Dimitra: I think having excellent clear communication is key and letting your team know your expectations. Also, from my experience it’s best to work with like-hearted people.
As a part of our series about lessons from Thriving Power Couples, I had the pleasure of interviewing Dimitra Milan and Jake Dunn.
Dimitra Milan is a co-owner and mentor at Milan Art Institute where she is pioneering a new age of artist influencers on social media and empowering them to change the world with their art. Prior to joining Milan Art Institute, Dimitra generated over a million dollars of artwork sales by the age of 15. Through her artwork and mentorship, she is spreading beauty across the entire planet and helping other artists find their true passions. Her husband, Jake Dunn, is a painter, writer, music producer, videographer and business leader. He is a curious soul, constantly adventuring into new arenas of creativity and finding ways to unite the different forms of art. Still in his early 20’s, Jake has become a business leader at Milan Art Institute alongside Dimitra by taking bold moves, working incredibly long hours and dedicating himself wholeheartedly to his endeavors.
Thank you so much for doing this with us! Can you tell us a story about what brought you two to your respective career paths?
Jake: My story isn’t quite as straightforward as Dimitra’s. After aimlessly frolocking in college for 3 years, I decided that I needed a major shift.
I studied creative writing at the University of Southern California and I loved writing — still do — but I found myself helplessly obsessed with music production after a friend (and Youtube) demystified it for me. To me, it seemed just like writing: simple, yet beautifully complex at the same time. All you had to do was have the patience to build in layers. This obsession, paired with unhealthy drug habits drove me to skip classes in the pursuit of music. 3 years into college, after being a straight-A student all throughout high school, I was failing my classes. College wasn’t supposed to be a playground for me, but I was treating it like one. Around this time, I visited home (Arizona) and reconnected with a prior friend/short-lived romance, Dimitra. After explaining my situation, she could see that I needed help and talked with her mom about offering me an opportunity to work/live at their “Artist Commune,” creating music for videos that they were producing. I hesitated, agreed, then flaked out. But Dimitra was persistent. She saw destiny. She drove 4 hours to my home on the opposite end of Arizona to convince me; her passion and dedication really took me off guard. I wasn’t used to that. So I decided to move into the artist commune.
I immediately felt at home. I connected deeply with the Milan family and poured myself into all of the work that I did for them, making little to no money at the time — food and rent was covered — but beyond satisfied with the opportunity to be a part of something so special. My transformation was swift, stepping into my true self surrounded by people that elevated me. I quit drugs the day I moved in. I started out holding a camera and was enthralled by the whole filming process. I then moved into video editing. Given my experience with creative writing, I became the copywriter as we neared the launch of the Online Mastery Program, Milan Art Institute’s flagship art program. Following the launch, I decided to actually take the program myself. I fell deeply in love with painting. It felt like an extension of writing and music. I started to see a grand vision for my life falling into place, all of the skills I was learning lending themselves to one another. I was becoming the polymath that I had envisioned myself to be since I read The 4-Hour Chef by Tim Ferriss in high school.
After I graduated from the Mastery Program, Elli Milan, Dimitra Milan and Elijah Gedz (the co-owners of Milan Art Institute) offered me a chance at partnership in the business. They were looking for someone to champion a new project, later titled Milan Art Club. I leaped at the opportunity.
In summary, there isn’t an isolated story that has led to my career path, but rather the culmination of the last 6 to 7 years of my life has led to it. If I did have to isolate the turning point, though, it was taking the Mastery Program. It completely changed my life.
Dimitra: When I was 13, I absolutely fell in love with painting. I was consistently attending classes at Milan Art Institute, my parent’s art school. At first, painting was only a hobby. But then I started to sell a few paintings, and I witnessed how other people were affected emotionally by my work. This was an empowering feeling and it motivated me to paint as much as I could. I remember the first painting I sold, a little acrylic toucan for $50 and I thought “Wow, people actually like and want to buy my artwork!” When I was 14, I started taking art more seriously and with everything in me, I wanted to find my unique style and voice as an artist. I wanted my style to stand out. I took several portfolio classes taught by my mom in order to find my style. They were kinda like artist boot camps and we had to create 4 paintings per week. Through that immersive and intense experience, I finally found my voice. I remember the painting that started it all, a portrait of a girl with a crow on her shoulder painted in a mixed media style combined with realism. I fell in love with the process and subject matter, combining women with animals and telling a story. Since that day, I’ve dedicated my life to my art career, and worked very hard to be where I am. With hard work and passion, I believe you can achieve anything your heart desires.
