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Devin: What is your superpower?
Jenny: Ability to make complex financial and legal concepts accessible.
Creating a thriving community takes more than goodwill—it requires vision, leadership, and resources. Jenny Kassan, CEO of Opportunity Main Street, is proving that crowdfunding can be a powerful tool for revitalizing communities while offering investors a meaningful way to make a difference.
Jenny is raising capital through a regulation crowdfunding campaign on SmallChange to renovate a historic building in Baltimore. This project, called Community Commons, will serve as both a hub for local businesses and a space for community-building activities. The first floor will feature a gathering space, coffee shop, and retail area, while the upper floors will house luxury furnished apartments for short-term rentals.
Jenny explains her motivation: “I’ve believed for a while that it’s really important to create a place-based ecosystem to grow this movement to move community capital into small business.” She has already raised $2.5 million for the project but is turning to crowdfunding to close the final gap.
What makes this project stand out is its intentional focus on Baltimore. After hosting a women entrepreneurs’ event in the city, Jenny fell in love with its historic charm and resilient spirit. “Baltimore is a beautiful, scrappy city,” she says. “There’s a renaissance going on… it’s a place where you can make a significant impact.”
Jenny’s choice of SmallChange as the crowdfunding platform is no accident. She highlights the portal’s commitment to impact-focused real estate projects and its owner, Eve Picker: “She really cares about her clients… and the design of the page is absolutely beautiful.”
By combining real estate with a community-driven mission, Jenny’s project offers an opportunity for investors to see both financial returns and social impact. The short-term rental apartments are projected to generate strong revenue, while the first-floor activities will foster relationships, support local businesses, and teach community members how to invest locally.
This isn’t just about one building. Jenny hopes the Community Commons project will become a replicable model for other cities. “It’s about creating a replicable model for community wealth building and supporting the local investing movement,” she says.
With projects like these, Jenny is showing how crowdfunding can be a bridge between financial goals and community revitalization.
tl;dr:
Jenny Kassan shares her vision for revitalizing Baltimore with a historic real estate project.
Community Commons will combine short-term rentals with a hub for local businesses and activities.
Jenny highlights the impact of crowdfunding and her partnership with the SmallChange platform.
She demonstrates how simplifying financial concepts empowers underserved communities to raise capital.
Jenny’s replicable model aims to inspire more community wealth-building projects nationwide.
How to Develop Simplifying Complex Financial Concepts As a Superpower
Jenny describes her superpower as the ability to make complex financial and legal concepts accessible. She explains, “I’ve learned so much about finance, securities law… and I feel like my superpower is bringing it down to a level of clarity for people.” Her passion stems from a desire to make the world of finance less opaque and intimidating, especially for those who lack traditional financial knowledge or access to resources.
Illustrative Story:
Jenny’s superpower shone when she helped a worker co-op in Boston called CERO raise capital for a composting business. Comprised of highly disadvantaged individuals, the co-op needed funding for a truck but wanted to retain worker control. Jenny structured an offering of non-voting equity, allowing the workers to remain in charge while raising several hundred thousand dollars. This project exemplifies her ability to simplify financial tools for underserved communities, empowering them to achieve their goals.
Actionable Tips to Develop the Superpower:
Deepen Your Expertise: Invest time in learning the intricacies of your field, as Jenny did with finance.
Practice Simplifying Concepts: Break down complex ideas into clear, relatable language to help others understand them.
Empathize with Your Audience: Tailor your explanations to the needs and backgrounds of those you’re helping.
Stay Mission-Driven: Focus on using your knowledge to empower others and create meaningful change.
By following Jenny’s example and advice, you can make simplifying complex concepts a skill. With practice and effort, you could make it a superpower that enables you to do more good in the world.
Remember, however, that research into success suggests that building on your own superpowers is more important than creating new ones or overcoming weaknesses. You do you!
Guest Profile
Jenny Kassan (she/her):
CEO, Opportunity Main Street
About Opportunity Main Street: Opportunity Main Street is growing a place-based community wealth building ecosystem in Baltimore that includes community investing in local business, a community business school, and mutual aid through a time-banking network.
Website: opportunitymainstreet.com
Biographical Information: Jenny is an attorney, coach, and ecosystem builder focused on capital access for underrepresented entrepreneurs.
Jenny earned her J.D. from Yale Law School and a masters degree in City and Regional Planning from UC Berkeley.
She is the author of Raise Capital on Your Own Terms: How to Fund Your Business without Selling Your Soul.
Jenny co-founded the Sustainable Economies Law Center, the Force for Good Fund, and Opportunity Main Street.
X/Twitter Handle: @jennykassan
Personal Facebook Profile: facebook.com/jenny.kassan
Linkedin: linkedin.com/in/jennykassan
Instagram Handle: @thekassangroup
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If a location is not noted, the events below are virtual.
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Community Event Calendar
Successful Funding with Karl Dakin, Tuesdays at 10:00 AM ET - Click on Events.
Devin Thorpe is featured in a free virtual masterclass series hosted by Irina Portnova titled Break Free, Elevate Your Money Mindset & Call In Overflow, focused on transforming your relationship with money through personal stories and practical insights. June 8-21, 2025.
Join Dorian Dickinson, founder & CEO of FundingHope, for Startup.com’s monthly crowdfunding workshop, where he'll dive into strategies for successfully raising capital through investment crowdfunding. June 24 at noon Eastern.
Future Forward Summit: San Francisco, Wednesday, June 25 · 3:30 - 8:30 pm PDT.
Regulated Investment Crowdfunding Summit 2025, Crowdfunding Professional Association, Washington DC, October 21-22, 2025.
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