Radar Companies Retail · Chicago
Radar · Retail in Chicago

Best Retail Companies in Chicago, United States

The 538 best Retail companies in Chicago, United States in 2026, ranked by funding and momentum. Funding, investors, founders, valuation, tech stack and live signals. Top: Groupon.

538companies tracked
$3.7Bdisclosed funding
2unicorns
141have raised

Ranked: Best Retail companies in Chicago

#CompanyDisclosed fundingLast roundEmployeesFounderTech stackPatents & IP focusRecent signals
1Groupon
Online marketplace offering deals on multi-category products and services
$950M185 mo ago1,582Eric Lefkofsky
Co-Founder
TurbopackSentryZendesk+351,437 patents
Online deal marketing analytics and personalized recommendation systems for e‑commerce
2ShipBob 🦄
Provider of e-commerce fulfillment solutions for direct-to-consumer brands
$333M59 mo ago1,338
1,338 → 1,665 (+24%) · sector median +17%
Dhruv Saxena
Co-Founder & CEO
WordPress Block EditorWordPressApple iCloud Mail+381 award
3GTI
Provider of health, and wellbeing products related to cannabis
$225M84 mo ago4,600
4,600 → 2,363 (-49%) · sector median +17%
DrupalApple iCloud MailPHP+264 patents
Modular, expandable portable shelter systems for temporary housing and emergency structures.
4Cameo 🦄
Online platform offering personalized video messages from celebrities
$191M18 mo ago301
301 → 353 (+17%) · sector median +17%
Martin Blencowe
Co-Founder
Apple iCloud MailGoogle WorkspaceGoogle Sign-in+29
5Raise
Online marketplace offering gift cards for cash
$140M15 mo ago74Apple iCloud MailGoogle WorkspaceMUI+19
6Provi
Operator of an online marketplace connecting alcohol buyers, distributors, and brands
$139M32 mo ago249Taylor Katzman
Founder & CEO
HubSpot CMS HubApple iCloud MailGoogle Workspace+26
7Verano
Provider of cannabis-based products for health and wellbeing
$120M63 mo ago3,780George Archos
Co-Founder
DrupalPHPAmazon Web Services+284 patents
Network security event monitoring and large-scale data scanning for alerts
8Cresco Labs
Brand & retailer of cannabis gummies, seeds, and other products
$104M92 mo ago2WordPressApple iCloud MailMySQL+217 patents
Cannabis extraction, oil purification/fractionation, and agricultural risk management analytics.
9Circana
Customer analytics solutions for brands and retailers
$100M180 mo ago6,400
6,400 → 6,219 (-3%) · sector median +17%
Kirk Perry
CEO
WixSentryApple iCloud Mail+27
10Cooler Screens
Developer of IoT enabled solution for the retail businesses
$100M68 mo ago7443 patents
AI-powered inventory, marketing, and advertising system for refrigerated retail storage containers
11PowerReviews
Cloud-based platform to generate insights on reviews
$91M67 mo ago121
121 → 81 (-33%) · sector median +17%
Mark Dillon
CEO
WordPressApple iCloud MailGoogle Workspace+3620 patents
E‑commerce product review generation, analysis, and dynamic summary tools for online retailers.
12Farmer's Fridge
Provider of food vending machines
$83M62 mo ago212
212 → 428 (+102%) · sector median +17%
Luke Saunders
Founder & CEO
ShopifyCart FunctionalityContentful+201 job opening · 2 awards
13Braintree
Payment gateway solutions
$69M164 mo ago183Brain
CEO
14ThreeKit
AR-based product visualization platform for the retail industry
$66M55 mo ago86Ben Houston
CTO & Founder
HubSpot CMS HubApple iCloud MailGoogle Workspace+221 partnership
15Revolution
Provider of cannabis based products for medicine
$63M46 mo ago110WordPressApple iCloud MailMySQL+2927 patents
Personalized digital health program platforms with interactive UI and safe passenger transport systems
16Tovala
Provider of connected smart ovens
$61M64 mo ago350David Rabie
Co-Founder & CEO
Amazon WebstoreCart FunctionalitySentry+412 patents
Smart kitchen appliance automation and optimized perishable food packaging solutions
17InContext Solutions
Provider of 3D virtual store platforms and retail execution solutions
$54M65 mo ago77
77 → 62 (-19%) · sector median +17%
Dave Rich
Chairman & CEO
Master SliderSlider RevolutionWordPress+2312 patents
Virtual reality retail visualization and 3D apparel scanning for e‑commerce
18Retale
Aggregator of offline flyers, coupons and catalogs
$45M122 mo ago120
19Sittercity
Marketplace platform for caregivers
$43M150 mo ago38ContentfulTailwind CSSEnvoy+12
20Black Buffalo
Internet first brand offering nicotine patches
$38M46 mo ago18Mark Hanson
President and Co-Founder
Shogun Page BuilderCart FunctionalityShopify+44
21Rheaply
SaaS-driven procurement management software
$35M14 mo ago71Garry Cooper
Co-Founder & CEO
WordPressApple iCloud MailGoogle Workspace+35
22Fooda
Provider of workplace food programs featuring pop-up restaurants and catering
$32M33 mo ago223Shane Jones
Co-Founder
DrupalApple iCloud MailMicrosoft 365+271 award
23Interior Define
Internet-first brand of custom made furniture
$26M53 mo ago79MagentoCart FunctionalitySkolengo+58
24Monica + Andy
Organic baby clothes, blankets, pajamas, and more for families
