The Side Hustle Show – Episode 695 Summary

Episode Title: The Most Unique Niches, Small Town Side Hustles, Monetizing Art, and More: Q&A with Nick
Host: Nick Loper
Date: September 8, 2025

Overview

This special Q&A episode features host Nick Loper answering listener questions on diverse topics: starting a side hustle with money, small-town opportunities, privacy for online entrepreneurs, practical AI applications, newsletter sponsorships, unique ways to monetize art, unusual side hustle niches, and philosophical questions about entrepreneurship. The episode showcases Nick’s actionable advice, real-life stories from past guests, and plenty of firsthand experience.

Key Discussion Points & Insights

1. Choosing the Best Side Hustle for You

Timestamp: 01:05–02:55

• Listener Question: If you had $5,000 to invest, which side hustle would you do now?
• Nick’s Answer:
  • The “right” side hustle isn't universal; it depends on your skills, interests, and connections.
  • Having $5,000 opens up more options (e.g., buying equipment, investing in training). However, validation (proven demand) is more important than money.
  • Avoid spending on things without confirming there's real market demand. "I would venture that millions, maybe even billions have been spent building stuff that nobody wanted. It's an expensive education." (01:35, Nick)
  • He refers listeners to prior frameworks for ideation (episode 683) and the Side Hustle Show archives.
• Memorable Moment:
  • “It’s almost irrelevant… you still gotta go through that decision phase, that ideation phase.” (02:37, Nick)

2. Small Town Side Hustles and Monetizing Food Products

Timestamp: 03:12–07:12

• Listener Question: Ideas for a mom with two small kids in a small town making one-off sales of homemade food.
• Key Advice:
  • Turn occasional sales into recurring revenue streams by:
    • Partnering with local cafes/shops for wholesale arrangements.
    • Offering weekly or monthly meal prep/planning services.
    • Collaborating with shops that feature local products, especially if the town is touristy.
    • Teaching classes (in person/online) on making preserves/pesto (Outschool mentioned).
  • Story: Jen's custom cookie business, selling pre-ordered cookies for premium prices while minimizing inventory risk, an idea for product creators.
• Encouragement:
  • “Two under two is what I like to call survival season... so lots of respect for you for even trying to do something productive.” (03:33, Nick)
• Online Pivot Suggestion: Data annotation, remote freelancing, VA services—opportunities not dependent on location.

3. Running an Anonymous Online Business

Timestamp: 07:12–10:20

• Listener Question: How to operate a website, LLC, and newsletter anonymously for privacy.
• Nick’s Practical Tips:
  • Use registrar privacy protection for domain names.
  • Use a virtual mailbox or PO Box for CAN-SPAM compliance on email newsletters.
  • Set up an LLC using a registered agent (especially in privacy-friendly states like Delaware/Wyoming, but Nick prefers local state for simplicity).
  • Leverage professional vagueness or AI avatars for brand presence.
  • Anonymous marketing: sometimes easier now (Reddit, Twitter/X), but building trust for high-ticket services may be a challenge.
• Quote:
  • “On the website side then all you gotta do is be professionally vague... or create nowadays an AI avatar to represent the brand.” (07:57, Nick)
  • “Now, marketing anonymously can be challenging, but maybe less so than it has been in the past...” (09:32, Nick)

4. Getting Started with AI as a Side Hustler

Timestamp: 10:20–14:48

• Listener Question: How do I get started with AI?
• Nick’s Recommendations:
  • Integrate AI into your daily life and work; don't overthink monetization at first.
  • Example: Used ChatGPT to analyze blood work and got a more satisfying breakdown than from a busy doctor.
    “I punched that in. I said, hey ChatGPT, I'm going to upload some blood work results... It created its own little table summary of the results.” (11:09, Nick)
  • On the business side: use AI for content generation, filling in gaps, podcast transcript editing, show notes summaries, and workflow automation.
  • Start with what interests you and explore AI tools for content creation, coding, automation, etc.
  • Resources: Recommends episodes #650, #566, and #677 for specific AI use cases.
• Memorable Moment:
  • “If it works, it frees me up from these tedious nuts and bolts... to do more of what I like.” (13:29, Nick)

