PurposeThis study considers a contracting problem between a fairness concerned entrepreneur (EN) and a fair-neutral venture capitalist (VC) to explore the effects of asymmetry, agency conflicts and fairness concerns.Design/methodology/approachThe authors construct the model by assuming the EN's risk aversion degree is private information, which is more realistic but ignored in most studies. Under the principal–agent framework, the authors solve the VC's optimal contracting models by identifying the ranges of feasible solution, where the optimal solutions of these models are explicit and nicely reconcile the “private equity” puzzle. Moreover, validity of the optimal solutions is verified by numerical simulations.FindingsIn accordance with empirical evidence, information asymmetry lowers the optimal equity share that the VC provides to EN but raises EN's profit due to lower effort disutility and information rent. Moreover, the authors find that the fairness concerns is beneficial for the EN, where it not only increases the EN's optimal equity share, but also enhances the certainty equivalence of the EN's utility regarding its profit. Relative to the benchmark model where the EN's risk aversion degree is common knowledge, the EN's efforts recommended by the optimal contract is less sensitive to the EN's fairness concerns degree when the EN does not actually announce its risk aversion degree.Originality/valueFirst, the authors incorporate asymmetry to study a two-period contracting problem and explore how it affects the equity shares allocated to the contractual parties. Second, the authors incorporate fairness concerns and analyze its effect regarding the decision-makings and profits.