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2025 Summer Newsletter: In Celebration of Entrepreneurship

Highlights: The Power of Entrepreneurship, Portfolio Insights and Updates, Event Previews and Highlights, and More Ways to Engage

Nothing contained in the newsletter is intended nor should anything included herein be considered a guarantee of future performance of any industry, asset class, or any security.

One of the core tenets of Gratitude Railroad’s theory of change is backing the power of entrepreneurship, which reflects our belief in the potential of for-profit companies to address social and environmental problems effectively and at scale. Entrepreneurs are often defined as people who start new businesses, an endeavor marked by risk and the potential for reward. We also embrace the original definition of the word “entrepreneur,” established by the influential French economist Jean Baptiste Say who coined the term around 1800: “The entrepreneur shifts economic resources out of an area of lower and into an area of higher productivity and greater yield.”

Entrepreneurs – shifters of resources – are well-suited to lead during times of change and uncertainty, as they are inclined to see, adapt to and even thrive during market dislocation. We are seeing this in our own investing as policy and macroeconomic changes upend previous industry dynamics. Our portfolio company founders are responding by shifting priority markets, products and customers, often taking advantage of intentionally developed business line diversification and cultures of innovation. Our portfolio fund managers continue to find attractive opportunities given they already have an eye toward emerging economic waves such as the future of work, the care economy, and the unstoppable aspects of the green transition.

We take heart in the ambition and grit of our portfolio founders and managers whose drive is bolstered by a sense of purpose and desire to create change. We continue to partner with entrepreneurs who are deeply connected to their work and manage businesses that balance execution and innovation. We continue to draw from our own entrepreneurial spirit and that of our committed network of investors; in fact, we are excited about the potential in upcoming months to grow and strengthen our impact – focusing on the idea that “In uncertainty, there is also opportunity.”

We are thrilled to share some of the entrepreneurial successes from Gratitude’s portfolio in this newsletter. These successes continue to motivate this Community to transform capital to create a thriving world.

With Gratitude,

Rebekah and Thomas

Community. Capital. Change!

What’s New at Gratitude

Investments

Community and Events

Links to Inspire

Whats New at Gratitude

ImpactAssets 50: Gratitude Railroad is recognized as Emerging Impact Manager

Our firm was selected to the ImpactAssets 50 this year as an Emerging Impact Manager. The ImpactAssets 50 started in 2011 as a free, annual resource for investors, advisors and philanthropists to identify the top experienced and emerging impact fund managers and is intended to illustrate the breadth of impact fund managers operating today. We are honored to be recognized for our community-driven investment model that leverages our 10+ year track record of backing compelling market-based solutions to address systemic issues across planetary health, social wellbeing and intersectional innovation.

Congratulations to the other recognized fund managers who are contributing to the growth of the impact investing sector! If you are an impact manager who is interested in applying for the 2026 IA 50 list, you can sign up for information here.

Support for Berkeley and Duke MBA Programs

This spring we had the privilege of working with two MBA teams to explore how Gratitude can deliver greater value through a tech-enabled lens. Like many organizations navigating how to adapt and leverage machine learning tools to its greatest potential, we felt it was critical to spend time dissecting the potential of how this all applies to Gratitude’s internal operations. A team from Duke University’s Fuqua School of Business examined ways to evolve our membership experience, including recommending smarter uses of automation and intentional funnel design. In parallel, a team from UC Berkeley Haas School of Business focused on the role of AI across the investment workflow, identifying tools and use cases to streamline sourcing, diligence, and reporting, while also offering guidance on responsible implementation.

We’re grateful to the students who brought thoughtfulness and rigor to this work: Naoto Kawakami, Anran Li, Alan Luo, Daniel Norman, Andres Parraguirre (Duke), and Ramin Abbasov, Ishita Rustagi, Amy Wu (Berkeley Haas).

