Jenna Nicholas, President of LightPost Capital and author of Enlightened Bottom Line
LightPost Capital
A few years ago, Jenna Nicholas sat in a room full of old friends at the retirement party for one of the founders of the Calvert Funds, a pioneer of socially responsible investing. Someone told the tombstone story again, the one about Wayne Silby, who started Calvert and once went on a Buddhist retreat where he was asked to imagine his own tombstone. His honest answer: “the man that made 2% more than the next man.” He hated it. He went back to his colleagues and pushed the firm toward social responsibility instead. Today Calvert manages roughly $45 billion.
Nicholas had heard versions of that story before. She’d spent fifteen years working alongside Silby and the rest of the generation that built the impact investing field, and now runs her own firm, LightPost Capital, an early-stage and lower-middle-market fund betting on climate, healthcare, and education. Watching those pioneers age, she set out to interview them for a book, wanting to capture their stories while she still could.
A few of the people she interviewed have since passed away. Going through those conversations, a pattern kept surfacing, one she eventually organized into a framework she calls HEAL: Hope, Empathy, Abundance, Legacy. That framework became the spine of the book, published earlier this year under a title that doubles as a challenge to anyone still treating profit and purpose as opposites: Enlightened Bottom Line: Exploring the Intersection of Spirituality, Business, and Investing.
“These are tools that investors, business leaders, others can use on their journey of really blending meaning and purpose into their daily work and activities,” she said. It applies, she added, “no matter what role one may play within an organization or within society.”
Four Pillars, In Order
The book runs through the pillars one at a time, each chapter ending in reflection questions built to be worked through alone or with a team. Nicholas says people are actually using them, not just skimming past.
Hope gets the most real estate. She borrows a phrase from researcher Brene Brown, “microdosing hope,” because it’s small and repeatable, not a mood you wait around for. Her go-to example is Scott Schickler, who runs the education company Seven Mindsets. He keeps a wand on his desk. “When he finds himself in more of a fear or scarce-based thinking, he literally waves the wand, and it helps him to cultivate more of a sense of hope and possibility,” Nicholas said. Hope, in her framing, isn’t a feeling that shows up on its own. It’s a habit. And habits need a trigger you can actually reach for.
Enlightened Bottom Line: Exploring the Intersection of Spirituality, Business, and Investing, by Jenna Nicholas
Jenna Nicholas
Where the Framework Meets a Term Sheet
This isn’t theory Nicholas keeps in a book. HEAL is how she underwrites deals at LightPost.
Take Devoted Health, a portfolio company that recently raised at a $13 billion valuation. Before any provider sees a patient, they’re told to pause and picture that patient as family. “Imagine if in all of our organizations, we were to practice something like that around what does it look like if we engage with people as if they’re beloved family members,” Nicholas said. One small ritual, standing in for a much bigger question: what happens once empathy is a step in the workflow instead of a value painted on the wall.
The rest of the portfolio runs on the same logic. Cambium sells sustainable timber to companies like Google and Amazon, using AI to manage supply chains that used to run on guesswork. Evertai, founded by Dr. Larry Brilliant, who helped eradicate smallpox and later ran Google.org, is using AI to make medicine personal again instead of one-size-fits-all. Clarinet helps companies actually adopt AI instead of just talking about it, pairing the tech with training so it sticks. Checks run from early-stage rounds to full acquisitions of companies pulling in $5 million to $15 million in revenue, a roll-up strategy Nicholas says buys her something rarer than upside: control over the culture, not just the cap table.
“We really are seeing our work with LightPost as a living laboratory for the exploration and application of many of the principles around this intersection of spirituality and business and investing,” she said.
The Thing People Don’t Say Out Loud
There’s a pattern Nicholas kept hitting across her interviews. People would open up about how much spirituality and purpose mattered to them, then catch themselves mid-sentence: “I don’t really feel like I can talk about it.” Her stated goal is “to lower the barriers to entry for engaging around some of these topics and to normalize it as part of our business and investment decision-making processes.”
That instinct also shapes how she reads impact investing itself, a field she’s watched swing for fifteen years. Younger investors keep pushing harder for portfolios that match what they actually believe. Some institutions, meanwhile, have gone quiet on ESG language, especially in the US. Nicholas doesn’t read that silence as surrender. She reads it as people getting serious about measurement and choosing to stop talking about it in public.
Betting on Infrastructure
Nicholas’s entire career argues against splitting purpose and performance into separate columns. Hope, empathy, a sense of enoughness, none of it is garnish on a good business. In her version of investing, it’s underwriting criteria, no softer than a balance sheet.
Schickler’s wand is a small, slightly ridiculous object sitting on a desk in an education company most people have never heard of. But it points at something Nicholas is building a career around: the idea that hope isn’t weather you wait out, it’s infrastructure you put in place on purpose. LightPost is still raising its first fund. The HEAL framework is still spreading one portfolio company, one reflection question at a time. If either takes hold the way Calvert once did, the next generation telling stories at a retirement party might not be talking about a strange exception to how business gets done. They’ll be talking about how it always should have worked.
