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

#2184 - Q&A: “Can I buy an existing small business?”

What if we could skip the whole startup phase of your side hustle and go straight to burgeoning retailer? None of that whole ideation thing, none of that trial and error—just operating a successful 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@sidehustl...

Dec 24, 2022•5 min•Ep 2184•Transcript available on Metacast

#2183 - Failure Friday: “The sleigh kept getting bogged down…”

In this week’s Failure Friday segment, we hear from a previous caller from the North Pole. Last year he was experiencing a supply chain crisis—this year, he tells a story of his early days. 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 ...

Dec 23, 2022•6 min•Ep 2183•Transcript available on Metacast

#2182 - TBT: “I’m now charging $100/hour for personal training…”

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a personal trainer who goes from clientless to fully booked. He’s raised his rates and has learned a lesson about burnout 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@...

Dec 22, 2022•5 min•Ep 2182•Transcript available on Metacast

#2181 - Q&A: “How to plan for a big New Year's Sale?”

January is a big month for the wellness industry, much more than the end-of-year holidays we’re in the midst of now. How can gym owners, trainers, nutritionists, and other wellness professionals prepare to capitalize on increased interest? 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: SideHustle...

Dec 21, 2022•4 min•Ep 2181•Transcript available on Metacast

#2180 - Q&A: ”My customer tried to barter with me ... after the sale!”

This really happened: after attending a paid workshop, a customer tries to barter by offering her energy healing services in lieu of payment. Uh … how should the event planner handle 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 listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the...

Dec 20, 2022•5 min•Ep 2180•Transcript available on Metacast

#2179 - First $1,000: “I had no idea Hula Hoops were a seasonal business…”

In this week’s First $1,000 segment, we hear from Holly the Hula Hoop Hustler. She’s now earning up to $2,000/month selling hula hoops on Amazon. But what about her first $1,000—how did she make that happen, and what did she 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.c...

Dec 19, 2022•5 min•Ep 2179•Transcript available on Metacast

#2178 - Q&A: “An English-language anime club in Japan…”

Today’s caller wants to start an English-speaking anime club in Japan. With the country recently re-opened for visitors, let’s get this party started! 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/question...

Dec 18, 2022•5 min•Ep 2178•Transcript available on Metacast

#2177 - Q&A: “Are pay-per-click ads cheaper on Pinterest?”

The two largest pay-per-click platforms are Facebook and Google—it’s how they make almost all of their money! But you can also run PPC ads on Reddit, YouTube, streaming platforms like Hulu, and even Pinterest—which is what our caller is wondering about. 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...

Dec 17, 2022•5 min•Ep 2177•Transcript available on Metacast

#2176 - Failure Friday: “No one wanted my idea, even for free…”

In this week’s Failure Friday segment, we hear from a personal trainer who starts a virtual shoe-fitting service. Unfortunately, it stumbles out of the gate and never hits its stride. 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 sh...

Dec 16, 2022•5 min•Ep 2176•Transcript available on Metacast

#2175 - TBT: “I’ve matched my previous salary with 15 hours a week…”

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a Los Angeles film editor who sets out to create a business serving other industry professionals. He now earns as much as his previous salary with just three hours of coaching per day. 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...

Dec 15, 2022•7 min•Ep 2175•Transcript available on Metacast

#2174 - Q&A: “Broker-liaison for overseas web developers…”

A caller has an idea to connect overseas web developers with clients in the U.S. How would this work, and how can they profit 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 listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twi...

Dec 14, 2022•5 min•Ep 2174•Transcript available on Metacast

#2173 - Q&A: “Does anyone make money from cat videos??”

Let’s talk about two of my favorite things in the world: cats and cat videos. A listener wonders if there’s any way to monetize them. How do all those cats get paid?? 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...

Dec 13, 2022•4 min•Ep 2173•Transcript available on Metacast

#2172 - First $1,000: “I help people get back their hacked accounts…”

In this week’s First $1,000 segment, we hear from a coder with an unusual side hustle: he helps clients recover their hacked or lost Facebook accounts. In his first month, he’s already served fifteen people! 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@sidehustl...

Dec 12, 2022•5 min•Ep 2172•Transcript available on Metacast

#2171 - Q&A: “Starting an instructional workshop…”

A caller from Ireland wants to start his own instructional workshop. How are live events different from other services—and what are some tips for running one well? 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...

Dec 11, 2022•5 min•Ep 2171•Transcript available on Metacast

#2170 - Q&A: “How do I focus on retaining clients?”

Today we’re going to hear from a CPA in the midwest who wants to focus on retaining clients. This is more important than finding new ones! 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...

