Jessica Lessin, founder and C.E.O. of The Information, joins Dylan for a candid conversation about how The Information has thrived and remained profitable after 11 years, why deep expertise and loyal audiences are more important than chasing scale, and her approach to backing sharp-minded entrepreneurs through recent investments in Semafor, The Ankler, and others. Jessica also weighs in on how Silicon Valley’s power players are recalibrating in the era of Trump 2.0.