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:
_____________________
💡Running M&A with a lean team? DealRoom helps you do more with less. Manage your pipeline, coordinate diligence, track deliverables, and keep stakeholders aligned- all in one place.
👉See it in action by requesting a demo:https://hubs.ly/Q03ZMvQX0
____________________
[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.
____________________
Questions, comments, concerns?
Follow Kison Patel for behind-the-scenes insights on modern M&A.
Christian Hassold, Senior Vice President of Corporate Development and Strategic Partnerships at Wpromote x Giant Spoon
Christian has been on both sides of M&A as a serial founder and corporate development leader. In this episode, Christian shares his hard-earned lessons about culture as the ultimate deal-breaker in M&A. He breaks down the subtle red flags that founders miss when evaluating acquisition targets, explains why he interviews employees before talking to investors, and shares the fascinating story of acquiring a competitor that was shutting down—where culture assessment made all the difference. Christian also introduces his 5-pillar lean M&A framework and explains why "commit to close" doesn't mean ignoring red flags, but rather cataloging them until you have enough evidence that culture fit is fundamentally broken.
Things You'll Learn
_____________
💡Stop juggling six different tools to run one deal. DealRoom brings pipeline management, diligence tracking, document sharing, and team collaboration into one platform. Purpose-built for M&A teams who need to move fast without losing control.
👉Request your demo today:https://hubs.ly/Q03ZMvQX0
_____________
[00:03:00] The Entrepreneur's Path to Corporate Development – How building and selling three companies shaped Christian's view on culture fit
[00:10:30] Three Things I Wish I Knew Before My First Deal – Why assuming nothing about culture and motivations is critical [00:13:00] The Lean M&A Framework for Culture Assessment – Five pillars that put people and culture at the center of deal evaluation
[00:16:00] Deep Dive the Business: Beyond Numbers – Why talking to customers and employees reveals culture gaps before they kill deals
[00:22:30] Commit to Close vs. Catalog Red Flags – When dishonesty, fraud, or culture misalignment should stop a deal immediately
[00:27:00] Culture as the Ultimate Deal-Breaker – The difference between management style preferences and irreconcilable cultural dysfunction
[00:31:00] Post-Merger Integration Starts Day One – Why the PMI team needs a front-row seat on culture assessment from the IOI forward
[00:54:30] The Hub Logics Story: Interviewing Employees First – How Christian uncovered the real reasons a competitor failed by talking to the team
[01:12:18] The Craziest M&A Story – AI-driven M&A is redefining tech valuations—exits are now priced at multiples of capital raised rather than traditional ARR or EBITDA.
Questions, comments, concerns?
Follow Kison Patel for behind-the-scenes insights on modern M&A.
Donara Jaghinyan, returns for Part 2 of our conversation on what actually breaks integrations after the deal closes. This episode tackles the messy reality of post-merger execution: integration debt that piles up when long-tail items don't get done, change management as a practical framework (not corporate fluff), and the cultural friction that surfaces in cross-border deals. Donara shares firsthand experiences navigating gender-based hierarchy in Middle Eastern TSA negotiations, building trust across geographies, and managing the communication breakdowns that create employee uncertainty. If you missed Part 1, listen to that first—then come back for the operational realities that determine whether your deal actually delivers value.
Things You'll Learn
_____________
💡 Today's Episode is Sponsored by DealRoom
The best M&A teams close deals faster...not because they work harder, but because they have better systems. DealRoom helps you manage your entire deal lifecycle from target identification through close. No more hunting for documents or wondering what's blocking progress.
