

Ep 485 After the Deal: The Psychology of Selling—Kill Criteria, Walkaway Mindset & Why “Telling Your Company’s Story” Often Drives Up Your Multiple
28 snips Mar 14, 2025
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.
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Drip's Origin and Growth
- Rob Walling built Drip, a SaaS email marketing automation tool, initially as a side project.
- It grew quickly, becoming one of the top 10 fastest-growing email service providers.
Selling Your Company: A One-Way Door
- Selling a company is a one-way door decision with significant implications, similar to getting a divorce.
- Take considerable time to reflect and consider long-term goals before making the decision.
Identifying Serious Buyers
- Look for buyers who express interest even when you state your company is not for sale.
- This signals they're willing to pay a premium, indicating a potential good multiple on the sale price.