The Side Hustle Show – Episode 698: Reacting to Reddit Side Hustles

Host: Nick Loper
Guest: Whitney Bonds
Release Date: September 22, 2025

Episode Overview

In this episode, Nick Loper is joined by side hustle expert Whitney Bonds to react to a curated list of unique and high-earning side hustle ideas that are actively discussed on Reddit. The duo analyzes each idea’s legitimacy, earning potential, and the strategies people are using to find success—all with an emphasis on actionable takeaways. The conversation is full of real-world experiences, creative approaches, and honest assessments, making it a goldmine for listeners looking to start or expand a side gig.

Key Side Hustles and Insights

1. Passive Income with YouTube Tutorials (01:26–05:34)

• Strategy: Create evergreen "how-to" videos on YouTube aimed at answering popular search queries.
• Whitney's Experience:
  • Created a "how to start an LLC" video that sat dormant for five months but eventually took off.
  • That video generated over 200,000 views, $30K+ in ad revenue, and $100,000+ in affiliate commissions (03:55).
  • Quote: “So this is all about just creating tutorial style content for YouTube and it lives on and it really is passive…do it once and it can live on for years.” – Whitney Bonds (01:58)
• Tips:
  • Update older topics with your own spin.
  • Monetize through both ad revenue and affiliate partnerships.
  • Be patient—success can take time to materialize.

2. Flipping Apples/Lemonade Stands (05:34–07:52)

• Idea: Buy apples cheaply, make candy apples, and sell them at local spots or events for a considerable markup.
• Real-life Examples:
  • Nick recounts stories of kids making $100+ in an afternoon with lemonade stands.
  • Discussion on pricing strategies: charge a set price vs. pay-what-you-want (07:03).
• Notable Quote: “People want to empower you…to know that you can put a value on something and get money back for it.” – Whitney Bonds (07:32)

3. Pressure Washing Service (08:08–10:39)

• Earnings: Reddit posts report grossing $100K/year working 6 months.
• Startup Costs:
  • Can start low (a few hundred dollars) or high (up to $30K in equipment).
• Retention Approach:
  • Offer recurring deals for annual cleaning.
  • Leverage neighborhood visibility to land referrals.

4. Writing on Medium (10:39–13:49)

• Redditor's Achievement: $10K+ in one month—an unusually high but achievable result after years of effort.
• Challenges:
  • Virality is rare and difficult to replicate.
  • The platform is saturated and not as lucrative for most writers.
• Transition: Whitney and Nick agree newsletters remain a better long-term avenue for writers.
• Quote: “I do still believe heavily on newsletters…I still open people’s emails that create good content.” – Whitney Bonds (13:25)

5. Pop-Up Wedding Proposal Service (16:46–19:24)

• Niche: Creating custom, Instagram-worthy marriage proposals with decor rentals, earning $400–$800 per event.
• Key Point: Strategic partnerships (e.g., with jewelers) can drive referrals.
• Memorable Quote: “I think this is a perfect… for the person who’s, like, creative, likes to think outside the box and, like, be a part of these different experiences.” – Whitney Bonds (17:17)

6. Window Cleaning Business (19:24–20:36)

• Earnings: Reported $1,000/day, particularly among college students.
• Tactics: Social ads to book jobs, door-to-door upsells while on-site.

7. Trash Can Cleaning Service (20:36–23:20)

• Market: $10–$20 per bin; local Facebook groups as a lead source.
• Growth Hack: Leave sticky notes on bins curbside after trash day.
• Whitney's Experience: Paid $28 for two bins cleaned by a teenage entrepreneur.

8. Candle Making & Print-on-Demand Gifts (23:46–26:49)

• Differentiation: Unique angles (affirmation quotes, custom designs) help candles stand out in saturated markets.
• Printify Angle: Nick highlights print-on-demand possibilities for candles, luggage, and other items—not just T-shirts.
• Quote: “I’m a lot less price sensitive when it’s a gift and it’s a unique gift.” – Nick Loper (25:53)

9. Pinterest Monetization Struggles (27:33–30:48)

• Whitney’s Caution: Pinterest success is much harder post-2019; paid ads are necessary for significant reach.
• Affiliate Earnings Issues: Window for Amazon affiliate conversions is short (24 hours); Pinterest users may not be in buying mode.

