We were lucky to catch up with Bernard Scahill recently and have shared our conversation below.
Bernard, so great to be with you and I think a lot of folks are going to benefit from hearing your story and lessons and wisdom. Imposter Syndrome is something that we know how words to describe, but it’s something that has held people back forever and so we’re really interested to hear about your story and how you overcame imposter syndrome.
My journey from performer to business owner has been an incredible learning experience, especially in overcoming imposter syndrome. I started as a singer, performing in choirs, operas, and musical theatre through high school. My passion for singing & music led me to go to school for musical theatre performance and went on to work on National Tours & regional productions like Les Misérables, CATS, Jesus Christ Superstar, Beauty & the Beast, West Side Story and others.
During the pandemic, an unexpected opportunity arose. As a food and beverage manager at the Mondrian Park Ave in New York City, I was given the chance to program a few nights with my own concerts. Using my network of performer friends and industry contacts, I sold out these events, which became the foundation for my company, Concerts Under the Stars.
The real challenge came when I decided to expand the business to my hometown of Chicago. Suddenly, I was in meetings with marketing professionals, finance experts, and other business specialists – people who had formal education in their fields. As a performer turned entrepreneur, I found myself navigating unfamiliar territory, and that’s when imposter syndrome hit me hard.
I questioned whether I had the skills to run a national brand. The first two years were a steep learning curve, filled with moments of self-doubt. However, during a particularly challenging time, I had a realization that changed everything. I recognized that one of my greatest strengths as a performer – adaptability – was also a crucial asset in business.
To overcome imposter syndrome, I reminded myself that I had the confidence to start this venture in the first place. I trusted in my ability to figure things out and adapt to new situations. I also learned the importance of seeking out people who could help in areas where I lacked expertise.
The most valuable lesson I’ve learned is to trust in your initial instincts and surround yourself with knowledgeable individuals who can support your growth. Today, Concerts Under the Stars operates in over 14 U.S. cities, with plans to expand internationally. This journey has taught me that while imposter syndrome can be challenging, it’s also a sign of growth and stepping out of your comfort zone.
By embracing my unique background and leveraging my strengths, I’ve been able to turn a pandemic-born idea into a thriving business. It’s a reminder that our diverse experiences, even those seemingly unrelated to our current roles, can be our greatest assets in overcoming self-doubt and achieving success.”

Thanks, so before we move on maybe you can share a bit more about yourself?
Concerts Under the Stars is a unique rooftop concert company that I founded during the pandemic, born out of my background as a performer as well as working in the food and beverage industry. What we do is create unforgettable musical experiences in beautiful outdoor settings, typically on hotel rooftops or in charming outdoor spaces.
What’s most exciting about our concerts is the attention to detail we put into ensuring each guest has an exceptional experience. We carefully curate the atmosphere to complement the starlit evenings, and I personally approve the talent to guarantee stellar performances. Our shows aren’t just about the music – they’re immersive experiences where audiences might learn fascinating tidbits about the artists we’re paying tribute to, hopefully insights they may not already know!
We offer a diverse range of musical genres, from Sinatra to Queen to Taylor Swift. One of favorite titles of a concert is, ‘From Ella to Amy: A Tribute to Female Jazz Legends,’ which spans decades of incredible female jazz artists. This variety allows us to cater to different tastes and keep our offerings fresh and exciting.
What sets us apart is our commitment to creating a company by musicians, for musicians. This core mission has remained unchanged since our inception during the pandemic shutdown, when our goal was to create work for everyone in the industry. Today, even as we’ve expanded to over 14 cities across the US, we continue to prioritize providing opportunities for talented performers, and giving our audiences an experience they wont forget.
We’ve had some incredible milestones along the way. We were approached by Focus Features to produce an Amy Winehouse tribute concert in Seattle to promote the release of ‘Back to Black.’ We’ve also been featured on WGN News in Chicago, which was particularly meaningful given my family’s connection to the station. My Dad worked as a camera operator for the station for years, and all my family and friends in Chicago got to see my company featured on the news.
Looking ahead, we’re excited about our expansion plans. We aim to bring Concerts Under the Stars to Canada in 2025 and the UK shortly after. We’re also diversifying our offerings with immersive experiences, large party format events, and a new branch of the business that will bring our concerts to cruise ships, casinos, and theme parks.
One of our proudest achievements is the recognition we’ve received from venues themselves. They’ve started reaching out to us, asking to host our concerts after seeing our product elsewhere. This, along with the amazing submissions we receive from talented performers wanting to work with us, confirms that we’ve created something truly special.
At its heart, Concerts Under the Stars is about creating magical musical moments under the night sky, supporting musicians, and bringing joy to audiences. We’re excited to continue growing, innovating, and sharing our love of music with even more people around the world.”

