Ed Mathews Founder, Elevista | Founder, Clark St Capital | Host, Real Estate Underground Ed Mathews spent 24 years in B2B software before he picked up a hammer. Senior roles at Ariba, Coupa, Scanmarket, and DocuSign taught him how to build systems that scale and hold teams accountable when missing wasn't an option. Real estate started as a side project. In 2011, after analyzing 1,100 deals and freezing on every one, a broker named Amy Rio made him finally sign a contract on the hood of his truck. The four-unit cost him $99,000. He sold it thirteen years later for $415,000. The lesson wasn't the deal. It was getting out of his own way. For seven years he ran the portfolio between sales calls and 100,000+ miles of annual travel. In February 2018, he left DocuSign and went full-time. Cl...