• 7 minutes 10 seconds
    Work Like a Lion: Productivity for an ADD Brain

    In this episode, I talk about working like a lion as a better productivity model for an ADD-style brain.

    Instead of trying to graze all day, the idea is to rest deeply, work in intense bursts, use habits and rules to carry the work, and shorten the distance between idea and execution.

    This is a practical way to think about focus, momentum, scheduling, and founder energy.

    19 August 2026, 6:39 pm
  • 5 minutes 40 seconds
    Stop Doomscrolling: Trade Up to Better Media

    Trade Up Your Media: Stop Infotainment & Read for Real Change

    The speaker discusses feeling unsatisfied by scrolling and "infotainment," which blurs information and entertainment and scatters attention with addictive but unfulfilling content. They propose a "trading up" process: choosing higher-quality media and, when possible, moving from digital to physical formats (e.g., newsletter to book, YouTube video to film or documentary, lower-quality authors to higher-quality ones) to be more engaged rather than passive. They argue that despite easy access to great minds like Einstein and Seneca, shared enlightenment is limited because consumption doesn't translate into transformation. Citing Tim Ferriss on declining book sales since ChatGPT and Derek Sivers on life-changing sentences found deep in books, they emphasize that real change requires focus, effort, and presence, and note that reading physical material reduces the willpower drain of digital distractions.

    00:00 Doomscrolling Dissatisfaction

    01:10 Infotainment and Attention

    01:36 Trading Up Your Media

    02:32 From Information to Transformation

    02:56 AI and the Collapsing Info Market

    03:35 Life Changing Ideas Need Depth

    04:10 Printing Podcasts to Focus

    04:33 Physical vs Digital Reading

    05:28 Choose Better Inputs


    #DeepWork #Focus #MediaDiet

    18 August 2026, 6:48 pm
  • 5 minutes
    How to Embrace Change and New Opportunities

    AI, Change, and Opportunity: How to Adapt Without Doing It Alone

    David discusses how constant change in the world creates new opportunities, even when it feels scary and demands adaptation. He notes that every day brings new businesses, books, apps, and tools, and that technological advancement often drives deflation-making once-expensive products smaller, cheaper, and more powerful-while also disrupting older industries. He frames AI as an accelerating force that will change jobs and behaviors, but emphasizes that focusing only on disruption misses the expanding set of new doors opening through innovation, culture, and improved tools. He highlights the interdependent nature of the economy-companies exist because someone started them and because customer demand evolves-and concludes that while change isn't entirely on your shoulders to create, benefiting from it requires choosing to participate.

    00:00 Welcome and Big Change

    00:23 Daily World Shifts

    00:54 Riding the River

    01:49 Tech Gets Cheaper

    02:36 Disruption and AI Fears

    03:09 New Doors Opening

    03:44 Interdependent Economy

    04:23 Your Role to Participate


    #AI #ChangeManagement #Entrepreneurship

    11 August 2026, 6:47 pm
  • 7 minutes 24 seconds
    Transforming Goals into Changes and Habits

    David Sherry explains why goal-setting often fails for entrepreneurs and how to fix it. He argues that many people set "fake" goals based on what they think they should want or what others are doing, which leads to low commitment and stalled progress; he recommends getting honest about what you truly want so you have sustainable energy to pursue it. He also warns that big, vague goals (like making a million dollars) lack actionable information and can create frustration. Instead, he suggests reframing goals around specific changes and transformations-who you want to become and what you need to do today-by focusing on habits, systems, and concrete shifts from point A to point B in business and life.

    00:00 Why Goals Fail

    01:01 Spotting Fake Goals

    02:11 Make Goals Authentic

    03:13 Goals Aren't The End

    04:02 Focus On Change

    04:54 Turn Goals Actionable

    05:56 Systems And Habits

    06:55 Becoming Who You Want

    07:20 Closing Thoughts


    #GoalSetting #Habits #Entrepreneurship

    5 August 2026, 6:46 pm
  • 6 minutes 45 seconds
    How to Stop the Entrepreneur Roller Coaster

    This video explains why entrepreneurship often feels like an emotional roller coaster, with highs and lows driven not just by business problems but by how founders relate to them. As businesses grow, more people and more problems appear, much of which is outside the entrepreneur's control, and fear about potential issues can amplify the stress. The core issue is tying personal identity entirely to the company, causing mood to rise and fall with perceived business performance. The speaker suggests the way out is recognizing you exist outside the business and building a diversified identity through hobbies, friends, travel, and interests beyond work. This creates emotional balance and can also improve decision-making by reducing over-attachment and increasing objectivity.


