The Side Hustle Show | Episode 697: “10 Recurring Revenue Side Hustles”
Host: Nick Loper
Date: September 18, 2025
Episode Overview
In this episode, Nick Loper spotlights 10 actionable recurring revenue side hustles, pulling in real-life stories and expert tips from past guests. Recurring revenue models offer a more predictable and steady income stream, helping side hustlers break free from the feast-or-famine cycle, and many can be scaled or automated. Each example illustrates how solving a recurring problem can unlock sustainable growth—whether you’re leveraging digital tools, offering local services, or turning expertise into revenue.
1. Software as a Service (SaaS) / White Labeling Software
Featured Guest: Chris Lelini ([from episode 494])
Timestamps: [00:58]–[05:55]
- Key Concept: Sell subscriptions to software without building it yourself by white-labeling a product.
- Execution: Purchase seats/licenses at wholesale and resell at retail; provide a consulting/support layer for added value.
- Scalability: No geographic restriction; clients nationwide via digital marketing and referral networks.
- Profitability: Multi-six figure business, high margins.
- Metrics: Focus on Monthly Recurring Revenue (MRR); low churn.
- Lifestyle Perk: Enables a location-independent business.
“There's nothing stopping me from picking up and moving to a different state because most of the relationships I've built, most people haven't even seen me, to be honest with you.”
—Chris Lelini [03:59]
“MRR, monthly recurring revenue, is really the key. The churn, it just, it really isn't there.”
—Chris Lelini [05:28]
2. Local Subscription Services
Featured Guest: Erica Krupen ([from episode 614])
Timestamps: [05:55]–[08:44]
- Concept: Weekly/monthly recurring services (e.g., pet waste removal) tackle ongoing needs.
- Pricing: Gradually raised rates as business and reputation grew; average now ~$99/month per customer.
- Customer Base: Sticky, recurring demand as long as the underlying problem persists.
- Scalability: Can hire/trust others to fulfill actual work and focus on growing the business.
- Other Examples: House cleaning, parking lot litter removal, personal chef services.
“I just sent out a letter and just said, hey, I got to raise my prices. This is what it is… if they wanted to cancel service, I completely understood. And some did… But because I was able to bring on thousands more a month, it balanced out.”
—Erica Krupen [07:50–08:39]
3. Online Subscription (Productized Services)
Featured Guest: Eric Dingler ([from episode 684])
Timestamps: [09:00]–[15:30]
- Concept: Offer digital agency services (e.g., SEO, content, marketing) to clients on a subscription basis.
- Structure: Quarterly strategy sessions, content calendars, automation, and outsourced teams (remote).
- Scale: Charge $500–$750/month per client; high profit margins.
- Churn: Minimize by proactively showing results and being transparent.
- Origin Story: Began as a side hustle to fund an adoption—built up through upselling and referrals.
“If you show up every month with a report that's showing results... Most business owners, that's the number one complaint I get when we get a new customer. We were spending all this money. I never knew if it was working.”
—Eric Dingler [13:08–13:25]
4. Rental Properties / Asset Rentals
Featured Guest: Dustin Heiner ([from episode 691])
Timestamps: [18:40]–[20:13]
- Concept: Buy and hold real estate for monthly cash flow.
- Method: Focus on cash flow (not just appreciation); build a portfolio one property at a time.
- Scalable: Start slow, reinvest cash flow; daughter bought first property at 16; goal: buy one per year.
- Alternative Rentals: Scooters, photo booths, hot tubs—higher ROI but more turnover.
“I have over 30 properties that make me money… If I can get 10 of those, $3,000 a month with 10 properties.”
—Dustin Heiner [18:53]
5. Membership Programs
Featured Guest: Liz Wilcox ([from episode 600])
Timestamps: [21:53]–[26:32]
- Concept: Sell access to a digital community or resource library for a monthly fee (her example: $9/month for weekly email templates).
- Mindset: Low cost = low responsibility; built to replace unpredictable client work with steady income.
- Growth: “If I can get 100 members at $9, that’s $900/month… If I could get 1,000 people, that would be $9,000/month.”
- Structure: Templates and content "sawdust" from previous client work; value comes from consistency.
- Variation: Can be education, community, discounts, digital products, etc.
“For my personality, it's actually pretty easy for me to be out and to sell people. And I knew that about Liz Wilcox.”
