Kathleen Shannon (@AndKathleen) is a graphic designer and brand strategist, and co-founder of Being Boss, a podcast and community for creative entrepreneurs. Kathleen began as a staff art director, but learned entrepreneurial habits working on her side projects and blogging. She’s now seeking to become a media mogul and serve the creative community.

In this conversation, we discuss the origins of Being Boss, how Kathleen learned systematic behaviour and stays organised, and the common mindsets of creative entrepreneurs.

Catch up with Kathleen on the Being Boss website or that of her agency, Braid Creative.

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Show Notes & Links

  • Prescott had a classmate named Kathleen, who went by Kate. Her mother, also Kathleen, went by Cassie.
  • Kathleen was almost named “Cinco”, born May 5
  • Prescott is born May 6, making the two both Tauruses
  • Kathleen describes herself as a “truth seeker & dream (job) chaser. Tea drinker & good food eater. Risk taker, magic maker & booty shaker.”
  • AndKathleen.com, Kathleen’s personal site and retired blog
  • “Creative Horcruxes”, websites and projects where we divide our passions, time, and attention
  • Kathleen co-owns Braid Creative with her sister Tara
  • Braid Creative is “Branding and business visioning agency for creative entrepreneurs”
  • The Being Boss podcast started in 2014 as a way for Kathleen to “grow the top of her funnel”
  • Emily Thompson (@EmilyM_Thompson), Kathleen’s partner in Being Boss
  • Prescott kept hearing about “your audience”, which sparked him to start The Busy Creator
  • Prescott admits that Being Boss is “ahead” of The Busy Creator in terms of spawning multiple forms (books, events, community classes, etc.)

“Show notes are a great way to increase search engine optimization.”

—Kathleen Shannon

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  • The aim is transform Being Boss from a podcast into “multimedia conglomerate”
  • Chelsea Handler, Kathleen’s hero for hosting a tv show
  • Kathleen & Emily recently submitted a book for publishing (due out Spring 2018)
  • FreshBooks was a sponsor of Being Boss almost since the beginning, because they align
  • Being Boss Facebook Group, 17,000+ members strong, has grown almost beyond control

“How you feel at work affects how you feel at home, and vice versa.”

—Kathleen Shannon

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“We didn't want to sully the waters with money.”

—Kathleen Shannon

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“First, you have to be dedicated to your craft.”

—Kathleen Shannon

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  • 10,000 hours
  • “Fit of Entrepreneurial Passion”, as described by Michael Gerber

“Nothing kills creativity like desperation.”

—Kathleen Shannon

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“You can only connect the dots looking backwards.”

—Steve Jobs

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“I didn't know this thing would need its own bank account one day!”

—Kathleen Shannon

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  • 7 People are involved with the production of Being Boss, including an editorial assistant and an audio editor
  • The E-Myth Revisited by Michael Gerber on Amazon and on Audible
    The E-Myth Revisited by Michael Gerber

“Most people are still in their struggle. There's never a 'there'.”

—Kathleen Shannon

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“Your goals mean shit if you feel like shit along the way.”

—Kathleen Shannon

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  • Ask your audience what they want, to create new content
  • Put in your 10,000 hours before becoming an entrepreneur; become a “confident expert”
  • Build a bridge before leaving your full-time job
  • Aim to replace your income before taking that last leap
  • Ask to be in client meetings; see the process up close
  • Share your process as you’re in it — publish along the way
  • Codify your methods, translate them to an e-course
  • Find a “business bestie” and have “Skype dates”
  • Use your existing resources to bolster your side projects
  • Create an org. chart to plan future expansion, duties
  • Know every element of your business, and only outsource as needed
  • When overwhelmed, write top 3 items on a Post-It
  • Be a little more casual with your team when chatting on Slack


  • Drink Coffee and Tea every morning
  • Broadcast on Facebook Live a few times a week
  • Make decisions, whether they’re right or wrong
  • Respect your future self (through systems)
  • Have empathy for others and what they struggle with — it may be different from you
  • Put everything in Google Calendar
  • Work out first thing in the morning

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About the author: Prescott Perez-Fox

Prescott Perez-Fox is a New York-based graphic designer and brand developer with 17+ years experience in branding, packaging, graphic design, and web design. He runs The Busy Creator.

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