If you had to pick three qualities that are most important to develop, which three would you say matter most?
Reflecting on my journey from performer to the founder of Concerts Under the Stars, I believe three key qualities were instrumental in my success:
1. Adaptability: As a performer, I was used to thinking on my feet and adjusting to new situations quickly. This skill proved invaluable when transitioning into business ownership, especially during the unpredictable times of the pandemic. Being able to pivot and see opportunities where others saw obstacles was crucial.
2. Networking: My background in the performing arts gave me a vast network of talented individuals. Leveraging these connections allowed me to quickly assemble high-quality performances when I first started the company. It also helped me navigate the business world as I expanded.
3. Passion for Creating Opportunities: My drive to create work for fellow artists during a challenging time for the industry became the foundation of our company’s mission. This passion not only motivated me but also resonated with others in the industry, helping to attract talent and partners.
For those early in their journey, here’s my advice on developing these qualities:
1. To improve adaptability, purposely put yourself in new situations. Take on diverse projects or roles, even if they’re outside your comfort zone. Each new experience will build your ability to think on your feet and find creative solutions.
2. For networking, remember that it’s about genuine connections, not just collecting contacts. Attend industry events, collaborate on projects, and always be willing to help others. Your network grows naturally when you’re known as someone who’s reliable and supportive.
3. To develop a driving passion, reflect on what truly motivates you beyond personal success. What change do you want to see in your industry or community? Let this guide your decisions and fuel your persistence when faced with challenges.
Remember, these skills aren’t developed overnight. They’re honed through experience, often in the face of setbacks. Embrace the learning process, stay curious, and don’t be afraid to take calculated risks. Your unique background and experiences, even those that seem unrelated to your goals, can become your greatest assets in unexpected ways.

We’ve all got limited resources, time, energy, focus etc – so if you had to choose between going all in on your strengths or working on areas where you aren’t as strong, what would you choose?
In my experience as the founder of Concerts Under the Stars, I’ve found that it’s generally better to go all in on our strengths while strategically addressing areas of weakness. Here’s why I feel this way:
Firstly, our strengths are often what set us apart and drive our success. In my case, my background in music and performance gave me a trained eye and ear for talent, which has been crucial in curating high-quality performances for our concerts. By leveraging these strengths, I’ve been able to create unique experiences that resonate with our audience and stand out in the market.
However, this doesn’t mean we should ignore our weaknesses. Instead, I believe in acknowledging them and finding strategic ways to address them. For me, this meant surrounding myself with a team of specialists who excel in areas where I lack expertise. This approach has allowed me to gain an ‘on-the-job education’ in various aspects of business while ensuring that the company benefits from top-tier skills in every department.
I learned the importance of this balance the hard way. Early on, I tried to wear every hat in the company, attempting to be well-rounded by handling every aspect of the business myself. This approach quickly proved unsustainable. The breakthrough came when I shifted focus to my strengths and brought in a team to handle everything else. This not only made the operation more efficient, but also expanded our capabilities and ideas.
In hiring, I consistently look for people who are passionate about what they do. I’ve found that a team of dedicated experts, each focusing on their strengths, is more effective than trying to do everything alone.
That said, I believe there’s one area where being well-rounded is crucial: adaptability. The ability to adapt to new situations, pivot when necessary, and learn from those around you is invaluable. This is a strength I’m proud of and one I think everyone should cultivate.
My advice for others would be this: Identify your core strengths and lean into them. These are likely the skills that will set you apart and drive your success. At the same time, be honest about your weaknesses. Rather than trying to become an expert in everything, surround yourself with people who excel in areas where you don’t. Be open to learning from them, but don’t let the pursuit of being well-rounded distract you from maximizing your unique talents.
Remember, in the arts and in business, what often matters most is having a clear point of view and the ability to execute it well. Focus on developing that clarity in your strengths, and you’ll likely find greater success than if you spread yourself thin trying to be good at everything.”
Contact Info:
- Website: https://www.concertsunderthestars.com
- Instagram: https://www.instagram.com/concertsunderthestars
- Facebook: https://www.facebook.com/OutdoorConcertsUnderTheStars
- Linkedin: https://www.linkedin.com/in/bernardscahill042a25239




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