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.