Side Hustle School

Side Hustle School

By Chris Guillebeau
Download on the App Store

Side Hustle School episodes

  • Weekend Workshop: From Rock Bottom to Business Empire
    What It’s About
    How survival instincts turned into a million-dollar business.

    Notes from Chris
    Episode 3270

    It’s Weekend Workshop, and it’s new!

    Listen to today’s episode to learn more…

     

     

    SEE ALSO:

    • Catholic Designer Creates Stylish Apparel Line: What shall it profit a man to gain the whole world but not sell any t-shirts? This designer cast his bread upon the waters and ended up with a profitable fashion line.
    • Seattle Couple Creates New “Income LiveStream”: When a married couple runs into logistical problems at their wedding, it leads to an innovative service that other engaged couples need during the pandemic.
    • Role-Playing Pastor Rolls The Dice On $2800/Month Hustle: Listener success story! This Presbyterian minister turns to his lifelong interest in role-playing games to set up a sustainable second income source.
    • Inspiration is good; inspiration combined with action is better. Now get back to work!

      Yours in the revolution,

      <img class="alignnone wp-image-1825" src="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png" alt="cg-sig-newsletter" width="176" height="82" srcset="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png 300w, https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter.png 450w" sizes="(max-width: 176px) 100vw, 176px">

      Resources
      GET $625 IN FREE TRAVEL

      Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

      I use this card every day all over the world! ✈️

      Learn More

      CREATE YOUR ONLINE STORE

      Create your online store with Shopify using an exclusive discount for Side Hustle School listeners. For a limited time, get a free 21-day trial and a 10% discount for a whole year.

      Many Side Hustle School listeners are building sites using Shopify's easy-to-learn platform. Try it free today!

      Learn More

      Sponsors & Gratitude
      Learn More With Skillshare!

      Supporting the sponsors keeps the show free. Today’s episode of Side Hustle School is brought to you by Skillshare. 📷

      Skillshare is giving Side Hustle School listeners 2 months of unlimited access—for $0.99! Join the 2 million students learning everything from street photography to SEO on Skillshare today!

      Get Started Here!

      Like the Show? Leave a Rating!

      Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference! ✅

      It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.


      Here's How

      Keep in Touch
      <img class="aligncenter wp-image-1272 size-full" src="https://sidehustleschool.com/wp-content/uploads/2017/03/ChrisGuillebeauSideHustleSchoolFull-1.jpg" width="1076" height="251">
      There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

      Follow

      Facebook,Instagram,Twitter

      Email

      Say Hi

      From your favorite airport

      To infinity and beyond,

      Chris Guillebeau
      7 min
    • Q&A: “Should I have a logo before I launch?”
      What It’s About
      When does branding become procrastination?

      Notes from Chris
      Episode 3269

      Early branding is like picking paint colors before breaking ground on a house—harmless fun, but it can also distract from pouring the foundation. There’s nothing wrong with dabbling; Canva mock-ups cost almost nothing. The key is knowing when the creative play stops adding value and starts delaying product validation.

      “I’m drafting ideas for a new specialty tea brand but haven’t finalized a single blend. Instead of finishing the product, I keep tinkering with logos, colors, and typography because it’s fun. Friends tell me this is procrastination—that branding can wait until after validation. Others say a professional look helps attract early wholesale interest. Where’s the line between useful early branding and busywork? What’s the minimum identity I need now, and what should I postpone until I actually have something to sell?”

      Listen to today’s episode to learn more…

       

       

      SEE ALSO:

      • Catholic Designer Creates Stylish Apparel Line: What shall it profit a man to gain the whole world but not sell any t-shirts? This designer cast his bread upon the waters and ended up with a profitable fashion line.
      • Seattle Couple Creates New “Income LiveStream”: When a married couple runs into logistical problems at their wedding, it leads to an innovative service that other engaged couples need during the pandemic.
      • Role-Playing Pastor Rolls The Dice On $2800/Month Hustle: Listener success story! This Presbyterian minister turns to his lifelong interest in role-playing games to set up a sustainable second income source.
      • Inspiration is good; inspiration combined with action is better. Now get back to work!

