100 Days of Side Hustle School: 101 Real Stories

The first 100 days

On January 1, 2017, I began a new project: to publish a story every day of someone who starts an income-generating project (a “side hustle”) without quitting their day job.

The project failed and I decided to give up. Just kidding! We are relentlessly moving along, publishing story after story—and it’s getting better and better!

I recently completed the first 100 days. There’s much more to come, but I’m excited about everything I’ve learned since beginning back in January.

The archive below is a snapshot of those first 100 episodes. For current stories, visit the complete episode archive.

Ep. 6 (L): Astrology Calendar Hustle. Ep. 4 (R): Pinning for Cash!

Side Hustle School – Week 1:

• Ep. 1 – Create a New Source of Income without Quitting Your Job: In this very first episode, learn what side hustles are all about. Every day for the next year, you’ll hear a different story on how someone like you has been able to start their hustle. I’ll share how they got their idea, how they developed it, the challenges they overcame along the way, and even how much money they’ve made.
• Ep. 2 – British Man Earns $700/Month Writing Fish Tank Reviews: How a British man wrote a series of reviews about fish tanks and ended up building a completely passive income business as an Amazon affiliate. He now earns $700/month without doing anything for it at all.
• Ep. 3 – Candy Heart Hustle Becomes Six-Figure Second Income: After being unable to find branded candy hearts for a client, a marketing executive decides to create her own. And she creates a high profit, seasonal side income in the process. [↓]
• Ep. 4 – Oil & Gas Sales Rep Makes $40,000 Reposting Online Photos: After jumping on the Pinterest bandwagon, a natural gas sales rep learns how she can turn pins into cold, hard cash in her spare time.
• Ep. 5 – How One Man Used a $100 Microphone to Make Over $8,000: After testing the waters with low-priced services on Fiverr.com, a Tennessee IT manager learns to focus on voiceover services for overseas customers.
• Ep. 6 – Single Mom Makes $15,000 Selling Astrology Calendar: After realizing that all of the astrology calendars in the market featured similar designs, a former restaurant owner decides to create her own.
• Ep. 7 – WEEKLY RECAP: Where to Find Hustle Ideas: In this first weekly recap, we’ll highlight the lessons learned in the first week of Side Hustle School. You’ll also learn how to get started finding your hustle idea.

Ep. 12 (L): San Francisco Traveling App. Ep. 10 (R): Saddles for Chickens!

Side Hustle School – Week 2:

• Ep. 8 – Cruise Vacation Turns Into Highly-Profitable Hustle: After searching for answers to questions about his first cruise, a copywriter decides to take matters into his own hands by creating an informative blog.
• Ep. 9 – The Craigslist Wedding Photographer: A California government employee becomes a part-time wedding photographer after posting an ad on Craigslist in order to gain experience before shooting .
• Ep. 10 – Saddles for Pet Chickens: Get Ready to Wing It!: After the loss of a beloved family pet, an engineer creates a specialized product business in a very unconventional industry with almost $0 in manufacturing costs.
• Ep. 11 – Ketogenic Cookbook Author Makes $1,000 the First Day: After striking out on a new ketogenic lifestyle, one woman creates a $2,000/month side hustle sharing tips and recipes on her blog.
• Ep. 12 – 40,000 People Use This Web Developer’s Side Hustle Every Day: How a San Francisco commuter became part of the original iPhone launch with a hustle that now helps more than 40,000 people every day.
• Ep. 13 – Waldorf Teacher Designs Curriculum for Other Educators: How a teacher uses what she knows to create PDF lesson plans to help other teachers save time and teach more effectively.
• Ep. 14 – WEEKLY RECAP: What Makes a Good Hustle: In the second weekly recap, we’ll highlight the lessons from this week of Side Hustle School and focus on one quality that sets good hustles apart from the rest.

Ep. 17 (L): Airbnb for dogs. Ep. 15 (R): Digital caricature hustle.

