10 Things Nobody Tells You About Selling Your Business
Learn the ten critical questions and hidden challenges behind successfully exiting a business, from tax liabilities and forced exit triggers to post-sale identity.
About This Video
Executive Takeaways
- Approximately 70% of business owners who attempt to sell their companies never actually complete a sale.
- A viable exit requires building an independent business rather than selling a founder-dependent job.
- Unprepared founders face massive seven-figure tax liabilities, overlooked real estate entanglements, and lack the advisory team needed to navigate the sale.
- Owners must prepare for forced exit triggers (the five D's) and establish their target financial number well ahead of going to market.
- Post-exit psychological preparation is essential to navigate the loss of identity and purpose that often follows a major liquidity event.
Key Questions Answered in This Deep Dive
Why do 70% of business owners fail to sell their companies?
Most businesses fail to sell because they are overly dependent on the founder's daily operations, lack formal advisory teams, or are not properly structured to provide standalone enterprise value.
What common tax and structural mistakes do founders make during an exit?
Founders frequently fail to plan for seven-figure tax bills, neglect to properly integrate company-owned real estate into deal terms, and overlook wealth protection strategies for family or employee ownership options like ESOPs.
What are the five D's that force an unexpected business exit?
The five D's refer to unexpected life and business events—such as death, disability, divorce, disagreement, and distress—that can force an owner to exit on unfavorable terms if contingency plans are not in place.
Why do founders experience an identity crisis after selling their business?
Many founders tie their purpose and personal identity entirely to running their company, leading to severe regret and a sense of loss once the transaction closes and operational control is handed over.
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