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.
Visita il sito del podcast e sostieni chi lo crea: sidehustleschool.com
Autore
Chris Guillebeau
Categoria
Sito del podcast
Ultimo episodio
2 nov 2026
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Episodi
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...
Ep. 2932 - Q&A: “Should I open a second location?” 10.01.2025 4:44
In today's episode, we help a fitness studio owner decide if it's the right time to open a second location. Learn how to evaluate your readiness, minimize risks, and expand without turning success into stress. 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 fre...
Ep. 2931 - TBT: From Gear Rentals to New Zealand Wilderness Adventures 09.01.2025 6:45
In this week's Throwback Thursday segment, we revisit a side hustler who began renting camping gear to tourists in New Zealand. Now, they organize guided wilderness expeditions for beginner adventurers, helping clients from around the world experience the great outdoors. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quit...
Ep. 2930 - Role-Play ing Pastor Rolls The Dice On $2,800/Month Hustle 08.01.2025 6:11
This pastor had been side-hustling his entire adult life and was about to burn out. Luckily a familiar podcast showed him how to save time, sell products, and turn his role playing passion into profit. 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 l...
Ep. 2929 - Q&A: “What can I learn from my website analytics?” 07.01.2025 5:08
In today's episode, we help an online shop owner figure out what to focus on in her website analytics. Learn how to use conversion rates, bounce rates, and other key metrics to grow your e-commerce 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...
Ep. 2928 - First $1,000: Micro-Courses for Fast Learning 06.01.2025 6:10
In this week's First $1,000 segment, we hear from a Minneapolis teacher who turned her knowledge of children's stories into a series of short, actionable online courses. Robin shares how she marketed her micro-courses and earned 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...
2927 - Weekend Workshop: How to Spot a Profitable Side Hustle Idea 05.01.2025 9:41
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: learning to spot profitable 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 y...
Ep. 2926 - Q&A: “Is it wise to offer a money-back guarantee?” 04.01.2025 5:40
In today's episode, we help a photographer decide whether to offer a money-back guarantee for his services. Learn how to build trust with clients while protecting your business from potential downsides. 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...
Ep. 2925 - Q&A: “How can I stand out in the coaching industry?” 03.01.2025 5:55
In today's episode, we help a leadership coach stand out in an oversaturated market. Learn how to identify your unique value, niche down, and attract your ideal clients with strategies that 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 listene...
Ep. 2924 - TBT: Cookie ATM Becomes Pop-Up Hit 02.01.2025 5:55
In this week's Throwback Thursday segment, we revisit two late-night bakers who created Oakland's first cookie ATM. They share how this bold experiment evolved into a thriving pop-up and DIY cookie kit 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 les...
Ep. 2923 - Side Hustle School Season 9 Starts TODAY 01.01.2025 5:46
We're back with an all-new season! Here's how year nine (!) of Side Hustle School will work. Introducing new features, music, and another 365 days of episodes. 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 we...
#2922 - Q&A: “How can I start an ‘adopt don’t shop’ pet business?” 31.12.2024 5:05
In today’s New Year’s Eve episode, we help a listener explore how to turn their passion for the ‘adopt, don’t shop’ movement into a profitable 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 note...
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