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.

Husk at besøge podcastens hjemmeside og støtte skaberen: sidehustleschool.com

Forfatter

Chris Guillebeau

Kategori

Business

Podcastens hjemmeside

sidehustleschool.com

Seneste episode

4. nov. 2026

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Episoder

#2099 - Failure Friday: “I had tears in my eyes reading the response…” 30.09.2022

In this week’s Failure Friday segment, we hear from a jewelry seller who almost gets taken out of commission by a highly negative review.    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: SideHustl...

#2098 - TBT: “Thirty years a parking lot striper…” 29.09.2022

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a longtime parking lot striper (not stripper!) who’s also written the definitive how-to guide on the 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 listener Q&...

#2097 - Q&A: “I want to take my seminar on the road…” 28.09.2022

A listener has been teaching a local seminar on speed-reading. She now wants to take her show on the road … and quickly! What does she need to do next?  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...

#2096 - Personal Finance Writer Monetizes Medium Posts 27.09.2022

Hoping to pay off his debt, a policy analyst begins writing about personal finance. Before long, he was earning more than $5,000/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 includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleScho...

#2095 - First $1,000: “I left personal training to become a life coach…” 26.09.2022

In this week’s First $1,000 segment, we hear from a personal trainer who makes a big change to become a life coach. Is she able to manifest her way to a full slate of 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 free guided lessons and listener Q&A several d...

#2094 - Q&A: “I lost money on Bitcoin … is that tax-deductible?” 25.09.2022

If you began investing in cryptocurrency at the top of the market, you might be sitting on some pretty significant losses. Today’s caller is wondering if there’s a bright side: can these losses be deducted from your taxes?  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...

#2093 - Q&A: “I’m starting home improvement classes, with a twist…” 24.09.2022

A listener plans to offer a series of online home improvement classes. Is this a good idea—and if so, how can she connect with potential subscribers and paying 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 guided lessons and listener Q&A several days ea...

#2092 - Failure Friday: “I had to issue refunds and cancel 50 orders…” 23.09.2022

In this week’s Failure Friday segment, we hear from a successful Shopify store owner who sells party favors. Everything was going great, until disaster struck in the form of a misplaced change to her order panel.   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...

#2091 - TBT: Online Yoga for People with Chronic Illnesses 22.09.2022

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a Toronto yoga teacher who offers classes to people with chronic illnesses. She also works as a freelance writer and travels 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...

#2090 - Q&A: “How much income should I reinvest in my business?” 21.09.2022

It’s good to reinvest in your business, but not at any cost. Today’s caller wants to know if there’s a rule of thumb he can use in deciding where to put 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 and listener Q&A several days each week....

#2089 - Six-Figure Lawn Business Becomes Sign of the Times 20.09.2022

A school teacher on maternity leave hits the books and finds her dream side hustle, replacing her day job income and then starting a second 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:...

#2088 - First $1,000: “I sell t-shirts for pug lovers on Amazon…” 19.09.2022

In this week’s First $1,000 segment, we hear from an Amazon Merch on Demand seller. She’s sold thousands of t-shirts through the platform, and has a few tips on what works best. Among other things, shirts for dog lovers are a hot item! 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...

#2087 - Q&A: “Is it more important to be knowledgeable or relatable?” 18.09.2022

A listener is trying to grow his Instagram following. Seems easy enough, right? Actually, no—lots of people struggle with this! It’s a crowded, competitive space. What is the crucial characteristic 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 les...

#2086 - Q&A: “Can I get paid to teach people to play video games?” 17.09.2022

Today’s caller is skilled at gaming, but can he make money from it? He also has a caveat: no eSports. He doesn’t want to play games competitively, he wants to take his knowledge and earn from it.   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...

#2085 - Failure Friday: "My boss discovered my side hustle by accident..." 16.09.2022

In this week’s Failure Friday segment, we hear from a company employee who starts a side hustle making websites during the workday. It goes well—until he steps away from his computer for lunch and forgets to change his desktop!    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...

#2084 - TBT: “I finally learned to let go and delegate…” 15.09.2022

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder of FranchiseFilming.com. Since his last feature, he’s increased his team and business 10x!  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...

#2083 - Q&A: “What kinds of guides or reports sell the best?” 14.09.2022

One of the ways you can profit from your knowledge is by compiling that knowledge into a detailed guide, report, or owner’s manual of sorts—then selling that material. Today’s caller has a smart question: what kinds of guides sell the best?  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...

#2082 - Nanotech Scientist Creates Antimicrobial Product 13.09.2022

After creating an antimicrobial coating for facemasks, a scientist applies the product to his own armpits in an attempt to reduce odor from his bike rides to and from the lab. 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...

#2081 - First $1,000: “I got paid to walk dogs while I was on work calls…” 12.09.2022

In this week’s First $1,000 segment, we hear from a Chicago native who starts “Day Job Dogwalking” during the pandemic. While juggling work calls with her employer, she gets paid (and eventually hires someone) to walk dogs in her neighborhood.  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,...

#2080 - Q&A: "I made a bet to start a business in one day…" 11.09.2022

A listener made a bet with a friend that they can start a business and get at least one paying customer in a single day. Let’s take that bet and see if we can help! 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...

#2079 - Q&A: “How does move-to-earn work—is this real?” 10.09.2022

A couple months ago I wrote about my experience with the Web3 app known as StepN, which pioneered the move-to-earn concept. It’s been an interesting journey, and today a listener calls in to request an update. 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...

#2078 - Failure Friday: “It should have been a small mistake…” 09.09.2022

In this week’s Failure Friday segment, we hear from the owner of an organic cosmetics brand. She was diligent with her product launches and had it down to a system–one that she may have trusted a bit too much.    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 le...

#2077 - TBT: “You Don’t Know My Life” Party Game Goes Global 08.09.2022

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the co-creator of a boxed party game for adults called You Don’t Know My Life. During the pandemic, he started another side hustle hosting virtual game nights for big companies.  Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their jo...

#2076 - Q&A: “One-page business plan: what is the essential info?” 07.09.2022

I once published a one-page business plan that a lot of people have used and referred to over the years. Today, our caller wonders: what is essential about this plan? Can you really explain an entire business in a few paragraphs? 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 includ...

#2075 - Roadside Fruit Empire Produces Sweet Success 06.09.2022

A roadside peach stand pays for college tuition, turning into a bigger business along the way. 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 B...

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