Side Hustle School

Ep. 3485 - STORY: Atlanta Lawyer Walks Into Food Tour Biz 17.07.2026 7min

An Atlanta lawyer creates a thriving and unexpected walking tour 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.comEmail: team@sidehustleschool.comBe on the show: SideHustleSchool.com/questionsConnect on Instagram: @193countriesVisit Chris's main site: ChrisGuillebeau.comRead A Year of Mental Health: yearofmentalhealth.comIf you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼  Hosted on Acast. See acast.com/privacy for more information.

Ep. 3484 - TBT: Multilingual Insurance Agent Creates Translation Course 16.07.2026 7min

In this week’s “Throwback Thursday” segment, we hear from a multilingual insurance agent who creates an online course on the art of translation. 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.comEmail: team@sidehustleschool.comBe on the show: SideHustleSchool.com/questionsConnect on Instagram: @193countriesVisit Chris's main site: ChrisGuillebeau.comRead A Year of Mental Health: yearofmentalhealth.comIf you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼  Hosted on Acast. See acast.com/privacy for more information.

Ep. 3483 - Q&A: Are there any *good* MLM companies? 15.07.2026 4min

Today’s listener is at risk of falling prey to a shady network marketing (MLM) company. How do we know it’s shady? Because it’s a network marketing company! Listen and learn.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.comEmail: team@sidehustleschool.comBe on the show: SideHustleSchool.com/questionsConnect on Instagram: @193countriesVisit Chris's main site: ChrisGuillebeau.comRead A Year of Mental Health: yearofmentalhealth.comIf you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼  Hosted on Acast. See acast.com/privacy for more information.

Ep. 3482 - Q&A: “Recovering after a failed partnership…” 14.07.2026 4min

Today we’re going to hear from a caller who’s previous venture didn’t work out. That one was a partnership with a friend that ended amicably, and now our listener is ready to make another attempt of her own. 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.comEmail: team@sidehustleschool.comBe on the show: SideHustleSchool.com/questionsConnect on Instagram: @193countriesVisit Chris's main site: ChrisGuillebeau.comRead A Year of Mental Health: yearofmentalhealth.comIf you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼  Hosted on Acast. See acast.com/privacy for more information.

Ep. 3481 - First $1,000: Indian Woman Helps Indian Men Improve Dating Profiles 13.07.2026 5min

In this week’s First $1,000 segment, we hear from Priya in Bangalore. She has a side hustle helping men with their dating profiles—and she keeps busy!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.comEmail: team@sidehustleschool.comBe on the show: SideHustleSchool.com/questionsConnect on Instagram: @193countriesVisit Chris's main site: ChrisGuillebeau.comRead A Year of Mental Health: yearofmentalhealth.comIf you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼  Hosted on Acast. See acast.com/privacy for more information.

Ep. 3480 - STORY: Aerospace Apprentice Soars to Seven-Figure Heights 12.07.2026 10min

An eBay experiment started from a childhood bedroom becomes a multi-million, make-your-own-fashion eCommerce empire.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.comEmail: team@sidehustleschool.comBe on the show: SideHustleSchool.com/questionsConnect on Instagram: @193countriesVisit Chris's main site: ChrisGuillebeau.comRead A Year of Mental Health: yearofmentalhealth.comIf you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼  Hosted on Acast. See acast.com/privacy for more information.

Ep. 3479 - Q&A: “Is reselling gift cards a viable idea?” 11.07.2026 4min

Today’s listener is thinking about buying and reselling unused gift cards. It sounds like an interesting idea, but is he missing something obvious? 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.comEmail: team@sidehustleschool.comBe on the show: SideHustleSchool.com/questionsConnect on Instagram: @193countriesVisit Chris's main site: ChrisGuillebeau.comRead A Year of Mental Health: yearofmentalhealth.comIf you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼  Hosted on Acast. See acast.com/privacy for more information.

Ep. 3478 - Failure Friday: “I tried to sell something no one wanted…” 10.07.2026 5min

In this week’s Failure Friday segment, we hear from a seller of gift baskets for college alumni—or at least, that’s what she *tried* to sell. Unfortunately, buyer demand was non-existent. 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.comEmail: team@sidehustleschool.comBe on the show: SideHustleSchool.com/questionsConnect on Instagram: @193countriesVisit Chris's main site: ChrisGuillebeau.comRead A Year of Mental Health: yearofmentalhealth.comIf you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼  Hosted on Acast. See acast.com/privacy for more information.

Ep. 3477 - TBT: “Hero’s Journal” Completes Epic Quest 09.07.2026 8min

In this week’s “Throwback Thursday” segment, we undertake a valiant quest to hear from the co-founder of a legendary journal.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.comEmail: team@sidehustleschool.comBe on the show: SideHustleSchool.com/questionsConnect on Instagram: @193countriesVisit Chris's main site: ChrisGuillebeau.comRead A Year of Mental Health: yearofmentalhealth.comIf you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼  Hosted on Acast. See acast.com/privacy for more information.

Ep. 3476 - Q&A: “How to find markets for livestreaming events?” 08.07.2026 5min

Today’s caller is working on providing livestreaming content creation services for small businesses and events. How can he find a niche or target market to focus 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 year, the show includes free guided lessons and listener Q&A several days each week.Show notes: SideHustleSchool.comEmail: team@sidehustleschool.comBe on the show: SideHustleSchool.com/questionsConnect on Instagram: @193countriesVisit Chris's main site: ChrisGuillebeau.comRead A Year of Mental Health: yearofmentalhealth.comIf you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼  Hosted on Acast. See acast.com/privacy for more information.