Can you share the most interesting story that happened to you since getting married?
Dimitra: Well, I feel like our life together is always an adventure! Jake and I are both adventurous souls. I feel so blessed to share everyday with Jake and work together towards the same goals and passions. It’s truly a gift to work beside the one you love. It’s hard to choose one story to share… something recent is that we just finished building our first house together! We basically live inside our art studio, so I feel very blessed to be right next to my studio space and be able to paint anytime I want. It’s just perfect!
Jake: I would have to say filming a reality show has been the most interesting project so far. Everything turned out much better than we could’ve hoped for when we set out. Everyone involved did such an amazing job and the story is very inspiring probably because we didn’t try to force it. Meaning, we didn’t force a narrative at all, it just naturally evolved over time.
Dimitra is one of the hosts, alongside her mom, Elli. I directed and produced the show. We created it exclusively for Milan Art Club, so the members could watch professional artists work on the same challenges (paintings) as the members every month. We’ve learned a lot about how to work together to create something over an extended period of time and it’s been such a rewarding experience. And it’s super entertaining watching all of the Milan family members interact.
Can you share a story about a mistake you made when first starting out, and a lesson you learned from it?
Dimitra: I’m not sure if I call this a mistake, because I feel like everything happens for a reason. And if I didn’t go through this experience I’m not sure where I’d be today. When I was 15, I signed a contract with a publishing company in Hawaii. They wanted to put my artwork in galleries all over the US, starting in Hawaii, and create limited edition print programs. They would handle all the business aspects including building a website, branding me as an artist, selling artwork, gallery relationships and pretty much everything else. It was an exclusive contract so I wouldn’t be able to work with anyone else. They had the first rights to all my originals, which they wanted 8 complete oil paintings per month.
So, at that time, it was the opportunity of a lifetime! I was basically handed a career at the age of 15. It was a lot of hard work and it was extremely successful. To the point where I was feeling burned out and couldn’t keep up with the demands, and had to say no to expanding to more galleries. I felt at times I was a machine, painting for the masses, rather than taking the time to paint the visions in my heart. To make a very long story short, I learned so much in this partnership and most importantly I realized how much I cared about the business side to art. I learned I’m the type who wants to be my own boss, and not abdicate control to the publishers who were branding me as someone I wasn’t. They branded me as a Hawaiian artist, even though I lived my whole life in Arizona! It wasn’t the true me. But I fully recognize I wouldn’t be where I am today without the experience. I wouldn’t have gained the knowledge I have, living through all of that. I’m grateful for the decision I made to work with them, and I’m so grateful I was strong enough to leave when the time came.
Jake: Growing up, my mom used to time me with everything I did. Whether it was taking out the trash, cleaning my room, building a fort, or riding my bike to the end of the street and back, everything was a race. This mentality permeated into how I did everything. If I couldn’t do it quickly, it was a failure. What I’ve realized in the last couple years of my life, often working 12–14-hour days for an extended period of time and not being anywhere close to where I see myself and this incredible business, is that life is a marathon. Those who can keep the consistent pace win. Sometimes, you have to sprint in the beginning in order to catch up or get ahead, but then, it’s just you. You are your competition. You are trying to beat your best time, it’s just a longer race. So, I guess I’m grateful to my mom for teaching me that it’s important to always be trying to achieve your best, but I’m glad that I’ve become part of a longer race.
What do you think makes Milan Art Institute stand out? Can you share a story?
Dimitra: There are many things that make Milan Art Institute stand out. The fact that we as professional artists share all our “secrets” with our students and don’t hold anything back. We are vulnerable and share all the experience and knowledge we have to give. By sharing these things, we attract more! We don’t have a “lack” mindset or mentality, and I think that’s key to living a successful career as an artist. The more artists we can make successful and live out their dreams, the more beautiful and amazing this world will be.
