November 30th, 2022

Fifth Star Funds is thrilled to announce its next investments into 8 extraordinary companies. Since our last announcement in February 2022, our portfolio has doubled in size to 20 investments that represent a snapshot of the wonderful Black tech innovation happening in Chicago.

“We’re continually impressed by the sheer volume of remarkable founders and businesses that have come through our pipeline. These founders have highly disruptive businesses in high-growth industries and sectors that need to be given a shot to build companies that will not only change Chicago, but the world at large.”

- Tracey Suppo, Co-Founder of Fifth Star Funds & CEO of Verve Romance

It is our pleasure to introduce you to:


  • ‍Barter-E enables early stage founders to cut back on startup expenses by bartering their unused skills and services so they can focus on taking their companies to the next level. Through an internal currency, founders are able to exchange strengths to save money and time. Barter-E was founded by Ayrika Craig.

The Better Spot:

  • The Better Spot is sustainable wellcare. Putting practitioners first with a secure online community for wellness professionals and their clients along with offline on-demand space, The Better Spot makes integrative care accessible to everyone. The Better Spot was founded by Madilynn Beck.

Flare FS:

  • Flare FS is the financial operating system for nonprofit organizations. Flare helps nonprofits trace every dollar from its source to the outcomes that it supports. This helps nonprofits spend less time on administrative work and more time on running programs. Flare was founded by Vernon Gair.


  • ‍HCISS provides cyber security analytics solutions to find patterns of highly advanced threats and vulnerabilities in smart contract code on the blockchain which result in losses of over $2B in annual security breaches. HCISS was founded by Daniel Addison.


  • NXGRAD offers students a simplified college application experience that allows them to quickly and easily receive multiple admissions offers from colleges and universities that are interested in students like them. NXGRAD was founded by Kyle Westbrook.

Piggyback Network:

  • PiggyBack Network uses artificial intelligence to take the guesswork out of finding a family to carpool with, share rides, and expand support networks. Committed to safety and equity, Piggyback makes transportation available to all communities. Piggyback Network was co-founded by Ismael El-Amin and Donald Scott.

Spark Connect:

  • Spark Connect is the world’s first and only chat-less social networking app that simplifies the art of connecting. Spark’s mission is to make sure that people never miss the opportunity to create authentic connections in person. Spark Connect was co-founded by James Bender and Khalil Simmons.


  • Supperclub is an app that allows you to get paid or pay to chat with who you want and on your terms. In a society of cold calls and unlimited access through social platforms, Supperclub helps you decide which conversations are most valuable and worth your time. Supperclub was founded by Mia Marshall.


“I sit back and look at the entrepreneurs we’ve invested in at Fifth Star Funds and scratch my head in disbelief. These founders are objectively talented, composed of raw passion and limitless grit. Each investment we make further shows the overlooked talent within Chicago’s Black tech ecosystem. I hope that as we continue to grow, others will start to see what we do: that Chicago’s entrepreneurial talent is truly race agnostic. It’s a privilege to invest in our entrepreneurs.”

- David Pawlan, Co-Founder of Fifth Star Funds, Co-Founder of Aloa, Bracketology.tv

Our excitement continues to grow as our newest additions to the Fifth Star portfolio represent momentum gained in our quest to remove the barriers in access to capital that Black tech founders face. It is critical we continue to invest in Black founders in order to help close the wealth gap in the United States today. We remain steadfastly committed to elevating Chicago’s Black tech ecosystem, and are constantly inspired by the talent and potential of the founders we meet.  

“As we grow the number of investments within the Fifth Star Funds portfolio, we strive to always stay true to our mission of fostering a more equitable society by promoting a startup ecosystem that is representative of today's world. What makes us most excited is not our growth as an organization, but rather how that growth shows true signs of creating a greater impact in contribution to our larger, overall mission.”

- Osayanmo Osarenkhoe, Co-Founder of Fifth Star Funds and CPO of ClearCOGS

Thank you as always for your continued support. As we grow the portfolio of Fifth Star Funds, we are as inspired as ever to be the Friends and Family investors of the next generation of Black entrepreneurs that are transforming the Chicago tech landscape!

go  top