The BOSS Sports

What The BOSS Sports does

The BOSS Sports operates a suite of three native consumer applications—BracketBOSS, PickemBOSS, and SquaresBOSS—available on iOS, Android, and Web for organizing and automatically scoring friendly sports prediction pools including March Madness brackets, NFL pick'em/survivor/confidence pools, Super Bowl squares, and World Cup brackets. The platform replaces spreadsheet-based pool management with a live real-time scoring engine that ingests third-party sports data and updates leaderboards instantly as scores change, supplemented by structural fairness features such as automatic pick locking at kickoff and cryptographic random number shuffling for squares board assignments. SquaresBOSS also includes Live Sports Bingo, a 5x5 self-dabbing prop card game, as an add-on module.

The company is a private, founder-operated business built and run by "Ricky" based in Chicago, bootstrapped with no external institutional funding disclosed. Revenue is derived from a freemium model: all core pool functionality is free, with monetization coming from one-time in-app purchases for ad removal and additional entries (processed by Apple App Store and Google Play) and from advertising on the free tier. Distribution is exclusively digital self-serve—Apple App Store, Google Play, and direct web access—with viral in-product growth driven by invite codes shared in group chats. No enterprise sales motion, no paid advertising, and no named B2B customers are present in the data.

Name

The BOSS Sports

Legal name

The BOSS Sports

Website

https://thebosssports.com

Company type

Private

Founded year

2026

Operating status

Operating

Headcount range

1–10 employees

Short description

The BOSS Sports builds native iOS, Android, and web apps (BracketBOSS, PickemBOSS, SquaresBOSS) that automatically score friendly sports prediction pools—brackets, pick'em, survivor, and squares—for social groups, family, and office pool commissioners using a freemium model.

Ownership category

akta.pro rank

Product category

Sports Pool Management Software

NAICS

Fitness and Recreational Sports Centers (71394)

SIC

Services-Miscellaneous Amusement & Recreation (7990)

akta.pro primary industry

Fantasy-to-Sportsbook Convergence (DFS Sportsbook Hybrids) (MPAEACAM)

Keywords

• Sports pool apps
• Bracket pool management
• Pick'em pool software
• Football squares pools
• NCAA bracket apps

Headquarters

HQ city

Chicago

HQ country

United States

HQ region

North America

Offices1 record

Markets served

GTM type

B2C

Offering type

Software

Cost components

Technology or R&D, Infrastructure, Personnel, Marketing or Sales, Operations

Revenue model

1. Freemium Core + Optional Upgrades: All BOSS apps are free to download and free to run a pool. Optional paid upgrades include removing ads and unlocking additional entries per player. These are one-time in-app purchases handled by Apple App Store or Google Play.
2. Advertising (Free Tier): Some apps show ads on the free tier. Ad partners may use device identifiers to serve and measure ads. A one-time in-app purchase to remove ads is available where offered.

Pricing tiers

Go-to-market motion1 record

Distribution channels4 records

Marketing channels5 records

Core offering

The BOSS Sports develops and distributes native iOS, Android, and web applications that let individual consumers create, run, and manage sports pools — specifically NCAA bracket pools, NFL pick'em pools, and NFL squares pools — directly from their phones. The apps replace spreadsheets, paper grids, and manual chasing of picks by automating pool setup, real-time scoring, automatic pick locking at game start, and (for squares pools) cryptographic fair shuffling of numbers. The portfolio spans three apps: BracketBOSS, PickemBOSS, and SquaresBOSS.

Product overview

The BOSS Sports Pool Suite is a family of three native apps (iOS, Android, and Web) for organizing and scoring friendly sports prediction pools. The suite comprises BracketBOSS (bracket pools for knockout tournaments), PickemBOSS (weekly pick'em, confidence, and survivor pools for season-long play), and SquaresBOSS (10x10 grid squares pools for single games). All three apps share a common philosophy of live scoring, automatic pick locking at kickoff, and invite-code-based joining. SquaresBOSS also includes Live Sports Bingo as an additional game mode.

