Nine Chicago Startups Poised for Huge Growth in 2021

Rosalie MurphyLists

Millenium Park in Chicago. Editorial Credit: Luis Boucault, Shutterstock.

Chicago is the heart of the Midwest’s startup scene. Home to hundreds of companies, dozens of individual and institutional investors and thousands of passionate, driven employees, the Windy City has become a launchpad for startups solving not just user experience problems, but social problems too.

We’ve IDed nine early-stage startups that are poised for serious growth in 2021. They’ve all received major investment in 2020 — the kind of support that can transform young companies from small, scrappy startups into major players in their industries — or been welcomed into prestigious programs, like Google’s first-ever Black Founders Fund. That $5 million fund launched in June and has since invested up to $100,000 in more than 70 Black-owned startups around the country.

Most of these Chicago-based companies are still raising seed funding. A few have completed Series A rounds of up to $10.5 million. But they all have a lot of growing left to do. And in 2021, we think they’re positioned for quite a bit of it.


Marijuana is still regulated at the state and local levels, leaving a patchwork of rules that change every few hours as you drive cross-country. Fyllo’s Compliance Cloud offers a suite of enterprise-grade software powered by a database of those regulations. Whether you’re a local dispensary or a national marketing firm, Fyllo is designed to help you ensure your products and services are fully compliant. Keep in mind that Illinois legalized recreational marijuana at the beginning of 2020.

Investors have clearly recognized the need for this service. Fyllo raised a whopping $16 million in its September 2019 seed round from K2 & Associates and JW Asset Management. The same group of investors led Fyllo to a $10 million Series A raise in August.


From food trucks to beauty parlors to artists, CASHDROP allows merchants to set up a digital storefront in minutes so they can begin booking appointments and selling products and tickets. Founder Ruben Flores-Martinez developed the idea after watching dozens of small merchants turn to easy-to-use site creation tools but then get slammed with high transaction fees. On CASHDROP, merchants can set up quick, easy storefronts, and the platform takes no commissions on their sales. They charge buyers a 5% fee on purchases instead.

Incorporated in January, CASHDROP is the youngest company on this list. They announced a $2.7 million seed round in August, led by Harlem Capital. CASHDROP plans to use that funding to hire growth executives and content creators.


The CASHDROP app. Courtesy of CASHDROP on Facebook.


Medical research has historically excluded people of color, which is a problem both for the researchers creating medications and treatments and for the patients who will receive them. Drugviu is a population health platform, aiming to expand the data set by encouraging people of color to contribute to research that accelerates drug development and improves the diagnosing of autoimmune diseases.

A few months after its 2019 launch, Drugviu raised its first $200,000 through Chicago’s Techstars Impact Accelerator. San Francisco-based Right Side Capital Management invested an undisclosed amount in pre-seed funding in early 2020, and Drugviu is also part of Jumpstart Foundry’s 2020 portfolio — both signs of big things to come.

Five to Nine

This company seeks to help others understand how successful their employee engagement programs are. The enterprise SaaS platform helps companies manage initiatives like manager workshops, team-building events, and employee resource group gatherings while measuring the impact of those initiatives on culture, inclusion, and the bottom line.

Five to Nine started with $150,000 in pre-seed funding in 2018. A year later, the company raised $1 million in a seed round led by Chicago Early Growth Ventures. In 2020, Five to Nine was selected to the first-ever Google for Startups Black Founders Fund — alongside another Chicago company on this list, 4Degrees — which is sure to be catalytic.

Five to Nine Team

A few members of the Five to Nine leadership team, including CEO & co-founder Jasmine Shells. Image courtesy of Five to Nine on Facebook.

Bridge Money

Bridge wants to make banking better for everyone — and more equitable in the process. Targeting the 70 million unbanked and under-banked Americans, Bridge offers FDIC-insured bank accounts with no minimum balances and debit cards with no fees. They earn revenue by charging merchants a small fee instead of charging customers.

Another Chicago Early Growth Ventures company, Bridge announced its first $1 million seed raise at the end of March. Investors include Kapor Capital, Bread and Butter Ventures, Revolution’s Rise of the Rest Seed Fund, Ulu Ventures, and Acumen.


A self-styled “building experience app,” Cohesion offers a SaaS platform for everyone in a commercial building, including tenants, managers, and investors. The app integrates building hardware systems like HVAC and keycards, allows managers to communicate with tenants, and promises to deliver actionable insights to building owners.

Cohesion announced a $6.5 million seed round in June. Investors included Hyde Park Angels, Singapore-based Frasers Property Group CMT, and angel investors including Ken Griffin, Raj Gupta, and Michael Sacks.


This relationship management platform uses AI to identify users’ most important relationships, especially with clients, and to calculate the strength of those relationships. Companies in private equity, venture capital, and other relationship-driven industries have used 4Degrees as an advanced CRM to manage partners and clients alike.

4Degrees raised its first $1 million pre-seed round in 2017 with the help of Techstars Chicago. In 2020, Harlem Capital invested an undisclosed amount in seed funding. The company is also part of the Google Startups Black Founders Fund.


Leap is a venture-funded Chicago startup that has reversed the traditional retail model: Instead of starting in brick-and-mortar stores and then going digital, Leap helps companies do the opposite. Digital-native storefronts can hire Leap to help them develop in-person retail experiences as new marketing and sales channels.

Leap raised a $3 million seed round back in 2018. In February, they closed an additional venture round worth $10.5 million. Stay tuned for big strides in 2021.


A Leap client's storefront, Koio in Lincoln Park, Chicago.


NestEgg aims to make life easier for independent real estate investors. The platform allows landlords to automate and streamline key property management tasks, such as rent collection and lease renewals. Premium features include rent guarantees, in which NestEgg deposits money into users’ accounts even when renters miss their payments.

NestEgg launched in 2017 with just $100,000. Between January 2019 and March 2020 — just 15 months — the company raised $2,750,650 in two seed rounds. And despite the pandemic, they announced a $7 million Series A raise shortly before Thanksgiving, led by Hyde Park Venture Partners. NestEgg plans to use that funding to roughly triple the size of its staff, adding 40 more people next year.


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