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

3,001 ratings

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LAST EPISODE

#2279 - Q&A: “I’d like to o...

03.29.2023

Today's caller is exploring the intersection of psychology and technology and wants to bring virtual reality (VR) to the world of therapy. Is this possible?? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people ...

Side Hustle School episodes:

03.29.2023 #2279 - Q&A: “I’d like to offer Virtual Reality therapy…” Today's caller is exploring the intersection of psychology and technology and wants to bring virtual reality (VR) to the world of therapy. Is this possible?? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people ...
03.28.2023 #2278 - Q&A: “Tips for handling customer service and support?” You want to make sure you don’t end up in a situation where your limited side hustle time is spent only doing support—instead, you should be spending it on growing your business. But how do you do this, practically speaking? ...
03.27.2023 #2277 - First $1,000: Software Engineer Crafts Balloon Sculptures In this week’s First $1,000 segment, we hear from an engineer who takes out his daytime frustrations on a series of side hustle balloon sculptures. He’s a self-described balloon-atic! Side Hustle School features a new episode EVERY DAY, featuring detailed ...
03.26.2023 #2276 - Q&A: “I want to offer Creative Writing Workshops…” Today’s caller has a passion for creative writing and wants to turn it into a side hustle by offering workshops. How can they go from idea to income? Side Hustle School features a new episode EVERY DAY, featuring detailed case ...
03.25.2023 # 2275 - Q&A: “How can a designer stand out in a crowded market?” The market for web design is getting more crowded every day, and today's caller is looking for advice on how to make her business stand out from the competition. Side Hustle School features a new episode EVERY DAY, featuring detailed ...
03.24.2023 #2274 - Failure Friday: “My first client was a total nightmare…” In this week’s Failure Friday segment, we hear from a woman who had a goal of becoming a personal shopper, but was stymied by a difficult client. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies ...
03.23.2023 #2273 - TBT: Destination Wedding Officiant Travels Worldwide In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a destination wedding officiant who helps couples say their vows in faraway locales. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies ...
03.22.2023 #2272 - Q&A: “How can customer feedback improve my marketing?” Gathering feedback from customers is an important tool for any small business owner, but it can be challenging to know how to use it effectively. Today, a caller seeks advice on how to incorporate feedback into a marketing plan. Side ...
03.21.2023 #2271 - Q&A: “How can I become a sustainability consultant?” With a background in environmental science and a passion for sustainability, today’s caller from Seattle is ready to launch a Sustainability Consultancy. But how can she reach her target audience and make her business a success? Side Hustle School features ...
03.20.2023 #2270 - First $1,000: Health & Wellness Writer Establishes Side Income In this week’s First $1,000 segment, we hear from a freelance writer who works in the health and wellness field. She now earns several thousand dollars a month part-time. Side Hustle School features a new episode EVERY DAY, featuring detailed ...
03.19.2023 #2269 - Q&A: “What are the most effective ways to promote my side hustle?” Sarah has a unique skill set—she’s a reiki practitioner—and is eager to put it to work in a side hustle. But how do you get the word out there in today's digital age? Side Hustle School features a new episode ...
03.18.2023 #2268 - Q&A: “How do I handle the transition from side hustle to full-time business?” Today’s caller is ready to go from side hustle to full-time business! It’s always exciting when this happens, but it also produces questions and concerns. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people ...
03.17.2023 #2267 - Failure Friday: The “American Ninja Warrior” Personal Trainer In this week’s Failure Friday segment, we hear from a personal trainer who wanted to specialize to succeed in a crowded field. The problem was, the specialization he chose may have been too specialized, or perhaps too intimidating. Side Hustle ...
03.16.2023 #2266 - TBT: Successful Screenwriter Becomes Screenplay Consultant In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a freelance screenplay editor in Hollywood. In his new sideline, he consults on scripts from other aspiring screenplay wordsmiths. Side Hustle School features a new episode ...
03.15.2023 #2265 - Q&A: “Planning for a Haunted House in Dallas…” Today's caller has a spooky idea. She wants to create a haunted house attraction, but she needs some guidance in bringing it to life. Don’t be scared! Let’s help her out. Side Hustle School features a new episode EVERY DAY, ...
