Investors who fund AI startups at inception see where enterprise AI is headed years before most business leaders. New AI bets force three decisions onto the enterprise agenda: rent or own your AI, securing autonomous agents, and choosing vendors that will survive the coming shakeout.
In Episode 928, Michael Krigsman talks with the No. 1 ranked seed investor in the Business Insider Seed 100, two years running: Ed Sim, founder and general partner of boldstart ventures. The conversation maps what current early-stage investment reveals about where enterprise AI is headed.
Sim wrote the first check into Snyk, backed Protect AI at inception before its sale to Palo Alto Networks for more than $700 million, and manages over $1.1 billion at boldstart. He writes What's Hot in AI/Infra/VC, a weekly newsletter on enterprise AI and infrastructure. This is his third CXOTalk appearance; he last joined in August 2024 to discuss early-stage investing in enterprise AI.
What we will cover:
Where early-stage AI investment is flowing, and what those bets reveal about the technology reaching enterprises over the next two to three years
Rented versus owned intelligence: when frontier APIs win and when specialized models trained on your own data win
Open-weight models and the real tradeoffs on cost, control, and lock-in
Security for the agentic era, seen through the investor's market map the week after Black Hat
The coming shakeout among AI vendors, and how buyers can judge which companies will survive
AI economics after the subsidy era: measuring ROI per workflow rather than tokens
Watch Episode 928 with Ed Sim live on Friday, August 7, 2026, at 1:00 PM ET on CXOTalk. Join this interactive discussion and ask your questions!
This episode is brought to you by Gartner IT Symposium/Xpo™
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JOIN LIVE AND ASK QUESTIONS
Friday, August 7
10am PT / 1pm ET / 7pm CEST
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EPISODE PARTICIPANTS
Ed Sim is the founder and general partner of boldstart ventures, an inception-stage investor in enterprise software with more than $1.1 billion under management. This is his third appearance on CXOTalk.
Michael Krigsman is a globally recognized analyst, strategic advisor, and industry commentator known for his deep expertise in business transformation, innovation, and AI leadership.
RECENT EPISODES
UPCOMING LIVE SCHEDULE
See www.cxotalk.com for the latest updates to our live programming schedule.
Aug 7: Ed Sim, Founder and General Partner, boldstart ventures
Aug 21: Saral Jain, SVP of Engineering & Chief Information Officer, Snap
Aug 28: Tamar Yehoshua, Chief Product and AI Officer, Atlassian
Sept 11: Paula Goldman, Chief Ethical and Humane Use Officer & EVP, Product, Salesforce
Sept 18: Patrick Bangert, Chief AI Officer, Occidental Petroleum