This Week in Startups
This Week in Startups
Jason Calacanis covers startups, tech, markets, media, and all the hottest topics in business and technology. He also interviews the world’s greatest founders, operators, investors, and innovators.
Jason Calacanis
PodcastAI
PodcastAI

Market Update and Trends w/ Becki DeGraw | Wilson Sonsini Startup Legal Basics

Aug 28, 2025 • 26 mins

Today's show: Wilson Sonsini Partner Becki DeGraw returns to Startup Legal Basics with Jason to break down what’s happening in today’s startup market. From excess dry powder on the VC side to companies struggling to “grow into” their valuations, Becki shares what founders need to know about deal terms, pay-to-play provisions, and the shift from the 2021 heyday to today’s more structured environment. • Why down rounds and structured deals are becoming more common • How “pay-to-play” works (and why it’s showing up so often now) • The psychology of VCs vs. founders during tough fundraises • What the M&A landscape really looks like in 2025 v Legal provisions investors are using to protect themselves in today’s talent wars Whether you’re a founder preparing for your next round or an investor navigating tougher terms, this conversation will help you understand the new realities of startup fundraising.

Key Points

  • The slowdown in later-stage funding rounds has led to an accumulation of dry powder, prompting investors to seek new opportunities and bridge rounds to support companies that haven't grown into their high valuations.
  • The rise of "pay-to-play" provisions in down rounds is becoming more common, where investors who do not participate in new funding rounds may see their preferred stock converted to common stock, often at a punitive conversion rate.
  • The regulatory environment has become increasingly challenging for large tech companies to navigate, leading to a rise in mid-market M&A activity as smaller deals face fewer obstacles and lower costs.
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