Toll Booth Trading
About

About Toll Booth Trading

For people that like the idea of generating income from covered calls without the time or interest to do it manually.

Overview

Toll Booth is a trading bot for generating income from existing stock portfolios by selling covered call options. It is designed for retail investors with established ($100k+) portfolios who want incremental income without significant time investment. The platform abstracts the complexity of options trading—no need to manually open, roll, or close every position—while still giving you control over how and whether positions are opened, rolled, or closed.

Platform Compatibility

Currently supports Charles Schwab accounts, with Tastytrade support planned in the near future. Covered call trading is allowed on regular and retirement accounts. Be sure to enable covered options trading approval with Schwab before connecting to Toll Booth.

Covered Calls

A covered call involves holding a long stock or ETF position while selling a call option on the same asset, collecting premium for additional income. Managing positions manually can be time-consuming—Toll Booth automates the workflow while preserving your ability to set high‑level controls.

How and why covered calls can be tax efficient

  • Tax‑advantaged accounts: Premiums and assignments occur inside IRAs/401(k)s, so gains can compound tax‑deferred (Traditional) or tax‑free (Roth), subject to account rules.
  • Defers realizing stock gains: Covered calls can generate cash flow without immediately selling appreciated shares. If assignment occurs, the option premium is included in your stock sale proceeds; if the option expires, the premium is recognized in the current year.
  • Fewer forced sales: Conservative, out‑of‑the‑money strikes and dividend‑aware rolls aim to reduce early assignment, helping preserve long holding periods when desired.

Tax treatment depends on your situation and jurisdiction and may change. This is not tax advice. See Legal and consult a qualified tax professional.

Covered Calls 101

A covered call pairs shares you already own with a short call option on the same symbol to collect option premium for income.

When it’s a fit

  • Own ≥100 shares per symbol
  • Income focus with willingness to cap some upside
  • Sideways to modestly up market outlook

Key risks

  • Upside is capped above the strike price
  • Assignment risk if price is at or above the strike at expiration
  • Early assignment risk near ex‑dividend dates
  • Borrow/liquidity constraints can affect pricing and execution

Simple example

  • Own 100 XYZ at $50; sell 55C for $120
  • If XYZ ≤ 55 at expiration: keep shares and keep the $120 premium
  • If XYZ ≥ 55 at expiration: shares called away at $55; gain from 50→55 plus $120 premium
  • Breakeven ≈ $48.80 (($50 * 100) − $120)

Mini glossary

  • Premium — cash received for selling the option
  • Strike — the price where shares may be sold if assigned
  • Expiration — date when the option expires
  • Assignment — shares are called away at the strike

Tax treatment depends on your situation and jurisdiction and may change. This is not tax advice. See Legal and consult a qualified tax professional.

Learn more: Selection & Pricing • Opening • Closing • Rolling • Covered Call Life Cycle examples

How it works

Toll Booth automates the covered‑call lifecycle to turn your existing shares into consistent income while reducing busywork: it finds opportunities to open positions, manages exits to lock in gains or protect downside, and rolls positions to extend income streams while aiming to keep your shares or maximize returns, based on your investment priorities.

  • Opening: Screens symbols you own and sells conservative, out‑of‑the‑money calls to harvest premium within your risk guardrails.
  • Selection & Pricing: How the best covered‑call chain is selected and priced for opening orders.
  • Closing: Takes profits at configurable targets or risk events to realize premium and reduce exposure.
  • Rolling: Proactively extends duration or improves strikes to continue income generation and increase odds of keeping shares.

Compliance & Security Reassurance

  • Schwab OAuth: You sign in at Schwab; we never see or store your Schwab username/password.
  • Permissions and control: We request only what’s needed to read positions and place covered‑call orders you enable; no money movement. You can pause or disable trading at any time.
  • Tokenized access: Server‑side access/refresh tokens are stored securely and rotated; you can revoke access from your Schwab Security Center or within Toll Booth.
  • Transport & least privilege: All traffic uses TLS. Systems and credentials follow the principle of least privilege.
  • Data handling: Logs avoid account numbers and minimize PII; operational logs are scoped for troubleshooting. See Legal for details.

Other Trading Instruments

At this time, Toll Booth only places orders for covered call positions. Support for equities and other option strategies may be considered in the future.