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

#2453 - Q&A: “Will people buy my antique map reproductions?”

After finding a “treasure trove of antique maps” left to her by a traveling grandfather, this geographer is thinking of selling the reproductions as part of a subscription. 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: SideHus...

Sep 19, 2023•5 min•Ep 2453•Transcript available on Metacast

#2452 - First $1,000: Mocktail Tours Support Sober-Curious Visitors

In this week’s First $1,000 segment, we hear from a Washington, DC tour guide who specializes in mocktail-making and sober-curious visits. You don’t need to drink (alcohol) to have a good time! 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...

Sep 18, 2023•6 min•Ep 2452•Transcript available on Metacast

#2451 - Q&A: “Can I start a GoFundMe for my business??”

GoFundMe is used for personal fundraisers of all kinds—but could you use it to raise money for your business idea?? 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...

Sep 17, 2023•5 min•Ep 2451•Transcript available on Metacast

#2450 - Q&A: “Can I sell a ‘vintage vinyl’ subscription?”

A caller dreams of sending melodies from the past into homes with a monthly subscription box. 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 Instagr...

Sep 16, 2023•5 min•Ep 2450•Transcript available on Metacast

#2449 - Failure Friday: Chicago Coffee Roaster Grinds to Halt

In this week’s Failure Friday segment, we hear from a Chicago coffee roaster who has to cash in his caffeinated side hustle. Was this a pour-over decision? 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/que...

Sep 15, 2023•6 min•Ep 2449•Transcript available on Metacast

#2448 - TBT: Turning LinkedIn Connections into Fashion Collections

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a freelance clothing designer who hunts down new clients on LinkedIn. Let’s go behind the seams! 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: Sid...

Sep 14, 2023•6 min•Ep 2448•Transcript available on Metacast

#2447 - Q&A: “Selling NFL subscriptions at 50% off…”

You won’t believe the loophole this caller has found—but is it legal or ethical? 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 Instagram: @193count...

Sep 13, 2023•6 min•Ep 2447•Transcript available on Metacast

#2446 - Q&A: “Why will readers care about my food blog?”

If a food blog falls in the forest, does anyone read it? Let’s see if we can help this ambitious baker best position herself for blogging 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 lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Co...

Sep 12, 2023•7 min•Ep 2446•Transcript available on Metacast

#2445 - First $1,000: New Podcaster Sets Up Joint Venture Deals

In this week’s First $1,000 segment, we hear from a new podcaster with a business model of setting up joint venture (JV) deals. How does it work and how much money does he make? (Hint: at least $1,000.) 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...

Sep 11, 2023•6 min•Ep 2445•Transcript available on Metacast

#2444 - Q&A: “Can I get paid $250k as an AI prompt engineer??”

You might have heard about the rise of AI “prompt engineers,” where people are earning high salaries to help Chat-GPT and other tools create code and content. How do you break into the field? 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...

Sep 10, 2023•6 min•Ep 2444•Transcript available on Metacast

#2443 - Q&A: “Should I upload my podcast to YouTube?”

A history-loving listener is starting a podcast. Should he also upload it to YouTube to find a wider 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 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 C...

Sep 09, 2023•5 min•Ep 2443•Transcript available on Metacast

#2442 - Failure Friday: Graveyard Yoga Fails to Entice Living or Dead

Why not blend a love of the macabre with a passion for yoga? Answer: because it’s too spooky to be salesworthy. In this week’s Failure Friday segment, we hear from a yoga instructor who tries to start a “Graveyard Yoga” series. 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 E...

Sep 08, 2023•6 min•Ep 2442•Transcript available on Metacast

#2441 - TBT: Part-Time Wordpress Setup Earns Full-Time Income

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a business coach in Minneapolis who helps female entrepreneurs optimize their websites. This business operates seasonally and earns up to $6,000/month when it’s in motion. 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...

Sep 07, 2023•7 min•Ep 2441•Transcript available on Metacast

#2440 - Q&A: “The viability of a 3D printing business…”

An engineer hopes to profit from 3D printing. What’s his target market and unique selling proposition? 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 o...

Sep 06, 2023•5 min•Ep 2440•Transcript available on Metacast

#2439 - Q&A: “My goal is to translate medical documents…”

A caller from Spain works for an agency as a professional translator. How can she break out and get translation gigs on her own? 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: ...

Sep 05, 2023•4 min•Ep 2439•Transcript available on Metacast

#2438 - First $1,000: Fashion Affiliate Earns $10,000/Month

In this week’s First $1,000 segment, we hear from a fashion lover who uses affiliate campaigns to earn commissions. This new business 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 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 ...