    00:00 Entrepreneurship Roller Coaster

    00:56 Why It Feels Unstable

    01:50 Identity Fuels The Swings

    03:07 You Are Not Your Business

    05:02 Build A Life Outside Work

    05:37 Objectivity And Better Decisions

    06:06 Diversify Your Identity

    06:36 Closing And Next Videos


    #FounderMindset #Entrepreneurship #BusinessGrowth

    29 July 2026, 6:45 pm
  • 9 minutes 3 seconds
    It's Not Burnout (You're Reinventing Your Identity)

    What many people call burnout is often deeper misalignment: as you change over time, your current job, relationship, hobby, or identity may stop feeling resonant, leading to boredom, masking your true feelings, and a growing tension between how you feel and the story you've held about yourself. The speaker describes this as a metamorphosis process where withdrawing, coasting, and conserving energy can be a normal part of detaching from an old identity, even though it can bring shame and uncertainty about what comes next. They share personal experience leaving a founder/CEO role and taking long walks to create space, and note they're currently shifting toward an investor mindset. The suggested path forward is to use language and daily actions to try on and build connection to the new identity step by step, recognizing that much growth happens beneath the surface.


    00:00 Burnout vs Misalignment

    01:03 When Excitement Fades

    02:07 Masking the Inner Clash

    03:39 Metamorphosis and Withdrawal

    05:26 Space for the Unknown

    05:56 Growth Beneath the Surface

    06:45 Try On a New Identity

    07:37 Speak It Into Reality

    08:14 Evolving Step by Step

    08:55 Closing and Next Steps


    #FounderMindset #Burnout #IdentityShift

    21 July 2026, 6:44 pm
  • 7 minutes 8 seconds
    You Don't Want Freedom (Here's What You Actually Want)

    Many founders wrongly chase "freedom," entrepreneurship can reduce freedom as success grows and that a life with no responsibilities can lead to depression; instead, real freedom is choosing which responsibilities to take on. To build alignment, they recommend reflect on meetings and activities, tracking how they felt, and using the past to plan the future by pursuing what consistently brings joy and excitement.00:00 Morning Reflection Habit00:39 The Freedom Myth01:57 Choosing Responsibilities03:17 Alignment Creates Luck04:30 Feelings Over Intellect04:57 Scorecards for Alignment05:55 Build a Sustainable Career06:59 Closing and Next Steps#FounderMindset #Entrepreneurship #SelfEmployment

    14 July 2026, 6:43 pm
  • 34 minutes 26 seconds
    "What if the thing that has 'nothing to do with anything' is the fuel for you and your business?"

    In this Hidden Value session, Tanya Moushi and I explore the themes of creativity, freedom, and the complexities of personal and professional responsibilities. Tanya shares her struggles with creative paralysis and the desire to compose music, while I encourage her to prioritize her desires and define what freedom means to her. We discuss the importance of intentional planning, the weight of familial expectations, and the need for open dialogue about responsibilities and guilt. Ultimately, the conversation emphasizes the significance of creating space for personal fulfillment within the framework of a business.

    11 December 2025, 12:00 pm
  • 27 minutes 27 seconds
    “Do I grow this business, or will that cost me my freedom?”

    Andrew Fink left a stable career in management consulting to build a solo writing practice helping founders turn their ideas into newsletters, LinkedIn content, and now even books. His business is working. He makes a good living, has freedom to travel, train for races, and design his days. But lately, he’s been wrestling with a big question: should he grow this into an agency for more financial upside, and if so, what does that cost him?

    In this conversation, we uncover the tension beneath that question: the pull toward growth and challenge on one side, and the desire to protect freedom, flexibility, and a life he actually enjoys on the other. Together, we explore how to move beyond rigid either/or thinking and into reversible experiments that generate real information instead of endless planning.

    Because whether you’re a founder, consultant, or creator, most big business decisions don’t get solved by more thinking. They get solved by taking the next small step, seeing how it feels, and letting that experience guide what comes next.

    13 November 2025, 12:00 pm
  • 27 minutes 15 seconds
    "I help founders tell their story, so why am I struggling to tell my own?"

    Mohammad Khan helps deep tech founders make their complex ideas understandable and compelling. But lately, he’s been facing the same challenge he solves for others: how to articulate the unique value of his own work. When AI can write copy and marketing teams can polish messaging, where does his kind of storytelling fit?

    In this conversation, Mohammad and David uncover the real tension beneath that question: the difference between marketing a company and marketing the founder behind it. Together, they explore how the recognition and visibility comes from the story only you can tell.

    Because whether you’re a founder, creator, or consultant, the hardest story to tell is often your own. But that’s where your unique value lives.

    6 November 2025, 12:00 pm
  • 22 minutes 50 seconds
    "I helped build products at scale, so why does smaller suddenly feel bigger?"

    In this episode, I sit down with Cris Valerio, a former journalist turned tech innovator, as she shares her career journey from the newsrooms of New York City to the tech scene of Silicon Valley. Cris opens up about her midlife transition into entrepreneurship, driven by a desire to create meaningful impact beyond the corporate ladder. We explore how she's redefining success by focusing on relational impact and Main Street business ventures. We uncover how Cris is leveraging her experiences to build a legacy that truly resonates with her values.

    30 October 2025, 11:00 am
  • More Episodes? Get the App