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About Opportunity Main Street

Opportunity Main Street, LLC is part of an ecosystem of social enterprises working to  make finance regenerative, accessible, democratic, and socially just

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Our Theory of Change

Almost every program that promises access to capital for small businesses falls far short of its promises.  These programs may provide introductions and opportunities to pitch to banks, angel investors, and VCs, but very little money actually flows to the participants.

This is because these sources of funding are the wrong fit for the vast majority of small business owners.  Most small business owners need access to patient, supportive funding that does not require them to comply with strict covenants, make onerous monthly payments, or try to become the next unicorn.

The best source of investment capital for these businesses is the vast untapped pool of individual, non-professional investors who currently invest most of their capital in the stock market.


If metro Baltimore households shifted just one percent of their investments to local business, that would be an infusion of over $26 billion of investment capital.


And Baltimore has already demonstrated its willingness to invest in local business!  Our partner organization, Community Wealth Builders, has supported over 70 businesses with Reg CF campaigns to raise nearly $4.8 million from roughly 10,250 small investors.  The vast majority of these businesses (89%) are owned by people of color.


The failure of existing capital markets to meet the needs of small, local and minority-owned businesses in Baltimore underscores the need for a new tool like investment crowdfunding to finally move the needle on access to supportive capital for underrepresented entrepreneurs.

Unlike other sources of capital, women and people of color have greater success with investment crowdfunding than their white male counterparts.

According to a recent report by Crowdfund Capital Advisors, 81% of all women and minority offerings were successful in their funding rounds in comparison to an industry average of 69%. Startups with minority founders received 25.4% of dollars invested in Reg CF equity deals in 2022.

Our goal is to provide an ecosystem of support so that underrepresented entrepreneurs can successfully reach their funding goals using Regulation Crowdfunding and do it in a way that is legally compliant and designed to be in alignment with their long term needs and goals.  For those that achieve this, Opportunity Main Street will provide access to follow on funding in larger amounts from its impact investment fund.

Meet The Team

Michelle Thimesch is a licensed business and securities lawyer who has worked with closely held small businesses for more than two decades. In this role, she has focused on finance for growth and succession planning.

Michelle served as the lead on the coordination of accountants, financial planners, and in-house counsel to facilitate a smooth succession plan for the small businesses she counseled. As part of this process, she became a certified community mediator and business coach to understand the interpersonal and communications challenges that arise when high stakes, emotionally charged transitions are undertaken.

Michelle has been an investor in alternative assets over this same period and has seen first-hand the financial and social benefits of direct investments. In 2014, Michelle went from passive prosocial investment to an active project management role in the development of affordable housing units implementing sustainable construction methods. She introduced a building system to the community of Richmond, CA and built the first two steel frame and ESP foam houses in that city. A local affordable housing developer has adopted this system and implemented an apprenticeship training program that creates high-paying jobs for disadvantaged young adults and formerly incarcerated individuals.

Michelle received her bachelor’s degree in Speech Communication from the University of Illinois at Urbana-Champaign and attended Drake University Law School.

Jenny Kassan has over 25 years of experience as an attorney and advisor for mission-driven enterprises. 

She is the author of Raise Capital on Your Own Terms: How to Fund Your Business without Selling Your Soul (Berrett-Koehler, October 2017).

Jenny earned her J.D. from Yale Law School and a masters degree in City and Regional Planning from the University of California at Berkeley.

Jenny co-founded the Force for Good Fund, an impact investment fund managed by Community Ventures, a nonprofit organization that Jenny founded in 2008.

Jenny’s legal practice, The Kassan Group, provides legal services, coaching, and consulting for mission-driven companies, investors, and intermediaries.

Jenny served on the Securities and Exchange Commission Advisory Committee on Small and Emerging Companies. She submitted the petition to the SEC that led to the passage of the 2012 JOBS Act and was present at the White House signing ceremony.

Before becoming a securities lawyer, Jenny worked for eleven years at a nonprofit community development corporation in Oakland called the Unity Council.

Jenny co-founded the Sustainable Economies Law Center, a nonprofit that provides legal information to support sustainable economies.  Jenny is also a fellow at Democracy Collaborative.  She is on the board of directors for CfPA (Crowdfunding Professional Association).

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