Charting the Course Together Part 4: What Happens When Both People Show Up

This series started with a metaphor. The captain chooses the destination. The navigator charts the route. Both essential. Neither sufficient alone.

We laid out what the captain owes: a specific destination, not a vibe. Interrogation of where returns come from. Total asset alignment. The willingness to trace every dollar to its beneficiary and to hand power to the people closest to the problems. We laid out what the navigator owes: structural fluency beyond stocks and bonds. The ability to see through impact marketing that the industry produces at industrial scale. Exit planning that preserves mission. Liquidity without dependence on extractive structures. Compensation that doesn't create a structural hostility to the work.

Those are high bars. Both of them. And laid out in sequence like that, they can feel like two parallel lists of demands aimed at two people sitting on opposite sides of a table.

But that misses the point entirely. The point is what happens when both people show up.

The Partnership That Failed

Early in our journey, we held our public equities at a major financial institution. We had done the captain's work. We developed a clear list of exclusions, particularly around the fossil fuel industry. We didn't want to own companies whose primary business was extracting and burning the thing that's destabilizing our climate. We communicated this directly. Our advisor said they would execute the investments we wanted.

A few months later, I downloaded and audited the portfolio.

There they were. Companies whose primary business was fossil fuels. Sitting in our portfolio like we'd never had the conversation.

Our navigator had failed to follow our instructions. It wasn't a misunderstanding. It wasn't a gray area. We had been specific, and they had either ignored us or couldn't execute within their own system. Either way, the trust was broken. We fired them and moved on.

That experience taught us something we should have known from the start. Having a clear destination is necessary. It's not sufficient. The captain can do everything right and still end up in the wrong port if the navigator isn't actually steering.

The Partnership That Worked

When we looked at where we wanted our capital to go, we kept coming back to the same realization: we wanted our money to be productive in the world. Not speculative. Not extracting value from existing companies through public markets. We wanted to build.

Municipal bonds weren't something we'd ever thought much about. But when we learned what they could actually do, we got excited. Fund the infrastructure of civil society. Invest in the communities that most need it. Build the physical world we want to live in. Every dollar was going somewhere we could point to on a map.

But we didn't just want someone to put us into bonds. We wanted a navigator who could find the bonds that built in the communities where we most wanted to focus and created the outcomes we most wanted to see.

That's how we found Eric Glass and Clarion Call Capital. Eric had built and managed the largest tax-exempt fixed income impact strategy at AllianceBernstein before launching Clarion Call to go deeper. He wasn't learning on the job. He had the structural expertise to navigate a $3.8 trillion market and find the specific instruments that matched our values.

Together, we deployed a bond strategy focused on building real societal outcomes in communities that traditional finance routinely leaves behind. Lead pipe replacement in Newark, where over 26% of residents live below the federal poverty line. Community health centers in San Diego serving patients who are 97.5% low-income. Safety-net hospitals in Boston where over 40% of the payer mix comes from Medicaid and charity care. Eric has also led a coalition of investors disrupting prison construction, redirecting capital away from incarceration and toward community infrastructure.

This is what the captain-navigator partnership looks like when it works. We knew the destination: productive capital building civil society in underserved communities. Eric had the expertise to get us there through instruments we couldn't have found on our own. Neither of us could have produced this outcome alone. A captain without a navigator is someone yelling coordinates into the wind. A navigator without a captain who has real clarity is someone running drills in the harbor.

The Lesson Between Those Two Experiences

The distance between the institution that ignored our fossil fuel exclusions and the partnership we built with Eric Glass taught us the most important thing we've learned on this journey: finding the right partner is worth the disruption.

Moving between financial institutions and advisors takes time and effort. There's paperwork. There are tax implications. There's the inertia of an existing relationship. The industry counts on that friction to keep you in place, just like the fee structure we described in Part 1.

But here's what changes when you find the right navigator: you stop auditing and start trusting. Instead of downloading your portfolio to check whether your advisor actually followed your instructions, you download your portfolio and see hope in the future that you are helping to build with your money. You have deep confidence in their alignment. The values transmit cleanly from your theory of change into the actual deployment of your capital.

We earned that trust the hard way. First by working with someone who nodded at our values and then reverted to business as usual. It comes from watching an advisor execute exactly what you asked for, and then bring you opportunities you hadn't thought of that serve your mission even better.

You Are the Expert on Your Values

We want to be direct about something. Throughout this series, we've laid out what the captain owes and what the navigator owes. We've described skills, structures, and standards that can feel technical and intimidating.

Don't let that intimidation hand the wheel back to your advisor.

