This episode of A Productive Conversation features Chris Dalla Riva, a musician, data analyst, and Senior Product Manager at Audiomack who bridges the gap between creativity and analytics. Chris joins me to discuss his book Uncharted Territory: What Numbers Tell Us About the Biggest Hit Songs and Ourselves.

As part of his research, Chris listened to every Billboard Hot 100 number-one song—nearly 1,200 of them—tracking trends, rating songs, and discovering how randomness, technology, and taste shape what becomes a hit. We explore the intersection of numbers and nuance, how data can deepen our understanding of art, and what the patterns of pop music reveal about us.

Six Discussion Points

• The origin of Chris’s experiment to listen to every Billboard number-one hit
• Why Bob Dylan never topped the Hot 100—and what that says about luck and timing
• How data, subjectivity, and quality intertwine when rating songs
• The cyclical nature of musical trends, from movies to TikTok
• The uneasy relationship between music and technology—from Auto-Tune to AI
• Why the album format—and vinyl—still matter in a streaming world

Three Connection Points

• Check out Chris's newsletter
• Buy Chris's book
• Read Mike's essay, The Sound of Time

Chris and I cover a lot of ground in this conversation—from Bob Dylan’s surprising chart record to the influence of AI on modern music. If you’ve ever wondered what hit songs say about culture, creativity, and ourselves, this episode hits all the right notes.

This latest edition of our monthly PM Talks series dives into a topic that underpins nearly everything we do: trust. From trusting the moment you’re in to trusting the systems you build, Patrick Rhone and I explore how this single word quietly defines the way we live, work, and connect.

In this conversation, we move from the personal—trusting ourselves, our instincts, and our attention—to the societal, exploring what happens when trust erodes in our institutions, technology, and even the tools meant to make life easier.

Six Discussion Points

• Why trusting the moment enhances presence—and how presence strengthens trust.
• How trust manifests in everyday choices, like buying a car or managing a calendar.
• The connection between simplicity, minimalism, and building trustworthy systems.
• Why democracy, money, and even productivity all rest on unseen foundations of trust.
• The difference between a trusted system and your trusted system.
• How patience, presence, and attention preserve trust over time.

Three Connection Points

• Patrick's blog post on trust
• Watch The Big Short and/or Margin Call
• Listen to Episode 596: Curiosity | PM Talks S2E3

Trust isn’t static—it’s something we build, test, and sometimes rebuild. Whether you’re trying to trust your tools, your timing, or yourself, I hope this episode helps you see where trust already lives in your life—and where it might need a little reinforcement.

In this episode of A Productive Conversation, I sit down with James Kimmel Jr., JD — a Yale lecturer, lawyer, and leading researcher on the neuroscience of revenge. His new book, The Science of Revenge: Understanding the World’s Deadliest Addiction—and How to Overcome It, explores why our brains crave retaliation and how forgiveness can literally rewire us toward peace.

Our conversation begins with a deeply personal story that shaped James’s life’s work and unpacks how revenge functions like an addiction — one fueled by pain, dopamine, and unchecked desire. What follows is a fascinating look at how our minds process grievance, why forgiveness is a neurological superpower, and how awareness can keep us from being consumed by cycles of anger and retaliation.

Six Discussion Points

• How a violent act of bullying led James to study the neuroscience of revenge
• The brain’s pain and reward circuits — and how they make revenge feel like a drug
• Why grievances compound and can trigger impulsive reactions
• The distinction between self-defense, grief, and revenge
• How forgiveness shuts down the brain’s pain network and restores self-control
• Why awareness, reflection, and tools like journaling can help break the revenge cycle

Three Connection Points

• Get James's book
• Visit James's website
• Check out the Miracle Court app

This conversation reminded me that the pause — that small, deliberate moment between grievance and reaction — can change everything. James’s work shows us that forgiveness isn’t about excusing others; it’s about freeing ourselves. I hope this episode helps you reflect on where small moments of release might lead to greater clarity, peace, and yes, productiveness.

In this episode, I sit down with Hannah Bookbinder, founder of AcademicAlly, LLC, and creator of the MyTOAD App—an innovative tool designed to help people manage time, organization, accountability, and focus. With over 25 years of experience supporting neurodivergent individuals, Hannah brings both expertise and empathy to the conversation.

We explore how understanding one’s unique wiring leads to better productivity and a stronger sense of agency. Hannah’s insights reveal how reframing ADHD through curiosity, compassion, and structure can turn what feels like chaos into capability.

