Dr. Matthew Griffith

CEO. Faith, family, fitness. Quant-style wheel trader focused on income, structure, and long-term freedom.

[Dr. Matthew Griffith @drmattgriffith]

@jamesnt @TJTheWheelDeal That was before they discontinued the best cars ever built 😀

[Dr. Matthew Griffith @drmattgriffith]

@GregVance99 @Alice_MiaX Same exact issues.

[Dr. Matthew Griffith @drmattgriffith]

@lydiahallie I’m up to $7k in 14 days??? Something needs to change.

[Dr. Matthew Griffith @drmattgriffith]

@mikealfred Wait. I thought you are always supposed to be 70% cash. 💰

[Dr. Matthew Griffith @drmattgriffith]

@TJTheWheelDeal Hey TJ how are you handling your PYPL $45 short calls? I have $43s expiring March 6 and the delta ran to .8. Do you think it will retrace on this takeover/merger noise or rebase?

[Dr. Matthew Griffith @drmattgriffith]

@TJTheWheelDeal Huge opportunity. I’m trying not to time the bottom cuz the money will be made on the ride up 💪

[Dr. Matthew Griffith @drmattgriffith]

@TJTheWheelDeal I value your patience and that’s something I’ve been working on improving. The $10 scenario is a good reminder not to front-load size too early.

Thanks for the perspective, always helpful.

[Dr. Matthew Griffith @drmattgriffith]

@Alice_MiaX Very well, said one can easily build a long-term strategic portfolio and have a slice of capital utilized for high Beta plays if they need to scratch their itch

[Dr. Matthew Griffith @drmattgriffith]

Got it, that makes sense. Sounds like you’re deliberately walking the basis down and keeping it in option form rather than letting assignment happen yet.

Appreciate the clarification. I’m leaning a bit more toward letting mine resolve into assignment if it gets there, but helpful to see how you’re thinking about the incremental rolls toward 150. 👍

[Dr. Matthew Griffith @drmattgriffith]

@Alice_MiaX 🤣

[Dr. Matthew Griffith @drmattgriffith]

This is the most important advice that can be given right now. True compounders don't have a 2X SPY beta portfolio. The goal is to have a reasonable spy Beta, and extract a reproducible Alpha return through skill. Otherwise, you're riding the waves through peaks and valleys, which is unsustainable.

[Dr. Matthew Griffith @drmattgriffith]

This is really impressive, SCOTT what’s your long-term thesis on this? I know you’re retired now. Are you looking to get a certain amount of dividend as a percentage of capital invested in these types of stocks or ETFs or are you just looking for a specific goal as far as a monthly amount I’m just curious on how you carve out this sleeve in you’re overall framework of your buying holds and your wheel strategies. Appreciate your thoughts.

[Dr. Matthew Griffith @drmattgriffith]

@pdicarlotrader Well said 👊

[Dr. Matthew Griffith @drmattgriffith]

@srobo1_ I was actually considering starting a $100k position in this now. Would you still add at this point if you did not have exposure yet? I see much more upside.

[Dr. Matthew Griffith @drmattgriffith]

I’m curious how you plan to size these contracts in practice. Are you thinking in terms of incremental margin impact per position, for example roughly 3 to 5 percent of stress margin using low delta around 0.15, added opportunistically based on current margin load rather than a fixed monthly schedule. And structurally, do you expect this to remain purely short puts using portfolio margin, or do you see any role for directional long exposure as part of the backstop framework over time. I have not seen you add that yet, so I am interested in how you think about it.

[Dr. Matthew Griffith @drmattgriffith]

@TJTheWheelDeal 100%. Brokers track tax basis, not economic reality.

If you sell premium, your true cost basis changes every trade. Without real-time adjusted basis and wash sale awareness, you’re managing risk blind and reconciling later.

Portfolio margin alone isn’t enough.

[Dr. Matthew Griffith @drmattgriffith]

This is not a retirement math problem. It is a tax architecture and asset routing problem, and it is still very solvable from this point forward.

At $700k income, age 45, zero debt, and ~$8M+ in assets, the priority is not chasing returns. It is reducing tax drag, lowering concentration risk, and putting the right assets in the right vehicles so retirement becomes durable instead of fragile.

Here is a coherent way forward.
Increase 529 contributions relative to kids’ ages$100k across four kids is light given proximity to college. This is one of the few buckets with a hard timeline. Increasing contributions now while income is high removes future cash flow pressure later.
Reposition idle cash without losing liquidity$250k in cash can be moved into short-duration Treasuries such as SGOV. This preserves liquidity, earns yield, and avoids dead money while maintaining flexibility.
Fix IRA concentration risk using available toolsAn $800k IRA fully allocated to a Bitcoin proxy introduces unnecessary single-name and operational risk inside a tax-deferred wrapper. If the IRA is held at Interactive Brokers, spot Bitcoin and crypto purchases are available directly within the IRA. The majority of exposure can be shifted to spot, with proxy exposure capped below 20% as a tactical sleeve rather than a core position.
Stop treating the taxable account as a stock problem$5.2M in IBIT is directionally fine, but incomplete without tax planning. The key unlock here is controlling whenincome is taxed, not just how it is invested.
Form a charitable LLC as a tax-routing vehicleDuring peak earning years, donate up to 50% of AGI annually into a charitable LLC. This directly offsets current tax liability and converts high ordinary income into controlled, tax-advantaged capital.
The charitable LLC should:
Sit in a separate Interactive Brokers account
Be invested conservatively
Be treated as an operating capital base, not a spend account
Use loans instead of liquidationsRather than selling assets, the charitable LLC can make documented loans to acquire real estate, additional trust-held equities, or other long-duration assets. This keeps capital invested while preserving flexibility.

Tie life insurance into the system explicitlyThis is the connective tissue.
A bank-funded whole life policy with a distribution rider is not used for heirs. It is used to:
Collateralize loans taken from the charitable LLC, protecting the charity and satisfying lenders
Provide tax-free policy loans later to fund living expenses in retirement

Neutralize the charitable LLC at death, with the death benefit repaying outstanding loans and making the charity whole
Over time, this creates a closed loop:
Income is routed into the charitable LLC to reduce taxes
Assets are acquired via loans instead of sales

Retirement income is funded through policy loans rather than taxable distributions
The death benefit restores the charitable balance and settles obligations
Use this structure to manage RSUs intelligentlyThe $1M in RSUs is future taxable income. With the charitable LLC in place, RSUs can vest and be liquidated with immediate tax offset, removing forced timing risk and smoothing income spikes.
The takeaway

From here, the goal is not early retirement by withdrawal math. It is capital architecture:
Route income deliberately
Assign assets to the correct entities
Use debt strategically instead of selling
Reduce taxes now and in retirement

Preserve optionality
Done correctly, retirement becomes a byproduct of structure, not a bet on markets.