Cobblestone Capital Advisors

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

Business EN ↓ 60 episodes

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 expe...

Author

Cobblestone Capital Advisors

Category

Business

Podcast website

sites.libsyn.com

Latest episode

Jul 31, 2025

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Episodes

Why Most DIY Investors Fail: Inside the Mind of a High-Conviction Value Investor | Oleg Litvinenko - E60 31.07.2025

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 focuse...

DelMonte and CityGate: Rochester's Next Landmark Hotel - E59 14.06.2025

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 ju...

Why Smart People Make Dumb Decisions - E58 29.05.2025

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 countera...

Why Business Leaders Must Have a Voice in Government | Marc Cohen - E57 24.04.2025

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...

The State of the World: Investing Amid Global Shifts | Jeff Kleintop - E56 27.03.2025

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 e...

Stock Options, RSUs, & Managing Concentration Risk | Allison Shuler - E55 27.02.2025

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...

Cobblestone's Best Thinking on 2025 | John DiPasquale - E54 30.01.2025

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 in...

Avoid These Common Residential Real Estate Investing Mistakes | Michael Burton – E53 26.12.2024

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 tena...

What You Need to Know Before Selling Your Business: Tips From an Investment Banker | David Riley - E52 28.11.2024

David Riley, an expert in investment banking, discusses the intricacies of the industry, especially within the context of Western New York. He breaks down how investment banks facilitate large-scale financial transactions, including mergers, acquisitions, and capital raising. David also delves into the different market segments, from top-tier firms like Goldman Sachs to middle-market institutions....

Life's Best Investments Aren't Financial | Kimberly Greulich - E51 31.10.2024

Gabe and Jesse explore the world of travel with Kim Greulich, owner of KG Travel Club. As a travel expert, Kim guides listeners through enhancing travel experiences beyond conventional methods. The discussion covers the importance of travel as an investment in personal growth and family bonding, exploring lesser-known destinations, and smart budget management. Additionally, Kim shares insights on...

Fed Rate Cut. Now What? - E50 27.09.2024

Gabe and Jesse discuss the Federal Reserve's recent September 20th 50 basis points rate cut and its ramifications. They explore the effects on various investment decisions, such as high-yield savings accounts and fixed-income investments, and the broader implications for the stock and real estate markets. They also address how high-net-worth individuals and retirees might be impacted. The episode...

Sports Cards: Cardboard or Currency? | Zach Stanley - E49 29.08.2024

Zach Stanley joins the podcast to share insights into the future of the sports card industry, its role as an alternative asset and Zach's personal stories of treasured sports memorabilia. Zach explains the concept of card breaking, the financial rationale for buying specific teams and its impact on the sports card industry. He elaborates on the evolution of the industry, describing how it has been...

Hedge Funds: Greedy or Misunderstood? | Jason Garlock - E48 25.07.2024

Jesse and Gabe are joined by Jason Garlock, Chief Investment Officer at Cobblestone Capital Advisors, to demystify hedge funds. The conversation covers what hedge funds are, their legal structure, investment strategies, performance metrics, fee structures, and regulatory environment. Jason draws comparisons with mutual funds and traditional investments, emphasizing the importance of understanding...

Should Couples Combine Their Finances? | E47 06.06.2024

Jesse and Gabe sit down with Allison Schraf, a Senior Wealth Planner at Cobblestone Capital Advisors, to discuss the pros and cons of couples (whether married or not) combining their finances. Topics include:   - the importance of communication, transparency, and compromise.    - practical advice on creating a household budget, allocating expenses, and managing joint finances.   - the importance o...

Smart Golf = Smart Wealth Management - E46 23.05.2024

Jesse and Gabe meet at the 9th green at 9 for a chat about golf and wealth management, and the varied similarities between the two. Both are exercises in:   - Seeking reward while managing risk   - Striving to reach your own personal goals, ignoring the outside noise   - Planning for what's next and looking ahead    - Occasionally hitting it the sand - but focusing on a smart recovery   - Seeking...

