
What can a crossing guard, a car negotiator, and a mindfulness bracelet teach you about building a side hustle? Quite a bit, it turns out.
This week, I sat down with Jason VanDevere to talk about some of the most unique side hustle ideas out there right now.
Jason is the creator of the Goal Crazy and Goal Crazy Planners, author of Dream Driven: The Step-by-Step Process to Discover Your Perfect Business Idea and Launch it This Year, and a longtime real estate investor.
He’s a serial side hustler who brings a sharp eye for opportunity, and this episode is packed with them.
Tune in to Episode 733 of the Side Hustle Show to learn:
- how a former car salesman turned negotiation into a $200k/month business
- why a crossing guard’s handwritten mailer now earns $14,000 a month
- two overlooked business ideas with low startup costs and real potential
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Round 1: Unconventional Side Hustles
The $1K-Per-Deal Car Negotiator
Tomi Mikula is a 33-year-old former car salesman from North Carolina who turned his dealership know-how into a paid service. He negotiates car deals on behalf of strangers — and charges $1,000 per deal.

Before he ever charged a cent, Tomi closed 50 deals for free to build credibility and learn what clients actually needed. That grind paid off. According to the Wall Street Journal, he’s now earning $200K/month and has built a following of 600K subscribers across YouTube and TikTok.
He’s also expanded into used car concierge services. One fun detail: some dealers recognize his voice and hang up immediately, which is why he’s reportedly looking into a voice changer.
You can learn more at delivrdto.me.
$2K-$10K/Month Selling Watches That Don’t Tell Time
Greg, the founder of Now Watch — a watch designed to display the present moment rather than the time — says the first five years, he made “almost nothing.”

Then an influencer posted about it. Orders picked up, other creators reached out for collaborations, and slowly the business started moving.
He was still working full-time in marketing for a hospitality company while all of this was happening.
It’s not passive income; he’s been clear about that — “there is still work involved, sometimes a lot” — but the upside is real.
As he put it, “sometimes I wake up and see that I already made my rent overnight, which still feels a bit unreal.”
$25k/Month from a Vibe-Coded App
Mau Baron built PrayerLock, a Christian prayer app, in just 3 days. The premise is simple: the app locks your phone until you complete a prayer session.
The tagline is “Do you have 1 minute for God?”

It took him 3 years and 10 attempts to reach $25,000/month.
He started with organic app store optimization and content marketing, then added paid influencer marketing before scaling with paid ads — going from $2,500/month to $25,000/month with 50% profit margins.
Subscriptions run from $9.99 to $79.99. He’s also working on a step-lock app as his next project.
This AI Agent Made $250k While He Slept
Nat Eliason set up an AI agent named Felix, not as a chatbot, but as a fully autonomous “employee.”

Felix has his own email address, X (Twitter) account, Stripe account, and Mercury business bank account. Nat even rewrote Felix’s identity files to state: “You are the CEO of this company.”
The constraint: Felix must build 100% of everything himself. Nat provides high-level ideas, API keys, and a credit card for expenses, but never touches the code.
Felix’s revenue comes from multiple streams: an info product (“How to Hire an AI”) that made $1,000 in its first 24 hours, a paid marketplace called Claw Mart, an AI agency called Claw Sourcing, and crypto trading fees from his own token.
As of the recording, Felix’s total earnings were roughly $300,000 — made up of $60,000 in USD, about $85,000 in Ethereum, and roughly $150,000 in Felix Tokens.
Nat describes it as a zero-person business.
The Crossing Guard with a $14K/Month Mailer
Christine Tyler Hill is an artist and illustrator in Vermont who also works as an elementary school crossing guard.
She started posting monthly “cloud reports” on Instagram — handwritten, illustrated snapshots of what she noticed at the intersection each day: migrating geese, funny trash, a pitbull in a knitted sweater.
When people started asking where their report was if she forgot to post, she took it a step further. In January, she launched The Cloud Report — an 8-page handwritten zine printed on cream cardstock, hand-bound, stamped, and labeled in her studio.

It goes out to subscribers every month for $8/month or $81/year. According to the Wall Street Journal, she now has about 2,000 paying subscribers — roughly $14,000/month from her observations at a crosswalk.
Round 2: Business Idea Donations
Idea 1: Picture Books for Older Adults with Dementia
Jason’s first idea came from watching his grandfather with Alzheimer’s.
Visiting is hard because conversation becomes limited, so what do you actually do together?
His idea: picture books designed for older adults, styled like children’s books.
Jason sees it as a potential blue ocean — an underserved niche with real emotional value. It could also be AI-assisted and produced through Amazon Print on Demand, keeping overhead low.
Idea 2: Flipping Playsets
Facebook Marketplace is full of free playset listings. The problem isn’t supply — it’s that nobody wants to deal with disassembling, transporting, and reassembling a large outdoor playset.
That friction is where the business lives.
Families give these away for free all the time, and Jason sees an opportunity to pick them up, clean them up, and resell for around $500 with free delivery.
The model mirrors the couch-flipping playbook — build a free-pickup relationship, then profit on the back end. You need a vehicle and some labor, but the margin potential is there.
Round 3: The Triple Threat
A Marketing Tactic That’s Working Right Now
Jason is using Amazon FBA (Fulfilled by Amazon) not just to sell, but to build an email list.
The funnel works like this: buyers get access to free training videos, then a downloadable printable, which requires an email opt-in.
From there, an email nurture sequence leads to a coaching call booking. It’s a way to turn Amazon’s massive traffic into owned audience relationships.
A New Tool He’s Loving
Jason’s current favorite tool is Manus — an AI agent that operates with its own computer screen.
Unlike chatbots that respond to a prompt and stop, Manus can browse, log into platforms, run research, and take sequential actions on its own.
Jason has used it to help run ads and assist with web design. It was recently acquired by Meta.
Favorite Book from the Last 12 Months
10X Is Easier Than 2X by Dan Sullivan and Dr. Benjamin Hardy.
Jason had heard people recommend it for a while and figured the title explained the whole concept.
The core idea: going after 10x goals forces you to get clear on what actually matters and say no to everything that doesn’t.
For Jason, the clearest path to that number runs through his book and coaching program — not one-off digital downloads or standalone products.
What’s Next for Jason?
Jason is focused on streamlining his business and building out the coaching side.
He now has a beta group of six people becoming Goal Crazy certified coaches — something he didn’t anticipate when he started selling planners.
You can find his planner and more at goalcrazy.com and goalcrazyplanners.com.
Episode Links
- Goal Crazy
- Goal Crazy Planners
- Dream Driven: The Step-by-Step Process to Discover Your Perfect Business Idea and Launch it This Year
- Tomi Mikula
- Delivrdto.me
- Now Watch
- Now Watch Reddit Post
- YouTube: This AI Agent Made $250K While He Slept
- The Cloud Report
- Manus
- 10X Is Easier Than 2X
Looking for More Side Hustle Help?
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- Join the free Side Hustle Nation Community. The free Facebook group is the best place to connect with other side hustlers and get your questions answered.
- Download The Side Hustle Show. My free podcast shares how to make extra money with actionable weekly episodes.





