Interview with Rhonda Steger, founder of Cobblestone Living

Rhonda Steger does not regret leaving a lucrative career in the insurance industry; becoming an entrepreneur has proven just as rewarding. Her leap off the beaten path started small when she opened her own compliance firm, but passion soon drew her even further afield, first to retail and then wholesale. Today, she leads Cobblestone Living, a women’s fashion and lifestyle brand that has turned into a thriving family business.

For over 15 years, Rhonda and her husband have built their family brand together. While it began as a small retail shop, from bricks and mortar towards a wholesale business model, Cobblestone has seen sales grow exponentially ever since. As a result, Rhonda is not only building on success but also writing her daughter – now 18 and about to enter university –into corporate succession plans.

We recently had a chance to sit down with Rhonda Steger to discuss her journey towards entrepreneurial success, her challenges achieving work-life balance and the prospect of her daughter taking over the business one day.

Cobblestone Living: An Entrepreneurial Family Business Adventure
Rhonda with her husband, Marty Steger. Image courtesy of Cobblestone Living.

What inspired you to leave a stable career in the insurance industry?

I have always had a little bit of entrepreneurial drive in me. My father is an entrepreneur. I started a compliance firm with another partner when I was 35 and seven months pregnant, and I’ve worked for myself ever since. Even though the insurance industry was very lucrative for me, I was not passionate about it, so I decided to move into other things.

What other steps were there along the path to Cobblestone Living from the insurance industry?

I’ve had a couple of businesses in between. The insurance compliance firm still exists, but I left that in 2017. I also had a home staging business – the first one I started. It was very successful, but at some point, we detected a change in the real estate market. We saw the writing on the wall and, rather than sticking with it, we sold off all our assets and moved on to something different. We were fortunate because we got out right before the market collapsed.

As far as transitioning from insurance to other industries, it was relatively easy because timing and circumstances usually dictated those changes.

Cobblestone Living: An Entrepreneurial Family Business Adventure
Image courtesy of Cobblestone Living.

How has the Cobblestone brand transitioned from retail to wholesale?

We opened up our retail shop in about 2009 – it was called Cobblestone Market – and we ran it successfully for seven years. It was around 2016 when we developed an interest in the wholesale aspect of the retail business and decided to start Cobblestone Living. The company grew very quickly – more quickly than we thought it would – and we ended up selling off the retail shop and focusing our energies toward the wholesale business. That’s where we are now.

Both your daughter and husband already work with you at Cobblestone Living. How do you find working with family compared to running a company on your own?

My husband and I have been working together for the last 15 to 20 years. When we had our daughter, Zemy, my husband was working for someone else and travelling most of the time. When our daughter was about two or three, we realised that it wasn’t good for her dad to be absent for such prolonged periods of time. That’s when he joined me in the home staging business, and we finally started our entrepreneurial journey together as a family.

I love running a family business, but it does come with its unique pressures because the entire livelihood of your family depends on the success of that one company. However, I wouldn’t trade it for anything, especially now that my daughter has expressed a desire to make this her life at some point. Her interest in the company will drive me even more for the next few years to make sure that I have a sound, reliable business, but also one that we can expand once we bring her in.

Cobblestone Living: An Entrepreneurial Family Business Adventure
Image courtesy of Cobblestone Living.

What are each of your roles within the company?

I don’t want to say that I’m the leader, but I do have a stronger entrepreneurial drive than my husband. However, I’m very grateful that Cobblestone Living capitalises on both of our strengths. My husband came from a logistics background in distribution. As we currently distribute to over 700 shops across the country, there’s a lot of technical work required in that area, and he excels at it. He enjoys that side of the business and lets me take care of the rest without his involvement, so it’s not that formal of a process.

The most important thing in terms of our roles has probably been establishing boundaries between our work life and home life. My husband is much better than me at that, and I am lucky to have a daughter who understands that my business is my passion.

How do you balance work and life in your daily routine?

My daughter helps me maintain a work-life balance by reminding me that sometimes, I should just ‘turn it off for a minute.’ I also enjoy baking – that’s where I find a little bit of balance when I need it. However, for the most part, I don’t think I have fully found that balance yet. I love what I do. I can’t wait to wake up every morning and get started. I enjoy it so much that it’s hard for me to disconnect – it’s almost like a hobby for me as well as being my professional life. I often have to remind myself, ‘Am I being present right now with everyone in the family?’ It is a struggle of mine.

Cobblestone Living: An Entrepreneurial Family Business Adventure
Image courtesy of Cobblestone Living.

How have you dealt with criticism over the course of your career?

One of the things that I find most helpful in this respect is to listen to my customers and sales reps and their feedback. I always welcome constructive criticism, whether that be suggestions or complaints about specific things a customer does or does not appreciate.

Understanding my niche in the market has also proven fundamental over the course of my career. There’s nothing new about women’s clothing, and you can’t please everyone. So, while you have to remain open to new ideas and changes, you should also try to stay true to your vision and brand.

Another lesson I’ve learned is: don’t just try to do things you don’t know how to do. If it’s not your strong point, and it’s not central to your business, get somebody else to do it for you and focus on what you know best.

How are you handling the surge in demand for your products?

We’re going into our fourth year with Cobblestone Living, and every year we’ve been doubling sales. It’s been a steep learning curve for us. We’ve been getting better at managing each year, but now our biggest struggle is something we didn’t anticipate – keeping up with demand. We didn’t expect to grow this quickly.

One of the risks you face when running your own company is that you often take things too personally. When your customers reorder a product, and you can’t get it to them as quickly as they’re asking, you do silly things like air-express it to them, which really harms your bottom line. So, our focus right now is on streamlining our operations. My wish is to eventually have other products besides clothing, like home décor for example, just to diversify our product line and appeal to other types of retail shops.

Cobblestone Living: An Entrepreneurial Family Business Adventure
Image courtesy of Cobblestone Living.

Are you anxious about your daughter entering the business full-time after university?

Yes and no. I do want her to be part of this business, but I have to allow her to fail as well. I don’t try to glamorise it or make anything look easier than it is. We’ve had open conversations with her and told her up front that we want her to be a part of this business, but she needs to be able to contribute to it.

We have mixed feelings about letting her work somewhere else for a couple of years before she joins the family business. She’s certainly open to that as well, but it’s still early to decide. We’re going to be supportive of her and make her aware that it’s not all roses. I travel to Italy, but I also unpack boxes. There are a lot of tasks and responsibilities involved in running your own business. She talks to me about it a lot, but she needs to finish college, come back and get her feet wet before we can have a conversation. If she decides it’s not something she wants to do, we will accept her decision.

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