life/skills.
• Do it for 3–6 months, track your earnings, and scale or pivot from there.
• It doesn’t take much ($250–$1,000/mo) to meaningfully change your financial trajectory—pay off debt, build an emergency fund, or start investing.

“The average American is one or two good side hustles away from complete financial breathing room.”
— Austin (20:43)

• These hustles aren’t forever—just a bridge to financial security.

“We’re not saying do it for life, but do it for a year or two to get ahead and get financially free and investing for your future.”
— Robert (21:21)

Notable Quotes & Memorable Moments

• On excuses about time:
  “So many people that I see say they don’t have time, yet they’re watching sports all week every week ... If you want to get out of this trap… you have to make time.”
  — Robert (05:25)

• On pricing freelance services:
  “Be that type of person [clients] want to pay more; you can command a higher price.”
  — Austin (09:27)

• On dog walking:
  “She’s going to make over $80,000 this year walking dogs. And she’s in incredible shape because she probably puts 20,000 steps in a day.”
  — Robert (15:42)

Action-Oriented Final Takeaways

• Start Small, Be Consistent: Pick one idea, commit for a few months, and document your progress.
• Don't overthink diversification initially. Focus on proven, actionable steps—sustainability and fit matter more than perfection.
• Remember the goal: Even a few hundred extra dollars a month can change your finances over time—invest what you earn.

Listener Q&A Highlights

Q1: “We hit $100,000 invested at 25—what now?”

Timestamps: 24:17–25:17

• Robert: Diversify further—consider individual stocks, precious metals, real estate, international ETFs.
• Austin: With a partner, keep finances separate until marriage; think intentionally about next steps like house-hacking, big-picture life planning.

Q2: “Stocks are way up. Should I sell because a recession is coming?”

Timestamps: 26:20–31:50

• Austin: Market isn’t in a total bubble; however, some sectors are. Use core/satellite portfolio approach. If a stock becomes 5–7%+ of portfolio, consider taking profits and reallocating.
• Robert: “Listen to your gut”; dollar cost average profits, stay diversified—don’t be all in on a single trend.

Q3: “I moved my 401k out of a target date fund into large cap index funds. Good move?”

Timestamps: 32:50–34:52

• Both hosts: Yes! Target date funds are low performance, high fee. Managing your own allocations to value/growth/indexes is usually superior; work with an advisor as you near retirement.

Important Timestamps

• [00:46] – Episode intro and gig economy overview
• [03:25] – The low friction side hustle framework
• [05:21] – Side Hustle #1: Tutoring & test prep
• [07:28] – Side Hustle #2: Local freelance services
• [10:43] – Side Hustle #3: Task-based gigs
• [12:41] – Side Hustle #4: Pet services
• [17:31] – Side Hustle #5: Renting out assets
• [19:34] – Implementation strategy and summary remarks
• [24:17] – Listener Q&A: Hitting $100k invested, what next?
• [26:20] – Listener Q&A: Market timing/profit-taking
• [32:50] – Listener Q&A: 401k allocations

Final Words from the Hosts

“Don't pick three, don't pick all five. Pick one side hustle that fits your life and your skills ... The average American is one or two good side hustles away from complete financial breathing room.”
— Austin (19:34)

“Low friction side hustles that work—get yourself ahead. ... Do it for a year or two to get ahead and get financially free and investing for your future.”
— Robert (21:21)

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This summary captures the episode’s practical advice, motivating stories, and roadmap for launching a profitable and sustainable side hustle fit for any schedule or background.