Episodes
The Earnout Milestone Definition That Cost a Seller 25 Million
In this episode of The Acquisition Talk, Lucas and Luna dissect a real-world earnout failure: a seller who left 25 million dollars on the table because the earnout milestone was defined in a single ambiguous sentence. They walk through the exact language that caused the dispute, why the buyer's interpretation won in arbitration, and the four questions every seller should ask before signing an earnout. You'll hear how a milestone like 'successful commercial launch' can be twisted, why the…
The Exclusivity Fee Trap That Cost a Seller 40 Million
In episode 164 of The Acquisition Talk, hosts Lucas and Luna dissect a little-known but devastating M&A pitfall: the exclusivity fee trap. When a seller signs a 60-day exclusivity agreement with a prospective buyer, they often unknowingly agree to pay a hefty breakup fee if the deal collapses—even over the buyer's own financing failure. Through a real-world case where a seller lost $40 million, Lucas and Luna explain how exclusivity fees are negotiated, when they trigger, and why sellers must…
The Anti-Assignment Trap That Cost a Seller 16 Million
In episode 163 of The Acquisition Talk, Lucas and Luna dissect a deal that hinged on consent-to-assignment language buried in a B2B SaaS contract. A software company with a $60 million revenue run rate was sold, but the buyer discovered that the target's largest client had a change-of-control clause requiring written consent before the deal could close. The seller assumed it was a formality; the client's procurement team used the moment to renegotiate, slashing contract value and delaying the…
The Escrow Trap That Cost a Seller 19 Million
In this episode of The Acquisition Talk, Lucas and Luna dig into a deal that fell apart over something most operators barely think about: the escrow holdback. A seller of a niche industrial services company agreed to a 10 percent escrow, standard stuff, but the escrow agreement was drafted with a post-closing indemnity claim that dragged on for thirty months. The result? The seller never saw nineteen million dollars of the purchase price, and the money sat in a custodial account earning next to…
The Post-Closing Adjustment That Cost a Seller 35 Million
In this episode of The Acquisition Talk, Lucas and Luna dissect a real-world acquisition gone wrong: a $200 million deal where the seller walked away with $35 million less than expected due to a post-closing working capital adjustment. They explore how a vague definition of 'normal course' in the working capital peg, combined with an aggressive buyer interpretation, triggered a massive dispute. The hosts break down the exact language that caused the problem, explain the concept of 'working…
The Interest Rate Adjustment Clause That Cost a Seller 30 Million
In this episode, Lucas and Luna dissect a specific M&A pitfall that cost a seller $30 million: the interest rate adjustment clause buried in a purchase agreement. They walk through the real-world case of a Midwest manufacturing firm sold in early 2025, where a seemingly standard provision—tied to a floating interest rate—turned against the seller when the Federal Reserve's rate path shifted unexpectedly. They explain how the clause worked, why both sides agreed to it, and how the seller's own…
The Purchase Price Allocation Trap That Cost a Buyer 20 Million
In this episode of The Acquisition Talk with Fexingo, Lucas and Luna dissect a deal that went wrong not during due diligence, but after closing — when the buyer discovered that the purchase price allocation had shifted value away from the assets that mattered most. Through a real-world case of a $120 million acquisition of a niche industrial software company, they explore how a seemingly routine allocation of the purchase price to tangible assets, customer relationships, and goodwill triggered…
The Working Capital Definition Trap That Cost a Seller 28 Million
In this episode of The Acquisition Talk, Lucas and Luna dissect a recent mid-market deal that fell apart over a single disputed line in the working capital definition. A seller lost $28 million when the buyer recalculated 'normal course' to exclude a seasonal inventory build. They break down the two common definitions—'same accounting principles' versus the more precise 'identical accounting principles'—and explain why the phrase 'in the ordinary course' can be a ticking time bomb. Using the…
The Working Capital False Peg That Cost a Seller 30 Million