👉Request a Demo today: https://hubs.ly/Q03ZMvQX0
__________________
[00:02:00] What Is Integration Debt and Why Track It – Long-tail items that don't close in 90 days and how to prevent them from getting lost after handoff
[00:04:00] Change Management: Framework, Not Fluff – How change management sits on top of integration like Agile and why it's about experience, not just execution
[00:06:00] Culture Isn't a Scapegoat—It's Strategy – Three approaches to culture in M&A: old-school "figure it out," progressive tailoring, and proactive culture transformation
[00:11:00] Implementing Change Management from Scratch – Surveys, assessments, and identifying change agents who can influence adoption before mass rollout
[00:17:30] US Work Standards Don't Translate Globally – Why European lunch breaks and Middle Eastern approval hierarchies require adaptation, not enforcement
[00:19:00] Gender and Hierarchy in Cross-Border TSAs – Donara's experience navigating decision-making challenges as a woman in Middle Eastern TSA negotiations
[00:21:00] Building Trust Across Borders – Human connections that smooth working relationships and create execution momentum
[00:24:00] Where Friction Actually Shows Up – Communication gaps, leadership changes, and employee uncertainty that derail integration plans
[00:27:00] What Goes Wrong and How to Go Fast – Delays, plan shifts, leadership turnover, and why IMOs push back on unrealistic timelines
[00:30:00] The Craziest Things in M&A – From TSAs resolved by title hierarchy to founders walking away from earn-outs mid-integration.
Questions, comments, concerns?
Follow Kison Patel for behind-the-scenes insights on modern M&A.
Donara joins us to pull back the curtain on why integrations break—and what it actually takes to make them work. With deep experience across healthcare, SaaS, professional services, and financial services in both public and PE-backed environments, Donara has led diligence, post-close integration, TSA execution, and enterprise system implementations. This episode tackles the hard truths about carve-outs, TSA management, day-one readiness, and the cross-functional dependencies that most teams miss until it's too late. If you've ever wondered why integration timelines slip or costs balloon, this conversation delivers the answers.
Things you will learn:
Why TSAs aren't contracts, they're projects with hard deadlines, cost escalations, and integration dependencies that functional teams consistently underestimate
The hidden complexity of carve-outs and how scope, vendor negotiations, and people gaps create surprises even with solid diligence
How Integration Management Offices (IMOs) orchestrate cross-functional dependencies that functional leads can't see
_____________
💡 Tired of spending weeks organizing seller documents and building diligence checklists from scratch?
DealRoom helps M&A teams cut manual review time and move faster through diligence. Automatically organize messy data rooms, surface risks earlier, and generate tailored diligence requests in seconds—so your team can focus on analysis, not admin work.
👉 See how AI can streamline your next deal: dealroom.net/ai
__________________
Episode Timestamps
[00:02:30] From International Relations to M&A Integration – Donara's unconventional path from Armenia to becoming a full-time integration leader in Boston
[00:04:00] The Dependency Problem No One Sees Coming – Why integration isn't just about systems or people—it's about understanding what breaks when you miss upstream and downstream connections
[00:06:00] Why You Can't Just Promote a PM to IMO – The critical difference between project management and integration program leadership
[00:07:00] What Gets Underestimated in Carve-Outs – Scope creep, vendor negotiations, and people gaps that blindside even experienced teams
[00:09:00] TSAs Are Projects, Not Contracts – Why treating TSAs as temporary extensions instead of hard deadlines creates integration debt and cost overruns
[00:13:00] Managing Two Carve-Outs Simultaneously – The story of integrating two business units with heavy TSAs, cross-border complexity, and mismatched organizational structures
[00:19:00] Getting IMO Involved Before LOI – How early integration involvement during diligence creates smoother execution and realistic timelines
[00:30:00] Day One Readiness and the 30/60/90 Framework – What actually happens from day one through the first 90 days, including controls, discovery, and execution milestones
[00:37:00] Integration Governance That Actually Works – Structuring steering committees, functional cadences, and escalation paths that keep deals on track
[00:40:00] The Integration Kickoff That Sets the Tone – What to cover, who to involve, and how to align teams on why the deal matters
Questions, comments, concerns?
Follow Kison Patel for behind-the-scenes insights on modern M&A.