Jason Butcher has lived about 20 lives. Founder of Orbit Capital, a global investment and advisory firm backing over 50 companies across fintech, AI, sustainability, and mental health. Co-founder of Ocean Integrity Caribbean. Board member. Mentor to another 50 founders on top of that. Chief Entrepreneur-in-Residence for the Cayman Islands. He's spent three decades sitting across from founders under pressure — not just writing checks, but getting in the weeds with them on leadership, decision-making, and resilience.
So when Jason talks about habits, he's not speaking from theory.
In this episode, we get into the habit Jason calls his most fundamental one: focus. Not the productivity-hack kind. The intentional, I-have-50-companies-and-10-to-20-calls-a-day-and-I-still-choose-to-be-fully-present-with-you kind. He traces it back to the early 90s when he was publishing magazines with zero digital interruption — and then walks us through exactly how the world engineered distraction into all of us. His take on ADHD will make you think.
We also hear the story of Michael — a founder Jason mentored at an incubator who had a genius product and a terrible pitch. What it took for Michael to break through isn't what you'd expect. It was coachability. Not talent. Not charisma. Openness.
And then Jason goes somewhere few guests go this early in a podcast run. He tells us that at 40, he was diagnosed with early right hemisphere dementia. He's 52 now. And the habit he's actively working on — the one that's hardest — is giving himself grace. Letting go of what he can't remember. Moving forward instead of dwelling. Anchoring back to purpose so that the forgetting doesn't win.
That's where the STORYHabits method comes to life in real time. Jason's value isn't just focus — it's purpose. And once you understand that, his habit of acting immediately, of staying present, of releasing what he can't hold onto — it all makes sense. It's not a workaround. It's who he is.
In this episode:
Why Jason thinks everyone has ADHD now — and why that's actually not a diagnosis, it's a design problem
The Smiley face story: how Jason ended up connected to the global trademark owner of the world's most recognizable symbol, and what it means to him
Michael's story: what separates a founder who takes feedback from one who doesn't — and why coachability is the real differentiator
The dementia diagnosis at 40, and the habit of grace that followed
The STORYHabits moment: anchoring focus and grace onto the value of purpose
Find Jason: Linkedin: https://www.linkedin.com/in/jasonbutcherWeb: http://orbitcapital.net
Looking for mentorship, a different perspective, or just someone to ask for advice? Jason says reach out.
The STORYHabits Podcast is hosted by Connie Kwan. Every episode, we examine the stories that drive your habits — the great ones leaders have built, the bad ones they still wrestle with, and the stories powering all of it.
⚓🎈 Join the STORYHabits book launch team at https://storyhabitsbook.com/launch-team
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