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.

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.

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.

Concentrated stock positions can supercharge wealth creation or quietly threaten it. Rex and Sam break down the proven strategies that help you diversify smartly and protect your financial plan.

In this episode of the G360 Wealth Podcast, hosts Rex Berger and Samuel Diarbakerly unpack one of the most common and complex challenges for corporate executives and high-net-worth families: managing a concentrated stock position. Sam shares how these positions form, the risks they create, and the smart, tax-efficient strategies clients can use to diversify without losing hard-earned gains.

Through real-world examples and expert insights, Rex and Sam explore techniques like direct indexing, hedging, exchange funds, and charitable gifting to help listeners turn a concentrated holding into a more balanced and resilient portfolio. It’s an essential guide for anyone with significant equity exposure who wants to de-risk strategically and preserve long-term wealth.

What to expect:

• The biggest risks of holding a concentrated stock position
• How to diversify tax-efficiently using direct indexing and hedging
• When exchange funds or charitable giving strategies make sense
• Why planning first (before selling) can protect more than returns
• And more!

Resources:

• Charitable Giving with a Plan: Smarter Giving Strategies for Investors and Business Owners (Ep. 6)

Connect with Sam Diarbakerly:

• LinkedIn: Sam Diarbakerly
• Generation Capital Advisors

Connect with Rex Berger:

• LinkedIn: Rex Berger
• Generation Capital Advisors

How do discipline, innovation, and access to opportunity shape the future of wealth?

In this episode of the G360 Wealth Podcast, Sam Diarbakerly sits down with Christopher Zook, Founder and Chairman of CAZ Investments. They discuss health as a foundation for leadership, democratizing access to private investments, and why innovation is critical for advisors and families today.

Christopher also shares his approach to evaluating thousands of opportunities each year and the role of GP stakes in building resilient portfolios.

Christopher discusses:

• Why personal discipline in health and routines strengthens decision-making in business and investing
• The “20 billion in 20 years” goal at CAZ and how it aligns the firm and investors toward meaningful impact
• The democratization of private investments and why access matters for more families today
• The importance of innovation in alternatives, GP stakes, and thematic investing strategies
• How families can teach the next generation about wealth through philanthropy, structured conversations, and real-life investment examples
• And more!

Resources:

• Good to Great and Built to Last by Jim Collins

Connect with Sam Diarbakerly:

• LinkedIn: Sam Diarbakerly
• Generation Capital Advisors

Connect with Christopher Zook:

• LinkedIn: Christopher Zook
• CAZ Investments
• YouTube: The Holy Grail of Investing Podcast

About Our Guest:

Christopher Zook is the Founder, Chairman, and Chief Investment Officer of CAZ Investments. He has more than 30 years of experience investing in both traditional and alternative asset classes. Christopher recently co-authored “The Holy Grail of Investing,” with Tony Robbins, which became a #1 New York Times Bestseller. Christopher was honored with the Texas Alternative Investments Association’s (TAIA) Lifetime Achievement Award in recognition of his contribution and sustained support of the industry in Texas. He is a regular contributor to major media outlets, including CNBC, Fox Business, and Bloomberg. Prior to starting CAZ Investments in 2001, Christopher served in senior leadership positions with Oppenheimer, Prudential Securities, Lehman Brothers, and Paine Webber.

Christopher is actively involved in public policy and frequently serves as a resource to state and local officials. In 2019, Christopher was appointed by the Governor to serve on the State of Texas Pension Review Board, where he chairs the Investment Committee. He also served two terms as a member of the Greater Houston Partnership’s Executive Committee and is a past President of the “C” Club of Houston.

Christopher is a graduate of Texas Tech University, where he was honored as a Distinguished Alumni. A lifelong Houstonian, he is a former Vice-Chairman of the Deacons and served for more than a decade on the Finance Committee at Second Baptist Church. He has held leadership positions on a variety of charitable boards, including his current role on the board of Elizabeth Ruth’s Home, an organization serving adults with autism. Christopher previously served as President of the Board of Trustees of Avondale House and President of The Children’s Fund. He is a proud father to Christopher, Jr. (and daughter-in-law, Cecelia Zook, grandson “Tripp” and granddaughter Madelyn) and husband to his high school sweetheart, Lisa.

Giving Smarter: Real Strategies for Tax-Efficient Philanthropy

If you’re donating cash to charity, you might be missing out on major tax benefits.

In this episode of the G360 Wealth Podcast, Sam Diarbakerly sits down with Kyle Casserino of Fidelity Charitable to talk about a smarter way to give: donor-advised funds. These accounts let you make a charitable contribution, get an immediate tax deduction, and give to your favorite nonprofits over time, all while avoiding capital gains on appreciated assets.

Kyle breaks down how donor-advised funds actually work, why cash isn’t always the best gift, and how to think about giving if you’re a business owner, crypto investor, or just want a simpler way to support the causes you care about.