        Yours in the revolution,

        <img class="alignnone wp-image-1825" src="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png" alt="cg-sig-newsletter" width="176" height="82" srcset="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png 300w, https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter.png 450w" sizes="(max-width: 176px) 100vw, 176px">

        Resources
        GET $625 IN FREE TRAVEL

        Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

        I use this card every day all over the world! ✈️

        Learn More

        CREATE YOUR ONLINE STORE

        Create your online store with Shopify using an exclusive discount for Side Hustle School listeners. For a limited time, get a free 21-day trial and a 10% discount for a whole year.

        Many Side Hustle School listeners are building sites using Shopify's easy-to-learn platform. Try it free today!

        Learn More

        Sponsors & Gratitude
        Learn More With Skillshare!

        Supporting the sponsors keeps the show free. Today’s episode of Side Hustle School is brought to you by Skillshare. 📷

        Skillshare is giving Side Hustle School listeners 2 months of unlimited access—for $0.99! Join the 2 million students learning everything from street photography to SEO on Skillshare today!

        Get Started Here!

        Like the Show? Leave a Rating!

        Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference! ✅

        It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.


        Here's How

        Keep in Touch
        <img class="aligncenter wp-image-1272 size-full" src="https://sidehustleschool.com/wp-content/uploads/2017/03/ChrisGuillebeauSideHustleSchoolFull-1.jpg" width="1076" height="251">
        There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

        Follow

        Facebook,Instagram,Twitter

        Email

        Say Hi

        From your favorite airport

        To infinity and beyond,

        Chris Guillebeau
        8 min
      • Q&A: “Are Instagram links killing my reach?”
        What It’s About
        Is Instagram quietly punishing posts with links?

        Notes from Chris
        Episode 3268

        Instagram wants people to stay on Instagram, so posts that look “leave-y” sometimes underperform—whether or not there’s an official penalty. The solution isn’t to give up on sales; it’s to shift the link from a static caption (which isn’t even clickable) to formats the algorithm already rewards: interaction, DMs, Stories, product tags. Here’s a practical mix.

        “Every time I post a new ceramic mug on Instagram, I add my Linktree in the caption so buyers can click through to my Shopify store. Lately my reach has tanked, and almost no one even sees my posts. Friends say Instagram buries posts with external links. I don’t want to spam ‘DM me to buy,’ but hiding the link kills sales. What’s the smart way to respect these annoying platform quirks yet still move followers to an actual checkout page?”

        Listen to today’s episode to learn more…

         

         

        SEE ALSO:

        • Catholic Designer Creates Stylish Apparel Line: What shall it profit a man to gain the whole world but not sell any t-shirts? This designer cast his bread upon the waters and ended up with a profitable fashion line.
        • Seattle Couple Creates New “Income LiveStream”: When a married couple runs into logistical problems at their wedding, it leads to an innovative service that other engaged couples need during the pandemic.
        • Role-Playing Pastor Rolls The Dice On $2800/Month Hustle: Listener success story! This Presbyterian minister turns to his lifelong interest in role-playing games to set up a sustainable second income source.
        • Inspiration is good; inspiration combined with action is better. Now get back to work!

          Yours in the revolution,

          <img class="alignnone wp-image-1825" src="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png" alt="cg-sig-newsletter" width="176" height="82" srcset="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png 300w, https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter.png 450w" sizes="(max-width: 176px) 100vw, 176px">

          Resources
          GET $625 IN FREE TRAVEL

          Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

          I use this card every day all over the world! ✈️

          Learn More

          CREATE YOUR ONLINE STORE

          Create your online store with Shopify using an exclusive discount for Side Hustle School listeners. For a limited time, get a free 21-day trial and a 10% discount for a whole year.

          Many Side Hustle School listeners are building sites using Shopify's easy-to-learn platform. Try it free today!

          Learn More

          Sponsors & Gratitude
          Learn More With Skillshare!

          Supporting the sponsors keeps the show free. Today’s episode of Side Hustle School is brought to you by Skillshare. 📷

          Skillshare is giving Side Hustle School listeners 2 months of unlimited access—for $0.99! Join the 2 million students learning everything from street photography to SEO on Skillshare today!

          Get Started Here!

          Like the Show? Leave a Rating!

          Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference! ✅

          It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.


