Chris Guillebeau
Side Hustle School
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
Category
Podcast website
Latest episode
Jul 11, 2026
Where to listen?
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Episodes
Ep. 2957 - Q&A: “How can I make a slow month more productive?” 04.02.2025 4:21
In this episode, we explore ways to make quiet months productive, from learning new skills to preparing for a strong comeback. What can you do during a slow season in your 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&...
Ep. 2956 - First $1,000: Temporary Tattoo Artist for Events 03.02.2025 6:45
In this week's First $1,000 segment, we explore how a Mississippi artist turned their love of design into a thriving event business, offering custom temporary tattoos for weddings, parties, and corporate events. 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 les...
Ep. 2955 - Weekend Workshop: Choosing Your Best Idea 02.02.2025 8:19
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: choosing your best 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 s...
Ep. 2954 - Q&A: “Is a subscription box for indie comics the right idea?” 01.02.2025 4:52
In today's episode, we help a comic enthusiast decide whether a subscription box is the best way to promote indie creators. Learn about alternative models that are more flexible, cost-effective, and easier to manage. 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 guide...
Ep. 2953 - Q&A: “How can I negotiate better terms with my suppliers?” 31.01.2025 5:17
In today's episode, we help a bakery owner navigate supplier negotiations. Learn how to improve payment terms, reduce costs, and build stronger partnerships with your vendors. 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...
Ep. 2952 - TBT: Microbrewery Tours Expand to Hops and Brewing Classes 30.01.2025 5:34
In this week's Throwback Thursday segment, we explore how a microbrewery tour guide in Chicago turned their passion for craft beer into a hands-on 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...
Ep. 2951 - Lifelong Girl Scout Earns Her Side Hustle Badge 29.01.2025 7:24
Jodi Carlson devoted much of her adult life to Girl Scout troops—and eventually turned it into the side hustle of her dreams. 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.c...
Ep. 2950 - Q&A: “How much time should I spend on social media each week?” 28.01.2025 5:06
In today's episode, we help a handmade pottery business owner decide how much time to spend on social media each week. Learn how to focus on what works, save time, and grow your online presence without burnout. 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 less...
Ep. 2949 - First $1,000: Career Transition Guides Quickly Earn $25,000 27.01.2025 5:40
In this week's First $1,000 segment, we meet a former HR professional who built a side hustle creating career transition guides. She shares how niche guides and live workshops helped her hit $1,000 and scale her business for consistent 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,...
Ep. 2948 - Weekend Workshop: Money Math Made Simple 26.01.2025 7:04
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: making smart (and simple!) projections. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. T...
Ep. 2947 - Q&A: “What’s the best way to offer payment plans?” 25.01.2025 4:34
In today's episode, we help an online course creator set up payment plans that attract customers while minimizing risks. Learn the best strategies to balance accessibility and profitability. 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...
Ep. 2946 - Q&A: “When should I hire a virtual assistant?” 24.01.2025 5:32
In today's episode, we help a side hustler decide if it's time to hire a virtual assistant. Learn how to assess your readiness, find the right help, and delegate tasks effectively without breaking the bank. 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...
Ep. 2945 - TBT: Bringing STEM to Life with Custom Science Kits 23.01.2025 6:42
In this week's Throwback Thursday segment, we hear how a San Jose educator scaled their DIY science kits. Learn how school partnerships and workshops helped them deliver hands-on STEM experiences to hundreds of kids every 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 include...
Ep. 2944 - The $300,000 Bouncy Castle Drop-Shipping Hustle 22.01.2025 6:58
A Texas man puts a bounce in his step by finding a uniquely profitable niche. This bouncy hustle earns multiple six-figures in its first year! 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: SideHus...
Ep. 2943 - Q&A: “Should I create a niche blog or a broader one?” 21.01.2025 4:53
In today's episode, we help a new blogger decide whether to focus on a specific niche or go broad to grow faster. Learn why starting small and specific can give you the best chance for 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...
Ep. 2942 - First $1,000: Turning Central Park Picnics into Profits 20.01.2025 6:43
In this week's First $1,000 segment, we hear from an NYC event planner who started a pop-up picnic service in the city's parks. Learn how she marketed her picnics and reached her first $1,000. 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...
Ep. 2941 - Weekend Workshop: Sizing Up Your Ideas 19.01.2025 6:55
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: sizing up your 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...
Ep. 2940 - Q&A: “Is a 40% commission worth it for my business?” 18.01.2025 5:08
In today's episode, we help a jewelry maker decide whether to keep selling in a local shop that takes a 40% commission. We'll explore the pros and cons, negotiation tips, and how to maintain strong relationships while growing your 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...
Ep. 2939 - Q&A: “How do I calculate the break-even point?” 17.01.2025 5:03
In today's episode, we help a social media manager calculate her break-even point. Learn how to apply this essential business concept to a service-based business and use it to grow more strategically. 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 li...
Ep. 2938 - TBT: Ghost Influencers and the Art of Viral Storytelling 16.01.2025 6:26
In this week's Throwback Thursday segment, we explore the rise of ghost influencers—anonymous personas creating real engagement for brands. Hear how one edgy social media manager turned this idea 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...
Ep. 2937 - Woman on Food Stamps Earns $86,000 Teaching People to Bake Bread 15.01.2025 6:57
In the face of adversity, a woman creates a series of online courses teaching the art of baking sourdough bread. Stop loafing around! If she can do it, you can too. 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 wee...
Ep. 2936 - Q&A: “What’s the downside of getting funded?” 14.01.2025 5:28
In today's episode, we help a catering business owner weigh the risks of taking outside funding to grow her business. Learn about the potential downsides, from financial pressure to loss of control, and how to make the best decision. 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 in...
Ep. 2935 - First $1,000: The High-Profit Second Life of Thrifted Goods 13.01.2025 5:37
In this week's First $1,000 segment, we meet a repair enthusiast who's giving gently used items a second life. He shares how he created a repair and resale business with unique product stories, quickly reaching his first $1,000. 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 include...
Ep. 2934 - Weekend Workshop: Beg, Borrow, or Steal Ideas 12.01.2025 7:23
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: the power of observation. 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...
Ep. 2933 - Q&A: “How do I know if my idea is going to work?” 11.01.2025 5:29
In today's episode, we help a listener validate their idea for a carpooling app for parents. Learn how to test demand, estimate costs, and spot red flags before investing too much time or money. 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...
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