Hey hustler,

Some really good finds this week. A couple from the news, a couple straight from Reddit, and one data point that surprised me. Let's get into it.

Julia Holden, 34, from New Jersey, noticed that her newborn son fell asleep faster when his eyes were gently covered with a burp cloth. She looked for a product that did this and couldn't find one, so she made it herself.

She designed a baby hat with a built-in eye covering, called it Sleepy Hat, and spent about $16,000 from her savings to get it off the ground. She did all of this while working full-time at an advertising company, squeezing in work on the business in 20-minute windows between breastfeedings.

The first year was slow. She made less than $2,000 in total sales. But after listing on Amazon and gaining traction on TikTok in 2025, things took off. By December, Sleepy Hat brought in over $90,000 in a single month. She quit her $95,000/year job to run it full-time, and the business is now profitable with two part-time contractors on staff.

The thing that makes this story stick is how unglamorous the beginning was. She wasn't following a playbook. She noticed a problem, couldn't find a solution, and built one herself during the messiest season of her life.

🔗 Read the full story on CNBC Make It

Ashley Alicea is a 33-year-old charter school teacher in New York City. On top of her full-time teaching salary of $90,000/year, she works as a mental health counselor on Tuesdays, Wednesdays, and Thursdays after school, seeing six to eight clients a week at $55 an hour. That side hustle brings in about $1,500 a month, and she's using almost all of it to pay down $61,000 in remaining student loans from grad school (she originally took out $92,000).

What I like about Ashley's approach is how deliberate she is with boundaries. She caps her side hustle at eight hours a week so she still has time to cook, go to the gym, walk her dogs, and take care of herself. A few years ago she was earning $50,000 as a preschool teacher and couldn't afford her own apartment. Now she has savings, an emergency fund, and a clear plan to get out of debt.

This one resonated with me because it's not a flashy overnight success. It's someone using a skill she already has, on a schedule she controls, to steadily change her financial situation.

🔗 Read the full story on CNBC Make It

This one came from r/sidehustle this week and I couldn't stop thinking about it. A guy got into mindfulness after reading The Power of Now by Eckhart Tolle, and eventually designed a watch that doesn't show the time at all. It just says "NOW" on the face.

He started the business about 8 years ago. For the first 5 years it made almost nothing, just occasional orders from people into mindfulness, meditation, and yoga. Then one day an influencer posted it, and things started to snowball. Creators reached out about collaborations, and orders picked up. Now it does $1,500 to $2,000 a month in slower periods and up to $10,000 a month during holiday season or around collaborations. The simplest version, the one that literally just says "NOW" with no time display at all, outsells everything else.

I love this story because the product is so wonderfully weird and specific. It's a watch that doesn't do the one thing a watch is supposed to do. And it took five years of almost zero sales before it caught on. Sometimes the most oddly specific ideas are the ones that eventually connect with people.

🔗 See the original post on r/sidehustle

Another one from r/sidehustle this week. A software developer spent about a year building small mobile apps on the side. Nothing groundbreaking. Mostly health and habit trackers like a sobriety tracker, a supplement tracker, and an anxiety tracker. He now has 14 apps live on both iOS and Android.

For the longest time he was barely making $10 a day because he was selling features as one-time purchases for around $5. Then about a month ago he switched everything to subscriptions and revenue jumped almost immediately. He just crossed $1,000 in the last 28 days, with Sober Tracker alone making over half his income. His newest app, Supplement Tracker, started earning within two weeks of launch.

His biggest tip was almost too simple: name your app what people actually search for. "Sober Tracker" instead of some clever brand name. Boring, but it works for app store rankings.

I thought this was worth including because the numbers are honest and modest. He's not claiming $50K months. He's a developer who spent a year experimenting, found what worked, made one smart pricing change, and crossed a real milestone. That's what most side hustles actually look like.

🔗 See the original post on r/sidehustle

This one surprised me. According to an analysis by Falcon Digital Marketing that was covered by Inc. a couple of weeks ago, search interest in freelance writing as a side hustle grew 5,546% year over year. That's the biggest jump of any side hustle they tracked.

When ChatGPT launched, everyone assumed freelance writing was finished. Why pay a human when AI can produce a blog post in 30 seconds? But three years later, the opposite happened. AI flooded the internet with so much generic content that brands and publishers are now paying premium rates for writers who sound like real people with actual opinions and lived experience.

Specialist writers in niches like B2B SaaS are earning $0.30 to $0.95 per word, and healthcare writers with credentials can command up to $1.25 per word. Part-time freelance writers are reporting earnings of $2,000 to $5,000 per month.

I wanted to include this because it's a genuinely counterintuitive story. The tool that was supposed to kill writing actually made good writing more valuable. If you can write well and you know a subject deeply, there's probably more demand for your work now than there was two years ago.

🔗 Read the Inc. article on the fastest-growing side hustles of 2026