Raskyoli Wine Club & Community.wine

Alessandro Pepe, an Italian entrepreneur with experience in documentaries, theater, and multiple wine bar ventures, founded Raskyoli—a wine bar and restaurant in Rome—with a mission to help people "stop drinking industrial wine and getting back to using wine as a cultural vehicle." When American wine student Lindsay Gabbard came to taste wine at Raskyoli, she was so moved by the experience that she did a complete career u-turn, returning to Italy to become a partner in the business. Together with partner Mattia, they built something special: a place where wine wasn't about technical jargon, but about stories, geography, and deeper cultural understanding.

When COVID-19 hit, the pandemic devastated their physical business. Revenue plummeted 65%—from $200,000 per month down to approximately $90,000. Rather than cutting costs by laying off their 27-30 employees (as many U.S. businesses did), Alessandro and Lindsay made a conscious decision to save the entire team. This constraint forced them to think creatively about how to leverage their brand and expertise in new ways.

They launched two online initiatives: the Raskyoli Wine Club (a subscription service for curated wine shipments) and Community.wine (a free-to-freemium educational platform). By the end of their first year with the wine club, they had grown from 400 members to 800. However, growth stalled at around 900 members by the time of this podcast, with only 100 new members added over the subsequent year. Community.wine attracted 1,200 users but struggled with engagement—it was, by their own admission, "a kind of a strange dark dead place."

Their marketing efforts revealed key insights: paid ads through Facebook and Google hadn't delivered results; their reliance on Mailchimp email campaigns yielded modest conversion (a few subscriptions per day when they aimed for five to seven). They tried hiring a digital marketing agency to create acquisition funnels, but the results were disappointing. What did work was their existing brand authenticity, their 40,000+ email list, relationships with 400+ winemakers, and word-of-mouth referrals. Some wine club members became Community.wine members, and one heavily engaged community member became a paid subscriber.

Their biggest barrier was positioning and audience clarity. They were trying to serve both an Italian market (skeptical of wine clubs as a concept) and an American market simultaneously, but the dual-language platform created confusion. They were "in the middle where people can say no, you're not for me." Additionally, they were unclear on whether to focus on educating aspiring wine enthusiasts or building a B2B community of winemakers and restaurant professionals.

At the time of the podcast, they had 900 wine club members generating roughly $7,500/month (which extrapolates to ~$90,000 ARR from the wine club), 40,000 email contacts, 300+ videos, 400 winemakers in their network, and an open job posting for a chief marketing officer with 450 applications. The hosts suggested several high-potential initiatives: viral short-form video content (e.g., "Why You Should Never Drink Yellowtail"), positioning the wine club as a pandemic-era "replacement date night," launching a massive global virtual wine tasting event to drive community engagement, and doubling down on either the Italian or English-speaking market rather than splitting focus. The vision remains ambitious—if they reach 5,000 members, they could theoretically direct the market for artisan Italian wine globally.