From English major to billion-dollar entrepreneur, Lindsay Kaplan shares how her creativity, rebellious spirit, and refusal to follow the rules led her to co-found Chief, the premier network for executive women.

Lindsay’s journey is anything but traditional. She began her career with dreams of writing novels, moved into publishing and magazines, and then found herself on the cutting edge of digital marketing during the early days of Facebook and Foursquare. Her storytelling expertise eventually brought her to Casper, where she became a founding team member, built global campaigns, and helped turn a mattress startup into a cultural phenomenon. But it was her partnership with Carolyn Childers that sparked her biggest leap, co-founding Chief, now a billion-dollar company reshaping what leadership looks like for women at the VP and C-suite levels.

In our conversation, Lindsay opened up about the pivotal moments that shaped her leadership path, from building credibility as a nontraditional founder, to navigating the challenges of co-founding a VC-backed company, to realizing when it was time to step into a board role to protect her own health and longevity. She emphasizes the importance of finding co-founders who share your values, the realities of burnout that often accompany leadership, and why flexibility, not perks, is the true key to retaining women in executive roles.

What stands out most about Lindsay is her deep commitment to creating spaces where women leaders can both give and receive mentorship. Chief was built on the belief that even the most senior leaders need support, and Lindsay’s story is a powerful reminder that community is not a luxury — it’s a necessity. Listeners will walk away inspired by her candid reflections on career evolution, her practical wisdom on building and scaling companies, and her fierce advocacy for women at the top of their fields.

This is an episode you won’t want to miss! Tune in and hear Lindsay’s incredible story of creativity, resilience, and leadership redefined.

Chapters
👩‍💼 00:55 Meet Lindsay Kaplan and Her Leadership Journey

🚀 04:55 From Creative Roots to Entrepreneurship

🌟 08:15 Building Chief as a Network for Women Executives

🤝 10:56 Why Shared Values Make Partnerships Stronger

💼 13:49 Breaking Barriers for Women in Corporate Leadership

🏢 17:28 How Physical Spaces Strengthen Community

⚖️ 18:49 Finding Balance Between Work and Personal Life

🔮 24:34 The Future of Chief and Women’s Leadership

Links

Website: http://chief.com
LinkedIn: https://www.linkedin.com/in/lindsaykap/
Email address: lindsaykap@gmail.com
Check out Lindsay Kaplan’s work at Chief, connect with her on LinkedIn, and explore how she’s building the future of executive leadership for women.

Reach out to Adrienne: hello@sheleadsmedia.com

Visit our website: www.sheleadsmedia.com

Join us at the upcoming She Leads LIVE 2025 conference in NYC on November 6th & 7th. Learn more at sheleadsmedia.com

"I love ♥️ listening to The She Leads™ Podcast!” If that thought crossed your mind at any time while listening to our special show, I’d love it if you would take a moment and give our podcast some love too. To do so, simply Rate, Review & Follow Us on Apple Podcasts & Spotify. Taking this simple action helps my team and I to spread the word about all the incredible guests featured on The She Leads Podcast and contributes overall to helping women leaders and entrepreneurs everywhere! 🗺 Also, if you haven’t done so already, please +follow the podcast so you never miss an episode. Thank you so much!!

— Adrienne

From nannying and late-night valet shifts to building two thriving businesses, Olivia Shears shares how creativity, grit, and a willingness to pivot have shaped her journey as a leader and entrepreneur.

Olivia’s entrepreneurial story started in unexpected ways. Working double shifts while in college and missing out on time with her mom pushed her to launch a picnic design business in 2020. When rising costs and changing demand forced her to close that chapter, she discovered her real passion for social media marketing, which led her to found Social Bean Agency in 2021.

At Social Bean Agency, Olivia brings a hands-on, personal approach to every client, treating accounts as if they were her own. She has built her business through networking and referrals while navigating the challenges of perfectionism, encouraging other women entrepreneurs to show up authentically online, experiment, and stay consistent rather than waiting for perfection.

