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Mark Mastrandrea & Jeff Cole of IKONICK: “Authenticity”

Authenticity. We live in a digital content age. You have to be completely transparent with everyone about everything in order to succeed. People will always find out the truth so you can’t afford to hide. Relatability. Aim to encapsulate familiarity and humanize your brand as much as possible. No one is going to relate to what […]

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Authenticity. We live in a digital content age. You have to be completely transparent with everyone about everything in order to succeed. People will always find out the truth so you can’t afford to hide.

Relatability. Aim to encapsulate familiarity and humanize your brand as much as possible. No one is going to relate to what you have to say if they don’t relate to you first.

Emotion. This can take form in many ways; add humor, visuals, content. You have to tell stories that trigger emotion and help form a meaningful connection with your audience.


As a part of our series called “5 Things You Need To Know To Create A Very Successful Lifestyle Brand” I had the pleasure of interviewing Jeff Cole & Mark Mastrandrea, Co Founders of IKONICK (https://ikonick.com/).


Jeff Cole, Digital Artist & CoFounder of IKONICK — Instagram: @Cole

Jeff Cole is unlike anyone out there. Born in the Michael Jordan era of Chicago, he developed an early love for diverse cultural genres emblematic of his hometown; sports, sneakers and visual art. The point of collision between the three is where Cole’s art has found its sweet spot, which features masterful mashups of your favorite comic book heroes, sports stars and hype-worthy sneakers in otherworldly settings. His consistent output of unique content and hustle mentality have attracted attention from some of the biggest brands in the world, and garnered a cult-like following on Instagram. The Los Angeles based artist is also the co-founder of IKONICK, a multi-million dollar art brand backed by entrepreneurial giants, Gary Vaynerchuk and Scooter Braun.


Mark Mastrandrea, CoFounder of IKONICK — Instagram: @MarkBrazil

Mark Mastrandrea grew up in Long Island as a high-level athlete and has always been an all round competitor with a passion and goal to simply win at life.

Mastrandrea started his career as a salesperson but quickly grew into a marketing guru by consistently acquiring skills from any form of hands-on experience he could get. For many years he worked as an expert consultant to myriad businesses, operating with an entrepreneurial mindset and helping identify unique opportunities for growth.

In 2017, Mark CoFounded IKONICK with long time coworker, roommate and self proclaimed brother, Jeff Cole. IKONICK is a direct-to-consumer canvas art brand on a mission to motivate and inspire people around the world through visual storytelling. Mark’s extensive experience in business and brand building up until that point led to explosive, early success and ultimately landed strategic investment from entrepreneurial icons, Gary Vaynerchuk and Scooter Braun. Today, IKONICK is a multi-million dollar brand with three product divisions catering to men, women and kids who live to inspire, and be inspired. Business partner Jeff Cole describes Mastrandrea as “the most persistent and strategic person he’s ever met in his life.”


Thank you so much for joining us in this interview series! Can you tell us the story of what led you to this particular career path?

Mark: You know it’s funny, people look at our company and they think we grew so quickly and IKONICK was an instant success. Quite frankly, we did grow fast and we have been successful, but what people don’t see and most people don’t know is all the struggles and the epic amount of failures we both experienced for ten years before we started.

Jeff: Mark and I worked together at three different companies before starting IKONICK where we felt underutilized, under-incentivized, underpaid. We knew we had the skill set and the hunger to do great things but it never felt right working for anyone other than ourselves.

Mark: So IKONICK really came to be as a case of hard work and preparation meets opportunity. We were both broke, living and working together in Carlsbad, San Diego. I had started managing an artist part-time and quickly recognized the whitespace between limited market supply and mass consumer demand in fine art. Jeff has always been really great at seeing where the puck is going and he knew in those early days of Instagram that social media was going to be a huge platform for artists and creatives but also for business and marketing.

Jeff: Yeah, I remember when hashtags started, that was a huge eye opener for me. The fact anyone in the world could see your post if they searched or clicked on a hashtag you used was wild, and this was back when the hashtag art had something like 20 posts. That’s when I knew it was time to start something. So we founded IKONICK based off that knowledge of white space in fine art and an early understanding that social media was going to be the future of brand marketing, discovery and distribution.

Mark: We paid a 19 dollar hosting bill to Squarespace and the rest is history!

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?

Mark: For the first four months, IKONICK was a true side hustle. We were working early mornings and late nights around full-time jobs and it was just the two of us with a shared passion and dream to build something special. We got so behind on orders those first few months and we had to fulfill them all ourselves in our very limited free time.

Jeff: We would literally have to input every single piece of data manually; emails, phone numbers, addresses, everything. Mark and I would have contests to see who could complete an order the fastest and take power naps in between into the night.

Mark: We even had to upload the art files and sometimes we would mess up and people would receive random pictures of stuff saved on our desktop! What did we learn? When sales are consistently good, get a production partner.

Is there a particular book, podcast, or film that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

Mark: Book has to be Good to Great by Jim Collins. It gave us infrastructural vision for the company; everything from management to hiring to culture and facing the hard realities.