—Liz Wilcox [24:49]
6. Niche & Directory Websites
Featured Guest: Frey Chu ([from episode 692])
Timestamps: [29:34]–[33:11]
- Concept: Build information-rich directories in underserved niches; monetize with ads/sponsorships.
- Execution: Value-add over basic Google results (updated data, unique features). Examples: thrift store directory, others.
- Proof: 1,000 daily visitors within six months; $1,200/month with minimal hands-on work.
- Why It Works: Scalable, low startup cost, can be automated, and is an asset at exit.
“…I found this website that was getting over 100,000 monthly visitors... I could do better than this. This is pretty ugly… there could be better information.”
—Frey Chu [32:09–32:20]
7. Product Licensing
Featured Guest: Stephen Key (Inventright)
Timestamps: [37:08]–[37:56]
- Concept: Pitch invention/ideas to companies for a royalty (e.g., 5% of gross sales—no manufacturing needed).
- Advantages: No capital required, no inventory, companies ready to listen.
- Execution: Target companies with open product submission portals (e.g., Hasbro Spark).
“You're basically renting your idea to a company… and they're going to pay you on every one they sell.”
—Stephen Key [37:45]
8. Website Design & Hosting (Monthly Retainer Model)
Featured Guest: Ryan Golgoski ([from episode 550])
Timestamps: [39:50]–[42:48]
- Concept: Offer web design, maintenance, and hosting to small businesses for $180–$300/month, rather than a costly upfront build.
- Value: Regular updates, maintenance, better SEO, and conversion—all bundled.
- Scale: Up to 20 new signups per month; break-even in ~2 months per client, then mostly profit.
“It's a pretty simple, easy sell… 180, 220, 300 bucks a month… over time you'll really refine your systems.”
—Ryan Golgoski [39:50–42:30]
9. Subscription E-Commerce
Featured Guest: Ben Faze ([from episode 581]); Product: Pretty Boy Skincare
Timestamps: [44:18]–[45:56]
- Concept: Sell replenishable products on a recurring basis (subscription boxes, DTC consumables).
- Metric: Ensure customer Lifetime Value (LTV) exceeds acquisition cost (CAC).
- Platform: Use Shopify subscriptions, flexible customer management.
- Key: Make it easy to subscribe, modify, or pause; high LTV justifies higher initial ad spend.
“We know… that customer, we are willing to bet heavily that if you buy our product once, you will at least buy one more. And… 60% of our revenue… comes from subscribers.”
—Ben Faze [44:56–45:20]
10. Coaching & Masterminds (Scaled w/ Technology)
Featured Guest: Stephen Faust ([from episode 570])
Timestamps: [47:51]–[51:43]
- Concept: Offer high-touch mentoring via asynchronous video/audio message tools (e.g., VideoAsk), enabling one-to-many at scale.
- Model: $39/month membership gives access to all digital products, monthly workshop, and unlimited 1:1 video Q&A.
- Scale: Users value "on call" access—rarely overuse, making it sustainable.
- Sticky: Priceless perceived value, low drop-off.
“I stopped doing member calls because mainly I didn't like doing them… So what I do now is… unlimited one on one mentoring. Unlimited mentoring for $39 a month plus all the stuff that they get in there as well.”
—Stephen Faust [47:51–48:17]
“I might get one or two a week. I don't get many at all. Yeah, I just don't get it because I think people see that as, oh, this is a pretty, pretty high value, important thing. I want to make sure I use it the right way.”
—Stephen Faust [51:14]
Memorable Quotes & Speaker Attributions
- “If you want recurring revenue, you gotta solve a recurring problem.”
—Nick Loper [05:55] - “One property can pay you month after month, year after year.”
—Nick Loper [18:40] - “Low cost equals low responsibility, because I think that's an interesting distinction.”
—Nick Loper [24:14] - “High perceived value… definitely sustainable from Stephen’s standpoint.”
—Nick Loper [51:43]
Major Takeaways
- Recurring revenue side hustles center on solving recurring problems for long-term, stable income.
- Most models are scalable—either by outsourcing fulfillment (labor, digital, or content) or via automation.
- Choose a side hustle that matches your interests, skill set, and time commitment.
- Successful examples blend creativity, resourcefulness, and a value-first mentality.
Additional Resources
For links to all referenced episodes and detailed summaries, visit Side Hustle Nation’s show notes.
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