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I Bought My First Business When I Was 25

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My newest series centers around entrepreneur stories and their journeys. This series has been so fun and I am floored by the amount of inspirational stories I’ve been able to feature, this one included. I hope that these stories help empower you in your own experience and journey (if you’re an entrepreneur or if you’re not and still want inspiration for something else you want to start in your life). This is an interview with Kevin of HomeDabbler.com who’s been running his own businesses since he was 25 years old (which is when he bought his first business). Read on for his amazing story!

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Tell us a little about yourself and your business.

I’ve been an entrepreneur most of my adult life. I bought my first business when I was 25 years old, an after-school child care facility. I ran that for five years and then founded Service Meisters, a full-service property renovation, repair, and maintenance service. I ran it for 10 years. I also have investment properties. 

My latest hustle is called HomeDabbler. I’ve taken all the expertise I earned in that decade fixing and maintaining homes and created a blog and merchandise store. It combines all the things I love and am good at. I not only show home projects, I explain the tools and techniques needed to accomplish them, something most DIY shows lack. 

HomeDabbler is a home for DIY enthusiast, gardening nerds, and chicken raisers like me. I plan to grow it into an influential blog, a TV series with national sponsors, and a full-on merchandise brand. 

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In this entrepreneur series interview I talk to Kevin from HomeDabbler who started his first business when he was only 25 years old. #entrepreneurstories #entrepreneur #smallbusiness #startyourownbusiness #businessowner #businesstips #sidehustle #entrepreneurlife #workfromhome
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What made you want to embark on this entrepreneurial journey and start your own business?

I remember thinking when I was working as an employee at the day care that I would eventually buy, “I’d like to run this.” I was 23 or so. I think you either are or are not an entrepreneur and it is in you from birth. It’s just in me. I have at least five new business ideas every day and nothing excites me more. 

What were you doing before? What made you want to leave that and do your own thing?

My first business, that day care, started as a college job. The owner wanted to retire and offered to sell it to me. After I closed the day care, I started Service Meisters immediately. I have a day job now with an engineering firm but HomeDabbler is one of my side hustles that I’m extremely excited about. 

I think entrepreneurs are essentially creatives. And there is nothing more creative than starting a new business from scratch – literally something out of nothing. It’s frightening, exhilarating, rewarding, punishing, the whole human experience. And to me, it’s elegant. You get up every day and provide value to the world or you go under. Simple, clean, elegant. 

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Starting a business is not easy. What was the hardest thing you faced when getting your business off the ground?

Finding good help. I never had trouble generating ideas, selling myself or my business, finding new customers, etc. It came natural to me. But I kept hitting a ceiling when my businesses grew to the point that I needed multiple employees. 

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Did you have any sort of savings that you applied towards getting your business up and running or did you take out a loan? Can you guide us through how that was like?

For my first business, I had an investor. I was young and eager, but didn’t watch my overhead closely enough and it slowly bled my business. I learned from that mistake when I started my second business. I paid for everything cash, carried no debt. I ran it that way for 10 years and closed it on my own terms. HomeDabbler is the same way. I’ll never get eaten by overhead again. 

That would be my biggest advice to new entrepreneurs – manage overhead or it will manage you. 

Also, they say that most first businesses fail, but second businesses succeed. That was true for me. Closing a business is heartbreaking, especially if you don’t want to. However, most people quit after that first failure. I suggest that you open a second business and see what happens. You’ll make better choices. 

How long did it take to actually start profiting from your business?

My second business, the one I started from scratch, was profitable within one year. I think this is because I ran it with no debt. I drove a crappy truck, wore a cheap uniform, kept costs down. That allowed me to hustle and gave me the space I needed to get it off the ground. The first year or two were tight, but then it took off. 

HomeDabbler is very new, I’m still building my online following and generating content and ideas. That costs me nothing but time. There is not profit yet but I’m laying the groundwork

What legal issues/road blocks (if any) you experienced during this start up period?

When I had the day care, I dealt with inspectors all the time, as day cares are highly regulated. I learned that I had to really know the rules for myself, because not all the inspectors did. I recommend that whatever industry you are in that you know your regulations like the back of your hand. It will save you money and keep you out of trouble. 

I’ve tried different business configurations – sole proprietor, LLC, C Corp. There are different legal and tax requirements for each of these. I recommend that you scrape some money together and consult with an expert about which is best for you. It will be money well spent. 

Also, get a bookkeeper. Doesn’t have to be a CPA – they’re expensive – but someone who is qualified to do taxes and books for you. It will help you avoid legal and tax issues. That will help you sleep better at night and allow you to focus on growing your business. 

What did you do in regards to finding health insurance and contributing towards retirement?

This is a tough one. Start-ups can and will take every dime you have in the early years. It took me years until I could start saving like I wanted and to have adequate health insurance for my family. It was a risky time. I frankly had to bumble through it, pay cash for some medical procedures, etc. 

