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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.
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Side Hustle School
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#2341 - Q&A: “There’s no money in personal training…”
6:34
6:34
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Most personal trainers that I’ve talked to agree on one thing: there’s not much money in just the personal training. This is true even when it’s expensive! Today’s caller wants to transition from in-person, individual sessions to online group classes. What’s the best strategy here? Side Hustle School features a new episode EVERY DAY, featuring deta…
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#2340 - First $1,000: Baltimore Photographer Starts Drone Instruction
7:29
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In this week’s First $1,000 segment, we hear from a Baltimore photographer who finds inspiration high in the sky. His new business teaching drone photography is taking off! 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…
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#2339 - Q&A: “How to offer content strategy services…?”
6:13
6:13
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6:13
As a successful freelance copywriter, today’s caller is looking to transition into content strategy. How can he rebrand himself and find clients in this new space? 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 l…
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#2338 - Q&A: “Selling tote bags, but need to raise prices…”
6:18
6:18
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6:18
Does the world need more tote bags? Apparently the answer is… maybe! Let’s hear from a listener selling eco-friendly tote bags at local markets and online. They’re wondering about the right time to raise prices. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their…
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#2337 - Failure Friday: Rent-a-Friend Fails to Launch in Tulsa
7:41
7:41
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7:41
In this week’s Failure Friday segment, we hear from a small-town side hustler who tries to follow a popular business model from Japan. Unfortunately, the idea is lost in translation. 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…
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#2336 - TBT: Social Media Manager Earns $4,000/Month Part-Time
7:15
7:15
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7:15
In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a social media manager who focuses on female fitness coaches and influencers. 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…
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#2335 - Q&A: “I sell pet bandanas. How can I reach pet influencers on Instagram?”
6:59
6:59
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6:59
She sells handmade pet bandanas, and wants to take her business to the next level—but she’s struggling with pet influencers not getting back to her. 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 list…
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#2334 - Q&A: “Going from weddings to corporate photography…”
5:17
5:17
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5:17
A semi-professional photographer has been specializing in wedding photography, and is now looking to expand his services into corporate events and product photography. How can he do this while maintaining his income? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting …
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#2333 - First $1,000: Home Improvement Employee Moonlights as Renovation Aide
7:29
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7:29
In this week’s First $1,000 segment, we hear from someone who works at a home improvement store by day—and moonlights by advising homeowners on renovation projects. 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 …
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#2332 - Q&A: “I’m adding a subscription box for soaps…”
5:47
5:47
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A listener who sells handmade soap is considering adding a subscription box service, where customers receive a curated selection of products 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 includes free guided lessons and…
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#2331 - Q&A: “Cost-effective marketing strategies?”
6:14
6:14
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6:14
Today's caller is on a mission to find cost-effective marketing strategies for their side hustle. How do you get the word out without spending much 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 an…
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#2330 - Failure Friday: Chicken Rental Service Fails to Egg-cite
7:34
7:34
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7:34
In this week’s Failure Friday segment, we hear from a Boise entrepreneur with the goal of bringing chickens to city dwellers. Alas, in the end the business is forced to flee the coop. 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…
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#2329 - TBT: Handywoman Offers DIY Home Repair Workshops
6:58
6:58
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6:58
In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a Washington handywoman who operates a series of DIY Home Repair workshops. 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 a…
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#2328 - Q&A: “Voiceover artist offers voiceover coaching…”
6:12
6:12
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6:12
A voiceover question from a voiceover artist on potential voiceover coaching for voiceover clients. Did you get that? Hint: it’s about voiceover. 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…
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#2327 - Q&A: “Reaching the right audience with digital prints…”
6:38
6:38
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6:38
In today's episode, we have a question from a listener working on a side hustle creating and selling digital art prints online. How can he discover and reach the perfect audience? 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…
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#2326 - First $1,000: Baltimore Photographer Starts Drone Instruction
6:55
6:55
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6:55
In this week’s First $1,000 segment, we hear from a Baltimore photographer who finds inspiration high in the sky. His new business teaching drone photography is taking off! 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…
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#2325 - Q&A: “I'm looking to leverage my existing skills…”
6:39
6:39
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6:39
In today’s episode, a talented graphic designer and marketer searches for a fulfilling side hustle that capitalizes on her existing skill set. How can you find one for yourself? 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…
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#2324 - Q&A: “I want to offer home staging services…”
6:45
6:45
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6:45
A listener in Vancouver wants to start a home staging side hustle. How can she build a portfolio of clients and develop the right relationships? 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…
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#2323 - Failure Friday: “Looking back on my picnic misadventures…”
7:49
7:49
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7:49
In this week’s Failure Friday segment, we hear from a Miami caterer who had a cute idea to sell customized picnic lunches. Unfortunately, things didn’t turn out the way she hoped. 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…
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#2322 - TBT: Mobile Pet Grooming Thrives in Oakland
7:34
7:34
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7:34
In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a startup employee offering a mobile pet grooming side hustle in Oakland, California. 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…
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#2321 - Q&A: “I’m a language tutor… and I need more students!”
7:01
7:01
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7:01
A language tutor in Boston wants to focus more on her sessions and less on bringing in new students. How can she become fully booked? 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…
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#2320 - Q&A: “Handmade pottery sales have plateaued…”
6:32
6:32
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6:32
A listener in Minnesota has been running a side hustle selling handmade pottery on Etsy for about a year. He had a good start with sales but has since plateaued—how can we get him back on the fast track? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. Th…
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#2319 - First $1,000: “I wanted to explore AI-generated art…”
7:40
7:40
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7:40
In this week’s First $1,000 segment, we hear from a real estate professional who makes and sells design elements that come from AI-generated art. 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…
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#2318 - Q&A: “How can I make eco-friendly surfboard wax??”
6:21
6:21
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6:21
We've got a gnarly question today from Brad in San Diego: how can this software developer and surfer start a side business selling eco-friendly surfboard wax? 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 lesson…
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#2317 - Q&A: “Building a network as an introvert…”
5:28
5:28
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5:28
Building a strong network is vital for side hustle success, but today’s caller is an introvert. Should he just “get over it,” or are there strategies he can use to succeed on his own terms? (Hint: door number two.) Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting th…
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