Side Hustle School – Week 3:

• Ep. 15 – Graphic Designer Learns to Draw Caricatures for $250/Hr: How a graphic designer went from $8 an hour to $250 an hour in her side business. She now earns more than $100,000 working part-time — and she has some great advice that applies to a lot of hustles.
• Ep. 16 – Homemade Gin Kit Sells 75,000 Units: After encountering a roadblock trying to start their own distillery, two friends create a side hustle that allows others to make gin in the comfort of their own home—and it’s a huge success!
• Ep. 17 – “Airbnb for Dogs”: Woman Hosts Pets at Her Home for $200/Day: After moving to the states to be with her new husband, a nutritionist from Spain decides to host other people’s pets in her home.
• Ep. 18 – College Student Generates 50M Views on YouTube, Hires 13 Employees: After seeking a method to conquer her own skin issues, one woman takes to YouTube to help others shed their skin insecurities as well. Five years later, she has her own multi-million dollar skincare line serving people all over the world!
• Ep. 19 – Government Analyst Builds Six-Figure Reselling Business: How a senior program analyst for the government goes from collecting Frequent Flyer miles to earning a high side income buying and reselling through the “Fulfilled by Amazon” program.
• Ep. 20 – Engineer Creates “Inertia Project” for Women: How a former engineer loses in Las Vegas and redesigns the trajectory of her life, creating an impressive hustle empowering other women to take control of their lives and habits in order to live more healthy and fulfilling lives.
• Ep. 21 – WEEKLY RECAP: Why Some Hustles Are Better than Others: In this third weekly recap, we’ll highlight the lessons learned in this week of Side Hustle School, and you’ll also learn why some side hustles are better than others.

Ep. 24 (L): Philanthropic Cashmere Hustle. Ep. 25 (R): Pottery Barn Photography Hustle.

Side Hustle School – Week 4:

• Ep. 22 – 17-Year-Old Canadian makes $7,000 From Holiday Pop-up Shop: Having grown up with an interest in entrepreneurship, a high school student starts a holiday pop-up shop that earns $7,000 in just one month.
• Ep. 23 – Guitar Teacher Sells Lessons on Craigslist and Makes $80/Hour: How a very busy, new father created a part-time hustle teaching guitar lessons for $80 an hour and has been able to turn it into a full-time income.
• Ep. 24 – Honeymoon in Nepal Becomes Fashion Accessories Business: A multinational love affair turns into a global side hustle in the fashion world that also raises money for charity in Nepal.
• Ep. 25 – Pottery Barn Commissions Art from Independent Photographer: How an independent photographer ended up creating a hustle that brings in a third of her total income.
• Ep. 26 – These Resume Templates Make $462/Month in Passive Income: Student creates a visual resume service to make extra cash, then transitions that service to work smarter, not harder. It now brings in $462 in month in completely passive income.
• Ep. 27 – Stressed-Out Mom Gives Up TV to Launch Her Hustle: How a San Diego accountant coping with the struggles of new motherhood launched her own private label wine hustle for stressed out parents like herself.
• Ep. 28 – WEEKLY RECAP: Good Fortune Favors the Prepared: In our fourth weekly recap, we’ll highlight the lessons learned in this week of Side Hustle School, and you’ll also learn why fortune favors those who come prepared.

Ep. 33 (L): Handmade State Slates. Ep. 31 (R): Ballpark Sweaters!

Side Hustle School – Week 5:

