DePaolo & May Strategic Wealth

DePaolo & May Strategic Wealth Bespoke financial planning and investment management. We grow and protect wealth for successful families, entrepreneurs, and young high earners.

The rate your bank quotes you isn’t the cost of money. It’s the cost of money plus their cut.There’s a way around the ma...
05/31/2026

The rate your bank quotes you isn’t the cost of money. It’s the cost of money plus their cut.

There’s a way around the markup — one institutions have used quietly for decades.

It’s called a box spread loan. You borrow against your portfolio at a rate that tracks the risk-free curve — recently ~4%, versus the 6–13% on a typical bank securities-backed line or margin account.

Why it’s different:

➡️ You borrow straight from the listed options market — no bank balance sheet, no markup
➡️ Every trade clears through the OCC, the same clearinghouse that’s run since before 1987
➡️ Nothing gets sold — no capital-gains hit, and your investments stay invested
➡️ The cost is even treated as a capital loss under IRS Section 1256, not interest

To be clear: we’re not a lender. We advise on whether this strategy fits, size it against the right cushion, and coordinate the tax treatment. The loan itself is executed through your custodian (like Schwab) and the options market.

Full breakdown on our Insights hub — link in bio.

Investing involves risk including possible loss of principal. Securities-backed borrowing carries the risk of a margin call. DePaolo & May Strategic Wealth is an investment adviser, not a bank or lender, and does not originate or fund loans.

Educational only — not investment, tax, or legal advice. See full disclosures on our site.

📊 EARNINGS SEASON UPDATE 🔥Markets are making all-time highs despite continued back and forth on political headlines. Why...
05/11/2026

📊 EARNINGS SEASON UPDATE 🔥
Markets are making all-time highs despite continued back and forth on political headlines. Why? Earnings. Companies are massively beating estimates, raising forward guidance, and seeing huge margin expansion. Earnings growth is the highest it’s been since 2021. The AI-fueled boom continues.

Be sure to follow us for more market updates.

Thanks to our research provider FactSet for the great data as always.

🏆 Honored to be named one of the Top 25 Financial Advisory Firms — Rising Stars in the country by USA Today & Statista f...
04/16/2026

🏆 Honored to be named one of the Top 25 Financial Advisory Firms — Rising Stars in the country by USA Today & Statista for 2026.

This award reflects what we’ve been building from day one: a modern, independent firm that always puts clients first.

No outdated constraints, no big-firm product bias — just a relentless focus on doing what’s best for clients and providing real solutions.

Thank you to every client who trusted us to manage their wealth. You’ve all helped us achieve this recognition.

Cheers! 🎉

🔗 View the full story / rankings at the link in our bio

Disclosure: The 2026 USA TODAY Best Financial Advisory Firms ranking is researched by Statista Inc. based on recommendations and AUM growth. Not indicative of future performance. Not an endorsement. No fee was paid to participate.

April 15 is coming. Here are 6 tax moves you still have time to make.✅ Claim the new $40K SALT deduction✅ Max your IRA b...
03/11/2026

April 15 is coming. Here are 6 tax moves you still have time to make.

✅ Claim the new $40K SALT deduction
✅ Max your IRA before the deadline ($7K limit)
✅ Use the Backdoor Roth if you earn too much to contribute directly
✅ Claim the new Senior deduction (up to $6K)
✅ Deduct your car loan interest and overtime
✅ Watch out for the IRS Dirty Dozen scams

Don’t leave money behind. Full breakdown at the link in bio.

The Iran conflict is dominating headlines. Here’s what it actually means for your money.📌 Oil prices spiked short-term, ...
03/03/2026

The Iran conflict is dominating headlines. Here’s what it actually means for your money.

📌 Oil prices spiked short-term, but the long-term setup could favor lower energy costs if the U.S. gains more influence over Middle Eastern production

📌 Geopolitical shocks almost never cause lasting market damage — history is firmly on the side of staying invested

📌 We see the full-year outlook as constructive once the dust settles, especially at current valuations

We’re staying disciplined and watching the data. That’s what works.

Full breakdown on our blog → link in bio

📊 Our 2026 Market Outlook just dropped - Here are some key themes for this year (link in bio).📈 US Resilience with growt...
01/12/2026

📊 Our 2026 Market Outlook just dropped - Here are some key themes for this year (link in bio).

📈 US Resilience with growth stronger than meets the eye. A jobless recovery continues alongside AI-powered productivity and regulatory/fiscal tailwinds.
🤖 Artificial Intelligence shifting from infrastructure build-out to real-world deployment, productivity, and enterprise adoption.
🏭 Made in America as reshoring, advanced manufacturing, and infrastructure investment become strategic priorities.
🛡️ Defense & Global Security driven by persistent geopolitical tension and accelerating modernization.
💵 Debasement reinforcing the role of real assets and scarce resources as long-term portfolio hedges.
🔄 The shift from government bonds to alternatives as investors seek diversification, and inflation resilience.
❤️ Make America Healthy Again as healthcare innovation and demographics support durable, long-cycle growth.

👉 Read the full 2026 Outlook with our economic review, market forecast, and thematic breakdown - link in bio.

Happy Thanksgiving from our families to yours! We’re grateful every day for the trust you place in us - our clients trul...
11/28/2025

Happy Thanksgiving from our families to yours! We’re grateful every day for the trust you place in us - our clients truly feel like family. Cheers to another great year ahead!

🚀 Ready to rethink how your mortgage moves when you move? Our latest blog dives into the concept of portable mortgages —...
11/17/2025

🚀 Ready to rethink how your mortgage moves when you move?

Our latest blog dives into the concept of portable mortgages — a game-changer in the U.S. housing market that could finally free homeowners from the “rate lock-in” trap.

🔑 Key takeaways:
• Keep your existing low rate when you buy a new home (yes, really).
• But it’s not without trade-offs — more moving parts, changing collateral, and potential cost shifts for new buyers.
• If widely adopted, it could ripple out to the mortgage-backed securities market, mortgage rates, and your homeowner strategy.

➡️ Read more — link in bio.

🔐 Unlocking Roth IRAs: Conversions & Backdoor Strategies High-earners often get shut out of direct Roth contributions, b...
11/12/2025

🔐 Unlocking Roth IRAs: Conversions & Backdoor Strategies

High-earners often get shut out of direct Roth contributions, but that doesn’t mean the Roth vehicle is off the table. In our latest blog we walk through how Roth conversions and Backdoor Roth IRAs can both serve as powerful tools in your tax-efficient, next-gen wealth plan. (Link in bio) 💥

✔️ Why it matters: tax-free growth, no RMDs, heirs receive tax-free assets.

📈 When it fits:
• Anticipating higher future tax rates → conversion might be the move.
• Earning too much for direct Roth contributions → use the backdoor.

⚠️ What to watch: pro-rata rules, conversion timing, tax brackets, five-year rule.

📊 Big picture: It’s not one or the other — it’s about how both fit into a broader strategy of tax-diversified buckets and legacy planning.

👉 Dive into the full article now and consider how these tactics might align with your family’s long-term blueprint for control, flexibility and tax-free growth. Link in our bio.

🚨 Fed Day Update 🚨 Today is the 5th time the Fed has cut rates with the S&P 500 at all-time highs. In all prior instance...
10/29/2025

🚨 Fed Day Update 🚨 Today is the 5th time the Fed has cut rates with the S&P 500 at all-time highs. In all prior instances, the S&P 500 was higher a year later with an average return of 20%. The worst one-year return was a 15% gain. (Source JPM).

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