Play It Brave Podcast

D'Arcy Benincosa
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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!

  1. 18H AGO

    Why Photographers Aren't Booking Like They Used To — and What To Do About It with Alicia Daw

    On today's episode of the Play It Brave podcast, I'm talking about something many people in the wedding industry are quietly feeling but not always naming out loud. Photographers who used to book 15–20 weddings a year are sitting at just a handful. Retreats are being canceled. Educators who used to sell out instantly are extending deadlines. And behind the scenes, my DMs are filled with the same question: "Is it just me?" So today we're talking about it honestly. I invited my friend Alicia Daw — an experienced luxury wedding photographer who has spent decades in this industry — to join me for a grounded conversation about what's actually happening and how we can respond to it thoughtfully instead of panicking. I don't believe this is just a slow year. I think the industry is going through a correction — post-COVID demand leveling out, economic uncertainty, new buyer behavior, and major technological shifts like AI. The industry isn't ending, but it is changing. And the more clearly we see those changes, the better we can adapt. Key Takeaways This is likely a market correction, not just a slow season. Post-COVID demand, economic uncertainty, and industry saturation are all contributing to the shift. Buyer behavior has changed. Couples compare far more options, hesitate longer, and often communicate less clearly than past clients. Trust matters more than ever. Showing full galleries, simplifying pricing, and clearly communicating your process helps reduce buyer uncertainty. Generic brands struggle in a comparison-heavy market. Clear positioning and personality help you stand out among hundreds of similar photographers. The middle market feels the most pressure. Budget vendors will book, luxury vendors will continue booking, but the mid-range is often the most saturated. Pricing can be both aspirational and strategic. Holding premium dates for high-end bookings while remaining flexible with short-notice opportunities can create stability. Relationships still convert best. Planner relationships, venue partnerships, and referrals often outperform social media algorithms. Multiple revenue streams reduce stress. Diversifying income can provide stability when inquiries fluctuate. After more than 20 years in this industry, Alicia and I have both learned that the wedding world moves in cycles. The key isn't ignoring change, it's responding to it. That means strengthening your positioning, building trust with your clients, nurturing real relationships in the industry, and being willing to adjust your strategy as the market evolves. Challenges like this don't mean the industry is over. They simply mean we're being invited to grow, refine, and approach our businesses with more intention than ever. If you want deeper support in navigating this shift, Alicia shares about her Strategy Retreat in this episode, where she helps wedding professionals align their business strategy with the life they actually want to build. And as always, thank you for being here and for continuing to play it brave in your work and your business. Meet Alicia Alicia Daw is an international, luxury wedding photographer who has spent nearly three decades of her life globetrotting to 45 countries - and counting - while developing an effortless style for capturing exquisite and emotionally charged weddings and events. Featured in prestigious publications like Grace Ormonde, Style Me Pretty, Wezoree, Carats & Cake, and Wedding Chicks, Alicia knows how to attract chic, jet-setting couples and deliver a luxury experience again and again. Within 13 months of starting her photography business, Alicia went from making $10,000 a year as a missionary to over $100,000, consistently booking 5 figure weddings. Less weddings = more money = more life. She is an expert at helping other wedding and portrait industry professionals grow their businesses into something they're proud of by making sense of all the nitty-gritty details so they can pursue life outside of business. She is passionate about finding joy and adventure in the everyday, ordinary moments in her life with the people she loves most. Connect with Alicia Alicia's Website Alicia's Instagram The Strategy Retreat Click here for more ways to listen to this episode.

