High-profile CEOs from large corporations frequently struggle as LBO operating partners. They are accustomed to vast resources and being the sole boss, a mentality that clashes with the mentorship and resource-constrained environment of smaller portfolio companies.
In today's crowded market, the key PE differentiator is no longer financial engineering but the ability to identify and cultivate relationships with target companies months or years before a sale process. This provides the necessary time for deep diligence and strategic planning.
During due diligence on a venture firm, asking portfolio founders why they chose that investor is critical. If the answer is simply "they had money," it implies the VC offers no strategic value—like recruiting help or corporate relationships—and is not a top-tier partner.
At the height of the dot-com bubble, top venture capitalists were incredibly stressed and unhappy. The fear of missing out on the next big deal if they took even an afternoon off created immense pressure that overshadowed their unprecedented financial success.
Private equity managers often get psychologically anchored to their purchase price. Instead of cutting losses on a poorly performing asset to redeploy time and capital, they hold on in the vain hope of getting their money back, turning a bad deal into a time-consuming, mediocre one.
Unlike venture capital, which relies on a few famous home runs, private equity success is built on a different model. It involves consistently executing "blocking and tackling" to achieve 3-4x returns on obscure industrial or service businesses that the public has never heard of.
As PE firms shift from generalist to specialized vertical teams, the next generation of leaders lacks cross-sector experience. This creates a risk of poor decision-making and weak trust within the future investment committee, which must opine on deals outside their expertise.
It's easy for a General Partner (GP) to be a good partner when markets are strong and profitable. A GP's true character, integrity, and alignment with Limited Partners (LPs) are only tested when a downturn forces difficult conversations about shrinking profits and unmet expectations.
When market competition compresses returns, PE firms that rigidly stick to historical IRR targets (e.g., 40%) are forced to underwrite increasingly risky deals. This strategy often backfires, as ignoring the elevated risk of failure leads to more blow-ups and poor fund performance.
Limited Partners are often misled by emerging managers with a short track record of a few successful deals. With a small sample size (e.g., 5-6 deals), it's impossible to distinguish between skill and pure luck—the equivalent of flipping heads five times in a row.
When a General Partner offers a GP-led secondary, they shift the crucial decision of when to sell an asset from themselves—the expert—to the Limited Partner. This undermines a core tenet of the LP-GP relationship, as LPs lack the deep asset-level knowledge to make an informed sell-or-hold decision.
When David Swenson published the "Yale Model," many institutions tried to copy it without possessing Yale's resources, network, or manager selection expertise. This led many to chase private equity and hedge funds ill-equipped, resulting in them backing lower-quartile managers and achieving poor results.