Six Discussion Points

• The story behind the MyTOAD App and how it helps users manage time, organization, accountability, and focus.
• Why “Eat That Frog” doesn’t always work for neurodivergent minds—and what to do instead.
• How self-awareness and emotional check-ins can transform productivity habits.
• The role of journaling as both reflection and regulation—tailored to each individual’s comfort level.
• Rethinking ADHD: seeing it as a source of strength rather than a villain to defeat.
• How Hannah’s mission now extends beyond individuals to schools, businesses, and healthcare organizations.

Three Connection Points

• Check out MyTOADApp
• Read the book
• Check out Hannah on Instagram

This conversation with Hannah reminded me that productivity isn’t about conformity—it’s about compatibility. When we learn to align with our wiring instead of resisting it, we uncover the capacity to work with time instead of against it. Whether you’re neurodivergent or simply human, there’s wisdom here worth dialing into.

In this episode of A Productive Conversation, I sit down with Anthony Verdino — a licensed clinical social worker and author of CBT Simplified. Drawing from both his professional expertise and personal story of resilience, Anthony shares how cognitive behavioral therapy (CBT) can be applied beyond the therapy room — into the way we think, act, and feel in our everyday lives.

We explore how small shifts in thought and behavior can create profound changes in productivity and well-being, especially in a world that often mistakes busyness for progress. Anthony offers practical ways to align mindset with action and shows how reframing, acceptance, and self-care can transform not just how we work, but how we live.

Six Discussion Points

• The core principles of CBT and how Anthony distilled them into a simple, visual model
• How self-monitoring and self-assessment connect directly to productivity and personal growth
• Why reframing “should” into “could” turns guilt into empowerment
• The danger of perfectionism and how embracing imperfection fosters balance and progress
• The role of self-care and mindfulness in preventing burnout and building resilience
• How to make CBT principles second nature through consistent reflection and small, mindful actions

Three Connection Points

1. Anthony's website
2. Anthony's book
3. My TEDx Talk: “How to Stop Time”

Our conversation reminded me how productivity and psychology share the same foundation: awareness and choice. Whether you’re managing your focus, emotions, or time, the work begins by observing your thoughts, reframing them, and then moving forward — not perfectly, but intentionally.

When you’re managing ADHD—or simply navigating the distractions of modern life—traditional productivity tools often fall short. My guest, Skye Waterson, knows this better than most. A former academic turned ADHD coach and founder of Unconventional Organisation, Skye has helped hundreds of professionals—from entrepreneurs to executives—craft systems that support their unique brains instead of fighting against them.

In this conversation, Skye and I explore the science behind ADHD, the myths that persist around productivity, and how to design frameworks that meet you where you are. Whether you’ve been diagnosed, suspect you might have ADHD, or simply want to focus better in a world full of noise, this episode offers practical wisdom grounded in research and real experience.

Six Discussion Points

• The turning point during Skye’s PhD that led to her ADHD diagnosis—and her shift from academia to coaching.
• Why common productivity systems like the Pomodoro Technique aren’t built for ADHD brains.
• How dopamine differences influence motivation, focus, and task initiation.
• The “Focus Formula” method Skye teaches high-achieving clients to identify what’s truly urgent and important.
• The role of transitions, zones, and small “dopamine boosters” in sustaining attention.
• How leadership and neurodiversity intersect—and why we need more research on ADHD in executive roles.

Three Connection Points

1. Unconventional Organisation
2. The ADHD Skills Lab Podcast
3. Episode 625: Jesse J. Anderson Talks About ADHD, Extra Focus, and Finding Flow

Talking with Skye reminded me that productivity is never one-size-fits-all—it’s about alignment, not conformity. Her evidence-based yet deeply human approach to ADHD management offers lessons anyone can apply: simplify, start small, and give yourself permission to work with your brain, not against it.

This episode is the latest in our monthly series PM Talks, where Patrick Rhone and I dive into ideas that shape the way we approach work, time, and life. In this conversation, we explore the theme of clarity—how it shows up in our days, why it matters, and what can get in the way of it.

Patrick and I both share personal stories—from missed football games to unexpected ISP issues—that highlight how clarity isn’t something we stumble upon, but something we need to cultivate. We talk about how structure and spontaneity coexist, and how clarity can be found even when life throws curveballs (or waves, as one Zen monk would put it).

Six Discussion Points

• Why sports outcomes and emotional responses can affect clarity in daily life
• The value of scaffolding (like time theming) to provide focus without rigidity
• Lessons from the New Yorker article Can You Really Live One Day at a Time?
• Insights from Paul Loomans’ Time Surfing and how it relates to productivity practices
• The role of feelings: how they can cloud or create clarity
• The practice of taking a “Clarity Day” to step back, reflect, and reset

Three Connection Points

• Patrick Rhone’s Website
• The Productivity Diet by Mike Vardy
• “Can You Really Live One Day at a Time?” – The New Yorker

Clarity isn’t about controlling every moment—it’s about navigating the waves of life with intention and awareness. I hope this episode gives you a chance to pause, reflect, and maybe even consider setting aside your own Clarity Day.

