How VCs Structure Venture Deals | Paige Soya, Nick Duafala & Scott Stern (Partner, Origin Ventures)

Not all venture deals are created equal, and understanding the fine print can make a significant difference for founders.

In this episode of High Stakes, K Street Capital's Paige Soya and Nick Duafala are joined by Scott Stern, Partner at Origin Ventures, to break down how venture capital deals are actually structured. From SAFEs and convertible notes to priced equity rounds, founder vesting, liquidation preferences, pro rata rights, and anti-dilution provisions, they explain the terms that shape startup financings—and why they matter for both founders and investors.

Along the way, the conversation explores common fundraising mistakes, why complicated cap tables can derail future financing rounds, and how founders can approach term sheet negotiations with greater confidence. Rather than simply defining venture terminology, this episode explains the reasoning behind the structures investors use and how those decisions can influence a company's long-term success.

Whether you're raising your first round, investing in startups, or simply looking to better understand venture capital, this episode offers practical insights into one of the most important—and most misunderstood—aspects of startup fundraising.

In this episode:

• The differences between SAFEs, convertible notes, and priced equity rounds
• How valuation, dilution, and cap tables really work
• Why founder vesting exists and what investors are protecting
• Liquidation preferences, option pools, and anti-dilution explained
• Pro rata rights and why investors negotiate for them
• Common fundraising mistakes founders should avoid
• How to approach your first venture capital term sheet with confidence

Guest:

Scott Stern, Partner at Origin Ventures

Hosts:

Paige Soya, Managing Partner, K Street Capital

Nick Duafala, Senior Principal, K Street Capital