Advanced Investing and the US Economy
Navigate macro business cycles, exploit structural tax inefficiencies, and deploy institutional-grade portfolio construction strategies in modern US financial markets.
Like Duolingo, but for Advanced Investing and the US Economy. Tomo turns the whole topic into a game you play five minutes a day, until it actually sticks.
20 levels across 3 sections, about 40 minutes end to end, roughly 8 days at five minutes a day. It moves through Tax-Advantaged Portfolio Architecture, The Macroeconomic Transmission Mechanism, and Institutional Portfolio Construction and Risk Architecture.
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Key ideas in Advanced Investing and the US Economy
- Swapping between different share classes or wrappers of the exact same fund (such as VOO to VFIAX) tracks the exact same underlying index and issuer, making it vulnerable to being deemed 'substantially identical' by the IRS.
- Replacing an S&P 500 tracking vehicle with a fund tracking a different broad large-cap index (such as the Dow Jones U.S. Large-Cap or Russell 1000) provides near-identical beta and sector weightings while tracking distinct underlying benchmarks with different reconstitution methodologies.
- Acquiring contracts or options to acquire stock (like deep-in-the-money puts or call options) within the 30-day window triggers wash-sale disallowance under Section 1091.
- Broad market indices conceal significant internal dispersion: even in strongly bullish years, dozens of constituent companies routinely experience steep idiosyncratic drawdowns.
- Holding the underlying single stocks directly allows individual lot-level harvesting of losers while letting the winners run, producing realized capital losses that an aggregate ETF or mutual fund wrapper would internally net out and obscure.
- The Net Investment Income Tax (NIIT) imposes a 3.8% surtax on the lesser of net investment income or the excess of modified adjusted gross income (MAGI) over statutory statutory thresholds ($250,000 for married filing jointly, not indexed to inflation).
- Bracket topping selectively realizes income or gains up to the exact cliff or threshold where new tax regimes (such as NIIT or higher capital gains brackets) become active.
- Net investment income includes taxable interest, dividends, and net realized capital gains, which add dollar-for-dollar to MAGI.
- Specific Identification requires contemporaneous designation of unique purchase dates and unit prices at the time of trade execution, permitting optimal high-basis harvesting (HIFO).
- FIFO is the standard broker default, which typically triggers maximum tax drag in secularly rising bull markets by selling the lowest-basis legacy shares first.
- Electing average cost on mutual fund shares blends the basis across all past and future purchases, forfeiting the right to strategically isolate high-cost and low-cost shares for targeted disposition.
- REIT distributions are primarily taxed as ordinary income rather than qualified dividends, making them heavily tax-inefficient in taxable accounts
- Passive index equity ETFs generate low turnover and qualified dividends, which benefit from preferential long-term capital gains rates and foreign tax credits in taxable accounts
- Placing the asset with the highest expected upside in a Roth wrapper maximizes the dollar value of permanent tax-free compounding
- Roth IRAs have no lifetime Required Minimum Distributions (RMDs) for the original owner, allowing high-beta compounders to run uninterrupted across multi-decade horizons
- Traditional IRAs force RMDs that convert capital gains into ordinary income tax upon withdrawal, creating compounding drag on fast-growing assets
You've tried the other tabs
Thirty open tabs. Four facts you actually kept.
You watched. You nodded. By Sunday it was gone.
One answer, then back to scrolling.
Eight weeks. You meant to finish. You didn't.
Tomo gives Advanced Investing and the US Economy the Duolingo treatment: levels, streaks, and quick quizzes that test what you just learned. That game loop is what the tabs above never had, so it's the one you actually finish.
Here's what playing it feels like
A real question from this course. Take your best guess.
You harvest a loss in an S&P 500 fund. How can you stay fully invested without triggering a wash sale?
Get it right to open this lesson and 19 more in the app.
Where Advanced Investing and the US Economy takes you
- 1
Tax-Advantaged Portfolio Architecture
- Tactical Tax-Loss Harvesting and Wash-Sale Engineering
- Strategic Asset Location and Capital Structuring
- 2
The Macroeconomic Transmission Mechanism
- Federal Reserve Policy and Liquidity Dynamics
- Yield Curve Mechanics and Credit Signals
- Labor Structural Dynamics and Fiscal Impulse
- 3
Institutional Portfolio Construction and Risk Architecture
- Factor Exposures and Risk Premia
- Asymmetric Hedging and Volatility Regimes
3 sections · 7 units · 20 levels. Built to play, not to enroll.
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