G360 Wealth Podcast

Managing Concentrated Stock Risk with Covered Calls and Collars with Jake Marriott (Ep. 15)

You built the position. You watched it grow. Now the question is not how high it can go, but how much risk you are willing to take.  In this episode of the G360 Wealth Podcast, Sam Diarbakerly sits down with Jake Marriott, Options Portfolio Manager at Aptus Capital Advisors, to break down how options can be used in real-world wealth management. From covered calls to protective puts to structured collars, they walk through how these tools can help manage concentrated stock positions without rushing into a large tax event. Jake explains the mechanics in plain language, including how upside caps work, why early exercise risk is often misunderstood, and how shorter duration strategies can offer more flexibility. The conversation also highlights the importance of aligning any options strategy with a clear investment policy and realistic expectations. What to expect: * A simple explanation of calls vs puts * How covered calls can generate income while defining upside * How collars can create a risk “band” around a concentrated position * Why tax rules like the constructive sale rule matter * The difference between algorithmic overlays and hands-on management * And more! Resources: * Contact the team: https://www.generationcapitaladvisors.com/contact-us [https://www.generationcapitaladvisors.com/contact-us] Connect with Sam Diarbakerly:  * LinkedIn: Sam Diarbakerly [https://www.linkedin.com/in/samuel-diarbakerly-381a3052/] * LinkedIn: Generation Capital Advisors [https://www.linkedin.com/company/generation-capital-advisors/] * Generation Capital Advisors [http://www.generationcapitaladvisors.com] Connect with Jake Marriott: * LinkedIn: Jake Marriott [https://www.linkedin.com/in/jake-marriott-849a65142/] * LinkedIn: Aptus Capital Advisors [https://www.linkedin.com/company/aptus-capital-advisors/] * Aptus Capital Advisors [https://aptuscapitaladvisors.com/] The opinions expressed in this podcast are those of Aptus Capital Advisors, LLC (“Aptus”) as of the date of publication and are subject to change without notice. Information in the podcast is provided for information purposes only and should not be considered investment advice or a recommendation to purchase or sell any particular security, product or service. Aptus reserves the right to modify its current investment strategies and techniques based on changing market dynamics or client needs. The information is based on data obtained from sources believed to be reliable but are not guaranteed as being accurate and do not purport to be a complete summary of the available data. All investments involve risk, including loss of principal. Past performance is not indicative of future results. This should not be construed as tax, accounting, or legal advice. Aptus does not provide accounting, tax, or legal advice. You should always consult with a professional in these areas with regard to specific tax, accounting, or legal questions and obligations. Aptus Capital Advisors, LLC (“Aptus”) is an investment adviser registered with the U.S. Securities and Exchange Commission. Registration does not imply a certain level of skill or training. More information about Aptus’ investment advisory services can be found in its Form ADV Part 2 and/or Form CRS, both of which are available upon request. About our Guest: Jake Marriott is an Options Portfolio Manager at Aptus Capital Advisors, where he focuses on options overlay strategies for advisors and high-net-worth families. He works extensively with concentrated stock positions, helping clients structure covered calls, protective puts, and collar strategies aligned with their investment policy statements and long-term planning goals. His approach emphasizes education, disciplined execution, and ongoing communication to ensure strategies are implemented thoughtfully and monitored closely.

Roots and Wings: Navigating Family Wealth Without Losing What Matters with Brie Williams (Ep. 14)

