Too Millennial: Unleashing the Next Generation of Leaders

In this episode, Jessy sits down with Christina Cheuk—positive psychologist, CEO of Two Happy, and Assistant Professor at University of Pennsylvania, where she teaches under the legendary Marty Seligman. Together they explore a powerful shift in how we think about leadership, well-being, and what really fuels us: mattering.

Together, they unpack why purpose alone isn’t enough—and why our sense of impact and being seen matters.

Key Re...

In this episode, Jessy Grossman gets personal about the question: “Am I too disruptive?” She explores the evolving concept of disruptive leadership, sharing how the courage to challenge the status quo can be both a strength and a struggle.

Through the lens of her own experiences as a disruptor, Jessy unpacks how effective leaders can channel disruption into positive transformation.

This episode invites listeners to rethink disruption...

Join Jessy Grossman and Sarah Malone as they explore Appreciative Leadership, a strengths-based approach to leadership and organizational development. Discover how recognizing individual strengths, fostering respectful communication, and building a positive culture can transform teams.

This episode highlights the transformative impact of Appreciative Leadership and the crucial role mindset plays in effective leadership. Perfect for...

Women Ascend

In this conversation, host Jessy is joined by Yara and Margaret to understand the multifaceted landscape of women’s leadership. Together, they unpack the unique trends, challenges and opportunities women encounter in the workplace, emphasizing the importance of intersectionality and community support in driving meaningful change.

The conversation sheds light on societal expectations, generational differences, and self-...

Time Flow, Cash Flow & Team Flow for Optimal Performance?

Join host Jessica Grossman as she sits down with Dr. Orin Davis to explore the nuances of team dynamics, the art of deliberate "team building," and the challenges of fostering true inclusion within teams. Dr. Davis introduces the concept of "team flow" and discusses its pivotal role in achieving peak team performance. Together, Grossman and Davis delve into essential t...

In this insightful conversation, Jessy Grossman and Allie Stark delve into the critical aspects of leadership coaching and the interplay between the inner and outer game of leadership. They discuss how self-awareness, self-regulation, and the process of unlearning are vital for effective leadership development. Additionally, they emphasize the importance of resilience—not just as a personal trait but as a product of supportive syst...

In this episode, Jessy Grossman welcomes Libby Rodney, Chief Strategy Officer at The Harris Poll and futurist, to discuss the latest cultural and workplace trends impacting Millennial leaders. They explore topics such as quiet vacationing, the effects of layoffs on employee engagement and innovation, and the vital role of vulnerability in both parenting and leadership. This episode provides actionable strategies and data-driven ins...

The Power of Manifestation? Moving from Chaos to Clarity

In this enlightening conversation, Jessy and Nicole dive deep into the concepts of manifestation and intention setting, exploring how these practices can shape leadership's vision and purpose. At the ~20-minute mark Nicole leads listeners through a guided practice designed to help them experience manifestation and intention setting firsthand, fostering clarity, strength and...

In this episode of Too Millennial, host Jessy Grossman interviews communications expert and CEO of Career Civility, Jenna Rogers, to explore the evolving role of email in workplace communication and strategies for mastering it. They dive into the challenges of writing impactful emails, navigating power dynamics, and the lack of formal training in email communication. Jenna shares practical tips on establishing clear communication n...

Belonging, Ego & High Performing Teams

In this thought-provoking episode, Jessy Grossman and Ashly Williams discuss the intricate dynamics of ego, competition, and fear in the workplace, shedding light on how these elements perpetuate toxic environments.

Ashly Williams shares poignant anecdotes highlighting the systemic disparities and racism prevalent in many workplaces, emphasizing the urgent need to create a sense of belongi...

Leadership that Unlocks Peak Performance

 In this episode, host Jessy Grossman interviews Brian Gelber, a successful trader, visionary leader and Co-Founder of the proprietary trading firm Gelber Group. Gelber emphasizes that to achieve higher performance, one must cultivate self-awareness and prioritize well-being. This episode dives into Brian Gelber's journey, from being a successful trader to leading Gelber Group, and the l...

Exploring the Interplay of Mind and Body for Wellbeing

In this conversation, Jessy interviews Nicole Belica, a yoga teacher and mindfulness coach, about the importance of embodiment and its role in leadership. They discuss how embodied leadership allows us to be present in the moment and respond to stressors in a healthy way. 

Nicole shares practical tips for cultivating embodied leadership, such as deep breathing and paying attent...

Embracing Mistakes for Growth

In episode #3 of Too Millennial, Eve & Jessy explore ways to move forward from mistakes, emphasizing the importance of self-care, grace, and self-compassion while striving for excellence. 

Jessy starts the episode by delving into the struggle many leaders face: trapped in a whiplash cycle that moves from chaos (too much empathy) to rigidity (too much accountability). To navigate this challenge, she...

…because we can't solve earth's most pressing issue without a healthy team.

In part 1 of my episode, with Executive Director & Author Eve Turow-Paul, we explore how having healthy people is crucial for organizations to innovatively tackle pressing threats of climate change.

Together, Jessy and Eve explore concepts from Eve’s book, "Hungry" and self-determination theory, relating them to her approach to leader...

In the inaugural episode of 'Too Millennial,' Jessy embarks on a quest to uncover the truth: is she still considered “Too Millennial”?

As Millennials step into their prime years of adulthood, it's high time for a reassessment. They’re no longer the fresh-faced rookies demanding a seat at the table; instead, they’re at the table, grappling with the newest crop of Gen Z.

Join Jessy as she debunks stereotypes like ‘trophy ...

After countless sessions of leadership coaching and team consulting, Jessy knows that leadership needs to be reimagined. Fueled by frustration with outdated work norms and witnessing clients on the edge of burnout, she's left with a burning desire for a better way of working. And so, this podcast is on a mission – a mission to explore what leadership looks like as Millennials, the "snowflake, self-centered generation"...