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Michael Santoro: “It’s time to start working on a sale”

It’s time to execute your exit strategy. — In 22 years we have had two major peaks and two major valleys. It would have been nice if someone would have tapped me on the shoulder during one of the peaks and said, “It’s time to start working on a sale”. When you’re at a peak, you think […]

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It’s time to execute your exit strategy. — In 22 years we have had two major peaks and two major valleys. It would have been nice if someone would have tapped me on the shoulder during one of the peaks and said, “It’s time to start working on a sale”. When you’re at a peak, you think it’s going to go on forever and you’ll have plenty of time to act. If you’re reminded you have an exit strategy, you’ll know that the peaks are just another step along the way and not the final destination.


As part of my series about the leadership lessons of accomplished business leaders, I had the pleasure of interviewing Michael Santoro.

Michael Santoro is the founder of MacCase — the company credited with creating the Apple-specific case market in 1998. Before starting MacCase, he was a multi-award winning automotive and transportation designer penning the shapes for the original Chrysler Cirrus and Dodge Stratus sedans, the 1996–2006 Jeep Wrangler as well as the interior for the Gulfstream G5 aircraft.


Thank you so much for joining us! Can you tell us a story about what brought you to this specific career path?

You’re very welcome. It’s great to be here.

My career path was laid through using philosophy in the pursuit of happiness. If I believe the purpose of my life is to be happy, then I need to know how to structure a life that will create it.

To me, that structure is very simple. We live in two worlds. One is the ethereal world inside our heads. There, in our mind’s eye, we have a vision of how we want the world to be and how we see ourselves in it. The other world is the concrete world outside. It’s the world of physical things and other people.

Happiness occurs when the ethereal world in your head matches the concrete world outside. The challenge is in making that happen. The way you get the world around you to match the world in your head is to honor your values.

My highest values are freedom and creativity. All you have is time. And then you don’t. If you are not in control of your time, you’re not free. It has been my experience that entrepreneurs know this instinctively.

I was a very successful automotive designer at Chrysler, doing 3 exterior production car designs in the 5 years I was there. But I still had to be at my desk at 7:30 every morning. So my value of freedom was not being honored despite that being a highly creative and supportive environment.

If I was going to be happy, I needed a career where I could honor both values, one where I could “make my own hours” and maximize my creativity. I started as a painter, was trained as a designer, and then an entrepreneurial life offered me a chance to be in control of my time and therefore my freedom. At the same time, it’s allowed me to honor my creativity at the highest levels. I’ve been very happy for the last 22 years.

Can you tell us a story about the hard times that you faced when you first started your journey?

I was out surfing on a pretty big, overhead November day when my leash broke and I had to swim in. When I went to swim, I could not breathe. It felt as though I was being choked. I dove under the water, pushed off the bottom towards the beach, came up, and took another breath, basically creating a “W” pattern under the water as I moved closer towards the shore. When I finally got back to the beach a friend asked if I was OK. He told me I looked terrible. Soon after I went in for a checkup where I was diagnosed with Hodgkin’s Lymphoma.

There is nothing quite like a cancer diagnosis to derail not only your entrepreneurial dream but also your entire life. Chemotherapy is a controlled death experience. Spiritually, you know this. The very life force that gets you out of bed every day is in a fight for its life and you cannot escape it. There is nowhere to run.

The best way I can explain the experience is to imagine yourself hanging from a muddy cliff edge at night in the pouring rain. It’s cold, you’re alone and you cannot see the bottom. It is literally, the abyss. Every few moments one hand slips off the edge as the mud gives way and in a panic, you reach back to grab hold just the other hand slips off. You do this minute after minute, hour after hour, for months. Hanging from that cliff edge and not falling becomes your life. That was a pretty hard time.

Where did you get the drive to continue even though things were so hard?

Picture an ellipse. You have the two endpoints at the far ends and the widest part in the middle. All of life happens between those two endpoints of the long axis. Most of life happens where the ellipse is at it’s widest. These are the activities that fill our days.

In the middle, there is a centerline. On one side are the joyous events of our lives. The holidays, a promotion, vacations or the birth of a child all happen here. At the far end of the joyous side is the experience of being in love.

There are times where you cross from the side of joy to the side of hardship, pain, and suffering. The loss of a job, a loved one, financial instability, and uncertainty reside here. On the far end of this side of the ellipse is where your mortality is at stake. This can take the form of an external hostile survival situation or as in my case, an internal one. When a doctor tells you the third worst thing a person can hear, “If you do not do something, you will die”, that wall your leaning on is the far edge of the ellipse.

