Dog Gyms, Cold Caking, Time Travel Videos, and More

Here are five completely wild businesses, and somehow, each one had something worth stealing.

Chandler Bolt, founder of SelfPublishing.com, is back on the Side Hustle Show for the first time in 12 years.

He built an 8-figure business helping thousands of people write and publish books — and today, he’s here to talk about five emerging business ideas, from a cake dropshipper to a virtual dating matchmaker.

Listen to Episode 746 of the Side Hustle Show to learn:

how a cake middleman earns up to $1,000/day without running a bakery
why a mobile dog gym is a masterclass in targeting the right customer
what makes a virtual dating service one of the highest-margin businesses you can start

(Free Strategy Session — selfpublishing.com/sidehustle — book a free call about your book idea)

Table of Contents show

Round 1: Wild Business Ideas

Cold Caking: The Cake That Books Meetings

William Lindholm’s Daymaker.com is a cake-based lead generation service — he sends custom cakes to sales prospects and earns around $4,000/day in revenue at roughly 30% margins, putting profit at about $1,000/day.

He doesn’t run a bakery. He builds relationships with bakeries, plays middleman, and keeps the margin.

The Numbers

Each cake costs $80
Conversion rate from cake delivery to booked meeting: 35% (vs. 1% for cold email)
At a 33% conversion rate, that’s roughly $240 per meeting
Convert one in four meetings into a sale: $1,000 cost per customer
If your product is worth more than $5,000, the math works

How It Got Started

Lindholm’s original business was delivering birthday cakes to HR departments on auto-subscription — every time someone on the team had a birthday, a cake showed up automatically.

The pivot to outbound sales tool came later. A viral stunt — sending a 100-piece, pitch-deck-themed cake to major VC firms like A16Z and Sequoia — put Daymaker on the map and drove a wave of inbound interest.

Mobile Dog Gym: A Luxury Workout for Your Pup

Run Buddy Mobile parks an air-conditioned Mercedes Sprinter van outside your home, loaded with custom non-motorized dog treadmills.

A session costs $70 for 30 minutes, and 90% of clients book a recurring weekly slot. They’re fully booked and expanding through franchising — with the first new location opening in Austin.

The Business Behind It

Getting one van on the road costs over $110,000 ($70k Mercedes Sprinter + $25k custom treadmills + wrap)
The fleet has grown to 7 vans in Arizona
900,000 TikTok followers — the vans double as mobile billboards
Trainers are certified through an in-house program called Run Buddy University

The startup cost is steep, and the lower price point means the model runs on volume — which demands strong operations. That’s where most people struggle.

But the bigger takeaway is the niche: dog walking has existed forever. A luxury gym experience in the back of a Mercedes is something entirely different.

A fraction of existing dog-walking customers would pay ten times more for a premium version like this — and those are the customers worth targeting.

AI Time Travel Vlog: $8k/Month with “Chloe vs. History”

“Chloe vs. History” is a three-month-old YouTube channel where an AI persona named Chloe vlogs like a modern tourist — except she’s on the Titanic, or at the court of Henry VIII, reacting to history from a 2026 perspective.

In just three months, the channel racked up 17 million views and earns an estimated $8,000/month from long-form content.

The Smarter Business Model

Chandler loves the concept and hates the business model. Ad revenue alone — CPMs, pay-per-click — is a tough foundation.

His more interesting frame: what if this were a break-even customer acquisition channel? Ad money covers production costs. A backend product is where the real money lives.

It’s the same playbook Mr. Beast runs with Feastables: YouTube isn’t the business, it’s the free customer pipeline for the brands behind it.

On the practical side, Chandler’s team at SelfPublishing.com already uses AI avatars via HeyGen to update course content without re-recording.

When Amazon’s algorithm shifts, they update the script and regenerate — faster iteration, lower cost.

