Know your strengths and delegate: In the early days, I made the mistake of trying to do everything myself. I was the marketer, the manager, the performer, the bookkeeper — you name it. I quickly realized that this wasn’t sustainable. If you want to scale, you can’t wear every hat. Instead, I recommend writing a “Do List” list and a “Don’t” list. Over time, eliminate the tasks that don’t align with your strengths, and delegate those to others. Invest in yourself, your time, and your business. It will pay off. Focusing on what you do best will allow you to scale more effectively and keep your business on track for growth.
Startups usually start with a small cohort of close colleagues. But what happens when you add a bunch of new people into this close cohort? How do you maintain the company culture? In addition, what is needed to successfully scale a business to increase market share or to increase offerings? How can a small startup grow successfully to a midsize and then large company? To address these questions, we are talking to successful business leaders who can share stories and insights from their experiences about the “5 Things You Need To Know To Successfully Scale Your Business”. As a part of this series, we had the distinct pleasure of interviewing Jamie Kolnick.
Jamie Kolnick is the Founder and CEO of Jam with Jamie, a national children’s music entertainment and education company that has delighted families for over 16 years with high-energy performances. Founded in NYC in 2008 and now based in Miami, the company has grown to over 80 performers in 11 cities. Jamie also created Little Jam Fest, an annual Miami-based family music festival launched in 2024. A performer, entrepreneur, and community builder, Jamie co-founded the Epstein Reach for the Stars Scholarship Foundation, supporting South Florida students since 1998. She shares her personal journey through essays and podcasts and lives in Miami with her husband and three children.
Thank you for joining us in this interview series. Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’?
Ofcourse and thanks so much for having me! I currently live in my hometown of Miami with my husband, Shaun, and our three kids: Zach (9), Evan (7), and Zoey (3). Growing up in a household of five, family has always been the most meaningful part of my life. It’s my number one priority, and it deeply shapes who I am today.
To give you some context, my childhood was everything you could wish for: a beautiful home, great schools, and an abundance of friends. I had two brothers who constantly picked on me but loved me, and parents who were my biggest supporters. However, in 1998, my world changed dramatically when my brother Alan tragically passed away in a car accident. At 13 years old, I had no idea how to navigate such profound grief. My way of coping was through my creativity, particularly music, which has always been a driving force in my life. I channeled my emotions into writing — songs, journals, and words upon words — hoping to process the immense pain of losing my oldest brother, someone I looked up to and admired.
Music has always been at the core of who I am, and naturally, it became central to my career. I attended the University of Texas at Austin, where, during my sophomore year, I lost my father to leukemia. Meanwhile by this point, my mother had been battling breast cancer for over 10 years. These experiences taught me about grief in ways I never could have anticipated, and I coped by throwing myself into the vibrant, fast-paced life at the university. I graduated with a B.A. in theater, and after graduation, I moved to New York City with my husband, Shaun, to pursue my dream of Broadway. I immersed myself in acting classes, voice lessons, songwriting forums, and countless auditions — enduring rejection after rejection, but also receiving those cherished “yes” moments. These experiences taught me one of the most important life lessons: not to take rejection personally.
While in NYC, I also began teaching music to babies at a private members-only club in Soho. It was a surreal experience to teach children of celebrities like Gwyneth Paltrow and Christy Turlington. My mother, always my biggest cheerleader, encouraged me to take the leap and start my own business. This led to the creation of “Jam with Jamie.” Five months after launching, my mother passed away after a 15-year battle with breast cancer. Though she is no longer with us, her legacy continues to guide me every single day.
I call myself an “accidental entrepreneur.” What started as a fun side gig blossomed into a nationwide children’s music company. Today, we bring joy and music to families across the country, with 100 talented performers leading the way. It’s been quite the journey and one I’m incredibly grateful for.
You’ve had a remarkable career journey. Can you highlight a key decision in your career that helped you get to where you are today?
A key decision in my career came when my mom’s health was declining, and my business was growing. I realized I didn’t need to be at every event and could build a team to help run the business. Up until that point, I had done everything myself, but the idea of hiring and training other performers was both daunting and exciting. I hired my first independent contractor, and once their first party went off without a hitch, I knew this was the right direction.
Our growth was gradual at first — just four performers in the first year, then 10 in our second year — but it quickly accelerated. Now, we have 100 performers in 12 cities. That moment, born out of necessity, ended up being a game-changer for the business. My mom always said that every challenge can lead to a positive outcome, and this shift from doing everything myself to trusting others was a key moment in our success.
What’s the most impactful initiative you’ve led that you’re particularly proud of?
In 2020, when the pandemic hit, small businesses, including ours, were forced to rethink everything. Families were at home, and we quickly pivoted to offer complimentary virtual jams and birthday parties. While I knew it wouldn’t generate immediate revenue, it felt like the right thing to do. It gave our performers a sense of purpose during such a tough time, and we accepted donations on their behalf for the work they were doing.