In Episode 157 of The Acquisition Talk, Lucas and Luna dissect a deal where a standard working capital peg turned into a $30 million dispute. They walk through how a seller's seasonal inventory bloat, a vague definition of 'normal course', and a missed true-up adjustment triggered a post-closing clawback that erased most of the earnout. Using a real-world manufacturing case from early 2026, they explain the math behind the peg, the trap of historical averages, and the negotiation tactics that…
The Reps and Warranties Trap That Cost a Buyer 30 Million
In this episode of The Acquisition Talk, Lucas and Luna dissect a specific, costly M&A mistake: a buyer who skipped the reps and warranties insurance route and paid $30 million when a seller's representation about a key patent was false. The deal was a $200 million acquisition of a medical-device firm. The seller's reps said all patents were valid. Post-close, a competitor successfully challenged the patent, wiping out the product line's value. The buyer had no recourse because the…
The Earnout Adjustment Trap That Cost a Seller 55 Million
In this episode of The Acquisition Talk, Lucas and Luna dissect a $55 million earnout dispute that turned a celebrated deal into a cautionary tale. They explore how a post-closing EBITDA adjustment clause—meant to protect the buyer from a downturn—ended up punishing the seller for the very synergies the buyer had promised. Through the lens of a mid-market industrial software company sold in 2022, they walk through the drafting errors, the accounting fights over addbacks, and the legal gray zone…
The Earnout Trap That Cost a Seller 40 Million
In this episode of The Acquisition Talk, Lucas and Luna dissect a $400 million deal where a seller's earnout clause backfired, costing them $40 million. They explore the pitfalls of earnout structures, the importance of defining performance metrics, and the role of control in achieving earnout targets. With real-world examples and lessons for both buyers and sellers, they explain why earnouts can be a double-edged sword. Tune in to learn how to structure earnouts that protect your interests and…
The Materiality Scrape Trap That Scuttled a 60 Million Deal
In this episode of The Acquisition Talk, we dissect a deal that fell apart over a single overlooked clause: the materiality scrape. When a private equity firm agreed to buy a niche manufacturing company for $60 million, they thought they had negotiated a standard bring-down condition. But the seller's counsel slipped in a 'materiality scrape' that erased the protection at closing. The result? The buyer discovered a $9 million customer loss two days after signing, but couldn't walk away or…
The Working Capital Peg Trap That Cost a Seller 22 Million
In this episode of The Acquisition Talk, Lucas and Luna dissect an M&A deal where a working capital peg clause quietly shifted $22 million out of a seller's pocket. Through the story of a mid-market industrial distributor, they show how the peg—often a single line in the purchase agreement—can become a weapon when inventory is misvalued or the target's cash conversion cycle shifts. They explain the mechanics of net working capital, the role of the closing statement, and why sellers need to…
The M&A Deal Structure Trap That Cost a Seller 18 Million
In this episode of The Acquisition Talk, Lucas and Luna dissect a seller's $18 million mistake: choosing a stock deal over an asset sale without understanding the tax consequences. Through the story of a manufacturing company founder who sold to a strategic buyer in mid-2026, they walk through the difference between Section 338(h)(10) elections and direct asset purchases, the impact of capital gains versus ordinary income rates, and why the structure you choose can cost you millions. They break…
The Data Room Leak That Sank a $75 Million Deal
In episode 150 of The Acquisition Talk, Lucas and Luna unpack a fresh M&A horror story: a seller's data room leak that torpedoed a $75 million acquisition just days before signing. They trace how a poorly secured virtual data room exposed confidential customer contracts and pricing models to a competitor, triggering a material adverse change clause and a walk-away. The episode drills into the practical safeguards every operator should have in place—from access logs to NDAs for every viewer—and…
The EBITDA Addback Trap That Cost a Seller 11 Million
In this episode, Lucas and Luna dissect a specific seller-side M&A failure: an $11 million loss caused by an over-aggressive EBITDA addback. They walk through a real-world deal where a manufacturing company's owner justified aggressive addbacks for owner perks and one-time costs, only to have the buyer's quality-of-earnings audit unravel them days before closing. The hosts explain how addbacks are negotiated, why they can trigger working capital adjustments and earnout clawbacks, and the…
