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

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

Author: Paige Soya May 8, 2025 Duration: 38:41

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.


Behind every major innovation, there's usually a risky bet and a tense conversation that made it happen. High Stakes pulls back the curtain on those pivotal moments by focusing squarely on the world of early-stage venture capital. Instead of abstract theory, each conversation pairs a founder who has lived the grind with an investor who has backed the vision, creating a dynamic and often revealing dialogue. They tackle the specific trends and tough questions shaping the venture space right now, from evaluating a team's potential to navigating a market downturn. You'll hear the nuanced strategies, the candid mistakes, and the real-world compromises that define building and funding a company from the ground up. This podcast is built for anyone curious about the mechanics and human drama of startup investing, offering a genuine sense of how capital flows to ideas and what it truly takes to succeed. Tune in for unscripted perspectives that clarify how high-risk decisions are made and what both sides learn when the stakes are at their absolute highest.
Author: Language: en-us Episodes: 64

High Stakes
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