Scaling the Gap Ep 60 | Maximizing Business Value: Insights on Mergers and Acquisitions with Dena Jalbert

In this episode of Scaling the Gap, Madeleine MacRae sits down with Dena Jalbert, CEO of Align Business Advisory Services, for a deep dive into the world of mergers and acquisitions (M&A) for founders and family-owned businesses. Dena unpacks the emotional and strategic challenges of selling a business, stressing the importance of planning ahead, staying true to core values, and finding the right buyer.

The conversation goes beyond numbers, touching on the evolving M&A landscape and the power of intentionality in business transitions. Madeleine and Dena explore the role of integrity, trust, and the joy of helping clients succeed. Madeleine shares her passion for negotiation and the balancing act of staying authentic, while Dena emphasizes the value of "entrepreneurial street smarts."

Together, they reflect on lessons learned—shifting from corporate to entrepreneurial hiring, redefining success beyond financial gain, and the importance of service, diversity, and innovation in business. The episode wraps up with a powerful takeaway: success isn’t one-size-fits-all—it's about defining it on your own terms.

Key Takeaways

• Mergers and acquisitions (M&A) in the context of founder and family-owned businesses.
• The unique characteristics and significance of the middle market in business transactions.
• The emotional challenges faced by business owners when selling their companies.
• The generational shift in business ownership and its implications for exit strategies.
• The importance of planning for value extraction well in advance of a sale.
• Aligning personal values with potential buyers during the M&A process.
• The role of specialized guidance in navigating business transitions.
• The evolution of M&A practices and the focus on smaller deals post-financial crisis.
• Viewing M&A as an opportunity for growth rather than an endpoint.
• The necessity of strategic planning and exploring diverse exit options for business owners.

In This Episode

• [00:00:58]   Introduction to Dena  
• [00:04:52]   Shifts in M&A focus  
• [00:06:52]   Understanding transactions  
• [00:09:35]   Impact on families  
• [00:10:18]   Planning for retirement  
• [00:12:08]   Value extraction importance  
• [00:13:05]   Planning for a successful exit   
• [00:15:06]   Concerns about ownership change  
• [00:16:04]   Finding the right partner     
• [00:20:00]   Emotional turmoil in M&A   
• [00:21:30] M&A misconceptions  
• [00:22:43] Evolution of M&A practices  
• [00:22:56]  Access to resources   
• [00:25:51] The Cheesecake Factory metaphor   
• [00:27:20] Challenges of entrepreneurship  
• [00:35:39] Defining success
• [00:44:45] Final thoughts and call to action

Notable Quotes

• (00:12:08) "I saw, I observed it happen again and again and again, where I said, 'Oh, whoa, whoa, whoa, like that can't be the case, right? We have to get the good word out there that it does take a little bit more planning.'" — Madeleine
• (00:17:08) "You didn't have a partner, and partnership is an active verb in this case, not just an individual. You have to take active engagement in that, and so it's strategic, it's not by accident." — Dena
• (00:17:54) "I want someone who knows me deeply to help me when I'm ready. I'm not going to start drilling my own teeth, so why would I not entrust my life's work to a specialist?" —...