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Matt Ross: “Everything takes longer than you think it’s going to take”

When I decided to do this at 50, I was the CEO of a visible brand for five years, and that was a startup. I wasn’t the founder, but I was deeply responsible for building it and innovating and doing things. I had to make a very big decision to do this because to be […]


When I decided to do this at 50, I was the CEO of a visible brand for five years, and that was a startup. I wasn’t the founder, but I was deeply responsible for building it and innovating and doing things. I had to make a very big decision to do this because to be honest I left a lot of opportunity on the table, and I didn’t know if anyone would come. What I’ve found is that there’s tremendous demand for what we do and we’re doing it well so in a very strange way my job is more enjoyable and I have greater appreciation for what I do for the work we’re doing than I even thought I would. It’s important, we’re making a tremendous difference in people’s lives, we’ve taught thousands of people and we’re just getting started still.


As a part of our series about entrepreneurs who transformed something they did for fun into a full-time career, I had the pleasure of interviewing Matt Ross. Matt is the Founder & CEO of One River School, a fast growing franchise that is transforming art education US with focus on to introducing more cultural opportunities outside of core urban areas, and make the creation of art fun and interactive for all ages. Since the opening of its first location in 2012, One River’s innovative program has taught thousands of students across Illinois, New Jersey, New York, Oregon, Texas and Connecticut. Prior to creating One River School, Ross was the Founding CEO of School of Rock overseeing its expansion from five locations to 50 with another 30 in contract during his five-year run, making it the largest network of music schools in the world. Before that spent 20 years as an executive in the radio industry.


Thank you so much for doing this with us! Can you tell us a bit about your “childhood backstory”?

I grew up as a kid who was super creative, but also played sports. I would star in my school plays, but my parents wouldn’t come. I never got upset about it since I just figured, they’re coming to my games, so I deferred to sports. Later I realized I had creative skills and that was evidenced through music and advertising, and things I’ve done professionally. It’s kind of interesting that I saw later in life what would’ve happened had the creative side had been cultivated in me. I might’ve been an artist.

What was the catalyst from transforming your hobby or something you love into a business? Can you share the story of your “ah ha” moment with us?

Before I started One River School, I was the CEO of School of Rock, which is now a chain of almost 250 locations, but we were pretty much in the startup phase with five locations when I started. I ran this chain of music schools and built them into the largest network of music schools in the country. When I left there, I was reflecting on what I should do next, and I simply asked myself “Why are there no cool art schools in my neighborhood?” And that was an a-ha moment, and I started to investigate and dig into a little bit more into the research on what it took to be a for-profit art school, and decided I would take a swing at building a prototype school in Englewood, New Jersey.

There are no shortage of good ideas out there, but people seem to struggle in taking a good idea and translating it into an actual business. How did you overcome this challenge?

When I decided to do this I wasn’t the 23-year-old entrepreneur. I was a 50-year-old accomplished executive, MBA in finance and spent the bulk of my career in General Management and Leadership and sales and marketing so I was cut out in many ways to start a business. So, the notion in me having this idea and translating it into an actual business, really, there were no personal challenges involved other than the time and effort it was going to take and the capital.

I think the main struggle was pulling the ripcord and committing to it because I had a lot of other options. So I had this feeling that wow, I just spent five years building the School of Rock and I built that from 5 schools to 55 in four years and we had another 30 under contract. I really accelerated that business, and I liked what I got from it. I liked what I felt when I was helping people learn music and giving musicians career opportunities and I was thinking can I translate some of that into the art space.

What advice would you give someone who has a hobby or pastime that they absolutely love but is reluctant to do it for a living?

Figure out what you do well and find people who can help you do the stuff you don’t do well. So in the case of a lot of artists or people who are hobbyists, they may have the product idea or they might really be an expert on exercise or cooking, but can they manage the business, can they manage the financials, can they evolve the strategy? So, I tell people find a good partner. I think it’s one of the best things that you can do if you don’t have that full tool kit. So find a great partner, and if you don’t want to find a partner, find a right hand who can do everything you don’t do well.

It’s said that the quickest way to take the fun out of doing something is to do it for a living. How do you keep from changing something you love into something you dread? How do you keep it fresh and enjoyable?

For me it’s really easy because the culture of our company is built on this. One of the earliest things we teach people about during training is this is about fun and doing good and doing well, and doing well by doing good. So we find mission oriented people who really enjoy this. For me, I do the things I do well, and I find out what other people love to do and do best. The way to do this, for me as an entrepreneur is to delegate the stuff that I’m not good at and don’t love to do and to teach my people to do the same. It allows me to do stay in the lane in what I do really well with people, culture, strategy, vision and marketing so I’ve got people to do operations, training and technology among other things.

What is it that you enjoy most about running your own business? What are the downsides of running your own business? Can you share what you did to overcome these drawbacks?

What I love most is the people side of the business. I love mentoring and growing talent. I love finding talent and giving them a place to work that feels different. The fact that I can create the culture of not only how do we create the products, but how do we train our peers and employees so that’s as important as how you treat your customers. It’s all about the internals. If the internals feel great, they will take that out to the customers.

I also love the strategy side. What do we build, why do we build it, what are the obstacles and what are the plans to fix it.

The downsides are that it’s really hard to shut it off at night and until you have really accomplished, well-trained people working with you, you really can’t take a break. I’ve been at this for seven years and I’m starting to now really benefit from the fact that I’ve got a team.