    42 min

  2. FEB 26

    Is AI Destroying Art or Saving It? with Noella Andres of Imagen

    On this episode of Play It Brave, we're diving into one of the biggest conversations happening in photography right now: AI. The excitement. The skepticism. The "Is this going to replace us?" energy. All of it. I brought on Noella Andres from Imagen AI to talk about what AI in editing actually is (and what it isn't). Noella has spent over 20 years supporting photographers in finding more freedom in their workflows, and her move into Imagen fits perfectly with that mission. Together, we unpack how AI can support your artistry instead of threaten it, how it integrates into Lightroom, how it learns your style, and how to use it consciously — without losing your creative voice. Key Takeaways The real question isn't "Will AI replace photographers?", it's "How can we use AI consciously?" Burnout in photography often comes from hours behind the screen, not from shooting itself. When repetitive tasks are automated, creative energy expands. AI can function like a virtual assistant, handling the grunt work while you stay in artistic control. The danger isn't AI — it's losing your unique voice by relying on formulas (in editing, branding, or marketing). As the world becomes more automated, genuine human connection and client experience become even more valuable. Originality requires intention. Photographers must resist copying trends and instead refine their own artistic identity. Social media fatigue is real. Intentional automations (like email marketing funnels) can create sustainability without constant online presence. Used wisely, AI can actually help you fall back in love with photography by giving you your time and inspiration back. AI isn't the enemy. Burnout is. Blending in is. Giving away your creative voice is. When you let AI handle the repeatable tasks — culling, base edits, workflow — you get your time back for what actually matters: your clients, your craft, and creating because you want to. If you're curious, you can try Imagen through my ambassador link (with 1500 free edits included). And if you have questions, DM me. I want you editing faster, loving your images more, and feeling inspired again. Meet Noella Noella Andres has been in the photography game for over 20 years — Chasing love stories, and eventually finding her real passion: helping other photographers grow wildly successful businesses of their own. These days, she's all about marketing, brand partnerships, and business coaching — guiding photographers as they step into their next big thing, whether that's launching a course, building passive income, or leveling up their visibility. She's part strategy nerd, part hype girl, and fully invested in helping creatives find freedom in their business (and have a little fun doing it). Connect with Noella + Imagen AI Get your 1500 free edits here Noella's Website Noella's Instagram Click here for more ways to listen to this episode.

    35 min

  3. FEB 5

    The Infinite Ways to Photograph a Woman with Elizabeth Messina

    There are episodes that feel like a permission slip… and this one is exactly that. If you've ever thought, "I'm a wedding photographer," or "I'm a family photographer," or you've let a label quietly box you in—this conversation is for you. I'm bringing back my dear friend Elizabeth Messina to the podcast, and every time she's here, I'm reminded why her work has moved people for decades: she doesn't just take photos—she sees women. We talk about what it actually looks like to evolve across genres without losing your signature. How to stay curious even after years in the industry. And why the real "secret" behind her iconic imagery isn't a preset or a pose—it's connection, presence, and trust. Key Takeaways Trust your voice—your point of view matters, even when other styles inspire you. Stay curious forever; learning keeps your work (and you) alive. Sensitivity and empathy aren't "too much"—they're a creative advantage behind the camera. Your brand can be cohesive across genres when your eye is the through-line. Photograph women through seasons of life, not rigid categories like "weddings" or "maternity." Maternity work is powerful because it holds joy, vulnerability, and identity change at once. There are infinite ways to photograph pregnancy—go beyond the standard belly pose. Build trust through connection first; the image comes second. Offer possibility with "What if…?" instead of forcing a concept onto a client. Make the process the win—real connection matters even when you don't get the booking. Know your gear and workflow so the "technical math" doesn't interrupt your creativity. Stay engaged with your own work (even if you outsource) so you keep evolving as an artist. Trust is built in your communication long before the shoot—read what they asked and respond like a human. A sustainable career often comes from evolving alongside your clients over time. This episode is a love letter to the idea that you don't have to be "one thing" to be taken seriously. You can evolve. You can explore. You can shoot weddings and maternity and dark moody work and sun-drenched dreamy work—and still be unmistakably you. Elizabeth's work is proof that your artistry gets stronger the more you stay connected: to your camera, to your subjects, and to your own creative truth. And if you're feeling that tug to expand what you shoot—take this as your sign: you're allowed to grow. Meet Elizabeth Elizabeth Messina is a world renowned, award winning, celebrity photographer. She is a New York Times best selling author & a passionate teacher.. Elizabeth was named "one of the most influential photographers of our decade" by PDN.  Elizabeth has been capturing evocative photographs of women since she picked up a camera at the tender age of 12. Her images are a reflection of her heart. Elizabeth Messina is a visionary, her images tell stories of longing, solitude & the tangible beauty of the human experience. Although Elizabeth's photography takes her all over the world, her home is in Southern California, where she lives with her 3 children & 3 dogs. She continues to be a seeker of beautiful light, strong coffee & meaningful connections. Connect with Elizabeth Elizabeth's Photography Website Elizabeth's Arte of Maternity course The Arte Dept The Art Society Click here for more ways to listen to this episode.

