G360 Wealth Podcast

Generation Capital Advisors

What’s the real story behind building and managing significant wealth? Welcome to the G360 Wealth Podcast, hosted by Generation Capital Advisors. Whether you are a first-generation wealth builder striving to create a legacy or part of a multi-generational family looking to preserve and grow your resources, the G360 Wealth Podcast is your guide to navigating the complex world of wealth management. Through a series of engaging mini-series and guest professionals, we’ll dive into topics that educate, inspire, and empower you to take control of your financial future. This series is dedicated to helping you develop the tools and confidence to make informed decisions about your personal and family finances.

  1. قبل ٤ أيام

    How the Smartest Investors borrow against their portfolio, without selling; with SyntheticFi (Ep. 17)

    Most investors think their only option for cash is to sell something. What if that’s not actually true? In this episode, Rex Berger sits down with Joseph Wang of SyntheticFi to discuss a strategy that has quietly been used by institutions and ultra-high-net-worth investors for years and is now becoming more accessible. They talk about box spreads in a way that actually makes sense, showing how investors can access liquidity without selling assets, triggering taxes, or sacrificing long-term growth. The conversation walks through real-world scenarios, from buying a home to funding renovations, and highlights both the opportunities and the risks. More importantly, it reframes how to think about liquidity as part of a broader wealth strategy rather than a one-time decision. What to expect: A simple explanation of what a box spread is and how it works How investors may access cash without selling appreciated assets Key differences between box spreads, margin loans, and securities-based lending Real-world use cases like home purchases and short-term liquidity needs The risks to understand, including margin calls and portfolio volatility How tax treatment may create additional planning flexibility Connect with Rex Berger:  LinkedIn: Rex Berger LinkedIn: Generation Capital Advisors Generation Capital Advisors Connect with Joseph Wang: LinkedIn: Joseph Wang LinkedIn: SyntheticFi SyntheticFi About our Guest: Joseph Wang is a co-founder of SyntheticFi, a firm focused on bringing institutional-level borrowing strategies to a broader audience. With a background in capital markets and financial engineering, Joseph helps advisors and investors access liquidity solutions traditionally reserved for hedge funds and family offices, with an emphasis on transparency, efficiency, and flexibility.

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  2. ٢٨ مايو

    Tax Alpha Unpacked: Strategy, Risk, and Reality with Brent Sullivan (Ep. 16)

    What if chasing tax savings is actually costing you more than you think? In this episode, Rex Berger and Sam Diarbakerly sit down with Brent Sullivan, founder of Tax Alpha Insider, to unpack what tax alpha really means and where investors often get it wrong. From direct indexing and long-short strategies to ETF innovation and concentrated stock solutions, the conversation goes beyond surface-level benefits and into the real trade-offs. Brent shares why tax strategies should never lead the conversation, how complexity can quietly introduce new risks, and what thoughtful, planning-first investing actually looks like for high-net-worth families. This episode is a grounded look at how to balance opportunity, risk, and long-term wealth stewardship. What to expect: A clear breakdown of what tax alpha actually means in practice The most common strategies being used today, including direct indexing and long-short Why pre-tax investment rationale matters more than tax benefits The hidden risks, complexity, and misconceptions investors should understand How advisors think about implementing these strategies within a full financial plan And more! Connect with Sam Diarbakerly:  LinkedIn: Sam Diarbakerly LinkedIn: Generation Capital Advisors Generation Capital Advisors Connect with Rex Berger:  LinkedIn: Rex Berger LinkedIn: Generation Capital Advisors Generation Capital Advisors Connect with Brent Sullivan: LinkedIn: Brent Sullivan LinkedIn: Tax Alpha Insider Tax Alpha Insider About our Guest: Brent Sullivan is the founder and editor of Tax Alpha Insider, where he focuses on tax-aware investing, portfolio construction, and the evolving strategies shaping high-net-worth wealth management. With experience spanning PIMCO’s trading floor, software development, and venture capital, Brent brings a unique perspective to integrating tax awareness into investment decisions while keeping planning at the center.

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  3. ٢٣ أبريل

    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 Connect with Sam Diarbakerly:  LinkedIn: Sam Diarbakerly LinkedIn: Generation Capital Advisors Generation Capital Advisors Connect with Jake Marriott: LinkedIn: Jake Marriott LinkedIn: Aptus Capital Advisors Aptus Capital Advisors 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.