You are the expert on your values. You know what you care about. You know the world you want the next generation to live in. You know what keeps you up at night and what gives you hope. No advisor, however technically skilled, knows those things better than you do.

The wealth advisory industry has spent decades making you feel like you need their permission to direct your own capital. Like the financial world is too complicated for you to have an opinion. Like your values are a nice-to-have that should yield to the serious business of returns.

That's the inversion we described in Part 1. And it persists only as long as you let it.

Your job as captain isn't to become a financial expert. It's to be so clear about where you're going that your navigator has no room to substitute their destination for yours. That clarity is your authority. An advisor who tells you it's too complicated, that you don't understand, that fiduciary duty prohibits what you're asking for: that's an advisor who is steering you back to their port, not yours.

What "Good Enough for Now" Looks Like

We should be honest. The perfect captain-navigator relationship may not exist yet. We haven't found it fully formed. What we've found are advisors who are strong on some dimensions and developing on others, who are willing to learn, and who share enough of our convictions that the gaps feel bridgeable.

We don't have a single overall advisor. We partner with experts on particular solutions. Clarion Call Capital manages our high-impact municipal bonds strategy. Other partners handle other pieces. This model requires more coordination on our end, but it means each partner brings deep expertise in their area rather than surface-level knowledge across everything.

Direction matters more than position. An advisor who charges AUM fees but is actively exploring alternatives is different from one who defends the status quo. An advisor who can't yet structure a first-loss tranche but is willing to learn is different from one who dismisses the instrument entirely.But trajectory has a limit. An advisor who nodded at our fossil fuel exclusions and then bought fossil fuel stocks wasn't on a trajectory. They were performing alignment while executing the status quo. That's a dealbreaker. Not a gap to be bridged. But maybe you want to be even more clear in your directives. If you are clear that you do not want to be supporting fossil fuels, then your advisor shouldn’t just keep you out of fossil fuel companies. They should understand that you also don’t want holdings in oil refiners and service companies. Or even further, you want to avoid the world's top fossil fuel-financing banks who provide the capital that enables the fossil fuel economy. This requires a dialogue between captain and navigator that goes beyond the letter of the law but to the heart of the spirit of your wishes.  

The Worksheets

We promised practical tools. We're releasing two alongside this post.

The first is a Captain's Preparation Worksheet, designed for you, the investor, to work through before you sit down with an advisor. It draws from the captain's duties we outlined in Part 2 and helps you get clear on your destination, your relationship to returns, your portfolio alignment, and the power structures you're willing to accept. This is homework. You do it alone. And if you can't answer these questions, your advisor will fill the vacuum with assumptions that serve their business model, not your goals.

The second is a Partnership Conversation Guide, designed for use in the meeting itself. It has the navigator evaluation questions from Part 3 reframed as conversation starters rather than a quiz. And it includes questions for both sides, because this post's whole point is that the relationship only works when accountability flows both directions. Bring it to your next advisor meeting. Or use it to evaluate whether you need a new advisor entirely.

These aren't tests with right answers. They're tools for honest dialogue between two people who both need to show up fully.

The Invitation

This series has been about expectations. What investors owe. What advisors owe. What the partnership between them can produce when both parties bring their full weight.

But expectations without action are just another form of admiring the problem.

If you're an investor who has been deferring to your advisor on where your capital goes, take the wheel. Work through the Captain's Preparation Worksheet. Get specific about your values. Then bring that clarity to your next meeting and see whether your navigator can follow your heading. If they can't, or won't, that's information you need. And finding the right partner, as we learned, is worth the disruption.

If you're an advisor reading this, we see you. We know the industry didn't train you for this. We know the fee structures work against you. But there are investors out there who are desperate for a navigator who can meet them where they actually want to go. The ones who find you will be the most engaged, most committed, most rewarding clients you've ever had. Because they've done the work to know what they want.

The captain-navigator model won't fix everything. It won't make impact investing easy or eliminate the tension between financial returns and community returns. What it does is put responsibility where it belongs. Not with the market. Not with "the system." With two people in the room. Both accountable. Both essential. Both willing to go somewhere the industry hasn't been.

We're still charting our own course. We've made wrong turns. We'll make more. But instead of keeping tabs on whether our partners are following our instructions, we have deep trust that our values are transmitting cleanly into the world. That trust didn't come easy. It came from being willing to fire advisors who didn't follow through and to keep searching until we found ones who did.

Your values belong in your portfolio. Not as a label. Not as a side hustle. As the destination. Find a navigator who can get you there, or help your current one grow into the role. Either way, the captain's seat is yours. It always was.