Auto parts company FBG funded its acquisition spree with a sophisticated fraud using "invoice factoring," a corporate version of a payday loan. By selling the same tranche of invoices to multiple private creditors, it illegitimately raised funds, leading to a collapse with $2.3 billion unaccounted for.
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Official financial segments often reflect bureaucracy, not true business economics. By creating a 'Shadow P&L' through deductive analysis, investors can uncover massive hidden costs in non-core initiatives, as ValueAct did with Microsoft's hardware divisions.
Sonder's bankruptcy wasn't due to its core idea of a standardized home rental, which was sound. The failure stemmed from raising too much venture capital ($680M), which created immense pressure for hyper-growth. This forced the company to sign unprofitable leases, proving a good business can be destroyed by the wrong funding model and unrealistic expectations.
Gwen Whiting bootstrapped her company with $250k in credit card debt. She found card APRs were more favorable than the high-interest small business loans marketed to women at the time, making strategic debt rollover a viable, albeit risky, funding path.
The dramatic rise in BNPL usage across all demographics, including 41% of young shoppers, is a negative forward-looking indicator. While framed as innovation, it's a form of modern usury that reveals consumers cannot afford their purchases, creating a significant, under-discussed credit risk for the economy.
The massive OpenAI-Oracle compute deal illustrates a novel form of financial engineering. The deal inflates Oracle's stock, enriching its chairman, who can then reinvest in OpenAI's next funding round. This creates a self-reinforcing loop that essentially manufactures capital to fund the immense infrastructure required for AGI development.
A guest funded his gambling by treating loan applications like a sales negotiation. He would purposely request a higher amount than needed (e.g., $10,000), anticipating the underwriter would reject it but counteroffer with a smaller, more achievable amount (e.g., $7,500), which was his actual goal.
Beyond outright fraud, startups often misrepresent financial health in subtle ways. Common examples include classifying trial revenue as ARR or recognizing contracts that have "out for convenience" clauses. These gray-area distinctions can drastically inflate a company's perceived stability and mislead investors.
To overcome cash flow issues for large purchases, small businesses can offer a 'Special Purpose Vehicle' (SPV) to loyal customers. A customer fronts the capital, gets repaid first from the sales, and then splits the remaining profit with the business, turning patrons into financial partners.
Jeff Aronson reframes "distressed-for-control" as a private equity strategy, not a credit one. While a traditional LBO uses leverage to acquire a company, a distressed-for-control transaction achieves the same end—ownership—by deleveraging the company through a debt-to-equity conversion. The mechanism differs, but the outcome is identical.
The founder of Frank was sentenced to prison not for selling a useless FAFSA-help service to students, but for fraudulently selling a list of 4.25 million student email addresses—most of which were fake—to J.P. Morgan. This highlights how defrauding a major financial institution carries more severe consequences than exploiting vulnerable consumers.