Introduction: A Legacy of Entrepreneurial Growth
Host (David Martin): Jen Hickle, thank you so much for being on the podcast today. We have been friends for a long time, and I was so excited when you agreed to be here. You have been in business for over 25 years and coaching small businesses for about a decade. You built the Rogers School of Music in Minnesota into a seven-figure business using systems and marketing before eventually selling it. You also founded the Never Alone Coaching Program and the VA Academy, which trains virtual assistants and supports business owners with systems and messaging. You’re an author of Happy Kids Growing Biz and have studied everything from Myers-Briggs to CliftonStrengths.
Guest (Jen Hickle): I love being on podcasts and I’ve loved our friendship over the years. As entrepreneurs, we should always be learning.
The Trajectory of a High School Piano Teacher
Host (David Martin): Let’s go back to when you first started your music school. What was that like?
Guest (Jen Hickle): I was a senior in high school when a neighbor asked me to teach their kid piano. I asked my own piano teacher if he thought I could do it, and thankfully he said yes, because that changed the trajectory of my life. My mom realized this could help pay for college, so she put up flyers in the teachers’ lounge of the small Christian school where she taught. I started with three students on Saturday mornings. I instantly loved not only the teaching but the admin, tracking payments, and staying organized.
Guest (Jen Hickle): By that fall, I had 10 students, and my mom mapped out how much I needed to charge to make my college tuition payments. I taught throughout college, coming home on weekends to teach at my parents’ house and going to that same Christian school during the week so kids could have lessons during the school day. Other students asked how I found so many clients, and I realized I could hire them to teach the students on my waiting list.
Scaling Too Fast: The First Major Business Pivot
Guest (Jen Hickle): I was 22, married, and a new mom, and I realized I could run the business from my computer. In the first five years, I scaled very quickly to 10 teachers, but I scaled too quickly. I had three babies and was overwhelmed with parent complaints and miscommunications. One day I decided enough was enough and raised tuition drastically, from $60 to $85 a month. Some parents quit, but I made more money and had fewer complaints from people who didn’t see the value. That allowed me to get to the next level. To scale, you have to delegate and have repetitive systems rather than just putting out fires.
Hustle, Marketing, and Solving Problems
Host (David Martin): How did you grow so quickly before the age of Google and social media?
Guest (Jen Hickle): I just hustled. I put up yard signs in my neighborhood and paid my teenage sister to put flyers in mailboxes. What really set me apart was our competitor, Schmidt Music. They would just hand parents a list of names and numbers to call. I wanted to be a clearinghouse where I matched students to the right teacher based on personality and learning styles.
Guest (Jen Hickle): We drove to students’ homes, which meant less overhead. I also focused on professionalism and excellence. I did a full-color newsletter with every mailed invoice because it made the parents like me more; I provided practice tips and made myself relatable. I also handled book purchasing so parents didn’t have to. I stayed in a small geographic radius so my teachers wouldn’t burn out in traffic. I even limited enrollment to August, requiring a full-year commitment. I’m a natural marketer, so I leaned into solving problems and staying organized.
Moving into Commercial Space and Systems
Host (David Martin): When did you realize you needed admin help?
Guest (Jen Hickle): In 2008, when the economy crashed and my dad lost his job, I wanted to help. I found a fitness place to rent during the day so my parents could offer theater classes while I handled the admin and marketing. That’s when I started drowning in details. A woman opening a ballet school asked if I wanted to rent the back half of her building. I subleased from her but didn’t put my name on the building because I was actually scared of growing too fast while homeschooling four kids.
Guest (Jen Hickle): Once I had a set rent, I knew the stakes were high. A neighbor suggested I put a sign in the window, and once I put up big vinyl letters for “Piano, Guitar, Voice,” the phone started ringing off the hook. I got enrollment software, started offering choirs and art classes, and realized I needed a front desk person. I hired my first admin, Cassie, and it was like angels singing because she could enroll students while I focused on marketing and expansion.
The Importance of SOPs and Early Delegation
Host (David Martin): Did you give your first admin guidance or did she have to figure it out?
Guest (Jen Hickle): I cranked out all her Standard Operating Procedures (SOPs) in a week. I wrote an entire operations manual, FAQs, and enrollment instructions. Most people aren’t wired like me; they won’t hire until systems are done. But assistants are often wired to create systems. My advice is to get help and let them document what you teach them to create those SOPs.
Simplifying the Business to Grow Faster
Guest (Jen Hickle): At one point, I had 230 students including theater, but I realized I didn’t like the partnership or managing my parents. I gave my parents their own website and theater company, signed a lease for my own space, and went back down to 130 students. I knew if I uncomplicated it and just focused on lessons, I could grow faster.
