Angel Investors vs. VCs | Paige Soya & Dadi Akhavan (Startup-to-IPO Founder)

In this episode of High Stakes, Paige Soya sits down with Dadi Akhavan, a startup-to-IPO founder and angel investor, to break down one of the most important dynamics in early-stage investing: angel investors vs venture capitalists.

While both play critical roles in the startup ecosystem, the way they invest and what they need from their investments iis fundamentally different.

We explore how those differences shape everything from deal selection to decision-making to founder outcomes.

Key themes include:

• Why venture capital funds are structurally driven to pursue “outlier” returns
• How fund size, LP expectations, and mandates influence VC behavior
• Why angel investors have more flexibility in what and when they invest
• How early-stage founders should think about which type of capital to raise — and when
• The tradeoffs between taking institutional money vs. staying in the angel ecosystem
• What “stage of company” really means in practice for fundraising strategy
• How experienced investors evaluate opportunity differently based on structure, not just preference

Dadi also shares insights from his own journey, from building companies to taking one from startup all the way to IPO, and how that experience shapes his approach to investing today.

This episode is a deep dive into the mechanics behind startup funding decisions, and what founders often overlook when choosing between angels and VCs.