This week on the New Music Business podcast, Ari sits down with Jaclyn O’Connell, a digital marketer, creative strategist, artist manager, and founder of Bittersweet Media and Good Grief Management. Jaclyn has provided creative marketing solutions and hands-on artist management for artists and labels of all scales and sizes—from emerging artists to well-established acts and both indie and major labels. They have supported gold and platinum records and worked with artists including Wild Rivers, Cavetown, Julian Baker, and Cold War Kids. Drawing on experience in both marketing and artist management, Jaclyn offers a sharp, insider perspective on what it truly takes to build a sustainable career in today’s music industry.

In this episode, Ari and Jaclyn dive deep into the realities of modern music marketing — from navigating ever-shifting social media algorithms to building effective fan funnels that turn casual listeners into ticket buyers and lifelong fans. They also unpack the current touring landscape, direct support deals, and the hot-button issue of tour buy-ons. Whether you're an artist, manager, or just curious about how fan engagement really works, this is a conversation you won’t want to miss.

Chapters

00:00 Building Direct Relationships with Fans

03:09 Navigating the Social Media Landscape

05:49 The Importance of Mental Health in Artist Management

09:05 Innovative Monetization Strategies for Artists

11:55 The Role of Community in Artist Growth

14:58 Understanding the Fan Journey

18:05 Challenges in Touring for Emerging Artists

21:03 The Evolution of the Live Music Industry

36:21 The Ethics of Tour Buy-Ons

39:09 Navigating the Challenges of Touring

43:05 Building Artist Relationships and Mental Health

46:04 Defining Success in Artist Campaigns

48:02 The Role of Social Media in Driving Streams

51:01 The Nuances of Going Viral

55:29 The Fragmentation of Viral Success

57:23 Conversations with Labels and Ownership

01:01:23 Balancing Management and Business

01:10:25 Setting Boundaries in Artist Management

Edited and mixed by Ari Davids

Music by Brassroots District

Produced by the team at Ari’s Take

Order the THIRD EDITION of How to Make It in the New Music Business: https://book.aristake.com

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E48: The biggest limiting belief that is holding you back from rising into your power