Meet Alessandra Guzman | Mother & Matchmaker

We had the good fortune of connecting with Alessandra Guzman and we’ve shared our conversation below.

Hi Alessandra, we’d love to hear more about how you thought about starting your own business?
I had previously dedicated more than 15 years of my life working in the arts. So much of that life was meeting new people, planning events, and building connections. I enjoyed that work immensely, but more than anything, I loved getting to know people on a personal level. Whether it was gallery clients, artists, donors, or co-workers, I just wanted to chat! Dare I say I was a bit nosy and loved to ask personal questions. One of my favorite topics was other people’s love lives. I would regularly try to set people up and often say, “I’d love to be a matchmaker.” I even knew what my business name would be: Meet Cute Matchmaking. I’ve had the url reserved for years!

Flash forward to 2020 – I had just had my 2nd baby, we relocated to Boulder for my husband’s job, and then COVID! I settled into being a stay-at-home-mom for the next 4 years, adapting to remote learning and enjoying spending every minute with my babies. As the world returned to normal and my youngest approached kindergarten, I knew the time had come for me to go back to work. But the kids are still young and I need flexibility. I picked up some contract work here and there but something kept pulling me back to the idea of matchmaking. I continued to joke about it, and commented on socials that I was considering starting a matchmaking business. My inbox was suddenly full of messages from singles expressing interest in my services. It was then that I realized that my silly dream could be a reality. I had never started a business before, but I thought to myself, other people do it, why can’t I?

So there I was, psyching myself up to start my own business. I began doing all the research for forming a business in Colorado and how to become certified as a matchmaker. I put together a website and began to put myself out there – Meet Cute Matchmaking, Boulder’s local personalized matchmaking service. Next thing I knew, I was in business, officially!

Can you give our readers an introduction to your business? Maybe you can share a bit about what you do and what sets you apart from others?
The fact that I am where I am today is greatly due to luck early on, persevering when I doubted myself, a little bravery, and developing self-confidence (still working on that one). When I set off to college, I had no idea what I wanted to do! I loved art so I became a studio art major. After graduation I landed a job at a large art gallery in Austin. I was quiet and insecure, but a good worker, and likable. The gallery owner believed in me and gave me several promotions and added responsibilities from year to year. Over the 5 years I worked there my confidence grew, I learned about running a small business, and I began to advocate for myself. By my mid-20s, I was ready to do more. Off to grad school I went.

I still don’t know how I pulled it off but I managed to earn two master degrees: an MBA in marketing and and MA in arts administration. After graduation, I knew I wanted to either work at an art museum or open my own gallery. Yet somehow, I found myself working at an experience design firm in Keystone. It was an incredible but short lived experience thanks to the recession of 2008. I learned a lot about creating authentic experiences that I have been able to apply in every area of my life since then.

Alas, I spent my 30th birthday living in my childhood home, applying to job after job with no real prospects. Then a temporary marketing/PR job came up at a museum in Fort Worth, Texas. I ended up working at that museum for ten years! From those first days as a marketing/PR temp to my last day as the manager of exhibitions, I grew so much personally and professionally. I walked out of that job knowing I no longer wanted to work for someone else or in the non-profit sector.

Flash forward to 2024 and here I am with my own matchmaking business in Boulder, Colorado. I can tell you it has been full of surprises! Yes, I was scared and came up with plenty of reasons to quit, but the drive to be successful in finding love for others keeps me going. As I was starting on this venture, I would look at all of the other women that had started businesses before me. I love reading success stories! I also love to hear that it’s messy for everyone at first, and sometimes things don’t work out perfectly. But you can always learn from your failures. I am certainly already learning from mine.

This business is so much more than a way to make money. I work with people on an intimate level, in a potentially life changing way. Please don’t hire me as your matchmaker if you just want someone to treat like a personal assistant. This is a partnership on a very personal level. If I’m going to introduce you to the love of your life you better believe we’re going to become close friends throughout the process. That’s also why I’ve chosen to focus on the Boulder County area. I want to meet up for coffee. I want to run into you at the grocery store. And you better believe I want to be invited to your wedding!

Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
My dad always says, “you live where people vacation.” I know! Isn’t it amazing? We always try to show our visitors a good time, but we often don’t have to go much farther than our trails and local spots in North and Central Boulder. Lucky’s for breakfast, a walk around Wonderland Lake, and lunch at Rosetta Hall with a stroll down Pearl St. I love to catch up over a mocha latte at Ozo or a glass of pinot at Silver Wines Winery. With families, we head to the Museum of Boulder and let the kids’ imaginations run wild at the playzeum. If the timing is right, we’ll attend an opening at Seidel City gallery. And of course, we always go for ice cream at Sweet Cow.

The main attraction to Boulder of course is the great outdoors! When we first moved here, we were all about the Anne U White trail and day trips to Estes Park. We still love those! We’ve now added Ceran St Vrain and NCAR to our list of favorite trails. And we wouldn’t be good tour guides without a trip to Chautauqua and Boulder Falls – they are famous destinations for a reason!

Who else deserves some credit and recognition?
Once I knew I was really going to start this business, I began joining networking communities, local and international. I found Jen Morris’ group, now known as Renegade Motherhood Business Society, and attended one of their monthly networking events. If you want to find support as a mother in business, find a group of other mothers in business! They have been by far my biggest cheerleaders. It has been so great to share our experiences and tips with each other. Some of the first women in my singles database came from that group, and I can always count on them to tag my business whenever someone is posting about how frustrating dating is in Colorado.

I’m also lucky to have a supportive sister nearby that is an immigration attorney. She and her husband, an author and attorney, have provided me with a ton of professional guidance and free legal advice as I got started.

Of course I couldn’t have even considered starting this up without the support of my husband, Ryan. He’s the hardest working man I know, but is always willing to stop and take a look at whatever crazy thing I’m working on at the moment. It helps that he has a business degree from Harvard and is a very tech savvy guy. When I’m running around like a chicken with its head cut off before a singles event and the printer isn’t working, he swoops in and takes care of it for me.

Website: https://www.meetcutematchmaking.com

Instagram: @meetcute_matchmaking

Facebook: https://www.facebook.com/MeetCuteMatchmaking/