    53 min

  4. JAN 22

    Building a Brand That Attracts the Right Opportunities with Gary & Kim Evans

    On today's episode of the Play It Brave podcast, I'm sitting down with one of my favorite creative power couples in the photography industry, Gary Evans and Kim Evans. We talk about what it really looks like to rebrand with intention, build a cohesive identity, and grow multiple businesses together without losing alignment—or your relationship—in the process. This conversation weaves together the emotional and practical sides of entrepreneurship: branding beyond logos, finding your voice in the education space, building an email list that actually converts, and creating offers like retreats that feel meaningful and expansive. We also dive into collaboration, working as a couple, and why asking for help can completely change the trajectory of your business. What we talk about in this episode: Why branding is foundational, not optional, when building a sustainable business How to create a cohesive identity that actually reflects who you are The role visual identity plays in client trust and perception Finding your unique voice in a crowded education space Using email lists and freebies as powerful (and aligned) growth tools Why retreats can be such a transformative offering for photographers The magic that happens when collaboration is rooted in alignment Working with your partner's strengths instead of against them Prioritizing family and relationships while growing a business Why reaching out for help can fast-track your growth in the best way This episode is a beautiful reminder that success doesn't have to be chaotic or lonely—and that when your brand truly reflects who you are, it can open doors you never even knew to knock on. Meet Gary & Kim Here's our story - we met, despite living in separate countries, by a complete twist of fate that led Gary to help a friend at the same wedding show where Kim had a booth. Gary scoped her out and said she's "right up my street" and 18 months later, after multiple flights, over 50,000 miles, Gary sold his photography company, house, and just about everything else and moved from the UK to Ontario, Canada. We had to completely rebuild his business in Canada, sold our decorating and floral design business, rejigged the photography, built Pop Up Weddings, a wedding subscription box, I Do Box.... When I say we're serious business builders, we're not lying. With every business move, we analyze + plan + move forward. We release what is not profitable and focus on the projects that are making bank. That's our story - we are serial creators.  And you get two for the price of one. We're a dynamic team, each with individual strengths that we can use to supercharge your business. Gary is a technical whiz, anything photography we got you. Kim is a marketing, systems and logistics queen. She'll figure out how to make it work, attack any issues like a pitbull and cheer you on while you reach your biggest goals. Connect with Gary & Kim Gary & Kim's website Gary & Kim's Instagram The off-camera flash freebie course The Tulum retreat + mood boards Gary's photography website Lovely Weddings Click here for more ways to listen to this episode.

    1h 6m

  5. JAN 8

    The Sales Call Mistakes Costing You Luxury Clients: Live Coaching with Jasmine Ortiz

