Deciding whether to invest more capital into a struggling portfolio company is a major point of conflict. The management team advocates strongly for the infusion, believing it can turn things around. However, investor experience shows that such 'bridge' rounds are rarely successful, making it a difficult decision.
Permira's co-CEO highlights a critical challenge in industries with long feedback loops, like private equity: the temptation to prematurely kill initiatives that appear to be failing. The key leadership skill is discerning if a strategy is flawed or simply needs more time to compound.
In today's founder-centric climate, many VCs avoid confrontation to protect their reputation (NPS) within the founder network. This fear of being blacklisted leads them to abdicate their fiduciary duty to shareholders, failing to intervene even when a company's performance is dire and hard decisions are needed.
The worst feeling for an investor is not missing a successful deal they didn't understand, but investing against their own judgment in a company that ultimately fails. This emotional cost of violating one's own conviction outweighs the FOMO of passing on a hot deal.
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.
To ensure robust decision-making, Eclipse requires that if a partner feels strongly against a potential investment, they must join the deal team alongside the champions. This forces a direct confrontation of the risks and ensures that by the time an investment is made, all major concerns have been addressed.
Small funds and solo GPs can gain an edge by not reserving capital for follow-on rounds. This strategy enforces discipline, avoids cognitive biases like sunk cost, and recognizes that the skill set for pre-seed diligence is fundamentally different from that required for later-stage investments.
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.
In a distressed scenario, simply asserting seniority as a junior capital provider is ineffective. You cannot force the majority owner and management team, whom you've just told are worthless, to run the business for your benefit. The only viable path is to renegotiate and realign incentives for all parties to work towards a recovery together.
Deciding whether to back a competitor is fraught with conflict. When the speaker considered investing in Stripe, a Square executive called it a conflict, but CEO Jack Dorsey approved. This shows opinions on threats vary internally, justifying multiple checks before proceeding with a potentially conflicting investment.
A frequent conflict arises between cautious VCs who advise raising excess capital and optimistic founders who underestimate their needs. This misalignment often leads to companies running out of money, a preventable failure mode that veteran VCs have seen repeat for decades, especially when capital is tight.