What happens when your balance sheet grows faster than your family conversations? For many successful entrepreneurs and executives, the biggest question is not how to grow wealth, but how to pass it on without losing what matters most. In this episode of the G360 Wealth Podcast, Sam Diarbakerly sits down with Brie Williams, Managing Director and Head of Advisor Solutions and Wealth Intelligence at State Street Global Advisors, to explore the human side of wealth. Together, they unpack the “roots and wings” tension that families face, how money can magnify existing communication patterns, and why legacy is about more than trusts and tax strategies. Brie shares research-backed insights on multigenerational dynamics, emotional literacy, and how families can shift from one big inheritance conversation to an ongoing dialogue that builds confidence and capability over time. What to expect: * How wealth can quietly amplify both strong and strained family dynamics * Why communication is often more important than technical planning * Practical ways to create learning moments without creating dependency * The concept of “giving while living” and aligning expectations between givers and recipients * Book recommendations to strengthen emotional awareness and family governance * And more! Resources: * Atlas of the Heart by Brené Brown [https://www.amazon.ca/Atlas-Heart-Meaningful-Connection-Experience/dp/0399592555/ref=asc_df_0399592555?mcid=01401a00e952378b988627f6476e3ee9&tag=googleshopc0c-20&linkCode=df0&hvadid=706745308551&hvpos=&hvnetw=g&hvrand=14983891393573348145&hvpone=&hvptwo=&hvqmt=&hvdev=c&hvdvcmdl=&hvlocint=&hvlocphy=9001266&hvtargid=pla-1407906400294&psc=1&hvocijid=14983891393573348145-0399592555-&hvexpln=0&gad_source=1] * The Business of Family: How to Stay Rich for Generations by Linda Taylor Davis [https://www.amazon.ca/Business-Family-Stay-Rich-Generations-ebook/dp/B010O8J0HG] * Contact Generation Capital Advisors  [https://www.generationcapitaladvisors.com/contact-us] Connect with Sam Diarbakerly:  * LinkedIn: Sam Diarbakerly [https://www.linkedin.com/in/samuel-diarbakerly-381a3052/] * LinkedIn: Generation Capital Advisors [https://www.linkedin.com/company/generation-capital-advisors/] * Generation Capital Advisors [http://www.generationcapitaladvisors.com] Connect with Brie Williams: * LinkedIn: Brie Williams [https://www.linkedin.com/in/briepwilliams/] * LinkedIn: State Street Investment Management [https://www.linkedin.com/company/state-street-investment-management/] * State Street Investment Management [http://www.statestreet.com/im] About our Guest: Brie Williams is a Managing Director at State Street Global Advisors and leads Advisor Solutions and Wealth Intelligence. Her work focuses on researching investor behavior, family wealth dynamics, and the intersection of financial decision-making and human behavior. She partners with advisors and leadership teams across the country to translate research insights into meaningful conversations and real-world outcomes for families navigating complexity.

Equity Compensation Explained: How to optimize your Equity Comp With Jeffrey Krueger (Ep. 13)

If you have equity comp at work and you are not sure what you actually “have”, or what it could cost you at tax time, this episode will help you get oriented fast. Sam Diarbakerly sits down with Jeffrey Krueger, CPA, CFP®, Partner at Seaport Financial Partners, to break down the real tax story behind concentrated stock and equity compensation, the kind that can quietly create six or seven-figure surprises if you are not planning ahead. Using real-world executive scenarios, Sam and Jeff walk through the building blocks of equity comp, RSUs, non-qualified stock options, and ISOs, and explain why timing, withholding, and coordination matter. They also dig into QSBS (Section 1202) planning, including what it is, when it applies, and why early action can unlock meaningful long-term tax advantages for founders and employees at qualifying startups. Along the way, they keep it practical, focusing on how to avoid “bad surprises”, build a plan before a liquidity event, and keep your advisor team rowing in the same direction. What to expect: * A plain-English breakdown of RSUs, non-qualified options, and ISOs, and what triggers taxes for each * Why RSU withholding can fall short, and how surprise tax bills happen * How AMT works in the ISO conversation, and why it changes planning decisions * Why “sell right away” is often a smart default for vested RSUs (and when it might not be) * How an 83(b) election works, and why early timing can matter * QSBS (Section 1202) explained, plus what changed recently and why it expands planning flexibility * Why tracking grants, lots, and dates can save you real time, money, and stress later * And more! Connect with Sam Diarbakerly:  * LinkedIn: Sam Diarbakerly [https://www.linkedin.com/in/samuel-diarbakerly-381a3052/] * LinkedIn: Generation Capital Advisors [https://www.linkedin.com/company/generation-capital-advisors/] * Generation Capital Advisors [http://www.generationcapitaladvisors.com] Connect with Jeffrey Krueger: * LinkedIn: Jeff Krueger [https://www.linkedin.com/in/jeffkruegercpa/] * Seaport Financial Partners [https://seaportpartners.com/] About our Guest: Jeff Krueger is a Partner at Seaport Financial Partners. He is a CPA and a Certified Financial Planner practitioner, known for proactive tax planning and for helping business owners and corporate executives navigate complex equity compensation, concentrated stock, and liquidity-event planning strategies.

