Len Jordan spent 16 years running product and platform teams in software before moving into venture, which shows up in how practical his advice is—he coaches founders to test out independent board members as advisors first, keep early boards small, and look for people who keep finding new opportunities rather than sticking rigidly to an original plan, a view he sums up by saying "the average of two strategies is not a strategy." He also tends to invest through relationships built over years, following people he's worked with before into new companies, and splits his attention between two different kinds of startups: software and analytics that modernize old, messy industries like auto repair, and consumer products that change how people see, hear, or feel.