Side Hustle School

By Chris Guillebeau / Onward Project

Business Careers

What's Side Hustle School about?

A daily show for everyone who works a regular job and wants to start an income-earning project on the side. In each episode, listeners will hear a different story of someone who's started a side hustle—along with what went well, how that person overcame challenges, and what happened as a result. The show is written and hosted by Chris Guillebeau, the New York Times bestselling author of The $100 Startup, The Happiness of Pursuit, and other books.

4.7

2,960 ratings

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LAST EPISODE

#1395 - Q&A: Should I pay a...

10.26.2020

Today’s caller is trying to build her brand as a lifestyle coach. Should she hire a publicist to book her as a guest on podcasts? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people ...

Side Hustle School episodes:

10.26.2020 #1395 - Q&A: Should I pay a publicist to book me as a podcast guest? Today’s caller is trying to build her brand as a lifestyle coach. Should she hire a publicist to book her as a guest on podcasts? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people ...
10.25.2020 #1394 - “Decision Coach” Makes Money By Making Decisions After being asked by her friends and family to give them straightforward advice, a writer decides to see if she can get paid to make decisions for other people. Side Hustle School features a new episode EVERY DAY, featuring detailed ...
10.24.2020 #1393 - Q&A: How can I use my degree with my side hustle? A caller from the U.K. is wondering about how to use his degree in sport and exercise science in marketing a coaching service. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn ...
10.23.2020 #1392 - Q&A: How can I produce in-person experiences when people are afraid? If you’re producing a safety-conscious event, how can you market it in a way that overcomes the fear many people have during the pandemic? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who ...
10.22.2020 #1391 - TBT: Physician Designs Plush Toys to Teach Anatomy In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a doctor who makes plush toys in the shape of human organs to teach kids about the body. Side Hustle School features a new episode EVERY ...
10.21.2020 #1390 - Q&A: Should I accept Bitcoin as a payment method? Today’s listener is wondering about Bitcoin, the world’s best known cryptocurrency—should he accept it as payment for his new app? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without ...
10.20.2020 #1389 - Marketing Guy Isn’t Afraid Of Ghostwriting After a partner in a marketing firm fulfills a lifelong dream of writing his own novel, he begins ghostwriting for others, penning children’s books and even poetry. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies ...
10.19.2020 #1388 - CLASSROOM: Dealing with Customer Complaints “Oh no, I got a complaint!” Every side hustler worries about it, but dealing with complaints doesn’t need to be overwhelming. These three strategies will help you make most customers happy, and to know when to stand your ground. Side ...
10.18.2020 #1387 - Off Road Enthusiast Wanders Into Profit When a mechanical engineer and 4x4 fanatic tries to save money on his Jeep upgrades, he wrangles with local vendors for free parts—and winches himself to a new source of income. Side Hustle School features a new episode EVERY DAY, ...
10.17.2020 #1386 - Q&A: My product is selling on Amazon … but how can I get more attention? A listener from Singapore sells biodegradable party cups with cheerful designs. She’s selling them on Amazon, and wondering how to get noticed by more people. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people ...
10.16.2020 #1385 - Q&A: Are there other types of digital assets? Our story of a woman in New Zealand who sells virtual paint brushes for iPad users was very popular, and a listener is wondering: are there any other “digital assets” that can be made for resale? Side Hustle School features ...
10.15.2020 #1384 - TBT: Florist Offers Nationwide, DIY Wedding Flowers In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a wedding florist in Oklahoma who has a creative idea to offer DIY wedding flowers to brides across the country. Side Hustle School features a new ...
10.14.2020 #1383 - Q&A: How can I monetize a site for fans of Black superheroes? A listener wants to build a fan site showcasing Black superheroes from DC and Marvel comics—how can he make money from it? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra ...
10.13.2020 #1382 - Insurance Manager Finds New Shelves for Old Antiques After selling an unwanted collection of antiques, an insurance manager goes on a hunt for more inventory. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. ...
10.12.2020 #1381 - Q&A: What are your top tips for daily writing? Today’s caller is hoping to improve her writing streak. How can we help her keep writing 1,000 words a day? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without ...
