Episodes

  • S2:E25: Mastering Delegation and Category Design with Jaime and Sara
    Jun 23 2026

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    Summary:

    In this inspiring interview, Jaime and Sara share their remarkable journey from military service and homelessness to building a successful business focused on delegation and virtual assistance. Discover their insights on category design, leveraging AI, and creating a life of purpose and impact.

    Key Topics:

    • Jaime and Sara's journey from military to entrepreneurship
    • The concept of delegation intelligence and installing delegation departments
    • Category design and creating a new market category
    • Leveraging AI to enhance business operations
    • Overcoming challenges of homelessness and rebuilding life

    Chapters:

    1. 00:00 Introduction to Jaime and Sara Jay
    2. 01:50 Jaime's Military Journey and Transition to Civilian Life
    3. 05:25 Overcoming Homelessness and Finding Purpose
    4. 07:20 Sara's Perspective and Their Unique Meeting
    5. 10:14 Building a Life Together and Personal Growth
    6. 14:46 From Corporate to Entrepreneurship: Jaime’s Career Path
    7. 19:24 The Birth of Bottleneck and Its Mission
    8. 21:11 Understanding Delegation Intelligence and Its Importance
    9. 28:23 AI and the Future of Work: Embracing Change
    10. 32:01 Navigating Financial Responsibilities
    11. 34:02 Challenges in Business Ownership
    12. 39:44 Overcoming Obstacles and Embracing Change
    13. 46:36 The Importance of Delegation Intelligence
    14. 49:13 Final Thoughts and Recommendations

    Resources:

    Play Bigger by Christopher Lockhead
    Category Pirates by Christopher Lockhead
    Delegation IQ Platform







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    53 mins
  • S2:E24: Turning Collapse into Comeback: Lessons from Scott Lackey
    Jun 16 2026

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    Summary:

    Join us as Scott Lackey shares his remarkable journey from military service to entrepreneurship, including the lessons learned from failed inventions, the power of stewardship, and the importance of resilience. Discover how his experiences shaped his new book 'Wake Up to Die Again' and gain insights into turning setbacks into comebacks.

    Key Topics:

    • Military service and leadership lessons
    • Invention and innovation failures and successes
    • The concept of stewardship versus ownership
    • Resilience and overcoming setbacks
    • The story behind the book 'Wake Up to Die Again'

    Chapters:

    1. 00:00 Introduction to Scott Lackey: A Veteran's Journey
    2. 03:16 Military Service and Early Experiences
    3. 06:16 Transitioning to Civilian Life and Entrepreneurial Aspirations
    4. 08:58 The Birth of the Wire Dog Idea
    5. 11:47 College Life and Career Path
    6. 14:09 The Childhood Health Passport: A New Venture
    7. 19:20 Challenges and Lessons from the Business World
    8. 23:01 Stewardship vs. Ownership: A New Perspective
    9. 27:39 The Power of Response
    10. 28:21 Unpacking Trauma Through Writing
    11. 29:33 Facing Broken Promises
    12. 30:55 The Journey to Becoming an Author
    13. 32:49 Engaging with Readers
    14. 34:33 The Importance of Conversations
    15. 37:17 Advice for Veterans
    16. 38:40 Book Recommendations and Final Thoughts

    Action Items:

    • Reflect on your own stewardship in life and business.
    • Practice forgiving yourself for past mistakes.
    • Embrace resilience and small wins to achieve big goals.

    Resources:

    Scott Lackey's Website









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    43 mins
  • S2:E23: Strategic Transition: How Javier Guitron Built Wealth After Military Service
    Jun 9 2026

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    Summary:

    In this episode, Javier Guitron shares his unique journey from military service to successful real estate investing and risk management. He discusses the importance of strategic planning, continuous learning, and leveraging relationships to achieve financial independence and personal growth.

