The Elliot Omanson Show

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 ...

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 depr...

What really happens financially after losing a spouse? The “widow’s penalty” is one of the most overlooked risks in retirement—and it can result in higher taxes, lower income, and less flexibility, all at the worst possible time. In this episode, we break down why a surviving spouse can end up paying more in taxes despite earning less income. From losing a Social Security benefit to being pushed into higher single tax brackets, th...

Why do retirement plans fail, even for people who saved diligently for years? In this episode, Elliot Omanson and Nathaniel Vossman break down the biggest reasons retirement plans fall apart, including overspending, poor tax planning, panic selling, bad withdrawal timing, inflation, healthcare costs, and being too conservative with investments. They also explain how emotions can wreck a financial plan, why taxes can become one of ...

The week’s key focus was inflation. February’s Consumer Price Index (CPI) rose 0.3% month-over-month and 2.4% year-over-year, with Core CPI up 0.2% MoM and 2.5% YoY. The Fed’s preferred gauge, the Personal Consumption Expenditures (PCE) Price Index released today, increased 0.3% MoM and 2.8% YoY, while Core PCE rose to 3.1% YoY. These readings were broadly in line with expectations and suggest inflation continues moderating toward ...

CNN’s Jake Tapper brought on an Iranian activist expecting criticism of Trump’s actions toward Iran — but the interview completely backfired. Instead of attacking Trump or the U.S., the activist explained why many Iranians actually hope the regime is finally removed. In this Elliot Omanson Show short, Elliot reacts to the moment the narrative collapsed on live television. When Tapper tried to frame U.S. and Israeli actions as turn...

The 60/40 portfolio and the 4% rule have long been considered the standard formula for retirement planning. But do these strategies still work in today’s market environment? In this educational video, Elliot and Nathaniel explain how the traditional 60% stocks / 40% bonds portfolio structure became the industry standard and why the famous 4% withdrawal rule gained popularity after the Trinity Study and the research of William Beng...

Iran’s leaders have repeatedly called for Israel to be “wiped off the map.” Is it political rhetoric — or a real threat? As Iran advances its nuclear capabilities, the stakes are rising fast. In this episode of The Elliot Omanson Show, Elliot shares his perspective on Israel’s military strategy, the history of modern warfare, failed nuclear negotiations, and the difference between bureaucratic diplomacy and real-world dealmaking. ...

The main data release this week was Producer Price Index (PPI), which rose 0.5% versus expectations of 0.3%. Year-over-year PPI is now 2.9%, continuing its broader cooling trend despite the monthly bump. Mortgage rates dipped below 6% for the first time in over three years, with the 30-year fixed rate hovering around 6%. Some qualified borrowers are seeing mid-5% rates, though typically with points. Overall, rates are stabilizing....

Trump just delivered the longest State of the Union in modern history — nearly two hours — and it may have been the most strategically calculated speech of his presidency. In this episode of The Elliot Omanson Show, Elliot breaks down what stood out, from the economic messaging and “America First” framing to the direct callouts of Democrats during the speech. He explains why he believes this address was designed as a rallying cry ...

Estate planning shouldn’t sit in a drawer collecting dust. In this video, Elliot explains how we’re modernizing the estate planning process at OWLFI using the Vanilla platform and integrating it directly into the broader financial plan. Vanilla allows trusts, wills, powers of attorney, and medical directives to be created or restated inside a clean digital system that actually maps out how assets flow. Instead of just reading lega...

Social Security taxes are one of the most misunderstood parts of retirement planning — especially when it comes to how much of your benefits can actually become taxable. In this episode, we break down how Social Security is taxed at the federal level, why up to 85% of your benefits can be included as taxable income, and how the provisional income calculation determines what you owe. We explain how IRA withdrawals, pensions, and Re...

Elliot is introducing his brother, Glen Omanson of United Team Tax, who will now provide individual tax preparation and proactive, year-round tax planning for OWLFI clients as part of your ongoing relationship with the firm. Glen has been in the financial services industry since 2009 and holds the IRS's highest credential, Enrolled Agent (EA). His expertise focuses exclusively on individual taxation. Throughout his career—includin...

U.S. stocks are positive for the week with the major indices in the green as of Friday, as investors digested mixed economic data and a notable legal development on trade policy. The Supreme Court struck down broad tariff authority in a ruling this week, reducing the risk of sweeping new trade measures and providing a modest boost to investor sentiment. On the economic front, fourth-quarter GDP was revised to 1.4% annualized, shar...

This week’s focus centered on the January employment report and the latest inflation data, both of which play a critical role in shaping Federal Reserve policy expectations. The labor market remains stable. The economy added 130,000 jobs, well above expectations, while the unemployment rate held steady at 4.3%. Average hourly wages rose 0.4% month over month and are up 3.7% year over year, signaling continued strength without clea...

California taxes just hit the Super Bowl — and Sam Darnold’s bill shocked everyone. After spending eight “duty days” in California leading up to the Super Bowl, Darnold reportedly owes roughly $249,000 in state income taxes — more than the $178,000 Super Bowl bonus paid to players on the winning team. In this episode, we break down how the NFL “duty day” tax formula works, why California’s 13.3% top rate matters, how Washington’s...

Equity markets experienced early-week pressure, concentrated in large-cap technology, as investors assessed elevated AI-related capital spending and its potential impact on margins and growth durability. The S&P 500 and Nasdaq weakened mid-week amid uneven sector performance, while small-cap stocks showed relative resilience as the week progressed. Markets stabilized toward week’s end as selling pressure eased and participatio...

Roth conversions could be the most important retirement tax strategy most investors ignore. In this educational breakdown, we explain how Roth accounts work, why conversions matter, and how they can help you avoid Social Security taxation, IRMAA Medicare surcharges, and unnecessary tax bracket jumps in retirement. If you have an IRA, 401(k), or brokerage account, this strategy could significantly impact your retirement taxes. We...

Nearly 40% of Stanford undergraduates now claim disability accommodations — not because they can’t function, but because the system rewards it. In this episode of The Elliot Omanson Show, we break down a shocking article exposing how elite universities incentivize students to identify as “disabled” to gain advantages like single dorms, extra time on exams, and academic exemptions. What starts on campus doesn’t stop there — it foll...