In this episode, I talk with Leigh Holt, founder of maddjett and co-founder of Hsquared Management, who has helped shape the careers of many artists and personalities like Lauren Daigle, Riley Clemmons, Lizzie Morgan, Demi Tebow, Jeremy Rosado, Jordan St. Cyr and Annie F. Downs.

Founder and CEO of multiple entertainment ventures, Leigh Holt has built her career on identifying market opportunities and creating innovative solutions in the artist management and brand development space.

Through her companies maddjett and Hsquared Management, she’s pioneered entrepreneurial approaches that have transformed how talent connects with audiences and how brands engage with entertainment.

Her ventures have been instrumental in securing multiple Grammy wins and nominations, Billboard and American Music Awards, launching bestselling authors, and developing groundbreaking partnerships with Fortune 500 companies.

As a founder, she’s cultivated organizations that combine creative vision with business acumen, resulting in multiple Guinness World Records, 475+ sold out events, and partnerships with global brands including Pepsi, Proctor & Gamble, Toyota, and IKEA.

She continues to push the boundaries of what's possible in entertainment management through strategic innovation and entrepreneurial leadership.

We talk about:

• ​The real role of a manager and what great management actually looks like
• ​Why great music is still the foundation in a noisy industry
• ​The strategic decisions behind crossover success
• ​How to choose the right partners and build the right team
• ​Mistakes artists make when momentum starts to build
• ​How to navigate fear, criticism, and pressure in the public eye
• ​Why identity and authenticity matter more than copying someone else’s path

This is a grounded, honest look at what it really takes to build something sustainable in today’s music industry.

If you’re serious about growing as an artist, this conversation will challenge how you think and how you build.

If you’re an independent Christian artist looking for clarity, strategy, and support, you can apply for Christian Artist Mentorship.

Let's Connect:

• ​⁠⁠⁠Christian Artist Mentorship⁠⁠⁠ (Next Cohort Begins April 21)
• ​⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Wisdom Moon on Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠
• ​⁠⁠⁠Christian Artist Mentorship on Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠
• ​⁠⁠⁠Christian Music Marketing on Instagram⁠⁠⁠
• ​⁠⁠⁠Pure Mosaic Services⁠⁠

Connect with Leigh Holt:

maddjett.com

Hsquared Management

In this episode, Wisdom sits down with Brian Ortize, who has spent over 25 years in music, from touring in his teens to serving as a worship pastor and church planter in Hollywood, CA. He later spent nearly a decade in A&R at Tooth & Nail / BEC Recordings and now focuses on film and TV development.

Brian shares his story of navigating different seasons, stepping into new opportunities, and building a career through faith and relationships. They also talk about the realities of the Christian music industry and what artists need to understand as they grow.

If you are an artist, songwriter, or creative trying to find your path, this conversation will give you perspective and encouragement for the journey ahead.

Let's Connect:

• ⁠⁠Christian Artist Mentorship⁠⁠ (Next Cohort Begins April 21)

• ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Wisdom Moon on Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

• ⁠⁠Christian Artist Mentorship on Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

• ⁠⁠Christian Music Marketing on Instagram⁠⁠

• ⁠⁠Pure Mosaic Services⁠

Connect with Brian Ortize:

tiktok.com/@brianmortize

In this episode, Wisdom sits down with songwriter Rhyan Shirley to talk about the real path to building a songwriting career.

Rhyan Shirley is a BMI award-winning songwriter who has been writing since she was just 7 years old, starting at her family piano in small town Arkansas. After moving to Nashville in 2011, she’s gone on to write for artists like Bethel Music, Leeland, We Are Messengers, Colton Dixon, Rachael Lampa, and Jordan St. Cyr, among many others.

Her work has also been featured across film and TV, including Love Is Blind, Teen Mom, Love Island, and more. As an artist, her project Ri-An has reached over 7 million streams on Spotify.

Rhyan shares how she got started, from writing songs as a child to moving to Nashville. She also opens up about the role mentorship played in her growth, as well as her journey through being a signed songwriter and being fully independent.

This episode is part of a session from the Christian Artist Mentorship. If you're interested in being a part of our next cohort, visit ChristianArtistMentorship.com⁠.

Let's Connect:

• ⁠Christian Artist Mentorship⁠ (Next Cohort Begins April 21)

• ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Wisdom Moon on Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

• ⁠Christian Artist Mentorship on Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

• ⁠Christian Music Marketing on Instagram⁠

• ⁠Pure Mosaic Services

Connect with Rhyan Shirley:

instagram.com/songsmith_coaching

songsmithcoaching.com