7 min 38 sec

Tie One On for This Australian High School Teacher

To get some business experience on the cheap, this teacher creates and sells his own bow ties. When he’s ready to move on, he sells the business itself.
International Product Reselling Transition Story

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What It's About

Knowing when to give up can be tough, but this high school teacher knew when it was time to put a bow on it.

Business Model
Skills Required
Resourcefulness & Problem Solving
Profit Potential

Words of Wisdom

I am a big fan of moving on! Life is short and you’re already busy, so you should spend your limited time on something you’re excited about and believe in. What do you do when you’re no longer passionate about the project you started, or you recognize that to grow it would require more time and resources you don’t have—is there a way you can profit by making a change?

Fun Fact

Croatian soldiers in the Thirty Years War (1618-1648) were one of the first documented peoples to don a necktie, which they used to keep together the collars of their shirts. French soldiers brought the look back home with them after the war, and by the 1700s, neckties were widely adopted by the upper classes, marking the time when neckties became a main feature in men’s dress.

Notes from Chris

Episode 629

Vince Massara is a high school teacher living in Victoria, Australia. On the side, he now runs a small business that helps other teachers learn more about the side hustle world. However, it was by way of his first income generating project that led him to what he’s doing today… and that’s what we’re going to look at here.

That first project was called Why Knot Ties.

Vince started Why Knot Ties on a whim. Hence the title, “Why Knot.” He thought that at worst, it would make for a funny story down the road. He pictured himself saying to his friends, “Hey, remember when I tried to sell bow ties? Wasn’t that silly.”

As whimsical as it was, Vince notes that there was an underlying reason behind it. He described it as “that feeling of being able to do almost anything when you look and feel like your best self.” He wanted to provide that feeling of confidence for people every day through Why Knot Ties.

The idea of solving new problems excited Vince, and he wanted a new challenge. He also viewed it as a cheap business school and figured that he had nothing to lose.

In less than a year, Why Not Ties was regularly earning between $500 to $1,000 a month.

Normally at this point, I would tell you what he was doing next to grow it further. But no! I warned you this was a different story—here’s what happened.

Despite making that $500-1,000/month, Vince admits he misjudged the online marketplace for fashion. The barriers were too great to truly scale. Most customers were unwilling to leave their marketplace site to buy a mid-priced bow tie.

Also, Vince fell out of love with the brand and with the fashion business in general. Even with the goal of increasing people’s confidence in mind, ultimately it didn’t feel as though he was helping anybody. Which, as an educator, is hard-wired into him.

Last but not least, you could say that he didn’t want to get tied down.

Since he went into Why Knot with a “nothing to lose” mentality, when he was no longer excited about it, he was content with giving it up. But instead of just walking away, he sold the brand and remaining inventory for $5,000. This included the website, stock, and yet-to-be published exposure in GQ magazine.

There were other benefits. Vince began incorporating the lessons learned from Why Knot Ties into the classroom. It rejuvenated his teaching and turned teacher-led innovation into his new passion.

The skills he now uses in his new side hustle, The Content Friends, are almost entirely things he learned from Why Knot. Entering the online business world, Vince noticed that referrals were by far the biggest way of getting qualified leads and new customers. Most people he spoke to who had businesses were filtering money into Facebook ads. However, most of them didn’t have a system for generating leads or referrals.

That was something Vince was able to do with Why Knot, so now he’s teaching it to others. He recently started a blog and podcast, The Smart Edupreneur, about the need for change in education through teacher-led innovation. He blogs on the topic at his personal website. His podcast, The Smart Edupreneur, can be heard there too.

The bow-tie hustle is all tied up, but Vince is moving on with a fashionable future.


  • Why Knot Ties: If you're interested in gender neutral bow ties and other accessories, check out the business that Vince sold
  • The Content Friends: Vince has learned quite a bit about what it takes to start a side hustle as a full-time teacher. Learn more about his new side hustle helping other teachers on his website, and learn more about Vince and what he's up to over on his personal website!
  • The Smart Edupreneur: If you're looking for a new podcast, check out Vince's podcast as well
  • WordPress: Vince used WordPress to setup Why Knot Ties, and here you can learn how to install your own WordPress site in 5 minutes
  • Alibaba: The platform that Vince used to locate a manufacturer for his bow ties

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

Yours in the revolution,


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Quote of the Day
"If a teacher wanted to start their own side hustle, I’d suggest starting small. If you’re unsure what business to start and you’d like to learn the basics, there is a market where you can sell your own teaching resources online. It’s a business with an extremely low barrier to entry, and odds are you already have some amazing resources. You’ll also quickly pick up bits and pieces of the online business game."
—Vince Massara #SideHustleSchool

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When the rest of the world is still zigging, some companies know when it’s time to zag. Elizabeth Banks has teamed up with State Street Global Advisors to make a series of podcasts and films that uncover the bold moves mid-cap companies make to thrive and survive.

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To infinity and beyond,

Chris Guillebeau