PODCAST

Cobblestone Capital Advisors

All Episodes

33:13

Episode 60 – Why Most DIY Investors Fail: Inside the...

Cobblestone Capital Advisors ·

2025/07/31

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.

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26:16

Episode 59 – DelMonte and CityGate: Rochester’s Next...

Cobblestone Capital Advisors ·

2025/06/16

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

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39:32

Episode 58 – Why Smart People Make Dumb Decisions

Cobblestone Capital Advisors ·

2025/05/29

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.

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31:26

Episode 57 – Why Business Leaders Must Have a Voice...

Cobblestone Capital Advisors ·

2025/04/24

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.

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32:27

Episode 56 – The State of the World – Investing Amid...

Cobblestone Capital Advisors ·

2025/03/27

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

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32:41

Episode 55 – Stock Options, RSUs, & Managing...

Cobblestone Capital Advisors ·

2025/02/27

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

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27:19

Episode 54 – Cobblestone’s Best Thinking on 2025

Cobblestone Capital Advisors ·

2025/01/30

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.

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35:28

Episode 53 – Avoid These Common Residential Real...

Cobblestone Capital Advisors ·

2024/12/26

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.

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28:59

Episode 52 – What You Need to Know Before Selling...

Cobblestone Capital Advisors ·

2024/11/29

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.

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34:17

Episode 51 – Life’s Best Investments Aren’t Financial

Cobblestone Capital Advisors ·

2024/10/31

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.

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33:56

Episode 50 – Fed Rate Cuts. Now What?

Cobblestone Capital Advisors ·

2024/09/27

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.

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38:29

Episode 49 – Sports Cards: Cardboard or Currency?

Cobblestone Capital Advisors ·

2024/08/29

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.

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38:58

Episode 48 – Hedge Funds Greedy or Misunderstood

Cobblestone Capital Advisors ·

2024/07/31

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.

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37:05

Episode 47 – Should Couples Combine Their Finances?

Cobblestone Capital Advisors ·

2024/06/06

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.

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31:17

Episode 46 – Smart Golf = Smart Investment Management

Cobblestone Capital Advisors ·

2024/05/24

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.

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30:58

Episode 45 – Investing in Commodities – Is it Fool’s...

Cobblestone Capital Advisors ·

2024/05/09

Jesse and Gabe are joined by Charlie Ruff, Cobblestone's Head of Investment Strategy & Communications, to discuss commodities investing: the good, bad, and ugly.

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36:04

Episode 41 – The Compound Value of Tax Planning

Cobblestone Capital Advisors ·

2024/03/18

Gabe and Jesse sit down with Tobin Woodruff, a Senior Wealth Planner at Cobblestone Capital Advisors.

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31:44

Episode 39 – Earnings Season: What to Watch For

Cobblestone Capital Advisors ·

2024/02/15

Gabe and Jesse sit down with Charlie Ruff, senior portfolio manager at Cobblestone, to discuss the details of earnings season in the stock market.

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35:29

Episode 38 – When Do You Need Personal or Business...

Cobblestone Capital Advisors ·

2024/02/01

Gabe and Jesse chat with Adrian Morgenstern, founder and president of Morgenstern Insurance Services, about the intricacies of personal and commercial insurance.

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47:41

Episode 37 – Reviewing ’23 and Looking to ’24

Cobblestone Capital Advisors ·

2024/01/19

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.

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