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