The Most Mindset
Real conversations about mindset, mortgages, and mastery for loan officers and originators who have outgrown being undervalued and underpaid.
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011 Where the Obstacle Becomes the Advantage
12/22/2025
011 Where the Obstacle Becomes the Advantage
In this episode of the Most Mindset podcast, Michael Most interviews Bill Gross, a seasoned expert in probate real estate. Bill shares his unique journey from aspiring attorney to successful real estate agent, emphasizing the importance of understanding the probate process. He discusses the challenges and opportunities within the probate niche, the significance of building relationships, and the role of data in generating leads. Bill also highlights the importance of effective communication and the value of being an expert in court confirmation sales. The conversation concludes with insights on developing strong professional relationships and the mindset necessary for success in the real estate industry. 00:30 Introduction to Bill Gross and His Journey 02:59 Understanding Probate: A Deep Dive 05:55 Navigating the Probate Process 08:41 The Role of Professionals in Probate Real Estate 11:19 Data and Lead Generation in Probate 14:06 Real-Life Case Study: From Probate to Sale 16:48 Challenges and Success in Court Confirmation 19:36 Bill's Expertise and Track Record 22:37 Building Relationships in Real Estate 24:25 The Role of Loan Officers 26:18 Creating Value Through Professional Relationships 29:19 Networking and Community Building 33:08 Lessons from Communication and Conflict Resolution 35:50 Influential Books and Mindset
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010 Becoming the Trusted Advisor in a Noisy Market
12/15/2025
010 Becoming the Trusted Advisor in a Noisy Market
In this episode of The Most Mindset, Michael sits down with longtime friend Chris Ryder, the first real estate agent guest on the podcast, to unpack what actually drives success in today’s market. They talk about how a real friendship, not transactional, became a powerful partnership; why buyers often choose lenders for the wrong reasons; and how agents and loan officers can win by being the trusted advisor who communicates, protects the deal, and puts people first. Chris also shares his unusual path from theology into real estate, how he built his business like an entrepreneur, and the hard lessons from a flip, showing how trust, clarity, and execution matter more than any quote. 00:30 Introductions 06:55 Building Relationships in Real Estate 13:22 Chris Ryder's Journey into Real Estate 18:56 Starting a Real Estate Business 25:20 Navigating the Real Estate Market 28:04 The Humorous Side of Real Estate Transactions 33:45 Lessons from Flipping Properties 37:50 Mindset and the Role of a Trusted Advisor
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009 Building a Career With No Plan B
12/08/2025
009 Building a Career With No Plan B
In this episode, Michael Most interviews Aaron Tennison, a seasoned professional in the mortgage industry. They discuss Aaron's journey from a nomadic childhood in Alaska to his experiences in the Navy, and how these shaped his entrepreneurial spirit. Aaron shares insights into the challenges of the mortgage business, the importance of building relationships, and the lessons learned from his career. He reflects on influential books that have impacted his life and discusses his current success in a broker platform, emphasizing the value of adaptability and perseverance in a fluctuating industry. 00:30 Introduction to Aaron Tennyson 01:28 Aaron's Early Life and Aspirations 04:50 The Influence of the Navy on Aaron's Life 09:43 Navigating Stress in the Mortgage Industry 10:13 How Aaron Found His Way into Mortgages 16:34 Transitioning from Technician to Entrepreneur 18:58 Reflections on Market Opportunities 19:22 Influential Books and Life Lessons 20:22 Building Relationships in Business 23:07 Pride in Career Achievements 24:37 The Broker Platform Experience 27:22 Humorous Anecdotes from the Field 34:09 Final Thoughts and Reflections
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008 Communication Is Your Superpower
12/01/2025
008 Communication Is Your Superpower
In this episode of The Most Mindset, Michael sits down with longtime friend and veteran loan officer Chris Davis to unpack a 25-year journey through the mortgage world. From growing up in Napa’s wine country and backpacking the globe, to stumbling into tech sales and then landing in mortgage banking right as the “internet” was becoming a thing, Chris shares how communication, curiosity, and relationship skills shaped his career. Together they break down what it’s really like to move from big banks to IMBs to the broker model, the fears that come with those transitions, and the freedom on the other side. Chris talks about difficult clients, underwriting realities, staying calm when millions are on the line, and how mountain biking, family time, and perspective keep him grounded. It’s a real, relatable look at how to evolve, stay steady under pressure, and build a career you actually enjoy. 00:25 Introductions & Background 01:19 From Tech Sales to a New “Internet” Product 04:19 Backpacking the World & Early Career Detours 05:59 Wine, Marine Biology & Choosing a Different Path 07:36 The Power of Communication & Sales Skills 10:47 Big Bank Years & High-Rise Projects 16:27 More Products, More Guidelines, More Opportunity 21:02 Jumping to the Broker Model & Saying “Yes” More Often 25:52 Underwriting Reality Checks & Funny Client Moments 31:29 Becoming “Calm Chris” Through Perspective 39:34 Books That Shaped Chris & Final Thoughts