Looking back, it was one of my favorite times running the business. There was no agenda — just a genuine desire to help families. And the impact was incredible. We gained over 7,000 Instagram followers, were featured in multiple press outlets, and brought joy to families worldwide. What started as a goodwill initiative eventually led to brand collaborations, new partnerships, and even a new homeschooling program that became a revenue stream. It’s a perfect example of how leading with your heart can ultimately drive success.
Sometimes our mistakes can be our greatest teachers. Can you share a mistake you’ve made and the lesson you took away from it?
When I first began scaling beyond NYC, I let excitement drive my decisions rather than strategy. I underestimated the work that needed to be done in each location and expanded too quickly without fully considering the press and local support needed in each new state to effectively back up the growing team. As a result, we struggled to book parties with such a small team in multiple locations. Eventually, I paused the expansion to focus on strengthening the states we were already in, and though there’s still work to be done, we’ve made incredible progress.
The biggest lesson I learned was the importance of mastering your initial market before expanding. My advice is to build a solid foundation — partner with local businesses and prove your concept fully before expanding. Understanding your capacity in one area gives you the insight to scale wisely. Focus is key, and it’s important not to get distracted by the allure of new locations or revenue streams until your core operations are running smoothly.
How has mentorship played a role in your career, whether receiving mentorship or offering it to others?
I truly wouldn’t be where I am today without the incredible mentors who’ve supported and guided me. To put it simply, I graduated from UT Austin with a degree in theater — not business! Building and scaling a successful company, and ensuring its longevity, has only been possible because of the wisdom and guidance I’ve received from my mentors.
One key mentor, Antoinette Beauchamp, founder of AB Coached, taught me the importance of self-care. She helped me realize that in order to take care of my business and others, I had to prioritize myself and eliminate what no longer served me, both personally and professionally. Her advice was life-changing, and it gave me the clarity and confidence to be unapologetic about my choices and my time.
Another mentor, Carissa Reiniger of Small Biz Silver Lining, continues to play a pivotal role in reshaping how I run my business. She helped me completely overhaul my approach and identify the key players needed in each sector of my business to reach my goals. Her guidance on strategic growth and understanding how to transform my dream into a tangible reality has been invaluable.
Now, I’m proud to pay it forward. Mentorship is something I deeply believe in, and I make it a point to offer support to others who are on their own entrepreneurial journeys.
Developing your leadership style takes time and practice. Who do you model your leadership style after? What are some key character traits you try to emulate?
My leadership style is grounded in collaboration and creating an environment where everyone thrives. It’s a style that has evolved through experience and learning from others. I’ve attended several conferences and panels, where I’ve had the opportunity to listen to successful founders and understand how they balance power with team dynamics. From these experiences, I’ve learned the importance of hiring the right people, addressing pain points early, and making decisions collaboratively with my executive team.
One leader who deeply inspires me is Sara Blakely, the founder of Spanx. I admire her ability to lead with joy, passion, and authenticity. She’s not only a strategic and innovative thinker, but also someone who is deeply invested in her team and community. She embodies the qualities of intuition, empathy, and a strong work ethic — traits I strive to bring into my own leadership. Like Sara, I believe in leading with heart, and I make it a priority to support and uplift those around me, ensuring we’re all aligned toward shared goals.
Thank you for sharing that with us. Let’s talk about scaling a business from a small startup to a midsize and then large company. Based on your experience, can you share with our readers the “5 Things You Need To Know To Successfully Scale Your Business”? Please give a story or example for each.
1. Know your strengths and delegate: In the early days, I made the mistake of trying to do everything myself. I was the marketer, the manager, the performer, the bookkeeper — you name it. I quickly realized that this wasn’t sustainable. If you want to scale, you can’t wear every hat. Instead, I recommend writing a “Do List” list and a “Don’t” list. Over time, eliminate the tasks that don’t align with your strengths, and delegate those to others. Invest in yourself, your time, and your business. It will pay off. Focusing on what you do best will allow you to scale more effectively and keep your business on track for growth.
2. Have a mentor: You would be surprised about how many people in your industry are willing to speak to you about business. Some of these conversations will come with a price (pay it), and some will not. But these conversations are invaluable and could lead to a leadership coach. Especially as someone who was not planning to grow the business to the scale that it is now, it has been imperative for me to have incredible mentors. Do the outreach and the time to find people who will support you!
3. Scale Intentionally: When I first started scaling my business, I was fueled by excitement and passion. Performers were reaching out to me from various cities, eager to learn from me, and I saw this as an opportunity to scale. I took them on, expanded quickly even though I didn’t have the proper infrastructure in place to support them. I quickly realized that scaling too fast without the right strategy can lead to many challenges. Focus where you start, outgrow your primary location and then expand.