The MAC Clause That Cost a Buyer 45 Million
When the deal is signed but not yet closed, a material adverse change clause can mean everything. In this episode, Lucas and Luna dissect a 2024 acquisition where a buyer invoked the MAC clause to back out of a $300 million deal — and paid a $45 million reverse termination fee after a court ruled the change didn't qualify. You'll learn what counts as a MAC, why courts view them with skepticism, and how to draft a clause that actually protects you without scaring off the seller. With real…
How an Anti-Sandbagging Clause Cost a Buyer $30 Million
Episode 147 of The Acquisition Talk dives into one of the most misunderstood provisions in M&A purchase agreements: the anti-sandbagging clause. Most sellers assume that if they hide a problem, the buyer can sue after closing. But an anti-sandbagging clause flips that logic—it says the buyer cannot bring a claim for breaches they knew about or reasonably should have discovered before signing. Lucas and Luna walk through the case of OmniCorp's $150 million acquisition of DataStream Analytics.…
The IP Chain-of-Title Trap That Cost a Buyer 40 Million
In this episode of The Acquisition Talk, Lucas and Luna examine a costly M&A mistake: failing to verify intellectual property ownership before closing. They walk through a real-world case where a buyer lost $40 million because a critical patent wasn't properly assigned from an inventor to the target company. Discover why IP due diligence goes beyond checking patent filings, how 'chain of title' gaps arise, and what operators can do to avoid this expensive trap. Perfect for business owners…
The Material Adverse Change Trap That Cost a Buyer 45 Million
M&A contracts often include a Material Adverse Change (MAC) clause, allowing buyers to walk away if something fundamentally harms the target. But these clauses are notoriously hard to invoke. In this episode, we dissect a case where a buyer tried to invoke a MAC after a raw material price spike caused a 30% earnings drop at a specialty chemicals company. The seller fought back, a court ruled the downturn was industry-wide and foreseeable, and the buyer lost $45 million in legal fees and…
The M&A Financing Condition Trap That Cost a Seller 25 Million
In this episode of The Acquisition Talk, hosts Lucas and Luna dissect a six-figure M&A mistake: a seller who lost $25 million after a buyer invoked a loosely worded financing condition when interest rates rose. The seller had turned down a competing all-cash offer because the winning buyer promised a faster close. But the purchase agreement's financing condition allowed the buyer to walk without penalty when debt markets tightened—even though the buyer had ample equity to close. Lucas explains…
The Indemnification Basket Trap That Cost a Seller 12 Million
In M&A, the indemnification basket is often a routine clause—until it isn't. This episode unpacks the difference between a 'deductible' basket and a 'tipping' basket, and how one software company seller lost $12 million because they assumed a $500,000 threshold worked like an excess policy. Lucas and Luna walk through the exact contract language that hooked a family office, the negotiation that should have happened, and the painful lesson about reading baskets on a net-loss basis. If you're…
The Environmental Liability Trap That Cost a Seller 15 Million
In M&A, environmental liabilities can lurk beneath the surface. This episode of The Acquisition Talk with Fexingo examines a case where a seller of a Midwestern bottling plant faced a $15 million indemnity claim after the buyer discovered decades-old soil contamination. Lucas and Luna walk through how the contamination was missed during due diligence, the indemnity clause that triggered the loss, and the operational lessons for sellers who think they have clean property. They also discuss when…
The Non-Compete Trap That Cost a Buyer 25 Million
In this episode, Lucas and Luna dissect a $25 million M&A disaster caused by a poorly drafted non-compete clause. When OmniCorp acquired software firm DataSync, they relied on a standard non-compete from the seller's CEO. But a single loophole—defining 'competitive business' too narrowly—allowed that CEO to launch a nearly identical company just six months later, poaching key clients and employees. The result: OmniCorp's projected synergies evaporated, and a lawsuit consumed millions more.…
The Customer Concentration Trap in M&A That Cost $40 Million