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007 From Big Banks to Broker Freedom
11/24/2025
007 From Big Banks to Broker Freedom
In this episode of the Most Mindset, Michael interviews Bob Hilsby, who shares his journey from a young entrepreneur in New York to a successful mortgage broker in California. Bob discusses his early career, the transition to the mortgage industry, and the lessons learned from owning a brokerage during the financial collapse. He reflects on his experiences in big banks, the challenges faced, and the importance of independence in the brokerage model. Bob also emphasizes the role of AI in enhancing business relationships and shares insights on maintaining personal well-being to support professional success. 00:30 Introduction and Background 03:22 Early Career and Entrepreneurial Spirit 06:19 Transition to Mortgage Industry 09:24 Brokerage Experience and Financial Insights 12:26 Navigating the Financial Collapse 15:17 Post-Collapse Career Moves 21:30 Transitioning from Douglas Elliman to Citibank 22:38 Challenges of Working in a Big Bank 26:57 Moving to Bank of America and New Opportunities 28:18 Desire for Independence in the Broker Space 29:41 Leveraging AI in Business Relationships 35:59 Finding Stability Through Consistency 37:50 Funny Story from the Field and Book Recommendations
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006 Networking is the Key to Sales Success
11/19/2025
006 Networking is the Key to Sales Success
In this episode of The Most Mindset, Michael Most interviews Ian Olsen, exploring his journey from a rugby player to a successful figure in the mortgage industry. Ian shares insights on the importance of relationships, the correlation between sports and business, and the transition to the broker model. He emphasizes the significance of curiosity in networking and the lessons learned over 25 years in the industry, including the importance of focusing on strengths and finding inspiration in personal growth. 00:30 Introduction to Ian Olson and His Journey 03:08 From Rugby to Trading: A Unique Path 05:37 The Correlation Between Sports and Business 08:28 Transitioning into the Mortgage Industry 10:56 Navigating the Mortgage Landscape 13:23 The Shift from IMB to Broker Model 15:57 The Benefits of the Broker Model 18:36 Finding Freedom in the Mortgage Business 20:35 Understanding Rate Trends and Bond Markets 25:16 Building Strong Relationships in Business 28:51 Merging Personal and Professional Networks 33:23 Influential Books and Personal Growth
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005 From Bartender to Mortgage Expert
11/07/2025
005 From Bartender to Mortgage Expert
In this episode of the Most Mindset podcast, Mike Yeates shares his journey from bartending to becoming a successful mortgage professional. He discusses the importance of work ethic, organizational skills, and building relationships in the industry. Mike reflects on his experiences transitioning between different business models, including independent mortgage banks and brokerages, and highlights the flexibility and options available in the broker model. He also shares humorous anecdotes and insights into the challenges of self-employment, the impact of technology on the mortgage industry, and the significance of maintaining honesty and consistency in client relationships. 00:00 Introduction and Background 02:20 Journey into the Mortgage Business 06:04 Organizational Skills and Work Ethic 10:58 Passion for the Mortgage Industry 13:50 Exploring Different Mortgage Models 19:14 Funny Stories and Industry Insights 22:58 Building Relationships in Business 24:19 Transitioning Between Models 26:10 Overcoming Culture Shock 29:00 Flexibility in the Broker Model 29:11 Nurturing Realtor Relationships 30:45 The Importance of Consistency 31:58 Old School Techniques in a Modern World 33:36 Pride in Longevity and Hard Work 37:21 The Impact of Technology on the Industry 39:26 The Value of Support Systems 42:37 Rejuvenation in the Right Environment
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004 Reputation is the Cornerstone of Business Success
11/03/2025
004 Reputation is the Cornerstone of Business Success
