FoodBoss
Chicago, US · 1 known investors
The page presents restaurant listings, including MAD Social (American cuisine in Chicago's West Loop, offering delivery and carry out) and JoJo's Shake Bar (known for heavily garnished shakes). It appears to serve diners in the Chicago area looking for dining, delivery, or carry-out options.
Also known as Bootler
Founders & leadership
Investors · 1
Company profile
researched Aug 2026FoodBoss is a Chicago-based food delivery search and comparison engine. The service aggregates listings from multiple third-party delivery platforms and from restaurants that operate their own ordering and delivery, and compares delivery fees, order minimums and estimated delivery times for the same restaurant across those providers so that a consumer can select the cheapest or fastest option. Users can search by address, restaurant name or cuisine type. The company describes itself explicitly as not being a food delivery company, and its positioning has been summarized as a Kayak-style metasearch layer for food delivery.
Founded in 2016 and originally operating as Bootler, the company rebranded to FoodBoss in summer 2018. It offers both a website and a mobile app, and at the time of its 2019 funding round it covered roughly 50 US cities and aggregated information from more than 50,000 restaurants. Alongside the search product, FoodBoss runs an editorial site (Experience FoodBoss) publishing restaurant round-ups, local dining guides and articles on food delivery economics and restaurant marketing.
Founding story
According to the company's own account, the idea arose when a founder tried to order food for a group of friends and found the process complicated by the number of competing delivery apps, each with different fee structures, restaurant selections, delivery time estimates and promotional offers. The conclusion was that there should be a single place to compare all of that information — described internally as "like Kayak for flights, but for food delivery" — which led to the launch of the service as Bootler.
Business model
FoodBoss operates as an aggregator and comparison layer on top of third-party food delivery services rather than as a delivery operator itself. It integrates data from partner delivery platforms and restaurants with in-house ordering, presenting fee and timing comparisons to consumers who then place an order through the chosen provider. Because the product depends on data supplied by partner delivery services, coverage is limited to those partners; at the time of its 2019 funding round the company had integrations with four services (UberEats, Postmates, Caviar and Delivery.com) and did not include DoorDash, Grubhub or smaller regional delivery operators.
Traction
As of March 2019 the service covered roughly 50 US cities and aggregated data from over 50,000 restaurants, with four integrated delivery partners. The company reported a growing user base ahead of its 2019 round, subsequent team expansion and a move to larger offices, and increasing media mentions.
▸Full profile — market position, technology, go-to-market, geography, history, risks & controversies
Market position
FoodBoss sits in the food delivery metasearch niche within restaurant technology, adjacent to but distinct from the delivery marketplaces it aggregates. Its relevance rests on the fragmentation of the delivery market across many providers with differing fees; commentators have noted that incomplete partner coverage and dependence on partner-supplied data are structural constraints on the model.
Rather than competing with delivery providers on logistics, FoodBoss positions itself as a neutral price and speed comparison layer across several delivery apps, surfacing the differing fee structures, restaurant availability and time estimates that consumers otherwise have to check app by app. It also indexes restaurants that run their own in-house ordering and delivery, not only third-party marketplaces.
Technology
A consumer-facing web and mobile app that aggregates live data from partner delivery services and restaurant ordering systems, indexing restaurants and returning comparable delivery fees, order minimums and live estimated delivery times, searchable by address, restaurant or cuisine.
Go-to-market
The company reaches consumers directly through its website and mobile app, supported by search-oriented editorial content on its Experience FoodBoss blog covering local restaurants, cuisine guides and delivery-cost explainers, along with media coverage of the service.
Consumers ordering restaurant food for delivery or carry-out who want to compare delivery fees, order minimums and wait times across delivery apps.
Geography
Headquartered in Chicago, Illinois, with coverage of over 50 cities across the United States as of 2019-2020; editorial coverage spans US metros including Chicago, New York, Kansas City, Indianapolis and Atlanta-area locations.
History
The company launched under the name Bootler, running an initial beta period before going live with delivery fee and time comparisons from its partner services. In summer 2018 Bootler re-branded as FoodBoss and introduced a redesigned website. In March 2019 the company raised more than $2 million led by Cleveland Avenue and used the capital to expand into additional cities, add features to its site and mobile app, grow the team and move into new office space. The company also publishes a consumer-facing content site, Experience FoodBoss, with restaurant and local dining guides for cities including Chicago, New York, Kansas City and Indianapolis.
Risks & controversies
Press coverage of the 2019 round identified two principal risks: incomplete coverage, since the comparison set at the time excluded major providers such as DoorDash and Grubhub as well as smaller regional delivery services, meaning users did not see every available option; and dependence on delivery partners for data, since a partner that objected to its rankings could cut off access and undermine the product's usefulness.
Compiled by commissioned research from 8 cited public sources — announcements, filings, and press listed under research sources below.
Key figures
latest reportedCompany-reported or press-reported figures, each dated to when it was claimed — not independently audited.
Competitors · 8
by search overlap
Companies competing with FoodBoss for the same Google search keywords, organic and paid, via search-intersection analysis.
Timeline · 3
launches, deals, and filingsFoodBoss announced a venture round of more than $2 million led by Cleveland Avenue, the food-focused venture capital firm founded by former McDonald's CEO Don Thompson. The company said it would use the funds to expand to more cities.
$2M source ↗
Following the 2019 funding round, the company added features to its website and mobile app, expanded its team and moved into new office space.
In summer 2018 the company, originally launched as Bootler, re-branded as FoodBoss and launched a new website design.
Dated company events from announcements, filings, and press; legal rows summarize public dockets and regulator releases.
In the news
▸Research sources · 8
primary sources listed
- What is FoodBoss? | The Food Delivery Search Comparison Engineexperience.foodboss.com · web
8 public sources were cited for this profile; the first-party ones are listed here.
Frequently asked questions
- What does FoodBoss do?
- Chicago-based search engine that compares food delivery fees and delivery times across multiple delivery apps.
- Who founded FoodBoss?
- FoodBoss was founded by Michael DiBenedetto, Mark Farnham.
- Who are FoodBoss's investors?
- FoodBoss's investors include Cleveland Avenue.
- Where is FoodBoss headquartered?
- FoodBoss is headquartered in Chicago, US.