The Second Check is Harder Than the First
Overview
(Written Lesson Only/No Video)

Most founders celebrate their first grant like it's a finish line.
It's not. It's an audition.
The real test comes when you go back for renewal. That's when funders decide whether you were a good bet or a one-time experiment.
According to Candid's Foundation Funding Trends, only 40-45% of first-time grantees receive renewed support from the same funder within three years. More than half have to start from scratch every cycle.
Why?
Because most grantees disappear after they get funded. They submit their final report and vanish until they need money again.
Funders notice the silence. They interpret it as a red flag.
What Happens After You Submit Your Final Report
Here's what actually happens inside a foundation after you hit "submit":
Within 2 weeks: Program officer reviews your report and mentally categorizes it as "strong," "fine," or "concerning"
Within 30 days: Your work gets discussed at a team meeting where staff debate whether it still aligns with their priorities
Within 90 days: You get sorted into one of three buckets:
"Invite to apply again"
"Monitor for later"
"One-time investment"
You don't see any of this happen. But it determines whether your next email gets answered or ignored.
The Three Questions Funders Ask Before They Renew
1. Did they execute well?
On time, on budget, with clear communication throughout
2. Did the work produce real outcomes?
Measurable results that match what we funded
3. Are they building something sustainable?
Growing capacity, not just repeating the same project
If the answer to all three is yes, renewal conversations start before you even apply.
If the answer to one is no, you're back to competing with strangers.
What Strategic Grantees Do Differently
Organizations that secure multi-year funding don't go silent. They stay visible with small, consistent touches.

Send Quarterly Updates
Not when things go wrong. When things are moving.
A 200-word email every three months with:
One metric showing progress
One story illustrating impact
One lesson you're learning
Example:
"We've reached 180 of our 200-participant goal for Q2. One surprise: 40% of participants are referring friends, which is speeding up our growth. We're learning that peer recruitment works better than institutional outreach. As we plan next year, we're weighing depth (more support per person) vs. breadth (reaching more people). Would love your take if you have 10 minutes."
This kind of update shows progress, demonstrates learning, and invites the funder into your thinking. It takes 20 minutes to write. It makes renewal feel obvious.
Invite Them to See Your Work
This could include:
Community events where they can meet participants
Panels where you're sharing insights
Site visits where they can see your operation
Funders remember organizations they've physically experienced. Those memories make renewals easier to justify internally.
Not every funder will say yes. That's fine. The invitation itself signals confidence.
Acknowledge Their Role When Things Go Well
When their funding creates visible results, tell them:
"Your investment allowed us to hire our first full-time program manager. That hire just helped us land a $100K city contract."
"The pilot you funded is now being replicated by three other organizations."
"We got featured in [Publication]. The work they covered came from your grant."
These messages show ROI. They make the funder feel like a partner, not just a checkwriter.
What to Do This Week
Pick one funder you've worked with. Ask yourself:
When's the last time I sent them an update?
Have I invited them to see the work?
Do they know I want to partner again?
If your answers reveal silence, fix it. Send one email. Share one win. Start one conversation. Renewal doesn't begin when you need money again.
It begins the moment you cash the first check.
What's Next
As you grow, fundraising becomes more than a one-off effort. In the next section, we’ll break down what a multi-year fundraising arc looks like, how to build on early wins, deepen funder relationships, and align your capital strategy with long-term goals.