Pride Spotlight: Influencer and Entrepreneur Alysse Dalessandro of Ready to Stare

Posted by: Dena on Tuesday, June 6, 2023

By Rebecca Ferlotti, Special to Greater Cleveland Partnership

From Cleveland to Chicago and back to The Land again, Alysse Dalessandro has been forming businesses around the Midwest for around 15 years. Her impact is global, though—literally. She hosts plus-size and LGBTQ+ trips to Italy and Cuba. But her primary business, Ready to Stare, encompasses social media platforms and a plus-size fashion, LGBTQ+ travel, and lifestyle blog.

“When I started, ‘influencer’ wasn’t even a career you could have. I’ve learned a lot about how this business ebbs and flows, and you just need to make sure you ebb and flow with it,” she says.

Luckily, Dalessandro has a support system that includes her partner, friends and family. Her mother, Gina Dalessandro, is also a small business owner who understands firsthand the peaks and valleys of entrepreneurship. And while their businesses are not quite the same industry, the two are constantly encouraging each other.

Alysse started Ready to Stare just over a decade ago and has since expanded it to include a photography studio space in Rocky River called "The Stare Haus" as well as Secondhand Stare, a secondhand clothing and accessory business. “Starting Secondhand Stare was not only a way to create more representation for plus-sized folks, but a way to show more LGBTQ+ representation as well,” she explains. “We work with models in our full size range—large to 7x—so that really resonates with people. And we’re also trying to make it accessible, so most of the items we have are under $40.”

*Alysse Dalessandro in Rome. (All photos courtesy of Alysse.)*

Representation and access are a huge part of Dalessandro’s mission. As far as her advice goes for other LGBTQ+ individuals wanting to become entrepreneurs, Dalessandro says:

“Be grounded in your mission, and figure out your ‘why.’ Why are you starting this business? Content creation, planning trips and selling secondhand clothes are grounded in this idea that I want to create more visibility and more inclusion in both fashion and travel for plus-size and LGBTQ+ folks. Everything I do goes back to that, and it motivates me more than any dollar amount ever could. Obviously, I need to pay my mortgage, and I need to eat. But being grounded in that mission makes everything that I do worth it.”

For the plus-size and LGBTQ+ travel part of her business, she’s heading to Italy twice this year and making her way to Cuba in September. She acts as a connection point for her groups, working with local companies to provide deep, cultural experiences for them.

“I find the people who take the trips are either really seasoned travelers who want a trip with people who look like them and have the same values,” Dalessandro explains. “They want to go to those off-the-beaten path places like Ortigia—the places you’ve never heard of but are incredibly beautiful, just lesser known.”

Dalessandro is traveling for Pride, too. Pride campaigns make up most of her income every year, but this year might be the exception to the rule. “Usually, I’m out of town for every single weekend during June traveling to different Prides,” she says. But the anti-LGBTQ+ bills have significantly impacted her business. “I also employ three LGBTQ+ contractors, so this doesn’t only hurt me as an LGBTQ+ creator, but it hurts my team and my ability to employ them,” Dalessandro adds.

Dalessandro pinpoints Bud Light’s campaign with Dylan Mulvaney as a turning point for LGBTQ+ content creators. Bud Light sent Mulvaney a can with her face on it to celebrate her transition, which caused a high-profile backlash. While Anheuser-Busch’s support of the LGBTQ+ community is nothing new, Mulvaney is in the public eye versus their more subtle commercials from the ‘90s through today, according to Trav at Queerency.

“That made brands scared. They don’t want the backlash,” Dalessandro says. “This is something I’m hearing across the board from other LGBTQ+ creators.”

Dalessandro explains that she chose to come out because she wanted to be her authentic self in every facet of her business, “but there’s risks to that.” This year, she had a brand tell her that working with her was controversial.

“If we’re not coming to you with these great business ideas right now, we’re tired,” she says. Dalessandro points out that creating opportunities for LGBTQ+ people, making connections, and showing up as allies are ways to support the community.

The negatives can outweigh the positives sometimes, but Dalessandro is hopeful.

“Pride may feel different this year, but it’s always been a fight for our right to exist as our most true and authentic selves,” she says. “This community is resilient, and this year will show that more than ever.”

In honor of Pride Month, Greater Cleveland Partnership is spotlighting local LGBTQ+ businesses, leaders and events throughout June. We’d love your input. Email suggestions to ldemarco@greatercle.com

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