$26M48 mo ago58Brian Bloom
Co-Founder & CFO
ShopifyTailwind CSSAmazon Web Services+32
25ItemMaster
Cloud-based product content creation and management platform for the food and beverage marketplace
$25M98 mo ago75Simon Angove
CEO
26ShoppingGives
Provider of cashback management solutions for businesses
$24M47 mo ago47Ronny Sage
Founder & CEO
27Leaf Trade
A wholesale cannabis marketplace platform
$23M50 mo ago52Steve Weisman
Co-Founder & Chairman
WordPressMySQLPHP+23
28Crafty
Online B2B marketplace offering multi-category grocery products for offices
67Funding top 25%Growth top 26%Talent top 28%Innovation top 34%
All 10 signals ▾
Fundingtop 25%
Growthtop 26%
Talenttop 28%
Innovationtop 34%
Producttop 36%
Techtop 39%
Moattop 39%
Markettop 49%
Globalbottom 32%
Customersbottom 1%
Funding: Raised $21.6M across 8 rounds · 8 rounds over 8 yrs (1.0/yr)
Growth: Headcount 74 → 116 (+57%) across vintages · Fresh capital in last 24 mo
rank vs industry peers · Fliar Intelligence Index 67/100
$22M3 mo ago116
116 → 256 (+121%) · sector median +17%
Nathan Rosenstock
Co-Founder
WordPressMySQLPHP+291 launch
29LandscapeHub
Online marketplace for landscaping materials
$19M28 mo ago46Cart FunctionalityRubyVimeo+27
30SalonInteractive
Provider of online retail and marketing tools for beauty professionals
$17M29 mo ago21RubyErlangSalesforce+22
31Brideside
Platform for finding and buying wedding dresses
$14M73 mo ago110
32Goose
Provider of business management solutions for pet care platforms
$13M15 mo ago6WebflowRiveAmazon Web Services+231 job opening · 1 launch
33Venzee
Provider of product information management and content syndication platform
$13M47 mo ago32
34The 1937 Group
Brand of cannabis products
$13M45 mo ago13Ambrose Jackson
Chairman and CEO
Wix eCommerceWixSentry+12
35Purchasing Platform
Provider of software suite solutions for businesses
$13M43 mo ago41Dave Bowen
CEO
36Oars + Alps
Internet first brand offering beauty care products for men
$12M24 mo ago14Mia Saini Duchnowski
CEO and Co-Founder and Board of Director
Cart FunctionalityShopifySentry+571 award
37Pacas
Internet first brand offering socks for men, women and kids
$11M36 mo ago26Christian Arquilla
Co-Founder
Cart FunctionalityShopifyBugHerd+36
38Nurture Life
Internet first brand offering subscription based cooked meals for kids
$7M29 mo ago50
50 → 67 (+34%) · sector median +17%
Helen Revans
Founder of Nurture Your Life
Amazon WebstoreCart FunctionalityZoho+412 awards
39Coldcart
Provider of technology platform optimizing perishable parcel and eCommerce logistics
$6M23 mo agoAndrew Salamon
Co-Founder
40Listener Brands
Internet first brand offering hair care and styling products
$6M15 mo ago30Kim Lewis
Co-Founder
41Vibe IQ
Providing brands with go-to-market collaborative retail applications
$6M24 mo agoBrian Lindauer
Founder
WordPressMySQLPHP+258 patents
Interactive digital signage and personalized media delivery with liquid-activated illumination systems
42Pimly
Provider of product information management solutions for e-commerce businesses
$5M11 mo ago141 launch
43Public Rec
Internet first brand offering casual wear for men and women
$5M33 mo ago27ShopifySentryZendesk+39
44Tradepost
Operator of platform facilitating instant offers for various collectible items
$5M8 mo agoAlexander Perez
Co-Founder & CTO
Node.jsTypeScriptGraphQL+12
45Zenblen
Provider of tech-enabled smoothie bar
$3M10 mo ago10Tom Zhang
Founder & CEO
Cart FunctionalityWix eCommerceWix+14
46Neopenda
Provider of wearable neonatal signs monitor
16Moat top 38%Funding top 42%Tech top 43%Talent bottom 49%
All 12 signals ▾
Moattop 38%
Fundingtop 42%
Techtop 43%
Talentbottom 49%
Productbottom 47%
Growthbottom 43%
Globalbottom 37%
Innovationbottom 36%
Patentsbottom 25%
Marketbottom 22%
Fin. healthbottom 19%
Newsbottom 18%
Moat: Editorial + unicorn rating 7/10 · IP moat: 3 patents
Funding: Raised $2.7M across 12 rounds · 12 rounds over 8 yrs (1.5/yr)
rank vs industry peers · Fliar Intelligence Index 16/100
$3M1 mo ago14Teresa Cauvel
Co-founder and CTO
WixSentryBootstrap+143 patents
Wearable neonatal vital‑sign monitoring systems
1 job opening · 1 launch · 1 expansion
47Continuum
Provider of B2B automated returns software for wholesale organizations
$2M6 mo agoAlex Witcpalek
Founder & CEO
HubSpot CMS Hubcore-jsPreact+1413 patents
Patents concentrated in electrical & electronics
3 job openings
48IN BOLD PRINT
Provider of SaaS-based sustainability scoring platform on website for brands and retailers
$2M20 mo ago6Ashley Pradhan
Co-Founder & Co-CEO
49TrustClarity
Provider of SaaS-based excess inventory management solution
$300K14 mo ago5Sujee Jeganathan
Founder & CEO
Node.jsBootstrapExpress+192 patents
Patents concentrated in computing, sensing & instrumentation
1 job opening
50DUDE Wipes
Online platform offering personal hygiene wipes for men
$225K11 mo agoJeffrey Klimkowski
Co-Founder and CFO
Cart FunctionalityAmazon WebstoreShopify+28

