Tag: Upwork

7th Grade Teacher Earns 2nd Income Writing Resumes

What It’s About

A teacher finds a profitable extra-curricular activity using his writing skills.

[podcast_details]

Words of Wisdom

Greg offers some wise advice for those seeking to launch a side hustle, “Make sure your day job is secure first. That’s your bread and butter!”

Fun Fact

Greg likes to keep his business in the family and hired his brother to design his logo.

Notes from Chris

Episode 1730
Greg Marano has had a lifelong obsession with writing. He’d penned his first book before leaving Elementary School. Fast-forward a few decades, and Greg’s dreams of writing had turned out a little differently than expected.

In some ways, he’d acheived them: he was working as a columnist for The Poughkeepsie Journal—his local newspaper—but he found writing for a living left little creative energy to write for fun. He eventually quit his job to explore other things, finally ending up as an English teacher. That was the stable role he stuck with.

While teaching literature and poetry to seventh-graders, he found himself with renewed energy and a desire to write again. With a new baby at home, a little side hustle income also wouldn’t hurt. So, he toyed with the idea of freelance writing.

Greg created a profile on the marketplace UpWork and began offering his services. At first he focused on general writing needs: proofreading, ghostwriting, and blogging, feeling a broad scope would give him the best chance of success. He also set his prices relatively low, a decision he says, in hindsight, was driven more by fear of rejection than trying to undercut the market.

Greg slowly began moving his clients away from UpWork and worked with them directly. This allowed him to cut out the middleman and commission fees to keep more of the income for himself. That was important if he wanted to raise his prices.

Where do the customers come from? Well, Greg generates a consistent stream of leads for his business by using Google’s display ads. After a particularly dry month without much website traffic, he knew he needed to be more active in his approach, so he budgeted $50 to target people searching for keywords around resumes. It was a figure he was willing to lose if it didn’t work out. Thankfully, it generated enough interest to more than cover the cost, and he began to slowly increase the monthly budget until he reached a comfortable workload.

Looking to the future, Greg is happy to stay on his current path. He knows the only way to scale his business would be to hire people, and he can’t imagine himself doing that any time soon. After all, managing a class of seventh graders is enough hard work.

 

 

MENTIONED IN THIS EPISODE:

SEE ALSO:

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

Yours in the revolution,

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Resources

GET $625 IN FREE TRAVEL

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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

Quote of the Day
"Make sure your day job is secure first. That’s your bread and butter!"
—Greg Marano #SideHustleSchool

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. 📷

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To infinity and beyond,

Chris Guillebeau

Dorm Room Side Hustle Grows Into Full Agency

What It’s About

A six-figure side hustle started live from a college dorm room.

[podcast_details]

Words of Wisdom

Trevor shares some important nuggets, “Take action each and every single day. I applied to freelancing jobs like my life depended on it. This allowed me to figure out what I liked to do and didn’t.”

Fun Fact

A market research company valued the global podcasting industry at $9.28 billion in 2019 and said they expect it to grow at an annual rate of 27.5% between now and 2027.

Notes from Chris

Episode 1513
You know those cartoons where the character is running down a hill while what started as a tiny snowball rolls after him, growing bigger and bigger as it picks up steam? The snowball grows of its own accord, helped along only by gravity. Now, leaving aside the part at the end where the character ends up smooshed inside the giant snowball, arms and legs akimbo, a lot of side hustles have a similar trajectory. What starts as a small snowball can take on a life of its own, becoming less “side” hustle and more of, well, a main hustle.

Trevor Oldham’s story is just like that. Born of a desire for a job in college that allowed him to be his own boss, Trevor’s side hustle, Podcasting You, graduated to become his full-time job. He rolled that snowball down a hill and found himself at the bottom, owner of a small business that books podcast guests and brings in upwards of $15,000 a month.

One day he came across a listing on Upwork from a real estate investor in Los Angeles who was looking for help getting booked as a guest on podcasts as a way to promote her services. Trevor had booked guests for his own podcast, so he figured he could easily do the reverse.

He began to find more clients who needed help getting booked on podcasts, fielding calls in his dorm room in between classes (his clients at the time may not have realized how young Trevor actually was). Pretty quickly he realized that booking guests was more lucrative and less time consuming than the editing work he’d been doing. Podcasting You was born.

Trevor’s initial investment in his company was less expensive than a dorm room meal of instant ramen. He had no website, no inventory, no employees. Other than the time it took him to look for clients on Upwork, he spent exactly $0 getting started. Today Podcasting You brings in between $12,000 and $15,000 in revenue each month.

 

 

MENTIONED IN THIS EPISODE:

  • Learn more about Josh and his company’s services at their website, Podcasting You .

SEE ALSO:

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

Yours in the revolution,

cg-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 |

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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

Quote of the Day
"Take action each and every single day. I applied to freelancing jobs like my life depended on it. This allowed me to figure out what I liked to do and didn’t."
—Trevor Oldham #SideHustleSchool

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

Graphic Designer Documents Remote Earnings

What It’s About

A graphic designer draws up a full-time nomadic lifestyle doing freelance work.

[podcast_details]

Words of Wisdom

Kassandra shares the importance of ratings for freelance work, “Just with a single UpWork rating, I managed to go from applying for 50 jobs a week and getting no bites to applying for 50 jobs and getting one or two jobs from it.”

Fun Fact

UpWork has 12 million registered freelancers but perhaps more importantly, over five million employers looking for workers. It’s a great way to get your feet wet in the world of freelancing.

Notes from Chris

Episode 1443
Kassandra Marsh spent years studying graphic design in Australia. She enjoyed it and was excited to get out into the world, assuming she’d start a high flying job the moment she graduated. But, unbeknownst to her, there was no job waiting. Not for another long, arduous twelve months.