In today’s episode of The Most Mindset, host Michael Most talks with industry veteran David Jaffe about his journey from retail to becoming a top mortgage originator. David shares insights from more than three decades in the business—covering the mindset, habits, and lessons that helped him thrive through multiple market cycles. He discusses the books and mentors that shaped his growth, his transition from banks to the broker model, and how coaching helped him find balance and renewed passion for his work. Packed with wisdom, humor, and practical advice, this episode is a must-listen for anyone looking to build a lasting career in the mortgage industry. 01:06 Background and getting into mortgages 02:38 Retail beginnings and discovering real estate 05:12 First mortgage job and lessons learned 08:57 Mindset, motivation, confidence, and drive to succeed 10:53 Mentors, coaching, and impactful books 15:44 From banks to IMBs to Broker 17:58 Relationships, humility, and industry lessons 24:27 Moving to broker model and finding freedom 30:46 Coaching, work-life habits, and health routines 34:07 Industry highs, lows, and resilience 38:36 Reflections, gratitude, and closing remarks
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003 Navigating Today's Mortgage Landscape
11/03/2025
003 Navigating Today's Mortgage Landscape
In this episode of the Most Mindset, Michael Most interviews Kerry Ogata, who shares his unique journey into the mortgage industry, influenced by his wife and the COVID-19 pandemic. They discuss the importance of communication, the role of technology and AI in the industry, and the personal stories that make the work rewarding. Kerry emphasizes the need for adaptability in the evolving mortgage landscape and offers advice for newcomers, highlighting the significance of training and understanding client needs. The conversation also touches on the dynamics of working with family in the business and the future of mortgage brokering. 00:00 Introduction to Kerry Ogata's Journey 03:02 Transitioning from Tech to Mortgages 06:05 The Importance of Communication in Sales 08:51 Leveraging AI in the Mortgage Industry 11:50 Navigating Industry Challenges and Outages 15:04 Finding Purpose in Helping Clients 17:54 The Evolution of the Mortgage Industry 20:45 Advice for Newcomers in the Mortgage Business 23:48 The Human Element in Mortgage Transactions 26:45 The Benefits of Being a Mortgage Broker 29:50 Working Together as a Couple in the Industry
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002 From Design Dreams to Mortgage Success
11/03/2025
002 From Design Dreams to Mortgage Success
In this engaging conversation, Michael Most interviews Chris Pessy, exploring his journey from a design background to a successful career in the mortgage industry. They discuss the evolution of the industry, the importance of wellness and balance, and the role of AI in enhancing efficiency. Chris shares valuable insights on building authentic relationships, navigating market changes, and offers advice for newcomers in the field. The conversation highlights the significance of personal branding and the power of genuine connections in achieving success. 00:00 The Journey Begins: Chris Pessy's Background 02:56 From Design to Mortgages: A Career Shift 05:52 Lessons from the Industry: Navigating Challenges 08:38 The Importance of Balance: Wellness in Work 11:54 Riding the Waves: Industry Changes and Adaptation 14:47 Building Relationships: The Art of Connection 20:42 Navigating the Mortgage Industry in 2025 23:53 Embracing AI in Mortgage Solutions 29:30 Transitioning from Retail to Broker Models 33:47 Success Stories in Mortgage Financing 36:25 The Power of Personal Branding
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001 The Importance of Human Interaction
11/03/2025
001 The Importance of Human Interaction
In the inaugural episode of The Most Mindset, host Michael Most is a guest on the Mortgage Marketing Expert podcast with Phil Treadwell. Michael shares his journey from aspiring lawyer to successful mortgage broker, emphasizing the importance of understanding the 'why' behind processes and decisions in the mortgage industry. He discusses key traits for success, the significance of collaboration, and effective strategies for scaling a mortgage business. Michael also highlights the importance of having meaningful conversations with clients about their financial goals and navigating the current market dynamics. The episode concludes with a focus on building genuine relationships in the mortgage business. 00:00 Introduction to Michael Most's Journey 02:52 Key Traits for Success in Mortgage Origination 05:55 Understanding the Current Market Dynamics 08:47 The Importance of Collaboration in the Industry 12:07 Scaling Your Mortgage Business 14:54 Time Management and Knowing Your Worth 21:03 Navigating Market Conversations with Clients 22:14 Understanding Borrower Mindsets 25:38 Navigating Market Predictions 27:16 The Importance of Personal Connection 30:08 Building Relationships in Business 34:41 Competing in the Jumbo Loan Market 38:53 Overcoming Underwriting Challenges
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