The Trusted Partner Podcast - Wealth Strategies for High Net Worth Families

Cobblestone Capital Advisors
  • 3.8 (6)
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What does it take to make smarter financial decisions and secure your future? Welcome to The Trusted Partner, where Cobblestone Capital Advisors' Jesse Cramer and Gabe Chodak bring you engaging conversations with experts in financial planning, investment management, and wealth management. Designed to help you take control of your financial future, this podcast simplifies complex topics like tax-efficient investing, retirement planning strategies, and comprehensive financial planning. Whether you're navigating your growing career, preparing for retirement, or planning a lasting legacy, our expert guests provide practical advice tailored to real-world needs. Based in Rochester, NY, Jesse and Gabe combine their professional insights with relatable stories and actionable tips, helping you turn financial goals into achievable results. The Trusted Partner Podcast isn't just about managing money. It's about building confidence, securing peace of mind, and empowering you to make informed decisions for the long term. Tune in to The Trusted Partner Podcast and take the first step toward a smarter, brighter financial future.

  1. Why Most DIY Investors Fail: Inside the Mind of a High-Conviction Value Investor | Oleg Litvinenko - E60

    07/31/2025

    Why Most DIY Investors Fail: Inside the Mind of a High-Conviction Value Investor | Oleg Litvinenko - E60

    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.

    33 min
  2. DelMonte and CityGate: Rochester's Next Landmark Hotel - E59

    06/14/2025

    DelMonte and CityGate: Rochester's Next Landmark Hotel - E59

    Jesse and Gabe co-host an inspiring conversation with Alexander DelMonte, President and CEO of the DelMonte Hotel Group. As the third-generation leader of a company that's helped shape Rochester's hospitality landscape, Alex shares the remarkable origin story of his family's business, from a bold pitch to Bill Marriott to becoming Marriott's longest-continuous franchisee. But this episode isn't just about the past—it's also about building the future. Alex breaks down the vision behind the CityGate Hotel project, an ambitious new development that brings together local powerhouses: DelMonte Hotel Group, Pike Construction, Genesee Regional Bank, and Cobblestone Capital. You'll hear how dual-branding, smart site strategy, and Rochester's evolving market are converging to create a high-end hotel experience unlike anything the city has seen. Whether you're a seasoned investor, a local business leader, or just curious about how major deals come together, this episode delivers unique insight straight from the decision-makers' table. Tune in to hear how legacy meets innovation—right here in Rochester.   Key Takeaways: • How did the Del Monte Hotel Group grow from a single hotel into a nationally recognized hospitality company? • What makes the CityGate Hotel project a unique and promising investment opportunity in the Rochester market? • How do strategic partnerships and dual-branding enhance hotel development and long-term success?   Key Timestamps: (00:00) - Hotel franchising explained (06:30) - Choosing the right brand and property type (08:00) - Growth of the Del Monte portfolio (10:00) - Transition to higher-end, high-RevPAR markets (12:00) - The value of location and mixed-use developments (13:30) - Inside the CityGate project: planning and partnerships (15:00) - Why Rochester remains a strong hotel market (17:00) - Dual-branded hotels and operational synergies (20:00) -  Rochester firms collaborating on CityGate (22:00) - Construction timeline and project outlook   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 ,Rochester hotel development, CityGate Hotel project, Del Monte Hotel Group, Hotel investment opportunity, Dual-branded Marriott hotels   Mentions: Website: https://www.delmontehotels.com/  LinkedIn: https://www.linkedin.com/in/alexander-del-monte-00235a6    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.

    26 min
  3. Why Smart People Make Dumb Decisions - E58

    05/29/2025

    Why Smart People Make Dumb Decisions - E58

    Have you ever made a decision that seemed logical at the time, only to realize later that you were swayed by unseen forces? Cognitive biases shape the way we think, often without us even realizing it. In this episode, Jesse and Gabe take a deep dive into the fascinating world of cognitive biases—what they are, how they impact our decision-making, and most importantly, how to recognize and counteract them. Jesse and Gabe also explore real-life examples, psychological insights, and practical strategies to sharpen your thinking and make better choices in every aspect of life. Whether you're a leader, entrepreneur, or simply someone looking to improve critical thinking, this episode is packed with invaluable insights you won't want to miss!   Key Takeaways: • How do cognitive biases influence our decision-making processes in everyday life? • What strategies can individuals use to recognize and mitigate their own cognitive biases? • In what ways do cognitive biases impact society, particularly in areas like politics, business, and social interactions?   Key Timestamps: (00:00) - What Are Cognitive Biases? (07:40) - The Most Common Cognitive Biases (15:30) - How Cognitive Biases Affect Decision-Making (22:10) - The Science Behind Cognitive Biases (28:45) - Overcoming Cognitive Biases (35:20) - Case Studies & Real-World Scenarios   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, Cognitive Bias Examples, Psychology of Decision Making, How Bias Affects Thinking, Overcoming Cognitive Biases   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.

