In the transformative realm of real estate investing, few narratives are as compelling as Ed Mathews’. From a Silicon Valley startup connoisseur to a distinguished real estate investor, Ed's journey offers a wealth of insights. In this episode of the Raising Private Money podcast, Ed Mathews shares his experiences and strategies for succeeding in multifamily property investing, along with key takeaways for both active real estate enthusiasts and passive investors.

Building a Foundation: Early Influences and Initial Hesitation

Ed Mathews’ relocation from Boston to Connecticut in 2008 was a pivotal event, driven by familial priorities. While the move brought him closer to his extended family, it also set the stage for his real estate venture. However, despite favorable market conditions from 2008 to 2011, Ed found himself paralyzed by fear and what-ifs. It wasn’t until he met Amy Rio, a determined real estate broker, that he took the plunge. Amy’s insistence led to the purchase of a 4-unit property for $99,000—a decision that Ed marks as a turning point in his real estate career.

Overcoming Fear and Embracing Courage

Ed candidly discusses how the fear of financial commitment often holds people back from potential opportunities. He references Tony Robbins' philosophy, highlighting how decisions are often driven by either the pursuit of pleasure or the avoidance of pain. For Ed, the need to escape the conventional 40-year career path provided the necessary push. His mantra, drawn from a coach named Crystal and a friend, Chris Moore, centers on getting comfortable with discomfort—a critical element for growth and success in any endeavor.

Building Trust with Lenders and Investors

Trust forms the backbone of Ed Mathews’ strategy for raising private money, an area where he has excelled, having raised $5 million for multifamily properties. Ed stresses understanding the lenders' needs and goals, focusing on offering opportunities that align with their investment objectives. By fostering personal relationships and maintaining transparency, he has turned potential collaborations into lasting partnerships, successfully raising a million dollars in private money along the way.

Transitioning from Tech to Full-Time Real Estate

Before becoming a full-time real estate investor in 2018, Ed had a rich career in Silicon Valley, amassing over 24 years of experience. The realization that his real estate income outpaced his tech salary catalyzed his full transition. Founding Clark Street Capital marked a new chapter, enabling him to focus on helping business owners and executives transition away from traditional careers through lucrative real estate investments. His background in startups and crowdfunding also positioned him to leverage unique strategies for raising capital.

Strategic Fit and Abundant Mindset

One of Ed’s guiding principles is prioritizing quality investments over sheer volume. He ensures that each deal fits his clients' models, thus fostering trust and long-term satisfaction. Ed’s abundant mindset—a belief that ample opportunities exist for everyone—differentiates him in a competitive field. He is open to sharing insights and making connections, reflecting a community-driven approach that benefits all parties involved.

Innovative Funding Models and New Projects

Clark Street Capital’s latest venture, a debt fund, epitomizes Ed's innovative approach. By offering loans at a 12% interest rate with upfront points, he creates a reliable cash flow stream while maintaining trust with flippers, rehabbers, and small multifamily investors. This strategy is reminiscent of selling tools during a gold rush—providing essential resources to those actively engaged in the field.

Additionally, Clark Street Capital is spearheading a 100-unit affordable housing project in Central Connecticut. Amid a significant housing shortage, this