The Elliot Omanson Show

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 They also cover why most people may not need a trust, how outdated beneficiaries can derail your wishes, and the emotional side of inheritance that can quietly tear families apart.If you want to avoid probate, protect your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.

The Social Security Decision That Could Cost You Hundreds of Thousands

Social Security may be one of the largest retirement assets most Americans will ever own — yet many people make claiming decisions without fully understanding the long-term consequences.In this educational discussion, Elliot Omanson and Nathaniel Vossman break down how Social Security actually works, including when to claim benefits, how delaying impacts retirement income, how Social Security is taxed, why spousal coordination matters, and how one decision can impact retirement income for decades.The conversation covers survivor benefits, delayed retirement credits, earnings limits while still working, longevity planning, Roth conversion considerations, taxation thresholds, and why Social Security should be treated like a major financial asset — not just a monthly check.Book a time to meet with Elliot to discuss Social Security, retirement planning, or your overall financial strategy: https://savvycal.com/owlfi/elliot

Growth vs Dividend Stocks: How to Create Income the Smart Way

Growth vs dividend stocks is one of the biggest debates in investing — especially when it comes to generating income.Most investors assume dividends are the best way to create income, but that’s not necessarily true. In this episode, we break down how dividend income actually works, why it’s often misunderstood, and how you can create income by selling shares instead.We also walk through the tax differences between dividends and capital gains, and why the type of account you use (taxable vs retirement accounts) can completely change the outcome.If you’ve ever wondered whether you really need dividend stocks to generate income, this will change how you think about building your portfolio.If you'd like a personalized retirement analysis, reach out to our team. Get a personalized retirement analysis: https://www.owlfi.com/contact

How Smart Investors Pay Less in Capital Gains Taxes

Most people assume capital gains taxes are unavoidable — but in reality, you can legally reduce them to 0% if you structure your income correctly.In this episode, we break down how capital gains are taxed, why your income (not your portfolio size) determines your rate, and how retirees can use smart strategies to minimize taxes over time. From capital gains harvesting to tax loss harvesting and income timing, this is how you keep more of what you’ve earned.The biggest takeaway: retirement isn’t about how much you have — it’s about how efficiently you use it.If you'd like a personalized retirement analysis, reach out to our team. Get a personalized retirement analysis: https://www.owlfi.com/contact

Murphy's Market Minute | April 17, 2026

The S&P 500 finished the week at a record 7,126, the Nasdaq posted its 13th consecutive winning session — its longest streak since 1992 — and the Russell 2000 also closed at a fresh all-time high. The Dow gained sharply on the week but did not reach record territory. While Q1 earnings have been solid — particularly from large-cap banks — this week's move was driven more by geopolitics than fundamentals.Progress toward a U.S.-Iran agreement and the reopening of the Strait of Hormuz led to a sharp decline in oil prices, easing immediate inflation pressure. This was the most important macro development of the week, as energy remains one of the key drivers of inflation expectations.Economic data continues to show resilience. Jobless claims came in at 207,000, reinforcing a stable labor market. However, consumer sentiment fell to a record low in April, highlighting a growing disconnect between strong markets and weaker consumer confidence.At their last meeting in March, the Federal Reserve held rates steady at 3.50%–3.75% and continues to signal one rate cut expected in the second half of 2026. Jerome Powell's term expires in May, with Kevin Warsh widely expected to succeed him — a transition worth monitoring for any potential shift in policy tone.

Murphy's Market Minute | April 10, 2026

Markets rebounded this week following a sharp drop in oil prices tied to a temporary ceasefire in the Middle East. While the S&P 500, Nasdaq, and Dow all pushed higher, the move was largely driven by relief that a worst-case geopolitical scenario may be avoided—at least for now.On the economic side, inflation data came in hotter than expected, with headline CPI rising to 3.3% year-over-year. However, this increase was driven almost entirely by a spike in energy prices, particularly gasoline. Core inflation, which excludes food and energy, remained relatively stable, reinforcing the idea that broader inflation pressures are still under control.Oil remains the key variable. After briefly spiking above $110 earlier in the week amid escalating tensions, prices pulled back sharply following the ceasefire announcement but remain elevated and volatile. With the Strait of Hormuz still a point of concern for global supply, energy markets are likely to remain sensitive to headlines.Overall, the market is currently operating under the assumption that inflation will ease if oil stabilizes and that economic fundamentals remain intact. However, this environment remains highly dependent on geopolitical developments, and any renewed escalation could quickly reverse recent gains.

How Much Do You REALLY Need to Retire? (Why Most People Get It Wrong)

How much money do you actually need to retire? The truth is, there is no “magic number” — and most people get this wrong. In this episode, we break down why traditional retirement advice often fails and what actually determines how much you need.We cover the biggest factors that impact your retirement plan, including spending habits, lifestyle expectations, taxes, healthcare costs, and inflation. You’ll also learn why relying on rules like the 4% rule can be dangerous, how retirement has shifted from pensions to self-funded income, and why taxes are often the biggest expense people overlook.This episode also dives into how Social Security fits into your plan, why expenses don’t disappear in retirement, and how strategies like Roth accounts can significantly increase your after-tax income. If you want a clearer, more realistic framework for retirement — this is it.If you'd like a personalized retirement analysis, reach out to our team. Get a personalized retirement analysis: https://www.owlfi.com/contact

How High Earners Pay Less in Taxes Using Oil & Gas

Most high earners overpay taxes. Here’s how they fix it.High-income earners are often told there’s nothing they can do to meaningfully reduce their tax bill. That’s not entirely true.In this episode, Elliot sits down with Steve Blackwell, CEO of Invito Energy Partners, to break down how oil & gas investments are used as a tax strategy to offset ordinary income. They explain how intangible drilling costs (IDC) and bonus depreciation work, why these deductions have existed in the tax code for over 100 years, and how they can be used alongside strategies like Roth conversions.They also explain why many investors lose money in oil & gas — and how to avoid those mistakes.If you’re a high earner looking for ways to reduce taxes or better understand advanced tax strategies, this is a complete breakdown. If you'd like a personalized retirement analysis, reach out to our team. Link to the OWLFI website with our contact info: https://www.owlfi.com/contact