In this episode, we welcome the multi-talented Issa Rae for a candid conversation about entrepreneurship, creative growth, and the power of collaboration. Issa shares her journey from the early days of Awkward Black Girl to becoming a trailblazer in entertainment and business. Issa’s passion for building community shines through her investments and partnerships, including her work with Hilltop Coffee + Kitchen and her commitment to uplifting South LA.

We dive into Issa’s experiences navigating Hollywood, building successful businesses, and the importance of finding the right people to support your vision. She shared candid stories about meeting her business manager “by chance,” learning to manage her finances, and the importance of patience and trust in every partnership. Issa also highlights the unique strengths of her collaborators, Ajay and Yonnie, and how their shared vision helped bring Hilltop Coffee + Kitchen to life.

This episode is filled with laughter, honest reflections, and invaluable lessons on staying true to your purpose while expanding into new ventures. Whether you’re an aspiring entrepreneur, a creative, or someone who loves inspiring stories, this episode is for you.

Welcome to It Takes A Village with Delina Medhin, where inspiring founders & creatives share ‘who I built this with’.

00:00 Balancing Acting and Business

01:09 The Power of Finding the Right People

03:20 The Start of Hilltop Coffee

4:35 The Dynamic Between Ajay & Yonnie

Learn more about Issa Rae:

Issa Rae is an Emmy® and Golden Globe®-nominated actress, writer, producer, and entrepreneur. She first gained attention with her award-winning web series and New York Times best-seller, The Misadventures of Awkward Black Girl. As the founder of HOORAE Media, Issa champions diverse storytelling across film, TV, and music. Her investments in local businesses, including Hilltop Cafe + Kitchen and Sienna Naturals, reflect her dedication to empowering her community and reimagining Black wellness and creativity.

Listen to the full episode on Apple Podcasts: https://podcasts.apple.com/us/podcast/s3-ep-54-issa-rae-the-entrepreneur/id1580081881?i=1000686268868

Listen to the full episode on Spotify: https://open.spotify.com/episode/59XpGGDYM5VihvMXaqfCmR?si=8ad0ad72fdf94d4e

Connect with Issa Rae:

Instagram https://www.instagram.com/issarae

Youtube https://www.youtube.com/issarae

LinkedIn: https://www.linkedin.com/in/issarae/

Facebook https://www.facebook.com/findyourhilltop/

Instagram https://www.instagram.com/findyourhilltop

Tiktok https://www.tiktok.com/@hilltopfortheclimb

X (Twitter) https://x.com/findyourhilltop

Facebook https://www.facebook.com/HOORAEMedia/

Instagram https://www.instagram.com/hooraemedia/​

Youtube @HOORAEMedia 

Tiktok https://www.tiktok.com/@hooraemedia

X (Twitter) https://x.com/hooraemedia

Website https://hoorae.co/

Connect with the Host, Delina Medhin:

Instagram: https://www.instagram.com/delinamedhin

TikTok: https://www.tiktok.com/@delinamedhin

YouTube: https://www.youtube.com/@Delinamedhin

Threads: https://www.threads.net/@delinamedhin

Website: https://www.delinamedhin.com/

#ittakesavillage #issarae #entrepreneurship #partnership #businessgrowth