Until a job ad in the local newspaper caught her eye.

The ad described a job for someone with experience working with kids, along with an ability to design business documents. Kassandra, thinking it was such a curious mix of the two skills, applied straight away. After all, she was the ideal candidate!

Turns out, the job posting was an accident—the company erroneously placed a single ad for two jobs, instead of two ads for single jobs. Even so, Kassandra’s mix of skills surprised them and they agreed to hire her on a freelance basis. Her job would be to take their dull business documents, and redesign them so they were off the charts!

It wasn’t sustainable relying on only one client, so she set out to find more. To do that, she posted a profile on oDesk—which is now called UpWork—and promptly received … very little attention. Like zero divided by zero attention.

Kassandra modified the one variable she could: her prices. She gradually dropped her rate until she had someone employ her at the going price. It would mean working for peanuts but hopefully scoring a few prized reviews after nailing the job.

Eventually, she found an equilibrium, where she could charge the maximum amount possible yet still receive responses to her bids. Kassandra would often use a trick to ‘lever’ her pricing and schedule. When really busy, she’d price herself highly, to justify taking on additional work. When things were a little slower, she would drop her prices to drum up interest.

Between the website and her UpWork client stream there’s no shortage of gigs available to Kassandra. She now earns over twenty-six thousand US dollars per year, all while living remotely.

 

 

MENTIONED IN THIS EPISODE:

  • Learn more about Kassandra and her business from her website, Lakazdi.com .

SEE ALSO:

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

Yours in the revolution,

cg-sig-newsletter

Download Episodes By Months:

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

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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

Quote of the Day
"I am really glad to have got to learn through mistakes and build a nice business for myself."
—Kassandra Marsh #SideHustleSchool

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

Recruiter Moonlights on HR Jobs Marketplace

What It’s About

If you think an online jobs marketplace is lacking, try creating your own.

Words of Wisdom

Hear Chris’s valuable advice regarding niches: “Find an underserved niche and go after it. I had noticed some other niche gig sites starting up for certain industries and that got me thinking how many industries could eventually support their own gig marketplace.”

Fun Fact

Upwork is the largest freelance marketplace in the world. Currently it has 12 million registered freelancers and five million registered employers. It skews towards tech related projects leaving plenty of room for well marketed niche related offerings.

Notes from Chris

Episode 1291
It was five years ago when Chris Russell lost his job as a Director of Digital Recruiting. Having his income instantly halted was tough … but Chris still possessed all the skills that made him a valuable employee, even though he no longer was one. His ability to find good candidates and place them in the right jobs with minimal headache was a skill lots of businesses needed.

So, instead of diving in and looking for another 9-5 job, Chris decided to try his hand at freelancing. And for the next five years he made a living doing just that. He’d hustle, find temporary work somewhere among the large network he’d built up during his career, then move onto the next gig.

It was a flexible but not always lucrative arrangement. Chris was always on the lookout for his next gig. He often had periods where he wasn’t sure if the next one would even come.

In an effort to find something different Chris investigated the website Upwork, the world’s largest marketplace for freelancers. There he found some people looking for HR experts, but since Upwork skews more toward tech projects they were few and far between. Also, Upwork takes a large commission from each job, sometimes making it prohibitively expensive to use.

Chris felt like there had to be another way. And if there wasn’t, he was starting to think he was as good a person as any to make one.

His time on Upwork showed a need for a cheaper, niche version of the site aimed specifically at the HR industry. In his vision, just like Upwork, employers could post jobs on the site and freelancers could submit proposals to complete that work.

So instead of going the difficult route, Chris scoured the web looking for an ‘out of the box’ solution; a pre-made piece of software that he could simply purchase as is. You can find these for a lot of different sites. They allow you to pay to effectively create a clone of an existing site’s functions using your own branding.

Best of all was that he was able to install and configure it himself.

At the same time, he identified a dozen HR consultants he thought would be a good fit and contacted them, letting them know his new service would be a place that had regular gigs for freelance HR consultants. Almost immediately someone committed to a yearly subscription for eighty-nine dollars.

That’s when Chris knew he was onto something. He hadn’t even officially launched, and yet someone still believed in the concept enough that they were willing to put real money down.

He ‘officially’ launched HRLancers.com in January 2020. He posted about it to all of his Connections and mentioned it in the groups he was a part of. So what happened?

Well, in the first thirty days HRLancers.com received five thousand website visitors and hundreds of HR experts signed up to the service—most of them on the free version he offered, but some for the paid service, which offered featured placement on posts. Companies were posting gigs, and freelancers were applying for them.

The coronavirus slowdown isn’t stopping Chris. He’s continuing to network and attract more interest in the site. It’s nowhere near a full-time gig yet, so he still relies heavily on his own freelancing to make a living. But he is hoping that one day HRLancers.com will turn into the big promotion he always wanted, and aid in securing his financial future.

 

 

MENTIONED IN THIS EPISODE:

  • Check out Chris’s website, HRLancers.com.
  • Looking to freelance (or just curious about job marketplaces), check out sites like Upwork and Fiverr.
  • Stripe: a popular online payment processor for those looking to sell something on their website.

SEE ALSO:

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

Yours in the revolution,

cg-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

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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

Quote of the Day
"Find an underserved niche and go after it. I had noticed some other niche gig sites starting up for certain industries and that got me thinking how many industries could eventually support their own gig marketplace."
—Chris Russell #SideHustleSchool

Sponsors & Gratitude

Try ShipStation for 60 Days FREE!

Today’s episode of Side Hustle School is brought to you by ShipStation, the #1 choice of online sellers. 📦

To get a 30-day trial AND an additional month free, click the microphone at the top of their page and enter the word HUSTLE.
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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