    Key Topics:

    • Military transition and career planning
    • Real estate investing and property management
    • Building relationships and leveraging networks

    Chapters:

    1. 00:00 Introduction to Javier Guitron
    2. 02:20 Javier's Military Journey and Transition
    3. 06:22 Real Estate Ventures and Lessons Learned
    4. 14:28 The Importance of Education and Skills
    5. 14:51 Catalyst for Real Estate Investment
    6. 21:23 Building Relationships and Mentorship in Real Estate
    7. 22:42 Unapologetic Authenticity
    8. 22:59 Lessons from Loss
    9. 23:45 Managing Properties and Life
    10. 23:45 Transitioning to Risk Management
    11. 23:51 Understanding 1099 vs W-2
    12. 26:10 Advice for Aspiring Entrepreneurs
    13. 27:46 Influential Voices in Business
    14. 30:04 Making Your Bed: A Personal Touch






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    32 mins
  • S2:E22: Overcoming Trauma: A Vietnam Veteran's Path to Peace
    Jun 2 2026

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    Summary:

    In this inspiring interview, Vietnam Marine Corps Veteran Keith Cole shares his journey from military service and trauma to healing through faith and self-discovery. Discover how Keith's story offers hope and practical steps for overcoming burnout and PTSD.

    Key Topics:

    • Keith Cole's military service and trauma
    • The impact of PTSD and burnout
    • Faith-based recovery and spiritual disciplines
    • The 12-week recovery program and book
    • The importance of seeking help and sharing stories

    Takeaways:

    • Admitting trauma and seeking help is a sign of strength.
    • Faith and prayer played a crucial role in Keith's healing.
    • Writing and sharing personal stories can help others heal.
    • A structured spiritual discipline can aid in recovery.
    • Hope and enthusiasm can be restored through faith and action.

    Chapters:

    1. 00:00 Introduction to Keith Cole: A Veteran's Journey
    2. 02:00 From Childhood Dreams to Military Service
    3. 03:43 Experiences in Vietnam: Combat and Trauma
    4. 07:34 Life After the Marines: Guardianship and New Beginnings
    5. 09:03 Transitioning to Civilian Life: Education and Career
    6. 13:20 Recognizing Burnout: The Path to Recovery
    7. 15:53 Finding Faith: A Turning Point in Healing
    8. 18:18 Writing the Book: Sharing the Journey
    9. 21:34 Ongoing Practices: Daily Habits for Recovery
    10. 23:42 Future Aspirations: Reaching Out and Helping Others

    Resources:

    Burnout, God's Recovery Plan (Book)
    Keith Cole's Website (Recovery by Faith)









    Support the show

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    28 mins
  • S2:E21: Recapping the Month of May and Military Appreciation Month
    May 26 2026

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    Summary:

    The MAY Recap episode explores the journeys of veterans transitioning into entrepreneurship, highlighting resources, success stories, and the ongoing mission to serve beyond military service. With insights from veteran entrepreneurs and program leaders, it emphasizes the importance of community, support, and strategic planning in turning dog tags into ownership.

    Key Topics:

    • Veteran entrepreneurship resources
    • Success stories of veteran entrepreneurs
    • Transition strategies from military to civilian business
    • Programs supporting veteran business owners

    Chapters:

    1. 00:00 Introduction to Dog Tags to Ownership
    2. 00:49 Reflecting on Military Appreciation Month
    3. 03:17 Transitioning from Service to Civilian Life
    4. 07:39 Spotlight on Veteran Entrepreneurs
    5. 11:51 The Journey of Bravery Bakehouse
    6. 16:40 Entrepreneurship Through Acquisition
    7. 21:37 Honoring Memorial Day and Its Significance

    Resources:

    Boots to Business
    DAV Patriot Bootcamp

    Syracuse University IVMF and J.P. Morgan Backed CEO Circle






    Support the show

    Visit our website: https://www.dogtags-to-ownership.com/

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    24 mins
  • S2:E20: How Veterans Are Building Businesses with J.P. Morgan-backed CEOcircle
    May 19 2026

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    Summary:

    In this episode, Army veterans and West Point graduates Daniel Gade and Terry Hill share their inspiring journeys from military service to entrepreneurship. They discuss resources like IVMF and JP Morgan's CEO Circle, the process of buying a business through acquisition, and the importance of community and mentorship for veteran business owners.

