Raising VC for Early-Stage AI: Lindsey Mignano on Challenges, Trends and Opportunities for Female Founders
Release Date: 09/09/2025
Gratitude & Giving Back: Winery Entrepreneur Maria Castellucci Moore on Navigating Change and Uncertainty
Wings of Inspired Business
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_outline
Raising Debt-Free College Grads: Entrepreneur Shellee Howard on College Prep and Empowering Kids for Self-Discovery
Wings of Inspired Business
Shellee Howard is the Founder and CEO of College Ready and CR Future Now, a Certified Independent College Strategist, and a best-selling author. A member of HECA and SOFA, she helps students gain admission to their best-fit colleges—often debt-free. As a mother of four, Shellee has firsthand experience with college success. Her son graduated debt-free from Harvard, earned his MD from UCSD, and is now an Orthopedic Surgery Resident at UCLA. Her daughter earned her BSN debt-free and became an RN in 2021. A sought-after speaker and consultant, Shellee has guided hundreds of students worldwide...
info_outline
Reinventing Photography: Entrepreneur Jennifer Tsay on Empowering Creatives with a Pay-Per-Photo Model
Wings of Inspired Business
Jennifer 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,...
info_outline
Cannabis Opportunities: Entrepreneur Wendy Bronfein on Funding, Franchises and Scaling Wellness
Wings of Inspired Business
Wendy Bronfein is the Co-Founder, Chief Brand Officer and Director of Public Policy at Curio Wellness, Maryland’s leading medical cannabis company, where she focuses on driving the company’s legislative agenda across multiple states and building the Curio brand. Wendy made the leap into the medical marijuana space after a long career in television. She was Creative Director of On-Air Promotions at LIVE! With Kelly & Michael and was a Managing Producer at BBC Worldwide Americas from 2006-2010. She has also served in various freelance production roles in New York and Los Angeles working...
info_outline
Reinventing Healthcare: Entrepreneur Chelsea Ryckis on Overcoming “The Big Lie” to Rethink Employer Benefits and Lower Costs
Wings of Inspired Business
Chelsea Ryckis is the award-winning founder and president of Ethos Benefits, a firm dedicated to advancing fiduciary-driven health insurance strategies for employers nationwide to eliminate fraud, waste, and abuse from employer healthcare plans while increasing savings for both employers and their employees. After suffering a traumatic brain injury as a Division 1 college athlete, Canadian-born Chelsea experienced the US healthcare system firsthand, inspiring her pioneering entrepreneurship in healthcare. Chelsea was awarded the industry’s most prestigious award, Advisor of the Year, by...
info_outline
More Heads to Turn: Entrepreneur Kate Assaraf on Growing A 7-Figure Sustainable Hair Care Without Amazon or Advertising
Wings of Inspired Business
Kate Assaraf is a serial entrepreneur and the founder and CEO of Dip Sustainable Hair Care, building a 7-figure beauty brand without Amazon, big-box retailers, or influencer gimmicks. Kate is also a Forbes columnist, and a mom of two who proves that entrepreneurship and motherhood can coexist without burnout—by prioritizing presence, purpose, and smart business choices. Kate has been featured in Allure, Cosmopolitan, Modern Salon, and The Unwash, was named NJ’s Mompreneur of the Year (2024), and was honored as a “Woman of Courage” by Insigniam Quarterly. She’s passionate about...
info_outline
Conscious Entrepreneurship: Lauren Morgan on Co-Creation and Tuning Into Your Business’s Unique Energy
Wings of Inspired Business
Lauren Morgan is the founder of Wild Wisdom, an energy master, and a trauma recovery and business coach on a mission to empower women overcome imposter syndrome, limiting beliefs and self-sabotage so they can turn their pain into purpose, transform their wounds into wisdom, and create heart-centered businesses. She brings her personal expertise with healing practices like Ayurveda, hypnosis, meditation, shamanism, energy work, and core belief work to help entrepreneurs grow abundant, purpose-driven businesses. 🔑Key Takeaways🔑 ✨🔹 Your Business Has Its Own Consciousness: Think of your...
