Side Hustle School - podcast cover

Side Hustle School

Chris Guillebeau sidehustleschool.com
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.

Hosted on Acast. See acast.com/privacy for more information.

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Episodes

#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 School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be o...

Mar 11, 20234 minEp. 2261

#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 detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.co...

Mar 10, 20237 minEp. 2260

#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 features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@side...

Mar 09, 20235 minEp. 2259

#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, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleS...

Mar 08, 20235 minEp. 2258

#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 car brand? 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, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchoo...

Mar 07, 20235 minEp. 2257

#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 people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchoo...

Mar 06, 20235 minEp. 2256

#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 EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the...

Mar 05, 20235 minEp. 2255

#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 job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: ...

Mar 04, 20235 minEp. 2254

#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 people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleScho...

Mar 03, 20235 minEp. 2253

#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 who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/qu...

Mar 02, 20234 minEp. 2252

#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 EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the sh...

Mar 01, 20235 minEp. 2251

#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 a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: Side...

Feb 28, 20235 minEp. 2250

#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 EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show...

Feb 27, 20234 minEp. 2249

#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 downside. 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, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleS...

Feb 26, 20235 minEp. 2248

#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 features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchoo...

Feb 25, 20235 minEp. 2247

#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 people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.c...

Feb 24, 20237 minEp. 2246

#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 of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/qu...

Feb 23, 20235 minEp. 2245

#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 DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.c...

Feb 22, 20235 minEp. 2244

#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 School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@si...

Feb 21, 20235 minEp. 2243

#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 DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: ...

Feb 20, 20235 minEp. 2242

#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? 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, the show includes free guided lessons and listener Q&A several days each week. Show notes:...

Feb 19, 20235 minEp. 2241

#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 of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the sho...

Feb 18, 20236 minEp. 2240

#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 of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.co...

Feb 17, 20236 minEp. 2239

#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 DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be ...

Feb 16, 20235 minEp. 2238

#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 DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show:...

Feb 15, 20235 minEp. 2237

#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 people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHust...

Feb 14, 20235 minEp. 2236

#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 features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehu...

Feb 13, 20235 minEp. 2235

#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 be done? 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, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: ...

Feb 12, 20235 minEp. 2234

#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 features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team...

Feb 11, 20236 minEp. 2233

#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 on burrowed time. 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, the show includes free guided lessons and listener Q&A several days each week. Show note...

Feb 10, 20235 minEp. 2232
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