Jake: About a year ago the team was gathered for our Monday morning meeting, brainstorming what we could do to connect with a larger audience. Dimitra had the idea to create an abstract painting course. Most people are terrified at the idea of painting an abstract because there’s no associated imagery to ground the painting. We wanted to make abstracts accessible to everyone. Elli says she thinks it’s a great idea, and that, “If we film it all today, someone can edit it tomorrow, Jake can write the copy while he’s there for the filming, and Elijah can have it uploaded and on the website by Friday.” To top it all off, we were making it free for the first month or so. Most of the time, it took around a month of turnaround for our online courses and Elli wanted to do it in just 3–4 days. Everyone jumped on board and made it happen. That’s the beauty of our school. We all care so much about what we’re doing and all wholeheartedly believe that we are changing the world with what we’re teaching. And the fact that we’re a family business that’s grown beyond the family is further evidence that there’s something special going on here.
Are you working on any exciting new projects now? How do you think that will help people?
Dimitra: Yes! We are in the process of writing a book together. Love stories have always inspired me, and I’ve always dared to believe that I would live out a great love story too. How Jake and I came together is a long story with lots of spirals and turns. We came from very different backgrounds and for a long time I tried to forget I ever met him. We wanted to share our story with others to help them believe anything is possible, as long as you have the faith to believe it. We hope to inspire people and let them feel God’s amazing power and love. Most of all, we want to help people realize they were born with a unique destiny and deserve to have the greatest love.
Jake: Yes, everything Dimitra said! In addition, we are working on a few exciting new collaborations with our art. One of the pieces will be filmed and turned into a music video for one of my original songs. I’m really trying to let all of the different art forms flow into each other, even going so far to record different folly sounds from painting and incorporating those into the music. And it just so happens that my wife is my favorite artist of all time so it really is an honor every time I get to collaborate with her. I hope that Dimitra and I collaborating with everything that we do inspires others to involve their partners in their creative pursuits. We both believe that’s how God designed relationships and marriages to be: a collaboration of life.
What advice would you give to other industry leaders and business owners to help their teams thrive?
Dimitra: I think having excellent clear communication is key and letting your team know your expectations. Also, from my experience it’s best to work with like-hearted people. People who care about your vision and feel connected to it just as much as you do. These people can become lifelong partners, and they are priceless. I think sharing your vision on a consistent basis is also KEY. Your team needs to be on the same page with the flow of the business. Weekly brainstorming sessions have become very fruitful and keep our team meetings very interesting and fun to be a part of.
Jake: Passion is contagious. When you exude passion, your team members will pick up on that and it will drive them to achieve greater results than they ever would when being driven by fear. Like Dimitra said, your whole team should be like-hearted, striving to achieve the same vision. That vision should be incredibly transparent and it should be at the center of every decision. If something you’re about to do will help you short term, but work against your long-term vision, don’t do it.
How do you define “Leadership”?
Jake: Jocko Willink is definitely one of my heroes when it comes to leadership. A leader is someone who takes extreme ownership over every aspect of their domain. That means you take full responsibility and never abdicate blame. You bring out the best in your team, exalting their achievements and forgiving their shortcomings, so long as they gave it their all. You are the CHAMPION of your cause. You steer the conversation towards the objective, while simultaneously making sure that your team members feel heard. You give your team the space it needs to make important decisions and you empower them, even if you sometimes feel like your idea might be better because someday, you want your team to expand, and guess what? You’ll need more leaders to work with you. Great leaders breed excellent followers. Excellent followers become great leaders.
Dimitra: I totally agree with Jake! I love Jocko Willink too, a very motivational guy.
None of us are able to 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 about that?
Dimitra: I wouldn’t be where I am today without my parent’s support and encouragement. I feel so lucky to have them in my life and to this day we still live on the same property! They are both amazing friends and mentors. We share a lot of the same visions and dreams, and I think that’s very special. My mom has helped me so much along the way in my career, in more ways that I can count. In the beginning, she constantly pushed me outside my comfort zones, which helped me really grow as an artist and a person. She believed in me when I didn’t. She reminds me of what I’m capable of when I set my mind to it. And I am so grateful for that.