info_outline
Insider IRS Secrets: Sherry Peel Jackson on Protecting and Growing Wealth in Uncertain Times
Wings of Inspired Business
Dr. Sherry Peel Jackson is a retired IRS agent, CPA, and Certified Fraud Examiner who’s helped over 100,000 professionals legally reduce taxes and build lasting wealth. With over 35 years of experience, she’s the creator of the KPG System—a proven method to Keep, Protect, and Grow your income without risky investments. She’s also the author of How To Escape The Rat Race and a passionate speaker empowering people to take control of their finances and create generational wealth. 🔑Key Takeaways🔑 💰 📈 What the IRS Doesn’t Want You to Know: Learn the inside secrets of how...
info_outline
Robots for the Future: Entrepreneur Jenny Young on Empowering Kids’ Creativity Through Hands-On Robotics Development
Wings of Inspired Business
Jenny Young is the Founder and CEO of Brooklyn Robot Foundry, the vibrant and inclusive brand dedicated to prioritizing diversity and empowerment for children of all backgrounds and communities through STEAM education. Jenny is a trained mechanical engineer turned entrepreneur to bring a more diverse, inclusive and creative approach to STEAM education. Founded in 2011 and with four locations open currently, the brand focuses putting the “art” in science, technology, engineering and mathematics (STEM) and sharing the fun of STEAM education with children everywhere, inspiring them to...
info_outline
Females in Franchising: Entrepreneur Brittney Lincoln on Helping Women Scale Brands and Take Locations from 1 to 100
Wings of Inspired Business
Brittney Lincoln is the CEO and Founder of Females in Franchising, a dynamic platform dedicated to empowering women in the franchising industry. With over 13 years of experience spanning home services, beauty, and medical franchises, Brittney has built a reputation as a connector, educator, and strategist in the franchising world. She is passionate about providing a space for women to collaborate, learn from industry experts, and grow both personally and professionally. Her expertise lies in helping business owners understand franchising, scale their brands, and take their locations from one...
info_outlineLindsey S. Mignano is the founder of SSM Legal, an entrepreneurial Silicon Valley corporate lawyer representing emerging technology companies and industry-adjacent firms and small businesses. Her practice spans technology company business formation and expansion into US markets, M&A (flips, entity or asset sales), commercial and technology transactions, and venture financing. Lindsey has been recognized as a “Rising Star” by Super Lawyers every year from 2016-2024, an honor awarded to only 2.5% of attorneys under the age of 40. In 2025, she was awarded the Super Lawyers distinction for the first time at the age of 40, an honor awarded to only 5% of attorneys. Separate from her law practice, Lindsey speaks often about diversity issues in the fields of law, tech, and venture. In 2023, Lindsey founded Venture Betches, a venture fund of funds, and Syndicate Betches, a real estate syndicate fund of funds, both with a social justice mission to bring investment opportunities to historically underrepresented accredited limited partners who identify as female and/or BIPOC/minorities.
🔑Key Takeaways🔑
💰 🚀 Fewer Early-Stage Deals, But Bigger Checks for the Chosen Few: While overall early-stage investment (seed & Series A) is down sharply, those who do close are raising larger rounds. AI startups are a bright spot—median deal size for early-stage AI is $4.6M vs. $3.5M in other sectors.
🛠️🔥The Funding Bar Is Higher Than Ever: VCs are pickier, demanding traction, ARR, and “proof” even at seed stage. This can be a real Catch-22 for founders who need funding to hit those milestones.
👩🔬🛑 The Gender Gap Persists—And Is Widening: Female founders face staggering disparities in deal count and dollars. In 2025, only 5.3% of all deals went to all-female teams, and a shocking 0.8% of total venture dollars. The dynamic is especially tough for solo women founders in technical AI, who often face pressure to take on male CTOs and cede equity to “pass” the VC filter.
✨💡 Tips for Women and Diverse Founders: Feeling daunted?
-
Seek out emerging venture managers and female-run funds for your first checks—but be mindful of not being pigeonholed at the next funding stage.
-
Build authentic relationships with decision-makers (not just associates).
-
Don’t hesitate to get creative about showcasing traction, even with limited resources.
-
Find legal and business partners who share your values and play the long game.
🎙️Subscribe to Wings and get the full Show Notes at https://bit.ly/wings-946
More about Lindsey at SSM Legal