Top 12 Retail companies in Chicago

#1
Series B · Chicago, Illinois · founded 2015 · 116 employees
$21.6Mraised

Online B2B marketplace offering multi-category grocery products for offices. It caters to offices to manage pantries, catering, cafes, etc. The product catalog includes hot coffee, cold brew coffee, kegs, craft beer, dry snacks, breakfasts, etc.

Fliar Intelligence Index™ 67how this company ranks against its industry peers
Funding
top 25%
Growth
top 26%
Talent
top 28%
Innovation
top 34%
Product
top 36%
Tech
top 39%
Funding: Raised $21.6M across 8 rounds · 8 rounds over 8 yrs (1.0/yr) · Last round Series B (Feb 2026)
Growth: Headcount 74 → 116 (+57%) across vintages · Fresh capital in last 24 mo
Talent: 3 named leaders on record · 3 C-suite/founder profiles curated
Audience (LinkedIn): 9k LinkedIn followers
Activity (LinkedIn): 1 product launches announced in 12 mo
Funding rounds
  • Feb 2026Series B$13.2M
  • Nov 2025Series A$1M
  • May 2024Series A$8.7M
  • Apr 2022Series A$10M
Founders & team
Nathan RosenstockCo-FounderIshan DayaCo-FounderJimmy PaulCo-Founder / CTO
Investors
Tribeca Venture Partners, OCA Ventures, Manifold Group, Greycroft, Firebrand Ventures, Gaingels
Tech stack
AdrollAdroll Cmp SystemAmazon ElbAmazon Web ServicesApache Http ServerApple Icloud Mail
#2
Seed · Chicago, Illinois · founded 2015 · 14 employees
$2.7Mraised

