Bossing It: Why Company Culture Is Everything with Sydney Ferleger

Sydney is a strong stakeholder in advertising, branded content and entertainment.

She is the president and executive producer running three successful companies: The Music Playground, The Diner, and The Station. Sydney is an adept music industry leader with experience in original music creation, band and artist licensing, production music, and music supervision for advertising, television, and film. She even had the pleasure of singing on a broadcast McDonald's commercial. At The Station she produces full-service projects, from creative ideation through finishing. She has an expansive knowledge of executing live-action and still photography productions with a focus in commercial advertising and branded content. She has worked on projects spanning from traditional advertising and branded content to virtual reality and experiential and has led international teams working with brands such as Amazon, Pepsi, and Puma, to name a few. Sydney is an active member of the Rolling Stone Culture Council, has been a Telly Awards judge for the past three years, and gives guest lectures on sync licensing at Universities and music conferences. When she’s not busy working, you can find her rocking out at a concert or hitting the slopes on her snowboard.

LBB> What was your first experience of leadership?

Sydney> In high school I was nominated to be part of a program that promoted safe driving. It was called 'Keep the Drive, Stay Alive' and the intent was to teach lessons about why one shouldn’t text and drive, etc. We were too young for the “don’t drink and drive” conversations, but that was certainly implied in one way or another. I was 16. It was the first time that I was part of a leadership program where the impact of the messaging could have a greater effect on society. I led my team on different projects and initiatives to help promote the message to the general public and to find unique ways to get the word out to our local communities. I wrote a song that, to this day, still gets stuck in my head sometimes.

LBB> How did you figure out what kind of leader you wanted to be – or what kind of leader you didn’t want to be?

Sydney> Two things: 

Role models

Practice makes perfect

I’ve had some great role models and mentors. People I look up to, people who helped me get to where I am today, people who really influenced me and made me want to be better, want to be like them. Bosses who made a difference, who cared, and who believed in me. It’s these types of people that resonate with me the most. Their passion and dedication is inspiring. If I could learn to support others in the way that these people have supported me, maybe I could make a real difference in someone’s life or career. Maybe I could be the inspiration for someone else. I have also experienced what it feels like to work with someone that is the opposite of a role model; someone who provides no guidance, no support, no collaboration, and is hard to work with and/or always unavailable. It can be miserable trying to get anything done in this type of toxic environment. I learned very quickly which of those two people I wanted to be. I want to be the type of leader that people are excited to share good news with, but also aren’t afraid to approach when something is wrong or they need help. To me, these are the leaders that stand out above the rest. 

Above all else, you learn as you go. Unfortunately, the biggest lessons happen when something goes wrong. It’s your reaction and dedication to making it better for next time that make all the difference. Learn from your mistakes, grow into your leadership, and own it.

LBB> What experience or moment gave you your biggest lesson in leadership?

Sydney> A very tough and uncomfortable employee situation. We hired a new employee and I noticed that certain tasks that were being asked of this person were being completely ignored. There was no follow up as to why these things weren’t getting done and when we asked point blank why these tasks were being disregarded our inquiries were met with some serious attitude. It’s easy to pick a fight. It’s harder to be the boss (or at least the version of 'the boss' that I strive to be) and to get to the bottom of why these tasks were being ignored. What I learned from this situation is patience and the power of actionable solutions. We can assume the worst in people or we can do the work necessary to make a better working environment. This doesn’t mean you have to be “mister nice guy.” We all need a little tough love here and there. What it does mean, and what I learned, is that with respect and open dialogue you can get to the bottom of an issue in a professional manner and come out of it with genuine, executable resolve. 

LBB> Did you know you always wanted to take on a leadership role? If so how did you work towards it and if not, when did you start realising that you had it in you?

Sydney> I always wanted to be a producer and becoming an EP was a dream come true. That being said, I was not thinking about the leadership side of the role. So my immediate answer is ‘definitely not!’ Here’s the story - A studio manager that I had hired was leaving the company for another great opportunity that was presented to her (good for her, all good things, well deserved). When she left she wrote me a letter, this is what it said, “You are literally the first woman to show me what confidence can really look like. Like how sometimes you need to stand up for yourself, even if it’s hard. It opened my world.” That was it, that was the moment. 

LBB> When it comes to 'leadership' as a skill, how much do you think is a natural part of personality, how much can be taught and learned?

Sydney> I do believe that people are born leaders. That it’s innate. I don’t think everyone can do it, or at least do it well (the way I believe it was meant to be done). Some people just don’t prefer it, don’t want the pressure that comes with it and that is ok. “Heavy is the head that wears the crown,” they say (a nod to Shakespeare). It takes a lot of courage, focus, energy, and discipline. I do think it can be taught, but even then, I think it has to be a part of your natural personality in one way or another. Although I’m sure there are exceptions to that, I’m not sure how much or how little really matters. You have to want it at the end of the day.

LBB> What are the aspects of leadership that you find most personally challenging? And how do you work through them?