What to expect:

• How donor-advised funds give you flexibility and control
• Why donating stock or private business shares might save you more
• Tools that make giving as easy as sending money on your phone
• A behind-the-scenes look at Fidelity’s Private Donor Group for larger gifts

This conversation is about giving with intention, and with less friction.

Resources:

• Explore more at https://generationcapitaladvisors.com

Connect with Sam Diarbakerly:

• LinkedIn: Sam Diarbakerly
• Generation Capital Advisors

Connect with Kyle Casserino:

• LinkedIn: Kyle Casserino
• Fidelity Charitable

About Our Guest:

Kyle Casserino is a Vice President and Planning Consultant at Fidelity Charitable. With more than a decade of experience, he helps advisors and donors use charitable tools to align their giving with their goals—whether it’s a one-time gift or a legacy plan.

Most business owners think of retirement plans as something their payroll provider sets up, and that’s where the missed opportunity begins.

In this episode, Sam Diarbakerly talks with Jason Whitney, President of Whitney Pension Associates, about what really goes into building a smart retirement plan and why it matters more than people realize. They walk through how business owners, consultants, and board members can use 401(k)s, profit sharing plans, and cash balance plans not just to save, but to reduce taxes in a big way.

From a family business origin story to six-figure savings examples, Jason explains what a TPA actually does and how the SECURE Act 2.0 is making these strategies more accessible, especially for small businesses.

You’ll hear about:

• How 1099 income, board pay, and side gigs can be turned into tax-free retirement savings
• Why coordination between your CPA, advisor, and TPA is key to getting the most from your plan
• Real client stories, including one who cut a $400K tax bill with the right plan design
• The important window for setting up a retirement plan that still applies to last year’s taxes

Resources:

• Learn more at generationcapitaladvisors.com
• Visit whitneypension.com for retirement plan design services

Connect with Sam Diarbakerly:

• LinkedIn: Sam Diarbakerly
• Generation Capital Advisors

Connect with Jason Whitney:

• LinkedIn: Jason Whitney
• Whitney Pension Associates
• jwhitney@whitneypension.com
• 802-296-6500

About Our Guest:

Jason Whitney is the President of Whitney Pension Associates, a second-generation firm focused on retirement plan design. He joined the family business in 2007 after a career pivot that took him from a grad school degree to helping grow the firm’s national reach. Based in Vermont, Jason is also a Corporator for Mascoma Bank and a passionate New England sports fan. When he’s not helping clients with tax strategy, you’ll find him on the golf course, ski slope, or spending time with his wife and three kids.

What happens when families avoid the estate planning conversation?

In this candid and insight-packed episode, host Sam Diarbakerly sits down with estate planning attorney Crosby Elliott to uncover the often-overlooked truth: the greatest gift you can give your loved ones is clarity.

Together, they walk through the emotional, legal, and financial consequences of not having key documents like trusts, healthcare proxies, or powers of attorney in place. From avoiding probate court chaos to navigating guardianship for minor children, Crosby makes a complex topic feel human and manageable, with a touch of humor, too.

Here’s what you can expect from this release:

• A breakdown of why revocable trusts are often preferable to wills
• Real-world stories of what can go wrong without a plan
• Guidance on choosing the right healthcare proxy and guardian
• A checklist of critical documents to get in place now
• And more!

Connect with Sam Diarbakerly:

• LinkedIn: Sam Diarbakerly
• Generation Capital Advisors

Connect with Crosby Elliott:

• LinkedIn: Crosby Elliott
• Dalton & Finegold, LLP
• 617-377-4070
• celliott@dfllp.com

About Our Guest:

Attorney Crosby Elliott is a partner at the firm and assists individuals and families in all aspects of estate planning and trust and estate administration. Crosby’s experience in both planning and administration allow him to expertly advise clients through their many stages of life. Crosby prides himself on building relationships with clients to help simplify what can often be an overwhelming experience.

Crosby’s practice focuses on how best to minimize or avoid Massachusetts or federal estate taxes, avoid probate, shield assets from the cost of long-term care, and protect assets for beneficiaries. Crosby accomplishes these goals by employing sophisticated and comprehensive estate planning techniques, including the use of revocable trusts and various irrevocable trusts. Crosby also prepares federal gift tax returns.

A significant portion of Crosby’s practice also involves counseling clients through the administration of a loved one’s trust or estate. In doing so, Crosby regularly prepares and files both Massachusetts and federal estate tax returns, petitions with the probate court, and assists in dispute resolution between parties. Crosby also hosts presentations at businesses, organizations, and clubs on the importance of estate planning.

Outside of the office, Crosby enjoys spending time with his family, friends, and his dog. During the non-winter months, Crosby spends his free time either in Kennebunkport, Maine, hiking along the Appalachian Trail, or just generally enjoying the outdoors.