About
Why we built Toll Booth
We build automation tools for long-term investors who want to put their portfolios to work — without becoming full-time traders.
The Origins of Toll Booth
Toll Booth Trading began in 2021 as a passion project of founder Jeff Pieta. While exploring personal investment strategies with financial advisors, Jeff was introduced to managed covered call overlay strategies — an approach to generating income from existing stock holdings. What surprised him was how these strategies were actually executed: manual orders placed within rigid, one-size-fits-all structures.
As brokerage firms began making application programming interfaces available, Jeff saw an opportunity to apply automation to a traditionally manual process. Drawing on his experience building technology companies, he began developing a platform designed to improve the consistency, flexibility, and efficiency of covered call management.
Bridging the Gap in the Market
Most options trading bots were built for active traders who had the time and interest to test complex or speculative strategies. Jeff believed a different type of investor was being overlooked: individuals with substantial stock portfolios who were interested in generating covered call income but did not want to learn how to operate complicated trading software.
Toll Booth Trading was created to serve those investors by making covered call automation more accessible and easier to manage. What began as a solution to Jeff's own investment challenge soon revealed a broader need among investors seeking to generate income from assets they already owned.
Why "Toll Booth"?
The company's name comes from a childhood memory. While riding in the car with his parents, Jeff would watch them throw money at highway toll booths and say that one day he wanted to own a toll booth of his own.
Since this product exists for one purpose — generating income from otherwise underutilized assets — the name fits.
Our Mission
Most long-term investors who own quality stocks and want to sell covered calls face the same problem: doing it right is tedious. You have to watch prices, pick strikes, place orders, monitor fills, decide when to roll or close, and repeat — all on top of everything else you manage. One missed roll or stale order can give back the premium you just collected.
Toll Booth was built to remove that operational burden without removing your control. You set your priorities — which stocks to run, how aggressive to be, whether to roll — and the platform handles the ongoing workflow: finding opportunities, placing orders, and managing the position lifecycle automatically.
Our philosophy is conservative by design: out-of-the-money strikes, dividend-aware timing, and rolling logic that aims to keep your shares rather than sacrifice them — because the point is incremental income on a portfolio you already want to hold.
How the Platform Works
Toll Booth manages the full covered-call lifecycle — opening, selection & pricing, closing, and rolling — on the shares you already own. You configure your preferences once; the platform runs the workflow continuously.
New to covered calls? Learn More explains the strategy, how rolling works, and what to expect before you get started.
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.
Product Scope & Roadmap
What's live today: Automated covered call management on Charles Schwab accounts — opening, monitoring, closing, and rolling, with per-position configuration and a real-time performance dashboard.
Coming next: Tastytrade brokerage integration is in progress. Support for additional option strategies and equity instruments may be added as the platform matures.
The focus is depth over breadth: we'd rather do covered calls exceptionally well than add instruments before they're ready.
Compliance & Security
- Schwab OAuth: You sign in at Schwab; we never see or store your Schwab username or password.
- Scoped permissions: 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 and refresh tokens are stored securely and rotated automatically. You can revoke access from your Schwab Security Center or from 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.
Under the Hood
For a deeper look at how the platform is built — reactive UI architecture, document-oriented data storage, job-queue automation, and token-based brokerage integration — see the full technical overview on the blog.