I first met Oli through The Last Drop in 2023, when he reached out to collaborate on marketing ideas for the Whistler GranFondo. From the very first conversation, I could tell this was someone who didn’t just think differently, he thought deeply. He was generous with his time, relentless about fair value exchange, and always looking for ways to make the outcome better for everyone involved.
At one point, when I told him I couldn’t film the Fondo because I had to be back at my day job by 2pm, Oli replied: “What if we get you back by helicopter?” That’s just who he is. Practical, bold, first-principles thinking - always making his own path.
Oli has been instrumental in keeping the GranFondo running smoothly alongside Neil year after year. But beyond his role in events, he’s now carving a new lane: helping people reconnect with their essential truth and rise toward their highest selves. It’s a pivot that feels less like reinvention and more like alignment.
The Path to Purpose
For Oli, purpose wasn’t obvious at first.
“In some opaque way, I've felt for a while that I have a gift to offer the world. I just wasn't able to pinpoint what exactly it was.”
Raised in an era that preached the traditional ladder - education, career, house, retirement - Oli struggled with the feeling that something was missing. Even with success by many measures, the nagging sense of “more out there” never went away.
Through challenge, depression, and reflection, he realized he was meant to create something truer: a space for others to rediscover who they are, not who the world tells them to be.
A Mindset of Long-Term Growth
Oli knows what it means to build slowly and intentionally.
“Showing up with consistency over time flattens out the noise, accumulates powerfully, and outperforms nearly everything else on earth - with your sanity intact.”
That long-term focus, coupled with trust in his intuition, has guided him through uncertainty and into the work he now leads as an Inner Elevation Guide.
Progress on His Terms
For Oli, progress is no longer about ticking off conventional milestones.
“Am I moving more towards who I am, or away from it? If it's the former, it's progress.”
Whether it’s helping someone move past blocks in their life or building financial freedom quietly in the background, his work is measured less by speed and more by alignment.
The Plain Pillars
Impact First
“Sharing stories, asking questions and creating offerings that allow people to receive value and connection without being asked for anything in return.”
Identity is Earned
“How you choose to live your life and treat others dictates the richness of the life you lead. You have to practice what you preach, build for the long term, and not hold expectations.”
Small Bets, Big Ideas
“My first bitcoin investment went up 25% and then dropped in half. That moment taught me to educate myself, stay curious, and be brave enough to lean into discomfort. It opened the door to finance, philosophy, and future trends.”
The Middle of the Journey
Right now, Oli is in the middle—not at the finish line, not at the beginning.
“In truth, this energy, while frustrating, has also been a gift. The sheer amount of time I’ve felt it building tells me that what is coming is incredibly meaningful. This isn’t a hobby, it’s a mission.”
If he could whisper advice to someone about to start their own path?
“Ask yourself: is this what you truly want? If it’s not a hell yes, it’s a no. There’s something greater you’re meant to be doing—even if it’s not ready to be birthed yet.”
Follow Oli: @olibobbbb
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