Shayn Diamond cares more about the people behind a startup than a polished pitch, believing the real question is who you're building with, and he'd rather have an honest, off-the-cuff conversation than sit through a rehearsed presentation. Before moving into venture capital, he worked as a corporate lawyer handling real estate and M&A deals, giving him a legal and cross-disciplinary background—law, an MBA, and philosophy—that also shapes how closely he watches timing and adoption in proptech.