Her entrepreneurial leadership doesn’t stop there. Olivia co-founded Long Distance Besties with childhood friends Shelby and Mason, turning years of shared letters and creative games into a journal business that has grown to nearly 15,000 followers and sparked international sales. Their work highlights Olivia’s ability to identify overlooked needs and build meaningful, scalable solutions that celebrate connection.

In this episode, we dive into Olivia’s journey of leadership, creativity, and adaptability, exploring how she turns challenges into opportunities and grows businesses that matter. Tune in to hear her insights and learn how she approaches entrepreneurship with authenticity, strategy, and heart.

Chapters
💌 01:55 The Journey of Long Distance Besties
🌿 03:49 From Picnics to Social Media and Olivia’s Business Evolution
🔥 05:13 Overcoming Challenges and Finding Passion
📱 09:45 Building a Successful Social Media Agency
💡 12:32 Advice for Women Entrepreneurs on Social Media
✨ 17:01 The Importance of Authenticity in Social Media
🌍 21:32 Exploring Long Distance Besties in Depth

Links
Website: socialbeanagency.com
Social Media: @LongDistanceBestiesLDB / @SocialBean.Agency
Email address: socialbeanagency1@gmail.com
Check out Olivia’s website, follow her on Instagram, and explore Long Distance Besties to find inspiration for building authentic connections across every stage of life and business.

Reach out to Adrienne: hello@sheleadsmedia.com

Visit our website: www.sheleadsmedia.com

Join us at the upcoming She Leads LIVE 2025 conference in NYC on November 6th & 7th. Learn more at sheleadsmedia.com

"I love ♥️ listening to The She Leads™ Podcast!” If that thought crossed your mind at any time while listening to our special show, I’d love it if you would take a moment and give our podcast some love too. To do so, simply Rate, Review & Follow Us on Apple Podcasts & Spotify. Taking this simple action helps my team and I to spread the word about all the incredible guests featured on The She Leads Podcast and contributes overall to helping women leaders and entrepreneurs everywhere! 🗺 Also, if you haven’t done so already, please +follow the podcast so you never miss an episode. Thank you so much!!

— Adrienne

From cancer survivor to pioneering fertility attorney, Rijon Charne has turned personal adversity into advocacy and entrepreneurship. In this episode of She Leads, she shares how battling Hodgkin’s lymphoma led her to challenge insurance denials, lobby for fertility preservation rights, and ultimately build one of the nation’s leading reproductive law firms.

Rijon shares how her battle with Hodgkin’s lymphoma shortly after law school shifted her path from litigation to advocating for fertility preservation. Through her firm, Sunray Fertility Law, Rijon guides clients through surrogacy, egg and sperm donation, embryo agreements, and cross-border fertility matters.

Rijon’s journey was shaped by critical turning points, from confronting potential infertility at 26 to challenging insurance denials that threatened her own fertility. These experiences inspired her to ensure others wouldn’t face the same obstacles, turning personal setbacks into a purpose-driven venture that serves an important purpose. Her logical approach, strong support system, and determination were central to this transformation.

She offers practical guidance on navigating fertility law, emphasizing clear contracts, understanding insurance benefits, and advocating for parental rights in diverse family structures. Rijon also shares lessons in entrepreneurship, including hiring the right team, seeking mentorship, and balancing resilience with growth while running a law firm.

This conversation highlights broader themes of leadership, perseverance, and advocacy. Listeners will find inspiration in Rijon’s dedication to educating others, empowering informed reproductive choices, and creating smoother pathways for families.

Tune in to hear Rijon Charne’s story, gain actionable insights on reproductive law, and discover how one attorney is making a meaningful impact for families worldwide.

Chapters
🎙️ 00:56 Meet Rijon Charne, Fertility Attorney
🌟 03:22 Rijon's Personal Journey with Cancer and Fertility
⚖️ 06:00 Advocating for Reproductive Rights
🏛️ 12:06 Building Sunray Fertility Law into a Successful Practice
💪 18:17 Balancing Client Needs with Personal Health
📜 20:03 Navigating Legal Aspects of Fertility Treatments
⚡ 24:30 Addressing Controversies in Fertility Law
🌸 27:11 Empowering Women Through Advocacy
📚 28:37 Resources and Final Advice

Links
Website: https://sunrayfertility.com/
Social Media: @sunrayfertilitylaw
Email address: rijon@sunrayfertility.com
Connect with Rijon Charne to explore Sunray Fertility Law’s services, gain insights on reproductive rights, and access resources that empower individuals and families navigating fertility challenges.