Jeff: Podcast is for sure Naval: How to Get Rich (without getting lucky). In general, it taught us a lot but more specifically, it verified our thoughts on life strategy.

Mark: Movie would have to be Social Network because we watched it on repeat during the early days of IKONICK. We would just have it on in the background while we were working early mornings and late nights.

Jeff: That movie also inspired our IKONICK x Monopoly collection. There are a lot of similarities in how we built and established our business.

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

Mark — Always and only, make new mistakes, as fast as possible, once”

That’s an original quote that I live by. You can’t be afraid to fail. It’s about constantly making micro failures. As long as they’re not fatal and you’re learning, in the long term you will win.

Jeff — “Outwork everyone”

I’m a big believer that work ethic eliminates all fear. When you know why you’re doing what you’re doing, and you know how hard you’re willing to work for it, there is no room for doubt, competition or fear.

For the benefit of our readers, let’s define our terms. How do you define a Lifestyle Brand? How is a Lifestyle Brand different from a normal, typical brand?

Mark: I think lifestyle brands differentiate by offering an extra layer of authenticity and insight into the actual life of the company.

Jeff: You have to be personally relatable and have an open line of communication with your consumer.

Mark: Exactly. The core DNA of the brand must resonate and bleed through to all things like communication, content, core values, and everything you do.

What are the benefits of creating a lifestyle brand?

Mark: That’s an easy one… Work isn’t work, it’s just life.

Jeff: Mark and I have lived together since we started IKONICK. We love what we do. Our life has become our brand and that not only makes decision making easier, it also makes everything we do more authentic and ultimately, more successful.

In your opinion, what is an example of a company that has done a fantastic job building a believable and beloved Lifestyle Brand? What specifically impresses you? What can one do to replicate that?

Mark: I think we’d both say Yes Theory and its clothing brand, Seek Discomfort. The founders Ammar, Thomas and Matt are the epitome of authenticity shining through a brand.

Jeff: At its core, Yes theory is just a bunch of guys going outside their comfort zone and creating dope content, but it led to the existence of a passionate, like-minded community. That community has become their brand and now manifests itself in apparel, consumer goods and everything they do.

Mark: It all goes back to the idea of doing what you love, being honest, and being committed to work harder than anyone else to go after what you want.

Can you share your ideas about how to create a lifestyle brand that people really love and are ‘crazy about’?

Jeff: Find a business opportunity that is aligned with your passion and be willing to put in the time and effort to make it a success.

Mark: It’s true, you have to put in a crazy amount of effort, but you also have to start small and celebrate the small wins along the way. We still personally call our customers all the time, we champion them and whenever possible, develop one to one relationships. If you want consumers to love and believe in your brand, you have to love and believe in them too.

What are the common mistakes you have seen people make when they start a lifestyle brand? What can be done to avoid those errors?

Mark: Underestimating the value in customer feedback and insight. All the answers you need lie with the customer. Put yourself out there and talk to as many people as possible. The moment Jeff and I became more vulnerable was the moment our audience started resonating with us.

Jeff: You have to listen to your audience. Social media is the most valuable tool for instant connection and constructive criticism. In order to get better, you have to get curious, be willing to learn and most importantly, adapt if needed.

Let’s imagine that someone reading this interview has an idea for a lifestyle brand that they would like to develop. What are the first few steps that you would recommend that they take?

Mark: I can’t stress this enough; start small. Find your niche, and then find a niche within that niche.

Jeff: You have to develop your identity based on the attributes of your audience. You can’t do that if you’re trying to be too many things at once.

Ok. Thank you for all that. Here is the main question of our discussion. What are your “5 Things You Need To Know To Create A Very Successful Lifestyle Brand” and why? (Please share a story or example for each.)

  1. Authenticity. We live in a digital content age. You have to be completely transparent with everyone about everything in order to succeed. People will always find out the truth so you can’t afford to hide.
  2. Relatability. Aim to encapsulate familiarity and humanize your brand as much as possible. No one is going to relate to what you have to say if they don’t relate to you first.
  3. Emotion. This can take form in many ways; add humor, visuals, content. You have to tell stories that trigger emotion and help form a meaningful connection with your audience.
  4. Team & Company Culture. Business in its simplest form is a bunch of people doing a bunch of different things. You have to hire the smartest, hardest working team, and you have to get everyone aligned on your company vision in order to execute at the highest level.
  5. Relentless Work Ethic. This applies to any business and any brand. You have to be committed to outwork everyone or be willing to accept failure. It’s that simple.

Here are our final questions. You are an 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.

Mark: Give more than you take. You should always provide value first.

Jeff: Give more than you take is one of our six core values at IKONICK. If everyone adopted this philosophy with everyone they encounter, the world would be a better place.

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, and why? He or she might just see this if we tag them.

Mark: I already know we agree on this, Naval Ravikant.

Jeff: He’s the wisest thought leader in the world.

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


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