Strategic perspectives on tax planning, retirement, investing, and the practice. Written by our partners — not by SEO content marketers. Quarterly digest mailed to clients and the email list. Substance only.
The post-retirement, pre-RMD window is often the lowest-tax-bracket period of your life. We model strategic conversions for most clients in their 60s — bracket-targeted, Medicare-IRMAA-aware, multi-year. The math works for most households with $1M+ in pre-tax accounts.
A market drop in your first 5 years of retirement is materially worse than the same drop in year 20 — by orders of magnitude. The bond-ladder + cash-buffer strategy we use to mitigate, and why it matters more than 'safe withdrawal rate' in current market conditions.
Most articles overstate harvesting benefits. The actual after-tax benefit, with realistic assumptions about future tax rates and rebalancing wash-sale rules. Why we harvest in November, not December, and the substantially-similar substitution we use.
Market timing systematically destroys returns. Disciplined rebalancing + tax-aware management captures most of the supposed timing benefit without the downside. Twenty-eight years of Cornerstone composite data; the math is uncomfortable for the timing camp.
If you might sell your business in the next 5 years, the planning starts now. Common structures (QSBS qualification, family-installment notes, charitable remainder trusts) + tax savings of $300K — $3M+ for typical owners. The 5-year-out window is the most-leveraged time to plan.
When to claim Social Security depends on your specific spousal situation, longevity expectations, and other income. Most blanket advice ('claim at 70') is wrong for most people. The break-even math + the spousal coordination is where the real decision lives.
Mailed quarterly to clients and the public list. No marketing, no sponsored content, no product pitches. The same issue clients receive. Email is a free subscription; the printed quarterly is mailed to clients only.
