How Scott Galloway’s Tough Morgan Stanley Start Fueled His Drive to Entrepreneurship

Scott Galloway’s narrative about his experience in investment banking provides a nuanced view of both the costs and benefits of entering a high-intensity finance role early in one’s career. His memories of working at Morgan Stanley—proofing prospectuses late into the night, coping with insecurity over peer promotions, and dealing with senior executives—paint a picture far removed from the romance typically attached to finance careers. The work was “incredibly boring” and often thankless, he says, yet it forced him to acquire skills that he later found instrumental.

Those skills—attention to detail, discipline under pressure, and managing ego-laden professional environments—are frequently cited in talent development literature as differentiators among early-career professionals. In Galloway’s case, even though he disliked the environment deeply, he believes those experiences helped him clarify what he did not want to do, which became equally important to realizing what he did want to do—entrepreneurship.

Of particular note is how Galloway recognized a mismatch between his personality and what investment banking demanded. Insecurity over perceived incompetence in others, discomfort in hierarchical settings, resistance to internal politics—these are traits he identified as incompatible with long-term corporate life. That level of self-awareness is rare, and it informed his decision to leave despite having a role that many would consider secure and prestigious.

Strategically, his story suggests that early-career professionals should treat roles in banking not necessarily as endpoints, but as accelerators: try them, extract the skills, assess the fit, and move on if needed. For firms, the implication is also clear: the traditional pathway from analyst to executive may be becoming less compelling, especially as costs of education and alternative paths increase the opportunity cost associated with formative banking roles. Galloway himself has observed that the value proposition of investment banking as legacy entry points has eroded due to MBA tuition inflation and expectations that senior roles will absorb responsibility without corresponding reward. [7]

There are several open questions arising from this analysis. First: how macro trends—such as rising educational costs, shifting norms around work-life balance, and diminishing returns in certain finance specializations—affect the perceived attractiveness of banking as a “safe bet.” Second: whether alternative experiential paths, such as early-stage startups, tech, or specialized boutiques, can replicate the skills and exposure that mega banks historically delivered. Lastly: for firms, how attrition driven by personality misfit will increase transactional and reputational cost unless mentorship, role flexibility, and internal path clarity improve.