• The Secret to Authentic Connections (For People Who Hate Networking!)
    May 14 2026

    In This Episode of Business Lunch: We dive into the world of networking, something that many dread but is crucial for business success. They discuss the difference between transactional and relational networking, the importance of curiosity, and how to build genuine connections without feeling forced or awkward. You'll hear real-life examples of what works, what doesn’t, and how even self-proclaimed introverts can become great networkers by leading with curiosity and kindness.

    Chapters:

    00:45 — Why Most People Hate Networking

    03:55 — Transactional vs. Relational Networking

    07:05 — Curiosity Over Strategy

    09:30 — Networking for Introverts

    12:45 — Creating Opportunities for Others

    16:00 — The Power of Being Generous

    19:15 — Building a Trustworthy Network

    22:30 — Leveraging Super Connectors

    27:15 — Final Thoughts: Becoming a Great Networker

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    Resources:

    7 Steps to Scalable workbook

    Get my book, Zero Down, FREE

    Mentioned in this episode:

    Build Your CEO Dashboard

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    28 mins
  • Building an AI Chief of Staff with Obsidian and Claude Code
    May 12 2026

    In This Episode of Business Lunch: We discuss how to transform note-taking apps into AI-powered chief of staff systems that manage daily operations, leveraging architectural insights and local data storage for security and efficiency.

    Chapters:

    00:00 Introduction to AI as a Chief of Staff

    00:29 The Limitations of Current AI Tools

    01:25 Architectural Insights and the Obsidian System

    02:14 Building a Memory-Enabled AI System

    03:13 Why Plain Text Markdown Matters

    04:34 The Web of Interconnected Notes

    06:03 Traversing the Knowledge Network

    07:00 Simulating a Human Chief of Staff

    08:27 Automating System Setup with a Single Prompt

    09:22 Ensuring Transparent and Permanent Memory

    11:45 From Thinking to Acting: Automating Operations

    12:12 Command Line Interface and External Tools

    14:30 Remote Control and Autonomous Agents

    15:01 Security Risks of Fully Autonomous AI

    16:29 Mitigating Prompt Injection Attacks

    18:26 Balancing Capability and Security

    19:23 Reflections on AI and Business Management

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    Resources:

    7 Steps to Scalable workbook

    Get my book, Zero Down, FREE

    Mentioned in this episode:

    Build Your CEO Dashboard

    Get one report every week of the key metrics you need to know with the CEO Dashboard!

    CEO Dashboard

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    21 mins
  • Building Collaboration and Ownership
    May 7 2026

    In This Episode of Business Lunch: We get into the importance of shared goals and alignment in achieving success, whether in business relationships or personal interactions. Join us as we explore strategies for fostering collaboration, owning mistakes, and reframing conflicts towards mutually beneficial outcomes.

    Chapters:

    00:00 - Matt's Dramatic Exit

    00:49 - Post-Integration Challenges

    03:15 - Mindset in Communication

    05:39 - Owning Mistakes and Finding Solutions

    08:02 - Establishing Clear Shared Goals

    09:58 - Addressing Goals and Misalignment

    10:26 - Unachievable Goals and Finger Pointing

    14:29 - Effective Communication Strategies

    16:50 - Collaborative vs. Combative Mindset

    24:02 - Embracing Collaboration

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    Resources:

    7 Steps to Scalable workbook

    Get my book, Zero Down, FREE

    Mentioned in this episode:

    Build Your CEO Dashboard

    Get one report every week of the key metrics you need to know with the CEO Dashboard!

    CEO Dashboard

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    26 mins
  • Getting Off The Org Chart, Part 2: How to Exit the Day-to-Day and Still Control Your Business
    Apr 30 2026

    In This Episode of Business Lunch: We explore how business owners can effectively exit the org chart while maintaining control and generating revenue. Topics include compensation strategies, onboarding processes, and structuring deals with profits-only interests and phantom equity.

    Chapters:

    00:00 Introduction to Exiting the Org Chart

    02:57 Understanding Compensation for New Roles

    05:45 The Importance of Role Clarity

    08:59 Navigating the Hiring Process

    11:59 Strategies for Exit Readiness

    14:55 Compensation Structures and Considerations

    18:07 Exploring Synthetic Equity Options

    27:53 Establishing Value and Compensation Structures

    30:02 Understanding Profits Interest and Phantom Equity

    32:49 Navigating Executive Compensation Negotiations

    37:54 Onboarding and Transitioning New Leadership

    47:59 Redefining Roles and Business Identity

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    1. TikTok: Check out my TikTok Here
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    5. Subscribe to my YouTube 👉 Here

    Resources:

    7 Steps to Scalable workbook

    Get my book, Zero Down, FREE

    Mentioned in this episode:

    Build Your CEO Dashboard

    Get one report every week of the key metrics you need to know with the CEO Dashboard!

