Chris Guillebeau

Side Hustle School

Business EN ↓ 3536 episodes

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

Episodes

#2507 - Q&A: “Should I be a Creator or an Influencer … or neither?” 12.11.2023 4:50

Are you a creator, an influencer, or perhaps a bit of both? Today's listener is curious about the difference between these frequently-used terms 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: SideH...

#2506 - Q&A: “Does Peak Marketplace mean we’ve reached a saturation point?” 11.11.2023 4:10

Have we hit 'Peak Marketplace,' a point where the online world is too crowded for new entrepreneurs? This caller brings up an alternative perspective to a point I made in Gonzo Capitalism. 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&am...

#2505 - Failure Friday: “Remote Year” Nomad Experiences Blogger Burnout 10.11.2023 8:27

In this week’s Failure Friday segment, we hear from a digital nomad who sets out to travel for a year—but soon becomes overwhelmed at the idea of building a business on the road. 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...

#2504 - TBT: Las Vegas Concierge Sells Subscriptions & Savings 09.11.2023 6:48

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a Vegas local who helps tourists save on their visits to Sin City. This is a profitable business for her, bringing in up to $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 include...

#2503 - Q&A: “I want to help gamers get fit…” 08.11.2023 4:39

Can you merge the worlds of fitness and gaming into a unique side hustle? Our caller today is a certified trainer looking to tailor workout routines for gamers. Let’s see if we can help him level-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 lis...

#2502 - Q&A: “What’s the deal with #BookTok?” 07.11.2023 4:42

What's the business model behind viral book trends on social media like #bookstagram and #BookTok? This listener wants to understand how creators are monetizing book-related content. 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 sev...

#2501 - First $1,000: The Canadian Wilderness Experience Curator 06.11.2023 5:07

1 In this week’s First $1,000 segment, we hear from an Alberta man who leads hikes and tours to wilderness areas in his province, incorporating indigenous knowledge and local sites. 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 sev...

#2500 - Q&A: “YouTube channel of the Unclaimed Baggage Center…” 05.11.2023 5:55

Tired of the conventional resale game, today's listener is exploring the untapped potential of unclaimed baggage. We break down how his unique blend of unboxing, storytelling, and resale could be an ingenious side 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...

#2499 - Q&A: “Help! Mailchimp rejected my newsletter…” 04.11.2023 5:35

Struggling with an email service provider that kicked you to the curb? This episode dives into alternatives and strategies for keeping your email marketing game strong, even when your primary tool bails on 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 less...

#2498 - Failure Friday: The Handmade Hustle Hassle 03.11.2023 7:43

In this week’s Failure Friday segment, we hear from a handmade jewelry maker who cuts some corners after experiencing an influx of sales. Unfortunately, customers noticed and the efficiency effort backfired. 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...

#2497 - TBT: Speaking Agent for Authors Builds Out Roster 02.11.2023 6:12

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a longtime event planner who transitions to the world of helping authors and experts get paid speaking gigs. 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&amp...

#2496 - Q&A: “How can you make money from prediction markets?” 01.11.2023 5:13

Ever thought of cashing in on your knack for predictions? Today we explore the world of prediction markets like Augur, Kalshi, and PredictIt. 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...

#2495 - Q&A: “How can I future-proof my travel blog?” 31.10.2023 4:10

SEO isn't a "set it and forget it" game, especially with emerging technologies like AI and voice search on the rise. Tune in to this episode to discover how to evolve your SEO strategy to maintain high Google rankings. 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 gui...

#2494 - First $1,000: Tarot and TikTok Become Winning Combo 30.10.2023 5:10

In this week’s First $1,000 segment, we hear from a tarot card reader who was profitable in one month, all thanks to savvy use of TikTok and smart pricing strategies. 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...

#2493 - Q&A: “My sponsored posts have low engagement…” 29.10.2023 3:58

Sponsored posts are often part of a blogger's income—but this British blogger has a problem: the sponsored posts she runs typically have much lower engagement than her organic posts. What can be done? 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 li...

#2492 - Q&A: “Will my online course cannibalize my freelancing biz?” 28.10.2023 4:38

Diversification is key to financial stability, but could it harm your primary income source? In this episode, a listener seeks help balancing freelancing with an online course offering. 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...

#2491 - FF: Gourmet Chef Gets Lost in the Sauce 27.10.2023 6:24

In this week's Failure Friday segment, we meet a Philadelphia chef who rolled out a gourmet food truck, only to find himself a ghost on the city’s vibrant food scene. Discover how he turned the lessons from his culinary calamity into a new roadmap for success. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their...

#2490 - TBT: Ghostwriter Shifts from Happily Ever After to Whodunnit 26.10.2023 5:34

In this week’s 'Throwback Thursday / Where are they now?' segment, we catch up with a ghostwriter who once specialized in romance novels and has since broken into the true crime genre. She shares how market saturation in her original niche led her to diversify and find unexpected success and fulfillment in a whole new genre. Side Hustle School features a new episode EVERY DAY, featuring detailed c...

#2489 - Q&A: “Tax advice for new freelancers…” 25.10.2023 4:32

Tax season can be a nerve-wracking time, especially when juggling a side hustle. Tune in to learn the single most important piece of tax advice that could save you from getting into trouble with the IRS. 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...

#2488 - Q&A: “My sister stole my side hustle!” 24.10.2023 5:01

When family and business mix, things can get complicated quickly. In this episode, a side hustler is experiencing tension after her sister pursues a very similar 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...

#2487 - First $1,000: Comedy Podcast Editor Creates Recurring Income 23.10.2023 6:47

In this week’s First $1,000 segment, we hear from a freelance podcast editor who decided to specialize in comedy shows. From pricing strategies to building efficient systems, hear how he turned his knack for comedic timing into a money-making side hustle. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job....

#2486 - Q&A: “I haven’t sent an invoice in two years…” 22.10.2023 5:42

In today’s episode, a tutor grapples with the absence of a formal invoicing system in his two-year-old math tutoring side hustle. Let’s fix 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 several days each week. Show notes: Side...

#2485 - Q&A: “I feel defeated by the Instagram algorithm…” 21.10.2023 7:32

Struggling with Instagram's fickle algorithm and the emotional toll of low engagement? Tune in for actionable hacks to beat the system and keep your sanity intact. 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...

#2484 - Failure Friday: The Autumn Sweater Stockpile Saga 20.10.2023 6:14

In this week's Failure Friday segment, we hear from a retailer who gambled half her startup capital on a massive inventory of holiday sweaters, only to watch the season—and her profits—melt away. Learn how she navigated the fallout to come back stronger and ready to tackle her next venture. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extr...

#2483 - TBT: Sustainability Consultant Finds Side Hustle at Day Job 19.10.2023 6:14

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a sustainability consultant who discovered her first client from an unexpected source: her 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 sever...