Driving Alpha: Seed Stage Investing and the Importance of Pro Rata Rights with Jason Calacanis

Driving Alpha

Jason Calacanis is the Founder and CEO of early-stage investment firm LAUNCH and real-time business news app Inside.com. A serial entrepreneur, angel investor, and former Sequoia Capital scout, Jason has invested in hundreds of startups, including Uber and Calm, a meditation app now valued at $1 billion. He previously launched Venture Reporter — formerly known as Silicon Alley Reporter — and Weblogs, Inc., which he exited before venturing into angel investing.

Jason continues to shape and influence the tech and investment spheres, sharing invaluable insights through his acclaimed book Angel and podcasts This Week in Startups and All-In. His platform Founder University helps founders get funding and launch their products.

Episode Chapters:

(00:00) Introduction

(01:24) Jason Calacanis shares his experiences as a prolific seed investor

(05:54) How Jason’s Silicon Alley Reporter grew to $12 million in revenue during the dot-com boom

(09:15) The importance of asking insightful questions to uncover a founder’s potential

(12:51) Jason reflects on past investments, including Uber and Open Angel Forum

(14:46) What are the “three Ds” of identifying winners?

(25:24) What are the criteria for identifying successful founder-led companies?

(48:33) Jason explains at-scale seed investing strategy, signaling issues, and beta

(55:44) Jason’s journey to starting LAUNCH Festival after breaking away from Sequoia Capital

(01:10:30) AI adoption in startups, investment climate, and mobile technology

In this episode…

Investing in startups at the seed stage offers immense potential for growth and innovation, but it comes with hurdles and complexities. From portfolio construction to day-to-day management, navigating this terrain requires a keen understanding of the market, a discerning eye for talent, and a strategic approach to decision-making. What can you learn from a technology entrepreneur whose early-stage investments have achieved billion-dollar valuations?

Angel investor Jason Calacanis navigates the complexities of early-stage startups with his 21-person team, serving as a catalyst for hundreds of thriving companies. Drawing from his extensive experience, he delves into the nuances of seed-stage investing, highlighting key factors essential for a successful venture capital firm and the critical importance of identifying exceptional talent and groundbreaking ideas. Additionally, investors must understand potential warning signs that could signal a startup's failure and seek mentorship from experienced investors. Jason also highlights the value of a world-class design and a product outlier in driving sustained growth and market dominance.

In this episode of the Driving Alpha podcast, Steve Brotman sits down with Jason Calacanis, the CEO and Founder of LAUNCH and Inside.com, to explore the intricacies of seed-stage investing. Jason shares his experience as an angel investor, insights regarding venture capital and startups, and highlights the crucial role of mentorship from experienced investors.