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

Business

Podcast website

sidehustleschool.com

Latest episode

Jul 11, 2026

Where to listen?

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Episodes

#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...

#2074 - First $1,000: “You can’t sell anything until you list it…” 05.09.2022

In this week’s First $1,000 segment, we hear from the owner of an Etsy shop called The Blue Breakfront. After making a few rookie mistakes, she leveled-up and began getting steady sales. 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...

#2073 - Q&A: “How can I compete with unfair Etsy sellers?” 04.09.2022

We had an episode recently with an Amazon seller who had a competitor posting lots of fake reviews. Today’s caller has been dealing with a similar issue: unfair Etsy sellers who mass-manufacture their products, contrary to the platform’s seller policy. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. Thi...

#2072 - Q&A: “How to best use a time of unemployment?” 03.09.2022

Today’s caller faces a big decision: during a time of unemployment, does she stretch her side hustle into a career, or go back to traditional 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 listener Q&A several days each week. Show notes: S...

#2071 - Failure Friday: “I thought I’d set up the website incorrectly…” 02.09.2022

In this week’s Failure Friday segment, we hear from a middle-school principal from Pennsylvania. When he starts a blog for high-school volleyball players, it doesn’t get off to a smashing start.    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...

#2070 - TBT: Mochi-Making Classes Transition Online 01.09.2022

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder of KaorisKitchen.com. She started teaching mochi-making classes in the Bay Area, but pivoted to a new business selling mochi donuts locally. 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 inc...

#2069 - Q&A: “Too many coaches! I know I need to ‘choose a niche,’ but how?” 31.08.2022

Today’s listener is a life coach who’s heard me say that the way to succeed with this kind of personal service is to choose a focus or niche. Fair enough … but how do you do that? 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 severa...

#2068 - College Friends Start Utah Fulfillment Center 30.08.2022

Two friends learn the logistics of running a fulfilling business. In their first month of operation, they handled 3,000 orders for a Kickstarter project. 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 not...

#2067 - First $1,000: Lutheran Pastor Sells & Ships “Consecrate” Boxes 29.08.2022

In this week’s First $1,000 segment, we hear from the creator of Consecrate, a subscription box for pastors and ministers. She sends more than 500 boxes out each 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...

#2066 - Q&A: “How do you forecast earnings for a side hustle?” 28.08.2022

A listener came across my back-of-the-napkin spreadsheet template and is wondering something: if a business or side hustle is new, how can you forecast earnings for it? It’s a good question, but there’s also a good answer. 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...

#2065 - Q&A: "They asked for a refund after three hours of coaching..." 27.08.2022

After completing two long sessions with a client, a new coach received a request for a refund. Should she revise her policy of “money back with no questions asked”? 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...

#2064 - Failure Friday: “This is super embarrassing looking back…” 26.08.2022

In this week’s Failure Friday segment, we hear from an Atlanta designer. In addition to her full-time day job, she’s the owner of a stationary brand called Lucky Dog Design. Selling her products on Amazon seemed like a logical idea, but turned into a costly mistake.    Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitti...

#2063 - TBT: Baseball Training School Slides Into Growth 25.08.2022

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder of a baseball training academy. During the pandemic, he opened an additional business selling training gear on Amazon. 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...

#2062 - Q&A: “Can I sell the same thing with two business names?” 24.08.2022

Today’s caller is wondering if she can sell the same line of products with two different brand names. Is this clever or unethical?  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...

#2061 - TV Producer Invents Sustainable Toothpaste Alternative 23.08.2022

After traveling non-stop for a busy job, a TV producer aims to reduce her plastic consumption. 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...

#2060 - First $1,000: “We began with a single sports team…” 22.08.2022

In this week’s First $1,000 segment, we hear from the founder of a sports leadership coaching business. He got his start by volunteering at a local school, and it quickly grew into something more.  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...

#2059 - Q&A: “Amazon Prime Day, but for side hustlers…” 21.08.2022

Today’s listener is wondering about a side hustle version of Prime Day. Can there be such a thing, or should the smaller sellers of the world simply piggyback on what Amazon has done since everyone is shopping anyway? 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...

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