Investing in Commodities: Is it Fool's Gold? 09.05.2024

Jesse and Gabe are joined by Charlie Ruff, Cobblestone's Head of Investment Strategy & Communications, to discuss commodities investing: the good, bad, and ugly. Specifically, the three discuss:    - what are the different "genres" of commodities?    - why does the commodities market exist?    - is it worth considering commodities in a diversified portfolio?    - do you have to *own* the physical...

Should You Own International Stocks? - E44 26.04.2024

Jesse and Gabe are joined by Jordan Millner, Cobblestone's Head of Global Equities, to discuss the merits of international stocks within a diversified portfolio. They answer questions such as:   - Do international stocks traditionally outperform U.S. stocks, or vice versa?   - Why can't multinational corporations (e.g. Apple) be considered "international investing?"   - What are generally accepted...

$100,000 Per Year?! Let's Talk 529 Plans 11.04.2024

Jesse and Gabe go deep on the topic of 529 plans today, helping their listeners understand this fundamental tool in saving for college. Their conversation covers:    - The basics of 529 plans   - The major benefits, such as tax-free investment growth   - The downsides, like illiquidity and penalties for certain withdrawals    - The nuance of the recently publicized "529 to Roth" conversion   - How...

Running the Rochester Red Wings - E42 28.03.2024

Charlie Ruff and Jesse Cramer (sorry Gabe!) sit down with Dan Mason, the General Manager of the Rochester Red Wings, to talk all things Minor League Baseball. Their conversation covers:    - The Red Wings' new "bat dog," Bruce!  - Ball park fun in the minors - Interactions between different teams' general managers  - The business model of the minors - Dan's top Red Wings players ever - and much mo...

The Compound Value of Tax Planning - E41 16.03.2024

Gabe and Jesse sit down with  Tobin  Woodruff, a Senior Wealth Planner at Cobblestone Capital Advisors.  Tobin  is an expert on tax planning, so today's conversation revolves around:   - The basics of a 1040 Federal Tax return, and why individuals need to be aware of it   - When to know if you need a tax professional   - Withholdings and refunds    - Tax tips for both young and old investors   - "...

Hard Money Talks with Family and Friends - E40 29.02.2024

Gabe and Jesse chat 1-on-1 about how to conduct challenging financial conversations with friends and family. It's never easy. But done well, having an important financial conversation helps everyone involved, and prevents negative emotions in the long run. Specifically, Gabe and Jesse cover:   - The various people in life who you'll end up "talking money" with   - How to broach the conversation in...

Earnings Season: What to Watch For 15.02.2024

Gabe and Jesse sit down with Charlie Ruff, senior portfolio manager at Cobblestone, to discuss the details of  earnings  season in the stock market. Their conversation includes:   - What is  earnings  season, and why should we care about it?   - What data do companies release, and what kind of conversations do they have with investors?    - How useful is  earnings  season, and what takeaways shoul...

When Do You Need Personal or Business Insurance? - E38 01.02.2024

Gabe and Jesse chat with Adrian Morgenstern, founder and president of Morgenstern Insurance Services, about the intricacies of personal and commercial insurance. Their conversation includes:   - Going beyond simple home and auto policies - The difference between growing wealth and protecting wealth - Important questions people should consider about their personal risk appetite  - How business/comm...

Reviewing '23 and Looking to '24 - E37 19.01.2024

Gabe and Jesse chat with Cobblestone CEO and Managing Partner John DiPasquale to review the year of 2023 and look at significant economic and investing questions facing us all in 2024. Specific topics include:   - How'd the market do in 2023, and why? - The important takeaways from 2023, including thoughts on cash allocations and broad diversification - How expectations played a role in 2023 resul...

Ask Us Anything (Volume #2) - E36 04.01.2024

Gabe and Jesse answer listener questions for their second rendition of "Ask Us Anything." Topics for this episode include:   - "Why did my account go up so much in November and December?"   - "S&P, Dow Jones, NASDAQ...which index should I be looking at?"   - "Should I have *any* money in banks right now with low interest rates?"   - "How are capital gains taxes calculated?"   - "When should I star...

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