When Venture Deals Go South: Inside the Realities of Startup Failures, Wind Downs, Write-Offs, and Zombie Companies

Not every startup story ends in a big exit. Sometimes, despite best efforts, companies miss key milestones, burn through their runway, or become what investors call “zombie startups.”

In this episode of High Stakes, host Paige Soya sits down with Tony Chan, partner at ORIC and seasoned venture capital and M&A expert, to explore the hard truths of venture investing. Tony shares insights into what happens when deals go south—and what investors can (and should) do when startups are struggling.

Key Points From This Episode:

• Common examples of how companies can handle early closures and exits.

• The importance of early, honest conversations when things aren’t going to plan.

• Why founder optimism and investor caution can be hard to reconcile.

• Founder trust in VCs: how it hinges on operating experience and credibility.

• Navigating misaligned incentives among early and late-stage investors.

• What really happens behind the scenes before and after a board meeting.

• How disciplined investors avoid FOMO and spot underfunded opportunities.

• Why some startups are turning to even-sided mergers instead of IPOs.

• The growing role of secondaries in private market liquidity.

• How VC is shifting as private equity becomes more accessible to retail investors.