Jake: It’s towards the end of the Mastery Program and we’re sitting in a semicircle taking turns talking about our “superpower.” Elli is guiding the conversation, having spent months with all of the students, she knows them intimately — even though she picked up on their superpowers the day she met every single one of them. Elli teaches that in order to discover your superpower, you must confront your greatest pain. Every student cried that day, including me.
I went last. I started to talk about my greatest pain in life: my brother’s death. He died of an overdose when I was 17 years old. Tears streaming down my cheeks, I began to talk about how powerless I felt when I got the call. I tried to help him. To get him on the right track. But I failed him. My throat began constricting to the point where I couldn’t even speak anymore. That’s when Elli spoke up.
She was crying hard, too. She fiercely declared that I AM powerful, that my destiny is so special. That my voice is to be heard and that I am to empower others. I’m to help others discover their dominion and rule as a leader with love and grace. I’m to inspire and show others the untapped potential they have.
That day changed my life. Elli Milan was my mentor before then, and has been since. I’m eternally grateful for the guidance that she’s given and continues to share abundantly.
How have you used your success to bring goodness to the world?
Dimitra: I believe we are bringing good to the world every day. Our mission with Milan Art Institute is to inspire and push people to live out their true destiny. Our destinies reflect our ultimate desires and passions in life. The more people who say YES to living their dreams, the better the world will be.
Jake: Art is so powerful. All it has to do is transform one life and it’s a successful piece. If that one person goes on to share their transformation with others, the effect is exponential.
By sharing our art and the techniques we learn online with our 10,000+ students we’re able to compound that effect.
What are the “5 Things You Need To Thrive As A Couple”?
1. Always communicate everything, be vulnerable and share your heart
2. Be a good listener
3. Never leave an argument unresolved
4. Do everything in excellence, strive to be your best self
5. Your dreams are just as important as your partner’s dreams
When two people really love each other — true selfless love — they are unstoppable.
If you could start a movement that would bring the most amount of good to the most amount of people, what would that be?
Dimitra: This may sound crazy, but we’ve already started a movement. The name of it came to my mom in a dream she had: it’s called the Light Movement. Art is a very powerful vehicle to bring transformation to the world. Art prophesies our future and we encourage our students to paint hopeful messages, positivity, light, beauty and to create the world they want to live in. The Light Movement is bringing more light into the world through beautiful artwork.
Jake: The art that’s coming out of this movement is unlike anything you’ve ever seen before. It’s dethroning the establishment that seeks to promote dark art and is instead championing beauty.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
Jake: “Reach for the stars, so if you fall, you land on a cloud.” — Kanye
This lyric has stuck with me since I was a kid. It has reminded me to strive for greatness on all occasions. The crazier the dream, the better.
Dimitra: “Faith over fear.” Throughout my life I’ve experienced what happens when you have strong faith in something, even when you can’t see or hear anything. Miracles have happened. One of the most powerful events in my life is how Jake and I came together. It’s a long story so I suggest you read our book when it comes out.
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?
Dimitra: I would love to have breakfast with Elizabeth Gilbert. Her book Big Magic was very inspiring for me and gave me a whole new perspective on artists. I would really love to connect with her one day!
Jake: I would love to get to know Kanye West. My mom had a CD of Graduation and every day she would play “Good Morning” when we got into the car to go to school. It never got old.
Nowadays, I love how he’s transcending the boundaries of art and pursues anything that he puts his mind to. I also relate to his story on a deep level: he overcame drug issues, found God and became a new man. Same here. But really, he just has an interesting mind. He seems to process information dimensionally, rather than linearly and I think that would lead to a fascinating conversation. Side note: I’ve actually painted Kanye before.
How can our readers follow your work online?
Dimitra and Jake: You can keep up with Milan Art Institute on Instagram @milanartinstitute, or follow our personal Instagram accounts @dimitramilan and @ohthatsjake.
Thank you so much for joining us. This was very inspirational.
Lessons from a Thriving Power Couple, With Dimitra Milan and Jake Dunn of Milan Art Institute was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.