Investing Across Impact Themes

In line with our theme in this newsletter, we recently shared more about Gratitude’s investment strategy and our more generalist approach across planetary health, social wellbeing and intersectional innovations in a piece titled “Investing Across Impact Themes: Entrepreneurs over Silos,” written by our Managing Partner and Co-CEO Thomas Knowles. Read the piece here about how we believe it always comes down to the founders.

Investments

We invest in early-stage companies and emerging funds with a dual focus on compelling financial returns and authentic impact. Our investments address at least one of our core themes: Planetary Health [renewables and natural systems], Social Wellbeing [health, education, and wealth equity], and Intersectional Innovations [food systems and climate justice].

Direct Company Investments

Cofertility

Cofertility is a human-first fertility platform that makes egg freezing more accessible by enabling donors to freeze their eggs for free when they donate half. Its unique egg-sharing model brings a new, diverse group of educated donors into the market by helping them to freeze eggs at their healthiest age without the upfront cost.

We participated in Cofertility’s $7.2M Series A, led by Next Ventures and Offline Ventures, to support the company’s team and technical growth. As egg freezing and surrogacy rise alongside delayed family formation, Cofertility expands access to fertility services for women, LGBTQIA+ families, and the BIPOC community. You can read more about why we invested in Cofertility in our recent blogpost by Emma Leavy.

Flourish Health

Flourish Health is a telehealth and in-home behavioral health care provider specializing in high-acuity mental health treatment for adolescents. They focus on serious conditions such as bipolar disorder, psychosis-related issues and major depressive disorder, combining high-touch, in-person support with virtual psychiatric care. The program is especially designed to serve families and young adults covered by Medicaid and major insurance plans across the U.S.

We participated in Flourish’s most recent round of financing alongside notable mental health and impact investors such as AV8, Hopelab, Acumen, Luminary and Greymatter.

Retirable

Retirable helps everyday Americans, especially those with modest savings, plan and manage their retirement income. Most people approaching retirement don’t have access to trustworthy, affordable financial advice. Retirable fills that gap by using technology and AI to make retirement planning easier and more affordable, pairing real advisors with smart AI tools to serve low and middle-income retirees more efficiently. The company recently raised $10 million in new funding with backing from IA Capital, Clocktower Ventures, Nationwide, Impact Engine, and others.

Joint Ventures

Gratitude Railroad and Plankton Energy continue to work together to expand distributed and community solar in the Northeast. We are currently partnering on a suite of projects on the campus of Curry College, a liberal arts school outside of Boston. These rooftop and parking canopy installations will allow the college to reduce its energy bills alongside low- and moderate-income households in the area who will subscribe to the projects. Notwithstanding the broader changes around renewable policy, we are focused on executing and growing this body of work, capitalizing on Plankton Energy’s long experience and deep development pipeline. This work is also supported by RSF who is providing debt financing for our current projects as part of their broader climate lending portfolio. In addition, we recently partnered with Climatize, whose mission is to democratize climate investing and expand financing options for bankable small and medium solar and storage projects. You can see our project listed on the Climatize site here.

Portfolio Updates

Glacier

Glacier raised $16M from Ecosystem Integrity Fund, Amazon Climate Pledge Fund and others in their Series A to scale their AI-powered recycling robots across the U.S. Glacier’s innovative robots sort over 30 kinds of recyclable materials at up to 45 items per minute, making recycling a lot more efficient and effective, and helping to fill staffing shortages within recycling facilities. Glacier also marked their entry into Washington state with the installation of their recycling robots at Recology’s King County Material Recovery Facility in Seattle. You can read more about the firm and their raise in this TechCrunch article here.

Community and Events

We host a variety of virtual and in-person events throughout the year centered around community building, shared learning, and investment exploration. If you’re interested in partnering or attending our events, email events@gratituderailroad.com.