Reach out to Adrienne: hello@sheleadsmedia.com

Visit our website: www.sheleadsmedia.com

Join us at the upcoming She Leads LIVE 2025 conference in NYC on November 6th & 7th. Learn more at sheleadsmedia.com

"I love ♥️ listening to The She Leads™ Podcast!” If that thought crossed your mind at any time while listening to our special show, I’d love it if you would take a moment and give our podcast some love too. To do so, simply Rate, Review & Follow Us on Apple Podcasts & Spotify. Taking this simple action helps my team and I to spread the word about all the incredible guests featured on The She Leads Podcast and contributes overall to helping women leaders and entrepreneurs everywhere! 🗺 Also, if you haven’t done so already, please +follow the podcast so you never miss an episode. Thank you so much!!

— Adrienne

At just 24, Maddie Pollack faced a life-changing Hodgkin’s lymphoma diagnosis—and transformed her healing journey into a mission to empower women through holistic health and entrepreneurship.

In this episode of She Leads, Maddie shares how her battle with cancer became the wake-up call that shifted her from an unhealthy lifestyle to becoming an integrative nutrition health coach. Now, she helps women reconnect with their bodies through a balanced approach that weaves together nutrition, mindful movement, and self-care. Her story is not only one of survival, but of reclaiming purpose and aligning wellness with leadership.

Maddie dives into the personal health challenges that can arise in the wake of illness, from hormonal imbalances to stress-related symptoms. Maddie candidly reflects on her own experience with recovery and the lifestyle changes that helped her restore balance, including shifting from high-intensity workouts to strength training and yoga, and prioritizing protein-rich meals to stabilize energy and hormones. The conversation expands to highlight the overlooked realities of women’s health, from PCOS and irregular cycles to the ways traditional studies have ignored female physiology.

Listeners will gain practical insights into building sustainable wellness habits: nourishing the body with balanced meals, syncing workouts with menstrual cycles, managing cortisol through mindful movement, and embracing daily rituals like journaling, gratitude, and deep breathing to calm the nervous system. Maddie emphasizes that health is not about rigid routines, but about tuning into the body’s signals and making adjustments that support long-term vitality.

At its core, this episode reframes leadership and entrepreneurship through the lens of well-being. Maddie challenges the outdated narrative that success requires burnout and sacrifice, instead advocating for a model where women prioritize health as the foundation for growth, freedom, and fulfillment. Her reflections serve as a powerful reminder that honoring your body is not just a personal practice—it’s a leadership strategy.

Tune in to hear Maddie’s inspiring story and learn how to cultivate balance, resilience, and true alignment in both business and life.

Chapters
👩 00:56 Meet Maddie Pollock A Journey of Resilience
💧 03:22 Diving into Wellness Maddie's Transformation
⚖️ 06:26 Understanding Hormonal Health
🌿 12:18 Practical Tips for Hormonal Balance
🏋️‍♀️ 22:03 Navigating Menopause with Strength Training Tips
📈 23:36 Balancing Work and Exercise for Entrepreneurs
🧘 26:30 The Importance of Mindfulness
😌 29:50 Managing Stress and Cortisol Levels
👩‍💼 33:07 Leadership and Self-Care for Women Entrepreneurs

Links
Website: maddypollackhealth.com
Social Media: @maddypollack_health
Email address: maddy@maddypollackhealth.com
Check out Maddy Pollack’s website, connect with her on Instagram, and explore her coaching resources to start living in sync with your body today.

Reach out to Adrienne: hello@sheleadsmedia.com

Visit our website: www.sheleadsmedia.com

Join us at the upcoming She Leads LIVE 2025 conference in NYC on November 6th & 7th. Learn more at sheleadsmedia.com

"I love ♥️ listening to The She Leads™ Podcast!” If that thought crossed your mind at any time while listening to our special show, I’d love it if you would take a moment and give our podcast some love too. To do so, simply Rate, Review & Follow Us on Apple Podcasts & Spotify. Taking this simple action helps my team and I to spread the word about all the incredible guests featured on The She Leads Podcast and contributes overall to helping women leaders and entrepreneurs everywhere! 🗺 Also, if you haven’t done so already, please +follow the podcast so you never miss an episode. Thank you so much!!

