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.
All content for H.I.G.H. (How I Got Here) is the property of PlayerProps.ai and is served directly from their servers
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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.
Episode 9 - H.I.G.H. (How I Got Here) Podcast - Steven Kenway
H.I.G.H. (How I Got Here)
1 hour 9 minutes 22 seconds
2 months ago
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 startup venture with a friend, its initial failure, and how a successful pivot led to a profitable acquisition [13:14].
He then explains the inspiration behind his current company, Rolling Insights, and its product, Sportswise, which aims to democratize sports data for fans and businesses [19:07].
H.I.G.H. (How I Got Here)
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.