When a private equity firm acquired a SaaS company for $200 million, they assumed a 70% revenue concentration was a strength—until the customer renegotiated, costing them $40 million. This episode of The Acquisition Talk with Fexingo explores how buyers can identify, price, and protect against customer concentration risk in M&A deals. Lucas and Luna discuss specific deal structures including revenue covenants, earnouts tied to key customer retention, and adjusted valuation multiples. They also…
The Management Retention Trap That Cost a Buyer $50 Million
In 2024, a private equity firm acquired a fast-growing SaaS company for $300 million. The founder and CEO was critical to client relationships and product vision. The buyer included a generous retention package with a $2 million signing bonus and a guaranteed three-year earnout that paid out regardless of performance. But the CEO left after 18 months, collecting the remaining earnout as a 'good leaver'. A weak non-compete allowed him to consult for a competitor, and the buyer lost its largest…
The M&A HSR Wait That Cost a Buyer 60 Million
Episode 138 of The Acquisition Talk examines a common but deadly M&A pitfall: the HSR second request. Lucas and Luna walk through the story of a private equity firm that agreed to buy a specialty chemicals company for $400 million, only to see the FTC drag the deal through a nine-month antitrust review. The delay triggered financing cost escalations, market shifts, and management distraction that collectively erased $60 million in deal value. The hosts break down what went wrong—the assumptions…
The Seller Financing Subordination Trap That Cost a Buyer $35 Million
In this episode of The Acquisition Talk, Lucas and Luna dissect a common but dangerous M&A pitfall: the seller financing subordination trap. Using the real-world example of Pacific Rim Coatings—a $120 million acquisition in 2022 that included a $30 million seller note—they explain how a seemingly harmless subordination clause allowed the seller to convert their note into majority equity when the buyer’s EBITDA dipped. The result: the buyer lost $35 million in legal fees, write-downs, and…
The M&A Cultural Integration Trap That Cost a Buyer $20 Million
When a precision engineering firm bought a robotics startup for $150 million, they nailed the financial due diligence but ignored culture. Within 18 months, key engineers quit and revenue dropped 40 percent. Lucas and Luna dissect how imposing rigid processes destroyed the startup's innovation engine, why earnout structures can't fix culture clashes, and what the buyer should have done differently. A focused look at the human side of deal value destruction. #MergersAndAcquisitions…
The M&A Non-Solicit Trap That Cost a Buyer $30 Million
Lucas and Luna unpack a little-known deal-killer in M&A: the non-solicitation clause. When a mid-market tech buyer acquired a SaaS company for $120 million, they assumed the non-solicit would let them keep the target's key employees. What they missed was a two-way restriction that prevented them from even approaching their own team. The seller used that loophole to poach four top engineers within six months, landing the acquirer in a talent war that cost $30 million in lost revenue and legal…
The M&A Tax Indemnity Trap That Cost a Seller $9 Million
Episode 134 of The Acquisition Talk with Fexingo dissects a bitterly learned $9 million lesson in tax indemnification. Lucas and Luna walk through the case of a mid-market manufacturing seller who agreed to a standard-looking tax indemnity clause—only to discover after closing that the buyer used a built-in tax attribute to claim a refund for pre-closing losses, then demanded the seller reimburse the full amount under the indemnity. The hosts explain why the standard 'taxes and tax returns'…
The Earnout Trap That Cost a Seller $14 Million
Episode 133 of The Acquisition Talk with Fexingo. Lucas and Luna break down the earnout trap that cost a seller $14 million after a private equity buyer gamed the post-closing performance metrics. They walk through the specific contract language — the definition of EBITDA, the treatment of bad debt, the allocation of overhead — that turned a promised $20 million earnout into a $6 million payout. Listeners learn why earnouts are riskier than they look, how to spot the three clauses that almost…
The M&A Exclusivity Trap That Cost a Buyer $50 Million
Episode 132 of The Acquisition Talk dives into the no-shop clause — a standard fixture in M&A exclusivity agreements that nearly cost a serial acquirer $50 million. Lucas and Luna break down a real 2023 deal where a buyer signed a 90-day exclusivity period without a fiduciary-out provision, only to have the target's key customer sue mid-exclusivity, cratering the valuation. They explain how the buyer got trapped into closing on unfavorable terms because the no-shop prevented them from walking…