          Here's How

          Keep in Touch
          <img class="aligncenter wp-image-1272 size-full" src="https://sidehustleschool.com/wp-content/uploads/2017/03/ChrisGuillebeauSideHustleSchoolFull-1.jpg" width="1076" height="251">
          There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

          Follow

          Facebook,Instagram,Twitter

          Email

          Say Hi

          From your favorite airport

          To infinity and beyond,

          Chris Guillebeau
          8 min
        • TBT: Hand-Written Recipes Become Kitchen Wall Art
          What It’s About
          Hand-written recipe cards turn into framed keepsakes—and a quietly thriving Etsy side hustle.

          Notes from Chris
          Episode 3267

          Welcome to Throwback Thursday, where we take an in-depth look at someone who’s story has evolved considerably since we first featured them.

          Last week, we heard how one small campaign tool turned into a niche software product now licensed by multiple counties.

          Today, in our latest feature, we’ll discover how one maker rescued stained recipe cards and transformed them into framed kitchen art. Her sentimental side hustle—complete with a done-for-you option—has already brightened 150 homes and counting.

          Listen to today’s episode to hear more…

           

           

           

          SEE ALSO:

          • Raver Turns LED-Powered Gloves Into Bright Future: When a raver-turned-salesperson falls in love with an underground art form, he turns it into a successful side business.
          • Bright Idea Leads Chicago Woman to Million-Dollar Hustle: A Chicago-based plastic recycling sales rep overcomes her fears and doubts to transform her love for DIY lamp shades and $10 in supplies into a multi-million dollar business.
          • 3D Printing Brings Cosplay Into 21st Century: With a 3D printer and sense of imagination, a California natural gas industry worker takes superhero DIY cosplay to a whole new level.
          • Inspiration is good; inspiration combined with action is better. Now get back to work!

            Yours in the revolution,

            <img class="alignnone wp-image-1825" src="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png" alt="cg-sig-newsletter" width="176" height="82" srcset="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png 300w, https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter.png 450w" sizes="(max-width: 176px) 100vw, 176px">

            Resources
            CREATE YOUR ONLINE STORE

            Create your online store with Shopify using an exclusive discount for Side Hustle School listeners. For a limited time, get a free 21-day trial and a 10% discount for a whole year.

            Many Side Hustle School listeners are building sites using Shopify's easy-to-learn platform. Try it free today!

            Learn More

            GET YOUR FIRST 1,000 EMAIL SUBSCRIBERS

            Social media is nice, but building an email list is still the single best way to get customers and clients for your hustle. It's not hard to get started—sign up for a 30-day trial and join the list-building challenge! You’ll be up and running in no time.

            Learn More

            Sponsors & Gratitude
            Don't Do Business Without It

            Side Hustle School is brought to you by American Express.

            No matter what you do in business, from working nine-to-five to working five-to-nine, it’s easier when you don’t go it alone. Get the powerful backing of American Express—don't do business without it! 💳

            Visit American Express

            Like the Show? Leave a Rating!

            Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference! ✅

            It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.

            Here's How

            Keep in Touch
            <img class="aligncenter wp-image-1272 size-full" src="https://sidehustleschool.com/wp-content/uploads/2017/03/ChrisGuillebeauSideHustleSchoolFull-1.jpg" width="1076" height="251">
            There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

            Follow

            Facebook,Instagram,Twitter

            Email

            Say Hi

            From your favorite airport

            To infinity and beyond,

            Chris Guillebeau
            8 min
          • Marathon Runner Earns Full-Time Income Trying On Shoes
            What It’s About
            A patient runner turns a decade of shoe-testing into a six-figure affiliate business.

            Notes from Chris
            Episode 3266

            In today’s story…

            ..this patient runner starts a running shoe review site, first because he’s bored, then as a hobby, then as a passion project, a side hustle that brings in a whopping $9 in month one, but—after miles of pounding the pavement—turns into a real moneymaker.

            Listen to today’s episode to learn more…

             

             

            SEE ALSO:

            • Catholic Designer Creates Stylish Apparel Line: What shall it profit a man to gain the whole world but not sell any t-shirts? This designer cast his bread upon the waters and ended up with a profitable fashion line.
            • Seattle Couple Creates New “Income LiveStream”: When a married couple runs into logistical problems at their wedding, it leads to an innovative service that other engaged couples need during the pandemic.
            • Role-Playing Pastor Rolls The Dice On $2800/Month Hustle: Listener success story! This Presbyterian minister turns to his lifelong interest in role-playing games to set up a sustainable second income source.
            • Inspiration is good; inspiration combined with action is better. Now get back to work!

