Reverse diligence and cultural evaluation

M&A isn't just about closing deals, it's about making the deal actually work.

Carlos Cesta, M&A advisor and founder of his own boutique advisory practice, spent 30 years on the buy-side at Verizon, Dentsu, Presidio, and NP Digital. He's worked 125+ deals across telecom, advertising, and digital marketing. Now he's flipped to advisory, bringing that buy-side operator mindset to entrepreneurs preparing for exit.

In this episode of the M&A Science Podcast, Carlos Cesta, Partner at Makanta Services, breaks down how seasoned buyers really think about M&A. Not as a linear process, but as a series of decisions that constantly reshape one another.

Carlos shares why strategy is as much about what not to pursue, and he also explains why one-size-fits-all deal templates fail, how earnouts are often misused, and what experienced buyers do differently to protect value after closing.

Things You'll Learn:

• Why M&A strategy also means defining what you WON'T buy
• The deal spiral model experienced buyers use
• How to start integration planning before LOI
• How to structure earnouts that actually work
• Using deal structure earnouts as a risk management tool

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[00:03:34] Carlos Cesta Background – 30 years in corporate development across Verizon, Dentsu, Presidio, and NP Digital with 125+ deals executed.

[00:05:27] Standing Up M&A from Zero – What it really takes to build an M&A function when no corporate development muscle exists.

[00:09:32] Strategy Before Transactions – Why defining what NOT to buy is more important than chasing opportunistic deals.

[00:11:05] Programmatic M&A Through Cycles – How repeatable, strategy-led M&A creates value across economic and technology shifts.

[00:14:21] Blending Venture and M&A Thinking – Using VC-style investments to manage disruption and future-proof acquisition strategy.

[00:17:23] The Deal Spiral Framework – Why deal structure, diligence, and integration must evolve together, not linearly.

[00:21:57] Designing the End State First – Starting with culture, leadership, and go-to-market alignment before signing an LOI.

[00:30:21] Creative Earnout Engineering – Structuring earnouts to de-risk deals while aligning seller incentives.

[00:36:39] Optimizing for Outcome, Not Closing – Why long-term performance matters more than deal certainty or headline price.

[00:59:14] Craziest M&A Story – A cautionary tale about diligence failures involving a meth lab explosion.

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