STQ is a modern investment advisory firm focused on tax-aware investment strategies, institutional-quality portfolio construction, and a conflict-free fiduciary model.
Institutional Depth. Personal Focus.
We build each portfolio from the ground up – optimizing assets, accounts, and vehicles to maximize what you keep after tax.
At STQ, our portfolio construction process starts with asset allocation – the long-term blueprint of what to own, how much, and why. We build it around your full financial picture: your income, your real estate, your business interests, your estate plan. And we keep it dynamic as markets evolve.
From there, we determine where each asset lives. A private equity fund in a taxable account generates gains and distributions taxed at your highest rate. The same fund in a tax-deferred account compounds untouched for decades. The investment is identical. The outcome is not. Getting placement right is one of the highest-value decisions in portfolio management – and one of the most overlooked.
Finally, we select the vehicle. How an investment is held has real tax consequences. We choose the structure that minimizes taxable events and maximizes after-tax compounding for your specific situation.
Your portfolio is a bank. Box spread borrowing lets you use it like one.
Most investors don’t realize their portfolio can function as a source of liquidity – without selling a single position. Box spreads are a four-leg options structure on a broad index that create a fully hedged position with a known payoff at expiration. The difference between what you collect today and what you owe at expiration is, effectively, the interest rate – set by the market, not a bank, and typically close to Treasury rates.
The result: access to capital at competitive rates, with no credit check, no bank approval, and no forced selling of appreciated positions. The interest is potentially tax-deductible, and your portfolio stays fully invested throughout.
At STQ, we implement synthetic borrowing through established institutional platforms – giving you access to a tool that most advisors can’t execute.
Index exposure with a tax engine built in.
Direct indexing means owning the individual securities that make up an index – rather than a fund that holds them for you. The result is a portfolio that tracks your target exposure while giving you the ability to harvest losses at the individual security level, customize holdings around existing positions, and exclude specific sectors or companies you don’t want to own.
The tax advantage is significant. Because you own individual securities rather than a fund, you can harvest losses on positions that decline even when the broader index is up. Individual stocks move independently – creating a continuous harvesting opportunity that a comparable ETF strategy simply can’t replicate. Those harvested losses can be used to offset gains anywhere in your portfolio: a real estate sale, a business exit, an RSU vest.
At STQ, we implement direct indexing through institutional-grade separately managed accounts – giving you the benefits of index-like diversification with the tax efficiency of individual ownership.
Turn volatility into a tax advantage without changing your strategy.
Tax-loss harvesting turns market volatility into a tax advantage – strategically realizing losses to offset capital gains and reduce your tax bill, without disrupting your long-term investment strategy. Done well, it’s not a one-time year-end exercise. It’s an ongoing process that compounds in value over time.
Think of it as a loss bank. Every time a position dips below your cost basis, we harvest that loss and deposit it. Those banked losses don’t expire. They sit there, accumulating, ready to be deployed against gains whenever you need them – a real estate sale, a business exit, a concentrated stock position, an RSU vest, a private equity distribution. The bank grows quietly in the background until the moment you need it most.
At STQ, we go beyond standard harvesting. We use advanced long-short strategies that continuously generate losses regardless of market direction – creating a richer opportunity set that a traditional long-only portfolio simply can’t match. The earlier you start building the bank, the more powerful the tool becomes.
You can’t just sell. But you can’t just hold either.
A concentrated position – whether from company stock, RSUs, a business sale, or an inheritance – is both an asset and a risk. The upside is real. So is the exposure. Managing it well requires balancing your desire to preserve upside, your need to diversify, and the tax cost of doing either. Move too fast and you hand a significant portion to the IRS. Move too slowly and a single bad quarter can erase years of gains.
At STQ, we build tailored strategies for each client’s situation. Options overlays can create meaningful downside protection without triggering a taxable sale. Systematic diversification over time can spread the tax impact across multiple years. Tax-loss harvesting elsewhere in the portfolio can offset gains realized on the position. Prepaid variable forwards allow you to monetize a concentrated position – receiving cash upfront while deferring the tax event – without an outright sale. And in the right circumstances, charitable vehicles can eliminate the tax burden entirely while funding causes that matter to you.
There is no one-size-fits-all answer to a concentrated position. There is only the right answer for you – and finding it requires looking at the full picture, not just the position itself.
