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Cup of Ambition Podcast

By Bonnie Bryant O'Connor

We’re committed to having smart, honest, funny, no B.S. conversations with real-life boss bitches from the entrepreneurial, corporate, and nonprofit worlds.

  1. 1.
    A Color-Obsessed Abstract Artist Busts the Myth of the "Starving Artist" (and Shares Her Inspirational Mental Health Journey)10/11/2019
  2. 2.
    The Queen of Modern Calligraphy Tells Us How She Was Able to Quit her 9-5 Job to Hand-Letter Full Time (and How ANYONE Can Learn How to Do Calligraphy)10/04/2019
  3. 3.
    A Therapist & Life Coach Tells Us How Millennial Women Can Deal with Their Work Stress (and Why It’s Such an Issue for Them)09/28/2019
  4. 4.
    A Brand Photographer Tells Us How to Make Your Brand Stand Out When There’s So Much Content on the Web (and How to Have the Best Brand Photoshoot Ever)09/14/2019
  5. 5.
    A CPA and Business Coach Tells Us How to Actually Create a Profitable Business (and the Biggest Mistakes She Sees Business Owners Make)09/07/2019
  6. 6.
    A Former Cop and Real Estate Expert Tells Us How to Create Sustainable Passive Income with Rental Properties (and Why Quitting His Stable 9-5 Job and Giving Up His Pension Was the Best Thing He’s Ever Done)09/06/2019
  7. 7.
    A PR and Business Development Expert Talks About How to Promote Your Business Effectively (and How Once You Know Business Fundamentals, You Can Launch ANY Business)09/02/2019
  8. 8.
    A Social Media Expert Shares an Inside Look Into Digital Marketing (and the Benefit of Having a Zillion Different Jobs in Your Twenties)08/26/2019
  1. 9.
    An Artist, Painter, and Former Calligrapher Talks About How to Successfully Pivot Your Business (and Why Taking Care of Your Mental Health is Just as Important as Your Physical Health)08/17/2019
  2. 10.
    A Harvard Law Grad and Entrepreneur Talks About Bringing People Together With Curated Care Packages (and How to Build A Profitable Gift-Based Business)08/09/2019
  3. 11.
    A Music Executive and Songwriter Talks About How to Stand Out in a Competitive Industry (and Why Creatives and Performers Need to Diversify Their Revenue Streams)08/02/2019
  4. 12.
    A Cookie Artist Talks About Taking the Jump from Full Time Office Job to Full Time Cookier (and if She Ever Gets Sick of Eating Cookies)07/26/2019
  5. 13.
    A Professional Voice Actor Talks About the Freelance Life in the Entertainment Industry (and How to Be Successful Despite the Odds)07/19/2019
  6. 14.
    A Paper Florist Talks About the Nitty Gritty of Pretty Florals (and How to Show Your Worth When People Think You’re Just a “Crafter”)07/12/2019
  7. 15.
    A Nonprofit and Grants Expert Talks About Opening Your Business as A Nonprofit (and How You Can Use Grants to Do It)07/05/2019
  8. 16.
    A Live Event Artist Talks About Changing Lives with Her Art (and That Time She Was on “The Celebrity Apprentice,” a Very Long Gilmore Girls Discussion, And the Weirdest Question She’s Gotten on the Job)06/28/2019
  9. 17.
    A Web Developer and Strategist Talks About Learning on the Job (and Lots of Free Advice on How to Improve Your Website)06/21/2019
  10. 18.
    A Designer and Letterpress Printer Talks About the Ups and Downs of the Wedding Industry (and How to Raise Your Prices and Save Your Sanity)06/14/2019
  11. 19.
    A Nonprofit Director, Lobbyist, and Political Activist Talks About Being in the Room Where It Happens (and Leveraging Each Opportunity to Climb the Ladder)06/07/2019
  12. 20.
    A Graphic Designer Talks Getting Her Artwork into Major Stores (and A Lengthy Discussion About 90s Boy Bands)05/30/2019
  13. 21.
    A Career Coach Shows You How to Job Search the Right Way (and How She Went from Choosing Candidates to Showing Them How to Get the Job)05/30/2019
  14. 22.
    What It’s Like to Be a Creative Director (and How to do Influencer Marketing the Right Way)05/30/2019
  15. 23.
    Is This Thing On?! Intro to the Cup of Ambition Podcast05/29/2019

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