Jessica Gerwin is Building the Infrastructure for Founder Community With Micro-Grants

Being a founder can be isolating. Every day brings complex problems, hard conversations, and decisions made under uncertainty. The best support often comes from fellow founders—people who can offer perspective, pattern-match across similar challenges, or simply remind you that you’re not building alone.

But meaningful connection rarely happens at formal networking events, and early-stage founders often have limited time or energy to chase serendipity.

That’s part of why Jessica Gerwin, founder of Okaeri, created a micro-grant initiative with Every. Her goal: make founder-to-founder connection effortless and communal—the same philosophy behind Okaeri, which removes the friction founders experience when trying to follow through in their day-to-day work.

Micro-Grants as a Playground for Serendipitous Connection

Jessica’s program offers $25 micro-grants to help founders meet other founders they don’t know well (yet!). Participants can be paired with someone new or choose someone they’ve been wanting to get to know better. All they do is fill out a short form; Every takes care of pairing, approval, and payment.

Unlike formal networking events, founders can meet however (and wherever) they want. “You don’t have to get coffee,” Jessica explains. “If you’re a founder who only drinks matcha—or doesn’t drink caffeine at all—you can do something fun, like go to Tartine, or try bouldering at Mission Cliffs. You can be creative with how you want to meet.”

If a founder isn’t sure who to meet, Jessica offers to match them with someone whose experience, industry, or energy might unlock something for them. The micro-grant removes enough friction that founders finally take the step they’ve been meaning to take.

And that spirit—reducing activation energy so founders can follow through on what matters—is the exact same principle behind Okaeri.

Okaeri: The Follow-Through Layer for Modern Founders

While building community offline, Jessica is also building Okaeri, a voice-enabled follow-through engine that sits on top of the tools founders already use. Okaeri doesn’t replace your CRM or add another dashboard. Instead, it listens to conversations, identifies next steps, and writes those actions back into Gmail, Slack, Notion, and your CRM—turning spoken context into structured execution.

Where traditional systems expect founders to remember everything, type everything, and manually keep tools updated, Okaeri closes the loop automatically.

Here’s the kind of follow-through it makes effortless:

• After an investor or sales conversation, Okaeri identifies commitments (“I’ll send the deck,” “Let’s reconnect Tuesday,” “We’re interested in pending metrics”), drafts the follow-up, and pushes it into Gmail or your CRM—ready for action.
• After a product or internal meeting, Okaeri extracts tasks, routes next steps to the right places, and updates shared docs without anyone needing to type a word.
• When two founders meet through the micro-grants program, and mention something like “Let’s jam on your onboarding flow next week,” Okaeri captures the intent, schedules it, and ensures the right materials are prepped in advance.

Instead of relying on memory, scribbled notes, or good intentions, Okaeri becomes the layer that translates human conversation into actual progress. Just as the micro-grants program makes connection effortless, Okaeri makes follow-through inevitable.

Community as Infrastructure — and Technology as Amplifier

Jessica believes that community is one of the most important forms of infrastructure for early founders. The micro-grants program is a lightweight, joyful way to help founders form the relationships that carry them through the hardest parts of building.

Okaeri extends that same philosophy into software, helping founders start the right conversations and follow through on what matters most.

“Even if it’s not through this program specifically,” Jessica says, “I hope founders feel inspired to reach out to someone new. Maybe they run their own version of micro-grants. Maybe they just send that message they’ve been putting off. I want the SF founder ecosystem to feel more connected, more human.”

Since launching in September, the program has already helped dozens of founders build meaningful connections that might not have happened otherwise—and many go on to collaborate, advise, or build alongside each other.

To learn more about Jessica and her journey, you can follow her on LinkedIn. If you’re interested in connecting with a fellow founder through the micro grants program, you can sign up here.