The Matt Chambers Show

Matt

The Matt Chambers Show explores global living, business, and long-term freedom through real operator experience — not theory or hype.Hosted by Matt Chambers, the show features long-form conversations with founders, operators, and investors who are building and running real businesses, deploying capital, and making high-stakes decisions.Conversations focus on how people actually think about business growth, money, risk, mobility, and long-term optionality — including what worked, what didn’t, and what they would do differently today. Topics span entrepreneurship, investing, international strategy, lifestyle design, and decision-making across borders.Matt brings a background in operating and relationship-driven sales, with deep international experience across Latin America and the U.S., allowing for grounded, commercially realistic conversations — not surface-level advice or startup hype.This show is a fit for guests who are interested in or are actively operating businesses, managing capital, or building platforms with real traction - and who value thoughtful, high signal conversations over promotional appearances.

  1. 21H AGO

    How To Think Like an Owner, Not an Operator

    In this engaging podcast, Matt Chambers and Craig Morningstar explore the journey of entrepreneurship, the importance of financial literacy, and the strategies for maximizing business value. They discuss the power of compound interest, the significance of succession planning, and the role of self-talk in achieving success. Craig shares insights on innovative business ideas and the impact of community support, emphasizing the need for entrepreneurs to navigate their financial houses intentionally. The conversation highlights the potential for wealth extraction and the importance of protecting business assets, ultimately guiding listeners towards a more efficient and profitable business model.Chapters00:00The Birth of a Podcast00:55Entrepreneurial Journeys and Financial Freedom02:43Understanding Compound Interest05:33Maximizing Business Value and Wealth Extraction08:18Business Valuation Insights11:14Drivers of Business Value13:43The Importance of Leadership and Delegation17:34Succession Planning and Future Generations29:39Transitioning Business Ownership32:09The Importance of Purpose in Retirement35:58Finding Passion After Business37:46Navigating Business Wealth45:08The Rudolph Factor in Business52:14Understanding Inventory Challenges in Small Businesses52:59The Impact of Microloans on Entrepreneurship54:20Building Entrepreneurial Communities55:33Insights from the Aviation Industry57:17The Evolution of Airline Business Models01:00:47The Importance of Intentional Financial Planning01:02:42The Power of Self-Talk in Business01:03:53Getting Started with Enterprise Sage01:06:05Unlocking Hidden Value in Businesses01:06:42Finding Value in Non-Glorious Businesses01:10:23Innovative Business Ideas and Opportunities01:13:36The Role of Entrepreneurs in Community Building

    1h 14m
  2. 1D AGO

    The 1031 Exchange Strategy Most Real Estate Investors Miss

    In this conversation, Matt Chambers and Dave Foster discuss various aspects of real estate investment, focusing on the 1031 exchange, its benefits, and strategies for leveraging it for growth. They explore the importance of financial literacy, the challenges of the real estate market, and the need for education in navigating investment opportunities. The discussion also touches on personal experiences in real estate, the significance of tax-free gains, and the evolution of their podcast and business initiatives.Key Takeaways:The 1031 exchange allows for tax deferral on real estate sales.Investors can leverage multiple properties through 1031 exchanges.Financial literacy is crucial for successful investing.Real estate offers various tax benefits compared to other investments.The importance of understanding FIRPTA for foreign investors.Transitioning investment properties can lead to tax-free gains.Fix and flip strategies require careful market timing.Education on real estate investment is lacking in traditional schooling.The 1031 Investor aims to educate and empower investors.Community and networking are vital in real estate investing.Sound Bites:"It's a game changer.""It's a fix-it-flippers dream.""It's not how much money you make."Chapters:00:00Introduction and Technical Glitches02:55Caribbean Shipper and Podcast Developments05:55Real Estate Investing and 1031 Exchanges08:41Leveraging 1031 Exchanges for Growth11:41Tax-Free Gains and Real Estate Strategies14:28Sailing Adventures and Community Living17:27Converting Investments into Primary Residences19:36Understanding 1031 Exchange Requirements22:01Navigating Foreign Investment and FIRPTA23:11Creative Financing in Real Estate25:46Long-Term Wealth Building through Real Estate27:35The Role of 1031 Investor in Education29:17The Need for Financial Literacy30:45Breaking Free from Traditional Education35:05The Tax Code as an Incentive36:36The Historical Context of 1031 Exchange40:12Connecting with 1031 Investor

