Perspectives Based on Knowledge

Guidance Forged by Experience

Tax Strategies for Concentrated Portfolios: What Smart Investors Are Doing

Tom Moran, Don Drury, and Charlie Chesebrough discuss tax-loss harvesting, direct indexing, charitable giving, and estate planning for investors with large embedded gains on Quarter

Pre-LOI Founder Exit Planning: What to Actually Prepare For

Signing an LOI shifts leverage to the buyer and closes several planning windows for good. Here's what to have in place before that happens.

Understanding the Role of Private Markets in a Portfolio

Charlie Chesebrough joins Dime After Dime (E021) to explain how private equity and private credit work, what illiquidity means for investors, how to think about

The Complete Guide to Florida Domicile in 2026

Moving to Florida is only the first step. Learn how former New York and California residents can document domicile and reduce residency-audit risk.

Family Office Alternatives After a Liquidity Event

A liquidity event changes the shape of a family's wealth, not just its size. Here are the realistic structural options, and why the decision can

Net Unrealized Appreciation (NUA): The 401(k) Tax Break Executives Miss

Learn how the net unrealized appreciation (NUA) rule can change how employer stock in a 401(k) is taxed, and when the strategy may fit your

Florida Declaration of Domicile: What the Statute Requires and How to File It

What a Florida Declaration of Domicile is, how Statute 222.17 works, and the steps to file the form, plus what it can and cannot do

Why 2026 Earnings Feel Different — and the Risks Nobody’s Pricing In

Tom Moran, Don Drury, and Charlie Chesebrough unpack why 2026 earnings look different from prior years, whether the market's broadening is durable, and what the

Insights That Drive Better Decisions

Stay ahead with expert perspectives on markets, risk, and opportunity, grounded in a disciplined approach to long-term wealth management.