              Yours in the revolution,

              <img class="alignnone wp-image-1825" src="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png" alt="cg-sig-newsletter" width="176" height="82" srcset="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png 300w, https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter.png 450w" sizes="(max-width: 176px) 100vw, 176px">

              Resources
              GET $625 IN FREE TRAVEL

              Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

              I use this card every day all over the world! ✈️

              Learn More

              CREATE YOUR ONLINE STORE

              Create your online store with Shopify using an exclusive discount for Side Hustle School listeners. For a limited time, get a free 21-day trial and a 10% discount for a whole year.

              Many Side Hustle School listeners are building sites using Shopify's easy-to-learn platform. Try it free today!

              Learn More

              Sponsors & Gratitude
              Learn More With Skillshare!

              Supporting the sponsors keeps the show free. Today’s episode of Side Hustle School is brought to you by Skillshare. 📷

              Skillshare is giving Side Hustle School listeners 2 months of unlimited access—for $0.99! Join the 2 million students learning everything from street photography to SEO on Skillshare today!

              Get Started Here!

              Like the Show? Leave a Rating!

              Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference! ✅

              It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.


              Here's How

              Keep in Touch
              <img class="aligncenter wp-image-1272 size-full" src="https://sidehustleschool.com/wp-content/uploads/2017/03/ChrisGuillebeauSideHustleSchoolFull-1.jpg" width="1076" height="251">
              There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

              Follow

              Facebook,Instagram,Twitter

              Email

              Say Hi

              From your favorite airport

              To infinity and beyond,

              Chris Guillebeau
              7 min
            • Q&A: “Should I add shipping to my Marketplace listings?”
              What It’s About
              Is shipping a smart expansion for a local-only Marketplace seller?

              Notes from Chris
              Episode 3265

              Opening the door to shipping can 3–10x your buyer pool—especially for collectibles—but it also introduces new headaches: bad payments, chargebacks, and boxes arriving in pieces. The trick is to start narrow, use platforms that include buyer/seller protection, and set up packing and payment rules you never break. Let’s walk through a cautious rollout.

              “I list furniture and collectibles locally on Facebook Marketplace with ‘pickup only’ in the description. Lately buyers keep asking me to ship, sometimes offering to prepay through sketchy methods. I know shipping could expand my pool of customers, but I’m worried about scams, returns, and damage. Is it worth adding shipping as a growth lever, and if so, what safeguards—payment platforms, packaging techniques—help a small seller avoid getting burned?”

              Listen to today’s episode to learn more…

               

               

              SEE ALSO:

              • Catholic Designer Creates Stylish Apparel Line: What shall it profit a man to gain the whole world but not sell any t-shirts? This designer cast his bread upon the waters and ended up with a profitable fashion line.
              • Seattle Couple Creates New “Income LiveStream”: When a married couple runs into logistical problems at their wedding, it leads to an innovative service that other engaged couples need during the pandemic.
              • Role-Playing Pastor Rolls The Dice On $2800/Month Hustle: Listener success story! This Presbyterian minister turns to his lifelong interest in role-playing games to set up a sustainable second income source.
              • Inspiration is good; inspiration combined with action is better. Now get back to work!

                Yours in the revolution,

                <img class="alignnone wp-image-1825" src="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png" alt="cg-sig-newsletter" width="176" height="82" srcset="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png 300w, https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter.png 450w" sizes="(max-width: 176px) 100vw, 176px">

                Resources
                GET $625 IN FREE TRAVEL

                Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

                I use this card every day all over the world! ✈️

                Learn More

                CREATE YOUR ONLINE STORE

                Create your online store with Shopify using an exclusive discount for Side Hustle School listeners. For a limited time, get a free 21-day trial and a 10% discount for a whole year.

                Many Side Hustle School listeners are building sites using Shopify's easy-to-learn platform. Try it free today!

                Learn More

                Sponsors & Gratitude
                Learn More With Skillshare!

                Supporting the sponsors keeps the show free. Today’s episode of Side Hustle School is brought to you by Skillshare. 📷

                Skillshare is giving Side Hustle School listeners 2 months of unlimited access—for $0.99! Join the 2 million students learning everything from street photography to SEO on Skillshare today!

                Get Started Here!

                Like the Show? Leave a Rating!

                Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference! ✅

                It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.


