Navigating Venture Rounds and M&A

​Most founders know how to build. Far fewer know how to navigate the financing milestones and exit conversations that determine whether all that building pays off.

​Join us for a conversation with Sam Shank, the Co-Founder and CEO of HotelTonight — the last-minute hotel booking app that raised multiple venture rounds before being acquired by Airbnb in a deal valued at nearly $400M. Sam has lived the full arc: early-stage fundraising, scaling through venture rounds, and ultimately negotiating a high-stakes acquisition with one of the world's most recognized brands.

​In this session, we focus on the questions that matter most:

• ​Raising Venture Capital the Right Way — What Sam learned across multiple rounds about what investors actually want, when to raise, and how to avoid the mistakes that derail otherwise strong companies;

• ​The M&A Conversation — How acquisition interest develops, what makes a company an attractive target, and how founders should think about the process before it starts;

• ​Lessons From the Other Side — What Sam would do differently with Stand, and what he got right — navigating the transition from independent founder to acquired company.

​There'll be time for Q&A at the end. Most useful for founders currently fundraising or approaching a growth inflection, and anyone curious about how the path from venture-backed startup to successful exit actually unfolds.

​Speakers:

• ​Sam Shank: Sam is a serial entrepreneur and the Co-Founder of HotelTonight, which he built from launch to a ~$400M acquisition by Airbnb. He has since served as a Visiting Partner at a16z Speedrun and is currently co-founder of Stand, an AI-native homeowners insurer. He is also an active angel investor across consumer, marketplace, and software companies.

​About Us:

​Backed by a16z and Y Combinator, Metal is an AI-native operating system for founders raising venture rounds.