In the current late-cycle, frothy environment, maintaining investment discipline is paramount. Oaktree, guided by Howard Marks' philosophy, is intentionally cautious and passing on the majority of deals presented. This discipline is crucial for avoiding the "worst deals done in the best of times" and preserving capital for future dislocations.

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VCs are willing to "hold their nose" and pay extremely high multiples for one or two exceptional companies they feel are essential to win. However, unlike in 2021, they are not applying this undisciplined, high-valuation strategy to their entire portfolio, demonstrating a more disciplined approach to portfolio construction.

Successful concentration isn't just about doubling down on winners. It's equally about avoiding the dispersion of capital and attention. This means resisting the industry bias to automatically do a pro-rata investment in a company just because another VC offered a higher valuation.

Don't chase every deal. Like a spearfisherman, anchor in a strategic area and wait patiently for the 'big fish'—a once-in-a-decade opportunity—then act decisively. This requires years of preparation and the discipline to let smaller opportunities pass by, focusing only on transformative deals.

To avoid confirmation bias and make disciplined capital allocation decisions, investors should treat every follow-on opportunity in a portfolio company as if it were a brand-new deal. This involves a full 're-underwriting' process, assessing the current state and future potential without prejudice from past involvement.

Bessemer Venture Partners publicly lists massive companies it passed on to foster a learning culture. This highlights their philosophy that the opportunity cost of missing a transformative company (a crime of omission) is far more damaging than investing in one that fails (a crime of commission).

Inspired by Charlie Munger, this investment strategy is built on three common-sense pillars: maximizing earnings growth, maintaining valuation discipline, and focusing on downside risk. The goal is reliability and avoiding major mistakes rather than chasing spectacular, high-risk wins.

A crucial, yet unquantifiable, component of alpha is avoiding catastrophic losses. Jeff Aronson points to spending years analyzing companies his firm ultimately passed on. While this discipline doesn't appear as a positive return on a performance sheet, the act of rigorously saying "no" is a real, though invisible, driver of long-term success.

Instead of trying to have a view on everything, Herb Wagner's team embraces not knowing. They actively avoid complex situations, like Chinese property developers, where risks are opaque and dependent on government action. This discipline of knowing what you don't know is central to their strategy.

Adhering to strict, dogmatic rules—such as fixed ownership targets or avoiding certain stages—is a primary cause of missing outlier investments. The podcast highlights passing on Cruise due to ownership concerns as a key example. True discipline requires adapting to market changes, not blindly following old rules.

Contrary to the common VC advice to "play the game on the field" during hot markets, Founder Collective reduces its check size for high-valuation deals. This strategy allows them to maintain exposure to promising companies while intentionally keeping the fund's overall weighted average cost basis low.

Oaktree’s Late-Cycle Discipline Means Passing on More Deals Than It Invests In | RiffOn