    40 min
  4. Why Business Leaders Must Have a Voice in Government | Marc Cohen - E57

    04/24/2025

    Why Business Leaders Must Have a Voice in Government | Marc Cohen - E57

    Jesse and Gabe sit down with Marc Cohen, Vice President of Government Affairs at O'Donnell and Associates, as they dive into the crucial role of advocacy in shaping the business landscape. With a career spanning from the Greater Rochester Chamber of Commerce to key government positions, Marc shares insider insights on how businesses—large and small—can ensure their voices are heard in legislative decisions. From local ordinances to federal regulations, Marc explains why advocacy isn't just an option—it's a necessity for business success. Oh, and stick around for a fun baseball-themed wrap-up, where Marc, Gabe, and Jesse share their favorite baseball memories! Learn how to ensure your business stays ahead in the ever-changing legislative landscape.   Key Takeaways: • What does a lobbyist really do? • How can business owners effectively engage with policymakers? • Is New York truly anti-business, or is there more to the story?   Key Timestamps: (00:00) - What Does a Lobbyist Do? (08:00) - The Need for Policy Representation (10:00) - Misconceptions About Government Decision-Making (12:00) - The Role of Lobbying (14:00) - Challenges in Government Relations for Businesses (16:00) - Importance of Building Relationships with Legislators (19:00) - New York's Business Climate (21:00) - Policy Issues Affecting Businesses (24:00) - Business Owners' Struggles with State Policies   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, Business Advocacy Services, Government Affairs Consulting, Small Business Legislation, Corporate Lobbying Strategies, Public Policy Impact on Business, Marc Cohen   Mentions: Website: https://odonnellsolutions.com/  LinkedIn: https://www.linkedin.com/in/marc-cohen-37a29524/    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.

    31 min
  5. The State of the World: Investing Amid Global Shifts | Jeff Kleintop - E56

    03/27/2025

    The State of the World: Investing Amid Global Shifts | Jeff Kleintop - E56

    This week, we're diving deep into the world of global finance with a truly special guest—Jeff Kleintop, Chief Global Investment Strategist at Charles Schwab. With a staggering $7 trillion in assets under management, Schwab's insights shape the financial landscape, and Jeff is at the helm of international market analysis. In this episode, Jeff unpacks the latest on tariffs, trade tensions, global economic trends, and market opportunities—including why Europe's "New Magnificent Seven" might be the next big thing. Plus, we tackle investor confidence, employment shifts, and the ever-changing role of the U.S. in global trade. Is international investing finally having its moment? Should you rethink your portfolio strategy? Tune in as we break it all down with Jeff's expert take! Listen now and get ahead of the market curve! Key Takeaways: • How are the proposed tariffs and global trade policies expected to impact international markets and supply chains? • What factors are influencing consumer confidence and employment trends in the U.S., and how might they affect the broader economy? • Why have international markets, particularly in Europe, been outperforming U.S. stocks, and what are the implications for investors?   Key Timestamps: (00:00) – The global market landscape (04:00) – European tariffs and their economic impact (06:00) – The real impact of tariffs (08:00) – International market uncertainty (09:00) – Germany's increased defense spending (12:00) – Rising US recession risks (14:00) – The effect of government spending cuts on GDP (18:00) – International stock outperformance (19:00) – The role of China and India in emerging markets (25:00) – Shipping, tariffs, and global politics (30:00) – New investment opportunities   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, Global investment strategies, International Stock Market Trends, Tariff Impact on the US Economy   Mentions: LinkedIn: https://www.linkedin.com/in/jeffrey-kleintop/   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.

    32 min
  6. Stock Options, RSUs, & Managing Concentration Risk | Allison Shuler - E55

    02/27/2025

    Stock Options, RSUs, & Managing Concentration Risk | Allison Shuler - E55

    Stock options. Restricted stock units (RSUs). They sound like Wall Street jargon, but if part of your paycheck comes in company stock, these terms could make—or break—your financial future. Join hosts Jesse Cramer and Gabe Chodak as they  dive into the world of equity compensation, with Certified Financial Planner (CFP), Allison Shuler. Together, they unravel the complexities of stock compensation, the tax implications you can't ignore, and the common mistakes that could leave thousands (or more!) on the table. Whether you're cashing in RSUs, exercising stock options, or navigating a high-stakes compensation package, this episode is your essential guide to making smarter financial moves. If you earn part of your paycheck in company equity, don't miss this one.   Key Takeaways: • Should you hold or sell your stock grants? • How does equity compensation impact your investment strategy? • What happens to your stock if you leave your company?   Key Timestamps: (00:00) - The rise of equity compensation: Why more employees are getting paid in stock. (03:00) - Stock Options vs. RSUs: Key differences and why they matter. (06:00) - How RSUs are taxed: The crucial moment when you owe the IRS. (08:00) - NSOs vs. ISOs: Which stock options come with better tax benefits? (11:00) - Common mistakes employees make with stock compensation. (13:00) - The risk of holding too much company stock: Why overexposure can be dangerous. (17:00) - The tax dilemma: Holding too long vs. selling too soon. (23:00) - How to create a strategy for selling stock and reducing risk. (26:00) - The hidden risks of equity-heavy compensation packages. (28:00) - Why you need an accountant and financial planner to optimize your strategy.   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, stock options, RSUs, equity compensation, taxes, compensation income, capital gains, financial plan, investment, diversify, NSOs, ISOs, Allison Shuler   Mentions: Allison's LinkedIn: https://www.linkedin.com/in/allison-schraf-shuler-cfp®-003870119    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.

