Driving Alpha: Unveiling the Art of Inception Investing in Technical Enterprise Founders With Ed Sim

Driving Alpha

Ed Sim is the Founder of boldstart ventures, a true believer and partner from inception for bold founders reinventing the enterprise stack. Ed is currently on the boards of Snyk, BigID, Blockdaemon, Protect AI, Env0, and several other cybersecurity and infrastructure startups. Other notable inception investments include Kustomer, where he was on the board until his exit to Meta, Superhuman, Security Scorecard, and Front. Ed also co-founded MState in 2017, an enterprise blockchain lab in partnership with IBM, where seed investments include Fireblocks. He is known for being a partner from inception, helping founders start, scale, and exit while enjoying the process.

Ed has been recognized as a top 10 investor on the Forbes Midas Seed List for the last three years and as the No.1 seed investor in the Business Insider Seed 100 for 2023 and 2024. He also writes the popular weekly newsletter What’s Hot in Enterprise IT/VC, which covers the latest trends in venture capital and enterprise technology. Prior to boldstart, Ed was a Co-founder of Dawntreader Ventures, where he led inception investments in Greenplum (sold to EMC, Pivotal — IPO), GoToMeeting (sold to Citrix), and LivePerson (IPO). He graduated from Harvard with a BA in Economics and was a four-year letterman on the men’s lacrosse team.

Episode Chapters:

(00:00) Introduction

(00:41) How Ed Sim's career blossomed over 25 years in the venture world

(02:40) What does it take to be a successful entrepreneur and investor?

(04:09) New York’s evolution as a tech powerhouse and what it means for enterprise software

(07:13) How pre-seed and seed rounds came to be, and why we need Inception rounds

(11:33) How Ed's lacrosse background shaped his investment philosophy

(18:33) The importance of finding a balance between “steak” and “sizzle” in founders

(22:03) AI’s future and how incumbent companies may compete or collaborate with startups

(25:49) An insider's advice on evaluating companies with “intuitive TAM”

(40:34) The key to sustained content creation discipline and its importance in venture capital

(54:28) Ed's long-term vision for boldstart ventures

In this episode…

What does crafting overnight success stories in the complex tech landscape take? Passion, resilience, and a sharp eye for pioneering technology can ignite the path to building billion-dollar enterprises. Can these same elements apply regardless of market conditions and trends?

Seasoned venture capitalist Ed Sim lays out his blueprint for venture capital triumph, infused with lessons learned from his early days selling kitchenware to standing at the helm of a game-changing tech investment firm. He highlights that the path to industry leadership is paved with a long-term vision, founder empathy, and a focus on problem-solving. With insights on how significant shifts reshaped the stage — such as the adoption of Amazon EC2 and open-source — Ed demonstrates a keen ability to anticipate and leverage the market's evolutionary trends. He offers invaluable guidance to aspiring venture capitalists and seasoned investors alike, proving that relentless commitment and strategic evolution withstand the test of time.

In this episode of Driving Alpha, Steve Brotman chats with Ed Sim, the Founder of boldstart ventures, about Ed’s growth in venture capital and insights into modern tech investments. Ed shares the strategic thinking propelling his journey, emphasizing early participation in startups and an unwavering dedication to enterprise infrastructure. He also elaborates on the critical role his passion for sports and grit played in forging relationships and sustaining success through economic cycles.