Upcoming Events

August

Indianapolis Investor Dinner
August Investment Meeting

September

LP Summit and East Coast Gathering

October

October Investment Meeting
Virtual Member Mixer
San Francisco Breakfast around SOCAP

Past Events

Topical Roundtable: Taking Action on Biodiversity Risks and Opportunities in Portfolios with Fiduciary Trust International

In June, we organized a topical roundtable with Fiduciary Trust International on Taking Action on Biodiversity Risks and Opportunities in Portfolios. We were joined by experts in this field: moderator Frances Aderhold, Assistant Vice President and Research Analyst of Sustainable Investing at Fiduciary Trust International, Tanya Khotin, Adjunct Professor at Columbia | SIPA and former board member of Norcross Wildlife Foundation, Mary Beth Gallagher, Director of Engagement at Domini Impact Investments LLC, and Kevin Webb, Co-Founder and Managing Director of Superorganism. The panelists covered how to identify nature-related risks and opportunities as well as actionable strategies for addressing biodiversity risk in investment portfolios.

2025 West Coast Gathering

Our 2025 West Coast Gathering gathered nearly 80 investors, founders, fund managers, and impact leaders to explore the resilience of the impact investing industry in the Bay Area during SF Climate Week.

From discussions on climate resiliency, interactive workshops on mental health and education, a fireside chat on the state of the private impact investing market, site visits to Blue Ocean Gear and Glacier, and more, the Gathering showcased resilience in the impact investing landscape. We are so grateful to our speakers, sponsors — ImpactAssets and Veris Wealth Partners, as well as in-kind sponsor The Foster Museum — and attendees for their contributions. We look forward to the upcoming East Coast Gathering and LP Summit later this year.

Community Led Events

Bay Area Member Meetup on Regenerative Food and Agriculture

In February, Petra Silton and Julia Sunderland co-hosted a Bay Area meet-up focused on regenerative food and agriculture and attended by investors, farmers, and local leaders. The brunch featured home-made dishes and baked goods, utilizing ingredients from local farms. Veronica Mazariegos-Anastassious of Brisa Ranch spoke about her work as a farmer and a thought-leader, and the Gratitude team shared some highlights from our research on investment opportunities in the broader space.

Investing in Reproductive Rights Session in Denver

In March, Veris Wealth Partners hosted a Denver lunch event focused on investing in reproductive health. Rebekah Saul Butler joined Ruth Shaber, Erika Seth Davies, and Ronda Dean on a panel addressing opportunities across early-stage innovation, whole portfolio activation, shareholder activism, and public benefit corporations and other patient-centered providers. You can find the event recap and takeaways here.

Charleston Impact Breakfast

In April, we co-hosted a vibrant breakfast in Charleston with members Kate Nevin and Sarah Gravely of TSWII Capital Advisors. Attendees ranged from individual investors to financial advisors and operators to board members, and we had a rich discussion on how to approach investing through an impact lens, as well as the alternative strategies we can pursue to keep funding this impactful work in light of federal funding cuts.

Minneapolis Member Dinner and Roundtable

In May, we visited Minneapolis and co-hosted two convenings. Cogent Consulting invited Rebekah Saul Butler to share strategies on getting to a 100% mission-aligned portfolio with members of the local Impact Investing Roundtable. In the evening, we co-hosted a dinner event where participants reflected in various ways on the question: Can Capital Heal or Only Multiply? – and explored how to infuse investments with values.

Montauk Lunch Gathering

In June, long standing and committed member and investor, Fabio Rosati, hosted us at the Third House Nature Center in Montauk. In addition to providing an update on our community and investments, we welcomed a local entrepreneur, Will Peckman of West Robins Aquaculture, who provided amazing fresh oysters!

Impact Investor Gathering in Portland, Maine

In July, we cohosted a unique gathering in Portland, Maine, with Northeastern University’s Roux Institute, Orange Bike Brewing Company, and Luke’s Lobster — bringing together a dynamic group of over 50 accredited investors committed to exploring and advancing impact investing. We kicked off the day with rich conversations at the Roux Institute, shared a delicious lunch at Luke’s Lobster on the waterfront, and closed with thought-provoking sessions and local brews at Orange Bike Brewing. We also heard from a powerful lineup of founders and investors who are pushing the boundaries of how capital can be used to build a more just, equitable economy.