Magic in the Room #36: Doing What We Love with Special Guest Jake Keyes

December 22, 2020

What does it take to leave behind the relative security of employment and launch into the adventure of entrepreneurship, to do what we love? It all starts in the mind. In this episode, meet Jake Keyes, founder of Skydance Brewing Company, the first Native-owned craft brewery in Oklahoma City. Chris and Hannah explore the mindset shifts that lead to Jake’s success as a brewer and full-time entrepreneur.

Jake is also the host of the  Brewed with Hustle  podcast and proudly reveals that he is the person that likes to sit next to the oldest guy at the bar and talk to him because he loves hearing their stories. But when he spent time in a nursing home, he found himself surrounded by people at the end of their life and every single one of them shared their stories of regret. Jake admits he scared the life out of him.

There was a universal theme to the stories that the residents shared with him. For example, I wish I would have had a better relationship with my son, or I was going to start this business etc. But now they found themselves wrestling with the fact they were going to die with regret. That was the moment where something clicked in Jake’s head, and he promised himself, that would not be him.

The arrival of a global pandemic ensured that 2020 was a turbulent year for businesses. Many people have asked Jake, “Do you ever fear your brewery will fail?” Although he might worry, he always replies, “I fear regret way more than failure” Worrying about his business failing will always be there, but at least he’s given it his best shot and done it.

Jake did not want to be the guy in the nursing home who’s got a lot of regrets because they didn’t create the things they wanted to or ended up living somebody else’s life because that’s what they were told you do. Jake shares how he has many friends who are trying to start their own business but talk themselves out of it.

There is one friend who has got a long list of things he wants to do. He’s got the ability, the talent, but his wife is afraid of that. Removing the safety net of not having a regular job with the securities that come with it is holding them both back. But Jake argues that it’s much scarier to be dependent on somebody else to do well in business and keep paying you.

Chris also shares how that veil of security really isn’t secure. It’s, it’s just a system that we’ve placed a lot of value in. But he encourages entrepreneurs to pave the runway and prepare. Unfortunately, it’s not as simple as being employed by a company today and tomorrow going, independent. Much of the building can be done alongside your day job in your spare time.

Hannah and Chris were all inspired by Jake’s moving and inspiring stories. They would also love to hear from the listeners from their podcast community. If you are thinking about leaving the relative security of employment and be in charge of your own destiny or have already been on that journey, please share it with us.

 

 

 

 

 

 

 

Magic in the Room #201: Leading from Within

By Emma Holland • June 9, 2026
In this episode of Magic in the Room, Chris Province, Hannah Bratterud, and Luke Freeman reflect on six years of conversations and explore a foundational leadership question: why leadership is ultimately an inside game. Drawing on personal growth, facilitation experiences, and organizational leadership lessons, they argue that effective leadership cannot be reduced to frameworks, checklists, or techniques alone, but instead depends on the ongoing work of self-awareness, discernment, courage, and wisdom. They explore the relationship between courage and conviction, the importance of responding rather than reacting, and the role of personal development in creating positive impact for teams, organizations, and communities. The episode presents leadership as a lifelong practice of leading oneself first, emphasizing that meaningful change begins not with external systems, but with the internal work of becoming more intentional, hopeful, and aligned with one’s values.

Magic in the Room #200: How to Lead through Polarities

By Sarah Whitfield • May 5, 2026
In this episode of Magic in the Room, Luke and Hannah explore the concept of polarities. Tensions like purpose and performance, stability and change, or accountability and grace that are often mistaken for problems to solve rather than dynamics to manage. Drawing on insights from Barry Johnson’s work, they explain how these opposing forces are interdependent and must be balanced over time to achieve sustained success. Through practical examples and personal reflections, they show how over-relying on one side of a polarity leads to predictable “shadow sides” such as stagnation, chaos, inefficiency, or burnout, while effective leadership requires recognizing where you are on the cycle and intentionally recalibrating. The episode emphasizes that many recurring organizational frustrations are not failures, but signals of imbalance, and offers a more nuanced approach to leadership. One that replaces rigid either/or thinking with flexible both/and awareness to improve decision-making, team dynamics, and long-term performance.
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