Guest (Jen Hickle): In the new building, I grew to three front desk people. Once you have a team of three, you can delegate based on strengths—analytical people for numbers, creative people for flyers. Our school grew by 200% that first year. I learned SEO and digital ads, but we still used yard signs.
Navigating Volatile Teacher Relationships
Host (David Martin): Rapid growth means you had to hire a lot of teachers. What were some of those experiences?
Guest (Jen Hickle): I had one guy bragging to the front desk that he could take all his students home with him, so I had to let him go. Another teacher made my son cry. When I tried to talk to him as a parent, he accused me of sending my son in as a spy. My husband, Chris, drove up and told him, “You’re done. Get out”.
Guest (Jen Hickle): To get good teachers, I made Rogers School of Music a great environment. Rogers was an outermost suburb, and teachers had to drive 40 minutes from the city past other schools to work for us. I focused on clear communication, professionalism, and giving them cubbies for their things. Word of mouth spread, and I also built relationships with college professors to find standout students.
Testing Teachers and Easing into Trust
Host (David Martin): What was your onboarding system?
Guest (Jen Hickle): I had applicants give a mock lesson to my daughter while I listened to their interaction. I also learned not to give a new teacher a full three-day load immediately. I’d start them as a sub to see if students came out smiling and if the teacher was a good communicator. It’s like teaching kids to unload the dishwasher; you shadow them, let them do it, and then inspect it. Trusting teachers slowly was the best move.
Host (David Martin): Did you require a music degree?
Guest (Jen Hickle): At first, 100% yes. But I realized that students in college often make great teachers. Relatability to kids matters more than a degree. I needed teachers who could flex for a student with ADHD or autism and move with the times. My school became known for being child-centered rather than elite and classical. Everyone deserves a chance to try music lessons.
The Emotional Process of Selling the Business
Host (David Martin): You eventually decided to sell. What was that process like?
Guest (Jen Hickle): I was ready for a new mountain to climb, and we had systematized the business so it could run without me. It was enticing to buy because our SOPs were documented using the Entrepreneurial Operating System (EOS) and Traction. I actually “grilled” the potential buyer. I wanted to make sure they were worthy of my “baby”. It felt like letting a child fly, but it was the right choice.
Host (David Martin): Do you have any regrets about the sale?
Guest (Jen Hickle): I wish we’d asked for more money. But otherwise, the timing was right. Selling freed me up to expand my coaching business. Now I’m teaching business principles, which is my heart.
Understanding Strengths and Avoiding Business Shame
Host (David Martin): What do business owners need most?
Guest (Jen Hickle): They need to understand themselves. We all have shame around our weaknesses, but we should turn up the volume on our strengths and hire people to fill the gaps. I love the “Six Working Geniuses” and CliftonStrengths for this. Most business owners focus on what is broken, but they should emphasize what they are good at.
Guest (Jen Hickle): Entrepreneurs are often creative and easily distracted. The cure is a team. Get an admin to manage your email and hire finishers who have the “tenacity” genius to push projects across the line.
The Secret to Sanity: The “Butler” Email Strategy
Host (David Martin): What should business owners stop doing immediately?
Guest (Jen Hickle): Stop getting every single email. Start a new email address and tell no one. Let your VA sort your main inbox and forward only what you need to deal with. Put a “buffer” or a “butler” at the door. It saves your sanity so you can focus on big-picture dreaming and your family.
Advice to a Younger Self and the VA Academy
Host (David Martin): What would you tell your younger self?
Guest (Jen Hickle): Don’t give up, and don’t doubt yourself. You are more talented than you know. I lived with too much self-doubt for a long time.
Host (David Martin): Tell us about the VA Academy.
Guest (Jen Hickle): It’s a membership-based business modeled after Stu McLaren’s system. I focus on Christian homeschooling moms because we share values. I teach them the skills owners need—Slack, Google Docs, Canva, and marketing. I act as a matchmaker connecting business owners to these VAs.
Guest (Jen Hickle): You can start a VA for just five hours a week. Segment your business so no one has full access, and get VAs who are all-stars at specific tasks like bookkeeping or website updates. Don’t try to find a “purple unicorn” who can do everything; it’s not sustainable.
Looking Toward the Future
Host (David Martin): What’s next for you?
Guest (Jen Hickle): My mastermind is taking off, and I want to write more books. I’m also toying with the idea of a monthly in-person gathering for homeschool moms. I’m taking it one next step at a time.
Host (David Martin): Jen Hickle, thank you so much for being here and sharing your wisdom.
