What Would Dave Do?

Tim Winner

59 episodes listed below

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Purpose, told through lived experience.

The gist

What Would Dave Do? follows reflective conversations with people working through business, art, therapy, finance, public life, and clearer direction. The tone is loose and human, with plainspoken stories leading into practical lessons about success, service, family, money, and personal direction.

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About What Would Dave Do?

What Would Dave Do? is a warm, interview-led show built around the search for a person’s why. It is not polished into tight lessons. That looseness is part of its character, because guests are allowed to circle a memory, correct themselves, and find the point in real time. The conversations often begin with ambition. They usually end somewhere more personal. JB Gossinger talks about systems for high achievers and the difference between money and peace. Todd Malloy brings the discussion toward burnout, responsibility, corporate life, and the work of helping people understand themselves. Senator Bob Packwood turns a political career into a conversation about relationships, preparation, and how power actually moves through institutions. Bo Turner explains Bitcoin mining through money, energy, computing, and the gap between nodding along and actually understanding a system. Scott Harris uses New York City real estate to talk about homeownership as emotion, identity, and long-term wealth. Robert D. Laurentis brings aviation, danger, service, and youth exposure into the same story. Joey Muray challenges familiar assumptions about debt, car payments, Wall Street, and financial freedom. Tim Packard’s episode follows a former police officer who risked comfort for art, then built a life around helping other artists sell their work. The show is broad by design. Business, finance, therapy, politics, art, and adventure all become ways to ask the same question. What did this person choose? What did it cost? What did it teach them? The tone stays friendly and curious, with short affirmations keeping the guest moving. It suits listeners who like practical wisdom delivered through lived experience rather than tidy lectures. The strongest episodes feel like a good long conversation after the headline has faded and the real story starts.

Made for: For listeners drawn to reflective interviews with people in business, public life, creative work, therapy, finance, and people who have changed direction. It suits anyone who likes practical life lessons carried by personal stories.

What sets it apart: The show’s strength is its plainspoken curiosity: guests are not squeezed into a niche, but invited to connect work, money, risk, service, and identity. The result feels more like a thoughtful conversation than a packaged business lesson.

In their own words

In memory of my best friend—whose life was tragically cut short—I created this podcast to carry his spirit forward. He had a rare gift: he saw people deeply, asked thoughtful questions, and lived with quiet conviction. What began as a tribute has grown into something much more. Now three seasons and over 55 episodes in, this podcast has become a space for meaningful conversations—an invitation to pause, reflect, and reconnect with what truly matters. Through stories from people of all walks of life, we explore how we grow through challenge, find purpose in the everyday, and stay grounded in aut...

As heard by us

Based on 5 episodes we listened to · September 2026

Guest conversations connect financial independence, career changes, operating systems, and institutional relationships to the motives behind consequential decisions.

What Would Dave Do? follows consequential choices back to the motives and working systems underneath them, using guest-led conversations and an openly curious host.

Read our full review in PlayNext →

Why you'd press play

A polar emergency meets pension-cashing reinvention, then hands you the bigger life questions.

Press play if you want

  • to hear power explained through relationships by someone who spent decades inside the Senate
  • a creative-career leap with the pension cash-out, the sales, and a giant painting on public transit
Read the full recommendation in PlayNext →
purpose and personal motivationbusiness systemsfinancial independence and debtreal estate and homeownershippublic service and political historyburnout and responsibilitycreative risk and art careersaviation, service, and youth exposure

Talks about

Best episodes of What Would Dave Do?

Short reviews from the PlayNext desk, based on the episodes we processed.

Beyond the Books: A Drunken Idea Turned Business EmpireApr 8, 2026

A grounded conversation about systems, purpose, and success beyond wealth.

This episode argues for a plain idea: high achievers usually need a system more than they need more motivation. JB Gossinger ties that point to Get It Done Now and keeps success framed in broader terms than money, bringing in work, peace, contribution, and even the choice to…

A Front Row Seat to History: Conversations with Senator Bob PackwoodFeb 17, 2026

A seasoned senator treats politics as relationship work, not performance.

Senator Bob Packwood comes across as a seasoned political operator, someone who understands how government works through access, pressure, strategy, and the plain value of relationships.

The Peace Pilot: Robert DeLaurentis Journey of Giving BackJan 7, 2026

A flight story that opens into service, exposure, and a broader mission.