• Ep. 29 – Hospital Database Programmer Outsources His Skills: How a hospital employee utilizes skills that he learned from work to help others work with and process complex computer programs and information earning over $100/hour.
• Ep. 30 – Ohio IT Director Earns $31,000 Setting Up WordPress Sites: How an Ohio IT director earned more than $31,000 empowering others by providing them with the tools and resources they needed to set up their own websites.
• Ep. 31 – A Visit to the Ballpark Inspires a Unique Fashion Item: A couple decides to go into manufacturing novelty baseball sweaters after receiving a lot of attention about them at a baseball game.
• Ep. 32 – Make $4,000/Month Renting Out Cars You Don’t Own: How a Los Angeles man leases a fleet of 16 cars and rents them out at a higher rate making over $4,000/month.
• Ep. 33 – GE Engineer Sells Hand-Crafted Slate Artwork to All 50 States: A GE engineer uses his skills to make and sell hand-crafted slate artwork to all 50 states. In addition to bringing in a great side income, it’s also given him more courage and security to make decisions at his day job.
• Ep. 34 – Real Estate Consultant Fills Apartment Buildings with Original Artwork: How a woman in Seattle who works as a real estate project manager during the day started a side hustle that literally appeared in front of her. After making $12,000 from that first year-long hustle, now she’s building it into a mid-sized business that she hopes will replace her day job income.
• Ep. 35 – WEEKLY RECAP: Observation, Validation, and Leasing 16 Cars: In our fifth weekly recap, we’ll highlight the lessons learned in this week of Side Hustle School. Also: the SHS workshop series is underway this week! Tell me where I should go next.

Ep. 38 (L): Astronomy Book Hustle; Ep. 40 (R): TLC Officiant Hustle

Side Hustle School – Week 6:

• Ep. 36 – Fitness Pole Dance Studio Grows to 4 Locations: How a graphic designer started a pole dancing fitness studio, expanded it to multiple locations, and grew it to a six-figure income before quitting her job.
• Ep. 37 – American Expat Coaches Families Who Move Overseas: After living in multiple countries with his family, a technical writer creates a service to help guide other families looking to begin a similar experience.
• Ep. 38 – Tour Guide Sells Astronomy Books to Tourists: How a British software engineer moved to the Canary Islands, started working as a tour guide, and wrote her own guidebook to accompany her tours.
• Ep. 39 – “Live Snoop” Service Helps Parents Monitor Their Kids’ Internet Use: How an IT graduate created a web-based service that provides peace of mind to parents with children growing up in the era of technology.
• Ep. 40 – Chicago Psychotherapist Becomes Ceremonial Wedding Officiant: After being featured on TLC, a Chicago psychotherapist and marriage counselor becomes a ceremonial wedding officiant.
• Ep. 41 – USPS Mail Carrier Makes Clay Imprints for New Parents: How a USPS mail carrier and court interpreter created an $800/month hustle serving new and expectant parents.
• Ep. 42 – WEEKLY RECAP: Pole Dancing and the Expat Life: In our sixth weekly recap, we’ll highlight the lessons learned in this week of Side Hustle School. Also: we added four new stops to the Side Hustle workshop series: Austin, Denver, Los Angeles, and San Francisco. Sign up now before we sell out!

Ep. 45 (L): The SimpleBra; Ep. 48 (R): Next-Level Tarot Hustle

Side Hustle School – Week 7:

• Ep. 43 – Miserable Day Job Turns Into $100,000 Side Income: An education district employee follows her passion for writing and creates an online side hustle raking in over $100,000.
• Ep. 44 – Charter Bus Employee Creates PR Service for Bloggers: How a digital marketer created something for himself, then decided to try selling it other people who had the same needs. He now makes more than $2,500 a month from this side project.
• Ep. 45 – UX Designer Creates “SimpleBra” to Help Women Feel More Comfortable: How a UI/UX designer scratched an entrepreneurial itch and used $15,000 of her savings to create a side hustle manufacturing bras for women looking for an alternative to the push-up bra.
• Ep. 46 – The Live Cricket Drop-Shipping Hustle: Yep, it’s true: a Pennsylvania man makes $700+ a month drop-shipping live crickets to reptile owners across the country.
• Ep. 47 – Gallup Coach Creates StrengthsFinder Mugs: No two StrengthsFinder profiles are the same, so a Gallup-certified coach learns to make and ship personalized mugs.
• Ep. 48 – New Yorker Doubles Her Income with Next-Level Tarot Cards: How a senior designer for a feminist media publication decides to create tarot card decks and ends up making as much with her side hustle as she does at her day job.
• Ep. 49 – Weekly Recap: Live Crickets, Tarot, and Reinventing the Bra: In our seventh weekly recap, we’ll highlight the lessons learned in this week of Side Hustle School. I’ve also included a quick exercise to help you generate ideas based on your interests.

