Episode 10: Welcome to “The Abyss”: Jonathan Gass Arieli on Consciously Letting Go

In this deeply honest episode of Step Into Next, Leanne and Helaine sit down with entrepreneur, finance leader, and coach Jonathan Gass Arieli for a conversation about resilience, reinvention, and what it really takes to move through the space between what was and what’s next.Jonathan shares the story of building Nomad Financial, supporting high-growth founders, navigating major business success, and then facing the painful unraveling that came with founder misalignment, a difficult sale, and years of uncertainty afterward. From seller financing gone sideways to the emotional toll of leading through instability, this episode goes far beyond the polished version of entrepreneurship.Together, they explore what happens when life keeps “punching” you, how community helps carry us through hard seasons, and why alignment sometimes requires letting go of the very thing you worked so hard to build. Jonathan also opens up about the next chapter of his journey: releasing old identities, closing energetic loops, recognizing personal patterns, and finding a more aligned path through hospitality, home, and deeper purpose.This is a conversation about business, but it’s also about being human: repairing relationships, trusting your inner knowing, and making peace with the fact that we can only make decisions with the information we have at the time.If you’ve ever felt stuck in the liminal space, questioned a major decision, or wondered how to rebuild after disappointment, this episode is for you!