Options don’t add risk. Properly structured, they remove it.
Options aren’t just for speculation. In the right hands, they’re precision instruments – one of the most powerful risk management tools available, and one of the most tax-efficient ways to adjust a portfolio without selling anything. Most investors never use them this way. Most advisors can’t execute them this way.
At STQ, we use options overlays to protect against significant downside, generate yield on existing positions, and reshape the return profile of a portfolio without triggering a taxable sale. Protective put spreads can cap your downside on a concentrated position. Cash-secured put writing can generate income on capital waiting to be deployed. Covered calls can monetize existing holdings without selling them outright. Every structure is evaluated through a tax lens first – because a hedge that creates a tax bill may not be worth putting on.
Options add precision, not complexity. Used correctly, they give your portfolio capabilities it simply wouldn’t otherwise have – and they do it in a way that keeps the tax outcome firmly in view.
Private markets don’t move with public ones. That’s the point.
Public markets give you liquidity. They also give you correlation – the tendency for asset classes to move together when diversification would matter most. Alternatives may help address that. Private equity, private credit, venture, real estate, and hedge funds operate on different timelines and may not move in lockstep with your stock portfolio – though they involve meaningful risks including illiquidity and potential loss of principal, and past performance is not indicative of future results.
Alternatives are also among the most tax-inefficient investments when placed incorrectly. A fund generating ordinary income may belong in a tax-deferred account. A fund with long-term capital gain potential may be better suited to a taxable account. Getting placement wrong can erode a significant portion of the return before you ever see it.
At STQ, we evaluate and size alternative allocations as part of a unified portfolio strategy – with tax placement considered from the start, not as an afterthought.
Give more. Keep more. Owe less.
A donor-advised fund is one of the most powerful tax tools available to high earners – and one of the least used. You contribute assets to the DAF, take the full charitable deduction in the year of contribution, and then grant the funds to charities on your own timeline. The deduction is immediate. The giving can happen over years or decades.
The real power is in what you contribute. Donating appreciated stock directly to a DAF eliminates capital gains entirely – you deduct the full fair market value without ever paying tax on the gain. For someone holding a concentrated position, a large RSU vest, or a pending business sale, a DAF can dramatically reduce the tax bill while funding causes that matter to you.
At STQ, we integrate DAF strategy into your broader tax plan – sizing contributions to maximize deductions in high-income years, coordinating with tax-loss harvesting and Roth conversions, and ensuring your charitable giving is doing as much tax work as possible alongside the good it’s already doing.
Why we don't ignore tax structure.
Two portfolios. Same investments. Same gross return. One pays taxes annually on every gain and dividend. The other defers, optimizes, and compounds without interruption.
Curious what tax drag is costing you?
See What's Possible →Hypothetical growth of $1M over 30 years. 10% gross return; taxable assumes 37% combined tax rate applied annually. Illustrative only.
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Akiva Glazerson is the founder of STQ Capital. He brings a rare combination of institutional investment experience and quantitative expertise that anchors STQ's commitment to transparency, integrity, accountability, and excellence.
Prior to founding STQ, Akiva served as Head of Investment Risk at a $42B+ RIA. Before that, he worked in Portfolio Solutions and Quantitative Research at PIMCO, constructing and optimizing multi-asset portfolios for institutional clients. He also held roles at the Royal Bank of Canada, UBS, and Deutsche Bank, building deep experience across public markets, private assets, and derivatives.
Akiva holds a B.S. in Accounting from Yeshiva University – where he attended on a soccer scholarship – maintains FINRA Series 7, 63, and 65 licenses, and holds the CSRIC designation.
Born and raised in South Africa, Akiva is a Brazilian Jiu-Jitsu black belt, an avid cyclist, and an aviation enthusiast. He loves to travel – especially back to South Africa – and above all, enjoys time with his wife and two young daughters.
No outside ownership, no product quotas, no conflicts of interest. We answer to one party – you.
Open architecture, full transparency, fiduciary at all times. We don't build products or guide clients into anything that serves us.
Technology-forward operations, cutting-edge tax products, and strategies most advisors can't execute.
Every portfolio is tailored to your tax situation, income, liquidity, and objectives. No cookie cutters.
The diagnostic is free. What we find usually isn't.