    33 min
  7. Cobblestone's Best Thinking on 2025 | John DiPasquale - E54

    01/30/2025

    Cobblestone's Best Thinking on 2025 | John DiPasquale - E54

    John DiPasquale, managing partner at Cobblestone Capital Advisors reflects on his 26 years with the firm, discussing its evolution from a small team to a mid-sized business with a strong focus on client satisfaction and sustainable growth. The conversation transitions into a discussion on macroeconomic factors, the importance of setting realistic market expectations, and the role of goals-based investing. John also highlights future plans, including new private investment opportunities, and shares personal insights on his passion for the industry and the relationships he and the team have built with clients over the years. The episode reviews the key highlights of 2024 and shares the firm's outlook for 2025.   Key Takeaways: • How has Cobblestone evolved over the years, and what role do client relationships and referrals play in the firm's growth? • How does Cobblestone approach market predictions, and how does the firm integrate goals-based investing into their wealth management strategy? • What are Cobblestone's strategies for addressing client concerns related to economic uncertainties, and what are the firm's plans for navigating the financial landscape in 2025?   Key Timestamps: (00:00) - Reflecting on 2024 (01:40) - Cobblestone's Growth and Success (03:25) - Client Relationships and Market Insights (07:11) - Economic Trends and Predictions (11:26) - Building a Resilient Portfolio (18:10) - Looking Ahead to 2025   Key Topics Discussed: The Trusted Partner, Cobblestone Capital Advisors, Jesse Cramer, Gabe Chodak, Rochester New York, financial planning, investment management, investing markets, financial, client concerns, inflation and interest rates, Fed policy, economic uncertainty, portfolio management, wealth management, tax cuts, investment strategy, market predictions   Mentions: LinkedIn: https://www.linkedin.com/in/johndipasquale1/   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.

    31 min
  8. Avoid These Common Residential Real Estate Investing Mistakes | Michael Burton – E53

    12/26/2024

    Avoid These Common Residential Real Estate Investing Mistakes | Michael Burton – E53

    Michael Burton, a private investment analyst at Cobblestone Capital Advisors explores the intricacies of residential real estate investing. He shares his journey from junior year in college to owning multiple rental properties in Rochester, New York, and explains the due diligence required for successful real estate investments. The conversation includes insights into the importance of proper tenant screening, managing maintenance and capital improvements, the significant time commitment required, and the advantages of scaling up the number of rental units. Michael also compares direct property investment with other real estate exposure options such as public REITs and private funds, highlighting the risks and benefits of each. The episode wraps up with personal anecdotes and advice for those considering entering the residential real estate market.   Key Takeaways: • What are some key considerations and potential risks when investing in residential real estate? • How can prospective property investors balance between personal involvement and hiring third-party services to manage properties?  • What are the alternative ways to gain exposure to real estate investments without direct property ownership?   Key Timestamps: (00:00) - Michael's Journey into Real Estate (04:07) - The Realities of Property Management (07:57) - Financial Considerations and Risks (16:46) - Tenant Management and Property Scale (19:54) - Alternative Real Estate Investment Options (28:26) - Leveraging Debt in Real Estate   Key Topics Discussed: The Trusted Partner, Cobblestone Capital Advisors, Jesse Cramer, Gabe Chodak, Michael Burton, Rochester New York, financial planning, investment management, residential real estate investing, rental property, real estate portfolio, investment portfolio, real estate development, FHA loan, property investment, real estate investment solutions.   Mentions: LinkedIn: https://www.linkedin.com/in/michael-burton-8b2446183   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.

    35 min
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Ratings & Reviews

3.8
out of 5
6 Ratings

About

What does it take to make smarter financial decisions and secure your future? Welcome to The Trusted Partner, where Cobblestone Capital Advisors' Jesse Cramer and Gabe Chodak bring you engaging conversations with experts in financial planning, investment management, and wealth management. Designed to help you take control of your financial future, this podcast simplifies complex topics like tax-efficient investing, retirement planning strategies, and comprehensive financial planning. Whether you're navigating your growing career, preparing for retirement, or planning a lasting legacy, our expert guests provide practical advice tailored to real-world needs. Based in Rochester, NY, Jesse and Gabe combine their professional insights with relatable stories and actionable tips, helping you turn financial goals into achievable results. The Trusted Partner Podcast isn't just about managing money. It's about building confidence, securing peace of mind, and empowering you to make informed decisions for the long term. Tune in to The Trusted Partner Podcast and take the first step toward a smarter, brighter financial future.

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