
Built to Sell Radio Ep 470 After the Deal: James Ashford on the Aftermath of Selling a 12-Employee Company for 8 Figures
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Nov 29, 2024 James Ashford, founder of GoProposal and seller to FTSE 100 company Sage, shares his journey of navigating life after a successful business sale. He discusses the emotional challenges and surprises of post-exit life, including the identity crisis faced by entrepreneurs. James reflects on the shift from entrepreneur to corporate ambassador and the deep personal growth that comes from embracing lifelong learning. He emphasizes the importance of understanding your new corporate environment while also revealing the emotional toll entrepreneurial success can impose on personal relationships.
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Playing Not to Lose
- After selling GoProposal, Ashford shifted from "playing to win" to "playing not to lose."
- He worried about getting fired, even for minor infractions like oversharing deal details on a webinar.
Corporate Conservatism
- Large companies tend to be conservative, prioritizing not losing over winning.
- This can create a risk-averse environment that stifles entrepreneurial spirit.
Data-Driven vs. Gut Decisions
- Ashford found large companies rely heavily on surveys and data, even for minor decisions.
- He contrasted this with his entrepreneurial approach of trusting his gut and taking action.








