H.I.G.H. Ep. 41 | Josh Hansen of Rolling Insights

H.I.G.H. Ep. 43 | Adam Bjorn of Plannatech

Just dropped: H.I.G.H. Episode 43 with Adam Bjorn of Plannatech Adam’s story is one of curiosity, persistence, and figuring things out one step at a time. Before founding Plannatech, there were years of experiences, challenges, and moments that slowly shaped the path he would eventually take into technology and entrepreneurship. That’s what this episode focuses on. Not just the business today. The full journey behind it. We rewind all the way back and talk through: • The early interests that shaped how he thinks • How technology first became part of his life • The moments that pushed him toward building something of his own • Lessons learned through uncertainty, setbacks, and risk • What it actually takes to keep moving forward while building from scratch What stood out to me most is how much entrepreneurship is really about adaptation and continuing to learn in real time. If you’re building something, navigating uncertainty, or trying to create your own path, this conversation is worth your time.

H.I.G.H. Ep. 42 | Ryan Robey of STAICY

Just dropped: H.I.G.H. Episode 42 with Ryan Robey of STAICY Ryan’s journey is a reminder that careers are rarely linear. Before building STAICY, there were years of experiences, interests, risks, pivots, and moments that slowly shaped the direction of where he would eventually end up. That’s what this episode is about. Not just the company. The full path behind it. We rewind all the way back and talk through: • The early influences that shaped his mindset • How technology and sports became part of his journey • The moments that pushed him toward entrepreneurship • The uncertainty and lessons that came with building something from scratch • What he learned through the highs, setbacks, and pivots along the way What stood out to me most is how much of success comes from continuing to move forward before the outcome is clear. If you’re building something, navigating uncertainty, or trying to carve out your own path, this conversation will resonate.

H.I.G.H. Ep. 41 | Josh Hansen of Rolling Insights

Episode 41 of H.I.G.H. (How I Got Here) with Josh Hansen of Rolling Insights This episode is a full rewind into the journey that led Josh into sports, analytics, fantasy, and ultimately entrepreneurship. Before building Rolling Insights, Josh was simply someone fascinated by sports, numbers, competition, and trying to understand patterns long before data became such a massive part of the industry. That’s what this conversation focuses on. Not just the company. The path behind it. We talk about: • The early experiences that shaped his mindset • How sports and analytics first became an obsession • The evolution from interest to opportunity • The risks and uncertainty that come with building something from scratch • The moments that changed the direction of his career What stood out to me is how much of Josh’s journey came from leaning deeper into genuine curiosity over time until it eventually became a business. If you’re building something in sports, tech, analytics, or entrepreneurship, this episode has a lot of valuable perspective. Would love to hear your biggest takeaway. #sportsbetting #sportsanalytics #entrepreneurship #startup #sportsbusiness #podcast #howigotHere

H.I.G.H. Ep. 40 | Jesse Learmonth of BettingStartups.com

Episode 40 – H.I.G.H. (How I Got Here) Podcast | Jesse Learmonth Before launching Betting Startups, Jesse Learmonth was navigating his own path through media, entrepreneurship, and the betting industry. This episode is a full rewind of that journey. We go back to the beginning. The early influences, the environments he was exposed to, and the moments that gradually pulled him toward startups, writing, and the betting space. This is not about where he is now. It’s about how he got there. In this episode: • Early interests and influences that shaped his thinking • First exposure to startups and the betting industry • The decision to start writing and building in public • Lessons learned from navigating uncertainty and risk • The key turning points that led to Betting Startups • What it takes to stay consistent and build something over time Jesse’s story is a reminder that opportunities tend to follow people who stay curious and keep showing up, even when the path isn’t clear yet. About H.I.G.H. (How I Got Here) Hosted by Trevis Waters, this podcast rewinds the full life journey of today’s top figures in sports, media, and betting. From childhood to present day, we focus on the real path, not just the outcome. Subscribe so you never miss an episode Like if this story resonated Comment your biggest takeaway

H.I.G.H. Ep. 39 | Ken Crites: From IT to Retiree

Episode 39 – H.I.G.H. (How I Got Here) Podcast | Ken Crites Before becoming a familiar name at RotoWire, Ken Crites was simply navigating his own path, long before fantasy sports became what it is today. This episode is a full rewind of that journey. We go back to the beginning. The early stages, the environment he came up in, and the moments that gradually pulled him into the world of fantasy sports and content. This is not about where he is now. It’s about how he got there. In this episode: • Life before fantasy sports was mainstream • Early influences and interests that shaped his path • How he first got pulled into fantasy sports • The key decisions and turning points along the way • The ups and downs that don’t get talked about • What it takes to stay consistent long enough to build something lasting Ken’s story is a reminder that success in any industry is rarely immediate. It’s built over time through curiosity, consistency, and sticking with it before it’s obvious to anyone else. ⸻ About H.I.G.H. (How I Got Here) Hosted by Trevis Waters, this podcast rewinds the full life journey of today’s top figures in sports, media, and betting. From childhood to present day, we focus on the real path, not just the outcome. Subscribe so you never miss an episode Like if this story resonated Comment your biggest takeaway