Best Chris Guillebeau Onward Project Podcasts (2025)

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Ep. 3038 - Q&A: “When is it worth spending money on your side hustle?” 5:40

10h ago5:40

5:40

When is it time to start spending real money on your side hustle? In this episode, we explore how to balance scrappiness with strategic investments to fuel growth. 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 l…

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Ep. 3037 - Q&A: “How do I turn being an industry outsider into an advantage?” 4:24

1d ago4:24

4:24

How do you turn being an industry outsider into a strength? In this episode, we explore how to practice creativity while building trust and credibility with customers. 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 guid…

1
Ep. 3036 - TBT: Montana Videographer Redefines Remote Filming 6:26

2d ago6:26

6:26

In this week’s Throwback Thursday segment, discover how a pro videographer ditched travel hassles by mailing filming kits worldwide and directing online course shoots entirely from afar. 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…

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Ep. 3035 - STORY: Frozen Yogurt Dog Treats Are No Barking Matter 6:04

3d ago6:04

6:04

A Colorado couple creates a side hustle that gives dogs and their owners a way to enjoy their frozen treats from their own bowls. 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 da…

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Ep. 3034 - Q&A: “How can I incorporate activism into my brand without seeming performative?” 4:36

4d ago4:36

4:36

How do you build a business that aligns with your values without coming across as performative? In this episode, we help a listener navigate authenticity in sustainability and activism. 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 …

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Ep. 3033 - First $1,000: Feeding the Neighborhood, One Block at a Time 6:10

5d ago6:10

6:10

In this week’s First $1,000 segment, learn how a backyard gardener in Brooklyn joined forces with neighbors to create hyper-local produce boxes, quickly earning $1,000 with minimal overhead. 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 …

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Ep. 3032 - Weekend Workshop: Launch Before You’re Ready 6:36

6d ago6:36

6:36

This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it’s all free. Today’s topic: publishing your offer! Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money wi…

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Ep. 3031 - Q&A: “How do I create and sell a premium online course?” 4:58

7d ago4:58

4:58

In today’s episode, we explore how to create a standout premium online course. Learn how to structure it, position it for a high price point, and stand out in a competitive market. 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 inclu…

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Ep. 3030 - Q&A: “How do I prepare for tech failures without overloading my setup?” 5:36

8d ago5:36

5:36

What happens when a tech glitch disrupts your side hustle? In this episode, we tackle how to prepare for unexpected challenges without overcomplicating your operations. 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 gui…

1
Ep. 3029 - TBT: Travel Blog Becomes Spring Break Powerhouse 6:22

9d ago6:22

6:22

In this week’s Throwback Thursday segment, discover how this side hustler built a spring break site that soars to $8,000 during peak months by combining ad networks with carefully edited AI content. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This ye…

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Ep. 3028 - STORY: College Student Hacks Into $40,000 A Month Side Hustle 7:52

10d ago7:52

7:52

When this student found himself in thousands of dollars worth of debt, he made a simple $40 investment that would go on to transform his life and reach tens of thousands of people around 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 yea…

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Ep. 3027 - Q&A: “How do side hustle ‘power laws’ work?” 5:45

11d ago5:45

5:45

Why do a few things in your business drive most of your results? In this episode, we break down how power laws work and how to focus on what truly moves the needle. 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 …

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Ep. 3026 - First $1,000: From Text Messages to Digital Concierge 5:35

12d ago5:35

5:35

In this week’s First $1,000 segment, discover how one meticulous organizer built an online concierge service, offering tiered subscriptions for routine tasks and real-time support. 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 inclu…

1
Ep. 3025 - Weekend Workshop: Making Time for What Matters 6:38

13d ago6:38

6:38

This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it’s all free. Today’s topic: how to spend 10% more time on your most important tasks. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies…

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Ep. 3024 - Q&A: “What’s the ROI of renting out equipment or tools?” 4:47

14d ago4:47

4:47

In this episode, we explore the ins and outs of running a tool rental business. Learn how to manage inventory, minimize risks, and maximize profits in this potentially lucrative 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 …

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Ep. 3023 - Q&A: “Could selling templates for AI tools be a business?” 4:52

15d ago4:52

4:52

AI tools like ChatGPT are exploding in popularity, but can creating templates for these tools become a profitable side hustle? In this episode, we explore the opportunities, challenges, and potential pitfalls of this idea. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without qui…

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Ep. 3022 - TBT: When Selling Prints Wasn’t Enough 5:50

16d ago5:50

5:50

In this week’s Throwback Thursday feature, discover how pivoting from digital art prints to creating mockups for Etsy and Shopify turned an underperforming side hustle into a high-demand service. 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,…

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Ep. 3021 - STORY: Immigrant Couple Translates Heritage Into Children’s Flash Cards 7:29