Provider of wearable neonatal signs monitor. The device is a small low-cost neonatal vital signs monitor integrated into a baby hat and uses a simple sensor array to measure heart rate, respiratory rate, blood oxygen saturation, and temperature. The sensors are powered by rechargeable batteries, and wirelessly transmit data to a central monitor which alerts attending healthcare professionals when a newborn is in immediate danger. It is intended for critically ill newborns being cared for in hospitals in low-resource countries such as Uganda.

Fliar Intelligence Index™ 16how this company ranks against its industry peers
Moat
top 38%
Funding
top 42%
Tech
top 43%
Talent
bottom 49%
Product
bottom 47%
Growth
bottom 43%
Moat: Editorial + unicorn rating 7/10 · IP moat: 3 patents
Funding: Raised $2.7M across 12 rounds · 12 rounds over 8 yrs (1.5/yr) · Last round Conventional Debt (Apr 2026)
Tech: 25 technologies across 5/8 capability areas · Cloud: Google Cloud, Google Cloud Cdn · Devops: Nginx
Audience (LinkedIn): 3k LinkedIn followers
Hiring (LinkedIn): 1 hiring post in 12 mo (public) · hiring: Head of Growth, Medical Research Officer
Activity (LinkedIn): 1 product launches · 1 expansions announced in 12 mo
Funding rounds
  • Apr 2026Conventional Debt$35K
  • Nov 2024Conventional Debt$200K
  • Sep 2022Conventional Debt$700K
  • Apr 2021Seed$1.4M
Founders & team
Teresa CauvelCo-founder and CTO
Investors
Axel Johnson, SUNU Capital, Assiduity Capital, Sorenson Impact Foundation, Villgro Africa, Connetic Ventures
Tech stack
BootstrapGodaddyGoogle CloudGoogle Cloud CdnGoogle WorkspaceGsap
#3
Series D · Chicago, Illinois · founded 2011 · 74 employees
$140.2Mraised

Online marketplace offering gift cards for cash. It allows users to sell gift cards from different brand and restaurant to get cash back. The user chooses the selling price and the gift card is featured on its for consumers to buy.

Funding rounds
  • Feb 2025Series D$63M
  • Sep 2017Series C$60M
  • Jun 2016Series B$818.3K
  • Jan 2015Series B$56M
Investors
Bessemer Venture Partners, Listen VC, Accel, PayPal, New Enterprise Associates, tpo.org
Tech stack
Amazon CloudfrontAmazon Web ServicesCloudflareCloudflare Bot ManagementCore-JsEnvoy
#4
Cameo 🦄
Series C · Chicago, Illinois · founded 2017 · 301 employees
$190.8Mraised

Online platform offering personalized video messages from celebrities. It enables users to book personalized video shoutouts from their favorite celebrities, sportsmen, influencers, and more. It also allows users to download videos and share them across their social media pages.

LinkedIn Pulse recent public activity · Jul 2026
Audience: 34k LinkedIn followers — 3.2% of this cohort's audience
Activity: 1 partnerships (incl. TikTok) announced in 12 mo
Funding rounds
  • Dec 2024Series C$2.9M
  • Mar 2024Series C$25.1M
  • Mar 2021Series C$100M
  • Jun 2019Series B$50M
Founders & team
Martin BlencoweCo-FounderDevon TownsendCo-Founder & Chief Product OfficerSteven GalanisCo-Founder & CEO
Investors
Kleiner Perkins, SPARK Ventures, Lightspeed Venture Partners, Bain Capital Ventures, TCG Ventures, Headline
Tech stack
Amazon CloudfrontAmazon S3Amazon Web ServicesApple Icloud MailBranchBraze
#5
Series B · Chicago, Illinois · founded 2016 · 71 employees
$35.5Mraised

SaaS-driven procurement management software. The company offers 'Rheaply AxM' - an online inventory management software, which enables organizations to lower procurement and storage costs and manage their assets. Features include automated listings, automated notification & messages, and automated reporting.