5. Keyword Research—How to Find What’s Trending

Timestamp: 17:11–19:58

• Listener Question: How to see what people are searching for (trending topics/data)?
• Recommended Tools:
  • Paid: Ahrefs, Semrush, Ubersuggest (free tier).
  • Free: Google Trends, Google Keyword Planner (via free Ads account), Keywords Everywhere (Chrome extension), and On Etsy: Erank; on YouTube: TubeBuddy.
  • Emphasis on catching “a rising tide” and using data to compare/contrast term popularity and competitiveness.
• Practical Example:
  • TubeBuddy’s title scoring for YouTube videos: “You can type in really similar variations and one score is a 23 and one score is a 77... I'm going to pick the one with the higher number...” (19:44, Nick)

6. Apps That Pay You to Watch Videos

Timestamp: 20:02–22:53

• Listener Question: Which apps pay for watching videos?
• Reality Check: Most apps pay only pennies—e.g., Slice the Pie, Media Probe market research—but it’s not scalable.
• Higher Earning Approaches:
  • Video captioning/subtitling (AI is changing this market)
  • Video editing for creators
  • Launching content businesses (movie reviews, reaction channels)
  • Example: Kat Watches Horror Movies YouTube channel grew to 100K+ subscribers.
• Quote:
  • “There are surprisingly several different apps… but in most cases those videos are just a code word for advertisements and the pay is really low.” (20:11, Nick)

7. Newsletter Sponsorships: How Nick Monetizes His Newsletter

Timestamp: 22:53–24:58

• Listener Question: How is the Paved sponsor platform? How do you get newsletter sponsors?
• Experience:
  • Used Paved for about 30 campaigns (~1/month); most sponsorships are inbound, few direct outreaches.
  • Other networks: Kit (email service provider ads)
  • Case Study: Ryan Sneddon (Naptown Scoop) filled five ad spots a day at a $70 CPM in a 40K population town—by doing proactive outreach and landing anchor sponsors.
  • “Paved specifically and newsletter sponsorships more broadly have been kind of a nice little incremental income stream.” (23:49, Nick)
  • Key metrics: list size and send frequency.
• Memorable Moment:
  • "He had like half the town on his newsletter earning a dollar per subscriber per month." (24:42, Nick)

8. Monetizing Drawing and Art Hobbies (besides portraits/pet art)

Timestamp: 25:25–30:55

• Listener Question: Simple ways to earn money drawing without portraits, YouTube, or heavy marketing?
• Nick’s Suggestions:
  • Partner with local businesses (give away samples, split on print sales)
  • Sell prints at local markets/craft fairs (especially city/landmark views)
  • Teach drawing/cartooning to kids (as in Wade from Googenius.com—$500/week via Facebook/groups/schools)
  • Architectural/house portraits (e.g., Jesse Spencer Smith’s pen & ink commissions, built via Instagram)
  • "Learn with me" content/daily challenges (engagement from following your progress, not as a pro)
  • Redesigning signatures (Priscilla Molina—Planet of Names, earning $5K/month on TikTok+custom signature packages)
• Quote:
  • “What a really, really creative way to monetize kind of a somewhat art but somewhat calligraphy, like a handwriting type of skill.” (30:09, Nick)
• Notable Story:
  • “[Priscilla] charges $25–120 per custom signature... was earning around $5,000 a month, driven primarily from TikTok.” (30:18, Nick)

9. Side Hustle Addiction & Opportunity Cost

Timestamp: 33:13–36:06

• Listener Question: Concern over a friend obsessed with "make money online" schemes, neglecting traditional work.
• Nick’s Perspective:
  • Sympathizes, having gone through similar phases; opportunity cost is real.
  • Recommends stabilizing finances via traditional employment if possible, then returning to side hustles.
  • Refers to Nathan Barry’s "ladders of wealth creation"—you can skip rungs, but not the skill-building.
  • It took Nick three years before the podcast made income, but he would have regretted quitting.
• Quote:
  • “Some people are never going to be happy working for someone else... An entrepreneur... will work 80 hours for themselves to avoid working 40 for someone else.” (34:52, Nick)