Dec 10, 2022•5 min•Ep 2170•Transcript available on Metacast

#2169 - Failure Friday: “My virtual assistant was a fan of quiet quitting…”

In this week’s Failure Friday segment, we hear from the founder of an advisory service who hires his first assistant. The relationship starts well, but as the founder stops paying attention, things go downhill. Dun dun dun…. 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 Emai...

Dec 09, 2022•6 min•Ep 2169•Transcript available on Metacast

#2168 - TBT: “I built out a Google sheet of people I trusted…”

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder and CEO of a lead generation / digital marketing company called Credo. It’s been through a few different iterations over the years, but continues to grow and evolve. 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...

Dec 08, 2022•6 min•Ep 2168•Transcript available on Metacast

#2167 - Q&A: “I want to be a Door Dash driver for a day…”

Today’s caller wants to drive for Uber Eats, Door Dash, and Postmates—but it’s not what you think. He’s not looking for a new part-time job; he just wants to collect the bonuses that each service offers, then quit. 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@si...

Dec 07, 2022•4 min•Ep 2167•Transcript available on Metacast

#2166 - Q&A: “Can you still make $10,000 with voiceover work on Fiverr?”

In one of the early stories for the podcast that was also included in the Side Hustle book, a guy earned $10,000 in a short amount of time by doing voiceover work commissioned through Fiverr. Is this still possible now? 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: te...

Dec 06, 2022•5 min•Ep 2166•Transcript available on Metacast

#2165 - First $1,000: “Six people signed up, including two at the higher rate…”

In this week’s First $1,000 segment, we hear from a web designer who wants to get off the freelance train by creating a standardized service. Her new “website audit” offer is working! 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 sh...

Dec 05, 2022•6 min•Ep 2165•Transcript available on Metacast

#2164 - Q&A: “How to stand out with an end-of-year sale?”

Today’s caller has a retail business that is not typically dependent on holiday sales, but he wants to juice the numbers a bit. How can you increase end-of-year sales in a non-holiday 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...

Dec 04, 2022•4 min•Ep 2164•Transcript available on Metacast

#2163 - Q&A: “Is making money from surveys still a thing?”

A number of apps, websites, and platforms promise that you can earn a few hundred dollars a month in exchange for your opinion. Is this legit? 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 Connec...

Dec 03, 2022•4 min•Ep 2163•Transcript available on Metacast

#2162 - Failure Friday: “My maple syrup was stolen by a Canadian cartel…”

In this week’s Failure Friday segment, we hear from a maple syrup reseller (this is a thing) whose inventory was stolen by a Canadian cartel (this is not a joke). How does he handle this sticky crisis?? 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@sidehustlescho...

Dec 02, 2022•7 min•Ep 2162•Transcript available on Metacast

#2161 - TBT: “I became the ambassador for a kickbike company…”

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a Florida enthusiast who becomes America’s leading ambassador of kickbikes, a European mode of transport and adventure. 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....

Dec 01, 2022•7 min•Ep 2161•Transcript available on Metacast

#2160 - Q&A: “I want to get paid to lobby for causes I believe in…”

Today’s listener is an aspiring political lobbyist—but this isn’t Job School, it’s Side Hustle School! Can she do part-time lobbying for passive income as a business instead of a career? 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...

Nov 30, 2022•5 min•Ep 2160•Transcript available on Metacast

#2159 - Q&A: “When’s the best time to start a seasonal business?”

If you’re not trying to be Jeff Bezos selling Christmas trees (his original business), you still might want a business that only operates one part of the year. In that situation, when is the best time to start ramping up? 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: ...

Nov 29, 2022•5 min•Ep 2159•Transcript available on Metacast

#2158 - First $1,000: “From TaskRabbit to $4,000/month…”

In this week’s First $1,000 segment, we hear from a handyman who builds his part-time business to $4,000/month on TaskRabbit, and then goes off-app to avoid platform fees. 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: SideHust...

Nov 28, 2022•5 min•Ep 2158•Transcript available on Metacast

#2157 - Q&A: “I’m ready for more passive income…”

Our listener is earning more than $50,000/year from three side projects. Whoo hoo! Still, he wants more of this income to be passive, because he’s doing a lot of work for it. How can he go to the next level? 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@sidehustl...

Nov 27, 2022•5 min•Ep 2157•Transcript available on Metacast

#2156 - Q&A: "Every time I start to make progress, I hold back..."

A listener has a question about self-sabotage: whenever they find themselves moving forward, they end up backing away. What can be done in this situation? 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/ques...

Nov 26, 2022•5 min•Ep 2156•Transcript available on Metacast

#2155 - Failure Friday: “I never should have borrowed money to invest…”

In this week’s Failure Friday segment, we hear from a listener who borrowed money from a friend for an investment in a cryptocurrency project. Need we say 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 Be on the show: SideHustleSchool.co...

Nov 25, 2022•5 min•Ep 2155•Transcript available on Metacast