# FoodBoss

> FoodBoss is a Chicago consumer search company that gathers restaurant ordering options in one place so diners can compare delivery fees, estimated times, pickup choices, and restaurant-direct ordering before leaving to complete a purchase. Founded in 2016 by Michael DiBenedetto and Liam Hession, the business began as Bootler, raised a publicly disclosed $2 million-plus seed round led by Cleveland Avenue, expanded into rewards and direct ordering discovery, and now sits in the awkward but useful layer between restaurants, delivery marketplaces, and hungry customers.

- **Founded:** 2016
- **Headquarters:** Chicago, United States
- **Founders:** Michael DiBenedetto (CEO and Co-Founder), Liam Hession (CTO and Co-Founder)
- **Team size:** 11-50 employees on LinkedIn; the supplied company record lists 17 employees
- **Products:** FoodBoss Search, Restaurant Direct, FoodBoss Rewards, Toast Integration
- **Notable:** Rebranded from Bootler to FoodBoss in summer 2018 after an initial beta period., Raised more than $2 million in a 2019 seed-plus round led by Cleveland Avenue., Expanded from third-party delivery comparisons to restaurant-direct ordering discovery in 2020.

## Products & services

- **FoodBoss Search** — A web and mobile comparison engine for restaurant delivery and pickup options, including estimated fees and delivery times.
- **Restaurant Direct** — A discovery feature that adds restaurants' own online ordering channels beside third-party delivery services.
- **FoodBoss Rewards** — A free app-based points program that rewards enrollment, logins, and orders completed through available ordering options.
- **Toast Integration** — A read-only integration that lets eligible Toast restaurants expose Toast Online ordering inside FoodBoss comparison results.

## Achievements

- Rebranded from Bootler to FoodBoss in summer 2018 after an initial beta period.
- Raised more than $2 million in a 2019 seed-plus round led by Cleveland Avenue.
- Expanded from third-party delivery comparisons to restaurant-direct ordering discovery in 2020.
- Received U.S. patents 10,445,683 in 2019 and 11,037,090 in 2021 for aggregation and presentation methods; a federal court held the asserted claims invalid in 2025 litigation.
- Reached a stated catalog of more than 250,000 restaurants across more than 60 U.S. cities in its App Store listing.
- Maintained a 4.5 rating from 424 ratings on Apple's U.S. App Store at the time of research.
- Added a restaurant-facing Toast integration documented in 2026.

## Latest updates

- **2023-09** — Apple's version history lists FoodBoss Rewards, new locations, and bug fixes in version 1.9.10.
- **2024-05** — Bootler, LLC d/b/a FoodBoss sued Google in federal court, alleging patent infringement and federal and Illinois antitrust violations related to Google Food.
- **2025-09** — A federal judge granted Google's motion to dismiss, finding the asserted patent claims ineligible and the antitrust injury insufficiently pleaded; FoodBoss was allowed time to amend.
- **2026-04** — Toast published support documentation for enabling a FoodBoss partner integration that exposes Toast Online ordering options in FoodBoss.

## Links

- Website: https://foodboss.com
- LinkedIn: https://www.linkedin.com/company/foodboss1
- Twitter/X: https://x.com/gofoodboss
- YouTube: https://www.youtube.com/watch?v=90kPP1fz2Lk
- Facebook: https://www.facebook.com/gofoodboss/

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Profile page: https://yespress.io/foodboss
Published by YesPress — https://yespress.io
Last updated: 2026-08-22