The Reverse Rollover: Turning Trapped Non-Deductible IRA Contributions into Tax-Free Roth Funds
For savvy investors and financial advisors, navigating the complexities of retirement planning often involves strategic maneuvers to optimize tax efficiency. Among these, the “Reverse Rollover” stands out as an exceptionally powerful, yet often underutilized, technique to convert non-deductible IRA contributions into a tax-free Roth IRA. If you’ve made after-tax contributions to a Traditional IRA and are now […]
PREMIUM TAX CREDIT CHANGES IN 2026: WHAT TO EXPECT AFTER THE “BIG BEAUTIFUL TAX BILL”
The passage of the “Big Beautiful Tax Bill” has introduced sweeping changes to several components of the U.S. tax code, including significant reforms to the Premium Tax Credit (PTC) system under the Affordable Care Act (ACA). Beginning in 2026, households who rely on marketplace subsidies to offset the cost of health insurance should prepare for […]
HOW THE NEW “TRUMP ACCOUNT” WORKS – AND WHY YOU SHOULD THINK TWICE BEFORE CONTRIBUTING
The recently passed “Big Beautiful Bill” (BBB) includes a provision creating a so-called “Trump Account” for all U.S. citizens born between 2025 and 2028. Each eligible child will receive a $1,000 contribution from the government, which must be invested in an index fund tracking the broad stock market, such as the S&P 500. These accounts […]
TARIFFS & RECENT MARKET DECLINES
In light of the drop in markets recently, we shared the following note Bob Veres sent out which perfectly captures Oak Street Advisors’ thoughts on the recent market pullback. The Awful Feeling of a Market Downturn Okay, is it all right to start panicking now? Many investors are asking themselves this question as the markets […]
THE SOCIAL SECURITY FAIRNESS ACT
The Social Security Fairness Act, signed into law in January 2025, repealed the Windfall Elimination Provision (WEP) and Government Pension Offset (GPO), restoring full Social Security benefits for public sector employees and their spouses. This repeal eliminates longstanding reductions in benefits for workers with government pensions and opens up new eligibility for spousal and survivor […]
ADVISOR SPOTLIGHT ARTICLES: INSIGHTS ON BASIC LIFE INSURANCE
Last month, Bryan Taylor was featured in two articles published by MoneyGeek, a website dedicated to personal finance content. Experts’ Insights on Basic Life Insurance Bryan Taylor, CFP® Vice President and Fiduciary Financial Advisor at Oak Street Advisors What are the major benefits and potential downsides of purchasing a basic life insurance policy? Basic life insurance […]
Navigating Retirement Plan Choices for Small Businesses: A Comprehensive Guide
Planning for retirement is crucial, especially for small business owners who often have to manage both their business and personal finances. Fortunately, there are various retirement plan options tailored to meet the needs of small businesses. In this article, we explore four popular choices: the SIMPLE IRA, the SEP IRA, 401(k) plans with after-tax contributions […]
Understanding different types of homeowners insurance
Different circumstances call for different types of homeowners insurance coverage. There are eight options for homeowners insurance available and you want to ensure you have the appropriate coverage for your individual needs. Having the wrong coverage could leave you with catastrophic liabilities that could endanger your financial security or independence. HOMEOWNERS INSURANCE POLICY OPTIONS: […]
THE CORPORATE TRANSPARENCY ACT
Heads up to all US business owners, that includes you, real-estate LLC! The Corporate Transparency Act (CTA) is a law that requires certain types of corporations, limited liability companies, and other similar entities created in or registered to do business in the United States to report their beneficial ownership information to the Financial Crimes Enforcement […]
529 PLANS: WHAT IF THE BENEFICIARY DECIDES NOT TO FURTHER THEIR EDUCATION?
Opening and funding a 529 plan for beloved one to help pay for future educational expenses is a smart and caring gesture, but what if the beneficiary decides not to attend an educational institution after graduating high school? Don’t worry! Assets in 529 plans always belong to the account owner rather than the beneficiary and […]