Can you share what was the most striking difference between your actual job and how you thought the job would be?

I think the striking difference is positive. When I decided to do this at 50, I was the CEO of a visible brand for five years, and that was a startup. I wasn’t the founder, but I was deeply responsible for building it and innovating and doing things. I had to make a very big decision to do this because to be honest I left a lot of opportunity on the table, and I didn’t know if anyone would come. What I’ve found is that there’s tremendous demand for what we do and we’re doing it well so in a very strange way my job is more enjoyable and I have greater appreciation for what I do for the work we’re doing than I even thought I would. It’s important, we’re making a tremendous difference in peoples lives, we’ve taught thousands of people and we’re just getting started still.

Has there ever been a moment when you thought to yourself “I can’t take it anymore, I’m going to get a “real” job? If so how did you overcome it?

No I don’t think it was a moment where I said we can’t take it anymore. I would say in the first two years to three years it was super hard and it did challenge my stamina and it challenged my emotional commitment. I didn’t know if we were going to open a lot of these, but I always knew we would get one or a few to be successful. I think how I overcame that was making sure I was focused on the experience that our customers had, building the team, but also staying focused on the numbers. A lot of entrepreneurs whether they’re young or old or are CEOs believe what they’re saying at such a high level that they cannot objectively look at whether what they’re doing is working or not. I think what people need to do is step back do that gut check and surround themselves with people who are willing to do that gut check because it’s not for everyone. If you hit that wall because you’re not successful and not going to be successful you’re actually doing yourself a service by closing your business, selling your business whatever it is. If they do, take what they learned and do something else.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

When we first opened our first school in Englewood, New Jersey we had a big space, we had a lot of excess space so we were programming not only the school, but also this large art gallery. We started to create events in this gallery. For some reason we thought it would be cool to have an open mic night and I sing. When I got up, I was terrible that night, and I thought I lost the room! And I’m like oh my god, I have to start practicing my musical side because it’s rusty, but then I was like what the hell am I doing music events at One River School. This is a visual arts and design program with art gallery space I don’t need to be a multi-purpose venue and I certainly don’t need to be performing here!

Who has inspired or continues to inspire you to be a great leader? Why?

When I think about that no one person comes to mind, but I’m a voracious learner so I could tell you that I continue to read numerous books on leadership and culture every year. There’s people in the hospitality space, there’s great companies around us that inspire me. When I look at what Soulcycle has done as a brand and Warby Parker, they are really good at what they do. They build great brands, great retail experiences they built a great story with investors and a culture that really works. It’s companies that really inspire me.

How have you used your success to make the world a better place?

Twice a year we have art projects that are deeply tied to sort of an important thing that happens in our world or things that people are dealing with. In the month of October, our teen students do something called the Pink Project that make an artwork that honors women with breast cancer. They all have to create an original artwork that uses the color of pink and they have to demonstrate the courage that people have to have to overcome cancer then we exhibit that artwork. We’re teaching kids and teens to think about people who are dealing with challenges and make an original artwork that honors them, but along the way its forcing them to think more about how fortunate they are and how less fortunate others may be.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

  1. Really how hard it is to find great talent, which I knew, but continues to be reinforced every day.
  2. Everything takes longer than you think it’s going to take.
  3. Everything takes more money than you think it’s going to take
  4. Finding great real estate is really hard and takes a lot of time. We are dependent on that.
  5. How quickly the world was going to shift from desktop to mobile as it relates to computing and the effect that this would have on your technology and your marketing platforms.

What person wouldn’t want to work doing something they absolutely love. You are an incredible inspiration to a great many people. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

People need to ask more questions and listen more. What do I mean by that? We’re in such a noisy world right now, everyone is so stressed and the geopolitical environment difficult. We know what’s happening in the US right now and there’s so much arguing going on and cable news and social media. I would love if people said tell me more, I would love if people would try harder. Stephen Cauley used the term, “The best way to be understood is by understanding.” If people worked harder to understand others point of view to understand other perspectives and points of view they would be more understanding and less reactionary. I think people would treat others better, we’d have more discussion and we’d get more solutions done in the greater world.

Can you please give us your favorite ”Life Lesson Quote”? Can you share how that was relevant to you in your life?

It’s a Latin term: “Finis Origine Pendet”, which translates to the end depends upon the beginning. The end depends upon the beginning is really important with every encounter you have with someone new, or something new. We form our opinions instantaneously and that’s why I think it’s hard to provide hospitality level service business and in life. You have to get the first 3,5,10 seconds of the exchange right and the brain processes really fast. Smiling, asking simple questions like how I can help someone, making it about others. I did this intuitively, but when I heard this quote, it really had a dramatic impact on my life and I sort of make sure that when I have short, quick connections with people I try to really make it about them not about me. Be likable, be kind and inevitably people will hopefully walk away from a quick encounter wanting to spend more time with me and learn more about what I do because I didn’t suck all the energy out of the room with my stuff.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

Mick Jagger, the reason is as a guy who was young a young child in the 60s and grew up in the 70s I saw what rock ’n’ roll did to change the culture and the role it played in my life and helped me to appreciate and learn. The Rolling Stones to me are the most iconic rock band ever, and Mick Jagger is the most iconic rock star ever and given the fact that he created that magic, I’d like to hang with him a little bit.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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