03.14.2023 #2264 - Q&A: “Indoor Vertical Farming has a lot of potential…” Today we’ll hear from a listener who’s passionate about sustainable agriculture and believes that indoor vertical farming is the way of the future, especially for those living in big cities. How can she turn this into a business? Side Hustle ...
03.13.2023 #2263 - First $1,000: Michigan Accountant Moonlights as Engagement Photographer In this week’s First $1,000 segment, we hear from Elaine in Wayne County, Michigan. She’s an accountant for her day job and works as an engagement photographer for her side hustle. Side Hustle School features a new episode EVERY DAY, ...
03.12.2023 #2262 - Q&A: “My dream is to own a Mobile Adventure Park…” Today's caller is taking a leap of faith with a new and unique idea for a mobile adventure park. How can she make her vision a reality on a low budget? Side Hustle School features a new episode EVERY DAY, ...
03.11.2023 #2261 - Q&A: “How do I choose a legal structure for my side hustle?” A new web developer wants to make sure they set up their business in a way that is efficient and effective, but they're not sure where to start. Let's see if we can help them find a solution. Side Hustle ...
03.10.2023 #2260 - Failure Friday: The Influencer Who Quit Instagram In this week’s Failure Friday segment, we hear from an aspiring influencer on her unsuccessful attempt to become a professional Instagrammer … which ended with her quitting the platform altogether. Side Hustle School features a new episode EVERY DAY, featuring ...
03.09.2023 #2259 - TBT: “Car Parts Guy” Becomes Professional Reseller In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a Chicago car parts reseller. After his first couple of years scouring junkyards for deals, he now sources most of his goods online. Side Hustle School ...
03.08.2023 #2258 - Q&A: “Should I go into business with my best friend?” This caller’s best friend is gung-ho on starting a business with her, but the caller has concerns. How can she determine if this is the right decision for both of them? Side Hustle School features a new episode EVERY DAY, ...
03.07.2023 #2257 - Q&A: “An EV car rental side hustle??” Sarah from Los Angeles is on the line today, and she's got a big idea brewing. Specifically, she’s thinking about starting a car rental business, but with a twist. Is there room in the market for a small, sustainable rental ...
03.06.2023 #2256 - First $1,000: Spotify Musician Gets Paid for Yoga Streams In this week’s First $1,000 segment, we hear from an independent musician who earns passive income from Spotify, focusing on keywords and playlists related to yoga. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of ...
03.05.2023 #2255 - Q&A: “A home-based meal delivery service for New York…” Today’s caller has set his sights on starting a home-based meal delivery service, but wants to make sure he's covering all his bases. Let’s get him on the road to many five-star reviews! Side Hustle School features a new episode ...
03.04.2023 #2254 - Q&A: “I’m starting an Edible Insect Farm…” You read that right. This idea might seem buggy, but there could be a real market for it. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their ...
03.03.2023 #2253 - Failure Friday: ‘Helicopter Parent’ Disrupts Online Tutoring Session In this week’s Failure Friday segment, we hear from a self-described “former online tutor.” His business started well, but was soon challenged by a difficult parent. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of ...
03.02.2023 #2252 - TBT: Children’s Party Hostess Makes Magic and Money In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder of Little Princess Parties, a children’s party hosting business. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people ...
03.01.2023 #2251 - Q&A: “Mobile photo booths for events and parties…” Today’s caller is interested in starting a mobile photo booth business, but wants to make sure she has a solid plan in place. Let's help Janet turn her dream into a thriving business! Side Hustle School features a new episode ...
02.28.2023 #2250 - Q&A: “Can you pay taxes on a credit card to earn cash back?” Tax season is coming up for many of us in the U.S., so today a caller wants to know about paying taxes on a credit card that offers cash back. Is this an all-new side hustle?? Side Hustle School features ...
02.27.2023 #2249 - First $1,000: Bali Nomad Writes Copy for Local Businesses \In this week’s First $1,000 segment, we hear from an Australian expat who moves to Bali to become a digital nomad. This is the story of his first $1,000 as a freelance copywriter. Side Hustle School features a new episode ...
02.26.2023 #2248 - Q&A: “Managing inventory for digital items…” If you’re selling a digital product, isn’t your inventory unlimited? This might sound like a trick question, but there’s more to it. When you continue to add more and more digital products to their online store, there might be a ...
02.25.2023 #2247 - Q&A: “How to become a Medical Billing Advocate?” A caller is wondering about becoming a Medical Billing Advocate. This is someone who helps patients negotiate and lower their medical bills, especially in cases where the bill is high and might include mistakes or unnecessary charges. Side Hustle School ...