— Adrienne

From psychologist to business strategist — Gail Golden shares her journey of curating life and leadership, helping overwhelmed leaders focus on what truly matters while scaling businesses with clarity and purpose.

In this episode of the She Leads podcast, host Adrienne welcomes Gail Golden, a seasoned coach, psychologist, and author of Curating Your Life. Drawing from her experience supporting executives and entrepreneurs, Gail introduces her framework for designing life as a personal exhibit — prioritizing what’s essential, discarding distractions, and embracing “good enough” in areas outside one’s true passions.

Gail reflects on her leap into entrepreneurship during the 2009 financial crisis, sharing lessons on adaptability, competitive positioning, and evolving strategies from startup survival to million-dollar growth. She underscores the importance of delegation, reminding leaders to focus only on what only they can do — whether in business or in personal roles like parenting and caregiving.

The conversation also explores the hidden costs of over-responsiveness, the mental barriers that hold leaders back, and the dangers of comparing private struggles to others’ public appearances. Gail highlights the power of self-awareness, managing inner critics, and working with a coach who blends business expertise with psychological insight.

With warmth and wisdom, Gail invites listeners to re-curate their lives as priorities shift, embrace meaningful relationships, and find strength in conscious choices. Hopefully, her insights will leave you inspired to design the next chapter of your life with intention and courage.

Ready to rethink how you’re curating your own life and leadership? Tune in to be inspired by Gail Golden’s story and practical framework for success!

Chapters
👩‍💼 00:59 Meet Gail Golden: Strategic Coach and Author

🧩 03:08 Curating Your Life Framework

🚀 10:42 Transitioning from Corporate to Entrepreneurship

📈 15:06 Scaling Your Business to the Next Level

📝 22:30 The Importance of Delegation

🔎 23:34 Assessing and Curating Your Life

⚡ 24:58 The Impact of Immediate Responsiveness

🧠 30:36 Understanding and Overcoming Mental Barriers

🎯 34:42 The Role of Coaching in Personal and Professional Growth

Links
Website: http://www.gailgoldenconsulting.com/
Social Media: @goldencoach
LinkedIn: linkedin.com/in/gailgolden
Email address: ggolden@gailgoldenconsulting.com
Check out Gail Golden’s website, explore her book Curating Your Life, and connect with her for resources and coaching to start designing a life and business that truly matter.

Reach out to Adrienne: hello@sheleadsmedia.com

Visit our website: www.sheleadsmedia.com

Join us at the upcoming She Leads LIVE 2025 conference in NYC on November 6th & 7th. Learn more at sheleadsmedia.com

"I love ♥️ listening to The She Leads™ Podcast!” If that thought crossed your mind at any time while listening to our special show, I’d love it if you would take a moment and give our podcast some love too. To do so, simply Rate, Review & Follow Us on Apple Podcasts & Spotify. Taking this simple action helps my team and I to spread the word about all the incredible guests featured on The She Leads Podcast and contributes overall to helping women leaders and entrepreneurs everywhere! 🗺 Also, if you haven’t done so already, please +follow the podcast so you never miss an episode. Thank you so much!!

— Adrienne

From superfoods to nationwide success — Tara Gilad shares her journey through building Vitality Bowls, balancing motherhood, and empowering women entrepreneurs through franchising.

Discover how Tara transformed a personal mission to create allergy-friendly dining for her daughter into a booming health and wellness franchise with over 120 locations. Starting from her roots in Northern California, she navigated the male-dominated restaurant industry with resilience, confidence, and a purpose-driven vision.

Tara opens up about the challenges of scaling a franchise while raising a family, the importance of surrounding yourself with the right team, and why passion and personality matter most in successful franchising. She also highlights the value of transparency, trust, and strong support systems in ensuring franchisee success.

