8 min 35 sec

Business Besties Turn Skype Calls Into Six-Figure Podcast

After two friends create a podcast for fun, it turns into a side hustle that generates $100,000 in its first year, multiple six-figures in year two, and a book deal in year three.
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What It's About

Two friends start a podcast to share their wisdom-filled conversations—and make multiple six-figures!

Business Model
Skills Required
Communication & Podcasting
Profit Potential

Words of Wisdom

I asked Kathleen how to build a brand and get more podcast listeners. She said to focus on making “real” content, having real conversations. And show up with consistency. They haven’t missed a week of recording in over three years.

Although they got sponsorship early, Kathleen’s advice is to not worry about it. It’s rare to make a good income entirely from sponsorships. If you do get sponsored, make sure your values and expectations are aligned. And think outside of the box on what that partnership looks like.

Fun Fact

Kathleen and Emily's lucky break was when Freshbooks Cloud Accounting wanted to partner with them right out of the gate. These days, they have become more than a sponsor and have collaborated with them by buying their bosses beers at a local (to their HQ) brewery in Toronto, a party on a yacht in Miami, and a parade through the streets of New Orleans at their annual Being Boss Vacations. These vacations are how they celebrate their successes—not only with each other but their community of listeners.

Notes from Chris

Episode 404
Kathleen Shannon and Emily Thompson were creative colleagues. Kathleen co-founded a branding agency in 2011, and Emily’s studio has been developing websites for almost a decade. They collaborated on some projects and struck up a friendship. Then they started meeting monthly for Skype calls. They would share what was and wasn’t working in their businesses and exchange ideas to take their businesses to the next level.

In November of 2014, Emily pitched the idea of turning those conversations into a podcast called Being Boss Podcast. They knew their conversations were similar to what a lot of other creatives were having. Less than three months later, in January of 2015, they released their first episode.

They had no plans to monetize this podcast. If anything, they hoped it would be an awareness tactic for Kathleen’s branding agency and Emily’s website development studio. However, soon after that first episode, they were featured in the "new and noteworthy" section of iTunes." They also made it up to number two in the Business category!

They kept their expenses low by not using expensive equipment and doing most of the production themselves using GarageBand. As their revenue increased, they began to hire or outsource parts of the process. They invested in a sound engineer, a content director, and a virtual assistant, among others.

Speaking of revenue, after making a bit over one-hundred-thousand dollars in their first year, they made $250,000 dollars in 2016. And last year, they made over $400,000 dollars.


  • Being Boss Podcast: Check out these awesome ladies and their super informative podcast over on their website!
  • Freshbooks: The accounting software company that ended up being Being Boss' first official partner and helped them really get started
  • GarageBand: The digital audio workstation that allowed Kathleen and Emily to create their podcast and keep their expenses low

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
"You don't need fancy equipment, you don't need to be the most popular person in the room, and you don't have to have it all figured out. You just have to show up, do the work, and do your best every single day."
—Kathleen Shannon & Emily Thompson #SideHustleSchool

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To infinity and beyond,

Chris Guillebeau