When asked about how he landed his current role at Underdog Fantasy, Steve explained that his journey was a mix of experience, networking, and timing. Over the years, he built a diverse resume that included working at NESN, Bleacher Report, Barstool Sports, Audacy, Sports Illustrated, and NBC Sports Boston. Each role gave him new skills and connections, which ultimately helped him land opportunities down the line. I asked which specific jobs played the biggest role in his career. Steve pointed to two key experiences: NESN and Bleacher Report. “I’ve definitely been able to get a lot of experience. I mean, the main ones are NESN and Bleacher Report. Those are the two main ones that led me here.”
Steve also noted that his time co-hosting the Section 10 Podcast at Barstool Sports played a huge role in his career growth. The podcast built a strong following, and when he parted ways with Barstool in 2021, it remained a defining part of his brand. When Underdog Fantasy became the new home of Section 10, the opportunity to reunite the show made perfect sense. His experience in content creation, social media, and sports media made him a natural fit for a co-hosting and social media associate role with Underdog Fantasy. Beyond Section 10, Steve contributes to other projects at Underdog, further expanding his role in sports media.
One of the most pivotal moments in Steve’s journey came when he discovered the Section 10 Podcast. He recalled how it all started when he noticed his former NESN colleague, Gary Striewski, retweeting an episode he appeared on. “I end up seeing my buddy Gary Striewski (who I worked with at NESN at the time) retweeted being on this Red Sox podcast, Section 10, and I’m like, I have no idea what this is, but I saw the logo—it looks kinda cool and it was Red Sox-related. And that’s really all I cared about. Still really all I care about. So I asked what’s this about and he’s like, ‘Dude, I had a lot of fun.’” Intrigued, Steve dug a little deeper and realized that his former Endicott classmate, Pete Blackburn, was a co-host alongside Jared Carrabis. This personal connection motivated him to reach out to Jared. “So I reached out to him on LinkedIn, and that’s, by the way, the only time I’ve ever reached out to somebody on LinkedIn. But I reached out saying I’d love to get involved in any way, shape, or form. And Jared was like, ‘This is actually perfect timing, we’re actually looking for a producer.’” What started as a producer role quickly grew into something bigger. Over time, Steve expanded his role with Section 10, eventually transitioning to a full-time co-host—a position he still holds today.
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