Sep 04, 2023•6 min•Ep 2438•Transcript available on Metacast

#2437 - Q&A: “Going from corporate design to side hustle design…”

In this episode, we hear from a graphic designer and marketing pro with a knack for creating branded merchandise from his corporate position—and now he wants to try his hand at getting his own 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 days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschoo...

Sep 03, 2023•5 min•Ep 2437•Transcript available on Metacast

#2436 - Q&A: “Do you think social ads are worth it?"

Instagram keeps telling this creator to “boost” her posts by paying for advertising. Is this the path to viral fame or a waste of 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 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 T...

Sep 02, 2023•6 min•Ep 2436•Transcript available on Metacast

#2435 - Failure Friday: The Destination Yoga Retreat That Wasn’t

In this week’s Failure Friday segment, we hear from a yoga teacher who dreamed of leading a retreat in Central America. Just one problem: no one signed 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: team@sidehustleschool.com Be on the show: SideHustleSchool.com/que...

Sep 01, 2023•7 min•Ep 2435•Transcript available on Metacast

#2434 - TBT: SAAS Sales Audits Earn $5,000/Month Part-Time

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from an Australian who turned to LinkedIn and started pitching companies on a specific service: auditing their sales and marketing processes. This is going really well, earning over $5,000/month part-time. 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 sever...

Aug 31, 2023•5 min•Ep 2434•Transcript available on Metacast

#2433 - Q&A: “Negotiating a raise using Side Hustle School principles…”

If you’re side hustling while working your day job, can you still ask for a raise? (Answer: yes!) This episode features four tips to get paid more from your employer. 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...

Aug 30, 2023•5 min•Ep 2433•Transcript available on Metacast

#2432 - Q&A: “Planning to open a Virtual Reality arcade…”

Today's caller hopes to combine his passion with the latest technology in Virtual Reality headsets. Are we ready for a “back to the future” VR arcade? 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...

Aug 29, 2023•5 min•Ep 2432•Transcript available on Metacast

#2431 - First $1,000: Virtual Assistant Specializes in Email

In this week’s First $1,000 segment, we hear from a virtual assistant who does one thing only: manage the inboxes of busy startup founders. 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 o...

Aug 28, 2023•6 min•Ep 2431•Transcript available on Metacast

#2430 - Q&A: “I want to be a personal fitness influencer!”

The world of “fitness influencers” is crowded and noisy, but there’s still a path to success for some. Can we help our listener make a credible plan to make money from her athletic expertise? 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 27, 2023•5 min•Ep 2430•Transcript available on Metacast

#2429 - Q&A: “Ready to go from small money to scaling a business…”

We're shifting gears with our next caller. Instead of making a small amount of extra cash, he wants to “go big” and earn real money. Sounds good to me! Let’s explore the best way to make the leap to scaling your hustle. 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...

Aug 26, 2023•7 min•Ep 2429•Transcript available on Metacast

#2428 - Failure Friday: Don’t Forget to Renew Your Domain Names!

In this week’s Failure Friday segment, we hear from a personal finance blogger who failed to renew his domain name. It was then stolen by a company that provides content we don’t talk about on Side Hustle School. Don’t let this happen to you… 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 25, 2023•6 min•Ep 2428•Transcript available on Metacast

BONUS: Gonzo Capitalism Is Now Out!

After two years, my brand-new-book Gonzo Capitalism is now out in the world. You can find it at any bookstore or online retailer. Also! I'm visiting at least 16 cities: chrisguillebeau.com/tour 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...

Aug 24, 2023•2 min•Transcript available on Metacast

#2427 - TBT: Delaware Cinnamon Rolls Keep Rolling Out

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a Delaware baker who sells cinnamon rolls and more. Each month, she bakes up at least $1,500 in profit with little marketing. 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@sidehustles...

Aug 24, 2023•7 min•Ep 2427•Transcript available on Metacast

#2426 - Q&A: “How to offer UX/UI design consulting…”

A British side hustler hopes to harness her new skills in UX/UI to venture into consulting. 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 Instagram...

Aug 23, 2023•5 min•Ep 2426•Transcript available on Metacast

#2425 - Q&A: “Can I resell only Apple products?”

Have you ever wondered if narrowing your focus in the buy-and-sell game could actually be a key to success? In today’s episode, we’ll hear from a reseller who wants to sell ONLY Apple products. 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...

Aug 22, 2023•6 min•Ep 2425•Transcript available on Metacast