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.

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.

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.