Side Hustle School


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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Recent Reviews
  • Grahamy0317
    So inspirational
    Chris makes me so happy! He’s so smart, very well traveled, honest, genuine and not bad looking either. Chris makes you think about your life and how to improve it one day at a time
  • random00b
    Thank you!
    Mr. Guillebeau, from one Portlander to another, thank you for your dedication to putting this podcast out day in, day out for the past 3 years. I've been listening from day 1 (well, day 16) and it took this long for me to get my act together and find something to start on the side. I know I'm just the latest person to send kudos, but it still so well-deserved. Bravo!!
  • Laura Towle Photography
    Thank you!
    Inspirational! Thanks!!
  • Alex_aguilar
    One of the best podcasts
    Pure inspiration and encouragement to take action. Thanks Chris for your dedication and selflessness!
  • vinomike77
    Inspiration with ACTION is better! Life-Changing Pod!
    Long time listener here with a desire to start a side hustle. I recently moved from a demanding full-time job managing one of the country’s best wine retail operations here in Chicago, to a flexible part-time position serving tables. This move had allowed me to start my first side hustle, a podcast I co-host called That Wine Pod. We are a brand new show that launched December 4th 2019. With the show on a roll, my 2020 goal is to take action on at least two more ideas this year to finally start what I’ve been dreaming to do ever since discovering this show in 2018. Thank you Chris, and the entire team! You’re changing lives! More updates to come! ❤️
  • Rfpaz
    Inspiration daily.
    I love listening to get my daily dose of inspiration and motivation to keep moving forward with my hustle. Thanks Chris!
  • Ruby Flanigan
    Chris is my new super hero!
    I'm retiring and need a side hustle income stream to pay the costs of the travel and dining I would like to enjoy. After listening to many of these episodes, I've been inspired to figure out which personal interest and passion has the potential for profit. Now, I'm ready to go! I'm using the tools that Chris has has recommended and am so excited. Even if this side hustle doesn't swing, I know I'll be getting valuable expereince for the next one. Thanks, Chris, for your inspiration. Your 2020 program is just what I need to guide me toward success.
  • CosmicBreadBox
    Too Much Fill
    Although I totally respect and understand sponsors, advertisements, and Introductions, making nearly half (around 3-4min) of the show information that is ultimately irrelevant to the listener is just not an engaging podcast. If those could be better implemented, this podcast could be great!
  • nmnolan
    Just Okay
    I’m really not a fan of this show, as there are so many podcasts going over the same topic, and doing it better. Half of the 10 minute show is an intro and ads. There are millions of podcast episodes available, I don’t want to spend 4/10 minutes listening to advertising.
  • JN66133
    Daily inspiration
    “Inspiration is good. Inspiration with action is better. “. Is my new daily mantra. Love Love Love this podcast.
  • Jacki'ee
    Great show
    I am really looking forward to all the new things that will be happening with this podcast in 2020!!
  • MleO2014
    Love this show!
    I appreciate how Chris sticks to the short format but delivers a lot of great info in that time. So many great ideas and stories from others has my creative mind in overdrive trying to figure out which thing to try. Probably will be a few tries before I get it right but I’m ok with that. Thanks Chris for an amazing gift every day!
  • Beebster#9
    Best. Podcast. Ever.
    I listen to this podcast every day. Being in college and working toward a business degree, this show gives me motivation to start my own little business and make some money. Get a head start in the world of business. Even if it is a little step. The insights, stories, networking, ideas, etc. that Chris brings to this podcast is wonderful. I wake up every day excited to see what’s next. I hope he never runs out of episodes. Hopefully I’ll make it on one day!
  • Naffie
    I binge this show whenever possible and it’s given me the mindset and courage I need to start my own side hustle. I hope one day to be big enough to be featured on the show! LOVE-LIVE-HUSTLE!!♥️
  • Amy25la
    The best!!
    This is hands down my favorite podcast. I learn something every day and can’t wait to hear the next story. Just wish each episode was longer. Anyone who dreams of starting a business, big or small, must listen. Great host and content❤️❤️❤️
  • JimNWA
    The quality and quantity of helpful content Chris consistently puts out is remarkable….so I am remarking - very positively.