The M&A Working Capital Peg That Cost a Seller $6 Million
In this episode, Lucas and Luna dissect a surprisingly expensive M&A artifact: the working capital peg. Using the real-world case of a mid-market industrial distributor that sold for $120 million, they walk through how a $2 million miscalculation in the working capital target — triggered by a seasonal spike in receivables — cost the seller $6 million at closing. They explain what the working capital peg is, how buyers and sellers negotiate it, and why a poorly timed closing date can shift…
The M&A Post-Closing Audit Trap That Cost a Buyer $10 Million
In this episode of The Acquisition Talk, Lucas and Luna unpack a little-known pitfall in M&A: the post-closing audit trap. They walk through the real-world case of a mid-market buyer who acquired a manufacturing company for $80 million, only to discover $10 million in hidden liabilities buried in the target's pre-closing financials — after the purchase price was locked. The hosts explain how the buyer's failure to secure audit rights in the purchase agreement left them without recourse, turning…
The M&A Data Room Trap That Sank a $30 Million Deal
In Episode 129 of The Acquisition Talk, Lucas and Luna dissect a $30 million acquisition that collapsed because the seller's data room was a mess. They walk through how incomplete financials, missing contracts, and unorganized files triggered a buyer's diligence fatigue and a material adverse change clause. The episode drills into the specific red flags that killed the deal: stale inventory schedules, uncapped indemnification exposure, and a seller who treated the data room as an afterthought.…
The M&A Termination Fee Trap That Cost a Buyer $22 Million
Lucas and Luna dissect a real-world M&A disaster where a buyer ignored the termination fee clause in a letter of intent and lost $22 million when a competitor swooped in with a higher bid. They explain how termination fees (also called break fees) work, why they're not just boilerplate, and the one procedural misstep that cost a private equity firm millions. The episode walks through the specific timeline: the LOI that triggered the fee, the flawed no-shop clause, and the lawsuit that followed.…
The M&A Purchase Price Adjustment Trap That Cost a Seller $8 Million
In this episode of The Acquisition Talk with Fexingo, hosts Lucas and Luna dissect a purchase price adjustment trap that cost a medical device company's founder $8 million after closing. They walk through the mechanics of a 'locked-box' mechanism versus a traditional completion accounts adjustment, and explain how a single clause buried in the working capital definition allowed the buyer to reclassify $8 million in inventory as excess working capital post-closing. The discussion covers how the…
The M&A Working Capital True Up That Cost a Seller $3 Million
In this episode of The Acquisition Talk, Lucas and Luna dissect a common but costly M&A trap: the working capital true-up. They walk through a real-world case where a seller lost $3 million because they misunderstood how the target working capital peg was calculated. The hosts explain why sellers often assume they'll get paid for every dollar of receivables, only to discover that post-close adjustments capture only the change from a negotiated baseline. They cover the difference between a fixed…
The Escrow Trap That Cost a Seller 40 Percent of Their Payout
When you sell a business, the standard escrow holdback seems like a routine safeguard — 10 percent of the purchase price held for 18 months. But in this episode, Lucas and Luna unpack a case where a seller agreed to a 25 percent escrow tied to future revenue targets, losing 40 percent of their payout after the buyer changed the forecast methodology. We walk through the specific contract language that created the trap — a vague definition of 'earnings before interest, taxes, depreciation, and…
The M&A Reps and Warranties Insurance Trap That Cost a Buyer $18 Million
Episode 124 of The Acquisition Talk examines the hidden risks of reps and warranties insurance in M&A. Lucas and Luna dissect a real-world case where a buyer relied on a $10 million R&W policy to cover post-close liabilities—only to discover the policy's 'known breach' exclusion voided coverage for an $18 million tax liability hidden in the target's old subsidiary. They walk through the specific policy language that tripped up the buyer, including the difference between 'knowledge' definitions…