LinkedIn Pulse recent public activity · Jul 2026
Audience: 10k LinkedIn followers
Activity: 1 partnerships (incl. Wellstar Health System) announced in 12 mo
Funding rounds
  • Apr 2025Series B$1M
  • Mar 2023Series B$15.2K
  • Jun 2022Series B$20M
  • Dec 2021Grant (prize money)$100K
Founders & team
Garry CooperCo-Founder & CEOTyler SkeltonCo-Founder
Investors
HPA, Concentric Equity Partners, M25, Techstars, Revolution, PSP Partners
Tech stack
AddtoanyAddtoany Share ButtonsAmazon CloudfrontAmazon S3Amazon Web ServicesApple Icloud Mail
#6
Series A · Chicago, Illinois · founded 2024
$4.6Mraised

Operator of platform facilitating instant offers for various collectible items. The platform allows users to sell tickets, sports cards, trading cards, sealed wax, autographs, sneakers, vinyl, comic books, magazines, consoles, and video games. It also supports the sale of smartphones, handbags, designer clothes, streetwear, watches, laptops, Labubu, coins, Legos, jewelry, and vintage items. Furthermore, the platform facilitates transactions for books, eyewear, fine wine, stamps, bobbleheads, cars, domains, fine art, condos, and startups.

LinkedIn Pulse recent public activity · Jul 2026
Audience: 708 LinkedIn followers
Activity: 1 product launches announced in 12 mo
Funding rounds
  • Sep 2025Series A$4.6M
Founders & team
Alexander PerezCo-Founder & CTOTyler MozeleskiCo-Founder & CEO
Tech stack
Amazon Web ServicesApolloGraphqlHstsMailgunNext.Js
#7
Series A · Chicago, Illinois · founded 2023
$1.7Mraised

Provider of B2B automated returns software for wholesale organizations. It manages continuous transactions post purchase order for wholesale, distribution, and manufacturing organizations. It offer services such as touchless RMA automation, updates on return status, and integrations with business system.

LinkedIn Pulse recent public activity · Jul 2026
Audience: 8k LinkedIn followers
Hiring: 3 hiring posts in 12 mo (public) · momentum +3 · hiring: Head of Events & Associations, Business Development Representative
Funding rounds
  • Dec 2025Series A$7.2M
  • Nov 2024Seed$4.1M
  • Apr 2024Seed$1.7M
Founders & team
Alex WitcpalekFounder & CEO
Investors
Cowboy Ventures, M25, Clocktower Ventures, Cambrian Fintech
Tech stack
CloudflareCloudflare Bot ManagementCore-JsGoogle AnalyticsGoogle Font ApiHsts
#8
Series A · Chicago, Illinois · founded 2022 · 14 employees
$5Mraised

Provider of product information management solutions for e-commerce businesses. The solutions provided are real-time product information & image management, configurable digital catalogs, sell sheets, and more. The platform connects the sellers PIM to their Salesforce customer relationship management segment.

LinkedIn Pulse recent public activity · Jul 2026
Audience: 2k LinkedIn followers
Activity: 1 product launches announced in 12 mo
Funding rounds
  • Jul 2025Series A$2.3M
  • Sep 2022Series A$5M
Investors
High Alpha, HPA, Handshake Ventures, Slojo Investments
#9
Seed · Chicago, Illinois · founded 2021 · 6 employees
$13.4Mraised

Provider of business management solutions for pet care platforms

LinkedIn Pulse recent public activity · Jul 2026
Audience: 1k LinkedIn followers
Hiring: 1 hiring post in 12 mo (public) · hiring: Product Manager, Software Engineer
Activity: 2 product launches announced in 12 mo
Funding rounds
  • Feb 2025Seed$13.4M
Investors
B Capital, First Round Capital, 81 Collection, Imaginary, BoxGroup
Tech stack
Amazon CloudfrontAmazon S3Amazon SesAmazon Web ServicesCdnjsCloudflare
#10
Seed · Chicago, Illinois · founded 2018 · 10 employees
$2.8Mraised

Provider of tech-enabled smoothie bar. It enables users to order using the touchscreen interface and make payments.

