Cupcakes & Comebacks w/ Damala Badon
Tue Feb 03 2026
What does it take to build a dessert empire while navigating the hardest trials life can throw at you? Host Leigh LaRie is joined by the "Cupcake Queen" herself, Damala Badon, owner of DB Dessert Company. In this moving and transparent episode, "Cupcakes & Comebacks," Damala shares her journey from self-taught home baker to a powerhouse entrepreneur with multiple locations in Portland.
Damala opens up about the "thug thistle" of the hustle—from expanding to three stores and dealing with vandalism to the difficult decision to consolidate for the sake of her family. The conversation takes a deep dive into the reality of Black motherhood and entrepreneurship, as Damala discusses the tragic loss of her oldest son and how she continues to move forward for her two living children.
From the "cracker pie" that inspired her grandmother to the technical challenges of shipping cupcakes in jars, Damala embodies resilience. They discuss the myth that women can't raise men, the importance of therapy, and navigating a public divorce while maintaining your grace. This is a story of legacy, survival, and the sweet taste of a well-earned comeback.
Episode Time Breakdown:
[00:00] Intro: Welcome to Season 7, Episode 8
[01:05] Meet Damala Badon: The myth, the legend, and the Cupcake Queen
[01:59] The Beginning: How a 2-year-old’s birthday cake sparked a 16-year career
[03:49] Legacy over Bills: Why Damala chose the path of a brick-and-mortar business
[05:25] The Expansion Journey: From Gleason and Alberta to consolidating back to one
[06:55] Trust and NDAs: How to build a team without losing your secret sauce
[08:46] Finding the Niche: Transitioning from custom 3D cakes to high-volume cupcakes
[10:44] Business Fails: The story of the "lost cake" and how to apologize like a boss
[12:54] Favorite Designs: Letting her sons test her skill set with Minions and basketball courts
[14:44] Representation in Portland: The heavy weight of being a Black woman in business
[16:03] Inspiration: Cracker Pie and the "Apple Pie" survival mode of the 1930s
[18:19] Mentoring the Youth: Giving young people their first jobs and operational support
[19:32] Community Service: Supporting the community through SNAP benefit cuts with free bread
[21:00] Cupcakes in a Jar: The trial and error of shipping logistics
[23:12] The Snowstorm Rebuild: Coming back after a collapsed ceiling and a flooded bakery
[25:15] Navigating Grief: Moving forward after the tragic loss of her son
[28:08] Self Care & Therapy: Leaning on a core group of friends and professional support
[30:50] Parenting Black Men: Autonomy, natural consequences, and the myth of the single mom
[36:46] Public Figures & Private Divorces: Staying silent when "hurt people hurt people"
[41:00] Choosing Yourself: Why staying "for the kids" isn't always the best decision
[45:51] Reintroducing Yourself: Finding peace in the quiet moments of the "soft life"
[48:43] The Dating Scene: Introverted dating and avoiding the "piss in the pool"
[51:19] Leigh’s...
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What does it take to build a dessert empire while navigating the hardest trials life can throw at you? Host Leigh LaRie is joined by the "Cupcake Queen" herself, Damala Badon, owner of DB Dessert Company. In this moving and transparent episode, "Cupcakes & Comebacks," Damala shares her journey from self-taught home baker to a powerhouse entrepreneur with multiple locations in Portland. Damala opens up about the "thug thistle" of the hustle—from expanding to three stores and dealing with vandalism to the difficult decision to consolidate for the sake of her family. The conversation takes a deep dive into the reality of Black motherhood and entrepreneurship, as Damala discusses the tragic loss of her oldest son and how she continues to move forward for her two living children. From the "cracker pie" that inspired her grandmother to the technical challenges of shipping cupcakes in jars, Damala embodies resilience. They discuss the myth that women can't raise men, the importance of therapy, and navigating a public divorce while maintaining your grace. This is a story of legacy, survival, and the sweet taste of a well-earned comeback. Episode Time Breakdown: [00:00] Intro: Welcome to Season 7, Episode 8 [01:05] Meet Damala Badon: The myth, the legend, and the Cupcake Queen [01:59] The Beginning: How a 2-year-old’s birthday cake sparked a 16-year career [03:49] Legacy over Bills: Why Damala chose the path of a brick-and-mortar business [05:25] The Expansion Journey: From Gleason and Alberta to consolidating back to one [06:55] Trust and NDAs: How to build a team without losing your secret sauce [08:46] Finding the Niche: Transitioning from custom 3D cakes to high-volume cupcakes [10:44] Business Fails: The story of the "lost cake" and how to apologize like a boss [12:54] Favorite Designs: Letting her sons test her skill set with Minions and basketball courts [14:44] Representation in Portland: The heavy weight of being a Black woman in business [16:03] Inspiration: Cracker Pie and the "Apple Pie" survival mode of the 1930s [18:19] Mentoring the Youth: Giving young people their first jobs and operational support [19:32] Community Service: Supporting the community through SNAP benefit cuts with free bread [21:00] Cupcakes in a Jar: The trial and error of shipping logistics [23:12] The Snowstorm Rebuild: Coming back after a collapsed ceiling and a flooded bakery [25:15] Navigating Grief: Moving forward after the tragic loss of her son [28:08] Self Care & Therapy: Leaning on a core group of friends and professional support [30:50] Parenting Black Men: Autonomy, natural consequences, and the myth of the single mom [36:46] Public Figures & Private Divorces: Staying silent when "hurt people hurt people" [41:00] Choosing Yourself: Why staying "for the kids" isn't always the best decision [45:51] Reintroducing Yourself: Finding peace in the quiet moments of the "soft life" [48:43] The Dating Scene: Introverted dating and avoiding the "piss in the pool" [51:19] Leigh’s...