Robert DeLaurentis is introduced with a clear sense of stakes: a North Pole flight, a burst jet fuel tank, chemical burns, fumes, watering eyes, and the choice to keep going because the mission mattered more than the discomfort. That gives the episode a firm center right away.

Financial Independence: The Secret to Living Life on Your TermsDec 19, 2025

A blunt, practical look at how debt can quietly keep freedom out of reach.

What Would Dave Do? frames a money conversation as a direct challenge to the usual script: work hard, climb the ladder, buy the things, and call it freedom.

Painting a New Path: Tim Packer's Leap from Law to ArtNov 26, 2025

A former police officer's shift into art becomes a clean story about value, conviction, and why people buy what they cannot leave behind.

Tim Packard is presented as a business-minded art seller whose story turns on value, risk, and the confidence it takes to stand behind original work.

Podcasts like What Would Dave Do?

Episodes

  1. 1

    Beyond the Books: A Drunken Idea Turned Business Empire

    Hidden gem

    Motivation is not the point.

    Apr 8, 2026·1h 3m·4 clips
  2. 2

    Will It Matter That You Lived? Lessons from Todd Malloy

    This episode features an interview with Todd Malloy, a psychotherapist and corporate consultant, discussing burnout, personal responsibility, and his journey from a challenging childhood to his current therapeutic work.

    Mar 31, 2026·1h 4m
  3. 3

    A Front Row Seat to History: Conversations with Senator Bob Packwood

    Hidden gem

    Senator Bob Packwood gets a warm welcome at home.

    Feb 17, 2026·1h 46m·5 clips
  4. 4

    How Bitcoin Redefines Economic Energy

    This episode explores how Bitcoin mining redefines economic energy through an interview with Bo Turner, founder of Abundant Minds, who discusses generating passive income and educating high net worth individuals about Bitcoin's deep technology and financial implications.

    Jan 29, 2026·1h 4m
  5. 5

    The Emotional Journey of Homeownership: Beyond the Transaction

    This episode features an interview with Scott Harris, a New York City broker and author, discussing the emotional and financial aspects of homeownership, including his experiences selling luxury properties in Manhattan.

    Jan 23, 2026·1h 4m
  6. 6

    The Peace Pilot: Robert DeLaurentis Journey of Giving Back

    Hidden gem

    Robert D.

    Jan 7, 2026·59m·2 clips
  7. 7

    Financial Independence: The Secret to Living Life on Your Terms

    Hidden gem

    What Would Dave Do?

    Dec 19, 2025·1h 3m·2 clips
  8. 8

    Painting a New Path: Tim Packer's Leap from Law to Art

    Hidden gem

    The host opens by framing Tim Packard as a former Toronto police officer who left the badge for art.

    Nov 26, 2025·1h 7m·2 clips
  9. 9

    Generosity in Action: Beyond Just Giving

    Nov 19, 2025·1h 3m
  10. 10

    The Magic of the Universe: Lessons from a Transformative Journey

    Nov 12, 2025·1h 9m
  11. 11

    Empowering Women: From Operations to Leadership

    Nov 5, 2025·1h 7m
  12. 12

    Unlocking Family Legacies with Autograph: A Digital Revolution

    Oct 29, 2025·1h 6m
  13. 13

    From Poverty to Paintings: Kevin Murphy's Inspirational Story

    Oct 22, 2025·1h 4m
  14. 14

    Connecting through Conversations: The Art of Podcasting

    Oct 15, 2025·1h 6m
  15. 15

    God's Hand in Grief: Marcia Earhart's Testimony

    Oct 9, 2025·1h 2m
  16. 16

    Rediscovering Critical Thinking in the Age of Misinformation

    Oct 2, 2025·1h 8m
  17. 17

    Movie Magic: The Love for Film That Defined an Era

    Sep 10, 2025·1h 3m
  18. 18

    The Power of Human-Centric Sales: Insights from Kayvon Kay

    Sep 3, 2025·1h 12m
  19. 19

    Redbird: Turning Grief into Inspiration

    Aug 27, 2025·58m
  20. 20

    From Marine to Mindset Mentor: The Journey of Andrew Wittman

    Aug 20, 2025·1h 2m
  21. 21

    From Classroom to Bullring: Dave Munson's Leather Legacy

    Aug 13, 2025·1h 9m
  22. 22

    What happens when digital fluency outpaces human connection?

