We were lucky to catch up with Amy Oostveen recently and have shared our conversation below.

Amy, thanks for joining us, excited to have you contributing your stories and insights. Are you able to earn a full-time living from your creative work? If so, can you walk us through your journey and how you made it happen?

Twice, I have been able to earn a living from my creative work – aka starting my own business. The first time, I started a women’s only fitness studio, I imagined a new hobby being a fun, part time business. It grew to three studios and a license to Franchise within 6 years. At one point, I had over 50 staff members reporting into me as the Owner. A major milestone that I hit in that business was when I duplicated to two studios. When I learned how to duplicate my efforts, my business doubled and tripled within a year.

After 12 years in that business, I decided to move on to the next chapter of my life and slow down. I sold my business in May of 2024 and decided to focus on my family and homeschooling my kids. As I began to get my business ready to sell, myself and my 13 year old son, started a new business together: The Dog Bus!

Three years ago, we began walking dogs and watching dogs out of our home. My son began communicating, learning about money and we found a great way to tie this directly Into our homeschooling program. As we got busier, we explored more options on how to balance all of our jobs. We explored numbers and decided to build a business off of our dog walking business. In December of 2023 we bought a bus. On January 29, 2024 we ran our first route of our dog bus business called Wagging Riders.

Today, we have over 50 customers/ just a short six months later.

Once again, what was once a hobby, turned into a profitable business for my little single mom family of three (my two kids and I) to run together. We have integrated so much real life schooling and have made memories galore working, laughing and sharing together.

Amy, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

I got into both of these industries by loving something so much that I wanted to make a living doing it. I’m actually a terrible employee and I don’t like following directions. I like to create rules of my own. I’ve been that way my entire life. I grew up on a golf course selling golf balls and peanut butter and jelly sandwiches. I quickly realized that I was good at sales and upgrading and that I could make a business literally doing anything.

What sets me apart from other people that don’t run businesses is one thing: I decided to take action and do it. When I started bout of my companies, people said to me – oh I’ve always wanted to do that! – I have been waiting for something like this!

My work has come from the heart. I put my customers first and create a loyal community that comes together and works as a team. Last year I wrote a Chapter in a best selling book about community and how it’s so important with your staff, your clients and yourself as an Owner.

All of this comes with making a ton of mistakes. As an entrepreneur and in life, you can’t be afraid to fail. It’s not about being perfect, and it’s not a bad thing to make mistakes. What matters in the failing moments is how you come out of them – as a person, as an Owner, for me, as a mother. I have failed over and over and over. But I have CHOSEN my path each time after.

I’m really proud to have brought my kids along with me as I have gone through challenges, struggles, failures and successes. They have learned so much and the best compliment I get in my life right now is: Wow, you have really awesome kids.

Have you ever had to pivot?

In 2019, my business was doing over a half a million dollars in sales and had the highest year since we opened in 2013. In 2020, we were on pace to beat our 2020 numbers and then the world shut down due to COVID. I lost everything.

By the time we were allowed to reopen with smaller numbered classes, I had lost out on over 400k in sales.

I chose to rebuild my company and due to the systematic approach and community built in the first few years, we were able to climb back to strong numbers and keep our business running.

We’d love to hear a story of resilience from your journey.

See above story.

When COVID hit, not only did I lose everything, I made a choice to restructure my staff in a way that some people didn’t approve of. While I made these decisions, I had also just had a baby and was going through a divorce.

From every angle, I had people trying to tear me down. I was virally bullied online due to mistakes that I had made in my past (that I was very honest about and owned up to and took responsibility for) and the hatred I felt from so many was overwhelming.

I’m so thankful to my loving friends, family and the loyal community at my business that continued to believe in me and build me up. If it wasn’t for these people, the noise of the world would have gotten to me and I don’t know where I would be today.

I will always get knocked down. And I will always stand up.

Contact Info:

• Instagram: https://www.instagram.com/waggingriders?igsh=dXBieTg4Znd5bjV0&utm_source=qr
• Facebook: https://www.facebook.com/profile.php?id=61554584346103&mibextid=LQQJ4d
• Youtube: @amyoostveen and @waggingriders