Taxes

A Year of Deferring Capital Gains: What It Saved and What It Cost

Owen Castellano shares a first-person account of deferring capital gains for a year and the surprising lessons learned for long-term tax planning.

Analyst: Owen Castellano 15 min read

Roth IRA Rollovers to a 401(k) Overlook a Key Tax Advantage

Discover why rolling a Roth IRA into a Roth 401(k) is often a missed opportunity for tax-free growth and flexibility.

Analyst: Owen Castellano 12 min read

Inherited Wealth: Costly Tax Mistakes That Undermine Long-Term Plans

Discover common tax mistakes with inherited wealth and learn how to avoid costly errors for long-term financial stability.

Analyst: Owen Castellano 12 min read

Do Taxable Brokerage Accounts Need Special Tax Planning?

Discover essential tax planning strategies for taxable brokerage accounts, beyond just basic investing rules. Avoid common mistakes and maximize returns.

Analyst: Owen Castellano 15 min read

Roth IRA Direct Contribution Versus Backdoor Roth: Which Path Suits Your Income?

Navigate Roth IRA contributions: direct vs. backdoor Roth for higher earners. I share my experience optimizing tax-free growth.

Analyst: Owen Castellano 18 min read

A $3,000 Capital Loss: Why This Number Drives So Many Investment Decisions

Owen Castellano explains how the $3,000 capital loss deduction cap influences long-term investment strategies and tax-smart wealth planning.

Analyst: Owen Castellano 12 min read