The Social Security Decision That Could Cost You Hundreds of Thousands

Murphy's Market Minute | June 5, 2026

The U.S. labor market remained surprisingly strong this week, with employers adding 172,000 jobs in May compared to expectations of just 80,000. Wage growth also remained elevated, reinforcing the idea that the economy continues to show resilience despite higher interest rates. While strong employment is generally positive, it also reduces the likelihood of near-term Federal Reserve rate cuts, which contributed to some market volatility following the report. Despite Friday's pullback, major indexes remain near all-time highs. The Dow Jones Industrial Average recently surpassed 51,000, while the S&P 500 and Nasdaq continue to trade within striking distance of record levels. Oil prices remain elevated, and cryptocurrency markets experienced a sharp decline this week, with Bitcoin falling back into the $60,000 range. In addition to our market update, we're excited to share a preview of OWLFI's new client portal. Designed to simplify your financial life, the platform brings together investment accounts, insurance policies, banking relationships, appointments, market updates, estate planning resources, and more in one centralized location. The portal will be rolled out incrementally, and clients interested in early access are encouraged to contact our team. As always, thank you for trusting OWLFI with your financial future. If you have questions about the markets, your plan, or the new client portal, we're here to help.

Meet OWLFI's New COO: Chris Smith Joins the Team

Chris Smith has officially joined OWLFI as our new Chief Operating Officer (COO). In this conversation, Elliot sits down with Chris to discuss his background, from military deployments in Iraq to building and scaling multi-million-dollar businesses. They also share why now was the right time for Chris to join the firm and how his expertise in systems, processes, and organizational growth will help strengthen the client experience for years to come. Plus, Elliot gives a brief preview of this week's Murphy's Market Minute, including recent ADP jobs data and what rising wages could mean for the economy. We hope you'll join us in welcoming Chris to the OWLFI family.

Estate Planning Explained: Wills, Trusts, Probate & Common Mistakes

What actually happens to your money when you die? Most people procrastinate estate planning — and many make costly mistakes that create family conflict, probate headaches, unnecessary legal fees, or even send assets to the wrong person. In this episode, Elliot Omanson and Nathaniel Vossman break down estate planning in plain English: wills, trusts, probate, beneficiary designations, powers of attorney, healthcare directives, and the biggest mistakes families make. They also cover why most people may not need a trust, how outdated beneficiaries can derail your wishes, and the emotional side of inheritance that can quietly tear families apart. If you want to avoid probate, protect your family, and make sure your assets go where you actually intend, this conversation is a must-watch. Whether you’re married, divorced, have kids, stepchildren, or significant retirement assets, estate planning is something you can’t afford to ignore. 📅 Book a time to meet with Elliot: https://savvycal.com/owlfi/elliot

How Trusts Can Legally Defer Capital Gains Taxes

If you’re selling a business, highly appreciated real estate, cryptocurrency, or another major asset, capital gains taxes could take a massive portion of your wealth. In this episode, Elliot Omanson and Nathaniel Vossman explain how properly structured trusts may help defer capital gains taxes, improve flexibility, and potentially help you keep more of what you’ve earned. The conversation covers business sales, appreciated real estate, installment sale concepts, constructive receipt, tax timing, and why some high-net-worth families structure liquidity events differently than most people. Before selling a business, property, or other appreciated asset, this is a strategy worth understanding. 📅 Book a time to meet with Elliot: https://savvycal.com/owlfi/elliot

Murphy's Market Minute | May 8, 2026

U.S. stocks moved higher this week, supported by a stronger-than-expected April employment report. The economy added 115,000 nonfarm payrolls — well above consensus expectations near 55,000 — while the unemployment rate held steady at 4.3%. Wage growth also came in softer than expected, with average hourly earnings rising 0.2% for the month and 3.6% year-over-year. Cooler wage growth is viewed positively by markets because it reduces the risk of labor costs contributing to persistent inflation pressures. Job gains were concentrated in healthcare, transportation and warehousing, and construction, while federal government employment continued to decline. Earlier in the week, the ISM Services PMI for April came in at 53.6%, marking the 22nd consecutive month of expansion in the services sector. However, investors were more focused on the Prices Paid component, which remained elevated at 70.7% — a four-year high — signaling that service-sector inflation pressures remain persistent. Since services account for roughly 70% of U.S. economic activity, sticky services inflation remains one of the primary obstacles preventing the Federal Reserve from signaling imminent rate cuts. Consumer sentiment continued to weaken as well. The University of Michigan’s preliminary May sentiment reading fell to 48.2 from April’s 49.8 reading, remaining among the lowest levels on record. Higher energy costs and broader economic uncertainty continue to weigh on household confidence, even as long-term inflation expectations remain relatively stable.