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Q&A: “When is it worth spending money on your side hustle?”

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Manage episode 479201997 series 2526728
Content provided by Chris & Jolie Guillebeau and Chris Guillebeau. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Chris & Jolie Guillebeau and Chris Guillebeau or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://staging.podcastplayer.com/legal.

What It’s About

Side hustles keep getting cheaper…

Notes from Chris

Episode 3038
Starting a side hustle often means getting creative with limited resources—using what you have, borrowing what you don’t, and learning to do more with less. But as your hustle grows, the question of when to invest in tools or services becomes critical.

Today’s question comes from Clara in Toronto, who launched her business with just $50 and a borrowed camera. She wants to know how to balance staying scrappy with making smart investments to scale. Let’s dive into how to decide where to spend and where to save.

“Hi Chris, this is Clara calling from Toronto. My side hustle kicked off with just $50, a borrowed camera, and a lot of DIY spirit. Over time, I’ve seen some success, and now I’m torn about when—and where—to start spending real money. I love the creativity that comes from working with almost nothing, but I also know I might be missing out on growth if I don’t invest in the right tools or services. How do I figure out what’s absolutely worth paying for, and what I should keep hacking together on my own so I don’t lose the scrappy approach that got me here?”

Listen to today’s episode to learn more…


SEE ALSO:

Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,

cg-sig-newslettercg-sig-newsletter


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Season 3 (2019): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 2 (2018): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 1 (2017): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

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

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!


To infinity and beyond,

Chris Guillebeau
  continue reading

27 episodes

Artwork
iconShare
 
Manage episode 479201997 series 2526728
Content provided by Chris & Jolie Guillebeau and Chris Guillebeau. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Chris & Jolie Guillebeau and Chris Guillebeau or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://staging.podcastplayer.com/legal.

What It’s About

Side hustles keep getting cheaper…

Notes from Chris

Episode 3038
Starting a side hustle often means getting creative with limited resources—using what you have, borrowing what you don’t, and learning to do more with less. But as your hustle grows, the question of when to invest in tools or services becomes critical.

Today’s question comes from Clara in Toronto, who launched her business with just $50 and a borrowed camera. She wants to know how to balance staying scrappy with making smart investments to scale. Let’s dive into how to decide where to spend and where to save.

“Hi Chris, this is Clara calling from Toronto. My side hustle kicked off with just $50, a borrowed camera, and a lot of DIY spirit. Over time, I’ve seen some success, and now I’m torn about when—and where—to start spending real money. I love the creativity that comes from working with almost nothing, but I also know I might be missing out on growth if I don’t invest in the right tools or services. How do I figure out what’s absolutely worth paying for, and what I should keep hacking together on my own so I don’t lose the scrappy approach that got me here?”

Listen to today’s episode to learn more…


SEE ALSO:

Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,

cg-sig-newslettercg-sig-newsletter


Download Episodes By Months:

Season 9 (2025): JAN | FEB | MAR |

Season 8 (2024): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 7 (2023): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 6 (2022): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 5 (2021): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 4 (2020): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 3 (2019): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 2 (2018): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 1 (2017): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

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

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!


To infinity and beyond,

Chris Guillebeau
  continue reading

27 episodes

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