Ep. 50 (L): Belgian Chocolate Hustle!; Ep. 52 (R): Spa-Grade Face Paint

Side Hustle School – Week 8:

• Ep. 50 – Belgian Fine Chocolate Comes to America: After living in Belgium for 13 years, a Louisiana freelancer starts a seasonal side hustle making fine chocolate out of his home. It brings in close to $8,000 in the first year of business!
• Ep. 51 – “Cheap Plane Tickets” Site Becomes Million-Dollar Hustle: How a Washington, DC political analyst used research skills to help travelers save money while attracting 275,000 email subscribers and making more than $1M.
• Ep. 52 – Facebook Photo Leads to Today Show Appearance: An elementary school teacher on a mission to introduce a non-toxic product for school rallies and sporting events makes it on the TODAY show.
• Ep. 53 – Queer Punk Artist Starts Personal Finance Workshop: A manager for a non-profit organization who describes herself as a queer punk artist creates a series of personal finance classes.
• Ep. 54 – Penny Portraits of Abe Lincoln Turn Into $40,000: An investment marketer creates a poster portrait of America’s 16th president. Since debuting his design, it’s sold more than 4,000 units and made $40,000.
• Ep. 55 – T-Shirts on Amazon Make $17,000 in a Month: A former corporate employee in Ireland runs a merchandising hustle on Amazon.com that brings in as much as $17,000 in profit in a single month. She does this with no inventory, no risk, and no paid traffic.
• Ep. 56 – WEEKLY RECAP: Plane Tickets, Punk Art, and Abe Lincoln: In our eighth weekly recap, we’ll highlight the lessons learned in this week of Side Hustle School. Also: more listener Q&A!

Ep. 58 (L): 50 Shades of Grey Hustle; Ep. 62 (R): Gold Panning in New Zealand!

Side Hustle School – Week 9:

• Ep. 57 – Microsoft Employee Teaches Hula Hooping, Goes on Local News: After using hula hoop fitness to get back into shape, a Microsoft specialist finds a way to earn $800/month teaching classes and helps others do the same.
• Ep. 58 – 50 Shades of Grey Inspires Bedroom Items Hustle: A chemical engineer capitalizes on the 50 Shades of Grey craze by creating a collection of adventurous products, all hidden in a series of ordinary-looking books.
• Ep. 59 – PE Teacher Makes $11,000 with Membership Site: A PE teacher starts a blog that makes more than $11,000 through a sustainable revenue model that will likely grow with each passing month.
• Ep. 60 – Marketing Consultant Creates Private Retreats: In the foothills of Tennessee, a marketing consultant designs a quarterly, high-end retreat weekend to help attendees take stock of their lives and businesses.
• Ep. 61 – Mom-Founded Startup Rents Infant Gear to Tourists: Busy mom in Chicago uses a peer-to-peer sharing platform to earn extra money for her family and help visiting parents get all the baby gear they need for their trip.
• Ep. 62 – Elementary School Teacher Pans for Gold in New Zealand: After changing continents multiple times, an elementary school teacher finds true love, settles down in NZ, goes panning for gold, and ends up making $40,000/year working mostly on the weekends.
• Ep. 63 – WEEKLY RECAP: 50 Shades of Hustling: In our ninth weekly recap, we’ll highlight the lessons learned in this week of Side Hustle School, answer some listener questions, and discuss starter platforms that you can try out today!

