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
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Creative Structures w/ Becki DeGraw | Wilson Sonsini Startup Legal Basics

Sep 4, 2025 • 26 mins

Today’s show: Wilson Sonsini Partner Becki DeGraw returns to Startup Legal Basics with Jason. This time, they dive into the *“have” companies* — the breakout startups with multiple term sheets, competitive valuations, and unusual deal terms. From founder voting proxies to mandatory follow-on investment clauses, Becki breaks down the creative “off-menu” structures showing up in today’s financings, and what founders and investors need to watch for. Whether you’re a founder navigating investor FOMO or a VC competing to get on the best cap tables, this conversation will give you insight into the new rules of the game.

Key Points

  • Legal strategies in startups must adapt to dynamic market conditions, especially as they navigate changing regulations and investor expectations.
  • The surge in "pay to play" financing rounds reflects the current market's demand for startups to grow into their high valuations or face significant dilution.
  • Mid-market M&A activity is increasing as large tech companies face regulatory hurdles, suggesting a potential shift in acquisition strategies to focus on smaller, more feasible deals.
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