The Best Ever CRE Show JF 4104: Raising Capital, Retaining Residents and Running Apartments the Right Way ft. Ed Mathews
Nov 29, 2025
Ed Mathews, Founder and CEO of Clark Street Capital, shares his transformative journey from Silicon Valley tech executive to multifamily real estate investor. Motivated by family time, he scaled his portfolio by building trust with contractors and implementing robust systems. Ed emphasizes the importance of retaining long-term residents for better returns and discusses how AI is revolutionizing his operations. He also reveals his strategic shift to asset management and his plans for a debt fund and private equity fund to target larger acquisitions.
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Leaving Corporate To Buy Time
- Ed Mathews left a high-flying DocuSign career after missing family moments and focusing on real estate full time in 2018.
- He built his portfolio by flipping houses and buying small multifamily properties while keeping his W-2 income initially.
Bootstrap Then Raise To Scale
- Fund your first deals with savings or commissions if you can to learn the operating playbook firsthand.
- Then raise outside capital to scale faster and allow others to participate in the upside.
Hire By Audition With Small Projects
- Start small and give contractors incremental responsibility to audition them on real work.
- Hand trusted contractors keys and scopes, then let them run projects within clear budgets and risk limits.
