Side Hustle School

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Episodes

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Side Hustle School

Chris Guillebeau / Onward Project•sidehustleschool.com

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.

Sales and Distribution by Lemonada Media https://lemonadamedia.com/

Episodes

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

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 quitting their job. This year, the show includes free guided lessons and listener Q&A several days each w...

Aug 26, 2022•7 min•Ep 2064•Transcript available on Metacast

#2063 - TBT: Baseball Training School Slides Into Growth

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 lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehu...

Aug 25, 2022•9 min•Ep 2063•Transcript available on Metacast

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

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.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter...

Aug 24, 2022•4 min•Ep 2062•Transcript available on Metacast

#2061 - TV Producer Invents Sustainable Toothpaste Alternative

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 Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instag...

Aug 23, 2022•7 min•Ep 2061•Transcript available on Metacast

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

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 listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com...

Aug 22, 2022•7 min•Ep 2060•Transcript available on Metacast

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

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 guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team...

Aug 21, 2022•5 min•Ep 2059•Transcript available on Metacast

#2058 - Q&A: “How do I transition from Etsy to Shopify?”

A listener has been selling on Etsy and wants to make the switch to Shopify. What’s the best way to do this? 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 Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Con...

Aug 20, 2022•5 min•Ep 2058•Transcript available on Metacast

#2057 - Failure Friday: “Then one afternoon I got a call from the police…”

In this week’s Failure Friday segment, we hear from Dev Chakravarty from the U.K. He had an idea to start a rental car company for electric vehicles. This turned out to be much more difficult than he expected! 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@sidehus...

Aug 19, 2022•7 min•Ep 2057•Transcript available on Metacast

#2056 - TBT: Philly French Toast Bites Take Over

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder of Lokal Artisan Foods, offering delicious french toast bites in Philadelphia and beyond. 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 Be on the show...

Aug 18, 2022•7 min•Ep 2056•Transcript available on Metacast

#2055 - Q&A: "I sold more by raising my prices—is that wrong??”

Today’s listener has a moral dilemma: they made more money by raising their prices! Wait, what’s wrong with that? Listen to their question to find out. 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 Be on the show: SideHustleSchool.com/questio...

Aug 17, 2022•4 min•Ep 2055•Transcript available on Metacast

#2054 - Health-Conscious Coffee Lover Steeps Into Crowded Market

Taking a cue from her Carda-Mom, a sales professional creates steepable coffee flavoring bags containing organic spices instead of artificial syrups. 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 Be on the show: SideHustleSchool.com/questions...

Aug 16, 2022•7 min•Ep 2054•Transcript available on Metacast

#2053 - First $1,000: “It came from patience and vision boarding…”

In this week’s First $1,000 segment, we hear from a wedding marketer who makes a vision board and sets out to build a new 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitte...

Aug 15, 2022•5 min•Ep 2053•Transcript available on Metacast

#2052 - Q&A: “How to market audio services to Christian filmmakers?”

Today’s caller seeks help marketing his services to a subset of faith-based filmmakers. Where can he find clients, and what does he offer them? 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 Be on the show: SideHustleSchool.com/questions Conne...

Aug 14, 2022•4 min•Ep 2052•Transcript available on Metacast

#2051 - Q&A: “How do creators get paid?”

There are lots of ways an online creator can get paid. Which are the most common—and which are the most profitable? 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 Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguilleb...

Aug 13, 2022•5 min•Ep 2051•Transcript available on Metacast

#2050 - Failure Friday: “Kickstarter rejected my project right before launch…”

In this week’s Failure Friday segment, we hear from the founder of Bad Day Box, offering “snail mail self-care.” She planned to launch on Kickstarter, but was forced to make a last-minute change. 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 ...

Aug 12, 2022•9 min•Ep 2050•Transcript available on Metacast

#2049 - TBT: Lightshows Are the Next Big eSport

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder of Throwlights, a business that sells gear and training for lightshows. The concept comes from electronic music festivals and is taking off worldwide. 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...

Aug 11, 2022•6 min•Ep 2049•Transcript available on Metacast

#2048 - Q&A: “What are the best niches for affiliate programs?”

