Living with Intention - A.J. Wasserstein – Entrepreneur, Investor, and Yale SOM Professor
Mar 28, 2024
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Entrepreneur and Yale SOM Professor A.J. Wasserstein shares insights on dividing life into thirds, the evolution of leadership, and the emotional experience of selling a business. Topics include becoming an empty nester and transitioning to teaching, emphasizing work-life balance and holistic success.
Life divided into thirds offers insightful reflections on different life stages and transitions.
Selling a business brings validation and liquidity but also reveals the challenging reality of entrepreneurship.
Evolution of leadership style emphasizes continuous learning, growth, and reflection on past mistakes.
Transitioning from accumulation to serving highlights the joy found in teaching, mentoring, and guiding the younger generation.
Deep dives
Reflecting on the Process of Selling a Business
Selling the business brought validation and the conversion of illiquid to liquid currency, yet it was described as a miserable and depressing process by the speaker. The dirty secret in entrepreneurship was highlighted, contrasting the celebratory storytelling in media and academia against the gritty reality of selling a business.
Dividing Life Into Thirds
AJ Wasserstein discussed the concept of life divided into thirds, reflecting on the stages zero to 30, 30 to 60, and beyond. The importance of protecting time, contemplating the last chapter, and dealing with various life phases such as empty nests and elderly parent care were emphasized.
Lessons from Early Entrepreneurial Years
The speaker recalled early signs of entrepreneurship from childhood, influenced by discussions around business concepts at home. Starting the first business at 24 was deemed both surprising and reflective, highlighting a journey of persistence, self-discovery, and gradual progress in the entrepreneurial realm.
Challenges and Evolving Leadership Skills
The transition from a shopkeeper to a leader was discussed, emphasizing the complexities of hiring, leading, and motivating individuals as a young emerging leader. The evolution of leadership style over time, reflection on past mistakes, and continuous learning through experiences and mentorship were key points.
Navigating Transitions: Succeeding Beyond Business Exit
Post-exit reflections on the emotional turmoil, loss of identity, and challenges faced after selling a business were shared. The concepts of 'arrival fallacy' and the need for intentional transitions and reflection post-exit were highlighted, advocating for pausing, reflecting, and exploring new paths with trial probes.
Embracing Teaching and Service
Transitioning from accumulation to serving, the joy and fulfillment found in teaching and mentoring were emphasized. The speaker's shift towards inspiring and guiding the younger generation, seeking to instill not only business acumen but also crafting extraordinary lives, was highlighted as a purposeful and valuable passion.
Acknowledging Mentorship and Balanced Living
Mutual admiration for mentorship was expressed, with the speaker commended for embodying a holistic approach to success, balancing various life facets such as community involvement, family, and business endeavors. The importance of conscious efforts to build a balanced life and value all significant aspects was underscored.
My guest today is A.J. Wasserstein, the Eugene F. Williams, Jr. Lecturer in the Practice of Management at the Yale School of Management where he teaches multiple classes on the topics of entrepreneurship through acquisition and small company leadership.
A.J. previously was the president of Onesource Water, the third-largest bottleless water service business in the U.S. and the founder and CEO of ArchivesOne, the third-largest records management company in the U.S., which he sold to Iron Mountain after 17 years of operation. Among the topics we discuss in this episode are looking at life in thirds, the importance of protecting your time, and what it felt like to sell the company he founded.
(00:16:36) - How has your idea of leadership evolved over your career?
(00:24:56) - The experience of selling a business you founded
(00:38:16) - Becoming an empty nester
(00:46:52) - AJ’s Third third of life
The content of this podcast does not constitute investment advice, an offer to provide investment advisory services, or an offer to sell or solicitation of an offer to buy an interest in any investment fund.
