Ten years ago, Amy Shack Egan agreed to help a friend plan her wedding. She couldn’t have imagined that it would inspire her to launch two businesses — or that Kerry Washington would become her lead investor.
At the time of that first wedding, Egan was freshly out of college and working three jobs to stay afloat in New York City.
“I was like a lot of early 20-somethings: frustrated about feeling really ambitious, but not sure what path I was supposed to go down,” Egan recalls.
While helping her friend navigate wedding logistics, she found that she had a knack for event planning — and an unexpected interest in the wedding industry.
Weddings quickly became Egan’s side hustle: that year, she planned three more weddings as a freelancer. The next year, she planned six weddings. By the following year, in which she booked 25 weddings, Egan decided to focus on wedding planning full time.
That’s the origin story of Egan’s first business: Modern Rebel, an ‘unconventional’ wedding planning company she founded in New York City in 2015.
As a former gender studies major, Egan, now 33, says that she had never imagined herself entering the often hyper-traditional wedding industry, but the idea of “rewriting the rules” intrigued her.
“Sometimes the best people to start a new business and shake up an outdated space are the people that go into it almost reluctantly — which is definitely how I did,” Egan says.
In the ensuing decade, Modern Rebel has planned over 500 weddings, which Egan calls “love parties,” and expanded from a one-woman show to a team of “really talented people.”
Still, she knew that there was even more room to grow within the industry – even if that meant taking a step back from wedding planning.
Not a “typical tech CEO”
Over 80% of couples plan their weddings by themselves, according to a 2025 survey by The Knot.
However, it can be difficult for couples to manage logistics while enjoying their big day, so many look to hire a wedding coordinator, Egan says: “Somebody who can step in a few weeks out, get to know the event, and then be their stage manager.”
In Egan’s experience, a good wedding coordinator can be hard to find. Online wedding marketplaces often have subscription fees and can be difficult to navigate, she says, so many couples resort to finding wedding coordinators through word of mouth.
“For a lot of reasons, there were couples reaching out to Modern Rebel saying, ‘hey, who do you trust? Who do you recommend?'” Egan says. “I realized that this could be its own business, and it actually could be bigger than Modern Rebel.”
In February 2025, Egan officially launched Cheersy, a digital platform that connects couples with pre-vetted wedding coordinators.
It’s the kind of company Egan wishes had existed back when she was a freelancer, she says.
“I have been in their shoes,” she says. “I have been in the trenches with them. I respect and value the service, and I see how important it is.”
Her experience with Modern Rebel has helped her understand both sides of the wedding marketplace, she says: “I’m not your typical tech CEO that’s just focused on the bottom line. I have a lot of respect for both sides of this equation.”
“When I met Kerry, it was an immediate ‘yes'”
Becoming a tech entrepreneur involved a lot of learning for Egan — mostly the hard way, she says. She had no prior fundraising experience when she launched Cheersy’s pre-seed round, which concluded in January 2025.
“I just cast that net out to some really incredible people in my network,” Egan says. “I said, I don’t know what I don’t know, and if there’s someone in your network that I should know, please introduce me.”
Through “somebody who knew somebody,” Egan found herself discussing Cheersy with actress Kerry Washington’s director of social impact at a dinner party.
“She said, you’ve got to meet Kerry. She’s going to love this,” Egan recalls.
Pitching Cheersy to Washington was “surreal,” she says.
“When I met Kerry, it was an immediate ‘yes’ the first time we had a meeting,” she says. “For her to come in early and say ‘I believe in this, I back this’ was so validating.”
Washington resonated with Cheersy’s mission that “all couples are seen and celebrated,” Egan says.
Washington, who became the lead investor for Cheersy’s pre-seed round, is just one of the company’s high-profile investors. Others include Elizabeth Cutler, co-founder of SoulCycle; Jennifer Gilbert, founder of event planning company Save the Date; and Christina Tosi, founder and owner of Milk Bar.
By the end of the pre-seed round, Cheersy had raised $550,000 in financing, all from angel investors.
Navigating a unique challenge
Egan had initially planned to start Cheersy’s seed round in fall 2025, but she and her husband Dan received unexpected news in January: after a year of struggling with secondary infertility, Egan was pregnant with twins.
“I think anyone, even if they’re not an entrepreneur, is like, how the hell do you raise two babies at the same time?” she says. She and Dan also share four-year-old son Arlo.
Since her due date is in August, Egan decided to launch another small pre-seed round of fundraising in the summer, and pushed seed funding to 2026.
Planning around a pregnancy is “not something that every founder has to deal with,” she says, “but it’s a unique challenge, and I’m up for it.”
In the meantime, she’s working on growing Cheersy’s customer base, building connections with vendors, and preparing for another round of fundraising.
Creating a startup “isn’t a straight line,” Egan says, but she’s using every bit of her experience in the wedding industry to build Cheersy.
“I always wondered why the universe made me a wedding planner,” she says. “I look now at where I am with Cheersy, and where we’re going with it, and I feel like the universe was giving me a front row seat to couples in this beautiful way.”
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