Episode Title: Section 351 Exchanges Explained: Simplifying Concentrated Stock Positions with Jack Vogel (Ep. 12)

What do you do when your biggest investment win becomes your biggest portfolio risk? In this episode of the G360 Wealth Podcast, Sam Diarbakerly sits down with Jack Vogel, Co-CIO of Alpha Architect, to unpack one of the most powerful yet underutilized tools in the tax code: the Section 351 exchange. For investors holding highly appreciated, concentrated stock positions, diversification can feel costly and complicated. Jack walks through how a 351 exchange works, who it may be appropriate for, and how it may help simplify portfolios without immediately triggering capital gains taxes, subject to meeting IRS requirements. They also explore how this strategy compares to exchange funds and direct indexing, where it fits within a broader wealth plan, and why simplification often leads to better long-term outcomes. What to expect: * A clear breakdown of what a Section 351 exchange is and how it works * The diversification rules required to qualify * How 351 exchanges compare to exchange funds and direct indexing * Why simplifying a complex portfolio may improve clarity and coordination * And more! Resources: * Contact Our Team [https://www.generationcapitaladvisors.com/contact-us] Connect with Sam Diarbakerly:  * LinkedIn: Sam Diarbakerly [https://www.linkedin.com/in/samuel-diarbakerly-381a3052/] * LinkedIn: Generation Capital Advisors [https://www.linkedin.com/company/generation-capital-advisors/] * Generation Capital Advisors [http://www.generationcapitaladvisors.com] Connect with Jack Vogel: * LinkedIn: Jack Vogel [https://www.linkedin.com/in/jack-vogel-8b826b13/] * LinkedIn: Alpha Architect [https://www.linkedin.com/company/alphaarchitect/] * Alpha Architect [https://alphaarchitect.com/] About our Guest: Jack Vogel is Co-Chief Investment Officer at Alpha Architect, where he oversees investment strategy and ETF development. Since co-founding the firm in 2010, Jack has helped build multiple business lines, including ETF operations, 1042 solutions for ESOP transactions, and Section 351 exchange strategies. His work focuses on delivering disciplined, research-driven investment solutions while helping advisors and investors navigate complex portfolio challenges with greater tax awareness and structural efficiency.

What Business Owners Should Think About Long Before a Sale with Kurt Steinkrauss (Ep. 11)

Most business owners spend years building the company, then treat the sale like it will “just work out.” In this episode, Sam Diarbakerly sits down with Kurt Steinkrauss, Partner at Mintz-Levin, to talk about what actually protects your outcome, before you ever go to market. Kurt breaks down what makes deals go smoothly and what quietly breaks them. Together, they unpack why “time is the enemy” once a sale process starts, why running your business like it’s for sale can change everything, and why the right advisory team matters more than most founders realize. The conversation also covers real tax and deal-structure landmines and how planning early can create options that simply disappear later. What to expect: * How to get “sale-ready” before an investment banker runs a process * Why entity structure (S corp vs C corp) can change your tax outcome * What reps and warranties insurance is, and why sellers care * The hidden leverage of early gifting and valuation discounts * Why your CPA, attorney, and advisor need to work as one team * And more! Resources: * Peer groups mentioned: Vistage [https://www.vistage.com/], YPO [https://www.ypo.org/] Connect with Sam Diarbakerly:  * LinkedIn: Sam Diarbakerly [https://www.linkedin.com/in/samuel-diarbakerly-381a3052/] * LinkedIn: Generation Capital Advisors [https://www.linkedin.com/company/generation-capital-advisors/] * Generation Capital Advisors [http://www.generationcapitaladvisors.com] Connect with Kurt Steinkrauss: * LinkedIn: Kurt Steinkrauss [https://www.linkedin.com/in/kurt-steinkrauss-122b1/] * LinkedIn: Mintz [https://www.linkedin.com/company/mintz-law/] * Mintz [http://www.mintz.com] About our Guest: Kurt Steinkrauss is a partner at Mintz, chair of the closely held business practice, and co-chair of the private equity practice. He advises entrepreneurs and executives through business sales, succession planning, and complex tax and estate planning, with a focus on protecting value on the front end and reducing risk on the back end.