Navigating Transaction Pitfalls with Expert Advisors

In this episode, host Jeff Guylay is joined by guest Mark Achler, co-author of Exit Right, to explore the critical decision of whether—and when—to hire advisors during the M&A process. Drawing on lessons from the book and real-world experience, Jeff and Mark outline how CEOs can maximize value by assembling the right team of experts, while still retaining control over strategy, relationships, and execution. From bankers and attorneys to financial planners and tax professionals, this episode offers actionable insights on selecting advisors who align with your values and contribute meaningfully to successful outcomes.

What You’ll Learn in This Episode:

• The spectrum of advisors involved in a typical M&A transaction
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• Why hiring early—especially pre-LOI—creates leverage and unlocks value
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• How to avoid becoming overly dependent on advisors
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• The CEO’s role in maintaining judgment, relationships, and deal momentum
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• Why trust between parties is the foundation of successful dealmaking
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• How detailed LOIs and clear integration planning drive better outcomes
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• Real-world case studies showing how applying these principles boosted valuations

Key Discussion Points & Notable Quotes:

The Spectrum of Advisors in a Deal (00:43)

Mark and Jeff review the key players involved in M&A: attorneys, bankers, tax advisors, financial planners. Timing matters—especially when it comes to financial planning and structuring decisions.

“You want the best experts early—not just after the deal is done.” – Mark

The CEO’s Non-Negotiable Responsibilities (03:48)

Even with great advisors, CEOs must lead on strategy, decisions, and relationships.

“There are some things you just can’t outsource. You can’t outsource judgment or trust.” – Mark

The Importance of Trust in Getting Deals Done (05:46)

Advisors can facilitate—but it’s the trust between principals that often moves a deal forward.

“Trust is the lubrication that gets deals across the finish line.” – Mark

The Role of the Banker and the Importance of Timing (06:17)

A good banker understands the full arc of a transaction and helps prioritize forward-looking rationale over backward-looking valuation.

“We’re not just selling the past EBITDA—we’re building the case for future synergy.” – Jeff

When to Step in as a CEO (08:13)

The back-and-forth between attorneys can derail progress. CEOs must often step in to resolve what really matters.

“There’s always a point in a deal when someone has to say, ‘Enough—we need to solve this as principals.’” – Jeff

Detailed LOIs Preserve the Deal’s Integrity (10:41)

Without a clearly written LOI, sellers lose leverage and risk misinterpretation later.

“The minute you sign the LOI, you lose 90% of your negotiating leverage.” – Mark

“Our role as advisors is to make sure the LOI is translated accurately into legal documents.” – Jeff

The Case for the Right Advisor (13:18)

Not all advisors add value—some derail deals. Founders must choose those aligned with their values and goals.

“This is your baby. Choose someone who gets it, who gets you.” – Mark

“You’re essentially choosing a best friend for a very intense experience.” – Jeff

Real-World Success: A Valuation Doubled (18:54)

Mark shares a powerful case study of a founder who used the rationale framework to double their offer—by helping the buyer see the long-term potential.

“They shrugged and said, ‘We’re not paying you enough.’ That’s the Jedi mind trick.” – Mark

What Makes an M&A Outcome Truly Successful (23:31)

Success isn’t just the highest purchase price. It’s achieving the intent of the transaction—alignment, culture, growth, and impact.

“Think beyond the number. Think about the next chapter.” – Mark

Final Thoughts:

Hiring the right advisor can unlock enormous value—but only when paired with clear leadership from the CEO. This episode offers a roadmap for founders preparing to sell, highlighting how to build an aligned, expert team while maintaining ownership of the process. Deals aren’t just financial—they’re personal, strategic, and long-term. The right partner makes all the difference.