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
• 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.

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Timestamps:

(0:00) Becki DeGraw joins Jason for Startup Legal Basics

(1:12) The “perfect storm” shaping today’s startup market

(4:30) Companies struggling to grow into 2021 valuations

(6:31) Why down rounds and structured deals are rising

(8:59) Pay-to-play explained: what happens if investors don’t participate

(15:43) The mid-market M&A wave vs. big tech acquisitions

(20:37) Talent wars, acqui-hires, and protective legal provisions

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Check Out Wilson Sonsini: https://www.wsgr.com

Check out all of the Startup Basics episodes here: https://thisweekinstartups.com/basics

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Follow Becki:LinkedIn: https://www.linkedin.com/in/rebecca-degraw-639bbb62/

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Follow Jason:

X: https://twitter.com/Jason

LinkedIn: https://www.linkedin.com/in/jasoncalacanis

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