Overview

What is Toll Booth

Toll Booth places orders for covered calls on shares you already own. It seeks to automate the covered-call lifecycle - scanning for opportunities, submitting orders, rolling positions, and closing - so you can pursue potential premium income without managing every order by hand. Outcomes depend on markets, your holdings, and how you configure the system; results will vary and involve risk.

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Who Toll Booth is for

Toll Booth is built for long-term investors who already own diversified stock or ETF portfolios and want to explore option-premium income from covered calls without becoming full-time options traders.

  • You have an established portfolio and want potential incremental cash flow without turning options into a second job.
  • You are comfortable with stock and ETF investing but would rather automate covered-call mechanics than manage every order manually.
  • You prefer conservative, rules-based automation over speculative option strategies.

Managing covered calls manually is a grind

Running covered calls across a real portfolio means constantly scanning for opportunities, sizing positions, placing tickets, watching fills, reacting to price moves, managing rolls, and closing positions when risk changes. Doing that symbol by symbol in a brokerage interface can consume hours every week or fall through the cracks when markets are volatile.

Toll Booth sits on top of your existing account as an automation layer for this operational work, applying the rules you configure while keeping you in control of which symbols are eligible and how positions are managed.

What Toll Booth does

Toll Booth aims to turn shares you already own into a potential source of option-premium cash flow by automating the covered-call lifecycle: it finds conservative opportunities, submits opening, rolling, and closing orders you enable, and monitors risk according to guardrails you configure.

The system focuses on covered calls rather than broad speculative strategies and is documented in more detail on the covered-call lifecycle pages:

  • Opening: Screens symbols you own and sells conservative, out-of-the-money calls within your risk guardrails.
  • Selection & Pricing: How Toll Booth evaluates chains and selects candidate strikes.
  • Closing: Takes profits at configurable targets or risk events to realize premium and reduce exposure.
  • Rolling: Proactively rolls positions to aim to extend premium capture and increase the odds of keeping shares when that aligns with your configuration.

How Toll Booth fits with your accounts

You connect an existing Charles Schwab account to Toll Booth using Schwab's OAuth sign-in. Toll Booth does not custody assets and never sees or stores your Schwab username or password. Once connected, the system can read positions and, when you enable trading, place covered-call orders within the permissions you approve.

Covered call trading is allowed on regular and retirement accounts that have covered-options approval with Schwab. You can pause or disable trading from Toll Booth or revoke access from your Schwab Security Center.

When you connect, you sign in directly at Schwab; Toll Booth never sees your Schwab password. Access relies on tokenized permissions that can be revoked from your Schwab Security Center or within Toll Booth, and the system cannot move cash in or out of your account. Tokens are stored securely and rotated, and access is limited to what is needed to read positions and place covered-call orders you enable.

What makes Toll Booth different

Toll Booth occupies a distinct role in a covered-call strategy. It is a software-only order routing and automation tool that runs on top of your existing brokerage account instead of pooling assets into a fund or managed account.

  • Your shares, your account: Unlike covered-call ETFs, your positions stay in your own Schwab account. Toll Booth sends orders; it does not take custody.
  • Per-symbol control: You choose which symbols are eligible, how aggressively they are used for covered calls, and when automation is enabled.
  • Automation, not advice: Toll Booth is not a broker-dealer or investment adviser. It follows rules you configure; you remain responsible for suitability, diversification, and overall portfolio management.
  • Conservative by design: The system focuses on conservative, out-of-the-money covered calls with guardrails and risk checks documented in the strategy guides.

Trusted by clients

What long-term investors say about Toll Booth Trading.

“Its like collecting rental income on a vacation home without the hassle.”

— V.S. , Client

Testimonial disclosure: Client status: client. Compensation: no. Source: Direct client statement.

“I like generating income from my concentrated positions and hedging downside risk.”

— E.L. , Client

Testimonial disclosure: Client status: client. Compensation: no. Source: Direct client statement.

“Since connecting my account last summer, the additional income generated from covered call premiums has exceeded my expectations.”

— P.S. , Client

Testimonial disclosure: Client status: client. Compensation: yes. Source: Direct client statement.

Testimonials may not be representative of the experience of other customers and are no guarantee of future performance or success. See Legal.

3 min
Typical signup time
Conservative
Covered call approach
Every trading day
Positions monitored and managed according to user preferences

Methodology and notes: View details

What Toll Booth is not

Toll Booth places covered-call orders on shares you already own - it does not open or close stock positions, purchase new shares, or recommend which securities to buy or sell. It does not move assets, transfer cash, or exercise discretion over your portfolio beyond the covered-call orders you enable.

It is not a financial adviser, broker-dealer, or portfolio manager. It follows the rules you configure and cannot assess whether those rules are suitable for your individual circumstances. Outcomes depend on market conditions, your holdings, configuration choices, and tax situation. This overview is for informational purposes and is not investment, tax, or legal advice. Options involve risk and are not suitable for all investors. See the Legal and Performance Disclosures pages for important risk and performance information.

  • No withdrawal or transfer access
  • Schwab‑approved API connection
  • Your credentials stay with Schwab
  • US‑based · Schwab accounts only
Risk disclosure: Options involve risk and are not suitable for all investors. Outcomes depend on markets, configuration, and individual circumstances, and results will vary. Nothing on this page is investment, tax, or legal advice. See Legal and Performance Disclosures.