Cardboard Cat Condos (and the Pivot to Wool)

After noticing her mother’s cats were ignoring the couch in favor of messy Amazon boxes, one woman decided to make better ones: decorative cardboard condos shaped like:

gingerbread houses
milk boxes
cheese wedges
and haunted houses

It’s grown into a six-figure business with sales across her own store, Amazon, and wholesale accounts through Faire.

The Pivot and the Real Opportunity

Cardboard condos were bulky and expensive to ship — up to $40 per order.

The business pivoted to sustainably sourced wool cat toys, made by a Fair Trade craft guild in Nepal, retailing for $17–$25 and costing only a few dollars to produce.

Sales now break down roughly into thirds: own website, Amazon, and wholesale — with wholesale growing fastest, now in over 100 stores across the U.S. and Europe.

Recurring Consumables

The bigger play, though, is recurring consumables. A monthly cat toy subscription — or any product that ships the same thing every month — keeps SKU complexity low and cash flow predictable.

Chandler pointed to Dr. Squatch (a men’s soap subscription) as the model to study. The rule: keep SKUs as minimal as possible.

A barbecue rub available in a 2-pack or 4-pack beats the inventory nightmare of a golf glove business trying to manage sizes across three designs.

Virtual Dating Service: High-Margin Matchmaking at $1,200–$3,000/Month

Vida Select has been running for nearly two decades, reporting an 82% success rate and 11,000 relationships.

They charge $1,200–$3,000/month to help singles optimize their dating profiles, choose better photos, and filter matches — so clients stop burning time on apps that aren’t delivering results.

Why the Numbers Make Sense

Online dating generates roughly $3 billion/year in the U.S.
About 30 million active daters in the U.S. at any given time
Most are commoditized at $20–$100/month

The reframe that makes this business click: if you make $100/hour and you’re spending 500 hours a year on dating apps with nothing to show for it, that’s $50,000 of your time.

Stack on app fees, bad dates, and wasted weekends — a $10,000 engagement that actually finds your person starts to look like a bargain.

Round 2: Donate a Business Idea

Chandler’s advice: go extreme one way or the other. Everything in the middle is getting disrupted.

Go Extreme Analog: Pressure Washing

Start local, knock on doors, and you could hit $10,000/month on nights and weekends.

Startup cost is $300–$400 — you break even after your first job.

Low competition, no algorithm, AI-proof, and naturally viral (one clean driveway and the neighbors notice). Chandler did this as a kid.

Go Extreme Digital: AI Implementation

Target the most outdated, inefficient service businesses and come in as their AI implementer. Pitch: “I help businesses grow their margin and profit using AI.” Find the pain closest to revenue and solve it.

Chandler paid one person $2,000/month for 24 months for a custom AI lead follow-up tool — that person then sold the same solution to other clients.

The key: don’t be a generic AI consultant. Niche down to one specific problem, get two or three clients on retainer, and you’ve replaced a full-time income.

Chandler’s 4-P framework for the offer:

Person – who exactly are you helping?
Pain – what problem do they already know they have?
Promise – what outcome can you deliver with AI?
Price – what’s the right number for that customer?

Round 3: Tripe Threat

Marketing Tactic That’s Working Right Now

Partnerships.

SelfPublishing.com is on track for $6–8 million from JV webinars and events this year.

A winning formula: 500+ attendees, $10k investment, $50–100k in sales.

Before any partnership, ask: “Did this audience already do the thing?” Prior experience with the topic means dramatically higher conversion.

Favorite New Tool

Lovable + Claude. His team built a custom AI sales manager that reviews every sales call, scores reps, and sends coaching feedback automatically.

The month after launching it: +$500,000 in sales over the prior month.

Favorite Book from the Last 12 Months

The Surrender Experiment – A yogi stops forcing outcomes and accidentally builds a billion-dollar software company. Chandler called it “very anti-Chandler” — which is why it hit.
Am I Being Too Subtle? – Another contrarian take on building a business on your own terms.

Chandler’s #1 Side Hustle Tip

“Don’t let other people tell you how to live.”

Episode Links

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