Side Hustle School

In this week’s Failure Friday segment, we bring you the story of "EduAI," an AI-driven tutoring platform whose technological complexity led to its downfall, underscoring the balance between innovation and usability in EdTech.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.substack.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.

In this week’s “Throwback Thursday / Where are they now?” segment, we meet the semi-retired inventor who's now demystifying the patent process for new creators.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.substack.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.

Join us in this episode as we help a listener find the magic number for her subscription box business. Learn how to calculate the number of subscriptions you need to be sustainable!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.substack.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.

In this episode, we discuss strategies for app developers to navigate Apple's 30% in-app purchase fee. Discover how alternative payment methods, subscription models, and cross-platform development can help maximize your app's revenue while staying within Apple's policy framework.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.substack.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.

In this week’s First $1,000 segment, we delve into the story of a college grad who creates a mentorship platform, connecting fraternity and sorority members with alumni for career guidance.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.substack.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.

In this episode, we explore the pros and cons of live versus on-demand online courses, including some specific resources for course creation. Tune in to learn how to perfectly blend your teaching style with your audience's needs for the best learning experience.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.substack.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.

In this episode, we explore the journey from steady growth to rapid expansion for a caller’s cozy home goods subscription service. Discover the secrets of growth hacking and learn how to *triple* your subscriber base with creativity and data-driven decisions.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.substack.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.

In this week’s Failure Friday segment, a venture into organic cosmetics faces unexpected challenges, highlighting the importance of product testing in natural beauty products.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.substack.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.

In this week’s “Throwback Thursday / Where are they now?” segment, we revisit the story of a New England soapmaker who turned a small, artisanal craft 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.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.substack.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.

In today's episode, we guide a listener through the decision between creating an ebook or an online course for expanding their digital presence. Tune in to learn how to match your content with your unique strengths and audience needs.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.substack.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.

In this episode, we tackle the challenge of keeping daily creative projects fresh and engaging. Learn how to reinvigorate your routine with themes, collaborations, and audience interaction—all of which can increase interest and attention.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.substack.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.

In this week’s First $1,000 segment, we hear from a tech-savvy TikTok user, who creates multiple, AI-powered accounts to promote affiliate products. Very impressive!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.substack.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.

In this episode, we delve into the art of attracting sponsors for your podcast and YouTube channel. Discover how to identify potential sponsors, craft a compelling pitch, and build lasting partnerships that align with your brand and engage your audience.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.substack.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.

In this episode, we delve into whether the Profit First model (from our friend Mike Michalowicz) is a viable financial strategy for a freelance graphic designer.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.substack.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.

In this week’s Failure Friday segment, a plan to start a brewery brand dissolves before launch, due to mismatched commitment levels and challenging state alcohol regulations.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.substack.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.

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a voice actor who uses Fiver to build his portfolio before trying his hand at the booming video game industry.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.substack.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.

A listener from Georgia wants to franchise her culinary tours. In this episode, we dive into the essential steps for transforming a local side hustle into a nationwide franchise.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.substack.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.

A caller with a wellness blog wants to get paid two ways: both from advertising AND a membership model. Can she do this without alienating her longtime followers?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.substack.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.

In this week’s First $1,000 segment, we hear from a former real estate agent who now operates an educational platform to advise potential investors. 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.substack.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.

In this episode, discover how to turn your passion into a powerful message for the TED stage. Get the next steps for crafting a compelling talk, applying to TEDx events, and enhancing presentation skills—all crucial for anyone aspiring to share an idea with the world.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.substack.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.