Ep. 3475 - Q&A: “How to best use a time of unemployment?” 07.07.2026 6min

Today’s caller faces a big decision: during a time of unemployment, does she stretch her side hustle into a career, or go back to traditional 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.comEmail: team@sidehustleschool.comBe on the show: SideHustleSchool.com/questionsConnect on Instagram: @193countriesVisit Chris's main site: ChrisGuillebeau.comRead A Year of Mental Health: yearofmentalhealth.comIf you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼  Hosted on Acast. See acast.com/privacy for more information.

Ep. 3474 - First $1,000: “I had no idea Hula Hoops were a seasonal business…” 06.07.2026 5min

In this week’s First $1,000 segment, we hear from Holly the Hula Hoop Hustler. She’s now earning up to $2,000/month selling hula hoops on Amazon. But what about her first $1,000—how did she make that happen, and what did she learn? 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.comEmail: team@sidehustleschool.comBe on the show: SideHustleSchool.com/questionsConnect on Instagram: @193countriesVisit Chris's main site: ChrisGuillebeau.comRead A Year of Mental Health: yearofmentalhealth.comIf you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼  Hosted on Acast. See acast.com/privacy for more information.

Ep. 3473 - STORY: Enjoy an Ice Cold Beverage in a Mug Made from Ice 05.07.2026 7min

A visit to the outdoor sauna in the midst of a Minnesota winter inspires a mug made from ice that has sold over 4,000 units. 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.comEmail: team@sidehustleschool.comBe on the show: SideHustleSchool.com/questionsConnect on Instagram: @193countriesVisit Chris's main site: ChrisGuillebeau.comRead A Year of Mental Health: yearofmentalhealth.comIf you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼  Hosted on Acast. See acast.com/privacy for more information.

Ep. 3472 - Q&A: “How should I promote my new app?” 04.07.2026 4min

Today’s caller is wondering about where to go to promote a wellness app she’s made. Is promoting an app different from anything else? 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.comEmail: team@sidehustleschool.comBe on the show: SideHustleSchool.com/questionsConnect on Instagram: @193countriesVisit Chris's main site: ChrisGuillebeau.comRead A Year of Mental Health: yearofmentalhealth.comIf you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼  Hosted on Acast. See acast.com/privacy for more information.

Ep. 3471 - STORY: Tinder Matched Couple Swipes Right to Sell Cupcakes 03.07.2026 8min

After meeting on Tinder, a couple takes a long walk through Central Park and decides to sell cupcakes for $20 each. Surprise: it works. 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.comEmail: team@sidehustleschool.comBe on the show: SideHustleSchool.com/questionsConnect on Instagram: @193countriesVisit Chris's main site: ChrisGuillebeau.comRead A Year of Mental Health: yearofmentalhealth.comIf you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼  Hosted on Acast. See acast.com/privacy for more information.

Ep. 3470 - TBT: Comfy Pillow Provides Seatbelt Support for Cancer Patients 02.07.2026 7min

In this week’s “Throwback Thursday” segment, we hear from the creator of the ParkPuff, a “go anywhere” seat belt pillow for cancer and surgery patients.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.comEmail: team@sidehustleschool.comBe on the show: SideHustleSchool.com/questionsConnect on Instagram: @193countriesVisit Chris's main site: ChrisGuillebeau.comRead A Year of Mental Health: yearofmentalhealth.comIf you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼  Hosted on Acast. See acast.com/privacy for more information.

Ep. 3469 - Q&A: “Where's the best place to hire contractors?” 01.07.2026 5min

Today’s caller is starting a *second* side hustle and wants to know where to find the best virtual assistants and other contractors. 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.comEmail: team@sidehustleschool.comBe on the show: SideHustleSchool.com/questionsConnect on Instagram: @193countriesVisit Chris's main site: ChrisGuillebeau.comRead A Year of Mental Health: yearofmentalhealth.comIf you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼  Hosted on Acast. See acast.com/privacy for more information.

Ep. 3468 - Q&A: “How do you determine a customer’s emotional needs?” 30.06.2026 5min

Today’s listener is inspired to learn more about the “core emotional needs” of a potential customer, but isn’t sure how to do it or what to do with the info. Are these needs always the same, or do they vary? 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.comEmail: team@sidehustleschool.comBe on the show: SideHustleSchool.com/questionsConnect on Instagram: @193countriesVisit Chris's main site: ChrisGuillebeau.comRead A Year of Mental Health: yearofmentalhealth.comIf you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼  Hosted on Acast. See acast.com/privacy for more information.

Ep. 3467 - First $1,000: “Clients don’t want Wordpress, they want a website…” 29.06.2026 4min

In this week’s First $1,000 segment, we hear from the self-described “Wordpress Girl,” who starts a service helping female entrepreneurs get set up with a website.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.comEmail: team@sidehustleschool.comBe on the show: SideHustleSchool.com/questionsConnect on Instagram: @193countriesVisit Chris's main site: ChrisGuillebeau.comRead A Year of Mental Health: yearofmentalhealth.comIf you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼  Hosted on Acast. See acast.com/privacy for more information.

Ep. 3466 - STORY: Music Graduate Makes Spare Change Filling Spare Rooms 28.06.2026 8min

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.comEmail: team@sidehustleschool.comBe on the show: SideHustleSchool.com/questionsConnect on Instagram: @193countriesVisit Chris's main site: ChrisGuillebeau.comRead A Year of Mental Health: yearofmentalhealth.comIf you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼  Hosted on Acast. See acast.com/privacy for more information.