Reinventing Photography: Entrepreneur Jennifer Tsay on Empowering Creatives with a Pay-Per-Photo Model
Release Date: 11/11/2025
Salon to Software: Entrepreneur Erin Mills on When to Walk Away and Build Something Better
Wings of Inspired Business
Erin Mills is a visionary serial entrepreneur, salon owner, and advocate for women’s healing and empowerment, driven by a mission to create spaces where safety, growth, and authenticity thrive. From real estate to salon stylist, Erin built her salon business, Theory Salons, to challenge the male-dominated salon industry and its often-unsafe environments, before walking away from all but one of her locations to reinvent herself as a software entrepreneur with a new technology, Flamingo Salon Software, launching later this year. Her journey of reinvention also inspired her to create the Be...
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Plateaus to Profits: Entrepreneur Celi Arias on Scaling With the “Grown Ass Business” Method
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Celi Arias is the CEO and Founder of The Grown Ass Business, where she guides entrepreneurs through her proprietary methodology, Key Growth Systems, to build strong business foundations. Recognized as a top coach by The Upside in 2024, Celi helps clients break free from revenue plateaus and burnout by focusing on core business principles over quick fixes. Her approach emphasizes clarity and control, optimizing essential business departments to ensure solid foundations for scaling up to seven figures and beyond. She’s busy building software to scale her own business, now in beta at Get Scale....
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Red Carpets to Rest Wear: Celebrity Stylist and Entrepreneur Engie Hassan on Building Community for Women
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Engie Hassan is a celebrated red-carpet fashion stylist turned CEO and Founder of The Revelist, a membership community to help women in midlife feel better about themselves. An alum of Vogue, French Vogue, Teen Vogue and Numero, Engie is a sought-after arbiter of taste and a go-to connector, helping clients broker meaningful alliances with the who’s who of the fashion industry in the U.S., Europe and across the Arab world. Tastemakers such as Anna Wintour have lauded Engie for her vision for clients and the late Karl Lagerfeld singled out her eye for accessories. From The Oscars to the SAG...
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Living Longer, Better: Longevity Entrepreneur Leslie Kenny on Innovating the Anti-Aging Vitamin Primeadine
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Leslie Kenny is the CEO and founder of Oxford Healthspan, an innovative longevity company with a game-changing supplement called Primeadine. An Oxford-based longevity expert and Harvard alum, Leslie founded Oxford Healthspan after reversing her own Lupus, Rheumatoid Arthritis, and infertility and giving birth naturally at 43. Now 60, with a biological age of 21, she’s committed to helping others optimize their health span. Leslie is also co-founder of the Oxford Longevity Project, a nonprofit dedicated to public education on aging smarter with science-backed strategies. 🔑Key Takeaways🔑...
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Bianca D’Alessio, star of HBO Max’s acclaimed series Selling The Hamptons, is recognized as the top real estate broker in both New York City and New York state. Bianca founded one of the top real estate brokerage teams in the United States, where she manages a $10 billion international real estate portfolio. Having rebuilt her career through adversity, Bianca attributes her success to the art of mastering intention. Author of Mastering Intentions: 10 Practices to Amplify Power and Lead with Lasting Impact, she emphasizes the vital synergy between personal branding and business culture,...
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Gratitude & Giving Back: Winery Entrepreneur Maria Castellucci Moore on Navigating Change and Uncertainty
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Maria Castellucci Moore is the founder of the boutique winery and real estate business, Castellucci Napa Valley. She’s also a multi-award-winning author of the children’s book series Traveling Mindfulness, including Vivian in Paris and Sophia in Rome, and winner of the Gold Mom's Choice Award. First-generation American and mother to four children, Maria is also a board member of the San Francisco Opera Guild and Napa Valley's Ambassador to Charitable nonprofit organization, Roots of Peace— an organization that demines war torn lands and plants fruit orchards and vineyards worldwide....
info_outlineJennifer Tsay is the CEO and Co-Founder of the professional photography platform Shoott, which uniquely offers free photoshoots where clients only pay for the photos they love. Shoott operates in over 60 U.S. cities, supporting more than 750 freelance photographers with supplemental income, and maintain a 4.9 rating on Google across 2400 reviews and counting. With a diverse background in investment banking, strategic finance, project management, documentary film producing, and acting, Jennifer combines her passion for process with her love of art and storytelling to manage growth, strategy, and operations for Shoott. You may know Jennifer from her acting gigs on The Other Two, High Fidelity, The Village, The Blacklist, and Bored to Death as well as spots for Citi, AT&T Wifi, Samsung, Geico, and Manhattan Mini Storage. Jennifer is a Forbes #Next1000 entrepreneur and one of Brit + Co's 30 AAPI Founders We Love to Support, and recently appeared on Entrepreneur.com's Elevator Pitch Season 11.
🔑Key Takeaways🔑
🚀 📷 Disruptive Business Models Drive Growth: Learn how free photoshoots that let customers pay for the shots they love benefit consumers and creatives alike, allowing photographers to earn a steady income, find clients, and conserve their time.
🤟💰Solving the Artist Gig Dilemma: How photographic artists and gig workers can escape the feast-or-famine cycle with a platform that aggregates demand and creates accessible sessions in centralized, scenic locations, for steady income that supplements the work of talented photographers.
🦄 🎯 The 14-Day Rule: How to master lean, efficient marketing that gets results by testing quickly, abandoning things that don’t work after 14 days, avoiding the impulse to get “stuck on theory” and trust your own data over fads. Plus, why chasing marketing trends isn’t always best.
🎭📈 Acting to Investment Banking: How Jennifer’s diverse experiences shape how she’s building Shoott, blending creativity with data-driven problem solving.
🌍💡Scaling from NYC to 60 Cities (and Counting!): Learn how to navigate a double-sided marketplace, turn challenges into growth opportunities, hire remotely, and expand into new markets.
🎙️Subscribe to Wings and get the full Show Notes at https://bit.ly/Wings955
More about Jennifer at Shoott.com