In this episode I sit down with Ed Sim, founder and managing partner of Boldstart Ventures, to dig into where AI security, agentic infrastructure, and the venture market are actually heading.

Ed has been an inception-stage investor for nearly 30 years and has run Boldstart since 2010, backing hardcore technology companies across AI infrastructure, cybersecurity, and physical AI. He was the first investor in Protect AI, which sold to Palo Alto Networks in a reported ~$700M exit roughly a year before ChatGPT launched. He is also early in companies like Keycard, Surf AI, and June. About a third of Boldstart's investments are in cyber, so Ed sees this market from the founder and investor side in a way most security conversations do not.

We get into why the era of building raw intelligence is giving way to an era of controlling it, what that means for on-prem models and private evals, and why Ed thinks nearly everything in security is going to get rebuilt from scratch.

In this episode:

- Why a day-one partnership looks different now that anyone can vibe code an MVP
- The Protect AI acquisition and what the first exit in AI security signaled to the market
- Competing as an inception fund against mega-funds writing giant seed rounds
- What founders should actually look for in a venture partner beyond the check
- The shift from building intelligence to controlling it, including routing, post-training, and on-prem deployment
- Why enterprise data, workflows, and private evals are becoming the crown jewels
- Vulnerability chaining, attack path reasoning, and how tools like Mythos are reshaping the security budget conversation
- Agentic identity and why Keycard treats agents as short-lived problem solvers rather than digital twins
- The Surf AI thesis on automated security hygiene and tying every asset back to an owner
- The real bottleneck slowing agent adoption in the enterprise

Chapters:

0:00 Intro
0:35 Ed's background and inception investing
1:57 Day-one partnerships in the vibe-coding era
3:53 The Protect AI exit to Palo Alto
6:14 Competing as an inception fund against mega-funds
9:17 What founders should look for in a VC partner
11:48 From building intelligence to controlling it
15:52 Boldstart's domain-specific model portfolio
16:16 Private evals, context, and memory as crown jewels
17:18 Mythos, vulnerability chaining, and attack path reasoning
20:59 How much access should you give the model
22:07 On-prem context and the autonomous workforce
24:49 Agentic identity and Keycard
28:11 Building brand and community with Insecure Agents
31:30 The Surf AI thesis and automated security hygiene
34:13 The real bottleneck to agent adoption
37:09 The easy button, Palantir, and a multi-model world
38:24 Two types of people in this new era

Connect with Ed:
LinkedIn: https://www.linkedin.com/in/edsim/
Boldstart Ventures: https://boldstart.vc
Ed's newsletter, What's Hot in Enterprise IT/VC: https://www.whatshotit.vc

More from Resilient Cyber:
Substack: https://www.resilientcyber.io
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#aisecurity #agenticai #cybersecurity #venturecapital #appsec

Does restricting frontier AI in the name of safety actually make us less secure? Joshua Saxe joins me to make the case that it does, and that AI cybersecurity will be won through defender adoption, not restriction.

Josh has spent 15 years at the intersection of AI and security. He built and ran the machine learning program at Sophos, then led security for Llama at Meta, covering security post training, evals, agent guardrails, and prompt injection prevention. He recently left to co-found a startup reimagining vulnerability and exposure management agentically. He also writes one of the most cited blogs on AI and cyber policy.

In this episode:
- Why restricting frontier model access harms defenders more than attackers
- How monitored closed models put threat actors at a structural disadvantage
- The jagged frontier, and why attackers don't need frontier models for most of their tradecraft
- The national security and supply chain risks of pushing the world onto Chinese open weights models
- Why exploits don't cause cyberattacks, and which attacker constituencies AI actually unblocks
- The dual use ceiling on guardrails and classifiers
- Where defenders should be adopting AI right now, from access management to SOC automation
- Using agents to burn down the mountain of security technical debt

Chapters:
0:00 Intro
0:42 Josh's background, from blackhat teen to Llama security lead
3:07 The case for diffusion over restriction
6:14 Why restriction hurts defenders more than attackers
10:19 The jagged frontier and what attackers actually use models for
12:49 National security and the supply chain risk of Chinese open weights
16:08 Exploits don't cause cyberattacks
20:20 Where defenders should adopt AI right now
24:20 Guardrails, classifiers, and the dual use problem
27:34 Reimagining vulnerability management with agents
32:17 The structural advantage defenders hold
35:15 Policy wishes and the attacker's Claude Code moment

Follow Josh:
LinkedIn: https://www.linkedin.com/in/joshua-saxe-01845a1
Substack: https://joshuasaxe181906.substack.com

Follow Resilient Cyber:
Substack: https://www.resilientcyber.io
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#aisecurity #cybersecurity #vulnerabilitymanagement #aipolicy #opensourceai

Cybersecurity investor Sid Trivedi of Foundation Capital joins me to dig into AI SOC valuations, services-as-software, moats, and what founders should know heading into Black Hat.

Sid is a Partner at Foundation Capital, where he invests at the seed and Series A stage with a focus on cybersecurity and IT infrastructure. This is our annual pre-Black Hat check-in, and a lot has moved since last year, from massive M&A to record-setting rounds in categories like the AI SOC.

In this episode:
- What has actually changed a year into the AI wave, and what hasn't
- Services-as-software, the $4.6 trillion market thesis, and automating cyber workflows across the SOC, IR, pen testing, and threat intel
- What AI means for cybersecurity jobs and how practitioners should adapt
- Consolidation vs. best-of-breed after Palo Alto's $25B CyberArk deal and Alphabet's $32B Wiz acquisition
- AI SOC valuations, including Seven AI's record Series A and Torq crossing a $1B valuation
- The double-edged sword of big raises and why founders should be cautious about the valuations they accept
- Why you can't simply spend your way to growth in cybersecurity
- Moats and defensibility when frontier labs can push into your category
- The Black Hat Innovator Investor Summit and the Startup Spotlight competition

Chapters:
0:00 Intro
0:52 What's changed a year into the AI wave
2:42 Services-as-software and the AI SOC
9:38 AI adoption and forward deployed engineers
10:57 M&A, platformization, and best-of-breed
14:17 IT and security convergence, plus AI SOC valuations
18:48 Seed-stage risk calculus vs. later-stage investors
21:43 The double-edged sword of big raises
26:20 Why you can't spend your way to growth
29:05 Moats and defensibility in the frontier-lab era
32:25 Deal flow, pricing, and staying disciplined
37:06 Black Hat Innovator Investor Summit
40:17 Startup Spotlight competition
43:28 Wrap-up

Black Hat is offering listeners $500 off registration with code USA500Resilient.

Connect with Sid:
LinkedIn: https://www.linkedin.com/in/siddhanttrivedi/
Foundation Capital: https://foundationcapital.com

Resilient Cyber: https://www.resilientcyber.io
Subscribe for more conversations with security practitioners, founders, and leaders.