Leigh Holt (Artist Manager) on What Actually Builds a Successful Artist

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