Sugar Mommy™ with Kareen Mills

About Sugar Mommy™ with Kareen Mills

Welcome to The Sugar Mommy™ Podcast with Kareen Mills. This is the show for powerhouse women in midlife who know their wisdom is their wealth. Here, we redefine what it means to be a Sugar Mommy™ — a financially independent woman who leads with experience, builds bankable businesses, and creates impact on her own terms. This isn't hustle culture. This is strategy, clarity, and leverage. With former Bank VP turned serial entrepreneur and media founder this podcast is where money gets honest, visibility becomes an asset, and hard-earned wisdom transforms into real income. No fluff. No noise. Just smart conversations, grounded leadership, and bold moves that actually work.

Publisher

Kareen Mills

Category

business · business

Language

en

Explicit

No

First episode

6 Feb 2026

Latest episode

10 Nov 2026

Latest episodes

36 episodes in the feed.

1. 

   10 Nov 2026

   How Isle of Monday Is Making Luxury Vintage Fashion Accessible with Gabriella Carota and Janelle Gray-Gilbert

   What if you could rent the exact vintage dress a celebrity just wore? In this episode, I sit down with Gabriella Carota and Janelle Gray-Gilbert, co-founders of Isle of Monday, the first rental platform for luxury vintage and archival fashion. As one of their investors, I wanted you to hear how two vintage resellers turned one customer request, "can I rent that?", into a platform making rare, collectible fashion accessible to everyone. Gabriella and Janelle break down how vintage fashion rental works, from bringing a fragmented, Instagram-run industry online to a consignment model that gives collectors completely passive income while their pieces keep growing in value. They also share why they built a 30,000-person waitlist before launch, how they make one-of-one vintage feel seamless with fit tools, real customer photos, and in-house repairs, and what it means to wear the exact piece Millie Bobby Brown wore. We also talk about why Gen Z is choosing vintage over fast fashion, why unsigned pieces are their own kind of luxury, and how celebrity stylists and everyday fashion lovers created a marketing flywheel that has taken Isle of Monday this far with $0 spent on marketing. If you love fashion, want to build a business with real demand behind it, or are curious where luxury is headed next, this episode is for you. Tune in to this episode of Sugar Mommy podcast: How Isle of Monday Is Making Luxury Vintage Fashion Accessible. I'm Kareen Mills. I watched my mother struggle as an entrepreneur, so I made it my life's mission to help women and entrepreneurs just like her. I thought becoming a Bank VP was the answer, only to discover my mother's story was repeating in brilliant, hardworking, ambitious women. As a former Bank VP, I now use my insider knowledge in finance and business to help women become bankable, visible, and unforgettable. Instagram: https://www.instagram.com/kareenmills/ Facebook: https://www.facebook.com/kareenmills/ LinkedIn: https://www.linkedin.com/in/kareenmills/ Website: https://kareenmills.com/ THE BIGGEST FRIENDSGIVING LIVE® EVENT here: https://friendsgivinglive.com/ Gabriella Carota is the Co-Founder and CEO of Isle of Monday, the first rental platform for luxury vintage and archival fashion. A former model, EY consultant, and Boston University business graduate, she started Isle of Monday as a vintage resale business in 2021, building a loyal following at the Brooklyn Flea and Canal Street Market. Today, she leads sourcing, garment care, and merchandising, turning her talent for finding rare pieces into a platform that makes fashion history accessible to everyone. Instagram: https://www.instagram.com/carotawithlime/ LinkedIn: https://www.linkedin.com/in/gabriella-carota-895828159/ Janelle Gray-Gilbert is the Co-Founder of Isle of Monday, where she leads marketing and growth. With corporate experience that includes Net-A-Porter, she left her corporate role to build what she believed was the next big thing in fashion tech. She helped grow a 30,000+ waitlist before launch and a celebrity-powered marketing flywheel that has scaled Isle of Monday with $0 spent on marketing. Together with Gabriella, she was named to Create & Cultivate's 2026 CC100 list. Instagram: https://www.instagram.com/janellelgray/ LinkedIn: https://www.linkedin.com/in/janellegray/ Isle of Monday Website: https://isleofmonday.com/ Instagram: https://www.instagram.com/isleofmonday/ TikTok: https://www.tiktok.com/@isleofmonday Substack: https://isleofmonday.substack.com/ Consign With Isle of Monday: https://isleofmonday.com/pages/consign-with-us Book a NYC Showroom Appointment: https://isleofmonday.com/pages/showroom-appointment

2. 

