We caught up with the brilliant and insightful Sean Dirolf a few weeks ago and have shared our conversation below.

Sean, appreciate you joining us today. We’d love to go back in time and hear the story of how you came up with the name of your brand?

I came up with the Brand name ITSOKAY (one word) in the Fall of 2017 in the bedroom of my parents house in San Diego California. I was 20 Years old at the time pursuing a Degree in Computer Engineering while working a full time Job in a corporate office as a Talent Coordinator. While at the time, the money was great for my demographic, I felt like I wasn’t fully satisfied with where I was at in life, granted I was in the process of obtaining a degree that would allow me access to do what I thought was my life goal; Computer Engineering, something still felt off. I soon realized at my Monday to Friday 9-5 job that even if I obtained my degree, I didn’t necessarily like the work culture of going to the office Monday to Friday, sitting in traffic to and from work, only having 2 days off on the weekends which didn’t even feel like days off because I was handling all the stuff I put off during the week because I worked full time. The normal work culture just wasn’t for me… One day as I was sitting in my car trying to take a nap during my 30 minute lunch break (something I also didn’t like) because of the reckless choices I made during my early 20’s, I had an epiphany. I said, “I wan’t to make money when I sleep” as my discomfort grew in my traditional workplace, my burning desire to financial freedom began.

As someone who has heavily been into underground automotive culture from a young age, I have always been interested in tinkering, modifying, and all things revolving cars and the culture surrounding it. As many other car enthusiast know, not everything goes as smoothly as we would like. Cars break, law enforcement treats you like a criminal, car parts are hard to find and when you do/if find them they are EXPENSIVE to obtain, and the car scene isn’t the most welcoming at times…But to me, my one response to that is ITSOKAY. At the time I didn’t realize this would be the whole idea behind my business: to Pursue Life’s Content no matter what cards were dealt your way. This is what ITSOKAY embodies. Not just automotive related topics, but my life and everything surrounding it as a whole.

I sat in my room for countless nights trying to think of ways to pursue my newly acquired life goal of, “making money while I sleep” this lead me to the decision to make a E-Commerce type of business, a business that runs on the internet, always open, to anyone, anywhere, at anytime. During this time, Social Media E-Commerce businesses were still relatively new. Being the Millennial I am, I heavily used social media platforms like Instagram and Facebook. As my unintentional desire to grow my following in the automotive niche through these social media platforms came about, I thought this would be the perfect place to showcase my new brand that embodies everything my life revolved around. Thus, from idea to fruition, ITSOKAY was born.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

My name is Sean Dirolf. I am a creative who is pursuing financial freedom through entrepreneurship. I got into my industry through my lifestyle hobbies, cars, design, streetwear fashion, nightlife culture and everything revolving around those subcultures. My streetwear brand ITSOKAY started off as a bridge between the two subcultures of underground automotive lifestyle & streetwear fashion. While still heavily focused on underground automotive culture & streetwear fashion, ITSOKAY has expanded its offerings as it encompasses a mirror of my outside lifestyle influences as a whole. ITSOKAY is unique in that it does not follow any trends in its respective niches, rather it sets to push the envelope by developing and pioneering high quality, unique takes on streetwear clothing, car styling accessories, and novelty items. I am most proud of the influence and trends my car styling accessories, clothing and novelty items have on the world, one item in particular I am proud of is my ITSOKAY Edge Lit Vanity Covers, which revolutionized the car scene by bringing a new spin to the boring regular license plate frames seen on cars.

Can you talk to us about how your funded your business?

I started ITSOKAY on a measly $50 and a dream. The first thing ITSOKAY sold was die cut stickers. I bought vinyl off ebay, went to a friends house after my 9-5 job and used his vinyl plotter to make my first ever stickers (shout out Damian, @TheMagicSpoolBus) Shortly after I sold all those stickers and perused other designs to add to the collection. That $50 soon turned into $300 and I was able to buy a used vinyl plotter of my own that I got off craigslist. Once I obtained my first vinyl plotter, it opened up a new door of opportunities. Everyday after work I would cut, weed, and pack vinyl stickers that I would sell to my friends all over the United States via Instagram posts, stories. I then saved up enough money to get a E-Commerce subscription, make my first E-Commerce store and then fund my next project, my first clothing piece. Soon after that intial $50 turned into a few thousand by repeating this process over the next year. During the same time I also had a side business by making other brands vinyl stickers to fund ITSOKAY. Once I had enough capital under my belt, I started upping the quality on all things and made my first car accessory the Vanity Cover, which was an instant hit and sold out so quickly I wasn’t able to keep up with demand for the first few months of production. After that the rest was history and ITSOKAY was fully self sufficient after that.

Let’s talk about resilience next – do you have a story you can share with us?

While perusing financial freedom is one of the most satisfying things I’ve set myself to do, it was no easy task. Till this day I continue to learn, adapt, and overcome the many challenges of running a business has. When I first started ITSOKAY, I was a full time student , worked a full time job, and on top of that took on the challenge of running a business that would soon dictate my future to come. As time went on I had to make choices that have shaped who I am and my life today. I dropped out of college in pursuit of success in my business, I have lost relationships due to my dedication and laser focus on my business, I have even lost myself in the process from prioritizing the success of my business. All these challenges I had to overcome as time went on and they have shaped who I am today, how I do business now, and what choices I will make in the near future. There have been so many times where I have wanted to give up, or think that this won’t amount to anything significant, but these small setbacks are the biggest learning lessons life has to offer. While I am still on the pursuit to definitive success, it won’t be set back by victim mentalities, or excuses, and I feel like for the amount of time and experiences I have been through while running my business It has only made me a stronger person as a whole. Patience is a virtue and once that is mastered, you will be set free. I am still on that road to mastering it.

Contact Info:

• Website: https://ITSOKAY.GG
• Instagram: @ITSOKAY.GG
• Facebook: @ITSOKAY.GG
• Twitter: @ITSOKAGG
• Youtube: @ITSOKAY.GG (Content coming 2024)
• Other: All Platforms @ITSOKAY.GG

Image Credits
Adin Penner (@Sexiswork) Nathan Fong (@Nates__Motel)