It’s interesting though, how similar the experiences are at the extreme ends of the ellipse. When you are in love, you don’t care about eating, sleeping, your job, or much of what else normally constitutes your days. You just want to be with that other person. It’s wonderful to be lost in that single-minded joy.

When your mortality is at stake you don’t care about eating, sleeping, your job, or much of what else normally constitutes your days either. You’re either going to survive or you’re not. It’s the same single-minded experience, minus the joy and wonder. I got the drive to continue because I did not want to die. It’s that simple. I was motivated by my love of life itself. I don’t hate a lot of things but I hated being a “professional patient”. I just wanted to get back to the other side of the ellipse.

After an experience like this, you realize what a bad day is. In the future, my company would lose its biggest customer and 50% of our revenue overnight. Years later, after building it back up and exceeding it, we’d lose 90% of the traffic to our website and another huge portion of our revenue. Yet neither one of those terrible business setbacks was to me, a bad day. Being at that far end of the ellipse gives you perspective and resiliency beyond what you thought was possible.

So, how are things going today?

Things are good. I’m healthy and we are holding our own with all that is going on here in 2020. We have over 2 decades of loyal customers who love what we do and that is a special feeling. Combine that with all our new customers who are discovering the brand for the first time and you have a recipe for continued success.

How did grit and resilience lead to your eventual success?

I’m not someone who gives up. I never was. I don’t know if that is something you can teach or you’re born with. Grit and resilience are like old friends to me. I got to know them very early in my design career. Statically, you have a better chance of playing professional football in the United States than becoming a professional car designer.

How many professional football players do you know?

Yet against these incredible odds, with a bit of talent, a boatload of ambition, and unrelenting grit, I was able to achieve that childhood goal. I could have given up a hundred times along the way.

While grit and resilience are important, I think there is an element to success that is equally as important: Humility and the ability to learn. What good is grit and being resilient if you never improve the skills, knowledge, or awareness you need to succeed because of your hubris or your inability to absorb new information?

Confidence, belief in yourself and your ideas has their place and are important. Knowing when to be humble and when to realize that you need to learn something new to get to the next level and be open and honest with yourself about it, can make all the difference.

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?

Early on, a gentleman called and asked if I was interested in taking a look at his invention for a protective laptop cover. I would get calls like this all the time. We set up a meeting and he told me about the idea. It was a polycarbonate, molded shell that clipped onto the exterior surface of a laptop.

One good thing about being your own customer is you can apply your values to an idea and believe that the majority of your customers will feel the same. Apple was spending a lot of money on research and development to make its laptops thinner and lighter.

The idea that you would clip two pieces of relatively thick plastic to each side of an Apple laptop (that you paid a premium for because it was so thin and light), was an anathema to me. Moreover, this plastic cover would over time, abrade the very surface it was charged to protect. Apple customers are too smart for this. I passed.

He took the idea to a competitor and they sold tens, if not hundreds of thousands of these things. We get emails from Chinese companies selling knock-offs every week. Despite their success, I still feel the design is fundamentally flawed vs. a good quality, well-designed laptop sleeve. There were several generations of Apple laptops whose screen hinges were ruined by the extra weight of these clip-on covers.

So was it a mistake to pass on this? I stuck by my principals and passed on what I still think to this day, is a bad idea. In that sense, I can feel good about it now. From a business perspective, I passed on an idea that was worth an incredible amount of money.

The lesson I learned was that I didn’t know the market as well I as thought. I knew myself pretty well though and I can live with that.

What do you think makes your company stand out? Can you share a story?

There are several things.

One is that the idea of an Apple-specific case was an original one. Before I drew the first MacCase, (a colorful briefcase matched to the original iBook), the only option for protecting and transporting your Apple laptop was to purchase a general use case designed for a similar-sized portable PC. Typically these were pretty dull and boring. As with many products, they’re created not to delight, enchant, or inspire but not to offend. This is a very important design principle to understand.

Apple users tend to have high aesthetic sensibilities. They will pay for good design. MacCase was the right idea at the right time, a real Blue Ocean Strategies moment. So like Levis and Mercedes Benz, we get to be the original, authentic brand in our space.

