We were lucky to catch up with Jordan J. Stoute recently and have shared our conversation below.
Hi Jordan J., thank you so much for opening up with us about some important, but sometimes personal topics. One that really matters to us is overcoming Imposter Syndrome because we’ve seen how so many people are held back in life because of this and so we’d really appreciate hearing about how you overcame Imposter Syndrome.
I’m not sure I ever overcame it if I’m being honest. I struggle with it everyday and because I am a perfectionist, it’s always in the back of my mind that I’m not doing everything right. The good news about being on an entrepreneurial journey is that there are lots of right ways to go about it. There’s no one right way to work for yourself. It’s trial and error every day for me and I’m learning as I go. I think the most important focus as a business owner is to know exactly what niche you fit, to under-promise, and over-deliver. I find if I always focus on being authentically upfront with who I am, I align with the right clients. A big part of fighting imposter syndrome is to get out of thinking about yourself and more on thinking about how you can serve your clients. If I focus on results for them, everything naturally follows from there. It’s very empowering to learn to trust your own instincts and abilities. I’ve come to be proud of my “make it happen” skills. I find joy in being able to turn seemingly no leads into 2 show offers by the end of the week. The more I sharpen those skills, the more I trust myself to make results happen. The more connections I make, the less I have to grasp at straws to bring something to the table. I purposely made my business model to create accountability for myself because I am a month-to-month renewal. There’s no chance for me to become complacent because there’s no long-term contract for the artists. It keeps a fire under me to bring offers to the table. If there’s one thing I trust myself to do, it’s work well under pressure. When you’re thrown in a pressure cooker you don’t have time to wonder if you’re the right person for the job.

Appreciate the insights and wisdom. Before we dig deeper and ask you about the skills that matter and more, maybe you can tell our readers about yourself?
I find purpose in advocating for the indie scene because it’s full of hard-working, humble, and real people trying to make a dream happen. They are people who want bigger for themselves, to break out of the typical 9-5 matrix.
It’s brave, and because that world is so full of dreamers, there are snakes lurking around every corner, ready to take advantage. I’ve had it happen to me. I’ve seen it happen to others. I’ve learned exactly how not to run a business first-hand through previous work experience. Safe places in the industry are few and far between for independent artists, and I take great pride in choosing to make that my niche.
As a woman in the music industry, I also have a strong passion for supporting women in music. As a songwriter, recording artist, and performer myself, I know first-hand what it’s like to be the one singing for a free beer while no one listens, and I have experienced various instances of misogyny through the years. I love advocating for fair compensation and opportunity for all of my artists. I especially love it when I’m underestimated. It’s a superpower.
I want Jayebird Bookings to be known as an ally and advocate for every artist from every walk of life, especially those who are marginalized or stereotyped within the industry. If an artist keeps hitting walls while trying to pitch themselves, I aim to break through barriers to advocate for them, providing them with new opportunities that can further their career.

There is so much advice out there about all the different skills and qualities folks need to develop in order to succeed in today’s highly competitive environment and often it can feel overwhelming. So, if we had to break it down to just the three that matter most, which three skills or qualities would you focus on?
1. Adaptability.
When it comes to the music business and really any business venture, you have to learn to roll with the unexpected. Shows WILL be cancelled or double booked. The venue will forget to communicate an important piece of information. The artist will get sick. You’ll forget to respond to an email. Whatever the case may be, live shows come with an element of surprise and if you are doing your job correctly, negative experiences won’t happen often, but they will for sure still happen. You have to learn how to fix issues on the spot, and what you can’t fix, you use as a learning opportunity to become better and never repeat the same mistake.
2. Accountability.
Take responsibility for what you can control. When you mess up, do what you can to make it right. The music business is a relationship first world and how you treat people matters. It matters in any industry, but I’m just speaking on what I’m familiar with. Do what you’ll say you’ll do, and if you fall short, make it right. Never let anyone walk away from working with you feeling worse than they did before they met you. The unexpected is bound to happen, sometimes deals fall through, or results aren’t everything an artist hopes for. The key is to always be communicative, honest, take feedback seriously, and own your part in successes and failures equally. This is how you continue to grow.
3. Proactiveness.
I do my very best to be extremely proactive in everything I do rather than reactive. I try to mitigate issues or concerns before they ever happen. This includes being organized on my end and making sure I’m handling my business swiftly and professionally. I’ve found 99% of problems never happen if you ask the right questions and clarify pertinent information upfront with venues and artists. Communication is so important to make sure everyone is on the same page and everyone has an amazing experience. If you do not communicate effectively, expectations and results can be mismatched and once that happens it’s very difficult to bounce back from.
My advice on gaining these skills is to just jump in and gain as much experience as you can within your field of choice. Half the battle of working in the music industry is learning how to mitigate problems before they arise and managing expectations for all involved. No grey area, be very clear on who is offering what, and who is committing to what. Know what the artist is walking into so that they are as prepared as they can possibly be the night of their performance and so the venue invites them back. The goal is to create symbiotic partnerships that last as long as they are beneficial to all parties!

Before we go, any advice you can share with people who are feeling overwhelmed?
Get out of your head and into your body. I recently moved to a walkable community, and focus on hitting 10k steps a day and getting sun when I can. Yoga helps me as well to reconnect my brain and body and be more calmly focused as I’m working rather than a squirrel who just took a shot of espresso. Priority lists also help me greatly, I just go down them one at a time and check them off as I complete. I try to create small goals for the day and this in turn allows me to check off the main goals I need to make happen at the end of the month for each of my clients. What’s the saying? You eat an elephant one bite at a time. I also try to look at the bigger picture constantly and make sure I am aiming to hit my basic standards of service for each client. Most of my clients stay with me a minimum of 3 months, and since opening in September of 2023, I have had people stay on with me for 6 Months up to 10 months at this point. When I do struggle with imposter syndrome, I remember that in this economy, most people don’t have money to throw down the drain every month. They continue with me month after month for a reason. I am very proud of the work I do, especially knowing there are larger agencies with multiple agents that talent can work with. It’s just me right now running this ship! For independent artists, it’s really impactful for them to have one-on-one attention. My goal is to have 10-15 clients by the end of this year. I’ve been sticking to 7-8 per month consistently. I’m ready to amp it up! I’m excited for what the future holds.
Contact Info:
- Website: https://jayebirdbookings.com
- Instagram: https://www.instagram.com/jayebirdbookings/
- Facebook: https://www.facebook.com/people/Jayebird-Bookings/61550753735015/?paipv=0&eav=AfbaOGwOz6qQeCKRHXxn_rw8islZAICpOflkzEdHt98pewc5hl1POhIRA6envlueJLA&_rdr
- Linkedin: https://www.linkedin.com/company/jayebirdbookings
- Twitter: https://twitter.com/jayemadisonband
- Youtube: https://www.youtube.com/watch?v=iG7KzC4qVpQ

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