In Part 2 of Why You Should Buy a Business Instead of Starting One with Jory Evans, we move past the mechanics of deal-making and into the high-stakes world of execution. Jory Evans, CEO of Evans Trucking, explains why acquisitions succeed or fail not in the negotiation room, but in how leaders handle the transition afterward. He highlights the importance of logistics, leadership depth, and cultural alignment, drawing from his own experiences of scaling Evans Trucking through multiple acquisitions. Jory breaks down how leadership voids, communication breakdowns, and rushed software or process changes can destabilize both the company being purchased and the buyer’s existing business.

This episode also digs into the human side of acquisitions—the trust between buyer and seller, the role of vendor financing in ensuring alignment, and the delicate process of retaining key staff and customer relationships. Jory shares candid stories of successes and setbacks, illustrating why over 60% of acquisitions fail and how entrepreneurs can avoid becoming part of that statistic. For anyone looking to grow through acquisitions, this conversation offers a blueprint for building a solid execution plan, managing risk, and leading with trust to ensure long-term success.

Key Takeaways:

1. Closing the deal is only the beginning—execution is where acquisitions succeed or fail.

2. Leadership depth matters; a thin or tired team can derail integration.

3. Culture fit is critical—clashing values can destroy even the best-looking deals.

4. Retaining staff and relationships is often more valuable than the assets you purchase.

5. Logistics like communication, proximity, and software transitions can make or break efficiency.

6. Trust between buyer and seller is essential—without it, lawyers and accountants can tear a deal apart.

7. Vendor financing keeps sellers invested in your success, making transitions smoother.

8. Over 60% of acquisitions fail because companies ignore the human and cultural side of integration.

9. Always have a leadership plan to fill voids quickly when owners or key people exit.

10. Stay unemotional, follow the process, and be willing to walk away if red flags appear.