Ep. 68 (L): Novelty Pocket Shirts; Ep. 65 (R): Self-Published Romance Novels

Side Hustle School – Week 10:

• Ep. 64 – Long-Haired Men Create Tribal Identity: Two guys nurture a supportive community based on the unique shared identity of men with long hair and create “Hair Ties for Guys.”
• Ep. 65 – Finance Employee Sells 200,000 Self-Published Romance Novels: When she can’t find anything good to read, a finance employee starts writing romance novels of her own. The books go on to sell hundreds of thousands of copies and pull her family out of debt.
• Ep. 66 – Accountant Starts Net-Zero Personal Finance Hustle: An accountant finds a way to bridge the gap between financial advisers and tax professionals by transferring some of the skills from his day job to his own self-employed income.
• Ep. 67 – A Life of Travel Leads to a House-Designing Hustle: A Pacific Northwest couple travels full-time but still brings in over $60,000/year designing “tiny” houses and alternative living spaces.
• Ep. 68 – Alcohol Fueled Idea Sells Over 1,500 Shirts in Less Than a Year: After a night at the bar, three friends come up with an idea to add huge pockets to the front of t-shirts.
• Ep. 69 – NYC Jazz Musician Builds $40,000/Year Blog: A musician finds financial freedom by growing a blog and starting an e-course teaching other people how to play jazz.
• Ep. 70 – WEEKLY RECAP: Tiny Houses, T-Shirts, and Romance Novels: In our tenth weekly recap, we’ll highlight the lessons learned in this week. Also: more listener Q&A!

Ep. 75 (L): British Pork Pies; Ep. 76 (R): Whimsical Sketch Hustle

Side Hustle School – Week 11:

• Ep. 71 – Woman Earns $7,000 in Three Days by Selling Glass Nail Files: How an impromptu trip to a local farmer’s market leads one woman in California to a sustainable six-figure side hustle selling glass nail files online.
• Ep. 72 – College Lecturer Makes Money by Helping Other Instructors Teach Better: How a woman who uses skills she learned in her day job as a college lecturer to instruct other teachers how to be more successful in the classroom.
• Ep. 73 – Florida Man Earns $100,000 Selling T-Shirts with No Inventory: There’s more than one way to make a lot of money designing and selling t-shirts without actually keeping them on hand. In today’s story, an app designer earns six-figures with a print-on-demand service.
• Ep. 74 – Tango Adventures in Buenos Aires: After traveling to South America, an American woman falls in love with tango and creates a group experience to teach others.
• Ep. 75 – British Pub Manager Bakes Pork Pies for Profit: A British pub manager has a creative idea for new pub food that he initially uses to help his boss but then realizes that it might be better for himself.
• Ep. 76 – Successful Artist Adds $1,000/Month to His Income: An artist uses his love of whimsical drawing to create a side hustle selling everything from autographed prints to coffee mugs with his designs on them.
• Ep. 77 – WEEKLY RECAP: Tango, Glass Files, and Pork Pies: In our eleventh weekly recap, we’ll highlight the lessons learned this week on Side Hustle School. Also: more listener Q&A!

Ep. 78 (L): Jewelry for Social Good in Detroit; Ep. 83 (R): Craigslist Bridesmaid-for-Hire

Side Hustle School – Week 12:

• Ep. 78 – Detroit Women Make Jewelry for Profit and Social Good: An attorney starts a jewelry company with purpose, employing disadvantaged women in Detroit to help them transition from a life of dependence into one of self-reliance.
• Ep. 79 – Worm Composting Empire Brings in $400/Month: Texas man stumbles upon a worm composting method that turns into an interesting hobby and a fun side hustle. Don’t let your hustle idea wiggle away!
• Ep. 80 – South Carolina Man Learns to Make Candles by Watching YouTube: Inspiration strikes in an upscale men’s store when a man comes across a line of handmade scented candles.
• Ep. 81 – Freelance Illustrator Helps Other Artists Sell Their Work: A successful illustrator creates a side business earning more than $25,000 a year by helping artists sell their work online.
• Ep. 82 – Bartender Writes Statewide Marijuana Guide: Colorado bartender sells 2,000 copies of a statewide marijuana guide in the boom of the budding cannabis economy.
• Ep. 83 – Bridesmaid-for-Hire Posts on Craigslist; Earns $20,000/Month: A Craigslist ad goes viral and becomes a six-figure business for an in-demand bridesmaid.
• Ep. 84 – School Administrator Creates Digital Magazine for Goaltenders: After discovering that his passion for goaltending has little to no online presence, a hockey fan decides to create his own resource blog.
• Ep. 85 – WEEKLY RECAP: Social Good, Marijuana, and the Worm Empire: In our twelfth weekly recap, we’ll highlight the lessons learned in this week. Also: more listener Q&A!

