Play It Brave Podcast

Play It Brave Podcast

The podcast for brave creatives who live in a world that wants you to play it safe. It's time to face facts: You are an indestructible woman fused with super powers that defy convention. Am I right? If so, then this podcast is for you! In Play It Brave, D'Arcy Benincosa dives in deep to her wit and wisdom to teach you about creative a life full of mindset, money, and marketing miracles! Let's get started!

Episodes

January 8, 2026 50 mins

This week on the Play It Brave podcast, I'm doing something a little different — I'm bringing you behind the scenes for a real coaching session with one of my favorite photographers (and one of my trusted second shooters), Jasmine Ortiz.

This episode is for every photographer who has ever thought:

"I know my work is good… so why do I get weird and wobbly the second it's time to talk about pric...

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Welcome to the final episode of 2025 — the year of the snake, the year of shedding skins that no longer fit. If this year felt like a raw unraveling, a call to deeper truth, a refusal from the Universe to let you live inside half-truths or "good enough," this episode is for you.

As has become tradition, I invited one of my wisest, most grounded friends — Casey — to interview me about my year. She's someone...

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In today's episode, I'm talking with my friend Dawn Weisberg of Tularosa Flowers about what it actually takes to create and book large-scale luxury weddings — not just from a "pretty" standpoint, but from a strategic, energetic, and logistical one.

Dawn and I both came to the wedding industry later in life with long creative careers behind us — mine in directing and acting, hers in costume design for film ...

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On today's episode of Play It Brave, I'm bringing you behind the scenes for Part Two of my coaching call with photographer Staci Addison.

In Part One, we focused on nervous system safety, trauma, and getting her out of chronic fight-or-flight so she could actually show up for her business.

In t...

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Today I'm sharing something different: a real coaching call with my client, Staci Addison. Instead of jumping straight into marketing, we start where sustainable growth actually begins—helping your nervous system feel safe after grief, burnout, and a long, hard season. Most creatives don't get stuck because they lack strategy; they get stuck because fear, people-pleasing, perfectionism, and old money stories keep their...

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Today I'm joined by my brilliant friend, fashion-and-wedding photographer Sandra Åberg, for a real talk we've both been having off-mic for years: does being "published" (Vogue, Harper's, Martha) actually mean you've arrived—or is it another industry illusion that keeps creatives chasing validation? We swap origin stories (Milan fashion sets, Sports Illustrated mayhem, and stumbling into weddings), talk integrity lines,...

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If you've ever paused on your next chapter because you think you need to be "more ready" or "more perfect," this one's for you. My dear friend, multi-hyphenate creative and mentor Jessica Eileen Drogosz joins me to dismantle the myth that leaders must have it all together before they lead. From building associate teams and separating brands to launching a heart-led coaching offer, Jessica shares the real (and often mes...

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I almost never say yes to cold pitches. But one late night, I opened an email from Meghan Ely of OFD Consulting—and instead of deleting it, I hit reply. It was researched, personal, and actually useful. That same energy comes through in this conversation, where Meghan shares how she's helped creatives land features in The New York Times, Brides, Martha Stewart, People, and more.

This episode will shift how...

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Have you ever built something that looked incredible from the outside…but didn't actually feel good to live in? I've been there, and so have today's guests, Brad & Jen.

Brad & Jen are a husband-and-wife photography duo with over a decade of experience behind the camera and in business. When I first came across their words on Instagram, I was struck by how different their perspective was from the usual "gro...

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On today's episode of Play It Brave, I'm joined by my dear friend, the incredible creative and leader, Carrie Moe.

Carrie is someone I deeply admire—not only because of her talent (she's styled for brands like Ritz-Carlton, Fujifilm, and Berta Bridal, and been featured in Martha Stewart Weddings, The Knot, and Brides), but because of the way she approaches her work with confidence, creativity, and so much ...

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In this episode, I had the absolute pleasure of sitting down with the incredible Marion Roach Smith—author, memoir coach, and one of the most no-nonsense, truth-telling voices in the writing world.

We talked all about memoir writing—what it is, what it isn't, and why it's one of the most powerful tools for making sense of your life and sharing your story with the world. Marion shares how her background in ...

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Today on the Play It Brave podcast, I'm joined by the ever-inspiring Natasha Sewell—a photographer, educator, and expert in creating heartfelt client experiences. Natasha started her photography business at 41, and if you've ever thought you were "too late" to pivot or start something new, you need to hear this story.

We talk about making bold moves at any age—whether you're transitioning from studio to li...

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This week, the brilliant Dr. Chelsea Shields and I continue the conversation about something that's at the heart of every powerful brand and every transformational leader: authenticity.

We go deep into what it means to show up fully as yourself in your brand, your business, and your life. From emotional intelligence to the way you use your voice and body to commu...

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In this episode, I sit down with Dr. Chelsea Shields—anthropologist, speaker trainer, and communication expert—to dive deep into the heart of what makes a brand truly resonate in today's world: authenticity.

We unpack why authenticity is more than a buzzword—it's your most valuable currency as a personal brand. Whether you're an entrepreneur, creative, or thought leader, this conversation will help you und...

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Ever wondered what it really takes to become a second shooter that lead photographers rave about—or how to find one you can trust with your name, brand, and reputation?

In this candid and wisdom-packed episode, I sit down with award-winning photographer and my own second shooter, Jasmine Ortiz, to dive deep into the art, etiquette, and energy of second shooting in the luxury wedding world.

Wit...

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What if midlife wasn't a crisis—but a chrysalis?

In this powerful and heartfelt conversation, D'Arcy sits down with spiritual leader and transformational guide Dr. Devaa Haley Mitchell to reframe the way we view this pivotal life stage. Together, they unpack the idea of midlife as a sacred period of unraveling, reclaiming, and radiating—a time of deep transformation that prepares us to emerge more fully ex...

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In this episode, D'Arcy and her sister April dive deep into what it means to reclaim love on your own terms—especially when you've spent years minimizing your needs, hiding your pain, or staying small to feel safe. Together, they explore how worthiness, visibility, and nervous system regulation play a role in opening yourself back up to being loved, seen, and supported.

They reflect on how generational and...

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Most luxury planners don't work with just anyone—and if you've ever tried to get on their radar, you know how tough it can feel.

In this episode, I pull back the curtain on what actually builds trust with high-end planners, how to navigate the "Catch-22" of not having luxury work yet, and how to start making meaningful connections with planners who are aligned with where you are now.

Plus, I s...

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In this soul-nourishing episode, D'Arcy welcomes back her sister Brooke Benincosa to share the sacred story of how they co-steward Nightingale Cabin—a healing sanctuary tucked into the Utah mountains—and the vision they're bringing to life through retreats, land rituals, and community gatherings.

Together, they explore what it means to live in deep connection with nature, rhythm, and each other. Brooke sha...

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In this episode, we sit down with Maria Ortiz—a talented photographer who has transformed her senior portrait business by infusing it with deep emotional connection, thoughtful communication, and bold pricing strategies.

Maria shares how she brings excitement and warmth into every stage of her client process, from the first email to the session day. She discusses how her carefully crafted questionnaire hel...

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