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  4. ٢ أبريل

    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 LinkedIn: Generation Capital Advisors Generation Capital Advisors Connect with Jeffrey Krueger: LinkedIn: Jeff Krueger Seaport Financial Partners 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.

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  5. ٢٦ مارس

    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 Connect with Sam Diarbakerly:  LinkedIn: Sam Diarbakerly LinkedIn: Generation Capital Advisors Generation Capital Advisors Connect with Jack Vogel: LinkedIn: Jack Vogel LinkedIn: Alpha Architect Alpha Architect 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.

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  6. ٥ فبراير

    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, YPO Connect with Sam Diarbakerly:  LinkedIn: Sam Diarbakerly LinkedIn: Generation Capital Advisors Generation Capital Advisors Connect with Kurt Steinkrauss: LinkedIn: Kurt Steinkrauss LinkedIn: Mintz Mintz 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.

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  7. ١٨‏/١٢‏/٢٠٢٥

    Your Concentrated Stock Fix: Long-Short Direct Indexing with Jeff Murphy (Ep. 10)

    Managing a concentrated stock position or preparing for a significant tax year can create complex planning decisions. This episode outlines a practical framework for using direct indexing to support diversification, reduce concentrated exposure, and prepare for liquidity events in a controlled and tax-aware way. Rex Berger speaks with Jeff Murphy, Market Leader at Invesco, about how direct indexing works and why it has become a useful approach for handling concentrated stock, navigating equity-based compensation, and identifying tax opportunities within a portfolio. They discuss the differences between long-only and long-short structures, how tax loss harvesting functions in real portfolios, and how tracking error fits into overall portfolio design. The conversation includes examples relevant to business owners, corporate executives, and families managing long-term embedded gains. What to expect: How direct indexing builds index exposure while allowing for customization Why tax loss harvesting can be a valuable planning tool How long-short direct indexing helps investors with concentrated stock Examples of preparing for liquidity events and reducing tax pressure Connect with Rex Berger:  LinkedIn: Rex Berger LinkedIn: Generation Capital Advisors Generation Capital Advisors Connect with Jeff Murphy: LinkedIn: Jeff Murphy LinkedIn: Invesco Invesco About our Guest: Jeff Murphy is a market leader at Invesco with deep expertise in direct indexing, portfolio construction, and tax-sensitive investment strategies. He works closely with advisors across the country to help clients navigate concentrated stock positions, liquidity events, and the evolving world of personalized indexing.

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  8. ٠٤‏/١٢‏/٢٠٢٥

    Volatility as an Asset Class: How Aptus and GCA Tackle Investors’ Biggest Risks (Ep. 9)

    When the market is shifting faster than most people can keep up, the real risk isn’t volatility; it is holding on to outdated assumptions.  Rex Berger sits down with David Wagner from Aptus Capital Advisors to break down what investors should actually pay attention to right now. Rex and David open up the playbook behind Aptus’ philosophy of owning more stocks, fewer bonds, and still staying risk neutral. David shares why bonds may no longer serve as the traditional safety net many assume they are, how the 2022 drawdowns challenged decades of investment thinking, and why structure matters more than stock picking.  They also dig into longevity risk, drawdown math, and the discipline that guides Aptus’ collared strategy and compounder stock sleeve. It is a clear look into how to think forward, not backward, in a market full of noise. What to expect: Why bonds struggled in 2022 and what that means going forward How Aptus builds portfolios that balance conviction and protection A simple explanation of the collared strategy that sits inside ACIO Why long-term investors should focus on structure instead of prediction And more! Connect with Rex Berger:  LinkedIn: Rex Berger Generation Capital Advisors Connect with David Wagner: LinkedIn: David Wagner  Aptus Capital Advisors About our Guest: David Wagner is the Head of Equities and a Portfolio Manager at Aptus Capital Advisors. Known for his conviction-driven approach, he leads the firm’s equity research, active ETF strategies, and the widely followed Compounder Stock Sleeve. His work focuses on building practical, risk-aware structures designed to help investors navigate both the left tail and the right tail of market cycles.

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What’s the real story behind building and managing significant wealth? Welcome to the G360 Wealth Podcast, hosted by Generation Capital Advisors. Whether you are a first-generation wealth builder striving to create a legacy or part of a multi-generational family looking to preserve and grow your resources, the G360 Wealth Podcast is your guide to navigating the complex world of wealth management. Through a series of engaging mini-series and guest professionals, we’ll dive into topics that educate, inspire, and empower you to take control of your financial future. This series is dedicated to helping you develop the tools and confidence to make informed decisions about your personal and family finances.

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