10. Youth Sports Officiating (32:50–34:54)

• Wage: $45–$55 per game; good exercise and a way to stay connected to sports.
• Challenge: Dealing with critical parents and coaches.
• Motivation: “If you wanted to stay close to the game and you enjoy it anyways…kind of a fun after work side hustle.” – Nick Loper (33:59)

11. Succulent and Plant Propagation (34:54–36:41)

• Why It’s Cool: Clippings turn into salable plants—“money that literally grows from the ground.”
• Market: $5–$20 per plant via Facebook Marketplace.

12. Pet Sitting for the Affluent (37:28–39:44)

• Niche: Focusing on clients (“rich people who travel often”) who pay $100/day for in-home pet care.
• Platforms: Rover, local referrals, and word-of-mouth.
• Quote: “Once you build that reputation…you don’t need that many new clients.” – Nick Loper (39:10)

13. Unusual Pet Services: Pet Baptisms (39:44–40:54)

• Originality: No established market—could be an untapped niche in certain regions.
• Reaction: Laughter and skepticism, but acknowledges that people will pay for highly unique services.

14. Furniture Assembly (via TaskRabbit & Similar) (41:09–42:57)

• Earnings: $50/hour, sometimes more with tips; is accessible work if you can follow instructions.
• TaskRabbit & Angie Home Services: Popular platforms, now owned by furniture giants (e.g., IKEA).
• Quote: “You just need to read the instructions.” – Whitney Bonds (42:03)

Whitney's “Trend to Watch”: Voice AI for Local Businesses (43:26–45:57)

• Business Model: Set up AI voice assistants for local companies (e.g., plumbers), creating passive monthly revenue.
• Earnings: Some are charging $1,000/month for these services.
• Sales Approach: Ask business owners about missed calls and the cost of missed new business to drive interest.

Notable Quotes

• Whitney Bonds on YouTube Tutorials:
  “If you go to how to become a bookkeeper or how to go high level tutorial, like, I do this intentionally so people can see my videos that are actively searching for these things. And so it works.” (04:57)
• On Monetizing Writing:
  “Writing is a challenging side hustle right now just given the state of AI and everything else.” – Nick Loper (13:01)
• On Print-on-Demand Gifts:
  “There’s some unique print on demand niches beyond just T-shirts.” – Nick Loper (26:43)
• On Plant-Selling: “The idea that you just really growing money, I love that for this one.” – Whitney Bonds (35:51)

Recommended Timestamps for Key Segments

• YouTube tutorial passive income – 01:26–05:34
• Pressure washing & window cleaning – 08:08–10:39, 19:24–20:36
• Medium writing & newsletters – 10:39–13:49
• Pop-up proposal service & partnerships – 16:46–19:24
• Trash can cleaning – 20:36–23:20
• Candle/Print on demand – 23:46–26:49
• Pinterest affiliate debate – 27:33–30:48
• Youth sports officiating – 32:50–34:54
• Plant propagation – 34:54–36:41
• Pet sitting for affluent clients – 37:28–39:44
• Furniture assembly/TaksRabbit – 41:09–42:57
• AI for local businesses – 43:26–45:57

Episode Tone

• Conversational, positive, and pragmatic.
• Focused on providing tips you can act on without hype.
• Nick and Whitney blend humor, personal stories, and practical advice.

Final Thoughts

Whitney and Nick cover everything from time-tested blue-collar side gigs (window washing, assembling furniture) to digital “passive” income tactics (YouTube, Medium), and creative new niches (pet baptisms, pop-up proposal services). The recurring theme: look for ways to add value or solve problems—sometimes in surprisingly simple ways—and don’t be afraid to iterate your approach.

Explore more:

• Check out Whitney Bonds on YouTube and triedandtruemomjobs.com for more side hustle inspiration.
• Visit sidehustlenation.com for curated playlists and deeper dives into each discussed hustle.