Today, Tara continues to champion women in business, writing children’s books, prioritizing self-care, and offering aspiring entrepreneurs opportunities to grow with Vitality Bowls. She even shares a special offer for listeners interested in franchising.

Ready to hear how purpose, perseverance, and passion fueled one woman’s path from a single smoothie bowl café to a thriving nationwide brand? Tune in to be inspired by Tara Gilad’s remarkable story!

Chapters
💪 04:42 Building confidence through early businesses in Silicon Valley without fear
🚺 05:20 Breaking barriers as a female founder in the male-dominated restaurant and franchise industry
🌱 08:19 Balancing motherhood, entrepreneurship, and purpose-driven growth while staying adaptable
🤝 10:52 Entering franchising by networking, seeking mentors, and learning quickly
👩‍🍳 13:05 Leading with trust and clarity while supporting franchisees nationwide through data-driven decisions
🔥 15:13 Defining a great franchisee through passion and personality above all else
📚 21:45 Overcoming burnout, writing children’s books, pursuing personal passions, and creating space for joy
💲 25:50 A special Vitality Bowls franchisee discount code for listeners!

Links

Website: vitalitybowls.com
Social Media: @vitalitybowls
Email: thea@vitalitybowls.com
Check out Tara's website, or look her up on social media to learn more about the Vitality Bowls franchise!

Reach out to Adrienne: hello@sheleadsmedia.com

Visit our website: www.sheleadsmedia.com

Join us at the upcoming She Leads LIVE 2025 conference in NYC on November 6th & 7th. Learn more at sheleadsmedia.com

"I love ♥️ listening to The She Leads™ Podcast!” If that thought crossed your mind at any time while listening to our special show, I’d love it if you would take a moment and give our podcast some love too. To do so, simply Rate, Review & Follow Us on Apple Podcasts & Spotify. Taking this simple action helps my team and I to spread the word about all the incredible guests featured on The She Leads Podcast and contributes overall to helping women leaders and entrepreneurs everywhere! 🗺 Also, if you haven’t done so already, please +follow the podcast so you never miss an episode. Thank you so much!!

— Adrienne

From Hollywood producer to venture capital advocate — Catherine Gray is on a mission to close the funding gap for women and ignite a global movement through film, books, and bold action.

Catherine Gray CEO of She Angel Investors, Executive Producer of the movie, Show Her The Money as well as Host of the Podcast Invest In Her, shares how she’s turning the tide on a staggering statistic: women receive just 2% of venture capital funding. In this insightful episode, she reveals how her award-winning film Show Her the Money is educating women on the power of venture capital, shifting mindsets about wealth, and inspiring women to invest in each other.

From producing movies to launching the She Angels Foundation, Catherine has spent her career spotlighting women founders and connecting them to the resources they need to scale. She discusses why finding “your people” is critical in fundraising, the overlooked opportunities in underserved communities, and the massive wealth transfer heading into women’s hands. Her approach blends storytelling with actionable strategies, proving that doing good and making a profit are not mutually exclusive.

Whether you’re an aspiring entrepreneur, a future investor, or simply curious about how money can be a tool for change, Catherine’s story will challenge your thinking and inspire you to take action.

Ready to learn how investing in women can change the world? Tune in to hear Catherine Gray’s bold vision for funding the future.

Chapters
📊 02:55 Show Her the Money: The "moviement" helping to make venture capital more accessible and exciting for women
💡 11:40 Finding the right investors who see your vision instead of convincing the wrong ones
💖 15:01 Nonprofit investing is important, but investing in for-profit women and making good money from it is also a way to do great things for the world
📚 17:36 Go learn about investing! Starting small with angel investing and learn by doing
💵 20:58 IRA or other pension funds are an underutilized way to start making alternative investments
🎓 24:25 Inspiring young women to consider venture capital as a career path
🤝 27:17 Why underserved communities must be at the decision-making table as investors
♻️ 29:48 The cycle of getting investments and investing back in your own people
🎬 31:50 Building a movement with live and virtual screenings to spark action
📖 35:32 Launching the Show Her the Money book and combining screenings with book events

Links

Website: https://showherthemoneymovie.com
Instagram: instagram.com/showherthemoney
Facebook: facebook.com/ShowHerTheMoney
LinkedIn: linkedin.com/in/catherinelgray
Email address: catherine@sheangelinvestors.com
Check out Catherine Gray’s website and follow her on social media to learn more about investing in women and joining the Show Her the Money movement.