Ep. 87 (L): 20,000/Month Cleaning Hustle; Ep. 90 (R): Karaoke League Hustle!

Side Hustle School – Week 13:

• Ep. 86 – Car Enthusiast Sells $1 Million in Products Over 13 Years of Hustling: A car enthusiast follows up on his curiosity and creates a project that earns $5,000/month on average and has brought in over a million dollars after a decade.
• Ep. 87 – College Student Earns $20,000 a Month Cleaning Houses: A Washington, D.C. student identifies problems in the cleaning industry, then starts a customer service-driven company.
• Ep. 88 – Father of 9 Starts “Uber for Tutoring” Hustle: After being frustrated in his search for the right tutors for his many children, a busy father creates a directory that has generated more than 100,000 user profiles.
• Ep. 89 – College Bartender Turns Online Shopping Into Accidental Side Hustle: In the prehistoric age before easy online shopping, a bartender discovers a way to supplement the tips she lost during a recession by reselling clothing to her friends.
• Ep. 90 – Academic Advisor Creates Profitable Karaoke League: A Washington, DC man uses new entrepreneurial skills—and vocal chords—to turn a profit and cultivate community.
• Ep. 91 – Copywriter Carves 140 Characters into $50,000 in Cash: A creative director and copywriter makes an April Fool’s joke that turns into a long-term income stream.
• Ep. 92 – WEEKLY RECAP: Karaoke, Tutoring, and Reselling: In our thirteenth weekly recap, we’ll highlight the lessons learned in this week. Also: more listener Q&A!

Ep. 93 (L): Juppy Baby Harness; Ep. 96 (R): Instagram Calligraphy Hustle!

Side Hustle School – Week 14:

• Ep. 93 – Clothing Store Salesman Invents Baby Harness, Earns $100k Per Year: An innovative salesman creates a baby harness that benefits both parent and child, all the while creating a six-figure side income for himself.
• Ep. 94 – Stay-At-Home Mom Helps Immigrants Gain Citizenship with YouTube Tutorials: In Washington, DC, a stay-at-home mom and former teacher helps immigrants gain citizenship with YouTube tutorials.
• Ep. 95 – Craftsman Creates $350,000 Hustle from Handcrafted Leather Products: A leather craftsman starts a successful, multiple six-figure side hustle after being inspired by the tannery he works at for his day job.
• Ep. 96 – Instagram Calligraphy Project Earns $9,000 in Year One: A corporate employee in Texas enters the online world of calligraphy and hand-lettering, then changes along the way to suit her strengths.
• Ep. 97 – Essential Oils Podcast Produces $2,000/Month in Passive Income: A stay-at-home mother starts a podcast about essential oils and pulls her family off government assistance.
• Ep. 98 – Unused Basement Becomes $3,000/Month Pilates Studio: How five minutes of internet research inspired one couple to start an in-home pilates studio in their unfinished basement.
• Ep. 99 – WEEKLY RECAP: Citizenship & Calligraphy: In our fourteenth weekly recap, we’ll highlight the lessons learned in this week. Also: more listener Q&A!

Side Hustle School – Week 15:

• Ep. 100 – Renegade Museum Tour Guide Earns $2 Million: A man in New York City proves that with enough passion and innovation a side hustle can thrive in museums.

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I’ve been happy to see the show finding a good home with the right people. Side Hustle School has published every day since this original milestone. Listen to today’s episode or find an idea to try.