In this episode of A Productive Conversation, I sit down with Jesse J. Anderson, a writer, speaker, coach, and ADHD advocate whose work has resonated with countless people navigating life with ADHD. He’s the author of Extra Focus: The Quick Start Guide to Adult ADHD and the voice behind the popular newsletter of the same name.

Jesse brings a mix of humor, honesty, and lived experience to the conversation. We dive into the challenges of attention, time, and motivation—and the strategies that can help not only those with ADHD, but anyone who wants to work with their brain instead of against it.

Six Discussion Points

• How Jesse’s diagnosis at 36 reframed his past struggles and opened new possibilities.
• The concept of the “clockless mind” and why time feels so different for those with ADHD.
• The oscillation between friction and flow—and how to recognize both.
• Jesse’s “4Cs” framework (Captivate, Create, Compete, Complete) for unlocking motivation.
• Rejection Sensitive Dysphoria (RSD) and how it impacts relationships and self-perception.
• Why strategies like adding action verbs to tasks and “eating the ice cream first” can help create momentum.

Three Connection Points

• Jesse's Extra Focus newsletter
• Get Jesse's Book
• Listen to APC 164: Faster Than Normal with Peter Shankman

Talking with Jesse reminded me that productivity isn’t one-size-fits-all. Whether you live with ADHD or simply want to work more effectively, strategies like the 4Cs and reframing how you view time can shift the way you approach your day. I hope you’ll check out Jesse’s work and experiment with some of these ideas yourself.

On this episode of A Productive Conversation, I sit down with Leslie Grandy, author of Creative Velocity: Propelling Breakthrough Ideas in the Age of Generative AI. Leslie is a global product executive turned CEO advisor who helps organizations unlock creative thinking to accelerate growth. Her decades of leadership at Apple, Amazon, Best Buy, and T-Mobile give her a unique perspective on how creativity, technology, and leadership intersect.

Our conversation explores why creativity isn’t limited to artists, how space and time fuel ideation, and what role emotional regulation plays in sustaining momentum. We also dig into how precision, AI, and frameworks can both hinder and propel breakthrough ideas. If you’ve ever doubted your own creativity—or wondered how to harness it consistently—you’ll want to hear this one.

Six Discussion Points

• Why many professionals mistakenly believe they aren’t creative—and how to reframe that thinking.
• The power of space—whether walking, running, or even showering—in activating creative flow.
• Precision as both a driver and deterrent of creative velocity, depending on how it’s applied.
• Emotional regulation and equanimity as essential tools for sustaining creativity without burnout.
• How to think about velocity beyond speed—focusing on predictability, quality, and intentional triggers.
• Using AI as a creative collaborator through structured frameworks to expand possibilities without chaos.

Three Connection Points

• Get Leslie's book
• Watch John Cleese’s classic talk on creativity
• Check out NotebookLM

This conversation with Leslie reminded me that creativity isn’t an exclusive club—it’s a capacity we all share, provided we give ourselves the time, space, and intention to use it. Whether you’re leading a team, writing your next book, or simply looking to bring more meaning to your daily choices, Leslie’s insights on creative velocity offer a clear path forward.

I had the chance to sit down with Neil Ghosh, a seasoned executive whose work has spanned the nonprofit, government, philanthropic, and private sectors. He’s also the author of Do More Good: Inspiring Lessons from Extraordinary People, a book filled with stories of leaders, visionaries, and everyday people who embody the power of empathy, courage, and action.

In our conversation, Neil and I dove into the importance of perspective, why empathy isn’t a “soft” skill but a strategic one, and how small actions can have extraordinary impact. We explored how his upbringing in Kolkata shaped his worldview, the lessons he learned from people like John McCain and Shimon Peres, and why legacy is something you influence—but never fully control.

Six Discussion Points

• Why doing more good is different from simply doing more.
• The value of travel—both near and far—in broadening empathy and perspective.
• Lessons from John McCain about honoring principles and bridging divides.
• The role of humility and how serving with it can reshape leadership.
• How listening deeply—not just hearing—creates space for meaningful change.
• Why legacy is less about control and more about the small, consistent actions we leave behind.

Three Connection Points

• Neil’s book: Do More Good
• 5 Steps Anyone Can Take to “Do More Good” and Make a Lasting Impact | Success Magazine
• Your Time is Not Thine: Rethinking “Know Thy Time”

Conversations like this remind me that productivity isn’t about output for its own sake—it’s about impact. Neil’s perspective reinforces the idea that empathy, humility, and legacy aren’t separate from our work, but central to it. I hope this episode leaves you inspired to do not just more, but more good.