                Here's How

                Keep in Touch
                <img class="aligncenter wp-image-1272 size-full" src="https://sidehustleschool.com/wp-content/uploads/2017/03/ChrisGuillebeauSideHustleSchoolFull-1.jpg" width="1076" height="251">
                There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

                Follow

                Facebook,Instagram,Twitter

                Email

                Say Hi

                From your favorite airport

                To infinity and beyond,

                Chris Guillebeau
                8 min
              • First $1,000: Flipping Rolling Carts & Filing Cabinets
                What It’s About
                A few coats of paint turn free rolling cabinets into a fast $1,000 flip.

                Notes from Chris
                Episode 3264

                Today’s episode is part of a feature we call ‘Your First $1,000.’ As you might surmise from the title, this is all about how someone made their first $1,000.

                How did they get to that point? Not their first $100,000—that’s cool, but it would probably be a long story.

                But what about their first $1,000—how did they make that happen, what did it feel like, and what did they learn?

                Let’s hear today’s story. I’ll be back at the end to wrap us up. 

                 

                 

                SEE ALSO:

                • Military Spouse Starts Subscription Box Mission:When an HR Director’s husband is away on military deployment, she uses the alone time to march toward a subscription box.
                • Think Inside the Subscription Box:Looking for more community, a North Carolina web agency owner starts a subscription box for female entrepreneurs. It’s supposed to be a referral tool for her agency, but it ends up becoming a full-time business of its own.
                • Nature-Loving Neighbors Create Kids Subscription Box: When two couples can’t figure out how to get their kids outdoors and away from electronics in the winter, a personal challenge blossoms into an unbeLEAFable side hustle.
                • Inspiration is good; inspiration combined with action is better. Now get back to work!

                  Yours in the revolution,

                  <img class="alignnone wp-image-1825" src="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png" alt="cg-sig-newsletter" width="176" height="82" srcset="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png 300w, https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter.png 450w" sizes="(max-width: 176px) 100vw, 176px">

                  Resources
                  WEB HOSTING @ $2.49/MONTH

                  Want to build any kind of website for your hustle? If so, you'll need somewhere to host it! This is the reliable company I've used for many websites. It's cheap, flexible, and offers support 24-7.

                  Get your own hosting plan for just $2.49 a month!

                  Learn More

                  GET $625 IN FREE TRAVEL

                  Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

                  I use this card every day all over the world! ✈️

                  Learn More

                  Sponsors & Gratitude
                  Don't Do Business Without It

                  Side Hustle School is brought to you by American Express.

                  No matter what you do in business, from working nine-to-five to working five-to-nine, it’s easier when you don’t go it alone. Get the powerful backing of American Express—don't do business without it! 💳

                  Visit American Express

                  Like the Show? Leave a Rating!

                  Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference! ✅

                  It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.

                  Here's How

                  Keep in Touch
                  <img class="aligncenter wp-image-1272 size-full" src="https://sidehustleschool.com/wp-content/uploads/2017/03/ChrisGuillebeauSideHustleSchoolFull-1.jpg" width="1076" height="251">
                  There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

                  Follow

                  Facebook,Instagram,Twitter

                  Email

                  Say Hi

                  From your favorite airport

                  To infinity and beyond,

                  Chris Guillebeau
                  7 min
                • Weekend Workshop: The “Never Boss” Philosophy
                  What It’s About
                  A “company of one” proves you can build a thriving business without bosses—or employees.

                  Notes from Chris
                  Episode 3263

                  It’s Weekend Workshop, and it’s new!

                  Listen to today’s episode to learn more…

                   

                   

                  SEE ALSO:

                  • Catholic Designer Creates Stylish Apparel Line: What shall it profit a man to gain the whole world but not sell any t-shirts? This designer cast his bread upon the waters and ended up with a profitable fashion line.
                  • Seattle Couple Creates New “Income LiveStream”: When a married couple runs into logistical problems at their wedding, it leads to an innovative service that other engaged couples need during the pandemic.
                  • Role-Playing Pastor Rolls The Dice On $2800/Month Hustle: Listener success story! This Presbyterian minister turns to his lifelong interest in role-playing games to set up a sustainable second income source.
                  • Inspiration is good; inspiration combined with action is better. Now get back to work!

