Madeline Hamilton built a mommy-and-me dress brand that has been worn by Joanna Gaines, Hilary Duff, Jessica Alba and more.

How Madeline Hamilton co-founded Ivy City Co.

Madeline Hamilton built a mommy-and-me dress brand that has been worn by Joanna Gaines, Hilary Duff, Jessica Alba and more.

The year was 2013. I had depression, a fresh art degree and a six-month grace period before my student loans kicked in. The news of my roommate moving before our lease was up rung in my ears. We were both barely making rent each month on our Dallas apartment, and my family was in no position to help me financially. 

How would I come up with enough to now cover double what I normally paid? My options were obvious: 1. Find a new roommate, 2. Hustle to make more money and make it fast, or 3. Find the money to break the lease. I opted for option two by leveraging Groupon listings to get photoshoot gigs. 

I took on senior portraits, family pictures, and even recorded a funeral service for someone. I blogged with my best friend, and I enlisted my name to an on-call list for “working events,” which turned out to be passing out samples in grocery store parking lots.

I was bringing in some money, but as my depression worsened, my motivation to keep up the grind diminished. I knew the time had come to break my lease, which cost double one month’s rent. I drained all my funds except the amount I needed to fill my tank and drive back to my small Texas hometown. I had officially broken the pact I had made with myself long before that I would never move back home. 

My mom and brothers welcomed me with open arms but could see my usual peppy energy was gone. Rock bottom looked like pulling out my guitar to write a song—the only coping mechanism that had been working—to find a large crack in the body of my beautiful Taylor. I remember the sound of sobs hitting my ears before I realized I was crying. At that moment, it wasn’t just a guitar. It was my last strand of hope: broken. 

Something needed to change, and I knew it. I had so much I wanted to accomplish. I had a notebook chock-full of ideas. I was a creator at heart, and just needed to get back on my feet. 

T-minus four months until I had to start paying toward my student debt; I was terrified. (Remind me why I insisted on a pricey private art school with zero grants and close to a 10 percent  interest rate?) When an 18-year-old has a dream, I suppose. 

My family cheered me on as I freelanced photography, worked on my mental health and searched for my next move. Cue the turning point: A random phone call from an old friend turned into an invitation to live in their extra room for a summer in Salt Lake City. A rent-free opportunity to “find myself” in a bigger city? Why not? I had nothing to lose. I loaded everything I could into my little car and drove to Utah the next week. 

In retrospect, that seemingly random invitation was one of the most important moments of my life. Consider this my plug for picking up the phone and checking on people when they come to mind. 

I was wowed by the mountains and the buzzing energy of my new home. The healing had begun, but the ever-encroaching reality of my student debt weighed heavily on me. Amongst finding myself, I worked four jobs that summer. It was a hodge-podge of managing a dress boutique, nannying, photography and—brace yourself—data entry for mines. My now-husband still laughs at the thought of artsy me working in the mining industry. 

That wild but blissful summer came and went. I fell in love with the city and a boy, and I made the decision to stay in Utah. I found a room to rent at a neighbor’s home and applied for full-time jobs on Indeed to consolidate my life a bit. And so, my career in marketing began.

Beginning a marketing career

I got an entry role on the digital team at Skullcandy in Park City. I wrote songs on my drives to the office and typed tweets for NBA players behind my desk. I learned fast in my role at the then-public company and was inspired by the way CEO Hoby Darling led the culture of the company. 

During my off hours, I kept up my blog with my best friend, and she encouraged me to release some of my music. She and I even had the opportunity to give a TEDx talk in Mexico and work on campaigns for brands we loved. I truly fell in love with marketing and connecting with people. I didn’t know it at the time, but all of these experiences were shaping me for my own future company. 

After a year or so of my job at Skullcandy, I transitioned to a local startup with a focus on empowering women. I found my niche! In a director role at Albion Fit, I built my first team. I was thriving. 

There was something special about seeing my work directly impact the swift growth of an e-commerce business. I lived and breathed that job as if it were my own company for a handful of years, but at the end of the day, it was not my company. I love helping others bring their dreams to life, but at my core, I am a dreamer, too. What would happen if I went all in on myself?

Freshly married, I told my husband I was going to quit my job to find my dream. He supported me, but we settled on a timeline for how long we could financially survive without my salary. Those student loans were still keeping it real, after all. I had one month to pull something off. 

I spent the first week panicking that I had just made a massive mistake by quitting a job I loved, but then the fire started burning. I put my name out there. I met with local entrepreneurs. Nothing was adding up until a loose connection invited me to lunch to “pick my brain” about marketing, so I met up with Whitney Smith and Natasha Thomas at The Cheesecake Factory. 

They told me about their startup. Between their amazing skills in design and accounting, they had created a dress company emphasizing “mommy and me” matching. They were starting to gain a following and had fine-tuned a beautiful product but didn’t have a marketing background. 

