We’re excited to introduce you to the always interesting and insightful Amy Gray. We hope you’ll enjoy our conversation with Amy below.

Amy, looking forward to hearing all of your stories today. Owning a business isn’t always glamorous and so most business owners we’ve connected with have shared that on tough days they sometimes wonder what it would have been like to have just had a regular job instead of all the responsibility of running a business. Have you ever felt that way?

Absolutely. There are moments when I think a regular job might be easier, but not for very long.

The last time that thought crossed my mind, I was in the middle of one of those classic owner days where everything was happening at once. A family needed childcare quickly. A caregiver question came in. There was something to troubleshoot in the booking system. My inbox was busy, my phone was busy, and I was bouncing between Sitterwise, photography work, and the other moving pieces that come with running more than one business. I was probably standing in the kitchen with a cup of tea gone lukewarm, answering one text while mentally rewriting my to-do list for the fifth time.

That is usually the moment when the idea of a regular job flashes through my brain. Not because I actually want one, but because I briefly imagine how strange it must be to have one role, one set of responsibilities, and an actual stopping point at the end of the day.

But I discard that idea pretty quickly.

The truth is, I love being a business owner. I even love the slightly wild part of it. I love the flexibility of working 18 hours a day but getting to choose which 18. I love building something meaningful. I love solving problems. I love that no two days are the same. And apparently, I love this enough to do it in multiple businesses, which probably does make me sound a little unhinged.

Sitterwise in particular carries a lot of responsibility because we are serving families and caring for children, and that matters. But there is also so much joy in creating something that helps people in a real way. The hard days are real, but so is the satisfaction of knowing I am building something of my own.

Amy, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

I’m Amy Gray, owner of Sitterwise, a San Diego-based childcare agency that connects families, hotels, events, and organizations with trusted, experienced caregivers. At its heart, Sitterwise is about helping parents breathe easier. We step in when families need safe, reliable care, whether they are traveling, attending a wedding or conference, going out for the evening, or simply needing support at home.

I came into this business through family. My mother-in-law, Marion, built Sitterwise on trust, personal connection, and caring well for people. When I stepped in, I wanted to preserve that foundation while also strengthening the systems, branding, and operations so we could serve more families well.

What we provide is childcare, but the real value is trust. Parents are not looking for just anyone. They want someone capable, warm, professional, and dependable. We help solve that problem with thoughtful matching, strong standards, and a personal approach that is much more hands-on than a faceless app.

We serve families in a wide range of settings, from private homes and hotels to weddings, churches, conferences, and other events. I’m especially proud that as Sitterwise has grown, we have worked hard to keep the heart of the business intact. I want families to know they are cared for, and I want caregivers to know they are valued too.

What sets us apart is that we combine high standards with a genuinely personal touch. We care about doing this well. We want the experience of working with Sitterwise to be polished, warm, dependable, and easy. At the end of the day, I’m most proud that we help make life work a little better for families in very real, practical ways.

Can you talk to us about your experience with buying businesses?

Yes. We made the decision to buy Sitterwise in 2003, before Marion’s son Rod and I got married. I officially took over in 2005, after our daughter Lissa was born and I stepped away from teaching.

At the time, we knew we wanted to start a family, and I also knew I did not want to keep teaching while raising my children. Sitterwise seemed like a wonderful opportunity, but it also felt intimidating. Marion had built something special, and she worked incredibly hard. I did not come from a family of entrepreneurs, so I honestly wondered whether I had the wisdom and tenacity to do it.

What changed everything was realizing I did not have to lead the business exactly the way it had always been run. As I stepped in, I began bringing some of the systems, structure, and technology-minded thinking I had developed as a teacher. That helped me make the business my own, and once I did, I found that I genuinely loved it.

What started as a leap of faith became work that was creative, meaningful, and surprisingly fun . . . so much fun that I have started three more businesses since then!

What else should we know about how you took your side hustle and scaled it up into what it is today?

Yes. In a funny twist, photography was the side hustle, and it grew out of Sitterwise.

I was already running Sitterwise, and as we worked to market the business, I started learning photography so I could take better pictures of the events, families, and moments we wanted to share. At first, it was practical. I was just trying to make our marketing stronger. But somewhere along the way, I realized I loved it.

What started as a useful skill turned into a creative outlet, then into paid work, and eventually into its own business. The more I photographed, the more I learned, and the more people started asking me to shoot for them. Over time, photography grew from “something extra” into a real business with its own momentum.

One of the biggest milestones was realizing people were not just hiring me because I happened to have a camera. They were hiring me because they connected with my work and wanted my eye, my style, and my way of capturing people. That was a big shift. Another milestone was building enough consistency and demand that photography became more than occasional jobs. It became its own lane.

What I love about that story is that it was not some grand master plan. It grew naturally out of something I was already doing. I learned photography to help one business, and it ended up becoming the next one.

Contact Info:

• Website: https://sitterwise.com
• Instagram: https://instagram.com/sitterwise
• Facebook: instagram.com/sitterwise
• Linkedin: https://linkedin.com/in/amycothrangray
• Yelp: https://www.yelp.com/biz/sitterwise-san-diego-4