    36 min
  3. 2D AGO

    How To Build a Successful Retirement

    In this conversation, Matt Chambers and Jesse Hurst discuss the intricacies of retirement planning, common financial mistakes, the importance of good financial habits, and the impact of living abroad on financial well-being. They emphasize the significance of understanding compound interest, maintaining discipline in investments, and the role of financial planning in achieving a successful retirement. The discussion also touches on the lifestyle benefits of living in different countries and how financial planning can lead to a more fulfilling life in retirement.TakeawaysMost clients seek help when transitioning to retirement.Common topics among retirees include health and travel.Many believe they need to be wealthy to start financial planning.Regret syndrome can hinder financial progress.Understanding where you are financially is crucial.Good financial habits lead to wealth accumulation.Investing requires discipline and a long-term perspective.People often panic during market downturns.Financial planning can provide freedom and confidence.A successful retirement is about enjoying life, not just money.Chapters00:00Introduction to Financial Planning and Retirement04:57Common Mistakes in Financial Planning10:33Investment Strategies for Retirement16:15The Long-Term Perspective on Investments21:56Poponomics: Insights from Pop Culture for Financial Success27:35Understanding Compound Interest34:58Defining a Successful Retirement39:49Living Abroad: A Different Perspective47:55The Future of Transportation and Financial Freedom

    51 min
  4. 12/16/2025

    Unlocking the Secrets of Multifamily Real Estate

    Send us a text In this conversation, Veena Jetti shares her journey from starting in single-family homes to building a billion-dollar multifamily real estate portfolio. She emphasizes the importance of education, networking, and partnerships in the real estate industry. Veena discusses the complexities of raising capital, the significance of understanding securities laws, and the benefits of investing in landlord-friendly markets. She also highlights the tax advantages of multifamily investments and the need for a strong team to navigate the challenges of the current market. Throughout the discussion, Veena provides valuable insights and practical advice for aspiring real estate investors. Chapters 00:00 Introduction and Background 02:48 Journey into Multifamily Investing 05:42 Raising Capital and Overcoming Misconceptions 09:22 Structuring Deals and Partnerships 13:29 Learning and Networking in Multifamily 17:07 Market Selection and Investment Strategies 28:47 Exploring Hot Real Estate Markets 30:36 The Importance of Job Diversity in Real Estate 32:19 Scaling Up: The Benefits of Larger Multifamily Deals 34:20 Tax Benefits of Multifamily Investments 36:04 Timing the Market: When to Invest in Multifamily 38:10 Understanding Financing in Multifamily Investments 40:00 Lessons Learned: Partnerships and Legal Considerations 42:41 Balancing Family Life and Business Success 44:32 Creating a Legacy in Real Estate 50:11 Outro Podcast.mp4 Support the show

    52 min
5
out of 5
3 Ratings

About

The Matt Chambers Show explores global living, business, and long-term freedom through real operator experience — not theory or hype.Hosted by Matt Chambers, the show features long-form conversations with founders, operators, and investors who are building and running real businesses, deploying capital, and making high-stakes decisions.Conversations focus on how people actually think about business growth, money, risk, mobility, and long-term optionality — including what worked, what didn’t, and what they would do differently today. Topics span entrepreneurship, investing, international strategy, lifestyle design, and decision-making across borders.Matt brings a background in operating and relationship-driven sales, with deep international experience across Latin America and the U.S., allowing for grounded, commercially realistic conversations — not surface-level advice or startup hype.This show is a fit for guests who are interested in or are actively operating businesses, managing capital, or building platforms with real traction - and who value thoughtful, high signal conversations over promotional appearances.