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Each company failure begins not in the press release but in a single financing decision made months or years earlier—a clause nobody argued about, a preference structure that seemed reasonable...
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Each company failure begins not in the press release but in a single financing decision made months or years earlier—a clause nobody argued about, a preference structure that seemed reasonable at the time, a covenant that looked like boilerplate. Deal Autopsy reconstructs these moments in forensic detail, following the paperwork from the conference room to the liquidation. Reported like a case file with two voices—one building the chronology, one pricing the cost—these are stories where the documents saw the ending coming first.
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12 LUG 2026 · The founder had 51% of the company's common stock. They thought they controlled the company. But the Series A, B, and C investors together held 49% of the common stock and 100% of the preferred stock, and the preferred stock had a liquidation preference, anti-dilution protection, board seat rights, information rights, acquisition approval rights, and a drag-along right. When the founder wanted to hire a new CTO, the Series C investor said no. When the founder wanted to pivot the product, the Series B investor blocked it. When the founder wanted to sell the company, the Series A investor demanded a higher price. The founder had 51% of the common stock but zero actual control. This episode reconstructs the moment the founder realized that ownership percentage and control are not the same thing, that preferred stock is more powerful than common stock, and that they'd built a company where they were the majority shareholder but the minority decision-maker. We examine what the founder could have negotiated at each round (founder-friendly board structures, supermajority requirements for major decisions, founder veto rights on certain categories of decisions), and what each would have cost in terms of investor confidence and valuation. The alternative: a structure where the founder maintained actual control through board majority, veto rights, or a dual-class share structure. The co-host delivers the final lesson: the paperwork decided who owned the company the moment it was signed, and the founder never even read it carefully enough to notice they'd lost.
28 GIU 2026 · The founder had earned 2 million shares through four years of work and vesting. They owned them outright. But the Series C term sheet included a clawback provision: if the founder left the company before a certain milestone (a successful IPO or acquisition above a certain price), the company could buy back the founder's vested shares at the original strike price. The founder didn't think it would matter—they planned to stay until the exit. But when the founder decided to leave two years later to start a new company, the clawback provision kicked in. The company exercised the clawback and bought back the founder's 2 million shares at the original $0.01 strike price, paying the founder $20,000 for shares that were now worth $40 million. The founder had lost $40 million because they'd agreed to a clawback provision they didn't understand. This episode walks through how clawback provisions work, why investors include them (they want to make sure founders are incentivized to stay), and the moment they become a weapon (when the founder wants to leave). We reconstruct the Series C negotiation, the founder's lack of concern about the clawback, the founder's decision to leave, the company's exercise of the clawback, and the legal battle that followed. The alternative: a clawback that only applied to unvested shares, or a clawback that only applied if the founder left before a certain date, or no clawback at all. The co-host names the cost: not the $40 million, but the founder's loss of agency over their own career.
14 GIU 2026 · The founder got an acquisition offer for $80 million. It was a good price, and the founder wanted to sell. But the term sheet the founder had signed years earlier required approval from investors holding a majority of the preferred stock to approve any acquisition. The Series A and Series B investors together held 60% of the preferred stock. The Series A investor wanted to sell. The Series B investor wanted to hold out for a higher price. The founder was stuck. The Series B investor had veto power over an acquisition the founder wanted to do, and the founder had never even realized it. This episode reconstructs the moment the founder discovered the acquisition approval requirement, the Series B investor's reasoning for holding out (they thought the company could be worth more in two years), the founder's frustration, and the moment the founder realized they'd built a company where they couldn't decide when to sell it. We examine what the founder could have negotiated in the Series B (a lower threshold for acquisition approval, a founder veto right, a mandatory sale at a certain price), and what each would have cost. The alternative: a structure where the founder had the right to sell the company at any price above a certain threshold without investor approval. The co-host names the real lesson: you don't own your company if you can't sell it, and most founders don't realize they've given that right away.