More importantly, we are a design-driven company. The company was a few months old when we went to the MacWorld trade and consumer show in San Francisco for the first time. Our entire line was just the iBook case in all the colors. The party piece of the design was the window on the front panel of the case that allowed the Apple logo to become part of the case design.

So if you had the Tangerine iBook, you bought our matching Tangerine case and the Tangerine Apple logo on the front of the computer showed through the window integrating it into the exterior design of the case. We had no idea how the Apple community was going to react to this unorthodox design. Luckily, the response was overwhelmingly positive. The people that liked it loved it.

The design was simple but it made everybody that saw it smile. The principal, to have a computer case that had a presence and was charming, was the opposite of everything that had come before it. It may not have been for you but it was interesting, cheerful, and acknowledged the individuality of Apple users.

When we got back from the show on Monday morning the phone rang. It was Apple’s legal department. “We saw your products at the MacWorld show”, the voice said flatly. “I just wanted to congratulate you. You’re the first person to figure out how to use the Apple logo without getting sued. Best of luck to you.”

Fast forward 22 years and we’ve just launched a professional level, leather Folio for the iPad Pro that allows the customer to customize the design to meet their needs on any given day. People have been making iPad cases for 10 years now and there’s never been anything like this. It’s a simple, original, elegant design that provides a solution that a large number of users have been looking for.

This is the kind of continuous design innovation we have been producing since that first iBook case. The timelessness of our aesthetic, our attention to detail, superior protection, and world-class quality has helped us stay one step ahead for over 20 years.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

There have been so many companies that have come and gone since we started. I was told that you can make lots of little mistakes but you’re only allowed one fatal one. So my first tip would be don’t make a fatal mistake.

Regarding not burning out, you have to have a separation, downtime, call it whatever you want, away from the work. I have a friend who has a start-up and she’s constantly complaining about how stressed out she is while she answers work-related calls and texts at 11 p.m.

I raced road bikes for 14 years. When you are training you have hard days and easy days. But your fitness is only as good as your easy days are easy. In cycling, if you over-train, it’s called “falling off the razor”. If you “overtrain” in your entrepreneurial life, you can set yourself up to make that one fatal mistake. Work smart when you’re working, and relax and recharge when you’re not.

None of us can achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

Going to a specialized art high school, I had seen the results of unsupportive parents. Many of my friends who had much more natural talent than I did found it impossible to continue on a creative life path due to the lack of support. Even worse, some classmates had parents who were openly hostile to their pursuit of a creative life.

While I knew that my mother got it, I never felt my father understood what I was trying to do. He didn’t come from a world where people did creative work for a living. He got up every day, went to work, and never complained. His stoicism for what I was trying to achieve was the foundation on which I was able to dream big.

His work ethic and the stability he provided gave me space and time to develop my talent. He made sure I had the money I needed for art supplies even though he might not have been able to see how someone was going to make a living using them.

During my junior year at Pratt, I got to take my first real transportation design course where I had to build three-dimensional scale models of my designs. Most models of this kind are done in clay or foam but I also did wireframe sculptures. These were the largest and most complex models I had ever created.

When the first model was finished, I called my father down to show him. Like with any creative work, there was were piles of clay, foam, wire, paper, and tools scattered around the basement floor. Sitting in the middle of all of that was my finished design. He looked at the sketches on the wall, the model, and then looked around the room and said only, “When are you going to clean this place up?”

Fast-forward 4 years and I am working at Chrysler. My dream to become a professional car designer had come true. My parents were visiting from New York and I wanted to get them into the studio to see what they were part of helping me achieve. The problem was automotive design studios are highly secured areas.

I asked my manager if I could bring my parents in on the weekend for a tour and was flatly denied. Many people who are from the Detroit area that works for one of the Big 3 manufacturers may have family members who work for the other two. As a policy, I understand the ban. But my parents didn’t work at GM or Ford and if Chrysler was going to fire me for wanting to share this success with my parents they would have had a public relations nightmare on their hands. Or, at least that’s how I justified smuggling my parents in.

On the drive down to Chrysler’s Highland Park world headquarters, my father seemed very excited. He was asking a lot of questions. One key thing to understand is the sense of theater that exists in design studios like this. When you enter the building, the halls are very dark with dark colored floors and walls of grays or creams. It feels as if the color has been drained out of the world and you’re now walking through an old black and white movie.