LinkedIn Pulse recent public activity · Jul 2026
Audience: 941 LinkedIn followers
Hiring: 1 hiring post in 12 mo (public) · hiring: Manufacturing Engineer
Activity: 1 awards announced in 12 mo
Funding rounds
  • Aug 2025Seed$2.5M
  • Sep 2023Seed$2.8M
Founders & team
Tom ZhangFounder & CEO
#11
Deadpooled · Chicago, Illinois · founded 2015 · 30 employees
$6.4Mraised

Internet first brand offering hair care and styling products. Its product catalog includes shampoo, conditioner, styling cream, moisturizer, flaxseed gel, and serum. It also offers personalized recommendations based on hair type and condition.

Funding rounds
  • Feb 2025Series A$200K
  • Jun 2023Series A$1M
  • May 2023Series A$5M
  • Nov 2022Seed$450K
Founders & team
Kim LewisCo-Founder
Investors
Braintrustfoundersstudio
#12
Series C · Chicago, Illinois · founded 2015 · 249 employees
$138.8Mraised

Operator of an online marketplace connecting alcohol buyers, distributors, and brands. The platform provides tools for product discovery, communication, and order management. It offers a way for buyers to find products and connect with sales representatives. The platform also allows brands and distributors to showcase portfolios.

LinkedIn Pulse recent public activity · Jul 2026
Audience: 8k LinkedIn followers
Activity: 1 product launches · 2 partnerships · 1 awards (incl. Opici Family Distributing) announced in 12 mo
Funding rounds
  • Oct 2023Series C$32.5M
  • Sep 2021Series C$75M
  • 2021Series B$25M
  • May 2018Seed$4.8M
Founders & team
Taylor KatzmanFounder & CEO
Investors
Ludlow Ventures, Hyde Park Venture Partners, Sandalphon Capital, HPA, Gener8tor, Bessemer Venture Partners
Tech stack
Amazon Web ServicesApple Icloud MailChameleonCloudflareCloudflare Bot ManagementContentsquare

Funding & investor landscape

$3.7Btotal disclosed funding
136companies funded
353disclosed rounds
1rounds last 90 days
Most active investors
HPA12 rounds
Techstars10 rounds
Pritzker Group8 rounds
Service Provider Capital8 rounds
Chicago Ventures7 rounds
Hyde Park Venture Partners7 rounds
Lightbank7 rounds
Slojo Investments6 rounds
Listen VC5 rounds
Origin Ventures5 rounds

Notable founders

Nathan Rosenstock
Co-Founder · Crafty
Ishan Daya
Co-Founder · Crafty
Teresa Cauvel
Co-founder and CTO · Neopenda
Martin Blencowe
Co-Founder · Cameo
Devon Townsend
Co-Founder & Chief Product Officer · Cameo
Garry Cooper
Co-Founder & CEO · Rheaply
Tyler Skelton
Co-Founder · Rheaply
Alexander Perez
Co-Founder & CTO · Tradepost
Tyler Mozeleski
Co-Founder & CEO · Tradepost
Alex Witcpalek
Founder & CEO · Continuum
Tom Zhang
Founder & CEO · Zenblen
Kim Lewis
Co-Founder · Listener Brands
Prism market signals · United States · country-scoped Prism corpus, 13,857,502 docs

Market landscape — 10 sub-themes by coverage

Share of Retail coverage by sub-theme.

Regulatory-risk over time rising

Funding & growth over time

funding rising · growth rising

Common questions

How many Retail companies are there in Chicago, United States?
Radar tracks 538 indexable Retail companies headquartered in Chicago, United States that meet our profile-completeness bar.
What is the total funding raised by Retail companies in Chicago, United States?
The Retail companies in Chicago, United States on this list have raised a combined $3.7B in disclosed equity funding across 136 funded companies.
Which is the highest-funded Retail company in Chicago, United States?
Groupon is the highest-funded Retail company in Chicago, United States, with $950M in disclosed equity funding.
How many Retail companies in Chicago, United States are funded?
136 of the 538 Retail companies in Chicago, United States on this list have disclosed at least one equity funding round.
How many Retail unicorns are there in Chicago, United States?
2 Retail companies in Chicago, United States on this list are valued at $1B or more.
Who are the top investors in Chicago, United States Retail companies?
The most active investors in Chicago, United States Retail companies on this list include HPA, Techstars, Pritzker Group, Service Provider Capital, Chicago Ventures.
Riya SenguptaFinancials

Riya reads income statements for fun. She covers the real money in a sector — revenue, growth, who actually earns — and never met a vague claim she didn't want a number for.

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