02.24.2023 #2246 - Failure Friday: “My business was like a coupon, it expired too soon…” In this week’s Failure Friday segment, we hear from someone who started a coupon directory website. Unfortunately, he ended up spending more money than he saved. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of ...
02.23.2023 #2245 - TBT: “I've been keeping bees for the past five years…” In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a Bay Area beekeeper who slings honey to the tune of $40,000/year part-time. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies ...
02.22.2023 #2244 - Q&A: “I want to become a vintage shopping concierge…” I love hearing side hustle ideas from listeners! Today’s features a woman with a background in retail who wants to become a vintage shopping concierge. Is this idea feasible, profitable, and timely? Side Hustle School features a new episode EVERY ...
02.21.2023 #2243 - Q&A: “Can you set up a Shopify store in just an hour?” Today’s listener poses a challenge: is it possible to set up a Shopify store in just an hour? The platform provides a lot of different features and options, which is great but can be time-consuming to sort through. Side Hustle ...
02.20.2023 #2242 - First $1,000: This Candle Maker Doesn’t Flame Out In this week’s First $1,000 segment, we hear from a longtime candle lover who starts her own brand. After a few months, she reaches a flaming milestone and is lit with excitement. Side Hustle School features a new episode EVERY ...
02.19.2023 #2241 - Q&A: “Email list hosting gets more and more expensive…” Today’s listener has achieved a milestone: they have 3,000 people on their list! That’s great, but because email list providers charge based on subscriber numbers, the monthly subscription cost keeps going up as well. Can anything be done about this? ...
02.18.2023 #2240 - Q&A: “Betting on political markets using Kalshi…” Platforms like Kalshi and Polymarket offer the ability to bet on political events, including presidential elections and cabinet appointments. What are some tips for coming out ahead? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies ...
02.17.2023 #2239 - Failure Friday: “I wasn't making enough money to cover expenses…” In this week’s Failure Friday segment, we hear from a travel agent who’s excited to take flight—until a trip she books for ten clients is unexpectedly canceled. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies ...
02.16.2023 #2238 - TBT: ”I get to make dad jokes about adult toys all day…” In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a seller of adult toys and other items for sexual wellness. She now earns $3,500/month in affiliate commissions! Side Hustle School features a new episode EVERY ...
02.15.2023 #2237 - Q&A: "Retro Resale" store sells floppy disks and cassette tapes A listener wants to open an online store selling floppy disks and cassette tapes. He thinks there’s a renaissance for these items. Is he right—and if so, what steps should he take? Side Hustle School features a new episode EVERY ...
02.14.2023 #2236 - Q&A: “What products are good to sell as a subscription?” Recently we’ve looked at why there are so many subscriptions. Today’s caller wonders: what are some good physical products (i.e. non-digital) to sell in subscription form? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of ...
02.13.2023 #2235 - First $1,000: “I built an Airbnb rental in my backyard…” In this week’s First $1,000 segment, we hear from a serial side hustler who builds an ADU in his backyard, allowing him to earn $1,500/month in passive rentals. He then uses the profits to buy another property. Side Hustle School ...
02.12.2023 #2234 - Q&A: “Help, my website keeps breaking…” All you want to do is run your side hustle, take in orders, maybe grow your business, not just fix things that are broken—but these days, websites often get hacked or just go down for no good reason. Can anything ...
02.11.2023 #2233 - Q&A: “Remote personal training from Pakistan…” Today’s caller is from Pakistan, and he wants to operate a remote personal training side hustle. He’s qualified for this role and thinks it could be helpful—but he’s also wise enough to foresee a couple of challenges. Side Hustle School ...
02.10.2023 #2232 - Failure Friday: Bunny Breeding Gone Bad In this week’s Failure Friday segment, we hear from an aspiring bunny reader. After being inspired by a woman who breeds rabbits to pay for college, she attempts to start her own breeding farm. Unfortunately, it turns out she’s living ...
02.09.2023 #2231 - TBT: Plates and Bowls Using Fulfillment by Amazon In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a pottery maker who sells her dishes and bowls using Fulfillment by Amazon. That service is usually for mass-manufactured items, so her product is a bit ...
02.08.2023 #2230 - Q&A: “Side hustle opportunities for retirees…” In this episode, a caller wonders about opportunities for retirees. Are some side hustles inherently better for someone in that situation? Let’s talk it out! Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people ...

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