We caught up with the brilliant and insightful Uncle Jesse a few weeks ago and have shared our conversation below.

Hi Uncle Jesse, thanks for joining us today. What’s been the most meaningful project you’ve worked on?

Playing weddings is always a special experience for us, but it’s even more meaningful when the couple has a personal connection to our band. There’s something incredibly powerful about knowing that our music played a role in their love story—even before their wedding day.

We’ve had the honor of performing for couples who first saw us together on a date when their relationship was just beginning. To go from being part of their early memories to playing on one of the most important days of their lives is truly humbling. It’s a full-circle moment, and we don’t take it lightly.

Moments like these remind us that music is more than just entertainment; it’s a soundtrack to people’s lives, their relationships, and their biggest milestones.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

Uncle Jesse was born from our shared love of the ‘90s and early 2000s music we grew up with. All five of us have been playing and performing since childhood, and forming the band became a way to keep that passion alive as adults. What started in 2018 as a side project has since become a major part of our lives. In the early days, we played just a few shows a month—now, we’re performing over 70 shows a year.

Our setlist is all about celebrating the best music of the 90s and early 2000s. You won’t hear us playing anything less than 15 years old—we’re here to spark nostalgia and bring back the memories of those iconic decades. Like an iPod shuffle, our shows feature a mix of genres—pop, rock, R&B, and country—ensuring there’s something for everyone to enjoy.

It’s been incredible to see our music resonate with so many more people than we ever imagined, and we’re excited to see where this journey takes us next.

How’d you build such a strong reputation within your market?

Consistently performing in front of live audiences has been the biggest factor in building our reputation. There’s nothing quite like people experiencing the Uncle Jesse energy firsthand—feeling the nostalgia, singing along to the songs they grew up with, and rocking out with us in the moment.

Live shows create a lasting impression in a way that no social media post or video ever could. The more we play, the more people talk about us, share their experiences, and bring their friends to the next show. Word of mouth has been huge in growing our fan base, and every performance is an opportunity to win over new fans and keep longtime supporters coming back.

Beyond just playing frequently, we focus on delivering a high-energy, fun, and interactive show that keeps people engaged from start to finish. Whether it’s throwing in unexpected mashups, getting the crowd involved, or just making sure everyone leaves with a smile, we aim to create an experience that people will remember and want to come back for. At the end of the day, building our reputation has been about showing up, giving it our all, and letting the music speak for itself.

We’d love to hear the story of how you built up your social media audience?

We’ve grown our social media presence organically by consistently sharing quality content over time. In the beginning, we regularly posted acoustic videos to introduce our music to new followers while also exploring songs beyond our live setlists. To keep our audience engaged, we’ve also incorporated fun interactive elements, like a ‘90s/’00s music bracket challenge and trivia games on Instagram.

Our biggest advice for anyone looking to build their presence: get creative in how you connect with your audience and focus on delivering content they truly value. And whatever you do—don’t buy followers. While it may be tempting to boost your numbers, it ultimately does more harm than good. The Instagram algorithm prioritizes engagement, and fake followers will only push you further from reaching the people who genuinely want to see your content. Growing an authentic audience takes patience and persistence, but the payoff is worth it.

Contact Info:

• Website: https://www.unclejessemusic.com
• Instagram: https://www.instagram.com/unclejessedc
• Facebook: https://www.facebook.com/unclejessemusic
• Youtube: https://www.youtube.com/channel/UCOZ-VMQAzFupwwg_BBqtbJw

Image Credits

Jessica Miller – Starry-Eyed Photography
Gary Corpuz – Zuproc Photography
Meredith White