H.I.G.H. (How I Got Here) - podcast cover

H.I.G.H. (How I Got Here)

PlayerProps.ai•podcast.show
Business
Entrepreneurship
Education
Self-Improvement
Careers
H.I.G.H. (How I Got Here) is a weekly show hosted by Trevis Waters — founder of PlayerProps.ai and one of the most unconventional builders in the modern sports world. Each episode features a 1-on-1 conversation with someone who's taken a nontraditional path in sports, betting, content creation, or entrepreneurship. No fluff. No highlight reels. Just real stories, smart risks, and the decisions that shaped the journey. Whether you're a bettor, builder, creator, or someone figuring out your next move — this show helps you learn how others actually got here, and how you might too.
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Episodes

Episode 13 - H.I.G.H. (How I Got Here) Podcast - Kelly Kehn

In this episode, Kelly Kehn shares her career path, beginning with her first job in horse racing and her transition into the iGaming industry. She discusses her experience working for an online sportsbook, her move to a supplier company in the UK, and her role in launching sportsbooks in different markets. Kelly also talks about the founding of her non-profit, the All-in Diversity Project, which aims to support women in leadership, and how her latest venture, Defy the Odds, is working to make en...

Oct 07, 2025•55 min

Episode 12 - H.I.G.H. (How I Got Here) Podcast - Matt Deutsch

In this episode, Matt Deutsch shares his journey from initially wanting to be a veterinarian to becoming a prominent figure in sports media. He recounts his early career in radio, starting with an internship at a community station where he learned every aspect of broadcasting, which eventually led him to his dream job at WFAN [04:47]. Matt then discusses his move to SiriusXM in 2005, where he played a key role in creating the successful SiriusXM Fantasy Sports Radio channel. He explains how he l...

Sep 30, 2025•51 min

Episode 11 - H.I.G.H. (How I Got Here) Podcast - Jim Conventry

In this episode, Jim Coventry shares his story of how he went from dreaming of being a sports broadcaster to becoming a full-time fantasy sports expert. He discusses his educational background in philosophy and his 33-year career as a high school English teacher. Jim explains how his passion for football eventually led him to a part-time writing job and eventually a full-time position at Rotowire, allowing him to finally pursue his dream career [32:55]. He also shares a key piece of advice from ...

Sep 23, 2025•39 min

Episode 10 - H.I.G.H. (How I Got Here) Podcast - Aaron Eisman

In this episode of the "H.I.G.H. The How I Got Here Podcast," host Trevis Waters interviews Aaron Siegel-Eisman, who shares his journey from his time as a basketball player to his current role as a social media agency owner. He discusses the valuable lessons learned from his career path and his pivot into the world of digital marketing and social media.

Sep 16, 2025•42 min

Episode 9 - H.I.G.H. (How I Got Here) Podcast - Steven Kenway

In this episode of the "How I Got Here Podcast," host Trevis Waters interviews Steven Kenway, the CEO of Rolling Insights. Steven shares his career journey, from his childhood dreams of becoming a professional hockey player and actor in Canada [01:15] To his transition into the world of technology. He discusses the valuable lessons he learned from both his early career pursuits, including the importance of staying humble and actively seeking opportunities [07:27]. Steven details his first startu...

Sep 09, 2025•1 hr 9 min

Episode 8 - H.I.G.H. (How I Got Here) Podcast - Gary Moloney

This video is an episode of the "H.I.G.H. The How I Got Here Podcast," hosted by Trevis Waters, with guest Gary Moloney. The episode details Gary's life story, including a near-death experience, his work in responsible gambling, and his journey through education and career. He shares how negative events led him to a better path and a new purpose.

Sep 02, 2025•48 min

Episode 5 - H.I.G.H. (How I Got Here) Podcast - Nic Sulsky

In this episode of "H.I.G.H. The How I Got Here Podcast," host Travis Waters interviews Nic Sulsky, the CEO of The Curling Group. Nic shares his personal journey, from aspiring professional baseball player to a successful entrepreneur in the world of fantasy sports and now, professional curling. Key topics and timestamps: Aspiring to be a professional athlete [01:31:07] Moving to Australia and realizing a new path [03:32:00] Transitioning to the entertainment industry [05:07:29] Creating his own...

Aug 15, 2025•52 min

Episode 4 - H.I.G.H. (How I Got Here) Podcast - Matt McCuen

In this video, Trevis Waters and Matt McCuen discuss Matt's career journey in the sports betting industry. Here are the key takeaways from their conversation: Early Ambitions: Matt's interest in sports broadcasting began in eighth grade [00:23], despite having a speech impediment in his youth [01:05]. He pursued a communications degree with the goal of becoming a sports broadcaster or writer [01:05]. The DeadPres Brand: In 2018, he and his friends created the DeadPres brand on Twitter as a hobby...

Aug 14, 2025•42 min

Episode 3 - H.I.G.H. (How I Got Here) Podcast - Mark Phillip

In this podcast episode, Mark Phillip, CEO of the advertising agency Are You Watching This?! and its gambling arm, Metabet, discusses his career journey and the inspiration behind his companies. Key topics from the interview include: Childhood Dreams: Mark's early aspiration to be a toll booth worker [01:19] and his path from wanting to be a math teacher to studying computer science [02:39]. Dropping Out of College: His decision to leave college in 1999 to pursue his goals in the workforce [03:0...

Aug 13, 2025•47 min
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