Chris Guillebeau

Side Hustle School

Business EN ↓ 3536 episodes

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.

Author

Chris Guillebeau

Episodes

#2557 - Welcome to Season 8! (Also: introducing a new project) 01.01.2024 7:14

We’re back with an all-new season! Here’s how year eight (!) of Side Hustle School will work. Also: my new newsletter debuts today. Subscribe and join the community at YearofMentalHealth.com. 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&...

#2556 - Q&A: “I got a book deal! But it’s very small…” 31.12.2023 6:27

Is a small book advance a stepping stone or a stumbling block? This literary listener faces the crossroads of publishing paths. Tune in as we explore what might be best for her 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 d...

#2555 - Q&A: “Inflation is killing my hustle!” 30.12.2023 4:54

Struggling with the pinch of inflation on your side hustle income? Maybe it’s time you raised your prices along with everyone else. Tune in for this and 3 other tips to battle inflation! 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...

#2554 - Failure Friday: The Surprising Impact of Pricing Tiers 29.12.2023 7:31

In this week’s Failure Friday segment, we hear how an online course creator's reluctance to implement pricing tiers limited their income. Once she made the change, she experienced dramatic growth in profits. 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...

#2553 - TBT: The Tennessee Bachelorette Party Boom 28.12.2023 6:08

In this week’s “Throwback Thursday / Where are they now?” segment, we revisit a Nashville entrepreneur’s journey in transforming the bachelorette party scene 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 se...

#2552 - Q&A: “Best affiliate strategy for the year ahead?” 27.12.2023 5:23

In the world of affiliate marketing, success lies in a blend of strategy and authenticity. Let’s help this listener build a platform that not only attracts clicks but also fosters trust. 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...

#2551 - Q&A: “Looking ahead to 2024…” 26.12.2023 4:32

Looking ahead to 2024, what are the emerging trends and technologies for side hustlers? I’ll give you three predictions and two specific ideas. 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: SideH...

#2550 - First $1,000: North Pole Travel Blog Covers Entire World 25.12.2023 6:39

In this week’s First $1,000 segment, we hear from a world traveler with a unique perspective: Santa Claus. Discover how he leveraged his annual global journey to create a successful travel blog, navigating the realms of Santa SEO and monetization through Google Ads. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting...

#2549 - Q&A: “Can I get paid for cell phone plan referrals?” 24.12.2023 5:13

Can you hear me now? In today’s episode, a caller from Austin tunes into the podcast with a question about making connections in the cell phone plan market. Let’s talk strategy and signal clarity! 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 liste...

#2548 - Q&A: “How do I sell my own audiobooks?” 23.12.2023 5:19

A listener has outlined several audiobooks that he’ll be recording soon. What’s the best way he can sell 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@sidehu...

#2547 - Failure Friday: Follower Fallout from Buying Instagram Bots 22.12.2023 7:46

In this week’s Failure Friday segment, we hear from a lifestyle blogger in search of growth on Instagram. After she buys a set of fake followers, her engagement from real followers drops. 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&...

#2546 - TBT: Home Art Biz Grows to 40+ Clients 21.12.2023 5:30

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a muralist who begins offering art lessons as a second 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: S...

#2545 - Q&A: “I’m ready to buy and sell cars for profit…” 20.12.2023 5:29

Wondering how to turn your automotive passion into profit? Tune in as we break down the mechanics of flipping cars for cash and help a listener find the fast lane to side hustle success. 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...

#2544 - Q&A: “I’m getting ‘likes’ but no new followers…” 19.12.2023 4:43

Have you noticed something strange with your recent social posts? Tune in to learn how to leverage your current engagement into a growing follower base on social media. 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...

#2543 - First $1,000: Anime Artist Offers Personalized Commissions 18.12.2023 5:14

In this week's First $1,000 segment, a talented artist capitalizes on their love for anime by offering personalized art commissions. Learn how they navigated pricing strategies, portfolio creation, and keeping up with clients. 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...

#2542 - Q&A: “Is SEO just a scam?” 17.12.2023 5:28

It’s important to rank well in search engines—but can you really control such a thing? A listener wonders if the whole SEO industry is effectively a scam. 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 no...

#2541 - Q&A: “How to integrate masculine and feminine energy in my hustle?” 16.12.2023 5:12

Is there room in the business world for non-traditional concepts like masculine and feminine energy, and how might this differentiate a 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: S...

#2540 - Failure Friday: Profitable Affiliate Website Peters Out 15.12.2023 6:53

In this week’s Failure Friday segment, we explore the downfall of a once-lucrative affiliate business. Tune in to uncover how a stubborn mindset led to a financial nosedive—and the crucial pivot that followed. 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 lesso...

#2539 - TBT: Organizational Advisor Moves from B2C to B2B 14.12.2023 4:51

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from an organizational advisor who starts with home consultations, but transitions to serving businesses when she spots high demand. 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...

#2538 - Q&A: “How can I sell my big app idea?” 13.12.2023 5:13

Like the idea of making an app, then selling it for millions? Don’t miss this episode. 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 th...

#2537 - Q&A: “When’s the best time to start??” 12.12.2023 5:04

A caller is wondering about the optimal time to start a side hustle. Does such a thing exist? 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...

#2536 - First $1,000: Vintage Luggage Upcycler Hits Ground Running 11.12.2023 4:41

In this week's First $1,000 segment, an upcycler transforms forgotten vintage luggage into functional art pieces. 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@s...

#2535 - Q&A: “How can I repurpose content from YouTube?” 10.12.2023 5:30

Creating content is time-consuming. How can you repurpose your content to fit multiple platforms without doubling your workload? 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...

#2534 - Q&A: “Should I accept ads from pharmaceutical companies?” 09.12.2023 6:03

Is it ethical for a health-focused podcast to accept sponsorships from online therapy and pharmaceutical companies? 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@s...

#2533 - Failure Friday: Working Remotely from Thailand Is Stressful! 08.12.2023 6:34

In this week’s Failure Friday segment, we hear from a software engineer who takes advantage of his company’s flexible remote work policy to move to Thailand—but struggles in adapting to working in the middle of the night. 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...