The M&A Material Adverse Change Trap That Killed a $200 Million Deal
Lucas and Luna dissect a 2025 Delaware Chancery Court ruling where a buyer walked away from a $200 million acquisition after a target company lost its largest customer post-signing. The seller sued, arguing the loss was temporary and not a Material Adverse Change. The court sided with the buyer, setting a precedent on what counts as 'material' in MAC clauses. Lucas explains the five key factors judges weigh, Luna questions how sellers can protect themselves. The episode closes with a thoughtful…
The M&A Break Fee Trap That Cost a Buyer $45 Million
When the $400 million acquisition of a cloud infrastructure company collapsed due to a surprise regulatory filing, the buyer assumed they'd get their due diligence costs back. They didn't read the break fee clause closely enough. In this episode, Lucas and Luna break down the case of ZephyrTech — a mid-market buyer that agreed to a 1.5 percent reverse break fee in a letter of intent, only to discover the fee only triggered if the target breached a material adverse condition. The target simply…
The M&A Covenant Trap That Cost a Buyer $25 Million
In this episode of The Acquisition Talk, Lucas and Luna dive into one of the most overlooked deal-killers in M&A: the negative covenant trap. They walk through the real story of a private equity firm that bought a specialty chemical company for $150 million, only to discover that a seemingly standard 'no additional debt' covenant in the target's existing credit agreement blocked the acquisition financing itself. The PE firm had to pay $25 million to waive the covenant—money that went straight…
The M&A Stock-for-Stock Trap That Cost a Seller 80 Percent
Episode 120 of The Acquisition Talk dives into a specific M&A risk that sellers often overlook: stock-for-stock deals where the buyer's shares collapse post-close. Lucas and Luna examine a real case from 2024 where a private company founder accepted shares in a publicly traded acquirer, only to see those shares drop by 80 percent within a year due to undisclosed revenue concentration. The episode breaks down the structural mechanics — how a fixed exchange ratio, a collar provision, and a…
The M&A Non-Compete That Cost a Buyer $12 Million in Lost Revenue
Episode 119 of The Acquisition Talk examines a lesser-known trap in M&A: the non-compete agreement that was too narrow. Lucas and Luna break down a real-world case where a private equity firm bought a regional HVAC distributor for $45 million, only to discover that the seller's non-compete allowed him to open a competing business in an adjacent territory within six months. The result: $12 million in lost revenue and a legal battle that lasted two years. The hosts explain how the non-compete's…
The M&A Indemnification Survival Trap That Wiped Out a $40 Million Deal
In this episode of The Acquisition Talk, Lucas and Luna dive into one of the most overlooked pitfalls in M&A: the indemnification survival period trap. They dissect a real-world case where a $40 million deal collapsed because the buyer failed to negotiate a longer survival window for a critical warranty breach. The hosts explain how standard boilerplate terms—typically 12 to 18 months for general indemnities—can leave buyers exposed when latent defects surface later. They walk through the…
The M&A Retention Bonus That Backfired on a Private Equity Firm
Episode 117 of The Acquisition Talk examines a real-world case from early 2026 where a mid-market private equity firm structured a retention bonus to keep key management post-close — only to see the CFO leave three months early, triggering a clawback that cost the PE firm $1.8 million in litigation and lost tax benefits. Lucas and Luna walk through the specific contract language — the 'good leaver' definition, the accelerated vesting trap, and the unintended incentive to depart — and explain…
The Management Roll-Up Trap in M&A That Cost a CEO His Company
In Episode 116 of The Acquisition Talk, Lucas and Luna examine one of M&A's most underappreciated failure modes: the management roll-up trap. They walk through the cautionary tale of a $5 million EBITDA industrial services firm whose CEO was lured into a roll-up by a financial sponsor. The CEO kept 15% equity and an earnout, but within 14 months the sponsor had replaced him, triggered the earnout clawback, and used the equity structure to force a dilutive recap. The hosts break down the…
Showing the latest 50 episodes. The full archive of 165 is on Apple Podcasts, Spotify and every major podcast app — or via the RSS feed above.