John Casmon interviews Ed Mathews, a former Silicon Valley tech executive who walked away from a high-flying software career to build a more family-centered, freedom-focused life through real estate. Ed shares how missing too many “18 summers” with his daughters pushed him to leave DocuSign and go all-in on multifamily after seven years of flipping houses and small-building rehabs on the side. He explains how he scaled his Connecticut portfolio by finding “rock star” contractors through trade-to-trade referrals, building tight systems, and using process—not heroics—to let average people perform exceptionally well. Ed details why he prefers long-term residents over constant value-add turnover, how he achieved 4.2-year average stays, and why responsiveness, respect, and presence on site drive both mission and NOI. The conversation closes with his shift away from property management toward asset management, his expansion into AI-powered operations, and the launch of both a debt fund and private equity fund to pursue larger 150-unit-plus acquisitions.
Ed Mathews
Current role: Founder & CEO, Clark Street Capital
Based in: Connecticut
Say hi to them at:
Website: https://www.clarkst.com
Phone: (860)675-5800]
YouTube: https://www.youtube.com/@clarkstinvestorsacademy
Podcast: https://www.clarkst.com/podcast
LinkedIn: https://www.linkedin.com/company/clark-st-capital
Twitter: https://twitter.com/clarkstcapital1
Facebook: https://www.facebook.com/ClarkStCapital
Instagram: https://www.instagram.com/clarkstcapital
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