    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 pricing?" Because that moment — where you're ready to raise your rates, step into a higher tier of client, and be paid like the artist you actually are — requires more than updating a number on a proposal. It requires an identity shift. In this conversation, Jasmine shares what's been happening as she raises her prices: how her old sales call script worked at a lower price point, but suddenly feels stiff, robotic, and way too logistics-heavy for the clients she wants to book now. And from there, I walk her through the exact framework I teach inside my one-to-one coaching and masterminds — the same structure that's helped photographers go from booking $3–6K weddings to booking $8K, $10K, $20K, even $30K. Because at the luxury and intro-luxury level, clients aren't choosing you because you're "easygoing" and "go with the flow." They're choosing you because you feel like a leader. A director. An artist with presence, taste, and a clear process. And the best part? You can learn that. You can practice that. You can embody that. In this episode, we talk about: Why so many photographers unintentionally dilute their authority by trying to be the couple's "bestie" How luxury clients want warmth, yes — but they also want clarity, confidence, and precision The difference between "participating" in the call vs. leading the call How to ask better questions than "So what's your vision?" Why selling at a higher level means selling an experience and a feeling, not hours and deliverables How to keep the first call exciting (and not turn it into a timeline-planning meeting) What to say instead of "We can totally do whatever you want" (because… no. Not if you're positioning luxury) The 7 shifts I gave Jasmine (you can steal these too): Before we recorded, Jasmine sent me a transcript of a real sales call — and once I read it, I found seven immediate tweaks that would completely change her conversions at a higher price point. Here they are: Stop being overly casual. Warm is good. Too familiar is not. Luxury requires a calm, grounded presence. Don't let the couple dictate the call. They don't want to run the show — they want to hire someone who can. Step into the identity of the director. You're not auditioning to be chosen. You're guiding them through a curated experience. Remove all "wishy-washy" language. "Whatever you want!" is not elegance. Recommendations are. Mirror their exact words back to them. This is huge. If you don't repeat their emotional buying criteria, they won't feel seen. Hold the space as an expert guide. Don't match chaos. Don't match overwhelm. You hold the calm. Stay professional while still being warm. Approachable, yes. Chatty friend energy, no. If you're in the season of raising your rates, hear me when I say: you don't just raise your prices — you raise your presence. You shift your language. You shift your leadership. You shift your identity. Because luxury clients aren't buying your packages. They're buying you.

    50 min

  6. 12/11/2025

    Talking to Trees and Dealing with Depression: D'Arcy's 2025 Reflection

    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 who's seen my behind-the-scenes, the unglamorous parts, the sacred parts, the parts that never make it to Instagram. And because this was a year of immense change, grief, healing, and rebirth, I wanted this conversation to be real. We talk about everything: The breakup. The depression. The healing journey in Bali and India. The spiritual reconnection I didn't see coming. The beauty that still insisted on blooming. The nervous system work that saved my life. Talking to trees. (Yes… literally.) And the small, holy ways I remembered myself again. This episode is tender, unpolished, and human — and I'm sharing it because if you are walking through something dark, I want you to know you aren't alone, and your story doesn't end there. So wherever you are — whether you're on a mountaintop celebrating or inching your way out of darkness — you're not behind. You're not broken. You're simply learning the wisdom that your soul came here to learn. Beauty is already blooming for you. Let it in. Thank you for walking with me through this year. Thank you for your prayers, your messages, your presence. I can't wait for what we'll create together in 2026 — the year of movement, momentum, freedom, and joy. Stay brave. Stay tender. Stay open to beauty. Much love, D'Arcy Click here for more ways to listen to this episode.

