Fifth Star Funds
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Apply for a first check

We invest $25,000 in Chicago founders at the Friends & Family stage.

Six things have to be true, and they're listed just below. We're founders too. We read every application ourselves, and we'll tell you where you stand either way.

Start the application How it works
Who we back

Six things have to be true. If they are, we'd like to hear from you.

The evaluation is where we get to know you.

The founderAt least one co-founder who has faced material barriers to accessing capital due to racial discrimination. That's the criterion, in full, and it's open to founders of any race who've faced it.
The cityHeadquartered in Chicago. We invest here, and you'll build alongside the other founders we've backed.
The stageAt the Friends & Family stage. You've started, you may have a first version or first users, and you haven't raised a priced round. Pre-revenue is fine. That's the stage we invest in.
The companyTech-enabled and built to scale. We're a fund, so the business needs a path to becoming much bigger than it is today.
The raise so farLess than $25,000 previously raised in equity capital. That counts wired equity investments only. Verbal commitments and non-dilutive grants don't count.
The entityA corporation or an LLC.
What you get

The check is the start. The rest is the network that usually comes with friends and family money.

$25,000

On a SAFE

A standard post-money SAFE with a $4M valuation cap and a 20% discount. Same terms for every company, with no board seat and no negotiation.

LongJump coaching

Every founder gets founder-led coaching and structured programming through LongJump, our operating partner in Chicago.

Introductions

Introductions to the Chicago investors and operators who should know you next, made when you're ready for them.

The 1871 community

Fifth Star grew out of the 1871 community and our portfolio gathers there. You'll know the other founders we've backed by name.

How it works

From your application to the first check.

We run an evaluation cycle every quarter. Founders who meet our criteria record a short screening interview, the strongest are invited to a live interview with a member of our investment committee, and the committee decides.

A no for now

Every founder we interview hears back from one of us, with our reasons, and you can apply again in any later cycle.

Apply

The form below. It takes about 30 minutes if you know your business, and it's the same questions the interview builds on. Tell us how you found us.

Screening

We check the six things above and read what you've written. If we're not the right fit, we say so quickly and point you somewhere better.

Recorded interview

Founders who meet our criteria record a short interview online. Every founder gets the same questions, and you'll know what we're asking about before you start.

Live interview

We read each screening interview against the rubric, and the founders who come through strongest meet a member of our investment committee for a conversation about the business and what the check would do.

Investment committee

The committee, which includes members of the board, reviews your application and both interviews together and votes.

Decision

A yes, or a no for now. Either way you hear from a person.

First check

We sign the SAFE, wire the $25,000, and introduce you to LongJump, and we stay in touch as you build.

The rubric

We score ten things. Here they are, so you can get ready.

We built the rubric so pedigree counts for less. It looks at what you understand, what you've done and how you respond when the plan changes. If you can speak to all ten, you're ready to apply.

Problem, customer, competitorsYou know the problem deeply, who has it, and who else is trying to solve it.
Market sizeYou've researched how big the market is, and you can show the assumptions behind the number.
Solution validationYou have tangible evidence that people want this: research, sign-ups, engagement, or early users who keep coming back.
Adaptability and opennessYou listen to data and feedback, and you can point to a time you changed course because of it.
Unit economicsYou understand the market dynamics well enough to explain how the business makes money at scale.
Product prioritiesYou know what to build first and why, and the why connects to a bigger goal.
ResourcefulnessYou know which skills the company needs, and you've found ways to cover the gaps before you could pay for them.
Plan for use of fundsYou know what the $25,000 does and what milestone it gets you to. Even rent counts, if it's part of a plan.
GritPassion for the idea and perseverance you can show from your life so far. We look for this more than traditional achievement.
Business viabilityEvidence that somebody will pay for this, and a realistic route to the people who would. We ask what it takes to reach them, not whether you have already.
The application

The application takes about 30 minutes.

Save your answers somewhere as you go. If we're between cycles, we'll hold your application for the next one and let you know when it opens.

Trouble with the form? Open it in its own tab.

Questions before you apply? Write to us. If you're looking for a grant rather than an investment, start here instead.

Stay in touch

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