Fifth Star Funds
Apply Give
Chicago's Friends & Family Fund

World-changing ideas come from all walks of life. We write the first check needed to build them.

A nonprofit fund providing catalytic capital to overlooked founders in Chicago. We invest $25,000 at the very start, and every return goes to the next founder.

The Friends & Family round

Most companies begin on the founder's own savings and money from the people closest to them. That round decides who gets to start.

Before an angel or a venture fund will invest, a founder needs a small amount of money to build the first version and find the first customers. It comes from savings, and from parents, siblings, a college roommate, an old boss.

Founders with great ideas come from every background, but not all of them have family wealth or a network to draw on. Leave home equity out, because a home can't be wired to a startup, and a $25,000 check is more than many families could ever put in. Venture funds can't invest in companies that don't exist.

Why the first check decides who gets to start

Census Bureau, Survey of Income and Program Participation, 2024 tables, the current release, median household net worth excluding equity in own home. How we calculate it, and the six-year trend.

Since our first check in June 2021
36
companies backed, every one with a $25,000 check
$900K
invested, all of it from contributions
25%+
have gone on to raise $100,000 or more

Our companies are selected, so these numbers describe our portfolio, not the effect of the check on its own. Figures from our investment tracker, October 2026. The full record, by year.

How it works

Your contribution funds a founder's first check, and anything that comes back funds the next one.

You give

A tax-deductible contribution to a 501(c)(3). In our current budget, about $20 of every $25 goes to founders and $5 runs the fund.

We write the first check

$25,000 on a standard SAFE, for founders chosen on grit and execution rather than pedigree, with coaching and introductions through our operating partner, LongJump.

Returns go to the next founder

Proceeds from an exit go back into the fund as another first check, which makes us an evergreen fund. We expect the first returns on a five to ten year horizon.

The whole loop, with a worked example

Why a nonprofit? Because capitalism breaks down at the Friends & Family round. The companies are too early and too risky for any fund that has to return money to investors. A family writes the check anyway, because the return comes back to the family. We built a fund that works the same way for a whole city.

Tim Huelskamp, co-founder
Portfolio

Meet the founders we've backed.

Software, hardware, healthcare, media and marketplaces, every one backed with the same $25,000 check.

All our companies, and the founders behind them

Supporters

More than a hundred individuals, family foundations and companies have funded these checks since 2021.

Foundations
RLD FoundationSteans Family FoundationThe Allstate FoundationGoldman Sachs Foundation
Corporate
Salesforce
Ecosystem partners
1871LongJumpChicago:BlendWinston Taylor
Individuals

Chicago founders, operators and investors.

All our supporters

Three ways in

Give a founder the same starting line as a peer with a wealthier network.

1

Back a founder

$25,000 is one check. Any amount joins the fund that writes these checks, and contributions are tax-deductible.

Give
2

Apply for a first check

Chicago-based, at the Friends & Family stage, with at least one co-founder who has faced material barriers to accessing capital due to racial discrimination.

Apply
3

Partner with us

If you work with founders this early, or invest after us, we'd like to know you.

Get in touch

Stay in touch

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