   20 Oct 2026

   Could the AI Revolution Actually Be Creating a Human Revolution?

   What if being human is becoming our competitive advantage in a world full of AI? In this episode, I talk about how I use AI every single day, from my AI CEO to my AI calorie deficit tracker, and why it's actually giving me more capacity to be more human. If your AI isn't doing that for you, you might be using it the wrong way. I share the contradiction nobody is talking about. The easier it becomes to manufacture content, the more valuable the things that are hard to manufacture become, and that's you. Your stories, opinions, relationships, and lived experience can't be mass produced. I call it the who revolution, the revolution happening inside the AI revolution. I also open up about an AI bully who left a nasty comment on one of my posts and what it reminded me about the side of human behavior I'm not a fan of. From there, I explain why we only remember one or two businesses out of ten that say the same thing, and what "be human first, give the rest to AI" looks like in practice. I break down what to keep human, what to hand over to AI, and how I use automations and personal voice notes in my Instagram DMs to build real human to human connection. If you've ever worried that AI is making you disappear, this episode will help you use technology for leverage without automating away the very thing that makes people want to know you, remember you, trust you, and do business with you. Tune in to this episode of Sugar Mommy podcast: Could the AI Revolution Actually Be Creating a Human Revolution? I'm Kareen Mills. I watched my mother struggle as an entrepreneur, so I made it my life's mission to help women and entrepreneurs just like her. I thought becoming a Bank VP was the answer, only to discover my mother's story was repeating in brilliant, hardworking, ambitious women. As a former Bank VP, I now use my insider knowledge in finance and business to help women become bankable, visible, and unforgettable. Instagram: https://www.instagram.com/kareenmills/ Facebook: https://www.facebook.com/kareenmills/ LinkedIn: https://www.linkedin.com/in/kareenmills/ Website: https://kareenmills.com/ THE BIGGEST FRIENDSGIVING LIVE® EVENT here: https://friendsgivinglive.com/

3. 

   13 Oct 2026

   What If We Stop Treating Every Connection Like the Beginning of a Funnel?

   What if the way we've been taught to network online is costing us the very thing that builds a business? In this episode, I talk about what happens when we treat every new connection like the top of a funnel and why leading with our business makes us lose touch with human connection. I share the story of a CPA who dropped a tax strategy pitch in my LinkedIn DMs the moment I accepted his connection request. Instead of ignoring it, I tested something I learned at a conference called the non-pitchy pitch. I shared my immigration journey and who I am, not what I do, then handed the floor back to him. He mirrored it, opened up about his family and their spicy food competitions, and admitted he'd lost touch with human connection because of how things are being taught online. From there, I explain why connection before transaction doesn't mean being anti-sales. I'm the biggest promoter on the planet, but I believe business comes as a byproduct of real relationships. I talk about why some of the best roles I've ever landed came from connecting, not selling, why your humanity is what sets you apart in a crowded market, and why you should never predetermine relationships or see people as dots on your sales chart. I also share a story about covering a stranger's rent and why the best way to give is to someone who can never pay you back. If you've ever felt like just a number, or caught yourself wondering where someone fits in your funnel, this episode will help you ask better questions, put humans back in front of business, and become unforgettable. Tune in to this episode of Sugar Mommy podcast: What If We Stop Treating Every Connection Like the Beginning of a Funnel? I'm Kareen Mills. I watched my mother struggle as an entrepreneur, so I made it my life's mission to help women and entrepreneurs just like her. I thought becoming a Bank VP was the answer, only to discover my mother's story was repeating in brilliant, hardworking, ambitious women. As a former Bank VP, I now use my insider knowledge in finance and business to help women become bankable, visible, and unforgettable. Instagram: https://www.instagram.com/kareenmills/ Facebook: https://www.facebook.com/kareenmills/ LinkedIn: https://www.linkedin.com/in/kareenmills/ Website: https://kareenmills.com/ THE BIGGEST FRIENDSGIVING LIVE® EVENT here: https://friendsgivinglive.com/

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Apple Podcasts (US)

5.0 / 5

3 ratings

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