Fifth Star Funds
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Portfolio

Twenty-eight Chicago companies, each backed with a $25,000 check from Fifth Star.

Every one received the same $25,000 check. Eight have since raised $100,000 or more in investment, and the full record by year, closed companies included, is on our research page.

Portraits of founders backed by Fifth Star Funds
The portfolio

28 companies

The year on each card is when we invested. "Raised follow-on" means the company has since raised $100,000 or more. "Building" means the company is still operating.

EducAIte logo

EducAIte

Erica Bishaf and Campbell Schafer

A school-run AI environment where students learn to think with AI, and teachers can see how they are doing it.

2026 Building
Hyphae Composites logo

Hyphae Composites

Adriana Esparza

A standalone machine that repairs a factory's own plastic scrap at the molecular level, so it goes straight back onto the line as production-grade resin.

2026 Building
The Dev Difference logo

The Dev Difference

Jovanay Carter, Jolene Bernagene and Moyosore Okeremi

Runs the first round of a technical interview with a conversational AI, then reports how the candidate thinks.

2026 Building
KNOWN logo

KNOWN

Isabella Zhang and Joyce Guo

Tracks the whole hormonal cycle, not just the period, and lets you share where you are with people you choose.

2026 Building
CareLumi logo

CareLumi

Shai Basys and Claire Chen

Handles the credentialing a clinician needs before they can legally treat patients and bill insurance.

2026 Raised follow-on
Banyon Power logo

Banyon Power

Brian Tolliver

Manages when electric cars charge, so owners skip a costly panel upgrade and utilities keep the local grid steady.

2025 Raised follow-on
Sweet logo

Sweet

Toni Witt and Femi Odugbesan

Works inside small accounting firms as an outside AI lead, building the automations that take the grind out of tax season.

2025 Building
Tenacity logo

Tenacity

Devin Tyler

A marketplace that matches companies with vetted student freelancers for marketing, business and tech work.

2025 Building
ThrowbackBuys logo

ThrowbackBuys

LeMarc Johnson

A marketplace for the toys, tapes, clothes and tech people grew up with, from the '80s through Y2K.

2025 Building
Arke logo

Arke

Nana Arkorful

Electric bikes and conversion kits, built for delivery riders in Detroit and Accra.

2024 Building
Aegis logo

Aegis

Tamika Vantifflin

Two taps call 911 and send your location, medical details and a recording, for when you can't speak.

2023 Raised follow-on
Approachable logo

Approachable

Matthew Williams

Plans a real outing and puts you in a small group of compatible strangers, so you don't show up alone.

2023 Building
Centinel logo

Centinel

Soton Sauerland

A membership that pays a small business automatically when the power goes out, with no claim to file.

2023 Raised follow-on
FOODe logo

FOODe

Ken Clay

Finds the restaurant, books the table and pays the bill, and sends a cut of every transaction to local food banks.

2023 Raised follow-on
Minority Business Circle logo

Minority Business Circle

Amera McCoy

One membership dashboard of classes, coaching, lender connections and software discounts for minority-owned businesses.

2023 Building
Skilbi logo

Skilbi

Emmanuel Noel

Helps students without a professional network build skills, find mentors and get in front of employers.

2023 Building
Barter-E logo

Barter-E

Ayrika Craig

Lets founders and creatives trade services with each other instead of paying cash.

2022 Building
CulturePilot logo

CulturePilot

Barbara Kuofie and Mariyam Khalid

Point your phone at a statue or a building and get the story, in audio and text.

2022 Building
E3 Radio logo

E3 Radio

Anna DeShawn

A queer-owned media company behind E3 Radio, the weekly Queer News podcast and The Qube, a discovery platform for Black and Brown podcasts.

2022 Building
Eventnoire logo

Eventnoire

Jeff Osuji and Femi Masha

Ticketing and event software for the hosts who shape Black culture, with service fees shared back to them.

2022 Raised follow-on
FlareFS logo

FlareFS

Vernon Gair

Fund accounting for nonprofits, so money restricted to a purpose is tracked to that purpose.

2022 Raised follow-on
HCISS logo

HCISS

Daniel Addison

Threat detection and encryption for critical infrastructure and the organizations legacy vendors ignore.

2022 Building
Let's LiNK logo

Let's LiNK

Justice Moore

Buy and sell luxury and vintage goods in person, with the money held until the buyer has the item in hand.

2022 Building
PiggyBack Network logo

PiggyBack Network

Ismael El-Amin and Donald Scott II

Matches parents driving the same direction so they can share the school run and the practice run.

2022 Raised follow-on
Spark logo

Spark

James Bender and Khalil Simmons

Shows you who else is in the room and why they came, so you can go and say hello.

2022 Building
Supperclub logo

Supperclub

Mia Marshall

Book paid one-to-one time with someone hard to reach, by video, audio or text.

2022 Building
City Health Tech logo

City Health Tech

Irewole Akande and Ibraheem Alinur

Makes Opal, a screen by the sink that coaches proper hand washing and records how long it takes.

2021 Building
Roomii logo

Roomii

Dapo Kolawole

Rent, buy or sell good second-hand furniture from people nearby, with pickup and delivery handled.

2021 Building
Jeff Osuji, co-founder of Eventnoire
One founder

"Fifth Star Funds' investment in Eventnoire helped accelerate the development of our front end... Having their support changed my mindset and gave me a sense of pride knowing that I was not alone on this journey."

Jeff Osuji · Co-founder, Eventnoire · Backed February 2022

Read Jeff's page

Closed companies

Eight companies have closed since 2021.

They're counted in our research, not listed here. All eight came from our first two cohorts. The portfolio by year, closed companies included.

Back a founder

Every contribution goes into the fund that writes the next first check.

If any of these companies exits, our share comes back to the fund and goes out again as another first check, which is what makes us an evergreen fund.

Stay in touch

Updates on the founders we back and the work behind the checks.