10.11.2020 #1380 - Mother-Daughter Team Starts Squeaky-Clean Soap Shop While staying up late one night, a mom and her daughter decide that they want to start a business together. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without ...
10.10.2020 #1379 - Q&A: Should I provide a guarantee for my real estate photography service? Today’s listener is starting to get paid for real estate photography. Should she offer a money-back guarantee in case a client is unsatisfied? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn ...
10.09.2020 #1378 - Q&A: Any ideas for a military couple? They’ve been in the military for more than a decade, and they’re thinking ahead. What might be a good side hustle for a couple that moves frequently and might be deployed? Side Hustle School features a new episode EVERY DAY, ...
10.08.2020 #1377 - TBT: Mobile Coffee Roasting Blends Work and Family In this week’s “Throwback Thursday / Where are they now?” segment, we revisit a neighborhood coffee lover who follows a whim to a mobile roasting operation. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of ...
10.07.2020 #1376 - Q&A: I set up my email list … now what?? Aside from your website, your email list may be the most important tool in growing any new business. After you get it set up, what comes next? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies ...
10.06.2020 #1375 - College Curriculum Developer Makes Minimalist Jewelry When a professional development specialist can’t find “just the right” piece of jewelry, she makes it herself. Six years later, she’s mined a second income creating minimalist, Boho-chic jewelry. Side Hustle School features a new episode EVERY DAY, featuring detailed ...
10.05.2020 #1374 - CLASSROOM: Transitioning Between Projects How can you transition between projects (or a job and a side hustle) without constantly losing your flow—and how can you start a completely new project without just creating more “stuff” to worry about? Side Hustle School features a new ...
10.04.2020 #1373 - Texas Mom Profits from Poshmark Sales A mom of two young daughters goes to look for used clothes, and ends up finding a new pastime of reselling items on Poshmark and other platforms. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies ...
10.03.2020 #1372 - Q&A: Can I compete with Gazelle by reselling iPhones? When you upgrade your iPhone or Android smartphone, what do you do with the old one? Many of us trade them in, knowing that we aren’t getting a great deal but not wanting to hassle with an alternative. Today’s listener ...
10.02.2020 #1371 - Q&A: How to convert non-paying students into customers? Today’s caller (from Egypt!) is teaching software development through an apprenticeship model, but most of his students aren’t paying. How can he convert some of these free students into customers? Side Hustle School features a new episode EVERY DAY, featuring ...
10.01.2020 #1370 - TBT: The Accountant Who Sold Spreadsheets to Etsy Sellers In this week’s “Throwback Thursday / Where are they now?” segment, we hear from an accountant who sells spreadsheet templates and other financial resources to creatives. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of ...
09.30.2020 #1369 - Q&A: Do I have to sell as a SAAS? A listener is trying to decide how to price a new online service. Should she use the common SAAS (“software as a service”) model, or are there alternatives? Side Hustle School features a new episode EVERY DAY, featuring detailed case ...
09.29.2020 #1368 - Mother Of Five Sells Pretty Old Books When a stay at home mom hopes to avoid returning to full-time work outside the home, she starts selling vintage books packaged by color—and her dream becomes more than a pigment of her imagination. Side Hustle School features a new ...
09.28.2020 #1367 - Q&A: Help! My website images keep disappearing… Today’s listener is having a weird problem—the images on his posts are disappearing. What’s going on? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This ...
09.27.2020 #1366 - Homeschooler Unleashes Creativity with Penmanship Posters While homeschooling her twin daughters, this genetic analyst goes in search of penmanship aids—and ends up making her own. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting ...
09.26.2020 #1365 - Q&A: How can I get more comments on my blog and Instagram posts? Today’s listener wants more engagement from her online community. How can she achieve her objective—and is it the right way to measure success? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn ...
09.25.2020 #1364 - Q&A: Do I really need to open a business bank account? I’ve always said that when you begin to earn income apart from your day job, you need to open a separate bank account … but today’s caller questions that advice. Might there be some exceptions? Side Hustle School features a ...
09.24.2020 #1363 - TBT: Popular Board Game Raises $1 Million on Kickstarter In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a fan of old-school board games who’s achieved tremendous success with multiple crowdfunding projects. Side Hustle School features a new episode EVERY DAY, featuring detailed case ...
