7 min 36 sec

Letters-from-Santa Hustles Down Chimney

A month-long, part-time project writing personalized letters from Santa Claus earns $6,000.
Holiday Special Niche Ideas Seasonal Service Writing

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What It's About

Personalized letters from Santa jingle all the way to a D.C. woman's bank account!

Business Model
Skills Required
Writing & Organization
Profit Potential

Words of Wisdom

After initially launching her letters from Santa service, Bry noticed that she wasn't receiving much traction, so she reevaluated her service and made a couple changes. The first was personalization. She would learn key things about a child from a list of questions and personalize the letter, making sure they knew Santa was watching and that he was proud of them (most of them). The parents also got to approve the letters, which was a huge comfort for them (they didn’t want to be on the hook for something “Santa” promised). 

But here’s the winning element: Bry started to advertise that these deluxe letters included reindeer food. What parent who loved Christmas didn’t want to watch their child leave out magic reindeer food on Christmas Eve? This was apparently the Santa letter jackpot!

Fun Fact

I often ask people what the greatest thing about their hustle is, and Bry had an interesting answer. She said:

"That’s easy. A side hustle gives you extra purpose. I love focusing my extra energy on something I built from the ground up. I love when my work makes others happy. I get hundreds of emails from parents each year with pictures of their children, beaming with their Letters from Santa and baggies of reindeer food. It’s fulfilling to know that the work you have complete ownership of it means something to people."

I couldn’t have said it better myself!

Notes from Chris

Episode 338
Santa Claus might sit around and get fat 11 months of the year, but come December, this jolly old man becomes overwhelmed. Even in our hyper-connected world, where there is so much interest in Santa (seriously, his social media is blowing up) a lot of people still communicate with Santa using an old-school social network called letter-writing.

For the millennials and Gen-Z listeners out there, I should probably explain a little—people used to actually hand-write on pieces of paper and then put them in the mailbox, not the outbox where you click “send,” but an actual envelope. And then they used Stamps.com to send that envelope off to other people, who would receive it at the glacially slow pace of several days later. And in fact, when it comes to writing to Santa, some people still use this antiquated system.

That’s where our story comes in—I was recently informed that one of his assistants is a fan of the show.

Right out of college, Bry Larrea spent all of her savings on a four-month backpacking trip. Upon her return, she got a job as a waitress in Yakima, Washington while her boyfriend at the time worked on a campaign. She was only working part-time though, so she didn’t have a lot of money. But more importantly, she was so bored. She knew she wanted to start a side gig, but what?

She sat down and asked herself: "what am I good at?" She knew she was a fairly strong writer, but what could she sell that included her writing? And furthermore, what would people actually pay money for? She didn’t have time to write a book. She had already tried her hand at writing resumes… that didn’t go very well. What could she do?

She’s not completely sure how the idea showed up, but she started advertising handwritten Santa letters through her service, Letters from Santa.

The first year, she sold around 300 letters at $9.95 each or a deluxe package at $11.95. The letters cost her about $1.50 each to write and package, so she made around $4,000.

The second year (2015), she sold about 400 and raised the prices slightly (to $11.95 and $13.95). However, she outsourced the writing of the letters using Upwork.com, so her profit margin was slightly less. This time they cost about $3 to write and package.

Last year, something interesting happened. After first thinking she wouldn’t do it again—because even with the outsourcing, it was a lot of work—she finally decided to go for it, but started late and did very little marketing. However, here’s the surprise: she raised her prices to $19.95 and $26.95, so in doing less work, she actually made a lot more money. By selling 250 letters she made just under $6,000. This is all less than a month’s part-time work; she begins the process around Nov. 15 and letters are sent by Dec. 5-10.

Ho, ho, ho, and congratulations, Bry, on such an awesome capitalist Christmas project!


  • Letters from Santa: Embrace the magic of Christmas and head to Bry's website to see her personalized letters from Santa!
  • Upwork: The online gig platform that Bry used to outsource the writing of her Santa letters

Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,

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Quote of the Day
"Find something you’re good at and run with it. Build fast while you have momentum, even if you don’t know what in the world you’re doing because the truth is, none of us know what we’re doing. You don’t have to have all the answers in order to start!"
—Bry Larrea #SideHustleSchool

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Chris Guillebeau