Differentiator

Problem solved

Functional benefit

Brands

• BracketBOSS: Bracket Pool Manager - Single-elimination bracket pools for March Madness, playoff brackets, and seeded knockout tournaments with live scoring and real-time leaderboards.
• PickemBOSS
• SquaresBOSS

Products and services

• BracketBOSS

Quantifiable outcome

• Standings update instantly when scores change — no refresh, no math, no waiting for Monday

Segments4 records

Ideal customer profiles1 record

Technology focussed Yes

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Feature8 records

Partnerships

Three partnerships are on record, tiered core.

• Google FirebasecoreTechnology or IntegrationGoogle Firebase handles authentication (user account sign-in) and data storage for the BOSS Sports app family. Authentication is handled by Google Firebase as stated in the Privacy Policy. This is a critical infrastructure dependency for account management and data persistence across all three apps.
• Apple App StorecoreChannel Partner/ Reseller/ DistributorAll three BOSS Sports apps (BracketBOSS, PickemBOSS, SquaresBOSS) are distributed through the Apple App Store. In-app purchases for ad removal and additional entries are processed by Apple under their App Store policies, including their refund policies.
• Google PlaycoreChannel Partner/ Reseller/ DistributorAndroid versions of all three apps are distributed through Google Play. In-app purchases are handled by Google and subject to their refund policies.

Scale indicators1 record

Recent moves3 records

Expansion highlights5 records

Direct peers

• RunYourPool: Long-running online service for running NFL, college football, and March Madness office pools. Closest direct competitor with overlapping product surface (squares, pick'em, survivor) and identical customer persona (office and social pool organizers).
• OfficePoolStop: Office pool management website for NFL pick'em, March Madness brackets, and Survivor pools. Direct competitor targeting the same social/office pool commissioner persona with comparable functionality.
• PrintYourBrackets: Printable and online NCAA bracket templates for March Madness and tournament pools. Direct competitor for casual single-elimination bracket participants who prefer zero-friction free options.

Emerging players

• Sleeper: Mobile-first social fantasy sports app popular with younger users, offering chat-driven league management and pick'em formats. Comparable target user (social sports pool participants) but with deeper, more advanced league features and broader fantasy product scope.
• Underdog Fantasy: Mobile-first DFS operator offering best ball and pick'em formats. Comparable in mobile-first pick'em experience and target user, but processes real-money entries in regulated states, giving it a far larger monetization ceiling.
• PrizePicks: DFS operator focused on player-prop pick'em entries. Comparable in mobile-first sports prediction format, but PrizePicks is real-money while BOSS explicitly does not process wagers.

Broad incumbents

• ESPN Fantasy: Disney-owned incumbent fantasy sports platform supporting brackets, pick'em, and survivor formats for NFL, NBA, and college sports. Massive established audience and broad media portfolio overlap with BOSS's sports pool formats.
• Yahoo Fantasy: Incumbent free fantasy sports platform covering NFL, NBA, MLB, and tournament brackets. Competes directly for bracket and pick'em pool participation but operates as part of a much broader sports media portfolio.
• CBS Sports Fantasy: Paramount-owned incumbent fantasy sports platform with bracket, pick'em, and survivor formats. Overlaps with BOSS in bracket pool and pick'em use cases but sits within a broader sports media and broadcasting portfolio.
• FanDuel: Flutter-owned incumbent DFS and sportsbook operator offering pick'em, survivor, and bracket-adjacent formats. Overlaps on sports prediction pool formats but operates real-money gaming at scale and competes largely on different monetization mechanics.

Market position

Strengths4 records

Weaknesses4 records

Competitive moat5 records

Key risks6 records

Key highlights6 records

Customer concentration

Compliance1 record

Revenue estimate

Valuation estimate

Number of profiles

Profiles1 record

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about The BOSS Sports