During the 1990’s the market for initial public offerings was very strong setting new records for not only the shear number of IPO’s, but also the level of underpricing. After the Internet Bubble burst in 2000, there has been steady research interest in initial public offerings (IPOs) by both finance and strategy researchers. The study takes a different approach to the relationship between issuers and underwriters and focuses on the pairings of issuers and underwriters at the deal level instead of at the firm or industry levels. The theory presented here suggests that there are stronger and weaker issuers, as well as stronger or weaker underwriters measured by their resource contributions and peers. In situations where strong underwriters bring weak issuers to market, underpricing is significantly higher than when the strengths are equal. Conversely, when weaker underwriters bring stronger issuers to market the level of underpricing is significantly less. These results suggest that an issuer’s choice of underwriter can substantially effect the firm’s IPO proceeds, and that issuers should look for an underwriter with a similar level of strength, rather than the conventional wisdom to contract with the strongest underwriter that agrees to take the firm public.