                    Yours in the revolution,

                    <img class="alignnone wp-image-1825" src="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png" alt="cg-sig-newsletter" width="176" height="82" srcset="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png 300w, https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter.png 450w" sizes="(max-width: 176px) 100vw, 176px">

                    Resources
                    GET $625 IN FREE TRAVEL

                    Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

                    I use this card every day all over the world! ✈️

                    Learn More

                    CREATE YOUR ONLINE STORE

                    Create your online store with Shopify using an exclusive discount for Side Hustle School listeners. For a limited time, get a free 21-day trial and a 10% discount for a whole year.

                    Many Side Hustle School listeners are building sites using Shopify's easy-to-learn platform. Try it free today!

                    Learn More

                    Sponsors & Gratitude
                    Learn More With Skillshare!

                    Supporting the sponsors keeps the show free. Today’s episode of Side Hustle School is brought to you by Skillshare. 📷

                    Skillshare is giving Side Hustle School listeners 2 months of unlimited access—for $0.99! Join the 2 million students learning everything from street photography to SEO on Skillshare today!

                    Get Started Here!

                    Like the Show? Leave a Rating!

                    Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference! ✅

                    It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.


                    Here's How

                    Keep in Touch
                    <img class="aligncenter wp-image-1272 size-full" src="https://sidehustleschool.com/wp-content/uploads/2017/03/ChrisGuillebeauSideHustleSchoolFull-1.jpg" width="1076" height="251">
                    There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

                    Follow

                    Facebook,Instagram,Twitter

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                    Say Hi

                    From your favorite airport

                    To infinity and beyond,

                    Chris Guillebeau
                    6 min
                  • Q&A: “Should I raise my coaching rates or add more clients?”
                    What It’s About
                    Will a modest rate bump outrun the hustle of adding more clients?

                    Notes from Chris
                    Episode 3262

                    Service businesses hit a hard ceiling: a week only holds so many billable hours. When the calendar is close to full, growth comes down to choosing the right lever—charge a bit more or squeeze in more sessions. One path protects energy and often improves perceived value; the other risks dilution, context switching, and creeping burnout.

                    Today’s caller doesn’t need a rebrand or a funnel—just clear math and a small, real-world test. Price the next couple of inquiries at the higher rate, set a firm session cap, and let behavior (not fear) decide. We’ll show how a modest fee bump can lift profit per hour without sacrificing quality.

                    “I’m a lifestyle improvement coach billing around 20 client hours a week at $100 per session. My calendar is already near capacity, so growth options feel limited. I keep debating: is it better to raise my rates by 10% for existing and new clients, or pour effort into marketing to land 10% more people at the current price? I’m worried a price increase triggers churn, but I also don’t want to burn out chasing more clients for the same money. How do I figure out which lever—price or volume—will actually improve net profit fastest?”

                    Listen to today’s episode to learn more…

                     

                     

                    SEE ALSO:

                    • Catholic Designer Creates Stylish Apparel Line: What shall it profit a man to gain the whole world but not sell any t-shirts? This designer cast his bread upon the waters and ended up with a profitable fashion line.
                    • Seattle Couple Creates New “Income LiveStream”: When a married couple runs into logistical problems at their wedding, it leads to an innovative service that other engaged couples need during the pandemic.
                    • Role-Playing Pastor Rolls The Dice On $2800/Month Hustle: Listener success story! This Presbyterian minister turns to his lifelong interest in role-playing games to set up a sustainable second income source.
                    • Inspiration is good; inspiration combined with action is better. Now get back to work!

                      Yours in the revolution,

                      <img class="alignnone wp-image-1825" src="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png" alt="cg-sig-newsletter" width="176" height="82" srcset="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png 300w, https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter.png 450w" sizes="(max-width: 176px) 100vw, 176px">

                      Resources
                      GET $625 IN FREE TRAVEL

                      Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

                      I use this card every day all over the world! ✈️

                      Learn More

                      CREATE YOUR ONLINE STORE

                      Create your online store with Shopify using an exclusive discount for Side Hustle School listeners. For a limited time, get a free 21-day trial and a 10% discount for a whole year.

                      Many Side Hustle School listeners are building sites using Shopify's easy-to-learn platform. Try it free today!

                      Learn More

                      Sponsors & Gratitude
                      Learn More With Skillshare!

                      Supporting the sponsors keeps the show free. Today’s episode of Side Hustle School is brought to you by Skillshare. 📷

                      Skillshare is giving Side Hustle School listeners 2 months of unlimited access—for $0.99! Join the 2 million students learning everything from street photography to SEO on Skillshare today!

