Today we’d like to introduce you to Kyle O’Shanna.
Thanks for sharing your story with us Kyle. So, let’s start at the beginning and we can move on from there.
When I was 18 years old I started working for my neighbor who owns an asphalt maintenance company while also going to community college full time at night. It was the hardest and dirtiest work I had ever done, but I was making better money than all of my friends and even some people my parents’ age. I stayed at that job for 3 years doing mostly asphalt seal coating and asphalt crack filling, along with some general labor. I would sacrifice my summers while all my friends were having fun and going out to be able to wake up at 5a.m. to work all day making great money. I worked anywhere from 40 to sometimes close to 70 hour weeks and started to see the monotony and difficulty of doing labor every day in such a competitive industry. I also learned a valuable lesson about stretching myself too thin. After about a year and half of balancing a full time job and a full time course load at school, I decided to stop attending college to allow myself some breathing room, and I didn’t see much harm in it at the time as I didn’t know what career I wanted to go into anyway. My boss and all of the people I worked with were very nice to work with, but it was still a very competitive field with a lot of tight deadlines, so I didn’t get much time off to spend with family and friends. There also wasn’t much room for growth at that company, so in a way I found myself working with no goal in sight. It was a very difficult decision for me to make after 3 years of working there to quit a steady job that was paying me a solid union wage, knowing I had no job lined up next, and no degree to help me find one. All I knew at that time was that I wanted to have more freedom with my time and do something that has more meaning to me. In the months following me leaving that company I did a lot of thinking about where I wanted to go next, and who I wanted to work for. I thought about a lot of things; bar-tending, working at a restaurant (again), a landscaping company who had offered me a job as a foreman, and quite a few more, but nothing stuck with me and I didn’t see myself happy at any of those places long term. After brainstorming for a few months and networking with the right people, I started getting into entrepreneurship and business. I was fascinated with the idea of starting something from scratch and feeding it, and watching it grow into something beautiful and successful. With the help of a friend, I got the idea to start a painting company. Low start-up cost, subcontract all the work to keep things simple and cheap, and a relatively easy service to get involved with. I did know a decent amount about painting at that time as I painted for a while on the side and for my own family, but the rest was up to research. I looked up anything and everything I needed to know to start a business, about painting, about dealing with people, and most importantly about goal setting. I learned that I could never grow the way I wanted to without setting goals, both short term and long term. I set a goal to create a LLC, and I did it. I set a goal to subcontract my first job, and I did it. I set a goal to keep a crew of guys busy for a week, and a month, and I did it. I continue to set short and long term goals for myself and for my business, and those goals are my biggest driving force in running a business at 23 years old. I plan to make enough money to hire employees to help run my company more efficiently and successfully, and eventually have enough money to work on philanthropic endeavors. I am passionate about clean eating, healthy living, fortifying the environment, and helping people live in harmony, to name a few things.
Overall, has it been relatively smooth? If not, what were some of the struggles along the way?
Running a business is never a smooth road as any business owner will tell you. While I am only 23 years old, I have definitely experienced my share of hardships while starting and running my company. One of the hardest parts about the journey was the beginning. It was very difficult training myself to think I would be able to start a business and run it successfully, and I thought a lot about people not taking me seriously because of my age. As it turned out I had no problem with starting the business and with a lot of help from my father and filling out some paperwork, I was up and running. And as the saying goes; age is just a number. My other biggest struggle was stress. I was constantly worrying about things going wrong and allowed “what if” statements to run through my head. What if I fail? What if something goes wrong on a job? These thoughts along with a busy and stressful life led me to worry and doubt my company’s success. I had to learn to relax, to be more organized, and to only think positive, constructive thoughts. This was and still is the best way for me to keep stress away, and to keep running Diamond Deeds successfully. To circle back to my first sentence, running a business is never a smooth road, but there are a lot of tools and strategies that can be utilized to help get over the speed bumps and around the obstacles. A positive mindset is perhaps the single most important thing to help me get through my struggles, because I know they are only temporarily, and hopefully occur rarely.
Alright – so let’s talk business. Tell us about Diamond Deeds – what should we know?
Diamond Deeds started as an interior painting company. Now, we perform services including interior painting, exterior painting, staining, drywall work, light carpentry work, some smaller remodels such as kitchens and bathrooms, electrical work, and more! Diamond Deeds is known as a painting company, but many times after clients see how well the painting work is performed and how friendly the workers are, they want more work done! I am very proud of my 5 star reputations on multiple platforms including yelp, home advisor, and houzz. I maintain a good reputation on the internet as well as in person. Many people are willing to refer work due to how pleased they are with the results of what we’ve done. I am also proud of the fact that I have never walked away from a job unless I knew the client was 100% satisfied, or that I did my absolute best to give them a great finished product. Mistakes and misunderstandings are a part of life, but I always do my best to fix the situation and make sure the client is happy with the results. What sets me apart from others would be my age and enthusiasm in dealing with people initially. More importantly I promised myself when starting Diamond Deeds to make client satisfaction my highest priority, and to never cut corners. Also, I have been fortunate enough to find friendly hard working professionals to work for me, and I hear nothing but compliments about them from clients.
Any shoutouts? Who else deserves credit in this story – who has played a meaningful role?
My parents deserve a lot of credit. It had to have been difficult for them to watch me quit my job with nothing else lined up, only to hear that the next thing I want to do is go into business for myself. My dad is in accounting, so he helped me from the beginning with paperwork, filing forms, helping me understand the business world, and much more. I have to thank the rest of my family as well. My older brother and sister, younger brother, step sisters, step mom, and even extended family are all very supportive of what I am doing. I also must thank my very supportive girlfriend for allowing me to dream big and do things that no one else our age is doing, and for being there on the days that there were bumps in the road. I am also fortunate enough to have close friends who give me feedback on my ideas and decisions, and continue to challenge me and present new ideas for me to implement with my business.
Contact Info:
- Website: www.diamonddeeds.com
- Phone: 2245778032
- Email: kyleoshanna@gmail.com
- Facebook: facebook.com/diamonddeedspainting
- Yelp: https://www.yelp.com/biz/diamond-deeds-des-plaines
- Other: https://www.houzz.com/pro/kyleoshanna/diamond-deeds

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