Why Most DIY Investors Fail: Inside the Mind of a High-Conviction Value Investor | Oleg Litvinenko - E60
Thu Jul 31 2025
Oleg Litvinenko, a seasoned financial professional, founder of Meetinghouse Capital, and a firm believer in long-term, high-conviction equity strategies dives deep into the world of intelligent investing with Jesse and Gabe. With over two decades of experience managing portfolios, Oleg pulls back the curtain on how he identifies high-quality companies, evaluates leadership, and constructs a focused portfolio designed for enduring growth. He unpacks the difference between investing and speculation, explores the challenges individual investors face, and explains why his strategy offers a compelling alternative to index investing. Whether you're an aspiring investor or a seasoned wealth manager, this episode is a masterclass in thoughtful, principle-driven portfolio management.
Key Takeaways:
• What is Oleg’s process for identifying and evaluating high-quality companies for long-term investment?
• Why do individual investors often struggle with stock picking, and how does a concentrated strategy provide an advantage?
• How do leadership quality and competitive advantages shape the construction and performance of Oleg’s investment portfolio?
Key Timestamps:
(00:00) - Qualitative analysis and understanding business value
(05:00) - Identifying leadership quality and company longevity
(09:00) - Competitive advantages and dynamic moats
(10:00) - Reinvestment runways and value compounding
(11:00) - Portfolio construction and company concentration
(13:00) - Managing risk without over-diversifying
(14:00) - Challenges for DIY investors and Oleg’s edge
(16:00) - Aligning with long-term-oriented investors
(18:00) - Handling underperforming companies and turnarounds
(21:00) - Comparing active stock picking to index investing
(24:00) - Influences from Buffett, Munger, and value investors
(27:00) - Flexibility in geography and company size
Key Topics Discussed:
The Trusted Partner, Cobblestone Capital Advisors, Jesse Cramer, Gabe Chodak, Wealth Management Rochester NY, Financial Planning for Families, Fiduciary Financial Advisor, Comprehensive Financial Planning, Retirement Planning Advice, Tax-Efficient Investing, Risk Management for Investors, Generational Wealth Transfer Planning, Financial Strategies for High Earners, Personal Finance for Entrepreneurs, Behavioral Finance Insights, Asset Allocation Strategies, Advanced Estate Planning Techniques, Long-term investing strategy, Value-based portfolio management, Stock picking vs index funds, High-quality company analysis, Investment philosophy with Warren Buffett influence
Mentions:
Website: https://www.meetinghousecapital.com/
LinkedIn: https://www.linkedin.com/in/oleglitvinenko
Mentions: Markel Corporation
More of The Trusted Partner:
Website: https://cobblestonecap.com/the-trusted-partner-podcast/
Information presented in this podcast is not intended to be nor should be construed as individualized investment advice. All content is of a general nature and solely for educational, informational and illustrative purposes. Investments in securities are not insured, protected or guaranteed and may result in loss of income and/or principal. Opinions of unaffiliated third-parties may not represent those of Cobblestone Capital Advisors or its employees.
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Oleg Litvinenko, a seasoned financial professional, founder of Meetinghouse Capital, and a firm believer in long-term, high-conviction equity strategies dives deep into the world of intelligent investing with Jesse and Gabe. With over two decades of experience managing portfolios, Oleg pulls back the curtain on how he identifies high-quality companies, evaluates leadership, and constructs a focused portfolio designed for enduring growth. He unpacks the difference between investing and speculation, explores the challenges individual investors face, and explains why his strategy offers a compelling alternative to index investing. Whether you're an aspiring investor or a seasoned wealth manager, this episode is a masterclass in thoughtful, principle-driven portfolio management. Key Takeaways: • What is Oleg’s process for identifying and evaluating high-quality companies for long-term investment? • Why do individual investors often struggle with stock picking, and how does a concentrated strategy provide an advantage? • How do leadership quality and competitive advantages shape the construction and performance of Oleg’s investment portfolio? Key Timestamps: (00:00) - Qualitative analysis and understanding business value (05:00) - Identifying leadership quality and company longevity (09:00) - Competitive advantages and dynamic moats (10:00) - Reinvestment runways and value compounding (11:00) - Portfolio construction and company concentration (13:00) - Managing risk without over-diversifying (14:00) - Challenges for DIY investors and Oleg’s edge (16:00) - Aligning with long-term-oriented investors (18:00) - Handling underperforming companies and turnarounds (21:00) - Comparing active stock picking to index investing (24:00) - Influences from Buffett, Munger, and value investors (27:00) - Flexibility in geography and company size Key Topics Discussed: The Trusted Partner, Cobblestone Capital Advisors, Jesse Cramer, Gabe Chodak, Wealth Management Rochester NY, Financial Planning for Families, Fiduciary Financial Advisor, Comprehensive Financial Planning, Retirement Planning Advice, Tax-Efficient Investing, Risk Management for Investors, Generational Wealth Transfer Planning, Financial Strategies for High Earners, Personal Finance for Entrepreneurs, Behavioral Finance Insights, Asset Allocation Strategies, Advanced Estate Planning Techniques, Long-term investing strategy, Value-based portfolio management, Stock picking vs index funds, High-quality company analysis, Investment philosophy with Warren Buffett influence Mentions: Website: https://www.meetinghousecapital.com/ LinkedIn: https://www.linkedin.com/in/oleglitvinenko Mentions: Markel Corporation More of The Trusted Partner: Website: https://cobblestonecap.com/the-trusted-partner-podcast/ Information presented in this podcast is not intended to be nor should be construed as individualized investment advice. All content is of a general nature and solely for educational, informational and illustrative purposes. Investments in securities are not insured, protected or guaranteed and may result in loss of income and/or principal. Opinions of unaffiliated third-parties may not represent those of Cobblestone Capital Advisors or its employees.