Ten years ago, Amy Shack Egan accidentally got into the wedding planning business. It all began when she volunteered to assist a friend plan her wedding. Back then, Egan was fresh out of college. At the time, she was working three jobs in New York City just to survive. Little did she know, this initial foray would lead her to establish a successful business and attract high-profile investors, including actress Kerry Washington.
In 2015, Egan launched Modern Rebel, a New York City-based, nontraditional wedding planning business. Over the years, her hobby evolved into a successful business. By 2016, only one year into the business that Egan never expected to start, she handled six weddings. In just a few years she established an enviable reputation for producing what she calls “love parties.”
Perhaps the greatest entrepreneurs you’ll ever meet are the ones who are not completely sure they want to start a new business at all. That’s just how I tried to do it, Egan said.
In just the past year, Modern Rebel has blossomed. What started as a one-woman show has turned into a discerning staff of creatives, all committed to creating truly unforgettable experiences for couples. Her company has gone on to plan more than 500 weddings, receiving acclaim for its fresh perspective in a traditionally hyper-traditional — and sometimes stiff — industry.
Despite her success, Egan remains grounded. Between her career and family demands, she makes her home with husband John and their first child, four-year-old Arlo. As Egan gears up to welcome that child in August, she’s birthing her newest venture, Cheersy. This new digital platform, which went live in February 2025, matches interested couples with specially vetted wedding planners.
“There’s a real need for someone who can step in a few weeks out, get to know the event, and then be their stage manager,” Egan noted regarding the services offered by Cheersy.
Egan’s vision for Cheersy grows out of her years spent in the wedding industry. Couples often contacted Modern Rebel ask for advice on who they could hire that would be a trusted coordinator. Egan recognized the demand and made moves. So he invented a simple yet effective way for couples to make their plan while not skimping on the quality of service.
To support her expansion efforts, Egan opened a small pre-seed fundraising round in the summer of 2023. She chose to delay the release of seed funding until 2026. Made at a time when she was looking to scale Cheersy even deeper and expand on her offerings, this decision was a huge one.
One big breakthrough along her entrepreneurial path came when actress Kerry Washington agreed to come in as lead investor for Cheersy’s pre-seed round. Egan had been connecting with Washington through her own network. One important contact gave her the push, convinced that the actress would appreciate and respect the producer’s vision.
You’ve got to talk to Kerry, she said, she’s going to be gaga about this, Egan talked about the lead off hitter that changed everything.
When I replaced Ryan with Kerry, I knew it was the right fit immediately during our first interview. Her support really validated my small-business venture in a huge way.
To have her come in early and say ‘I believe in this, I back this’ was so validating. Egan stated. Her relationship with Washington exemplifies the potential for collaboration between creative minds in different industries and highlights how influential backing can benefit startups.
Egan’s approach combines her experience in gender studies with her interest in wedding planning. She aims to challenge traditional norms within the industry while supporting couples during one of the most important events of their lives.
I have spent years in the trenches alongside them. I have great admiration for the service and absolutely love what I see happening out there sometimes, she remarked about her commitment to clients.
Now, Egan counts the minutes in eager anticipation of her second child’s arrival. While building her business empire and brand, she shares the struggle of being a mother and an entrepreneur at the same time.
No one can deny the challenge of raising two babies at once. Then you think to yourself, how do they all get this done. She wondered, expressive of the difficulty in juggling home and work responsibilities.