Before he became some sort of ill-defined entrepreneur/investor he used to talk knowledgeably and enthusiastically online via a podcast (or possibly several) ab

Before he became some sort of ill-defined entrepreneur/investor he used to talk knowledgeably and enthusiastically online via a podcast (or possibly several) about wine, which was his family's business - this was probably a decade or more ago. Since then I guess you could describe his career as having "sprawled".