                      Get Started Here!

                      Like the Show? Leave a Rating!

                      Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference! ✅

                      It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.


                      Here's How

                      Keep in Touch
                      <img class="aligncenter wp-image-1272 size-full" src="https://sidehustleschool.com/wp-content/uploads/2017/03/ChrisGuillebeauSideHustleSchoolFull-1.jpg" width="1076" height="251">
                      There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

                      Follow

                      Facebook,Instagram,Twitter

                      Email

                      Say Hi

                      From your favorite airport

                      To infinity and beyond,

                      Chris Guillebeau
                      8 min
                    • Q&A: “Is my struggling side hustle worth saving?”
                      What It’s About
                      Is a slow-starting side hustle a normal lull or a sign to pivot?

                      Notes from Chris
                      Episode 3261

                      Not every side hustle explodes. Many take a year to stabilize. But eight months of nightly effort for only six hundred dollars is a signal that something—pricing, product, marketing, or audience—isn’t working. The goal isn’t to defend the project or kill it out of fear; it’s to run a structured test so emotion (yours or your spouse’s) doesn’t make the decision.

                      A slow start isn’t failure; it’s information. The real issue here isn’t just profit—it’s what matters most to the creator: creative satisfaction, extra income, or a path to replacing a job. Her spouse’s concern is valid, but this decision is hers. The goal is to clarify why she’s doing it, then run a focused experiment so the answer doesn’t come from emotion or pressure.

                      “I’ve been crafting for a while, and I spend nights knitting quirky pet sweaters and selling them on Etsy. After eight months on the marketplace I’ve netted about $600 total, and my spouse says the time might be better spent on freelance work that pays immediately. Part of me thinks every business needs a slow burn; another part worries I’m ignoring solid feedback. How do you tell the difference between healthy persistence and stubborn denial—especially when the person questioning you is someone you trust?”

                      Listen to today’s episode to learn more…

                       

                       

                      SEE ALSO:

                      • Catholic Designer Creates Stylish Apparel Line: What shall it profit a man to gain the whole world but not sell any t-shirts? This designer cast his bread upon the waters and ended up with a profitable fashion line.
                      • Seattle Couple Creates New “Income LiveStream”: When a married couple runs into logistical problems at their wedding, it leads to an innovative service that other engaged couples need during the pandemic.
                      • Role-Playing Pastor Rolls The Dice On $2800/Month Hustle: Listener success story! This Presbyterian minister turns to his lifelong interest in role-playing games to set up a sustainable second income source.
                      • Inspiration is good; inspiration combined with action is better. Now get back to work!

                        Yours in the revolution,

                        <img class="alignnone wp-image-1825" src="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png" alt="cg-sig-newsletter" width="176" height="82" srcset="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png 300w, https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter.png 450w" sizes="(max-width: 176px) 100vw, 176px">

                        Resources
                        GET $625 IN FREE TRAVEL

                        Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

                        I use this card every day all over the world! ✈️

                        Learn More

                        CREATE YOUR ONLINE STORE

                        Create your online store with Shopify using an exclusive discount for Side Hustle School listeners. For a limited time, get a free 21-day trial and a 10% discount for a whole year.

                        Many Side Hustle School listeners are building sites using Shopify's easy-to-learn platform. Try it free today!

                        Learn More

                        Sponsors & Gratitude
                        Learn More With Skillshare!

                        Supporting the sponsors keeps the show free. Today’s episode of Side Hustle School is brought to you by Skillshare. 📷

                        Skillshare is giving Side Hustle School listeners 2 months of unlimited access—for $0.99! Join the 2 million students learning everything from street photography to SEO on Skillshare today!

                        Get Started Here!

                        Like the Show? Leave a Rating!

                        Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference! ✅

                        It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.


                        Here's How

                        Keep in Touch
                        <img class="aligncenter wp-image-1272 size-full" src="https://sidehustleschool.com/wp-content/uploads/2017/03/ChrisGuillebeauSideHustleSchoolFull-1.jpg" width="1076" height="251">
                        There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

                        Follow

                        Facebook,Instagram,Twitter

                        Email

                        Say Hi

                        From your favorite airport

                        To infinity and beyond,

                        Chris Guillebeau
                        7 min

                      About Side Hustle School

                      From the publisher's feed

                      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…