Kerry Washington invests in wedding marketplace Cheersy

Kerry Washington is expanding her angel investment portfolio, serving as lead investor in the pre-seed round of the wedding marketplace Cheersy.

Cheersy, which was founded in 2024 by Amy Shack Egan, helps couples find day-of-service wedding coordinators and has raised a total of $550,000 from other investors, including Elizabeth Cutler, co-founder of Soul Cycle, and Jennifer Gilbert, founder of Save the Date. Joanna Rosholm, the former press secretary to First Lady Michelle Obama, and Christina Tosi, the founder of Milk Bar, advised the round.

Washington did not immediately respond to our request for comment.

Shack Egan said she met Washington through the actor’s director of social impact. They both attended a dinner party in Los Angeles where Shack Egan struck up a conversation. By the end of the dinner, the director of social impact offered an introduction to Washington as a possible angel investor. Washington has been making a name for herself as an angel investor alongside other Hollywood titans edging their way into the world of startups.

Cheersy / Modern Rebel Headshots - November 2024 — Lensy MichelleImage Credits:Amy Shack Egan

She’s an investor in the social website Spill, a Black-owned alternative to X. She’s also backed the eating disorder treatment startup Equip and, according to PitchBook, has cut checks for the charity fundraising platform Omaze and the healthcare company Solv. She was also an investor in The Wing, the women’s social club that shut down in 2022.

“The dinner was a few days after I was supposed to fly home, but I knew I needed to be in that room of power players,” Shack Egan told TechCrunch. “I extended my trip and went to the dinner.”

From there, Shack Egan dealt with the rest of the fundraising market, an experience she called “challenging.” “I didn’t know what I didn’t know. I said yes to everything. Jumped on a flight. Got strung along, told no, and put my foot in my mouth more times than I can count,” she said.

This is Shack Egan’s second business. She also founded wedding planning business Modern Rebel, launched in 2015. She founded Cheersy because Modern Rebel was getting so many requests for day-of wedding coordination, meaning having someone make sure that the wedding is running smoothly the day it happens.

“Day-of coordination is the most booked wedding planning service, and so I responded to requests for this service we didn’t offer with handpicked recommendations,” she said, adding that she then realized her offering recommendations could simply be built into a marketplace business. The result of that was Cheersy, which, she says, has a similar model to Airbnb.

Couples look for vetted matches that fit their budget, vision, and vibe, searching by date, price, and specialty. Then the two parties can book a call and, if everything is a fit, the couple can book the talent.

Shack Egan considered her small business background a strength but said it was not the “easiest pill to swallow” for investors who were looking for Big Tech companies on her résumé.

“The fundraising journey can be so lonely and a real knock on your mental health,” she continued.

She joined the Power to Pitch program, which helped connect her with more people in the startup world. The company will use this fresh capital to enhance the features on the booking platform and make some hires, such as a user experience designer. Shack Egan also wants to up the marketing budget a bit and bring in a community manager as the company seeks to expand into six new cities in the upcoming months. It’s currently offered in New York City and Hudson Valley.

“I started in this industry in 2015 as an event freelancer,” Shack Egan said. “I know the pain points of this job personally. I love the idea that we’re making the experience of being someone that works in the wedding industry, in such a tough — and often, thankless — job more supported and more fun.”

This piece was updated to reflect who advised the round.