17d ago7:29

7:29

Two immigrants from Laos meet the needs of an underserved community, creating a series of dual-language flash cards and other resources. 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 sev…

1
Ep. 3020 - Q&A: “How do I manage last-minute requests without burning out?” 5:26

18d ago5:26

5:26

In this episode, we explore how service-based freelancers can manage last-minute client requests without sacrificing quality or burning out. Learn how to build buffer time into your schedule and set clear project boundaries. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without q…

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Ep. 3019 - First $1,000: Miami Divorce Planner Offers “Freedom Celebrations” 6:37

19d ago6:37

6:37

In this week’s First $1,000 segment, discover how a former wedding planner in Miami pivoted to organizing “freedom celebrations” for newly divorced clients, landing her first thousand dollars from two high-end events. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting…

1
Ep. 3018 - Weekend Workshop: Design Your First Workflow 6:31

20d ago6:31

6:31

This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it’s all free. Today’s topic: creating clear, repeatable systems for running your business efficiently. Side Hustle School features a new episode EVERY DAY, featuring deta…

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Ep. 3017 - Q&A: “How do I balance transparency with professionalism?” 4:34

21d ago4:34

4:34

In this episode, we tackle the tricky balance of being transparent with your audience while maintaining professionalism. How can you build trust without oversharing or compromising your credibility? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This ye…

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Ep. 3016 - Q&A: “Is there still room to start a podcast in 2025?” 4:23

22d ago4:23

4:23

Is it too late to start a podcast in 2025? In this episode, we tackle how to stand out in a crowded field and grow an audience for a niche topic. 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 listene…

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Ep. 3015 - TBT: Bringing Tokyo’s Best Stationery to Global Audiences 6:03

23d ago6:03

6:03

In this week’s Throwback Thursday segment, learn how a stationery-lover in Tokyo began shipping curated paper goods and writing supplies abroad—all while championing small artisan shops. 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…

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Ep. 3014 - STORY: Accountant Earns $233,751 Reselling Items He Buys at Walmart 8:29

24d ago8:29

8:29

A young accountant learns the art of reselling, purchasing textbooks, dental floss, and Cheerios from retail stores in bulk—then earns hundreds of thousands of dollars in profit by selling it 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 y…

Podcasts Worth a Listen

Chris Guillebeau Onward Project Podcasts

Podcasts Worth a Listen

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Side Hustle School

Chris Guillebeau / Onward Project

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Ep. 3038 - Q&A: “When is it worth spending money on your side hustle?” 5:40

1
Ep. 3037 - Q&A: “How do I turn being an industry outsider into an advantage?” 4:24

1
Ep. 3036 - TBT: Montana Videographer Redefines Remote Filming 6:26

1
Ep. 3035 - STORY: Frozen Yogurt Dog Treats Are No Barking Matter 6:04

1
Ep. 3034 - Q&A: “How can I incorporate activism into my brand without seeming performative?” 4:36

1
Ep. 3033 - First $1,000: Feeding the Neighborhood, One Block at a Time 6:10

1
Ep. 3032 - Weekend Workshop: Launch Before You’re Ready 6:36

1
Ep. 3031 - Q&A: “How do I create and sell a premium online course?” 4:58

1
Ep. 3030 - Q&A: “How do I prepare for tech failures without overloading my setup?” 5:36

1
Ep. 3029 - TBT: Travel Blog Becomes Spring Break Powerhouse 6:22

1
Ep. 3028 - STORY: College Student Hacks Into $40,000 A Month Side Hustle 7:52

1
Ep. 3027 - Q&A: “How do side hustle ‘power laws’ work?” 5:45

1
Ep. 3026 - First $1,000: From Text Messages to Digital Concierge 5:35

1
Ep. 3025 - Weekend Workshop: Making Time for What Matters 6:38

1
Ep. 3024 - Q&A: “What’s the ROI of renting out equipment or tools?” 4:47

1
Ep. 3023 - Q&A: “Could selling templates for AI tools be a business?” 4:52

1
Ep. 3022 - TBT: When Selling Prints Wasn’t Enough 5:50

1
Ep. 3021 - STORY: Immigrant Couple Translates Heritage Into Children’s Flash Cards 7:29

1
Ep. 3020 - Q&A: “How do I manage last-minute requests without burning out?” 5:26

1
Ep. 3019 - First $1,000: Miami Divorce Planner Offers “Freedom Celebrations” 6:37

1
Ep. 3018 - Weekend Workshop: Design Your First Workflow 6:31

1
Ep. 3017 - Q&A: “How do I balance transparency with professionalism?” 4:34

1
Ep. 3016 - Q&A: “Is there still room to start a podcast in 2025?” 4:23

1
Ep. 3015 - TBT: Bringing Tokyo’s Best Stationery to Global Audiences 6:03

1
Ep. 3014 - STORY: Accountant Earns $233,751 Reselling Items He Buys at Walmart 8:29