Podcast Summary: The Side Hustle Show – Episode 712
Title: How to Unlock New Side Hustle Ideas with AI
Original Air Date: December 15, 2025
Host: Nick Loper
Guest/Co-Host: Allison Baggerly (Inspired Budget podcast)
Podcast Description: Legit strategies, creative ideas, and real talk about making and growing extra income streams.
Episode Overview
This episode explores how to use AI—specifically ChatGPT—to generate side hustle ideas that are personally tailored, actionable, and creative. Instead of relying on impersonal, generic lists of side hustles, Nick walks Allison through a step-by-step framework and demonstrates a free worksheet and prompt for ChatGPT. They highlight how to clarify your skills, interests, and constraints to unlock new entrepreneurial possibilities, and show how AI can become a brainstorming buddy for more fulfilling side hustles.
Key Discussion Points & Insights
1. The Problem with "Listicle" Side Hustle Ideas
- [00:00] Nick (A): Most people don't find their side hustles from Googling generic lists. Personalized intersection of skills + interests + market demand is key.
"It's really, really rare to find somebody when I say, well, how'd you come up with that idea?... I scrolled down to number 17 on the list and was like, bingo, that's the one." — [00:16], Nick
2. Tiers of Side Hustles
- Plug-and-play (quick money): Rideshare, DoorDash, Rover, Airbnb, etc. Fast, low-barrier, but limited control and scalability.
"App powered... Not a ton of specialized skills required. The platforms are doing a little bit of the marketing for you." — [01:52], Nick
- Mini-businesses: Product, service, and content businesses offer more control, possible to scale, and deeper satisfaction, but require more time and upfront effort.
"The big three that we see... are product businesses, service businesses, and then audience or content-based businesses." — [02:55], Nick
3. Personal Experience and Brainstorming with ChatGPT
- Nick introduces a worksheet to help prompt ChatGPT for personalized side hustle ideas.
- Allison volunteers her own skills, interests, and constraints as a case study.
"We'll use this version as a demo version. Do you want to fill this in for yourself as we go?" — [09:03], Nick
The Worksheet Prompts (with Allison's Answers):
- Skills: Public speaking, teaching, money coaching, writing, organizing
- Interests: Hiking, embroidery, puzzles, reading, helping friends/family with budgets and decluttering
- Childhood Dream: Acting, being on stage, theater
- Natural expertise: Communication, empathy, time-blocking, setting boundaries
- Time constraints: 5-10 hours/week, remote, flexible scheduling
- Income goal: $1-2k/month within 6-12 months ([20:27]-[21:46])
Notable Quote & Moment
“Sometimes when you’re talking with a friend and they’re able to see you in a different light... ChatGPT might be able to see something. That's an option we never even thought of."
— [36:01], Allison
Important Segment Timestamps & Key Exchanges
The Live Demonstration: Allison’s Side Hustle Brainstorm
- [23:01-24:38]: ChatGPT’s suggestions based on Allison’s profile
- 1: Money coaching ([23:44])
- 2: Public speaking coaching ([24:44])
- 3: Time blocking/productivity coaching ([25:21])
- 4: Podcast/YouTube channel “Money Made Simple” ([26:48])
- 5: Decluttering and productivity coaching ([27:06])
- 6: Accountability buddy subscription ([27:42])
- [24:59] Nick: “Most people fear public speaking more than they fear death. So... there must be something to that.”
- [25:41] Allison: Shares immediate imposter syndrome when suggested public speaking coaching.
Expanding and Refining Ideas
- [29:04] Allison resists “coaching”—wants more creative, less people-facing options.
- [31:40] ChatGPT pivots to:
- Digital tools and templates
- “Declutter in a Weekend” guide ([32:08])
- Digital courses/workshops
- Budget autopsy newsletter ([32:57])
- Themed challenges (e.g. 30-day declutter, budget resets)
- Hand-embroidered/digital art products ([33:52]-[34:30])
Practical, Actionable Advice
- [35:15] Nick suggests using ChatGPT for detailed action plans and roadmap.
“You can ask it for further details on each of them... Write me a realistic 30 day action plan and it'll do it. It’s really cool.” — [35:15], Nick
Notable Quotes & Memorable Moments
-
On list-based ideas:
“After 650 interviews, it’s really, really rare to find somebody … who says, 'well, I Googled side hustle ideas ... and it was like, bingo, that's the one.’ It doesn’t usually happen that way.”
— [07:50], Nick -
On using AI to unearth hidden talents:
“Sometimes we are blind to them … ChatGPT might be able to see something. That’s an option we never even thought of.”
— [36:01], Allison -
On product business potential:
"Even the stuff that we offload on Facebook Marketplace... it feels free to me because it’s like, well, we weren't using it anymore.”
— [03:21], Nick -
Action Plan with ChatGPT:
"Ask it for further details... ‘Given the time constraints above, write me a realistic 30 day action plan’ and it’ll do it.”
— [35:15], Nick
Recommendations & Free Tools
- Free worksheet: List out your skills, interests, “childhood dream job,” perceived expertise, time constraints, and income goals (get it at sidehustlenation.com/allison)
- Customize your ChatGPT prompt: Replace authorial influences, details, and priorities for more tailored results.
- Use ChatGPT interactively: Iterate with clarifications (e.g., “no coaching”, “make it creative”, “how to hit $500 in two months” etc.)
Practical Takeaways
- Personalization is key. Generic online lists rarely fit—you have to combine your skills, interests, and market demand.
- AI supercharges brainstorming. ChatGPT can help you see connections and opportunities you might miss.
- Don’t stop at the first ideas. Use ChatGPT or another AI to refine, elaborate, and simulate action plans.
- You can do all this for free, using Nick’s worksheet and ChatGPT’s free tier.
Conclusion/Next Steps
Anyone motivated to start a side hustle can use the episode’s framework and tools to uncover unique, actionable ideas—and quickly prototype them with AI’s help. Download the worksheet from Side Hustle Nation, plug in your answers, and use ChatGPT as a creative business partner.
"I love that he is thinking outside of the box and creating tools that you can use at home to get your juices flowing and figure out other ways to make money."
— [38:47], Allison
Get the worksheet: sidehustlenation.com/allison
Try your own AI-powered side hustle brainstorm.