I think this is one of the risks that entrepreneurs have to accept. You should save and have insurance, but I will tell you that it is tough early on, at least it was for me. I got there, but it took a while. 

Anyone can open an individual retirement account (IRA) and start contributing small amounts. I recommend starting as early as possible, even if it’s just a little. I started later than I should have. There are financial advisors that can help you. I recommend you use one. Don’t invest on your own, you won’t be good at it (unless that is your business).


Side note from iliketodabble: For your current retirement plan, look into something like Blooom. Blooom takes the confusion out of your retirement. For free, they look at your current 401k and see how they can improve it. After your analysis, Blooom will place the trades within your account for a low flat fee.


How do you find the time to still tend to your own personal life and needs?

Another tough one. Early on, I worked a lot. I remember a stretch where I didn’t take a vacation for six years. I’m not saying this is how you should do it, only that your business will take all your time if you let it. 

For me, the breaking point was when my daughter was born. I simply committed to make less money and spend time with her and my wife. I was less profitable during that period, but I don’t regret it. That is the choice you will eventually have to make. Even if you have great employees, no one will run your business as well as you. You’ll have to carve out a space for your life and other interests, but it will cost you. Just the way it is. 

What tools do you use and recommend to others to help manage your time, life and overall well-being while running a business?

The Google Now digital assistant and my Google calendar are a god send to me. I don’t have a great memory for appointments and daily chores, so I just tell my phone to remind me of things and it does. 

For me, managing my life and business came down to life timing. While my daughter was small, I kept my business small so I could have time. Now that she is 18, I can push into HomeDabbler and give it more of my time. I can make videos, blog, or design merchandise on the weekends when before I couldn’t. I had to wait for the right time in my life. 

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What is one book, online article or other form of inspiration that guides you through your day-to-day work?

There are two books that changed my business life and I recommend them to everyone: 

  • Good in a Room by Stephanie Palmer – She will teach you how to pitch your ideas to important people. You NEED this skill to succeed as an entrepreneur. 
  • Positioning by Al Ries and Jack Trout – Positioning your business properly is everything. Do it right and you will grow. Do it wrong and you will fail, no matter how hard you work. Simple as that. Read and practice this book. 

Tell us one way your lifestyle has changed since becoming an entrepreneur?

I’ve always been one so I don’t really know any other lifestyle. I will say that after about five years of business, I finally felt that I had control of things, that I knew how to do this. Maybe it’s the 10,000 hour rule, I don’t know. But after five years, things seemed to get easier. 

What are 3 tips you have for others who are thinking about starting their own business?

  1. Keep overhead down. You will be tempted to go into huge debt to get your business off the ground. I say you should resist this, even if it takes longer. I can tell you from experience what it is like to know that your business is slowing bleeding to death because your bills are too high. 
  2. Make up your mind to work like the devil for five years. I know lots of business books tell you to take time for yourself no matter what, to pay yourself first, to cultivate hobbies while your work on your business. This was not my experience nor the experience of any entrepreneur I know. Talking to my business friends, it took us all about five years of crazy work to reach a plateau where we could relax.
  3. You will be scared a lot, but we all are. Forget the myth that successful entrepreneurs have it all figured out. That is a social media lie. We are scared, we doubt ourselves. But we want to have our own business and that outweighs the fear. Do not feel bad for being scared or insecure, and it doesn’t mean you won’t succeed. 

Think back to a time before you had your own business. What would you tell the “you” that you were back then?

I would tell me the three things from the previous answer, especially the part about being scared. I know some super successful entrepreneurs and they will tell you straight up the same thing. I would tell young Kevin not to buy the lie that anybody has it all figured it. And I would tell me to get to work!

Thank you so much for sharing your experience with us! Any parting thoughts?

I appreciate this opportunity. As entrepreneurs we are competitive, but we also like to help those starting out. It’s a community. I’m proud to be a part of it. I hope my experiences helps and encourages someone. 

My HomeDabbler business is pretty new, but I’m shooting big on this one. Bigger than I ever have before. And just like 25-year-old Kevin, 45-year-old Kevin is nervous but excited. ☺

Entrepreneur Bio:

Head shot of Kevin from HomeDabbler
Head shot of Kevin from HomeDabbler

Kevin Elliott is a serial entrepreneur who bought his first business at 25 years old. He later founded Service Meisters, a full-service property renovation and maintenance business, which he ran for 10 years. His latest venture is called HomeDabbler, a blog where Kevin uses his deep experience to explain the tools and techniques that people need to do their own home projects. In short, HomeDabbler is a community for DIY enthusiasts, gardening nerds, and chicken raisers like him. 

Follow HomeDabbler on Facebook, YouTube and Instagram.

What do you think of Kevin’s story? Did you find his past experience educational and useful? I sure did! What questions do you have for him? What are some business ideas you would love to start?

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