    CEO Dashboard

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    52 mins
  • The $10M Exit Mistake Most Founders Make
    Apr 28 2026

    In This Episode of Business Lunch: The conversation breaks down why most founders lose millions when selling their business, not because of poor performance but because they misunderstand how buyers think. It highlights that valuation at exit is driven less by growth and more by the removal of risk and uncertainty. The discussion walks through how buyers interpret financials, identify hidden risks, and use deal structure to protect themselves, ultimately showing that certainty and clean structure command premium outcomes.

    Chapters:

    00:00 The $10M Exit Mistake Most Founders Make

    01:24 Why Growth Hurts You at Exit

    02:24 How Buyers Think About Risk

    07:03 The Real Fight Happens in the Financials

    09:23 How EBITDA and Reserves Impact Valuation

    10:34 Why Working Capital Becomes Emotional

    12:52 Finding the Right Buyer with Urgency

    14:05 Controlling Buyer Psychology in the Data Room

    15:56 The Hidden Trap in Deal Structure

    18:01 Two $30M Deals, Completely Different Outcomes

    19:21 The Final Exit Playbook

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    Resources:

    7 Steps to Scalable workbook

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    21 mins
  • Getting Off The Org Chart: How to Hire a CEO Who Fits Your Next Chapter
    Apr 23 2026

    In This Episode of Business Lunch: We explore the critical process of getting off the org chart, hiring a CEO, and preparing your business for a successful exit. They discuss strategies, common pitfalls, and the importance of systems, culture, and right-fit leadership.

    Chapters:

    00:00 Introduction to Business Lunch and Topic Overview

    02:00 The Importance of Getting Off the Org Chart

    05:50 Defining 'Off the Org Chart' and Its Implications

    11:54 Common Mistakes in Transitioning Roles

    17:58 Preparing for the Transition and Identity Shift

    24:08 Steps to Successfully Exit the Org Chart

    26:13 Building a Self-Sustaining Business

    30:02 Defining the CEO Role

    37:00 Finding the Right CEO

    43:00 Vetting Candidates and Cultural Fit

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    Resources:

    7 Steps to Scalable workbook

    Get my book, Zero Down, FREE

    Mentioned in this episode:

    Build Your CEO Dashboard

    Get one report every week of the key metrics you need to know with the CEO Dashboard!

    CEO Dashboard

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    50 mins
  • Mastering Business Valuation: The Power of Quality of Earnings
    Apr 16 2026

    In This Episode of Business Lunch: We explore the critical factors that influence business valuation, focusing on Quality of Earnings (Q of E), recurring revenue, customer and channel diversity, and deal structures. They share actionable insights for entrepreneurs aiming to maximize their business value and prepare for successful exits.

    Chapters:

    00:00 Introduction and Personal Updates

    02:06 Understanding Quality of Earnings (Q of E)

    10:44 The Importance of Recurring Revenue

    15:45 Optimizing Quality of Earnings

    20:41 Customer and Channel Diversity

    25:29 Preparing for a Business Sale

    30:15 The Role of EBITDA and Growth Metrics

    35:37 Final Thoughts and Key Takeaways

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    Resources:

    7 Steps to Scalable workbook

    Get my book, Zero Down, FREE

    Mentioned in this episode:

    Build Your CEO Dashboard

    Get one report every week of the key metrics you need to know with the CEO Dashboard!

    CEO Dashboard

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    38 mins
  • The Morality of Mass Layoffs: What Business Leaders Need to Know
    Apr 9 2026

    In This Episode of Business Lunch: We explore the ethics and practicalities of layoffs, the importance of stewardship in business, and how to handle difficult decisions with empathy and professionalism. Roland Frasier and Ryan Deiss share insights from their experiences, emphasizing the importance of long-term thinking and human-centered leadership.

    Chapters:

    00:00 Introduction and Personal Anecdotes

    03:10 The Human Side of Business and Customer Relationships

    04:22 Innovations in Music Technology and Business Networking

    07:55 Discussion on Oracle's Layoffs and Business Morality

    09:58 Context and Morality of Business Decisions During Hard Times

    13:03 Stewardship and Responsibility in Business Leadership

    15:57 The Impact of Layoffs on Employees and Society

    20:12 Media Portrayal of Business and Leadership Attitudes

    22:59 Turning Adversity into Opportunity and Resilience

    27:55 Practical Approaches to Large-Scale Layoffs

    34:04 Effective Communication Strategies for Workforce Reductions

    35:45 Final Thoughts and Audience Engagement

    Connect with me on social:

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    5. Subscribe to my YouTube 👉 Here

    Resources:

    7 Steps to Scalable workbook

    Get my book, Zero Down, FREE

    Mentioned in this episode:

    Build Your CEO Dashboard

    Get one report every week of the key metrics you need to know with the CEO Dashboard!

    CEO Dashboard

    Show More Show Less
    38 mins