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The Highs and Lows of Venture Rounds

Two founders who've collectively raised over $300M+ share their unfiltered experiences navigating the fundraising process — the pivotal breakthroughs, the unexpected setbacks, and how they closed their rounds.

March 25, 2026
Virtual
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https://youtu.be/B94WE9GMvvw
The Highs and Lows of Venture Rounds

​This session focuses on the realities of raising venture rounds — the wins, the setbacks, and everything in between. Two founders who have collectively raised over $300M+ join us to share their unfiltered experiences navigating the fundraising process.

In this session, we focus on the two most important questions that founders are looking to understand:

  • The Highs — What were the pivotal moments, relationships, or signals that unlocked meaningful investor interest and kept the process moving?
  • The Lows — What were the unexpected challenges, and how did these founders navigate setbacks to ultimately close their rounds?

The session will leave time for a brief Q&A at the end to make the discussion interactive. The event is most useful for founders currently fundraising or preparing to raise their next venture round.

This event is organised by Metal and will include the following speakers:

  • Ahmad Omar — Co-founder & CEO, Sully AI Ahmad has raised $40M building Sully AI, an AI-native platform transforming how healthcare operates. He's in the trenches of one of the hardest industries to crack — and doing it at scale.
  • Sasha Orloff — Co-founder & CEO, Puzzle Sasha has raised $270M+ across multiple companies and is currently building Puzzle, a modern financial foundation for startups. He's seen both sides of the cap table and brings rare pattern recognition to the fundraising process.