Discover five unique businesses that have something worth stealing.
Chandler Bolt, the founder of SelfPublishing.com, returns to the Side Hustle Show after 12 years.
Having created an 8-figure business assisting countless individuals in writing and publishing books, Chandler shares insights on five innovative business concepts, ranging from a cake dropshipper to a virtual dating matchmaker.
Listen to Episode 746 of the Side Hustle Show to explore:
- How a cake middleman can earn up to $1,000 per day without operating a bakery
- Why a mobile dog gym excels in targeting the right customer
- What makes a virtual dating service one of the most profitable businesses to start
(Claim your Free Strategy Session at selfpublishing.com/sidehustle for a consultation on your book idea)
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Round 1: Wild Business Ideas
Cold Caking: The Cake That Books Meetings
William Lindholm’s Daymaker.com offers a cake-based lead generation service, sending custom cakes to sales prospects and generating around $4,000 per day in revenue with 30% margins, resulting in a $1,000 profit per day.
Operating as a middleman without a bakery, Lindholm forms partnerships with bakeries to maintain the margin.
The Numbers
- Each cake costs $80
- Conversion rate from cake delivery to booked meeting: 35% (compared to 1% for cold email)
- At a 33% conversion rate, that’s approximately $240 per meeting
- Converting one in four meetings into a sale results in a $1,000 cost per customer
- If the product value exceeds $5,000, the economics are favorable
How It Started
Lindholm’s initial business involved delivering birthday cakes to HR departments on auto-subscription, automating cake deliveries for team birthdays.
The transition to an outbound sales tool occurred later, sparked by a viral stunt of sending a 100-piece, pitch-deck-themed cake to major VC firms, leading to increased interest.
Mobile Dog Gym: A Luxury Workout for Your Pup
Run Buddy Mobile operates an air-conditioned Mercedes Sprinter van equipped with custom non-motorized dog treadmills outside clients’ homes.
A 30-minute session costs $70, with 90% of clients booking recurring weekly slots. The service is fully booked, with franchise expansion underway and a new location opening in Austin.
The Business Model
- Launching one van costs over $110,000 (including a $70k Mercedes Sprinter, $25k custom treadmills, and wrap)
- The fleet now has 7 vans in Arizona
- With 900,000 TikTok followers, the vans serve as mobile billboards
- Trainers are certified through Run Buddy University
The high startup cost and reliance on volume due to the lower price point necessitate strong operations. The niche of luxury dog gym services in a Mercedes sets them apart from traditional dog-walking businesses.
A segment of existing dog-walking clientele is willing to pay significantly more for a premium service like this, making them valuable targets.
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 from historical settings, reacting to events from a modern perspective.
In just three months, the channel has gained 17 million views and earns an estimated $8,000 per month from long-form content.
The Business Model
While Chandler appreciates the concept, he criticizes the reliance on ad revenue alone, emphasizing the need for a backend product for sustained profitability.
He suggests a strategy similar to Mr. Beast’s Feastables, where YouTube serves as a customer acquisition channel for underlying brands rather than the primary business.
Chandler’s team at SelfPublishing.com already leverages AI avatars from HeyGen to update course content efficiently as algorithms change.
Cardboard Cat Condos (and the Pivot to Wool)
Observing her mother’s cats’ preference for Amazon boxes over furniture, one entrepreneur developed decorative cardboard condos shaped like gingerbread houses, milk boxes, cheese wedges, and haunted houses.
The business has evolved into a six-figure enterprise, selling through their store, Amazon, and wholesale channels via Faire.
The Pivot and Opportunity
Due to high shipping costs for cardboard condos, the business transitioned to sustainably sourced wool cat toys made by a Fair Trade craft guild in Nepal, retailing for $17–$25 and offering higher margins.
Sales are divided among their website, Amazon, and over 100 stores across the U.S. and Europe through wholesale agreements, with a focus on recurring consumables like a monthly cat toy subscription.
Chandler highlights Dr. Squatch’s men’s soap subscription model as a reference for maintaining minimal SKUs and predictable cash flow.
Virtual Dating Service: High-Margin Matchmaking at $1,200–$3,000/Month
Vida Select, operating for nearly two decades, boasts an 82% success rate and 11,000 relationships facilitated.
They offer services ranging from optimizing dating profiles to filtering matches, charging $1,200–$3,000 per month to help singles find meaningful connections efficiently.
Market Insights
- Online dating in the U.S. generates around $3 billion annually
- With approximately 30 million active daters in the U.S., most platforms offer commoditized services priced at $20–$100 per month
The business reframes the value proposition by emphasizing the time and money saved by using their service, making the fees a worthwhile investment for clients seeking genuine connections.
Round 2: Donate a Business Idea
Chandler advises aspiring entrepreneurs to pursue extreme approaches in business innovation, either by going analog or digital to disrupt traditional practices.
Go Extreme Analog: Pressure Washing
By offering pressure washing services locally, entrepreneurs can earn up to $10,000 per month on evenings and weekends with minimal startup costs and high demand.
With low competition, no reliance on algorithms, and inherent viral marketing potential, this business model is accessible and profitable.
Go Extreme Digital: AI Implementation
Entrepreneurs can target outdated service businesses by offering AI implementation services to enhance margins and profits through automation.
Specializing in solving specific pain points with AI solutions, entrepreneurs can secure retainer clients and achieve sustainable income streams by addressing critical business needs effectively.
Chandler outlines a 4-P framework for crafting compelling AI offers tailored to clients’ needs.
Round 3: Tripe Threat
Marketing Tactic That’s Working Right Now
Partnerships have been instrumental in SelfPublishing.com’s success, with projected revenues of $6–8 million from joint ventures, webinars, and events this year.
Successful partnerships leverage existing audience engagement to drive sales, emphasizing prior audience engagement with related topics for higher conversion rates.
Favorite New Tool
Lovable + Claude, a custom AI sales manager developed by Chandler’s team, has significantly boosted sales by providing automated sales call reviews, rep scoring, and coaching feedback.
The tool’s impact was immediate, resulting in a $500,000 increase in sales compared to the previous month.
Favorite Book from the Last 12 Months
- The Surrender Experiment: A transformative story of building a billion-dollar software company by surrendering to the flow of life, resonating with Chandler’s entrepreneurial journey.
- Am I Being Too Subtle?: A contrarian perspective on building businesses authentically and on one’s terms.
Chandler’s #1 Side Hustle Tip
“Don’t let external influences dictate your life choices.”
Episode Links
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