10. Personal: Marriage and Support

Timestamp: 36:06–37:37

• Listener Question: Are you still married to your high school sweetheart?
• Nick: Yes, happily married 25 years. Credits his wife’s support during tough times: “My beautiful bride said something along the lines of stop, pause, timeout, you’re going to be miserable. You can figure this out.” (36:41, Nick)

11. Being in a TV Commercial / CNBC Course

Timestamp: 36:59–39:43

• Listener Question: Spotted Nick in CNBC commercial?
• Nick: Yes! Was invited to record a masterclass-style side hustle course for CNBC; a unique, memorable experience even though it wasn’t a big payday.

12. Should Rich People Have Side Hustles?

Timestamp: 39:43–42:13

• Listener Question: Do successful people really need more side hustles?
• Nick: No problem with celebrities leveraging their brands, and understands people pursue more for legacy, challenge, or because “goalposts keep moving.”
  • Referenced the “18 summers” concept (value of time with family over endless work).
• Quote:
  • “Some people, they've already earned the last dollar they're ever going to spend and now they're trading good time, good hours, good years for useless dollars...” (41:03, Nick)

13. Most Unique Side Hustle Niches

Timestamp: 42:23–45:32

• Listener Question: What’s the most unique side hustle niche you’ve come across?
• Nick’s Favorites:
  • Reselling donated stuffed animals (Charlotte Liebling)
  • Ancient coin collecting and resale (Dean Kinzer)
  • Australian fantasy football content creation (Hef Gerlach)
  • Renting out dresses (Summer Fisher)
  • Teaching video games to kids on Outschool (Devin Ricks)
  • Rubik’s Cube competitions (kid winner, $5,000 prize)
  • Pay-what-you-want poetry on manual typewriters
  • Interior design for dorm rooms
  • Etsy pet headstones
  • Baby name consultant ($1.5–10K/name)
  • The White Noise podcast ($18K/month)
  • The Purple Store in Seattle—everything purple, in business for 20+ years
• Memorable Quote:
  • “You can monetize just about any, any, any skill here... there is a niche for everything.” (44:00, Nick and 45:13)

Notable Quotes & Memorable Moments

• “What all of those neglect is what’s important to you. What do you care about? What unique skills, interests, connections do you have?” – Nick (01:13)
• “The good news is you’re already making sales and that’s the hardest part — proving demand.” – Nick (06:48)
• “No, we’re still very happily married... spanning four decades of this relationship to the late 1900s, as the kids say.” – Nick (36:12)
• “Some people are never going to be happy working for someone else... An entrepreneur... will work 80 hours for themselves to avoid working 40 for someone else.” – Nick (34:52)
• “The Purple Store... every product is purple. That’s a niche.” – Nick (45:13)
• “You can make money doing anything, right?” – Nick (43:29)

Timestamps for Key Segments

• $5,000 Side Hustle Dilemma – 01:05–02:55
• Small Town Side Hustle Ideas – 03:12–07:12
• Anonymous Website/LLC Advice – 07:12–10:20
• AI for Hustlers – 10:20–14:48
• Keyword Research Tools – 17:11–19:58
• Apps That Pay for Video Watching – 20:02–22:53
• Newsletter Sponsorships & Monetization – 22:53–24:58
• Making Money with Art/Drawing – 25:25–30:55
• Side Hustle Addiction & Opportunity Costs – 33:13–36:06
• Marriage & Support – 36:06–37:37
• CNBC TV Commercial Anecdote – 36:59–39:43
• Should the Rich Side Hustle? – 39:43–42:13
• Most Unique Niches – 42:23–45:32

Final Thoughts

Nick Loper’s signature blend of empathy, hands-on knowledge, and practical optimism runs through this rich Q&A episode. Whether you’re looking for marketing shortcuts, passive income ideas, or simply validation that your niche is viable (yes, even if it’s purple everything), this episode delivers actionable wisdom and motivation for side hustlers at every stage.