Street Sheet Strategies

Professionally managed portfolios for self-directed investors

Three done-for-you, actively managed strategies for do-it-yourself investors. Built by professionals and monitored daily, these portfolios include every holding, every weighting, and most importantly, why.

Designed specifically to take the guessing and the stressing out of your investing.

Turn Reactive Guessing into Proactive Investing


Doing it yourself usually means reacting.

The market drops, and you scramble. A headline spooks you, and you sell. A tip excites you, and you buy.

Every move is a guess made after the fact, under pressure, with your stomach in a knot — and that's the real stress of investing on your own. Not the market itself. The guessing.

Proactive investing is the opposite.

The positioning, the weightings, and the response to what comes next are decided ahead of time, as part of a system — so when conditions change, you already know what it means and how the strategy responds.

Calm, deliberate, planned. Not a panic.

That's what Street Sheet Strategies is built to do. Three professionally managed portfolios where every holding has a job, every weighting has a reason, and the plan is already in place before the market moves.

You see exactly what's held, how much, and most importantly, why. When something changes, a letter tells you what and what it means.

You stop guessing after the fact and start operating ahead of it.

That's the whole shift: stressful guessing turns into purposeful investing.

Built, Managed, & Monitored By Professionals


The Strategies are built and run by DePaolo & May Strategic Wealth — an independent, fee-only fiduciary investment firm based in Orange County, California.

They answer to no broker-dealer, bank, or insurance company and have no products to push, so they build portfolios from the best investments available across the entire market.

Their approach is active, not buy-and-hope: tactical, theme-based portfolios designed to outperform over full cycles, researched deeply, monitored daily, and adjusted when the data calls for it.

It's the same institutional-grade process they run for their private clients, now powering every Street Sheet Strategy.

Here’s Exactly What’s Included As Soon As You Join


The Inaugural Letter (right when you join)

Each strategy opens with a full inaugural letter: the complete framework laid out once, so every monthly update after it lands in context. It's the owner's manual for the strategy, and it walks through all seven layers of how the portfolio is built and managed:

How We Build the Portfolio: The GRID Framework. Three macro inputs (GDP growth, inflation, interest rates) map the market into one of four regimes — Goldilocks, Reflation, Inflation, Deflation. The regime sets net equity, sector tilts, and hedge sizing. Everything flows from here.

Within Equities: Earnings, Momentum, Valuation. The three signals that size every position, applied in order. When all three agree, the name is sized large; when two of three disagree, it goes on the watchlist. You get the actual scoring — earnings revisions, the PEG screen, momentum reads.

Six Themes: Where We Look for Ideas. The structural narratives that guide which segments of the market the portfolio wants exposure to. A theme isn't a sector — it cuts across them. You see what's on, what's off, and how each maps to the holdings.

Position Rationale: Decisions That Matter Most. How the framework translates into the actual portfolio today, position by position: why it's held, what job it does, how it scores, and what would change the thesis.

Macro Commentary: Growth, Inflation, Rates, Markets. The backdrop the portfolio is being managed against, with the underlying indicator tables — not market noise, the specific picture that informs the regime call.

Risks, Catalysts & the If/Then Playbook. What the desk is watching and how the portfolio would respond as conditions change — key risks ranked by severity, the 90-day catalyst calendar, and an explicit if this, then that playbook so the next move is decided in advance.

The Monthly Portfolio Update

Every month, for each strategy, a portfolio letter from the desk: the current regime read and what changed, what moved in the portfolio and why, the watchlist, the upcoming catalysts, and the updated if/then playbook.

It follows the same structure as the inaugural letter — regime, signals, themes, positioning, macro, risks, holdings — refreshed for the month. Brief by design, because the inaugural letter already did the heavy lifting.

Full Holdings & Weightings

You always see exactly what each portfolio holds and how much — every name, every weight, every framework score. No black box, no "trust us." The full engine, open for inspection.

Intra-Month Alerts

If something material happens between letters — a regime shift, a major catalyst, a position change — you hear about it when it happens, not at the end of the month.

Performance & Yield Reporting

Returns for the growth strategies; yield and income detail for Enhanced Income. The numbers, kept current.

*Important Disclosures: Street Sheet Strategies is published by The Street Sheet in partnership with DePaolo & May Strategic Wealth ("D&M"), an SEC-registered investment adviser. Registration does not imply a certain level of skill or training. Performance figures reflect the track record of model portfolios, presented gross of transaction costs and without deduction of any investment management or advisory fees; the track record is blended and includes an initial hypothetical period prior to live publication. Methodology and important limitations are described in the full disclosures which can be found on our website in our terms of service. Past performance is not indicative of future results. Investing involves risk, including possible loss of principal. Yields shown are trailing distributions and are not guaranteed. The Street Sheet is a publisher, not an investment adviser; subscribing does not create an advisory or fiduciary relationship with The Street Sheet or D&M, and nothing herein is individualized investment advice or a recommendation that any security or strategy is suitable for you. Your results will differ from the strategies shown. D&M, The Street Sheet, their affiliates, and D&M's clients hold positions in securities discussed and trade in them, including before publication, under the trade-sequencing policy described in the full disclosures. The Street Sheet also publishes paid advertisements and discloses them per Section 17(b) of the Securities Act of 1933. Consult your financial, tax, and legal advisers before investing. Full disclosures can be found .