In Conversation with Diana LoMonaco of Classic Six

Describe your Classic Six in a few words?

Six timeless pieces. Endless looks. A highly edited closet full of purpose.

What made you take the leap to start your own business?

A passion for fashion and a desire to have LESS!

What was your background prior to starting your own business?

I was (and still am!) a Graphic Designer. In 2011 I left my corporate job as an Art Director in fashion to start my own business in graphic design, advertising and marketing. In 2015 I dabbled in the blogging world to fill a fashion craving, which later became the catalyst for a moment of overwhelm that ultimately led me to creating Classic Six!

Did you always know you wanted to be an entrepreneur?

Not at all. My dream was to climb the corporate ladder and one day be Creative Director or VP of Advertising at a major brand or corporation. It never really dawned on me that starting my own business was a feasible option and even when it did, being an “entrepreneur” wasn’t something I thought about. I was thinking more about the freedom to be creative on my own terms and they fact that I just needed enough steady clients to pay my rent! It then took on a life of its own where I could safely say I was working towards growing a business. Later when I toyed around with the idea of taking the leap into a product-based business, it actually didn’t feel as outrageous as quitting a safe corporate job, because without even taking too much stock in it at the time, I had already dipped my toes into a world where I could pave my own way.

Take us back to when you first launched your business, what was your marketing strategy to get the word out and did it go as planned?

It definitely did NOT go as planned! I had launched a private online pre-sale (for my mailing list only) back in December 2019 hoping to sell enough to pay for a portion of my production run. Turned out I was in fact able to sell enough to pay for a good portion of my production, and the pre-sale orders were set to be delivered in early March 2020. You know where this is going, right? I was so excited to officially launch the brand in March until I got news that on top of a deadly and globally spreading virus, there was a major supply chain crisis and my factory couldn’t give me a date as to when they would reopen, let alone when my production would arrive. I decided on a wing and a prayer to officially launch the brand in April without a single product in sight. The site went live to the public and people could buy at a pre-sale price with a portion of the proceeds going to Covid-relief efforts.

I was so ready to launch and I just couldn’t stand the idea of waiting another second especially when I saw this as an opportunity to share the brand with people when they were at home endlessly scrolling social media. Finally, at the end of June the product arrived and was ready to ship out. The marketing that I rolled out in those months of “waiting” was pivotal in building the brand awareness and community we have now that the collection is fully shoppable.

We always learn the most from our mistakes, share a time with us that you made a mistake or had a challenging time in business and what you learned from it?

The above was definitely one of the most challenging times to date because of the stress in the unknown. I do however I think I learned a lot when it comes to what it takes to keep a ship afloat in a storm. There are always going to be stressors. There are always going to be moved deadlines. There are always going to be challenges that I have to find a way to overcome, but I think if I go into the next years of this business knowing that, those stressors will hopefully seem more surmountable. Everything happens for a reason and while there may not always be a perfect solution, I know for certain and I have faith that there can and will be some kind of a solution. It’s about growing through it, not just going through it.

What is the accomplishment you are the most proud of to date?

100% Classic Six. I have had so many failed ideas and concepts that never came to fruition, so the fact that I have actually gotten this brand past the launch and into the homes of happy consumers feels like a major accomplishment for me. Now let’s hope we can keep on trucking because everyday is a new battleground!

When hiring for your team, what is your go-to interview question? Please share any hiring tips you can share from your experience?

I think the most important thing for me is to feel the drive and passion and to ask them about what lights them up. I also think it’s generally an intuitive thing that you can either feel or not feel when you meet a person. Will they hustle for you? Will they care about your business as much as you care about it?

What’s next for your business? What can we expect to see over the next few years?

I want Classic Six to be the brand that paves the way for a more conscious consumer. I want to set the foundation for a woman’s wardrobe so they don’t feel the need to buy more and more of the things they don’t need. Quality over quantity all the way!

What is the biggest lesson you have learned in 2020?

Don’t sweat the small stuff. Let go and follow where the wind takes you! Say yes to everything. You never know when that coffee date, or that phone call or that few minutes of your time is going to lead you to the next amazing opportunity.

What do you know now that you wish you knew when you were first starting your business?

Oh jeez, how much time do you have?! I knew NOTHING about the fashion supply chain when I first started and absolutely wish I knew what I know now when I started. It would have saved me a LOT of headache. There is no rulebook, though. I’ve taken course after course to prepare me for the production side of things, and none of it quite matters until you are thrown into it and actually experience it for yourself. But hey, it’s about the journey, not the destination, right?

How have you managed to stay grounded this year?

My family. They are my biggest cheerleaders and also my biggest critics. It’s a good balance 😉

Do you believe in work/life balance? What are some of your best tips?

Ah, this is a tough one because I wholeheartedly WANT to believe in it. I try as best I can, but the guilt is real. When I’m working, I feel guilty that it’s taking over my life and when I take time away, I feel guilty that I’m not working. The reality is you can ALWAYS be doing more for your business. That is never going away. Your to-do list is never going to be wiped clean. I’m sorry. It’s not. Accept that and reshape what the life-side of balance looks like. I actually wrote an article about this exact topic because it is so important to me. What I found is (and don’t get me wrong, I still have to remind myself of this on a daily basis) time away from my work is necessary to refuel. A vacation or a dinner out with friends, or just shutting down and being more present with your family is not just an escape from your business, it is where your brain can rest in order to be the most creative and productive you can be. Knowing this makes these breaks more sustainable. I love the Diana Vreeland quote, “Leisure will give us more time for beauty and the craving to be busy and productive.”

What’s something our audience would be surprised to learn about you?

I am an introvert at heart. My favorite place to be is at home with the people closest to me. I think there may be a bit of a stereotype when it comes to entrepreneurship…that you need to be extroverted, a shark, and constantly “on.” It’s not true. So to all the passionate, creative introverts out there…YOU CAN DO IT!

What are your top 3 tips to stay productive each day?

I have one major one, and it is so simple, yet so effective. Have your standard running to-do list, but before you end each day, make selections from that list and create calendar slots of them for the next day. I am a chronic procrastinator, so while putting times next to each of these items may seem so trivial, it is a productivity game-changer to wake up and have a clear plan of attack for the day. Give yourself wiggle room, too. For example, filling out this interview was on my calendar for today from 11-1pm. I was done at 12:30, which felt great because I had time to breathe before my next task. I started doing this when I told myself I had no time to exercise, but once I started scheduling it into my day, it was interesting to see how much time I could create.

What does being an Entreprenista mean to you?

A badass girlboss with the courage to pave her own way!