31 MAG 2026 · The Series A investor included a most-favored-nation clause: if any future investor got better terms than the Series A investor, the Series A investor would automatically get those better terms too. The founder thought it was fine—it was meant to protect the investor from being diluted by a cheaper later round. But when the Series B came in at a lower valuation (because growth had slowed), the most-favored-nation clause meant the Series A investor got the Series B terms retroactively. This meant the Series A investor's ownership percentage increased without them putting in any additional money. The founder's ownership percentage decreased. When the Series C came in at an even lower valuation, the Series A investor's most-favored-nation clause triggered again, and the founder was diluted again. By the time the company was worth $50 million (down from the original $40 million Series A valuation), the founder's ownership had been cut in half by most-favored-nation adjustments. This episode walks through how most-favored-nation clauses work, why they seem reasonable as investor protection, and the moment they become a problem (when later rounds are cheaper than earlier rounds). We reconstruct the Series A negotiation, the founder's lack of concern about the clause, the Series B at a lower valuation, and the moment the founder realized they'd given the Series A investor a permanent option to improve their terms. The alternative: a most-favored-nation clause with a sunset date (it expires after two years), or a clause that only applies to valuation, not to other terms. The co-host names the cost: not the dilution itself, but the founder's loss of control over the cap table in future rounds.
3 MAG 2026 · The Series A investor asked for a board observation seat—not a full board seat, just the right to attend board meetings and see what was happening. The founder agreed because it seemed like a small ask, and the investor was already getting two board seats from their firm. But what the founder didn't realize was that the observation seat gave the investor perfect visibility into every conversation, every decision, every problem before anyone else knew about it. When a competing investor came in for the Series B, they asked the Series A observer what they thought about the company's progress. The Series A observer shared everything they'd learned in the board meetings, and the Series B investor used that information to negotiate a lower valuation. The founder had accidentally given the Series A investor a spy seat. This episode reconstructs the Series A negotiation, the founder's reasoning for agreeing to the observation seat, the Series B negotiation where the information gap became expensive, and the moment the founder realized they'd created an information leak. We examine what the founder could have negotiated instead (limiting observation rights to quarterly meetings, requiring confidentiality agreements, offering a different information-sharing mechanism). The alternative: no observation seat at all, which would have meant the investor had less visibility but the founder had more privacy. The co-host names the lesson: information asymmetry is a weapon, and you don't give weapons to people you're negotiating against.
19 APR 2026 · The bridge loan came with warrants: the lender could buy shares at a strike price of $0.10 per share, and the warrants had a ten-year expiration. The founder thought it was fine—the warrants were far out of the money and would probably never be exercised. But when the Series A came in at a $40 million valuation ($2 per share), the warrants suddenly became very valuable. The lender exercised them, buying 1 million shares at $0.10 and immediately owning 2% of the company. When the Series B came in, the lender exercised again. By the time the company was preparing for an IPO, the lender had exercised warrants multiple times and owned 8% of the company—more than the founder's co-founder. This episode walks through how warrants work (they're options with a long tail), why lenders include them in bridge loans (they're a way to get upside without putting up more cash), and the moment they become a problem (when the company starts growing and the strike price becomes in-the-money). We reconstruct the bridge loan negotiation, the founder's lack of concern about the warrants, the Series A investor's question about the warrant overhang, and the moment the founder realized they'd created a permanent dilution that would compound through every future round. The alternative: a bridge loan with a lower warrant coverage ratio, or a warrant with a shorter expiration date, or no warrant at all in exchange for a higher interest rate. The co-host prices the cost: not the 8% dilution itself, but the fact that it was baked into the cap table from day one and never went away.
5 APR 2026 · The Series A investor came in with a term sheet. The founder's lawyer looked it over and said it was market. The founder signed without changing a word. The investor was surprised—they'd expected the founder to negotiate at least a few terms. The founder hadn't because they were afraid of losing the deal. What the founder didn't know was that the investor had room to move on almost every term: the valuation could have been 20% higher, the liquidation preference could have been non-participating instead of participating, the board seat could have been an observer seat instead of a full seat. The founder left $4 million on the table in valuation alone, plus structural terms that would cost them even more in the Series B and C. This episode reconstructs the moment the founder received the term sheet, the decision not to negotiate, the founder's reasoning (they didn't want to seem difficult, they didn't understand the terms well enough to negotiate, they were afraid the investor would walk away), and the moment they realized what they'd given up. We examine what the founder could have done differently (hired a better lawyer, asked for a few weeks to think about it, made one or two specific asks), and what each alternative would have cost in terms of investor confidence and deal risk. The alternative: negotiating three specific terms and accepting the rest, which would have cost the founder some negotiating capital but would have saved millions. The co-host names the real cost: not the $4 million in valuation, but the founder's belief that they had no power when they actually did.