They wanted to see if I’d consider a consulting role. I walked away inspired. I saw their vision. There was nothing like it in the space at the time. I had a million ideas on how to help blow up the company and could see myself working alongside such powerhouse women. Twenty-four hours later, I was one-third owner of Ivy City Co., and the greatest adventure was about to begin. 

Venturing into the unknown

It was early fall of 2018 when I took the leap into co-owning a dress company. I had full confidence in the future of the brand, but the present-day reality involved little-to-no paycheck while we built it up. 

I told my new partners I needed to take on side jobs until the dress business could be my sole income. They were supportive, considering my history of balancing projects. My husband worked a full-time day job while attending MBA classes at night, so I had plenty of time on my hands. I basically did nothing but eat, sleep and work—and I was thriving! My two side jobs were fulfilling, and Ivy City felt like a door to my heart opening. My dream was playing out right before my eyes.

Ivy City Co. was small but profitable. The business was self-funded and self-operated. We had one employee, a family member, who graciously stored the inventory in her basement and shipped out orders. The bones of the business were established. Now it was time to let the world know about Ivy City Co. and our mission to empower women and girls everywhere with confidence and community.

I hit the ground running, ready to put my marketing knowledge to the test. The first step was to give our dresses to as many creators and influencers as we could afford. We leaned on social media and reached out to people we thought would love the product, really focusing on our “mommy and me” factor. 

I stayed up late designing email newsletters, sliding into collaborator DMs, sketching dress ideas and editing photos from shoots. My partners and I met up weekly to try on samples, communicate with manufacturers and take pictures.

"We started this business to chase our own dreams, but what keeps us going is our teammates and customers—hearing their stories of finding confidence and joy through our dresses is everything to us. We hope to improve each and every day for them. In fact, we couldn’t do it without them."

Building the team

Between the three of us, we managed the website, finances, customer service, purchase orders—everything; because that’s what you do in a startup. Within a few months, everything was working. Sales and social followings were picking up, and we knew the time had come. We needed to build a team. 

We hired an agency to manage the website, emails and ads. We brought on two more women to tackle customer service and shipping. A couple of months later, we signed a lease on a small warehouse with thin walls. I have flashbacks of our neighbors banging on those walls because we were too loud. 

We hosted our first in-person event and were in complete shock to find hundreds of people wrapped around our building at 7 a.m. on a Saturday, waiting to get in. Our husbands passed out hand warmers to people in line while we met our community in person and bagged their orders. We built friendships with our customers. We listened to their feedback and designed dresses based on their requests, something we still practice today. 

Looking back at those earlier years, we could never have predicted the ride ahead. We are now among the Inc. top 500 fastest-growing companies in America, employ 60 people and have gone from shipping 10 dresses a day to thousands. We strive for size inclusion and offer over 24 dress sizes in a fashion world that typically only offers six. We are proud of what Ivy City is becoming, but it hasn’t always been smooth sailing. 

Each of us has carried parts of the business on our backs whilst carrying babies through pregnancies and raising families. We aren’t strangers to postpartum depression or heartbreak. It’s a balancing act we haven’t quite mastered, but we wouldn’t trade it for anything. It’s been rewarding and challenging. 

We’ve discovered our strengths and uncovered weaknesses. We’ve gone to bed smiling after good days and cried on the phone at night, navigating things like company culture and inflation. We started this business to chase our own dreams, but what keeps us going is our teammates and customers—hearing their stories of finding confidence and joy through our dresses is everything to us. We hope to improve each and every day for them. In fact, we couldn’t do it without them.

To infinity and beyond

Becoming an entrepreneur is the most terrifying and rewarding thing I’ve ever done. I couldn’t have made it to this point without every loss and win from my past. Of all the many lessons I have learned in business, these have stuck with me the most: 

  1. The fastest way to level up is to make your boss or customers’ life easier.
  2. Anticipating the needs of others and showing up for them is a catapult for growth. 
  3. Every bit of experience in your past life is relevant, no matter how big or small, may it be personal or professional—your history is a tool for your future and empathy is a superpower.
  4. Those who stay consistent and reliable through the hard times will come to mind first when growth opportunities arrive. 
  5. Vulnerability is not a weakness. 
  6. You are going to make mistakes, but that doesn’t mean you are a failure.
  7. Acknowledge when you mess up; own up to it and choose to grow from it (I’m still learning this one). 
  8. Rock bottom is the ultimate opportunity. Keep going. You got this!

Utah has an incredible ecosystem for starting and growing businesses. People here are eager to help bring dreams to life. Reach out, go to lunches, build relationships and work together. Magic will happen! Cheers to learning, growing and having fun along the way!

Madeline is a Texas-raised artist and entrepreneur. After graduating college, she moved to Utah, fell in love with the mountains and called it home. After five years in the marketing world, she followed the pull to put her heart into her own business and joined the Ivy City Co. family. She loves helping others see their purpose, creating art, laughing and making memories with her husband and daughter.