In the cutthroat world of distressed debt, having a reputation as a frequent and fair "repeat player" is a key asset. Other creditors are more likely to collaborate and less likely to act opportunistically if they know they will encounter your firm again, leading to better resolutions.

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Warren Buffett's sterling reputation is a tangible asset that grants him a unique advantage. It allowed him to save Solomon Brothers from regulatory collapse and secure exclusive, highly favorable deals during the financial crisis—opportunities unavailable to anyone else, regardless of their capital.

In the long game of private equity, forgoing a short-term advantage when in a position of strength builds goodwill that will be reciprocated when you are in a weaker position. Exploiting power creates lasting mistrust that ultimately damages long-term success in a relationship-driven industry.

Dick Stack's choice to pay all creditors after his first business failure, instead of declaring bankruptcy, was the foundation of his comeback. This act of integrity built immense trust with suppliers, who then extended him credit again, proving that character demonstrated in failure is a powerful, long-term asset.

When pursuing a distressed company, understand the investors' intrinsic motivations. They often prioritize avoiding a public failure and protecting their reputation with LPs over recouping sunk capital. Frame the deal as a success story for them, not a fire sale.

Tim Ferriss's success as an angel investor was built on a reputation for discretion and trustworthiness. Founders entrusted him with confidential information, giving him access to top-tier deals. This shows that reputation is a tangible asset that can yield greater returns than direct monetization schemes.

In recurring business relationships, winning every last penny is a short-sighted victory. Intentionally allowing the other party to feel they received good value builds goodwill and a positive reputation, leading to better and more frequent opportunities in the future. It inoculates you against being price-gouged upfront.

The firm's long-term strategy, established from day one, is to compound reputation above all else. Their primary competitive moat is built on what entrepreneurs say about them compared to other VCs, a standard they apply to every interaction.

Ken Langone's negotiation principle is to let the other party feel they won more than they deserved. This isn't about getting less but about prioritizing long-term trust over maximizing a single transaction. This approach builds a reputation that attracts future opportunities and creates loyal partners.

After working out 22 distressed joint ventures during the GFC, the key lesson was that partner quality dictates outcomes more than the deal itself. When things go wrong, good partners collaborate to find solutions, while bad partners create conflict, making even a good deal untenable.

When considering debt, the most critical due diligence is not on deal terms but on the lender's character. Investigate how they have treated portfolio companies during challenging times. Partnering with a lender who will "blow you up" at the first sign of trouble is a catastrophic risk.

Being a "Repeat Player" in Distressed Debt Generates Tangible Goodwill and Better Outcomes | RiffOn