City Lore has been doing this work for over two decades — that's not nothing. That's institutional knowledge, earned trust, and a track record most organizations would envy. But when you describe your board as a mixed bag — some of them great and supportive, others not doing anything for you — you're naming something that quietly costs you more than it appears. That tension sits at the center of what this report is about. Let's look at what's holding City Lore back, where the real leverage is, and what a clear-eyed path forward looks like.
Jesse Lane founder of goodmakerU, has a message to walk you through your report to let you know whats here, and how to use it.
Board dysfunction is almost never about bad people. It's almost always about unclear expectations — which means it's fixable. When you described your board as a mix of engaged champions and people who aren't doing anything for you, you gave us the diagnosis in one sentence. That split is common, and it's usually the result of a recruitment process that prioritized credentials or connections over explicit commitment. Nobody handed those quieter members a job description, and nobody held them to one. The tool that changes this is what GoodmakerU calls Specific Asks — because 'help more with fundraising' allows nodding and inaction, while 'make two donor introductions this quarter' allows only yes or no. Most disengaged board members are quietly relieved when someone opens that door with clarity. You've named board engagement as a priority, and that instinct is right — the organization is ready for that conversation, even if it's uncomfortable.
With foundations and grants as your primary funding source, and 51–70% of your revenue tied to that single channel, City Lore is carrying real concentration risk. You probably already know this — most leaders do — but awareness without a sequenced plan is just anxiety with better vocabulary. The path forward has three steps: stabilize the concentrated source first, then build one new stream (not three), then give it time. GoodmakerU's framework here is Protection → One New Stream → Patience. Eighteen to twenty-four months to meaningful diversification is honest. Twelve months is aggressive. Anyone promising ninety days is selling something. The specific move for City Lore is identifying where individual major gifts could grow — your two-decade history and program depth are exactly the story high-capacity donors respond to. You've already flagged increasing grant funding as a near-term priority, and that's smart for stability. But the longer play is reducing the percentage that foundations represent, not just growing the total.
City Lore has done everything right to reach this stage — twenty-plus years, a million-dollar-plus budget, real programs, real impact. The ceiling you're bumping against isn't a failure. It's actually proof the first chapter worked. But the model that built you here is the same model that's capping you now. GoodmakerU's $500K Question is useful here: if someone handed you $500,000 tomorrow, what would break first? For most organizations at your stage, the answer is infrastructure — hiring capacity, board composition, revenue systems. You've flagged hiring key staff positions as a top priority, and that signal is important. Scaling programs before scaling the team and structure underneath them is the trap. The shift Ready to Scale organizations have to make is distributing real decision-making authority below the executive director level, evolving the revenue mix toward major individual gifts, and upgrading board composition for growth skills rather than survival skills — which connects directly to what you're already wrestling with.
These three patterns don't sit in separate boxes — they feed each other, and that's what makes them worth naming together. An unengaged board creates a direct fundraising gap: the introductions that don't happen, the major gift conversations that never start, the credibility signals that never reach the right rooms. That gap pushes City Lore further into foundation dependency, because grants feel more controllable than cultivating individual major donors without board support. And the revenue concentration that results from that dynamic is exactly what keeps the organization from scaling — because you can't make the infrastructure investments that growth requires when 51–70% of your revenue is subject to grant cycles and funder priorities you don't control. The path out runs in the same direction: a board that's making specific commitments unlocks individual donor diversification, and that diversification creates the stability to hire, build, and scale without holding your breath every grant season.
Get your team and your board in on this conversation. Reports like this one work best when the whole organization can tackle issues together.