  • daygo trackstar
    Lots of commercials
    This show now has a lot of commercials. The content is great but the number of commercials for such a short show is annoying
  • Marvey Mezzo
    Best inspiration for an entrepreneur
    I love the short, witty daily inspiration! Thank you Chris.
  • moneymarr
    Daily inspiration!
    This show is just long enough to give you inspiration to take action daily. I’ve been listening for years and it doesn’t disappoint.
  • swapp9
    Chris is the Goat!
    The greatest side hustler of all-time! Daily side hustle case studies, ideas & inspiration! His advice is all so good, because he’s been there before! Surely to help you come up with an idea for some freedom in your own life!
  • Plastic Mind
    Inspiring and informative
    I’ve truly been inspired by this podcast to think more seriously about possible side hussles. I especially like how Chris recaps and pulls together the lessons of past episodes. I look forward to listening and learning more.
  • Life-long Listner
    Great Podcast!
    Such good information and Chris’ delivery is just charming. I love the music, the jokes and especially the content. I’ll be a life-long listener!
  • TheReal_Joe_
    Very Good
    Each podcast has useful information for the every day person. You dont need to go back to school or have years of experience to do it. I like how Chris breaks down the info after every podcast. Super helpful, looking to make it to the show soon.
  • ilovetesla
    Tools & inspiration to start a side business
    Great podcast. I listen every day! Real stories of everyday people who found ways to make money from interests and skills they already had. And they had fun doing it! Busts the myth that work has to be “work”.... meaning that if you do something you enjoy, it won’t feel so much like “work” even though you’ll still need to work. I need to now get off my butt and launch my side hustle and get myself a little more “financial independence!” Once I do I hope to be featured on a future SHS podcast! The podcast also highlights how the internet is giving rise to a whole host of new businesses that can literally be run from anywhere so long as you have a high speed internet connection! Anyway I now have a couple of promising side hustle ideas that I need to pursue. Thanks Chris!
  • ISaveBabies
    Short and sweet
    Quick hits with practical advice and sometimes Chris is punny.
  • gina_0509
    Give credit to the people you talk about
    I would like the names and company names of the people who Chris talks about. He should give credit to the people who have worked hard to start a successful side hustle. Their names, websites, company names should be included in the show notes.
  • ivy4life99
    Love SHS!
    I enjoy Side Hustle School and hearing the stories of entrepreneurs doing amazing things. It encourages me every day that I can take that leap and create the life I want. I’m also reading 100 Side Hustles and enjoying all of the motivating profiles of entrepreneurs. The inspiration is real!
  • Alans wife
    Love this podcast!!!
    After hearing Chris on Gretchen Rubins’ Happier podcast- I got curious and listened and soon enough subscribed. What a short and very informative podcast.. thanks Chris! Hope I can find my own side hustle!
  • Private Al
    Too many ads and too short
    I thought I would like this podcast by after listening to over a dozen episodes I had enough of the ads and sponsorships. Very short episodes and not too much useful information.
  • full circle media
    Inspiring podcast for do-ers❗️
    I got recommended this podcast from a friend and I’ve been binging every episode ever since. Love the breakdown Chris gives and the people that are putting in the work to better their lives are inspiring. Keep up the good work Chris and Side Hustle School crew!
  • pam123#
    Concrete Inspiration!
    It’s awesome to listen to hundreds of ideas...but it’s awesomer to go to the website and SEE what they did.. and say to yourself “ohhhh I bet I could do something like that”.. not copy the business, but apply an approach. For me.. it was soloeyewear example. I see how a mission can be directly incorporated.. right on the homepage. A mission doesn’t have to be buried.. it can be up front and center. Much easier for me to get my mojo back! I download a week at a time of podcasts to Evernote. I walk every morning and listen to a week, while asking Seri to “remind me to check out....”. Chris - thank you SOOOO MUCH!
  • LaYvThomas
    Side Hustle School
    My name is Lauren Thomas and I am nine years old. My mother recommended that I listen to this podcast.
  • FlyingAtHeart
    Small Daily Bits
    I feel like I eat these episodes like candy. These are so motivating and lots of great tips.
  • nyvonne722daisy
    Love listening!