4. Hire Slow, Fire Fast: One of my biggest mistakes early on was hiring simply to fill an immediate need, rather than taking the time to find the best fit. I’ve learned that it’s essential to hire people who are not only capable but who will elevate your business. When I hired hastily, I ended up with team members who didn’t align with our culture or the quality we were striving for, leading to dissatisfied clients and internal frustration. I now make sure to hire thoughtfully and, if someone isn’t working out, I don’t hesitate to part ways quickly. It’s better to have a smaller, stronger team even if you can’t meet demand than a large one that’s not a good fit.
5. Be Creative with Outreach: While working with PR companies has absolutely been valuable at key moments in growing my business, shoutout to Wynn and Jade PR! I’ve learned that a large press budget isn’t always necessary or available to gain attention and drive growth. Early on, I took a grassroots approach to PR by partnering with local influencers in cities where we were expanding, offering services in exchange for social media exposure. I also actively engaged with online communities, joining mom groups and commenting on articles related to our industry.
To this day, I continue to engage in direct outreach — whether it’s pitching myself as a podcast guest, collaborating with brands and influencers via DMs, networking at conferences, connecting and posting on LinkedIn, and leveraging every opportunity to get my business in front of new audiences. As the founder, you are the most passionate and knowledgeable advocate for your brand, and you can make a real impact by consistently promoting it in authentic, creative ways.
Can you share a few of the mistakes that companies make when they try to scale a business? What would you suggest to address those errors?
1 . Scaling Too Quickly
One of the biggest mistakes? And one I have made! Trying to expand before you’re ready. It’s like trying to run a marathon without training — sure, you might make it, but you’re probably going to be gasping for air halfway through. If you rush into new markets or increase production without nailing what you’ve already got, things can get messy fast.
What to do: Focus on perfecting what’s working for you right now. Make sure your business model is solid and profitable in your current market before you leap into new territory. Think of it like getting your shoes tied before you start running. Make sure you hire a mentor or executive coach too!
2. Investing in the Proper Resources
Scaling often means big investments — and for most, that is very scary! Know what your budget is and how it should be allocated. Be very clear on what hire(s) are most important and what would be the most valuable for your business. It does not need to be all at once. Growth takes time. Rushing hires and bringing on too many people will set you back.
What to do: Make a thorough plan so you understand how to strategically get from A to Z. An executive coach can really help with this process and will be worth it!
3. Neglecting Company Culture
As you grow, it’s easy for company culture to get lost in the shuffle. But if you don’t keep that personal touch, you’ll end up with employees who feel more like robots than rockstars. A disengaged team can be a huge problem when you’re trying to scale.
What to do: Stay connected with your team and keep the culture strong. Have company outings. Even as you hire more people and expand, make sure you’re fostering a work environment that’s as positive and motivating as it was when you were just starting out. A happy team is a productive team — plus, it’s way more fun to work with happy people!
Scaling includes bringing new people into the organization. How can a company preserve its company culture and ethos when new people are brought in?
Be really intentional about who you hire. It’s not just about filling a role — it’s about finding people who align with your values and vision. I have a system in place for onboarding that ensures everyone understands what we stand for. During the onboarding process and ongoing, our executive team stays in close contact with new hires to make sure they feel supported and clear on our culture.
As a small team, we’re able to stay close-knit and approachable, which helps when issues arise. It’s important to us that our team members feel they can be transparent and open with us. We operate like a little family — respectful boundaries are key, and we always lead with love. When people feel safe, supported, and valued, they’ll not only thrive but truly enjoy what they do.
Many times, a key aspect of scaling your business is scaling your team’s knowledge and internal procedures. What tools or techniques have helped your teams be successful at scaling internally?
For us, continuous learning is key to success. We believe in being lifelong learners, and we want our team to feel the same way.
To support this, we offer ongoing educational courses online and in person to help our team members grow their skills and expand their expertise. We also make ourselves available for one-on-one sessions to discuss challenges and opportunities for improvement. Additionally, we create space for group rehearsals and training to foster collaboration and skill development.
We don’t want anyone on our team to feel stagnant — there’s always room for growth. That’s why we offer incentives and bonuses based on the value people bring to the business, whether it’s through their work or the way they show up to contribute to the team. At the end of the day, we want everyone to feel empowered to learn, grow, and thrive.
Because of your role, you are a person of significant influence. If you could inspire a movement that would bring the most amount of good to the most people, what would that be? You never know what your ideas can trigger.
Little Jam Fest, a family music festival in Miami that we recently produced for our second year in a row, has immense potential to become a powerful movement that brings communities together. Like any start up, it will take time to build, but I can absolutely see it expanding into an important part of our country’s music culture, creating a space where families and neighbors come together to celebrate music, creativity, and connection.
At its core, it’s about fostering a sense of unity and reminding people of the importance of shared experiences. It’s more than just a festival; it’s a chance for people to bond, uplift one another, connect with brands that will support their lives and create lasting memories.
How can our readers further follow your work online?
To stay up to date on my latest projects and events, please follow @Jamwithjamie , @jamiekolnick , and @littlejamfest on Instagram or visit www.jamwithjamie.com to book a class or party.
This was truly meaningful! Thank you so much for your time and for sharing your expertise!