Today’s caller is planning to jump into the world of affiliate promotion, where you can get paid for recommending products on a website. Are some niches or topics more profitable than others? 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 Be o...

Aug 10, 2022•5 min•Ep 2048•Transcript available on Metacast

#2047 - Busy Mom Cleans Up Debt by Cleaning Car Seats

A part-time occupational therapist and mom of two in search of a new income stream finds the solution with a gig economy platform focused on cleaning baby equipment. 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 Be on the show: SideHustleScho...

Aug 09, 2022•8 min•Ep 2047•Transcript available on Metacast

#2046 - First $1,000: “The pre-launch strategy produced $1,000 on day one…”

In this week’s First $1,000 segment, we hear from the founder of Brave Count, a subscription box for military spouses. 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 Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguil...

Aug 08, 2022•7 min•Ep 2046•Transcript available on Metacast

#2045 - Q&A: “Can I have a career of side hustles?”

Our caller is thinking of going all-in on the world of multiple small businesses—not just one, but a whole career of side hustles. How will it 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions ...

Aug 07, 2022•4 min•Ep 2045•Transcript available on Metacast

#2044 - Q&A: “Help! The topic I chose is no longer relevant”

What if you set out to become an expert in a topic—and all of a sudden, or perhaps over time—that topic becomes less and less relevant? That’s what our listener is facing in today’s episode. 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 Be on...

Aug 06, 2022•6 min•Ep 2044•Transcript available on Metacast

#2043 - Failure Friday: “After I was hit by a car, things got worse…”

In this week’s Failure Friday segment, we hear from an affiliate marketer who encountered an unusual problem: after he was hit by a car, the public knowledge of his business was used against him. 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 ...

Aug 05, 2022•7 min•Ep 2043•Transcript available on Metacast

#2042 - TBT: Filipino Virtual Assistant Hub Serves Millions

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder of OnlineJobs.ph, a directory of Filipino workers available for remote work. The site now has more than two million profiles! 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...

Aug 04, 2022•7 min•Ep 2042•Transcript available on Metacast

#2041 - Q&A: “If you had to start over, how would you grow a blog?”

Blogging can still be profitable and rewarding, but a lot of strategies and tactics have changed over the years. If you’re starting a new blog today, what should you do? 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 Be on the show: SideHustle...

Aug 03, 2022•4 min•Ep 2041•Transcript available on Metacast

#2040 - Shine Bright Like a Diamond (and Sell Them)

The manager of an antique jewelry company takes her skills to the open market, eventually establishing a gem of a 7-figure 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitt...

Aug 02, 2022•7 min•Ep 2040•Transcript available on Metacast

#2039 - First $1,000: “I posted videos on TikTok and started getting paid…”

In this week’s First $1,000 segment, we hear from viral TikTok sensation Rebecca Rogers, a social studies teacher with millions of followers. She now charges $6,000 for a single video post! 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 Be on ...

Aug 01, 2022•9 min•Ep 2039•Transcript available on Metacast

#2038 - Q&A: “How many income streams is best?”

Today’s caller is diving into the world of side hustling, already earning money from one or two sources with plans to add more. Is there an optimal number to aim for? 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 Be on the show: SideHustleSch...

Jul 31, 2022•4 min•Ep 2038•Transcript available on Metacast

#2037 - Q&A: Are there any good MLM companies?

Today’s listener is at risk of falling prey to a shady network marketing (MLM) company. How do we know it’s shady? Because it’s a network marketing company! Listen and learn. 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 Be on the show: SideH...

Jul 30, 2022•5 min•Ep 2037•Transcript available on Metacast

#2036 - Failure Friday: “Despite my best efforts, no one was buying…”

In this week’s Failure Friday segment, we hear from the creator of a writing program. She wanted to reach more people, so she decided to give Facebook her money. What could go wrong? 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 Be on the sho...

Jul 29, 2022•7 min•Ep 2036•Transcript available on Metacast

#2035 - TBT: The Intersection of Customization and Convenience

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the co-founder of Happy Box, a service that offers unique care packages for all occasions. 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 Be on the show: SideHustl...

Jul 28, 2022•7 min•Ep 2035•Transcript available on Metacast