    Jul 30, 2025·52m
  23. 23

    From the OR to the Boardroom — Dr. Carla Fowler’s journey is anything but ordinary

    Jul 23, 2025·1h 3m
  24. 24

    Engineering Change: Creating Better Workplaces with Brett Hoogeveen

    Jul 16, 2025·1h 12m
  25. 25

    Creating Opportunities Through Belief and Encouragement

    Jul 10, 2025·1h 5m
  26. 26

    Crazy Epic Courage: The Story of a Movement

    Jul 2, 2025·1h 31m
  27. 27

    Aspasia: Inspired by Ancient Wisdom, Designed for Modern Solutions

    Jun 24, 2025·1h 5m
  28. 28

    Paradise Lost, Purpose Found

    Jun 10, 2025·1h 1m
  29. 29

    Unleashing Creativity: AI's Role in Storytelling

    Apr 10, 2025·1h 5m
  30. 30

    Beyond the Catch: Transformation in Business and Life

    Apr 3, 2025·1h 7m
  31. 31

    Udo's Choice: A Journey of Self-Healing and Dedication Towards Better Health

    Dec 27, 2024·1h 18m
  32. 32

    Leading a Life of Blind Ambition: An Interview with Chad E. Foster

    This episode features an interview with Chad E.

    Nov 27, 2024·1h 1m
  33. 33

    From Radio Waves to Rock Schools: Matt Ross's Journey

    Oct 1, 2024·1h 2m
  34. 34

    Behind the Lens: Eriksen Dickens Passion for Storytelling

    Jul 19, 2024·50m
  35. 35

    Changing the Narrative: David Kirshbaum on Sustainable Communication

    Jul 11, 2024·55m
  36. 36

    Investor Match AI: Revolutionizing Funding by Connecting the Right People at the Right Time

    Jun 18, 2024·1h 4m
  37. 37

    The HuProject: Transforming Leadership in the Imagination Age

    Apr 25, 2024·1h 1m
  38. 38

    Radious : Redefining the Future of Workspaces

    Apr 11, 2024·1h 4m
  39. 39

    The Fascinating World of Value Storage and Gold: A Conversation with Dr. Adam Trexler

    This episode features an interview with Dr.

    Mar 7, 2024·1h 5m
  40. 40

    Alignment: The Key to Successful Leadership

    Feb 29, 2024·1h 5m
  41. 41

    Leadership in the Unknown: A Conversation with Leon Anderson

    Host Tim Winter interviews Leon Anderson, president of Instrument Agency, about his unconventional career path from acting to leadership, starting with how he got a job at Metal Toad while filming a commercial.

    Feb 9, 2024·1h 6m
  42. 42

    Robots and Retail: A Conversation with Ben Rigsby

    Host Tim Winter interviews Ben Rigsby about his work with robots and self-interactive kiosks in retail, exploring leadership and technological innovation.

    Dec 4, 2023·1h 16m
  43. 43

    The Power of Embracing Insecurities: A Conversation with Jay Martin Jr.

    This episode features an interview with Jay Martin Jr.

    Nov 28, 2023·1h 7m
  44. 44

    The Power of Being Intentional: Insights from Michael Ulwelling

    Sep 28, 2023·1h 13m
  45. 45

    Avery Roth

    Sep 21, 2023·1h 21m
  46. 46

    Connor Quinn

    Aug 24, 2023·1h 14m
  47. 47

    Jennifer Barker

    Aug 1, 2023·37m
  48. 48

    Michael Allosso

    Jul 13, 2023·41m
  49. 49

    Ann Smith

    Jun 29, 2023·1h 2m
  50. 50

    Larry Plotnick

    Jun 23, 2023·1h 12m
  51. 51

    Reggie Wideman

    May 30, 2023·1h 9m
  52. 52

    Rick Mulinix

    May 26, 2023·1h 3m
  53. 53

    John Sanders

    Apr 28, 2023·1h 1m
  54. 54

    Scott Roth

    Apr 20, 2023·1h 1m
  55. 55

    Thomas Cox

    Apr 6, 2023·1h 13m
  56. 56

    John Scales

    Mar 30, 2023·1h 13m
  57. 57

    Suzanne Johnson

    Mar 20, 2023·58m
  58. 58

    Hayli Hay

    Mar 5, 2023·40m
  59. 59

    John Alderson

    Feb 21, 2023·1h 3m