09.23.2020 #1362 - Q&A: How to launch a communications business for healthcare providers? Today’s listener is a medical professional by background and is starting a communications business on the side. How can she find her first clients and stand out from larger organizations? Side Hustle School features a new episode EVERY DAY, featuring ...
09.22.2020 #1361 - Texas Teacher Takes On Test-Taking Tutorials When a teacher takes a new certification test in order to keep his job, he blogs about the experience and builds a following by helping others achieve A+ results. Side Hustle School features a new episode EVERY DAY, featuring detailed ...
09.21.2020 #1360 - CLASSROOM: How to Ask for Referrals Your existing customer base is the single best source of referrals—and you don’t have to pay to advertise to them. How can you develop a regular process of encouraging referrals? Side Hustle School features a new episode EVERY DAY, featuring ...
09.20.2020 #1359 - Land Surveyor Paints a Sign Hustle When a land surveyor and father of three can’t take his job any more, he experiments with business ideas until he lands on something that doesn’t feel sketchy. Side Hustle School features a new episode EVERY DAY, featuring detailed case ...
09.19.2020 #1358 - Q&A: Can I use other people's recipes for my ebook for children? Today’s listener has a new YouTube channel and wants to write a related ebook that features recipes for kids. Can she borrow and rename recipes that she finds online? Side Hustle School features a new episode EVERY DAY, featuring detailed ...
09.18.2020 #1357 - Q&A: How can I create a product to help people with applied learning? This listener wants to help people learn more actively. Sounds good, but how does it become a product or service? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without ...
09.17.2020 #1356 - TBT: Teaching the World to Play Saxophone In this week’s “Throwback Thursday / Where are they now?” segment, we hear from an Australian musician who’s created an online community to teach students how to play the saxophone. Side Hustle School features a new episode EVERY DAY, featuring ...
09.16.2020 #1355 - Q&A: How can I start a pandemic dating service? Today’s listener wants to start a pandemic dating service. Will it be short-lived—or a viral sensation? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This ...
09.15.2020 #1354 - Magicians Open Enchanting Online Store Dissatisfied with the slow innovation in the magic community, two magicians create their own online retailer. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This ...
09.14.2020 #1353 - Q&A: How can I market Jujitsu products? A listener in Argentina is starting “Run and Roll,” a clothing brand for fans of jujitsu. How can she reach her ideal audience? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn ...
09.13.2020 #1352 - Social Media Manager Moonlights for Mothers After a traumatic birth experience, a biologist turned social media manager takes on another new responsibility of helping expectant mothers. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without ...
09.12.2020 #1351 - Q&A: When is the right time to sell your business? Today’s listener has a rugby lifestyle brand, and he might be ready to sell! How does he know if the time is right, and what should he do next? Side Hustle School features a new episode EVERY DAY, featuring detailed ...
09.11.2020 #1350 - Q&A: How can I use Spotify as a lead generation source? How can an independent musician connect with fans who discover them on Spotify or Soundcloud? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, ...
09.10.2020 #1349 - TBT: Coronavirus Triples Sales of Cold Brew Coffee In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the co-founder of Bizzy Coffee. They started by selling “coffee shots,” but achieved much more success by changing to cold, 48-ounce bottles. Side Hustle School features ...
09.09.2020 #1348 - Q&A: What should I know before I start a Twitch channel? A listener has a cooking show on YouTube, and she wants to branch out to another platform. Is there a way to do this without working twice as hard—and what does she need to know? Side Hustle School features a ...
09.08.2020 #1347 - Dedicated Runner Goes the Distance for Online Training When a government contractor and experienced runner injures himself after a marathon, he races to start a blog helping others avoid the same fate—ending up on track for his own success. Side Hustle School features a new episode EVERY DAY, ...
09.07.2020 #1346 - CLASSROOM: Selling a Food & Beverage Product Want to sell your gluten-free pizza dough or Paleo-friendly donuts? It’s not as simple as selling an ebook, but it can be done. This episode provides 5 essential tips for the aspiring foodpreneur. Side Hustle School features a new episode ...

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