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From Zero to Side Hustle
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Knowing we’re in the same month as Thanksgiving
🏀 The NBA season opened last week. I caught the first quarter of the Knicks game before work pulled me away.
Early-season basketball tests the system. So do the first 90 days of a business. Real customers show you what works and what doesn't.
This week: four businesses that found their model by doing the work.
Grab a fork.
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Check this out
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Three Executive Clients, $10,500 a Month, No Employees
WHAT’S THE PROBLEM?
A busy executive needs an assistant but often doesn't need one full-time — they need 10 to 20 hours a week of calendar management, email triage, travel booking, and coordination. Hiring a full-time employee costs $70,000 to $90,000 a year in salary and benefits. A fractional assistant charges a monthly retainer, serves multiple clients, and gives each one exactly the hours they need.
The buyer already knows what they want. They just don't know where to find someone they trust.
That's the gap: The work is the same as a traditional EA role. The model is fractional, and the math is completely different.
WHAT’S THE BIG IDEA?
You sign three to five clients at $1,500 to $5,000 a month each depending on scope. Three clients at an average of $3,500 is $10,500 a month. You provide all the services a full-time EA does, but each client gets a defined hours package and you manage the schedule to serve all of them without overlap.
The business charges for access and expertise. But it grows through referrals: every executive knows other executives who have the same problem.
► One fractional EA in this range carries three to five clients at $1,500 to $5,000 a month each. Belay, which places over 9,000 virtual assistants across the U.S., lists senior EA support at $50 an hour: 10 hours per client per week clears $2,000 a month. Three clients at a mid-range rate of $3,500 each is $10,500 a month.
Zooming out: The fractional model works because executives pay for problems solved, not hours logged. When travel runs smoothly and the inbox stays clear, clients aren't counting hours. They're paying for peace of mind.
🥢The winners will be operators with a background in a specific executive's world — finance, law, technology — who already speak the vocabulary: context fluency is what the client is actually paying for.
🍜 The risk is scope creep: each client will push for more over time. A written contract with a defined monthly hours cap is the only protection. Without one, three clients becomes three full-time jobs.
You might also like ⇢ How to Start a Virtual Assistant Business
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What's your take?
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The Substack Paywall
Anfernee Tan writes Solopreneur Code, a Substack newsletter for people building solo businesses. He had 6,421 free subscribers and was not converting them to paid at any meaningful rate.
The recipe: Where in the post the paywall appeared. Most writers put the paywall at the end — after readers have consumed the full value of the free content. By that point, the reader feels satisfied and has no reason to pay for what they already got. Anfernee moved the paywall earlier, to the point of highest interest in the post — right before the key insight, not after it. Free content became the setup; paid content was the resolution.
The result: 108 paid subscribers at $29 a month — $3,132 in monthly recurring revenue — with no launch, no promotion, and no new subscribers.
The recipe has two moves: write a post where the key insight comes after a clear point of tension, then put the paywall at that tension point instead of at the end.
If you run any paid newsletter: pull up your last five posts and mark where the paywall sits. If it is after the reader already has the answer, move it. Then check your conversion rate in 30 days.
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The holiday streaming season is almost here
Are you ready? As revealed in our holiday playbook, Roku Ads Manager lets you easily set up, measure and optimize your self-serve holiday ad campaign. You can even create a shoppable ad unit that lets streamers buy directly from their remote.
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Why 2,300 Orders Came Without Paying for a Single Ad
Most Etsy sellers who make jewelry think the product is the business.
Lindsay Gottschall and Courtney Bleier launched Ann + Joy in January 2018 and found out the business was in the buyer's name on each piece.
What they uncovered: Ann + Joy makes handmade, personalized jewelry — names, dates, and initials stamped or set into each item. In year one, with no paid advertising, they filled 2,300 orders and brought in over $65,000. By early 2019 they had added custom preservation jewelry — taking dried flowers from a wedding or a funeral and incorporating them into a wearable piece.
The mistake most Etsy jewelry sellers make: they launch a collection and hope the photos do the work. Personalization changes the comparison set entirely. A plain ring competes against every other plain ring. A ring with your grandmother's name on it competes against nothing else.
What they learned: Personalization is a defense against the price race. The customer can find a cheaper ring. They cannot find a cheaper version of the ring that has their specific person's name on it.
The first buyer to build for is not "people who like jewelry." It is the person with a milestone coming — a wedding, a birth, a graduation — who wants something that could not have been made for anyone else.
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Hungry yet?
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Unlock up to $2 million licensing your company data
Have a business larger than 20 people that lives on Slack and is older than a year? Companies like Micro1 want to pay $100k - $2 million to license your data. They anonymize it and then use it to train the next set of frontier AI models.
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Enough talk. Go cook.
That's Monday. Reply and tell us which idea you'd actually run. We read every one. See you tomorrow.
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