From Broke to Brilliant: John's Story episode artwork

EPISODE · Oct 2, 2025 · 1H 6M

From Broke to Brilliant: John's Story

from A Rainbow In The Storm · host Katharine & Seth Sullivan-Dawes

This week Seth and Katharine welcome the iconic John Sullivan - CPA, tax attorney, town planner and developer, real estate lover, and the bravest entrepreneur we know. John shares with us the first 100-120 of Winthrop, the walkable town he and his wife have been creating and building for over 25 years. With every odd seemingly against them, John tells the story of how they overcame each and every obstacle that was thrown their way and by the grace of God were able to navigate this seemingly unsolvable maze. From having money to having no money, heart-attacks, sudden deaths, and literally no path to follow, John shares his story and the insights he’s learned about life and business. We hope you truly enjoy this episode and please if you do, consider subscribing or leaving us a written review on Apple Podcasts. Thanks so much and see you all next Thursday! John Sullivan’s very unofficial bio: Originally from Brockton, Massachusetts, and the youngest of seven, John was dragged to St. Petersburg, Florida when his parents retired and couldn't wait for him to finish his high school years. Luckily he ended up in the same high school as Kay Beckett, who would become Kay Sullivan - a woman who for various and unknown reasons continues to be married to him 45 years and counting. John started his first business at 15 by renting sound equipment that he didn't own out to local musicians in an enterprise that turned out to be quite successful. His second business as a concert promoter did not turn out so well, but that's a story for another day. John is a CPA and tax lawyer by trade but when he and his wife moved to the Greater Brandon area in Florida they saw the problems of suburban sprawl. In an attempt to help, he and his wife accidentally but maybe on purpose stumbled into town planning and building and thus the Traditional Neighborhood Development known as Winthrop was born. He has been working on this nightmare...I mean dream since 2000. He and his wife now live there as well. They have three children, one of whom insists that he be on her super cool podcast.  A few useful links: Winthrop’s Website Jenna Kutcher’s The Podcast Lab Course Katharine’s Writings

This week Seth and Katharine welcome the iconic John Sullivan - CPA, tax attorney, town planner and developer, real estate lover, and the bravest entrepreneur we know. John shares with us the first 100-120 of Winthrop, the walkable town he and his wife have been creating and building for over 25 years. With every odd seemingly against them, John tells the story of how they overcame each and every obstacle that was thrown their way and by the grace of God were able to navigate this seemingly unsolvable maze. From having money to having no money, heart-attacks, sudden deaths, and literally no path to follow, John shares his story and the insights he’s learned about life and business. We hope you truly enjoy this episode and please if you do, consider subscribing or leaving us a written review on Apple Podcasts. Thanks so much and see you all next Thursday! John Sullivan’s very unofficial bio: Originally from Brockton, Massachusetts, and the youngest of seven, John was dragged to St. Petersburg, Florida when his parents retired and couldn't wait for him to finish his high school years. Luckily he ended up in the same high school as Kay Beckett, who would become Kay Sullivan - a woman who for various and unknown reasons continues to be married to him 45 years and counting. John started his first business at 15 by renting sound equipment that he didn't own out to local musicians in an enterprise that turned out to be quite successful. His second business as a concert promoter did not turn out so well, but that's a story for another day. John is a CPA and tax lawyer by trade but when he and his wife moved to the Greater Brandon area in Florida they saw the problems of suburban sprawl. In an attempt to help, he and his wife accidentally but maybe on purpose stumbled into town planning and building and thus the Traditional Neighborhood Development known as Winthrop was born. He has been working on this nightmare...I mean dream since 2000. He and his wife now live there as well. They have three children, one of whom insists that he be on her super cool podcast.  A few useful links: Winthrop’s Website Jenna Kutcher’s The Podcast Lab Course Katharine’s Writings

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From Broke to Brilliant: John's Story

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This episode was published on October 2, 2025.

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This week Seth and Katharine welcome the iconic John Sullivan - CPA, tax attorney, town planner and developer, real estate lover, and the bravest entrepreneur we know. John shares with us the first 100-120 of Winthrop, the walkable town he and his...

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