Side Hustle School - podcast cover

Side Hustle School

Chris Guillebeau / Onward Projectsidehustleschool.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.

Sales and Distribution by Lemonada Media https://lemonadamedia.com/  

Episodes

#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

#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 different. 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: SideHu...

Feb 09, 20236 minEp. 2231

#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 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/q...

Feb 08, 20236 minEp. 2230

#2229 - Q&A: “How to use ChatGPT and AI in a side hustle…”

A listener is wondering about AI, specifically ChatGPT, an incredible tool that’s been all over the news lately, and how it applies for side hustling. Can you outsource your tasks to these tools? Can you put them to work? Can you make something using AI and sell 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 w...

Feb 07, 20236 minEp. 2229

#2228 - First $1,000: “Budget Bliss Weddings” Cuts the Cake

In this week’s First $1,000 segment, we hear from a wedding planner who specializes in budget ceremonies while still getting paid for her important work. 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/quest...

Feb 06, 20235 minEp. 2228

#2227 - Q&A: “Conflict with my partner over my side hustle…”

Let’s have some real talk today: a side hustling caller is having a problem with her side hustle: her partner doesn’t like 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:...

Feb 05, 20235 minEp. 2227

#2226 - Q&A: “Is it better to have prices end in the number 9?”

One of our callers has noticed that lots of stuff for sale ends in the number 9. Is this some scientifically proven marketing principle, or is it entirely random? You might be surprised by the answer! 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...

Feb 04, 20235 minEp. 2226

#2225 - Failure Friday: “The scavenger hunt turned into a rainstorm…”

In this week’s Failure Friday segment, we hear from the aspirational owner of a scavenger hunt side hustle. On a big day for a major client, everything goes wrong. 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...

Feb 03, 20236 minEp. 2225

#2224 - TBT: Career Advisor Sells Resume Templates

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a career advisor who sells resume (CV) templates and coaching. The business now brings in at least $4,000/month. 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 02, 20235 minEp. 2224

#2223 - Q&A: “Side hustle opportunities for introverts…”

If you don’t like selling, or just talking to people all the time—I’m in that club!—what do you do? 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 I...

Feb 01, 20236 minEp. 2223

#2222 - Q&A: “I want to make and sell a pickleball paddle…”

Did you know that pickleball is the fastest-growing sport in the world? In this episode, a listener from Arizona wonders about making and selling his own paddle. 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...

Jan 31, 20235 minEp. 2222

#2221 - First $1,000: “I get paid to take stock photos for licensing…”

In this week’s First $1,000 segment, we hear from a photographer who learns to take photos for stock image sites, earning a royalty every time one is licensed. Pretty cool! 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: SideHus...

Jan 30, 20236 minEp. 2221

#2220 - Q&A: “Can't find the time to grow my business!”

We often identify a lack of time as the primary obstacle to starting or growing a side hustle. Often, however, there’s a deeper problem behind the time struggle. Where’s the real resistance? 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...

Jan 29, 20236 minEp. 2220

#2219 - Q&A: “A subscription to manage other subscriptions…”

How many paid subscriptions do you have right now? I’m embarrassed to say I don’t know the answer for myself. Today, a caller wants to develop a tool to help people save money on their recurring subscriptions. I love this idea! 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 E...

Jan 28, 20236 minEp. 2219

#2218 - Failure Friday: “I held a sock puppet show while processing transactions…”

In this week’s Failure Friday segment, we hear from a sock seller who eagerly sets up at a trade show, only to realize his credit card processing equipment isn’t working. Oh no! 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: Si...

Jan 27, 20236 minEp. 2218

#2217 - TBT: “I put in long hours and worked hard to deliver quality work…”

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a web developer who goes from corporate to self-employed, hunting down clients on online job boards like Upwork. 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 ...

Jan 26, 20235 minEp. 2217

#2216 - Q&A: "Ebay selling feels less personal now..."

Longtime listeners know that I got my start in the world of entrepreneurship when I was 19 and learned to sell on eBay. Today, a caller wonders: “Has eBay changed? It feels less personal.” 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 t...

Jan 25, 20236 minEp. 2216

#2215 - Q&A: “How to create ‘transformational’ online courses?”

What’s the latest in online education? That’s what one of our listeners who’s also a course creator wants to know. I’ll focus my answer on “transformation,” an increasingly important concept for anyone who wants to offer any type of online course to be aware of. 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....

Jan 24, 20235 minEp. 2215