Sydney> Prioritising needs. Understanding what my needs are vs everyone else’s and learning how and when to prioritise one over the other. Or simply learning how to properly and efficiently manage both at the same time. Being a leader means spending a lot of time engaging with other people in the company, i.e. my team. I often find myself managing their needs, requests, etc. over my own. I truly believe that you are only as strong as your team and that my job is to make sure that my team has whatever it is they need to be successful because, in turn, I and the companies are subsequently successful. However, sometimes this comes at the expense of my own time and needs. So, I have really been working through preserving my energy and organisation so that all needs can and are being met in a timely fashion and to the best of my ability. Working through and understanding what is most important to myself, my team, and the business and then moving on to the next while ensuring that even if it takes longer than we’d like, nothing goes unattended.

LBB> Have you ever felt like you've failed whilst in charge? How did you address the issue and what did you learn from it?

Sydney> Of course. We all fail, it’s one of the best ways we learn how to grow. Don’t ever let someone try to tell you otherwise. I address everything head on. I am honest (to a fault) and not afraid to have hard conversations. What I’ve learned in these moments is that it’s important to understand what information is important to the situation and what information is not. I’ve also learned to trust my gut instincts and lead with authenticity. I admit when I am wrong. How can my team feel comfortable admitting to and learning from their mistakes if their leader cannot? We should learn and grow together. 

LBB> In terms of leadership and openness, what’s your approach there? Do you think it’s important to be as transparent as possible in the service of being authentic? Or is there a value in being careful and considered?

Sydney> This ties in perfectly with my previous answer. I believe there’s a strong value in being careful and considered. Not all information is good or necessary. I think candour and transparency is important, but too much information can muddle the conversation and/or situation and doesn’t necessarily add any relative worth. I don’t believe this means that you are losing or devaluing authenticity in any way, you’re just being succinct and straightforward. Be concise, get to the point, and move on to the next. 

LBB> As you developed your leadership skills did you have a mentor, if so who were/are they and what have you learned? And on the flip side, do you mentor any aspiring leaders and how do you approach that relationship?

Sydney> Two people that stand out to me the most as true mentors in my professional life are Allison Cantor and Andrew Stadelberger. Allison was my boss when I was at Animated Storyboards. She was organised and smart; she taught me how to stay organised, how to focus, how to properly work with a CRM system, and how to be a strong woman in this game. I looked up to her in every way and I wrote her a letter when I left that company like the one that my studio manager wrote for me. Andrew is my predecessor at The Music Playground and The Diner. He hired me and he mentored me until the very end of his time with us at these companies. He taught me how to be a compassionate leader, what working hard really looks like, and when/how to stand up for myself. We made a great team.

I’m not sure I have one human that I necessarily mentor quite so intentionally, but I hope I’ve been able to teach, help, and inspire the people I work closest with. To that effect, I love teaching. I’ve been a Guest Lecturer at the Roc Nation School of Music, Sports & Entertainment for the past three years, I gave a Master Class on Sync Licensing in September at the IMSTA FESTA music conference and I’m a mentor for a mentorship program called Cutter Connections that is designed to unite professional women in advertising, entertainment, and digital media. I approach all of this with a genuine attitude that there is no greater feeling than paying it forward.

LBB> It's been a really challenging few years - and that's an understatement. How do you lead a team out the other side of a difficult period?

Sydney> 2023 has been our comeback year and the energy has been vibrant. In my opinion the best way to lead has been with honesty and intention. Your team needs to be fuelled, excited and motivated. Especially during the tough times, because that’s when it really is much harder to get the job done. Covid sucked for all of us. For me, it was about my team knowing that they have support during the toughest of times and that we would work through the chaos together and come out better for it in the end. And we have.

LBB> What are some ambitions and plans you have for the company and yourself in the coming year?

Sydney> We have some really exciting projects in the works, most of which I can’t reveal yet. But they are big, ambitious partnerships and I can’t wait to share them with you. We are also expanding. We’ve opened up a new arm out of Mexico City, which finally puts us boots on the ground in an international territory. We plan to continue to grow and expand further into other international territories. 

Personally, I love the music supervision and clearance work. We’ve done a handful of celebrity clearance projects since I started and I’d love to see more of those opportunities and projects come in so I can delve deeper into the intricacies and nuances of the licensing space. I also want to start performing live again and creating my own music. I haven’t found the motivation or time to jump back into my personal music projects since the world shut down and I think it’s about time I finally did.

LBB> What have you noticed as the biggest changes in the industry during your career thus far? And do you have any predictions for future trends or themes?

Sydney> Budgets keep getting smaller. 

In-house, direct-to-brand work is increasing.

Advancing technologies are changing the game and the way we do our jobs. Right now it’s AI. 

Social media has changed the marketing landscape (TikTok did a number on us all).

I don’t think AI will take our jobs (not all of them anyhow). I think it will change the way we work and the roles we play. There is a human behind the machine. 

LBB> How important is your company culture to the success of your business?

Sydney> Company culture is everything. If people are unhappy or uncomfortable, business suffers. 

LBB> What are the most useful resources you’ve found to help you along your leadership journey?

Sydney> The ‘Bossing it’ LBB series is a great place to start. Some really inspiring people have been interviewed here. Thank you for having me. 

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