Not every particle that forms a nematic liquid crystal makes a smectic. The particle tip is critical for this behavior. Ellipsoids do not make a smectic, but spherocylinders do. Similarly, only those N-CB alkylcyanobiphenyls with sufficiently long (N≥8 carbons) alkane tails form smectics. We understand the role of the particle tip in the smectic transition by means of a simple two-dimensional model. We model spherocylinders by "boubas" with rounded tips, and ellipsoids by "kikis" with pointed tips. The N-CB molecules are modeled by a small body with a polymer tail. We find that rounded tips and longer polymer tails lead to a smectic at lower densities by making the space between layers less accessible, destabilizing the nematic.