What I Actually Do (And Why I Can Never Say It in One Sentence)

 I am bad at the elevator pitch. Genuinely, embarrassingly bad.

I was at the Flywheel conference recently, a room full of founders, funders, and community leaders working at the intersection of purpose and profit, and met lots of new people who of course asked the question everyone asks at these things: so what do you do?

I first tried just saying Nonprofit Consultant... and that felt like I was ashamed of something.

The next person asked and I started listing projects. Stood up two collective impact organizations in Kansas City. Did deep ethnographic research for Walmart Health and Quest Diagnostics. Helped a regional anchor institution figure out why it wasn't pulling in national philanthropic dollars. Architected a new performance-outcomes marketplace. Advised a nonprofit executive trying to launch a multi-sector collaborative. Helped a board work through the hard, quiet decision to exit their executive director.

By the third item, I could see the person's eyes doing the thing eyes do when they're trying to find the category. Consultant? Sort of, but I hate that word — it implies I show up with a slide deck and a framework I sell to everyone. Strategist? Closer, but strategy is the visible output, not the actual work. Facilitator? Only a fraction of it.

Here's what I've finally figured out, mostly by accident, mostly because someone else said it for me. At that same conference, a former client introduced me to someone new. She didn't describe my services. She said: "You need to talk to Ryan. He can help."

That's it. That's the whole job description. I chart a path forward for people when the way through isn't clear yet.

Why Cincinnati is the Best Example I have.

Let me show you what I mean, because the abstract version of this is hard to hold onto.

Cincinnati has most of the ingredients for a real social-impact capital market. The Greater Cincinnati Foundation has deployed tens of millions through impact investments — housing, economic revitalization, real units financed, real businesses funded. Flywheel has built a legitimate accelerator track record: dozens of startups, the large majority still operating, real jobs, real follow-on investment. This city helped birth StriveTogether, one of the actual national models for shared civic outcomes and cradle-to-career data discipline. We have the foundations, the hospitals, the universities, the corporate headquarters, the CDFI capacity, the neighborhood infrastructure, the civic pride.

So why doesn't it convert into something more? Into the kind of outcomes-based capital market that cities like Charlotte have built? Why are we still, in 2026, talking about "outcome investing" as an emerging idea rather than a functioning local practice?

It's not a resources problem. It's not even really a structure problem.

It's that Cincinnati is a relationship-rich, conflict-avoidant city: and pay-for-success, by design, requires conflict. It requires two or more parties to agree, explicitly and often uncomfortably, on what counts as success, who pays whom when it happens, and what happens when it doesn't. That's not a financial mechanism. That's a series of hard conversations that a politely networked city tends to route around rather than have.

Nobody wants to be the funder who says I don't trust your outcome data. Nobody wants to be the nonprofit that says we can't take on that much downside risk. So instead, everyone stays in the comfortable register—generous funders, good nonprofits, warm relationships—and the actual machinery of an investable civic capital market never gets built, because nobody's willing to sit in the room where the disagreement has to happen before the agreement can.

It is supposed to be difficult work. That's the point.

This Is the Actual Job - Impact investing Example

This is what I mean when I say I can't give you a tidy one-liner. The work isn't a service category. It's showing up in the room willing to name the thing everyone else is being too polite to name — and then staying in it long enough to help people build agreement out of the friction, instead of avoiding the friction altogether.

Sometimes that's a city's civic capital infrastructure. Sometimes it's a board that's been quietly furious at each other for two years and calling it "differences in style." Sometimes it's an executive director who's lost their nerve and needs someone to help them find it again, not by being handed a five-point plan, but by being asked the right honest question at the right honest moment.

My company is called Friendly Sidekick on purpose. I'm not the hero of any of these stories — the leaders are. I'm the one beside them, willing to see clearly and say the true thing, until they can find their own way through.

If you're trying to build the table where Cincinnati's pieces finally convert into outcomes or you're a leader stuck somewhere quieter and smaller than that, that's the conversation I'm actually good at having.

I just can't say it in one sentence. Apparently it takes a whole blog post.

Big huge congrats to Carley Riley, who is knee-deep in this exact work of outcome financing in our region — somebody has to be in the room doing it, and I'm glad it's her. And big props to Mark Davis, who keeps reminding me that the mechanics of banking are a muscle, and this city needs to do some city-wide bench presses if we're going to get strong enough to lift this.