Reach out to Adrienne: hello@sheleadsmedia.com

Visit our website: www.sheleadsmedia.com

Join us at the upcoming She Leads LIVE 2025 conference in NYC on November 6th & 7th. Learn more at sheleadsmedia.com

"I love ♥️ listening to The She Leads™ Podcast!” If that thought crossed your mind at any time while listening to our special show, I’d love it if you would take a moment and give our podcast some love too. To do so, simply Rate, Review & Follow Us on Apple Podcasts & Spotify. Taking this simple action helps my team and I to spread the word about all the incredible guests featured on The She Leads Podcast and contributes overall to helping women leaders and entrepreneurs everywhere! 🗺 Also, if you haven’t done so already, please +follow the podcast so you never miss an episode. Thank you so much!!

— Adrienne

From D1 athlete to global entrepreneur — Rebekah Jenkins shares her journey to becoming a Web3 CEO, scaling with video and AI, and helping women hit $10K months and beyond.

Discover how Rebekah Jenkins, a former D1 tennis player and award-winning coach, boldly pivoted into the blockchain industry to become the CEO of Beks Media. This fascinating episode reveals how she leveraged her psychology background and competitive spirit to navigate the male-dominated tech world and build a successful media marketing agency.

Rebekah shares her journey from receiving a prestigious national tennis award to recognizing her true calling in business. Her story includes a pivotal moment at a Las Vegas investment conference that led to unexpected opportunities in Europe's blockchain scene. Despite experiencing some initial technical knowledge gaps, she went on to a successful exit. Rebekah, never one to sit on her success, decided to pursue her MBA at the prestigious Rice University to strengthen her business acumen.

Today, Rebekah is spearheading an innovative project in Berlin focused on affordable housing through tokenization and data centers, with speaking, writing a book, and living part time in the US & part time in Europe. Her experience underscores the power of embracing change, continuous learning, and trusting one's intuition to guide the path forward.

Ready to be inspired by this remarkable story of transformation and entrepreneurial courage? Tune in to hear how Rebekah Jenkins turned challenges into stepping stones for success!

Chapters

🎾 02:50 Rebekah’s journey from D1 tennis and national coaching awards to building businesses that change the world
🌍 05:18 A bold leap: Selling everything, moving to Europe, and jumping into blockchain with a German partner
💼 07:05 Becoming a Blockchain CEO: Co-founding a Swiss company after an initial failure and raising millions
🚧 10:33 Having incredible success in a male-dominated industry as a young woman
🎓 15:22 Pursuing a top-ranked online MBA while living globally
🧘‍♀️ 21:34 Minimalism & clarity: Cultivating intuition, identity, and laser focus through simplicity
👤 24:20 Know thyself: navigating identity issues
🚀 33:03 Building a following, teaching content automation and why you must be creating short-form video!
💖 34:45 Using business and money to serve others, not just profit

Links

Website: https://www.beksmedia.com/
LinkedIn: https://www.linkedin.com/in/rebekah-jenkins-mba-0739b051/
Check out Beks Media and Rebekah’s LinkedIn to learn more.

Reach out to Adrienne: hello@sheleadsmedia.com

Visit our website: www.sheleadsmedia.com

Join us at the upcoming She Leads LIVE 2025 conference in NYC on November 6th & 7th. Learn more at sheleadsmedia.com

"I love ♥️ listening to The She Leads™ Podcast!” If that thought crossed your mind at any time while listening to our special show, I’d love it if you would take a moment and give our podcast some love too. To do so, simply Rate, Review & Follow Us on Apple Podcasts & Spotify. Taking this simple action helps my team and I to spread the word about all the incredible guests featured on The She Leads Podcast and contributes overall to helping women leaders and entrepreneurs everywhere! 🗺 Also, if you haven’t done so already, please +follow the podcast so you never miss an episode. Thank you so much!!

— Adrienne