28 DIC 2025 · The founder loaned the company $500,000 from their personal savings to bridge between the seed round and the Series A. The loan was documented as a promissory note with a 5% interest rate and a two-year maturity. The founder didn't think much about it—it was their own money, and they'd get it back when the Series A closed. But the Series A investors saw the promissory note and asked the founder to convert it to equity at the Series A valuation, which was higher than what the note's interest rate would have earned. The founder agreed, thinking they were being generous. But the Series A investors then asked for a side letter that said if the Series A didn't close, the promissory note would convert to equity at a 30% discount to the Series A price. The founder agreed to that too. The Series A fell through. The promissory note converted at the 30% discount, which meant the founder's $500,000 investment was now worth $350,000 in equity. The founder had lost $150,000 and was now significantly diluted. This episode walks through the mechanics of promissory notes, why they seem like a good bridge financing tool, and the moment they become a problem (when the next funding round introduces conversion terms). We reconstruct the founder's reasoning (they wanted to help the company, they thought the Series A would close), the Series A investor's proposal, and the moment the founder realized they'd created a liability instead of an asset. The alternative: a convertible note with a valuation cap instead of a promissory note, or no bridge at all and a slower path to the Series A. The co-host names the lesson: lending your own money to your own company is not generosity; it's a financial instrument that needs to be treated like one.
14 DIC 2025 · The founder had a four-year vesting schedule with a one-year cliff. This was standard. But when the Series B came in two years later, the new investors asked the founder to extend their vesting schedule by another two years as a sign of commitment. The founder agreed—they were excited about the Series B and wanted to show the investors they were all in. But what the founder didn't realize was that extending the vesting schedule meant that if the company was acquired or went public in the next two years, the founder would have unvested equity that would be forfeited or held in escrow. When the acquisition offer came in at year 3.5, the founder had only vested 87.5% of their shares. The acquirer insisted that the unvested shares either be forfeited or held in a one-year escrow. The founder lost $12 million in equity that they'd thought they owned. This episode reconstructs the Series B negotiation, the founder's reasoning for extending the vesting schedule, the moment they realized what they'd agreed to, and the acquisition call where the vesting schedule suddenly mattered. We examine what the founder could have negotiated instead (a one-time acceleration of vesting upon a change of control, a shorter extension period, or no extension at all). The alternative: refusing to extend the vesting schedule, which might have made the Series B investors nervous but would have protected the founder's equity. The co-host names the cost: not the $12 million in escrow, but the founder's willingness to give away something they'd already earned because they wanted to look committed.
30 NOV 2025 · The acquirer offered $100 million for the company. The founder thought they'd won. The math seemed clear: the company had raised $30 million in funding, so a $100 million exit meant $70 million in profit for the founders and employees. But the cap table told a different story. The Series A investors had a 1x non-participating liquidation preference on $10 million. The Series B investors had a 1x non-participating preference on $15 million. The Series C investors had a 1x participating preference on $5 million. After all the preferences were paid, there was $70 million left, but the Series C investors' participation clause meant they got their $5 million back, then split 20% of the remaining $65 million with the founders and employees. The founder ended up with $24 million instead of the $40 million they thought they'd get. This episode walks through the exact waterfall calculation, the moment the founder realized they'd never actually understood how the cap table would be paid out, and the acquirer's silence when the founder asked if $100 million was a good price. We reconstruct the board meeting where the acquisition was discussed, the Series C investor's explanation of the waterfall, and the founder's realization that they'd been building someone else's company. The alternative: a cap table structure with simpler preferences and no participation clause, which would have meant a lower valuation in the Series C but a clearer exit math. The co-host prices the real cost: not the $16 million the founder lost, but the year of building the company thinking they owned more than they actually did.
Each company failure begins not in the press release but in a single financing decision made months or years earlier—a clause nobody argued about, a preference structure that seemed reasonable...
mostra di più
Each company failure begins not in the press release but in a single financing decision made months or years earlier—a clause nobody argued about, a preference structure that seemed reasonable at the time, a covenant that looked like boilerplate. Deal Autopsy reconstructs these moments in forensic detail, following the paperwork from the conference room to the liquidation. Reported like a case file with two voices—one building the chronology, one pricing the cost—these are stories where the documents saw the ending coming first.
mostra meno
Informazioni
| Autore | 3Peaks |
| Organizzazione | 3Peaks |
| Categorie | Economia , Storia |
| Sito | www.spreaker.com |
| ops@3peakspodcasts.com |
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