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Image sourced from Luke Wessman social media

The Leeson Interview Series

Luke Wessman, a man of the modern world. His tale is one of grit, passion, and business. A story that speaks true to the ideals of many millennials that want to be their own boss, Wessman has generated an image of authenticity, and creativeness while becoming a self-made businessman.

We began following Wessman sometime ago, and watched as he rapidly converted a business and personal following into a strong social media presence. Wessman is the banner bearer of a culture that looks inwards to foster a more wholesome ideal of modern masculinity.

Growing up in a tough neighbourhood of Oceanside, California, Wessman is no stranger to hard work. His creative businesses have flourished thanks to Wessman’s ability to create a brand that resonates with millennials. A practical preacher of style, integrity and working hard, he is fast generating a substantial following. The business portfolio of multiple tattoo studies, a merchandise line and a design portfolio that is sought after by a multitude of international corporations.

Wessman has worked with major names such as Chevorlet, Tommy Hilfiger, Spotify, and has tattooed a plethora of notable individuals including Matt Holiday (All Star MLB player), Travis Barker (drummer, Blink-182) and Christopher Lloyd Hayden (drummer) fromFlorence + The Machine. Wessman has also appeared in alternative TV shows such as NY Ink, Ink Master, and Miami Ink.

What do you buy yourself as a treat or pick-me-up?

LW: A fresh pack of white T-shirts.

What is the most fulfilling project you’ve worked on to date?

LW: The project I’m most fulfilled by is a secret — I’m working on it now. Collaborating with Chevy and Tommy Hilfiger were pretty cool, too.

If you were the U.S. Treasurer, what policy would you put forward?

LW: This may be the least impactful answer, but I would change the money to be more like Australian Money; I love how colorful their waterproof bills are — like art.

You have all this experience in tattooing but would you say it’s your biggest passion?

LW: My biggest passions are the people I meet everyday, the clients and their stories. I am genuinely invested in everyone that sits in my chair, and I’m lucky to be meeting people from all walks of life — huge perk of the profession.

What was your first job?

LW: My first job was at 14 as a beekeeper: $5/hour and constantly stung — I loved that job!

You had a creative father growing up but you left home at the age of 15, before most of us have even finished growing up. Then you entered the world of gangs, art and tattooing with Dave Gibson, which lead to a career and signature on the world. Do you believe your youth was the most defining part of your life, always surrounded by creativity and survival, or were there other factors to come later in life that gave you a true sense of purpose?

LW: I didn’t have a safety net growing up — no allowance, no get out of jail free, so I had no choice but to be responsible, hold my self-expectations high, and create and meet challenges I set for myself to stay driven. By overcoming the obstacles I faced as a teenager, I found my dedication and drive. It wasn’t until I hit my 30s that I was able to reflect back and see how definitive those challenging years were in my development as an artist and businessman.

Family is evidently an integral part of who you are and you have built a family around yourself with fellow artists and with the Freemasons. Is it this love for your family that gave you your moral integrity or the family members themselves that directed your values?

LW: It’s weird — I can’t pinpoint a specific source for my moral compass — I grew up with a lot of mess around me and I was always able to tune out the outside noise and focus on my inner dialogue. I guess I learned some respect from the gangs I grew up around — being a man of your word and things like that. Today, though, I look to friendships and podcasts and readings to enhance my mindset and values.

Your values and moral integrity form a core part of your brand but so do tattoos, gangs, and grit. A rags-to-riches story unfolding through your life and a modern image of duality, you inspire thousands of people around the world. Have you always worn your values on your sleeve and how important would say ‘brand’ is in building success?

LW: As a kid, I was pretty quiet and shy — and although I had a strong value set, I didn’t jump up on the soap box and share. My friendships as a young man really reinforced and encouraged open dialogue about what’s important in life. I have some super deep friends. As I’ve gotten older, my platform has changed, and I’ve been able to share my creeds with my followers. I’ve had a great relationship with social media and a lot of success with sharing honesty. For me, I realised my story is what made me me. I decided to run with it instead of hide from it. My “brand” is authenticity — it makes it super easy to participate when you’re being honest.

Success is a fairytale that lots of people dream of but you are pursuing it. Do you believe in the idea of overnight success or do you think that it takes ten years to build ‘overnight’ success?

LW: I believe in both. I think it happens differently for everyone depending on their paths and pursuits. I always say luck is what happens when preparation meets opportunity — sometimes it takes an hour of preparation, and sometimes it takes a decade.

You’ve said that your success has come from inspiration to not be broke and to support a family. Is this where the ideas to bring out your own merchandise line and owning a tattoo parlor came from or are they by-products of your non-stop creative mind?

LW: My various endeavors over the years — owning Lucky’s Tattoo in San Diego, my merchandise, books, etc — have definitely been a by-product of my head-down hustle. At this point in my life, however, I’m focusing on trying to build systems that work for me and make me money, rather than straight grinding for the next 40 years. Trying to work smarter, not harder these days.

Owning Lucky’s Tattoo must have been a challenge and a blessing. What do you find the most challenging aspect of business ownership?

LW: Owning Lucky’s Tattoo was a great experience, but incredibly challenging. The battle between the business and the artistic mind is never-ending. The most challenging aspect for me was employee management — trying to handle different personalities and levels of professionalism was a constant challenge for me.

The media love you: you’ve been nominated as the №1 hottest bearded tattoo artist and you’ve built a global image through the use of social media, TV and print. For you, is the media an outlet for your creativity, an avenue to inspire integrity or a place of business?
LW: All three, and its seems if you can make it all three you’re really doing it right.

The hours a tattoo artist works are truly grueling and you have to work in some interesting areas of people’s bodies while they are in pain. How do you compare the challenges of tattooing to the challenges of financial success?

LW: Do what needs to get done, and do it with integrity.

You are a mentor to thousands of people and a source of inspiration to become ‘Self-Made’. What advice could you give someone who has no idea of the direction his or her life is takng and is facing an uphill battle to not be broke?

LW: Stay alert and motivated, keep pushing, create enough friction and there will be a fire.

To touch on politics, we saw that you support Bernie Sanders, a man of the people who shares a similar story to you. He’s Self-Made from Brooklyn and voted ‘no’ on financial deregulation, voted ‘no’ on the Iraq War, and most recently instigated an audit on the Federal Reserve. His policy stances can all be seen as positives as we now have the gift of hindsight post-GFC and post-Iraq. What is it about him that appeals to you?

LW: First of all I must admit I’m not too politically active. Sometimes, I believe the system is almost beyond repair — but there’s something about Bernie that makes sense to me. When I listen to him talk, I feel like someone is actually cutting the bullshit. I really feel like he’s trying to help us.

For anyone wanting to get into tattooing or owning their own tattoo parlor what advice would you give them?

LW: Pay dues first. If you want to get into tattooing you must immerse yourself in the craft. Start by getting heavily tattooed. If you think you want to own a shop, work in a few for a while and be honest with yourself about whether the financial and mental stress is worth it. I’ve found great peace in walking away from a day’s work and not worrying about the burden of business ownership.

Lastly, what do you think is the most important thing for a young person to do with their money?

LW: I’m still trying to figure it out. Stock market? I don’t know. Learn how to make it make you more; having it under a mattress is not enough. Right now I’m focused on building things that make me money — not focusing of a piece of the pie, but on the pie maker.

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