    1h 33m

  7. 12/04/2025

    The Art of High-End Weddings with Dawn Weisberg of Tularosa Flowers

    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 and television. We get into how those backgrounds shaped the way we approach weddings as world-building: cinematic, intentional, immersive, and deeply rooted in storytelling. We talk about: How Dawn went from starting florals at 45 to designing six-figure weddings in under a decade Why she treats every wedding like a film set: thinking in scenes, movement, and guest experience The behind-the-scenes systems and logistics that make large-scale productions possible How her viral "Malibu Barbie meets Marie Antoinette" pink wedding came to life — and what made it blow up online The creative process of pulling inspiration from runway shows, architecture, art, travel, and above all, the couple themselves Why color is having a moment in the luxury world and how to use it in a way that still feels timeless and elevated The mindset shifts required to feel safe holding and delivering on big budgets The role publications & Pinterest have played in her growth (and how she handles rejection like a pro) How styled shoots and editorials catapulted both of our careers into higher price points What florists actually need from photographers on a wedding day to grow their own businesses We also explore the emotional and energetic side of this work — what it's like to be genuinely obsessed with your craft, how to avoid burnout by building a business that actually feeds you, and why weddings are still the modern-day fairy tale for both couples and creatives. P.S. I'm hosting a Tuscany Real Wedding Workshop this spring — a real wedding with a real couple and 30 real guests, photographed and designed over multiple days. You'll walk away with: A full multi-day destination wedding story (engagement, welcome party, bridal editorial, wedding day, farewell event) A pre-trip mentorship to refine your brand, portfolio gaps, and shot list A post-trip call where we turn your gallery into a 90-day luxury marketing plan If your gut is saying "this is my next level," send me a DM and I'll send you the full proposal. We have very limited spots. Meet Dawn Dawn Weisberg is the owner and flower mastermind behind Tularosa Flowers, a luxury wedding design company in Southern California in the San Diego area. Voted Best Florist San Diego by California Wedding Magazine for both 2025 and 2024, she is dedicated to providing the highest level of design and service to her clients. Dawn's breadth of expertise enables her to offer a visionary edge to her work with a unique perspective in the wedding industry. With a Master's Degree in Theatrical Design from New York University's acclaimed Tisch School of the Arts, her classical training was augmented studying fine art in Italy, where she apprenticed in a Costume and Mask Studio in Venice. After a successful career for 20 years in film and television as a costume designer, Tularosa Flowers's owner chose to pursue her passion for flowers. Dawn combines her cinematic design background with her love of nature to create one-of-a-kind immersive experiences for her clients. The Tularosa style is an effortless maximalism combining Old World European style with California vibrance.  Tularosa Flowers has been featured in all of the top wedding publications, including Vogue, Martha Stewart Weddings, Style Me Pretty, Once Wed, The Knot, Brides, Ruffled, Green Wedding Shoes, California Wedding Day, Inspired by This, 100 Layer Cake, June Bug, Wedding Chicks, Hey Wedding Lady, Smashing the Glass, and the Gay Wedding Guide. Tularosa has also partnered with luxury brands including Hermes, and David Austin Wedding Roses. As one of the nation's top and premier floral designers, Dawn has appeared as a wedding trend expert on CBS and FOX, as well as multiple wedding industry podcasts, and was the Mayesh 2024 Wedding Florist Design Star. Connect with Dawn tularosaflowers.com Dawn's Instagram Dawn's TikTok Click here for more ways to listen to this episode.

    55 min

  8. 11/21/2025

    Live Coaching: When Marketing Feels Like Too Much (And What to Do Instead)

    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 this Part Two, we shift into strategy – creating a marketing plan that feels simple, sustainable, and true to who she is, instead of a giant pile of "shoulds" that leave her frozen and overwhelmed. I walk Staci through how to narrow her focus to just a few key marketing channels, how to build systems that support consistency (even if she doesn't feel like a "systems person"), and how to use her natural gifts as a caring, creative, fun-loving photographer to become a true client magnet. In this episode, we discuss: How to narrow your marketing down to 2–3 simple, sustainable channels you can actually stick with. A step-by-step venue networking strategy that turns tours into blogs, Pinterest content, and real bookings. Why Pinterest + blogging are a power duo for local markets like Savannah (and how to use them intentionally). How to stop fearing "wrong clients" and instead attract aligned couples through clear process and storytelling. Ways to collect specific, story-driven testimonials that actually sell your experience. How to use ChatGPT as your marketing assistant to map out a month of content that still feels like you. We wrap the call by replacing overwhelm with simplicity and grounding into the belief: "I am a client magnet. My caring, creativity, and courage draw aligned clients to me."   Resources Mentioned: Italy Workshop (Sicily + Real Wedding Experience) Join me for an immersive creative pilgrimage in Sicily or a once-in-a-lifetime real wedding weekend experience in Italy. Both workshops include coaching, portfolio curation, and hands-on shooting with stunning venues, world-class florals, and intimate group guidance designed to elevate your brand https://connectwed.net/workshop-sicily/ Free Training — 25 Marketing Tips My most-loved free resource packed with 25 high-impact, doable marketing ideas you can start using immediately https://darcybenincosa.com/25-marketing-tips Want a practical, step-by-step marketing strategy? Skip ahead to 21:12.

    51 min
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About

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!

Information

  • Creator
    D'Arcy Benincosa
  • Years Active
    2018 - 2026
  • Episodes
    268
  • Rating
    Explicit
  • Show Website
    Play It Brave Podcast

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