Ep 485 After the Deal: The Psychology of Selling—Kill Criteria, Walkaway Mindset & Why “Telling Your Company’s Story” Often Drives Up Your Multiple
Mar 14, 2025
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Rob Walling, a serial entrepreneur and TinySeed founder, and Dr. Sherry Walling, a clinical psychologist and mental health advocate for entrepreneurs, delve into the psychology behind selling businesses. They explore crucial concepts like kill criteria, the emotional rollercoaster of exits, and the importance of personal storytelling in boosting company value. Their insights highlight how emotional preparation and strategic planning can distinguish thriving exits from those that leave owners lost. Additionally, they discuss celebrating personal milestones and the significance of financial literacy for future generations.
Establishing 'kill criteria' helps entrepreneurs determine when to exit a business by assessing specific milestones and realistic goals.
The 'walkaway mindset' empowers founders during negotiations, ensuring they remain unattached to offers that don't align with their core values.
Taking time to celebrate post-exit accomplishments is crucial for entrepreneurs to process their identity shift and avoid existential uncertainty.
Deep dives
Understanding Exit Strategies
The episode discusses the concept of exit strategies for entrepreneurs, emphasizing the need to understand when it's time to sell a business. Key insights include developing 'kill criteria'—specific metrics or milestones that indicate when to exit a venture. This involves assessing realistic goals, such as reaching a certain annual revenue, and setting a timeline to evaluate progress. These predetermined exit points can help entrepreneurs make more calculated decisions rather than impulsive ones driven by burnout or frustration.
The Walkaway Mindset
Having a 'walkaway mindset' is crucial during the negotiation process when selling a company. This mindset empowers founders to remain independent and not get emotionally attached to potential offers, reminding them that they must be willing to walk away if terms do not align with their core values. Establishing clear expectations for employee retention and brand integrity can protect personal and company values during a sale. When entrepreneurs maintain this perspective, they often secure better deals, not settling for less than they are truly worth.
Celebrating Your Accomplishments
Following an exit, it's essential for entrepreneurs to take the time to celebrate their accomplishments rather than immediately rushing into the next challenge. This celebration acts as a recognition of hard work, allowing for mental closure on a significant chapter of their career. Without acknowledging this milestone, entrepreneurs risk falling into existential dread and misunderstanding their purpose after exiting. Establishing rituals or personal symbols can help reinforce this celebration, creating a tangible reminder of their journey.
Navigating Post-Exit Emotions
The emotional aftermath of selling a business can be tumultuous, characterized by feelings of loss and uncertainty about the future. Entrepreneurs may experience a profound identity shift, as their personal and professional identities have often become intertwined with their business. It's common for individuals to grapple with questions about their purpose or direction after the sale. Engaging in reflection, therapy, or productive hobbies can aid in sorting through these feelings, helping them reinvent themselves as they embark on a new phase.
Managing Financial Changes
After selling a business, significant financial changes come into play, requiring entrepreneurs to revise their relationship with money. Many founders may struggle with newfound wealth, oscillating between being overly frugal or spending without discretion. It becomes essential to develop a new financial strategy that emphasizes making money work for them rather than just accumulating wealth. By focusing on personal finance education and making thoughtful decisions, entrepreneurs can establish a stable financial future while enjoying the fruits of their labor.
For the first time ever, we recorded a Built to Sell Radio episode in front of a live audience at the Value Builder Summit—a gathering of mission-driven advisors dedicated to helping founders level the playing field as they approach their exit.
Rob Walling has started, built, and sold multiple companies. As an investor and conference organizer, he’s seen hundreds of founders exit—some thriving, others struggling. He teamed up with Dr. Sherry Walling, a clinical psychologist specializing in supporting entrepreneurs, to codify what separates a successful exit from one that leaves an owner adrift. Their insights culminated in their new book Exit Strategy.
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