EP 289 Building Culture, Resilience, and Brands: Lessons from XSET CEO Greg Selkoe

In this powerful episode of the Stuck In My Mind Podcast, host Wize El Jefe welcomes visionary entrepreneur Greg Selkoe, best known for founding the influential streetwear brand Karma Loop, leading the esports powerhouse Faze Clan, and now steering the cutting-edge gaming lifestyle brand XSET as CEO and co-founder. This honest, inspiring conversation is a masterclass for creators, culture builders, and anyone pursuing a dream against the odds. From the jump, Wize El Jefe sets the stage, giving listeners a glimpse into Greg Selkoe’s cultural impact—from collaborations with icons like Lil Wayne, Osuna, and Pharrell’s camp, to partnerships with brands like the Boston Red Sox and HyperX. But as the episode unfolds, it’s clear this story goes much deeper than flashy names and million-dollar deals—it’s about authentic passion, grit, resilience, and growth. The Roots of Culture Building The episode kicks off as Greg Selkoe traces his journey from Boston’s vibrant street culture to global entrepreneurship. He reveals how an early obsession with breakdancing, graffiti art, skateboarding, punk rock, and hip hop influenced his worldview. Rather than seeing these movements as separate lanes, he felt at home in all of them—setting the stage for Karma Loop, which wasn’t just about selling clothes, but celebrating the energy and diversity of urban culture. Greg Selkoe describes how this merged into his approach at XSET, aiming to build “a media company” that puts culture first, amplifies creators, and tells compelling brand stories. Resilience Through Setbacks One of the episode’s major themes is resilience. Both Greg Selkoe and Wize El Jefe reflect on their entrepreneurial journeys, emphasizing that setbacks and failures are inevitable. Greg Selkoe shares candidly about Karma Loop’s highs and lows—from its $150 million peak to private equity challenges that forced him to rebuild from scratch. He offers hard-earned lessons: “Don't think someone's going to come along and save you if you're having trouble in your business, you got to rely on yourself.” The best way not to fail? Keep going. Wize El Jefe reciprocates, sharing his own risk-taking path in podcasting, internet radio, and launching a media company. The key takeaway is treating each setback as a learning experience—a stepping stone rather than an endpoint. Business Lessons That Transcend Formal Education Unlike many entrepreneurs, Greg Selkoe didn’t start with a business degree—he studied urban planning at Harvard, inspired by his mother’s work. But he credits this background for shaping his community-first approach. “Passion for what I was doing came from another part of me than what normally would be... I think that authenticity came through everything we did.” Rather than targeting a market, he built organically around what he loved—and learned the other business skills on the job and through mentorship. This authenticity, he believes, gave his brands a unique edge and fostered community. Building XSET and Shifting Strategies When it came to launching XSET, Greg Selkoe and team faced fresh challenges: securing investment, building a fanbase, and educating skeptical investors about the true scale of gaming and streaming culture. Greg Selkoe recognized a major opportunity—gaming needed a lifestyle brand that felt as dynamic as Overtime, Complex, or Barstool. The vision from day one: XSET would be a lifestyle media company at the crossroads of gaming, music, fashion, entertainment, and traditional sports. However, this path wasn’t linear. Initially, XSET tried to replicate Karma Loop’s retail-first model, but the lack of an established fanbase made traction difficult. After two years, they made a pivotal shift—refocusing on media, content, and creator empowerment. This willingness to pivot, rather than stubbornly sticking to a plan, is a recurring lesson for entrepreneurs highlighted in the episode. Collaboration, Community, and Advice for Creators Both host and guest agree: entrepreneurship is not a solo sport. Greg Selkoe stresses the importance of asking for help, seeking mentorship, and learning from those who have traveled similar paths: “If you don't know something... that's power to say you don't know it.” He shares stories of leaning on collaborators and mentors—even in public adversity—while cautioning against burning bridges or stepping on others to succeed. Public Challenges, Private Pain, and the Power of Community The episode delves into the emotional toll of public failure. Greg Selkoe recounts the fallout from Karma Loop’s bankruptcy, facing media scrutiny and industry criticism. Yet, a pivotal moment at a high-powered Silicon Valley barbecue hosted by Steve Stout and Ben Horowitz transformed his outlook. Instead of derision, he found encouragement and solidarity from fellow entrepreneurs—reminding him that to build is to stumble, but also to rise again. This network of support ...