When you slide the security card through the reader and open the door of an automotive design studio, it’s just like Dorothy opening the door to Oz. It’s otherworldly. You’re immediately hit by the brightness of the lighting and the expansiveness of the space. Full-size clay models of cars literally from the future are aligned in rows on special steel plates and the walls are covered in color.

The color is the result of dozens of renderings of cars that do not exist yet that are neatly organized by the designer. And there, in the middle of them, all were mine. My father walked up to the wall and saw our name on the drawings. He turned around and saw a full-size clay model of my design that the drawings represented.

“It’s just like what I was doing in the basement, except now it’s for real”, I said happily, connecting the past, present, and future. He smiled but didn’t say a word. My mother would later say that she had never seen him react to anything in the way he reacted to that tour. He got it. He finally understood what I was trying to do and it was because of him that I was able to do it.

I’d also like to mention Mr. John Herlitz. John was the Director of Exterior Design for Chrysler and the man who hired me. Upon graduating from college, I interviewed at Chrysler, GM, Mazda, and a few other companies. All passed. 7 months after my interview at Chrysler, John called me out of the blue and asked if I was “still doing cars”. I was, alone in my parent’s basement. He asked me to keep him posted on my progress, which I did.

Several months later I interviewed again at Chrysler (giving up a full scholarship to Art Center to do so). John rearranged his office so I could set up my presentation. He brought in various levels of Chrysler’s design management to hear my pitch. About a week later he called again to tell me Chrysler was interested in offering me a post-graduate internship which they had never done before. I accepted. The work I produced during the internship lead to a full-time position. When asked why he hired me John replied, “He was the most passionate young designer I had ever met”. I’d like to thank John for taking that chance.

How have you used your success to bring goodness to the world?

I have tried to make everything that I have created and put into the world as inspiring, beautiful and of the highest quality as possible. Human beings have a need to see the beauty in the world, not only in nature but beauty in the work produced by other humans. This is why people are still lining up around the block to look at 400-year-old paintings, drawings, and sculptures and paying $50 million for one 50-year-old car.

More pragmatically, I have one of the top channels on YouTube for car design where I am sharing the knowledge with the next generation about what it takes to achieve success in this highly competitive field.

What are your “5 things I wish someone told me before I started leading my company” and why. Please share a story or example for each.

1. Remember to work on your business long after you begin working in your business.

When you first start, you spend so much time working on your business. Things like the overall plan, the marketing, getting funding if you need it, are all part of working on your business. At some point, you cross over to working in your business to implement all of your ideas. While this can be great fun and lead to a lot of happiness, like a train pulling out of a station, once it gets rolling you can get caught up in the momentum. It would have been nice to be reminded every once in a while to go back and continue to work on my business.

2. You need to think about how big you want to be.

I was so happy to have transitioned to an entrepreneurial life that I never thought about what I ultimately wanted to manage. There is so much emphasis on surviving the early years. No one ever suggests you think about what you might want to be managing after year 5. Managing a $1 million company is a much different experience for a founder than a $10 million one. You gain things and loose things. Be sure you’re gaining the things you want and don’t mind losing the things you will.

3. Hire a good PR firm and here’s why.

Before I was a car designer, I was a successful painter in New York City. The gallery took care of all the media relations. At Chrysler, they had a whole PR department with an unbelievable media reach. Even when things were booming at MacCase, I never thought to do it on a large scale. We did work with someone locally but never at the national level. I think things would be easier now if we had.

4. Make sure you enjoy the successes.

Entrepreneurs tend to view their enterprises from a “half full” worldview. They often feel whatever they’re doing is not good enough. We are always chasing the next thing. Celebrate and appreciate when times are good. The next challenge will be coming at you before you know it.

5. It’s time to execute your exit strategy.

In 22 years we have had two major peaks and two major valleys. It would have been nice if someone would have tapped me on the shoulder during one of the peaks and said, “It’s time to start working on a sale”. When you’re at a peak, you think it’s going to go on forever and you’ll have plenty of time to act. If you’re reminded you have an exit strategy, you’ll know that the peaks are just another step along the way and not the final destination.

You are a person of great influence. If you could start 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. 🙂

Beauty Saves the World.

Meditate on that everybody.

How can our readers follow you on social media?

MacCase has the following accounts:

https://www.instagram.com/original_maccase/
https://www.youtube.com/c/MacCase/videos
https://www.facebook.com/FanMacCase

My work can be seen here-

This was very inspiring. Thank you so much for joining us!

Thank you for the opportunity.

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