Tom Totten, an actuary and serial entrepreneur, shares his journey from a defined benefit consultant to advising companies on Employee Stock Ownership Plans (ESOPs). The conversation delves into the intricacies of ESOPs, their guarantees, and the liquidity risks associated with them. Tom discusses the purpose of lifetime income strategies, including the use of annuities, and reflects on the evolving relationship between employers and employees in the context of retirement planning. In this conversation, the speakers discuss the benefits of including lifetime income solutions in retirement planning, emphasizing the role of the workplace in providing these solutions. They explore the challenges of communicating the value of lifetime income to pre-retirees and retirees, the impact of technology on retirement planning, and the benefits of diversification in investment strategies. The discussion also touches on the potential of ESOPs as a means of wealth creation for employees and the evolving landscape of retirement planning in light of alternative investments.