EPISODE · Nov 29, 2025 · 50 MIN
JF 4104: Raising Capital, Retaining Residents and Running Apartments the Right Way ft. Ed Mathews
from The Best Ever CRE Show · host Joe Fairless
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 MathewsCurrent role: Founder & CEO, Clark Street CapitalBased in: ConnecticutSay 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 Start earning passive income today at gsprei.com/bestever Alternative Fund IV is closing soon and SMK is giving Best Ever listeners exclusive access to their Founders’ Shares, typically offered only to early investors. Visit smkcap.com/bec to learn more and download the full fund summary. Join us at Best Ever Conference 2026! Find more info at: https://www.besteverconference.com/ Join the Best Ever Community The Best Ever Community is live and growing - and we want serious commercial real estate investors like you inside. It’s free to join, but you must apply and meet the criteria. Connect with top operators, LPs, GPs, and more, get real insights, and be part of a curated network built to help you grow. Apply now at www.bestevercommunity.com Podcast production done by Outlier Audio Learn more about your ad choices. Visit megaphone.fm/adchoices
What this episode covers
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 MathewsCurrent role: Founder & CEO, Clark Street CapitalBased in: ConnecticutSay 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 Start earning passive income today at gsprei.com/bestever Alternative Fund IV is closing soon and SMK is giving Best Ever listeners exclusive access to their Founders’ Shares, typically offered only to early investors. Visit smkcap.com/bec to learn more and download the full fund summary. Join us at Best Ever Conference 2026! Find more info at: https://www.besteverconference.com/ Join the Best Ever Community The Best Ever Community is live and growing - and we want serious commercial real estate investors like you inside. It’s free to join, but you must apply and meet the criteria. Connect with top operators, LPs, GPs, and more, get real insights, and be part of a curated network built to help you grow. Apply now at www.bestevercommunity.com Podcast production done by Outlier Audio Learn more about your ad choices. Visit megaphone.fm/adchoices
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JF 4104: Raising Capital, Retaining Residents and Running Apartments the Right Way ft. Ed Mathews
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