You Need a Little Crazy
Thu Jan 29 2026
In this conversation, Denis Keane shares his journey from a corporate career to entrepreneurship, highlighting the challenges and lessons learned along the way. He discusses his experiences in the nightlife and restaurant industries, the importance of people skills, and the role of adaptability in navigating the ever-changing landscape of startups and technology. Denis emphasizes the need for risk-taking and the value of understanding business fundamentals, while also reflecting on personal growth and self-worth.
Show Notes
This episode presents a profound exploration of career transitions, personal growth, and the entrepreneurial spirit through the lenses of Maricela Herrera and her guest, Denis Keane. The narrative begins with Maricella's honest reflection on her struggles with motivation and the emotional toll of returning to her routine after a significant hiatus. Her vulnerability lays the groundwork for a rich discussion with Denis, whose dynamic background as an entrepreneur in the nightlife and technology sectors illustrates the multifaceted nature of career journeys. Denis recounts his experiences navigating the challenges of establishing a successful nightclub in a gentrifying neighborhood, offering insights into the importance of risk-taking and seizing opportunities. The conversation further delves into the lessons learned from both industries, emphasizing the value of people skills and the necessity of adaptability in the face of uncertainty. As the episode unfolds, listeners are invited to reconsider their definitions of success and the paths they choose, ultimately reinforcing the idea that both personal and professional growth often emerge from embracing chaos and uncertainty.
Takeaways:
In the podcast episode, Dennis Keane discusses the necessity of adaptability in business, emphasizing that the ability to pivot is crucial for success in rapidly changing environments.A significant theme addressed in the interview is the importance of understanding financial metrics, which is essential for running any business effectively, including restaurants and startups.Dennis highlights that personal connections and people skills are indispensable, as they enhance communication and foster a productive workplace culture in both the restaurant and tech industries.The conversation reveals that fear of failure often inhibits individuals from pursuing their passions, and Dennis advocates for embracing risk as an integral part of the entrepreneurial journey.Dennis's journey illustrates how experiences in the restaurant industry can provide transferable skills that are extremely beneficial in the tech startup world, particularly in managing teams and understanding customer dynamics.The episode also touches upon the evolving role of AI in business, suggesting that those who adapt and learn to leverage technology will thrive, while those who resist will likely fall behind.
About Denis Keane:
Denis Keane is an entrepreneur and investor who has founded multiple businesses, backed early-stage startups, and advised companies on growth and business development. Most recently, he served as COO and investor in an AI startup that successfully exited through acquisition. Denis now works with founders and leadership teams to help scale operations and unlock new growth opportunities.
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In this conversation, Denis Keane shares his journey from a corporate career to entrepreneurship, highlighting the challenges and lessons learned along the way. He discusses his experiences in the nightlife and restaurant industries, the importance of people skills, and the role of adaptability in navigating the ever-changing landscape of startups and technology. Denis emphasizes the need for risk-taking and the value of understanding business fundamentals, while also reflecting on personal growth and self-worth. Show Notes This episode presents a profound exploration of career transitions, personal growth, and the entrepreneurial spirit through the lenses of Maricela Herrera and her guest, Denis Keane. The narrative begins with Maricella's honest reflection on her struggles with motivation and the emotional toll of returning to her routine after a significant hiatus. Her vulnerability lays the groundwork for a rich discussion with Denis, whose dynamic background as an entrepreneur in the nightlife and technology sectors illustrates the multifaceted nature of career journeys. Denis recounts his experiences navigating the challenges of establishing a successful nightclub in a gentrifying neighborhood, offering insights into the importance of risk-taking and seizing opportunities. The conversation further delves into the lessons learned from both industries, emphasizing the value of people skills and the necessity of adaptability in the face of uncertainty. As the episode unfolds, listeners are invited to reconsider their definitions of success and the paths they choose, ultimately reinforcing the idea that both personal and professional growth often emerge from embracing chaos and uncertainty. Takeaways: In the podcast episode, Dennis Keane discusses the necessity of adaptability in business, emphasizing that the ability to pivot is crucial for success in rapidly changing environments.A significant theme addressed in the interview is the importance of understanding financial metrics, which is essential for running any business effectively, including restaurants and startups.Dennis highlights that personal connections and people skills are indispensable, as they enhance communication and foster a productive workplace culture in both the restaurant and tech industries.The conversation reveals that fear of failure often inhibits individuals from pursuing their passions, and Dennis advocates for embracing risk as an integral part of the entrepreneurial journey.Dennis's journey illustrates how experiences in the restaurant industry can provide transferable skills that are extremely beneficial in the tech startup world, particularly in managing teams and understanding customer dynamics.The episode also touches upon the evolving role of AI in business, suggesting that those who adapt and learn to leverage technology will thrive, while those who resist will likely fall behind. About Denis Keane: Denis Keane is an entrepreneur and investor who has founded multiple businesses, backed early-stage startups, and advised companies on growth and business development. Most recently, he served as COO and investor in an AI startup that successfully exited through acquisition. Denis now works with founders and leadership teams to help scale operations and unlock new growth opportunities. ORagl5qtiStPlO96oYH4