Fifth Star Funds is a nonprofit Friends & Family fund. Nine entrepreneurs started it in 2020, and founders and operators still run it.
Each of the four stars on the flag marks a moment in the city's history. Chicago has always been a city built on grit, and we think the next star belongs to the founders who carry that forward, from every background and every part of the city.
The founders who keep building are the ones we back. They bring different experiences and different ways of seeing a market, and their persistence is already a track record. We think they're a big part of what Chicago's economy could become.
From 2017 to 2023, Black-owned businesses with employees in the Chicago region grew 38% and Hispanic-owned grew 34%, while the region's total fell 3%.
US Census Bureau, Annual Business Survey, 2017 and 2023 data years, tables AB1700CSA01 and AB2300CSA01, employer firms in the Chicago-Naperville-Elgin metro area.
Fifth Star Funds grew out of the 1871 community. 1871 takes its name from the year of the Great Chicago Fire. In 2021 nine Chicago entrepreneurs who kept meeting the same problem, a good idea and no wealthy network to fund it, started writing $25,000 checks themselves.
World-changing ideas come from all walks of life. Access to the capital required to build them does not.
Some of us raised our first money from friends and family, and some of us couldn't. That's why we take the Friends & Family round seriously. We read every application, and every founder who meets our criteria is offered a screening interview. A founder who gets a check from us gets the people behind it too, for introductions and a phone call when something breaks.
Nate co-founded Clinify Health, a venture-backed digital health company that works with health plans and community health centers, and led it as CEO through its exit. Before Clinify he led corporate strategy for a national primary care provider based in Chicago.
Osa has founded three companies, Fifth Star among them, and is Chief Product Officer at ClearCOGS. He holds a master's in computer engineering from Boston University and an electrical engineering degree from the University of Illinois.
Tim runs 1440, a media company that sends a daily news briefing to millions of readers. Before that he spent close to a decade at a $20 billion private equity and venture fund, investing in technology companies and helping run them.
Kyle runs Fifth Star's operations, from the application cycle to the closing paperwork. He's also co-founder and COO of Verve Reads, a Chicago startup, and a technology consultant to small businesses.
Investment decisions are made by our investment committee, which includes members of the board.
A venture fund. We have no investors to pay back and no fund deadline, so we can invest where most venture funds won't, at the very beginning. And no one takes a cut of the returns.
A grant program. We invest in the company on a standard SAFE, on the same terms a family would.
A nonprofit Friends & Family fund. A 501(c)(3) that writes the $25,000 first check for founders who can't raise it from the people around them, and every dollar that comes back goes out again as someone else's first check.
Run by founders and operators. Our rubric scores grit and execution rather than pedigree.
Most are individuals, many of them Chicago founders and operators. The rest are family foundations, companies and charitable funds, and a lot of them have given more than once.
We wouldn't have written a single check without them.
We ask every applicant how they heard about us and we keep the answer. We've never advertised an application window.
LongJump is the largest single source. Some came from founders we'd already backed. The rest arrived through the Polsky Center, mHUB, 1871, The Garage at Northwestern, and advisors and investors who know what we do.
Fifth Star Funds applicant records, 2026. Founders who weren't referred found us through LinkedIn, search and word of mouth.
Organizations whose people have sent us founders.
1871 named our co-founder Tim Huelskamp its 2026 Outstanding Tech CEO, for his work at 1440. The citation reads, "He launched Fifth Star Funds to expand access to early-stage capital." Eventnoire, a company we backed in 2022, won the Social Impact Award the same night. Chicago Inno named us to its 50 on Fire in 2021. More on the news page.
Foundations, program officers, partners and press. Tell us who you are and we'll get back to you.
Get in touchUpdates on the founders we back and the work behind the checks.
