Five Years of Crown Affair
Reflections on trust, time, and transformation
I’m writing this letter to you from an airplane. A place where I’ve spent a lot of time the last five years since I launched my brand, Crown Affair. In the early days of the business, there wasn’t much travel, given a global pandemic six weeks after we went live. So much has happened since.
I’ve been journaling through most of it, but somehow I’m not quite sure of how I started there and got to here. I started Crown Affair out of my rental apartment on 37th and 8th Avenue (what I affectionally call the armpit of Manhattan).
I had a vision for a different kind of haircare brand, some product samples, and my favorite images pinned on a black foam board from Blick. I’d spent the last decade working non-stop building other people’s brands and living the startup-millennial “dream.” By the time I launched my brand agency, Levitate, I had two core pillars that defined how I wanted to work, an antidote to years spent enmeshed in hustle culture:
Make my own hours / create my own schedule: By then I knew that excellent work did not equate to how many hours your butt was in a chair at an office
Choose who I want to work with: When you’re employee 8 and a year later you wake up there are 100 people around you and everyone’s just moving fast and breaking things, chaos will ensue.
After two years of Levitate and laying down the foundations of Crown Affair, I launched it on January 28th, 2020, with one full-time hire (who is my left brain, right-hand, and a big announcement about her soon), and my favorite former colleagues as contractors to get this thing up and running.
Looking back, I don’t know what to chalk it up to other than pure ambition, grit, and utter delusion. I didn’t know that when we hit publish on our Shopify site how much the world would change over the next five years.
I started Crown Affair because I wanted something better— both in products and a life for myself. Since I was young I wanted to surround myself with beautiful objects and things that bring me joy. I would rip out the pages of Vogue and W and pin them on my wall and study every credit as if I were being tested. My Teen Vogues were my religious texts. It’s why art is my favorite thing. I believe that the things we surround ourselves with have meaning and become the visual literacy of your life.
I’ve spent my life punching up, striving to build the beautiful world in my head in real life, and in such a big way, reaching for the stars — making the products of my dreams, launching with Violet Grey, the Gwyneth and Goop of it all, Sephora, raising capital, hiring my incredible team. This journey has been the privilege of a lifetime and it’s opened my whole world.
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After half a decade as a founder, here’s what I know to be true:
Rewiring my brain to take my time to find balance in it all: Doing The Artist’s Way in September 2020 during lockdown changed everything for me, bringing Morning Pages and artist dates into my life to stay aligned with my creative essence. It’s taught me that leading with feminine energy and finding balance—between rest and showing up fully—is the key to building a sustainable and inspiring business.
Hire remarkable talent who are good people: Surrounding yourself with incredible, kind people makes all the difference. Elaine and the rest of my team are not just colleagues—I authentically trust them like they’re family, and I feel so lucky to get to build something meaningful with them.
Never give up, never surrender: Keep going, no matter how hard it gets, and avoid getting caught up in nostalgia—it’s about moving forward. Progress comes from showing up every day, even when it’s tough.
The day you plant the seed is not the day you eat the fruit: Patience is everything. Keep planting seeds daily and trust that they will bear fruit in time.
Keep your blinders up: Imitation will happen if you’re doing great work, but don’t let it distract you. Instead of reacting, focus on innovating and staying ahead with authenticity—there’s more power in creating from a place of inspiration than comparison.
I think the most surreal part of this journey is how Crown Affair and I have grown up together. There have been so many phases, so many iterations of the business. The brand has evolved far beyond me (one of the perks of not being an influencer or celebrity is that it exists as its own entity), but it also continues to change because I do. When you build a brand with soul, that soul moves through the world with the leader, adapting and growing in tandem.
As we approach Crown Affair’s five-year anniversary, I’ve been reflecting on a trip to Japan I took in April 2019—a trip I’d dreamed about for most of my life. I’ve always been drawn to Japanese culture, and seeing so many of the places and references that had lived in my mind was transformative, much like discovering The Artist’s Way. That trip changed me forever. Now, as I plan my next visit, I know I’m going back as a different person—someone who understands that she is enough and that the days and moments add up to something far greater than the outcome. They are the process of becoming. I wake up every day deeply grateful for this life and the chance to create something meaningful. I can’t wait to see what the next five years bring, and I hope we can continue to inspire each other to live beautiful, full, and intentional lives.
Here’s to the next half decade ahead.
Take care, and take your time, always.
Dianna
And now… Three Things I Love and A Haircare Tip:
MagSafe kickstand This is my second phone accessory rec, which probably says something about my screen time. I upgraded my freezing iPhone 13 last week and got this MagSafe kickstand during the upgrade—it’s a game changer. Easier to hold, easier to glance at, and I reach for it less since it tilts for quick visibility. Bonus: I now have two phones—one for social, one for everything else—and I think this setup might just transform how I manage my time..
Dehanche Jeanne Silver Belt A great belt can make or break an outfit. I’ve been loving add this one to otherwise simple outfits.
LeSet Barb Pant This is my go-to pant. I’m wearing it as I write this. Think of it as an elevated version of what you’d wear at home.
A Haircare Tip: Wash Less, Wash Better
Overwashing your hair can strip it of natural oils, leaving your scalp dry and your strands craving hydration. Instead of daily washing, aim for 2-3 times a week (or even less, depending on your hair type). This allows your scalp’s natural oils to nourish your hair, promoting healthier, shinier strands.
In between washes, embrace dry shampoo to refresh roots and add volume. And when it is wash day, focus on a thorough cleanse with a gentle, sulfate-free shampoo and follow up with a nourishing conditioner. Less washing, more balance—that’s the secret to happier, healthier hair.
Doing my Artist’s Way journey right now with a group which has been SO helpful. You are so inspiring, Dianna 🌸
Congratulations Dianna! You’ve always been going places :)