Today, I have the pleasure of sitting down with Courtney Kelly, founder of Courting - a tennis-inspired brand rooted in nostalgia, community, and seriously good style. What started as an idea for a tennis themed coffee shop (and even a matchmaking app) evolved into a full collection that blends performance, functionality, and fashion in the coolest way. We talk about the real story behind Courting - from growing up around tennis in the 90s to reimagining what the sport looks and feels like today. Courtney shares what it actually takes to build a brand from the ground up: trademarking your idea, pushing through endless design iterations, and learning when to trust your instincts. We also get into starting something new later in your career, navigating stability vs. risk, and letting go of the idea that there's a "right" timeline for success. Plus, a behind the scenes look at what it's been like working together on the collection, and why tension, honestly, and creative trust are the magic ingredients. Courting is about more than just tennis fashion, it's about community, self-expression, and doing something because you genuinely love it.

This episode is brought to you by Alice + Olivia, Sam Edelman, and Jones Road Beauty.

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This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

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Today we are revisiting a powerful conversation from the With Whit archives with holistic psychiatrist Dr. Ellen Vora that still deeply resonates. In it, Dr. Vora unpacks the difference between "true" and "false" anxiety and how our bodies often hold the clues to what we're feeling. We get into how physical imbalances like sleep, hormones, and blood sugar can affect our mental health, and how learning to listen to our bodies can help us respond with more clarity and compassion. With so many of us navigating stress and uncertainty, this conversation feels more relevant than ever- and the perfect time to revisit.

This episode is brought to you by HERS and Sam Edelman.

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This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

Produced by Dear Media

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Hello hello, we are here. We are swamped with things, crazed, and late on our episode, but we are here and doing the best we can. What's been going on with us? We get into all of it. Plus, our thoughts on what we've been watching - Love Story, more weekly Timothee Chalamet commentary, debating whether or not we want to go to the Elton John Oscars After Party, the goodness of French onion soup, and lots more from the Port-Rosenman Kitchen Table Chronicles. PS. Timmy has 24 Hours to let me know if you want to come to the Elton John After Party with me. Thank you for being here with us!

This episode is brought to you by HERS and Sam Edelman.

• It’s time you get the support that actually reflects your needs. Start your free intake at ForHers.com
• Time to refresh for spring, visit samedelman.com to explore everything you need for spring and get 15% off with code WITHWHIT15

This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

Produced by Dear Media

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week felt heavy, not catastrophic, not dramatic, just layered. I'm sharing about our recent surrogate embryo transfer and finding out it didn't take. Even when you know the statistics, hope quietly builds a future in the back of your mind, and each time that future dissolves, the grief is real. I talk about what it feels like to move through disappointment when your life is objectively full and beautiful, and how gratitude and grief can sit side by side without canceling each other out. I also get into the complicated tension of ambition and motherhood. Missing a camping trip with Sonny and Timmy. Launching new projects. Turning 41. Wondering how I want to be remembered - as ambitious, present, steady, joyful? Can you be all of them at once?

This episode is really about capacity and how much we can hold. Absence and abundance. Career momentum and family tenderness. Disappointment and deep gratitude. Maybe adulthood isn't about resolving the contradictions. Maybe it's about becoming spacious enough to carry them.

This episode is brought to you by HERS and The RealReal.

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This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

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Hello hello, it's Date Night! We are in a limbo waiting period with our surrogate, taking things day by day and trying to stay grounded in this very lovely LA sunshine. Timmy is gearing up for a solo El Cap camping trip with Sonny and an entire grade's worth of kids and parents...so unpacking a little anxiety there. We talk about our mini credit card audit, spiraling about subscriptiong "scams", and debating money mindsets. From there, it's the usual wander: skincare routines, planking goals, New York food disappointments, and all the things the internet is obsessing over - Carolyn & JFK Jr, Summer House, AI Vegetable videos that yell at you. Come hang.

This episode is brought to you by HERS and The RealReal

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This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

Produced by Dear Media

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In celebration of The High Confectionary's new chocolate bar launch (!!), I'm sitting down with Sarah Fennel, founder of Broma Bakery and the baker extraordinaire who helped bring our new chocolate bars to life! Sarah is behind some of the internet's most beloved dessert recipes, but this conversation goes way beyond baking. She opens up about her complicated relationship with food growing up, how control and anxiety showed up for her as a teenager, and what recovery has actually looked like over time: not a neat "before and after", but as something layered and ongoing. She shares so openly about disordered eating, family instability, and how baking became not just a creative outlet, but a way back to joy. We get into the origin story of Broma Bakery, the food memories that shape us, and how she built a full career around dessert (and without cutting corners or stripping the pleasure out of it.) And of course, we talk about cannabis - evolving past party culture, using it intentionally, and discovering it as a tool to feel lighter, gigglier, more present, and more yourself. Plus, the BTS of creating The High Confectionary's new chocolate bars, the flavor development process, and why precise dosing changes everything - especially for women who want to enjoy without going overboard.

This conversation is funny, honest, and joyful, a reminder that dessert and cannabis, at their best, are both about enjoyment, connection, and letting yourself feel good. We love you Sarah!

Link to The High Confectionary's new chocolate bars: https://thehighconfectionary.com/collections/chocolate

This episode is brought to you by Amazon Pharmacy. Amazon Pharmacy is a full service digital pharmacy that delivers prescription medications directly to customers’ homes. Visit pharmacy.amazon.com to learn more.

This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

Produced by Dear Media

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week is a little bit of everything. From family moments and Grammy's fashion to beauty treatments, big feelings, and a rapid-fire dive into everything that's been on my mind lately. I'm sharing a real check-in after an emotional day, how I let myself feel it without spiraling and letting it consume the whole week, and why giving yourself space to process matters more than pushing through. I get into life updates, surrogate updates, tiny joys, motherhood moments, style and beauty obsessions, travel thoughts, Valentine's Day musings, and the questions I'm asking myself as I move into a hopeful, busy new chapter. It's candid, all over the board, and very much how my brain is feeling these days. Thanks for being here with me!

This episode is brought to you by Amazon Pharmacy. Amazon Pharmacy is a full service digital pharmacy that delivers prescription medications directly to customers’ homes. Visit pharmacy.amazon.com to learn more.

This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

Produced by Dear Media

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

After a loud, full, and surprisingly joyful work trip to New York, I'm unpacking what it actually means to feel aligned, even when calendars and to-do lists feel overwhelming. From building things I genuinely love, to unlearning rigid ideas about productivity, to navigating parenthood, partnership, creative work, and big to small life moments, this episode is a good ol' rambling check-in. A reminder that not all work looks neat, not all interests need a plan, and sometimes the best things come from simply following what feels fun.

This episode is brought to you by Amazon Pharmacy. Amazon Pharmacy is a full service digital pharmacy that delivers prescription medications directly to customers’ homes. Visit pharmacy.amazon.com to learn more.

This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

Produced by Dear Media

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.