  • mountianmilk
    The narrator doesn’t seems excited about the show, like at all. Not much effort goes into these as they are 10 minutes long, 5 of which are ads. From the sound of it, the host does a quick google search about someone he never met, writes down a couple key notes about their business and that’s it. Nothing in depth, no detail.
  • urbanscribe19
    Quick, actionable advice
    I like that while other podcasts tend to ramble, Chris distills each side hustler’s story into a short, digestible episode packed with creative ideas and actionable advice.
  • Madgehart
    Just What I Was Looking For!
    I recently found this podcast after hearing Chris on The Minimalists — love it!! Stories about real people are magic. I’m excited to find my own hustle!
  • Vickie in the archives
    Archives - summer 2019
    I downloaded the entire archive to my phone. I started with #1 and have been listening (thru my headset) to current. It is my summer 2019 fun project. I listen mostly when I am walking dogs, working in the garden, doing projects, etc. Chris does not know it, but I am racing him to current, I hope to be caught up before he reaches post 1,000. I actually am not interested in a SideHustle for myself. I listen because it is fun, there are lots of great gift ideas, the length is perfect, I enjoy Chris’ style. Thumbs up!
  • Tam4him70
    Love this podcast!!
    This podcast is so helpful to me! Lots of inspiration gleaned every time I listen. I dream of being a success story one day. Love Chris and his realness and helpful knowledge! Keep up the great work, Chris!!!!
  • kencarfagno
    Great Commuting Show for the Business Motivated Employee
    I just found this podcast in the business section of iTunes. I really like how short & simple Chris's stories are. You can literally listen to a whole week in 1 or 2 days of commuting to/from work. I also love when Chis says "Build a bridge to where you want to go." If you're an employee that wants to get out, this show will fill your tank with story after story of normal, everyday people who accomplished something great!
  • Laianna F
    This has been the most amazing podcast that I have come across. I am a creative and never knew what I wanted to do when I grew up. I realize now that it’s because I am multi-passionate. My nature is to want to start new projects and do a multitude of creative and interesting things to make money. Hearing all the stories on this podcast has opened up a new world to me; showing me what is possible. I feel constantly inspired about other people’s stories and ideas. Every time I question my natural inclination to make money in this way, I am reassured that this is not something wrong with me but asset and strength that should be used. Thank you so much for creating this podcast. You have no idea how much you help other creatives out there!
  • sastpete
    I have been listening to this show from the beginning and it doesn’t get old! Each episode is inspirational and authentic. I always feel empowered after a few minutes listening.
  • GeorgiaSeven
    Excellent podcast
    Excellent show, full of stories, inspiration and quality resources. Classes available on LinkedIn too. I am going to purchase the book and I am lucky to be in San Francisco and I can go see him live tonight! I am a big fan!
  • Karenfitz
    Chris, you are making the world a better place. Thank you for the daily inspiration 🙏🏻🙏🏻🙏🏻
  • Expat Deanna
    Small bits of inspiration!
    Love the short format! Listen every morning as I get ready for work and Chris inspires me to find my own side hustle!
  • 1/7 Sinister
    Thank you.
    I have listened to this podcast every Saturday for a year. I’ve started my own side hustle and have been successful. Least I could do is leave a review. Thank you Chris! Amazing!
  • The Brinel
    Thank you. I hope to one day be featured on your show.
  • Carly Vair
    Fantastic, down-to-earth advice
    I first heard Chris on Claire Giovino's podcast The Better Questions, and I enjoyed that episode so much I sought out Chris's own work. I have not been disappointed; Side Hustle School is practically everything I want in a podcast. The episodes are bite-sized and focused, and Chris's advice is practical and helpful -- it was so refreshing not to be told to jump off a cliff and quit my job! Plus, the stories themselves are truly inspiring; I love hearing about how people made money with things they cared about rather than starting a blog in one of three overcrowded niches. Thank you, Chris!
  • Gwyne and Molly
    Listen to you everyday
    I make and sell jewelry. Help what new idea to help my business grow. Thank you for making this podcast.
  • MrandMrsBender
    Great short podcast
    Chris shares the side hustle stories of others providing inspiration and tips. At first, it seemed odd that he didn’t have people on as guests. But now I see the benefit as it keeps the episodes short and to the point. I also love the shout outs to his cat!
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