Summary In this two part episode, the guests discuss the considerations and communication strategies involved in a family business deciding to sell their business. They emphasize the importance of open and proactive communication within the family system, as well as with external shareholders and the C-suite. The guests also highlight the significance of early planning for the post-sale phase, including identifying purpose and impact beyond the business. They stress the need to address potential regrets and ensure a smooth transition to life after the sale. This conversation explores various aspects of transitioning from a family business to a family office. The speakers discuss the importance of understanding one's skills and talents and how they can translate into new domains. They emphasize the need for careful planning and decision-making, as well as the potential challenges of sudden wealth. The speakers also highlight the value of collaboration and a holistic approach, considering both individual and collective philanthropy. They stress the significance of exploring purpose and impact beyond the sale of the business and the importance of capturing family stories and history. Takeaways Open and proactive communication is crucial within the family system and with external stakeholders during the decision-making process and after the sale. Early planning for the post-sale phase, including identifying purpose and impact beyond the business, is essential. Considerations for each group of stakeholders, such as family members who own the business but don't work in it, should be taken into account. Avoiding regret of selling the business involves understanding personal goals and needs, planning for the day after the sale, and addressing emotional and financial aspects. Preparing for life after the sale includes exploring new opportunities, seeking professional advice, and maintaining open-mindedness. Understand your skills and talents and how they can translate into new domains. Take time to plan and make wise decisions, avoiding impulsive actions. Consider the merits of earnouts as part of a transition. Explore individual and collective philanthropy, finding the right balance. Start early with transition planning and engage in open and honest family conversations. Blend for-profit and non-profit activities to create a unified approach. Capture family stories and history to preserve legacy and values. Chapters 00:00 Introduction and Guest Introductions 04:03 Considerations in Family Discussions Leading to the Decision to Sell 08:24 The Role of Philanthropy and Impact in the Sale Process 11:16 Importance of Communication within the Family System 17:36 Effective Communication with External Shareholders and C-Suite 21:52 Considerations for Each Group of Stakeholders 27:29 Effective Communication Internally and Externally 36:39 Avoiding Regret of Selling the Business 42:21 Preparing for Life After the Sale 52:56 Understanding Skills and Talents 55:31 Transitioning to a Family Office 56:24 Managing Sudden Wealth 57:18 Taking Time to Plan 58:41 Dealing with External Pressure 59:30 Hiring the Right Expertise 01:00:02 Avoiding Impulsive Decisions 01:01:24 The Merits of Earnouts 01:04:01 Exploring What's Next 01:05:02 Collaboration and Holistic Approach 01:08:38 Discovering Purpose and Impact 01:11:15 Balancing Individual and Collective Philanthropy 01:19:36 Transitioning Identity and Purpose 01:23:22 Exploring Family Dynamics 01:29:11 Start Early with Transition Planning 01:32:05 Blending For-Profit and Non-Profit 01:35:29 The Power of Storytelling and Family History