Interested in starting your own entrepreneurial journey in web design but unsure what to expect? Then read up on our interview with Joshua Dale, Lead Developer of Olive Web Design, located in Derby, KS, USA.

What's your business, and who are your customers?

Olive Web Design is a web design and development agency that focuses on helping small businesses save time and make more money by optimizing their website around producing revenue and then completely managing all aspects of their website for an affordable flat monthly investment.

Tell us about yourself

I became interested in web development while serving in the Air Force. After my service, I earned a B.S. in Computer Science at the University of North Dakota. In my first semester there, I accidentally got a job as a web design intern. I went into the Office of University Relations to ask the web designer, Shacarah Gagnon-Kvale, some questions about being a web developer, and she thought I was there for an interview. She was promoted a couple of years later, and I took over her position, and that is how I began my professional web design and development career.

Over the years, I worked for three different agencies while also freelancing. One thing I observed is the cyclical struggle of small businesses having to fork over a large sum of money up front to build a website, then attempt to learn the system to update their own website, and ultimately come back to the creating agency frustrated and requesting that agency to make the changes only to be charged a painful amount in the end. Communication and relationship eventually broke down, and the small business would end up looking elsewhere in hopes of a better solution.

This is why in 2019, I leveled up from freelancing and started Olive Web Design to address these struggles. With Olive Web Design, I address these hurdles by:

  1. Waiving the cost to build the typical small business website when that company subscribes to our services for at least one year, therefore no high upfront cost.
  2. Managing every aspect of the company's website for an affordable flat monthly investment, thereby encouraging communication, fostering a good relationship, and eliminating unwanted additional charges.

What's your biggest accomplishment as a business owner?

I think that Olive Web Design is making a huge difference for small business owners. An effective website is half of the digital marketing battle. Just having a website is no longer enough. It is crucial that a small business website is strategically built to produce sales, generate leads, and bring customers to a business's storefront or enlist their service. Most small businesses go it alone largely to save on cost. In doing so:

  1. They sacrifice precious time that could be used to grow their business.
  2. The effectiveness of a website specifically built to produce sales, leads, and interaction.
  3. Expose themselves to lawsuits for not being ADA compliant
    Olive Web Design removes the large cost barrier and addresses all three of these issues and more. So my greatest entrepreneurial accomplishment has been to provide a way for other small businesses to succeed online.

What's one of the hardest things that comes with being a business owner?

What I find to be the most challenging is managing the balance between working in the business vs. on the business is tough because there are no. I enjoy both, but being a creative, problem-solving person who has so many things that I want to develop to help people out technologically, often, the business development and management tasks fall by the wayside.

Taking time to quantify everything I do is at the top as well. While there are specific things that are unique to what I can do and how I express me, almost everything is something someone else can do. If I want my business to grow so I can become hyper-focused on the things I want to create, then I need to have policies and procedures in place so someone else can take care of all the other details of the business. It is crucial for a ship to be able to sail itself. This gives business owners the freedom to sell their business, removes any concern should they be unexpectedly unable to work in their business for a season, and gives confidence that their business is secure.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

  1. Have a reliable form of passive or flex income. I would not have been able to sustain my venture had it not been for a rental portfolio and side jobs.
  2. Leverage everything you can. I took out two HELOCs and had about a dozen high credit cards.
  3. Calculate the bare minimum of what your business will have to make to sustain itself for five years and set your target to ten times that much. The first two tips are meant to temporally make up the difference when the business falls short and provide the feeling of a somewhat steady income.

Where can people find you and your business?


If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

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