    Key Topics:

    • Veteran transition to entrepreneurship
    • Resources for veteran business owners
    • Entrepreneurship through acquisition (ETA)
    • JP Morgan's CEO Circle program
    • Building community and mentorship for veterans

    Chapters

    1. 00:00 Introduction to the Guests and Their Backgrounds
    2. 01:47 Military Journeys: From Service to Civilian Life
    3. 04:31 Transitioning to Corporate Roles: Terry's Experience at JP Morgan
    4. 07:14 Daniel's Transition: Resources and Challenges
    5. 09:15 Entrepreneurship Through Acquisition: Daniel's Journey
    6. 11:51 JP Morgan's Support for Veteran Entrepreneurs
    7. 15:07 Comparing Business Startups and Acquisitions
    8. 16:24 Initial Steps as CEO: Daniel's Approach
    9. 19:52 CEO Circle: Continuous Learning and Networking
    10. 21:18 Overview of CEO Circle Program and Its Benefits
    11. 24:20 Inspiration from Entrepreneurial Journeys
    12. 31:24 Embracing Entrepreneurship After Military Service
    13. 38:09 Building a Legacy Beyond Service
    14. 41:32 Book Recommendations and Final Thoughts

    Resources:

    • CEO Circle by IVMF and JP Morgan
    • Entrepreneurship through Acquisition (ETA)
    • Book: Turn the Ship Around by L. David Marquet
    • Book: Wounding Warriors by Daniel Gade










    Support the show

    Visit our website: https://www.dogtags-to-ownership.com/

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    44 mins
  • S2:E19: Scaling with Purpose: The Bravory Bakehouse story
    May 12 2026

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    Summary:

    Join us as we explore the inspiring journey of Nic and Erin Vandre, military veteran and spouse turned entrepreneurs, who founded Bravory BakeHouse. Discover their insights on purpose-driven business, overcoming challenges, and supporting the military community.

    Key Topics:

    • Military entrepreneurship journey
    • Purpose-driven business and community impact
    • Scaling and pivoting in small business

    Chapters:

    1. 00:00 Introduction to Bravory Bakehouse
    2. 01:53 Nic's Military Journey and Background
    3. 03:09 Erin's Experience as a Military Spouse
    4. 05:23 The Birth of Bravory Bakehouse
    5. 08:12 The Mission Behind Bravory Bakehouse
    6. 12:39 Challenges in Entrepreneurship
    7. 15:46 Scaling the Business
    8. 21:42 Lessons Learned in Business
    9. 22:20 The Weight of Leadership
    10. 24:14 Finding Purpose in Entrepreneurship
    11. 25:34 The Role of Education and Mentorship
    12. 27:46 Building Community and Collaboration
    13. 29:02 Advice for Aspiring Entrepreneurs
    14. 31:48 Creating Value and Purpose-Driven Profitability

    Resources:

    Bravory Bakehouse
    Dog Tag Incubator Program
    DAV Patriot Bootcamp







    Support the show

    Visit our website: https://www.dogtags-to-ownership.com/

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    37 mins
  • S2:E18: Building Legacy: How Rosella and Kenitra Scott Are Transforming Leadership and Business
    May 5 2026

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    Summary:

    In this episode, US Army retired Rosella and 1SG Kenitra Scott share their journey from military service to founding Legacy Vanguard Scott Group. They discuss transitioning out of the military, building a business, leadership development, and the importance of strategic hiring and organizational culture.

    Key Topics:

    • Military transition and retirement planning
    • Starting and scaling a veteran-led business
    • Leadership development and coaching
    • Strategic hiring and organizational culture

    Chapters

    1. 00:00: Introduction to Rosella and Kenitra Scott
    2. 02:08: Military Background and Transition to Civilian Life
    3. 05:22: Planning for Retirement and Business Ventures
    4. 08:57: Lessons Learned from Transitioning Out of the Military
    5. 11:09: The Spark for Starting Legacy Vanguard Scott Group
    6. 13:22: Overview of Legacy Vanguard Scott Group's Mission and Services
    7. 15:58: Hiring for Current Needs vs. Future Potential
    8. 17:29: Building a Business Together
    9. 19:15: Assessing Organizational Needs
    10. 21:29: Challenges in Business Development
    11. 22:39: Transitioning and Scaling the Business
    12. 24:03: The Entrepreneurial Mindset
    13. 26:37: Recommended Resources for Entrepreneurs

    Resources:

    • Boots to Business
    • score.org
    • H3 Leadership Book
    • Relentless by Tim Grove

    Guest Links:

    Rosella Scott

    Kenitra Scott


    Support the show

    Visit our website: https://www.dogtags-to-ownership.com/

    Follow us on Social Media

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    31 mins