Stock Options, RSUs, & Managing Concentration Risk | Allison Shuler - E55
The Trusted Partner Podcast - Wealth Strategies for High Net Worth Families
Release Date: 02/27/2025
Why Business Leaders Must Have a Voice in Government | Marc Cohen - E57
The Trusted Partner Podcast - Wealth Strategies for High Net Worth Families
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...
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The State of the World: Investing Amid Global Shifts | Jeff Kleintop - E56
The Trusted Partner Podcast - Wealth Strategies for High Net Worth Families
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...
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Stock Options, RSUs, & Managing Concentration Risk | Allison Shuler - E55
The Trusted Partner Podcast - Wealth Strategies for High Net Worth Families
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...
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Cobblestone’s Best Thinking on 2025 | John DiPasquale - E54
The Trusted Partner Podcast - Wealth Strategies for High Net Worth Families
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...
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Avoid These Common Residential Real Estate Investing Mistakes | Michael Burton – E53
The Trusted Partner Podcast - Wealth Strategies for High Net Worth Families
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...
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What You Need to Know Before Selling Your Business: Tips From an Investment Banker | David Riley - E52
The Trusted Partner Podcast - Wealth Strategies for High Net Worth Families
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. He highlights the vital role of investment banks in ensuring smooth transactions, particularly for family-owned businesses, and the importance of early planning and professional advising. Key...
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Life’s Best Investments Aren’t Financial | Kimberly Greulich - E51
The Trusted Partner Podcast - Wealth Strategies for High Net Worth Families
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 the benefits of using travel insurance and optimizing credit card points. Listeners are encouraged to prioritize experiential and transformative travel over visiting typical tourist spots, integrating...
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Fed Rate Cut. Now What? - E50
The Trusted Partner Podcast - Wealth Strategies for High Net Worth Families
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 provides practical advice on navigating these changes and emphasizes the importance of having a solid financial plan. Then hear about Gabe and Jesse’s light-hearted fall traditions. Key...
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Sports Cards: Cardboard or Currency? | Zach Stanley - E49
The Trusted Partner Podcast - Wealth Strategies for High Net Worth Families
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 driven by entertainment and social components emphasizing the importance of creating engaging experiences for collectors. Zach also discusses how new technology and social platforms have reshaped...
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Hedge Funds: Greedy or Misunderstood? | Jason Garlock - E48
The Trusted Partner Podcast - Wealth Strategies for High Net Worth Families
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 the manager's role and strategy. The episode also touches on the relevance of hedge funds in modern portfolios and effective ways to benchmark their performance. Finally, the group ends on a lighter...
info_outlineStock 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.