Bootleg: Beyond The Setlist. To Raise Or Not TO Raise
Notes on live music, connection, and the emerging future, by Bootleg founder and CEO Rod Yancy
🎤 Sound Check
Entrepreneurship is a game of problem-solving. Some problems keep you up at night, feeling heavy and at times insurmountable. Others you’re grateful to have because they signal growth, momentum, and new possibilities for the company.
Right now, I’m focused on one of the good ones: should I raise outside capital for Bootleg, or keep bootstrapping it myself?
Historically, I’ve built and scaled companies without outside capital, funding growth of Oath Law and Oath Planning from the proceeds of the business itself. That approach has its advantages and has served me well.
But with Bootleg, I find myself wondering if the way to unlock its full potential is to build in a way I’ve never built before.
Naval Ravikant talks about different kinds of leverage, the tools that let you do more than you could manage alone. Things like building teams of talented people, telling your story through media, or creating code to make work more efficient are all things I’ve intentionally tapped into throughout my journey as an entrepreneur. The last one he talks about is capital and, for better or worse, I’ve never tapped outside investment to accelerate growth.
Part of me likes that. You move at a deliberate pace, you stay fully in control of the vision, and you sharpen the skill of building with creativity and discipline. But another part of me wonders if we’re leaving opportunities on the table by not inviting the partners in, or missing chances to move faster when the window is open.
We’ve got a lot going for us right now. Music is culturally relevant, and our story is resonating with both industry veterans and outsiders. We’ve already had conversations with potential investors who offer more than a check: they bring connections, experience, and what feels like a world of possibility.
I’m grateful to be in the position to wrestle with this kind of dilemma. While I have an affinity for bootstrapping, I remain open and curious about what could happen if we paired our ability to scale efficiently with partners who see the vision and want to help bring it to life.
Maybe the question of “to raise or not to raise” is not one you answer philosophically. Maybe, like all of life’s meaningful relationships, it comes down to the right person arriving at the right time and something just naturally clicking into place.
If you’ve navigated this crossroads, I’d love to hear what guided your decision.
⚡️ Live Wire
The industry’s moving fast. I’m just trying to stay tuned in, and share what I hear along the way.
🌍 Live Nation’s Q2 Boom
Live Nation’s latest earnings show concerts revenue up 19% year-over-year, despite putting on fewer shows. The growth is being driven by strategic touring, higher per-show impact, and surging demand across Europe, Asia-Pacific, and Latin America. It’s a clear reminder that the future of music is global, and artists everywhere are playing to some of the most engaged audiences in history. Bootleg is a way for those artists to do even better, turning the shows they’re already playing into lasting, shareable recordings that generate new revenue long after the encore.
👉Read the full story at Music Business Worldwide
🎛 ElevenLabs AI Announcement
If you follow music news, it's starting to feel like every other headline is about AI. This week it was ElevenLabs’ announcing a new AI tool, Eleven Music, that can produce polished songs from plain-English prompts complete with vocals, genre control, and full commercial rights. They’ve partnered with Merlin and Kobalt to share revenue and added safeguards against obvious misuse. We’re watching moves like this closely. On one hand, it’s encouraging to see licensing and artist compensation built in from the start. On the other, it raises deeper questions about authorship, cultural nuance, and what happens when machine-made music floods the market. At Bootleg, we believe in celebrating and monetizing what’s already alive on stage. The only music that’s unquestionably human? Live music.
👉Read more at Digital Music News
🎟️ Backstage Pass
At Bootleg, we help artists capture and sell high-quality audio recordings and photographs from their shows so fans can collect and relive the moment, and artists can keep earning beyond the encore.
What’s Moving
Speaking of the future of music being global, this week marks Bootleg’s first foray into international markets as we launch tours in Europe with two exciting emerging artists.
First up is Chris Renzema, bringing his soulful, spiritual singer-songwriter energy to stages across the UK. And this Saturday, we kick off with longtime Bootlegger Evan Honer, joining him for dates in Ireland, Scotland, England, the Netherlands, and Germany.
Expanding our product into new countries is no small feat, and I’m proud of our team for moving quickly to ensure we can execute our mission anywhere in the world. It’s a milestone that not only opens new doors for Bootleg, but also for the artists we serve and the fans we connect them with.
🎵 Fade Out
The question of whether to raise outside capital isn’t abstract for me, it’s about what kind of company we want to be as we grow.
This week we step onto stages in new countries for the first time, proving that what we’ve built works anywhere in the world.
That’s exciting, and it’s also a reminder that the right resources at the right time could help us bring this to more artists, more fans, and more places, faster.
However we decide to get there, the mission stays the same: capture the moments that make live music unforgettable, and make them available to anyone, anywhere.
With gratitude,
Founder & CEO, Bootleg.live