Resilient Cyber

CISOs have a stack of tools but no system built to run the security program itself. Mike Armistead wants to fix that.

In this episode I sit down with Mike Armistead, co-founder and CEO of Pulse Security AI and a longtime security founder behind Fortify and Respond Software. We dig into why the security leader has never had a system of truth the way the CFO has an ERP and the CRO has a CRM, and how an agentic layer on top of the existing tools can finally close that gap. Mike is measured about where AI gets to decide and where the human stays in the seat, and he shares what surprised him most from research with more than 80 senior practitioners and corporate directors.

In this episode:
- Why two exits later Mike came back to build a third company around the AI wave
- The silos that left CISOs with an acronym soup of tools and no way to run the program
- What a system of truth for the CISO actually means and how it layers on top of existing structured and unstructured data
- Where agents do the heavy lifting on regulatory monitoring, vendor intelligence, and status reporting
- Governing the guardrails, not the keystrokes, and why closing the loop still involves people
- What corporate directors actually want to hear in the 15 to 20 minutes a CISO gets each quarter
- The findings that stood out, including that 55% of boards have never defined the cyber risk they are willing to accept, and only 12.5% of CISOs are very confident the board leaves with a true picture of the risk
- Institutionalizing the tribal knowledge every security program runs on

Chapters:
0:00 Intro
0:18 Mike's background and two prior exits
1:08 Why the AI wave pulled him back
2:21 Why the CISO has no system to run the program
4:09 Starting at the program level, not the SOC or AppSec
5:28 What a system of truth for the CISO means
8:19 Speaking the language of the business
9:09 Where AI does the heavy lifting on a typical Tuesday
11:57 Govern the guardrails, not the keystrokes
15:44 Bringing deputies into the conversation
16:46 What the research with senior practitioners found
20:37 Boards, risk tolerance, and the reporting gap
24:57 AI as a double-edged sword for security leaders
25:35 Joanna Burkey and institutionalizing tribal knowledge
27:31 A year from now for the security leader

Guest links:
Mike Armistead on LinkedIn
Pulse Security on AI

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Alex Pinto, who leads Verizon's DBIR team, joins me to break down the new Breach Impact Study and what data breaches actually cost organizations.

For years the industry has argued past itself on breach costs. One camp says the market doesn't care, the other says a single breach ends your business. Alex and his team finally got their hands on roughly 70,000 cyber insurance claims through CyberAcuView, and the Breach Impact Study puts real numbers behind the question. In this conversation we dig into what the data shows, where it stops, and how a security leader should actually use it.

Alex Pinto runs the Data Breach Investigations Report team at Verizon Business and has been building the report for close to a decade. The Breach Impact Study is the team's first focused spin-off from the DBIR.

In this episode:
- How the Breach Impact Study came together and why the DBIR team finally got cyber insurance claims data
- Why the study measures insurable loss as a floor, not a ceiling, of real economic impact
- The case for reporting medians over averages, and why the team refuses to publish the average
- Business interruption versus contingent business interruption, and why downtime moves the needle
- Whether an $83,000 median breach impact sends executives the wrong message
- The SMB paradox, where the smallest companies take the hardest proportional hit
- What the claims data does and does not show about AI on offense and defense
- Third-party risk, coverage sub-limits, and the single biggest takeaway for security leaders

Chapters
0:00 Intro
0:24 Meet Alex Pinto and the DBIR team
2:51 Launching the Breach Impact Study
3:26 Getting cyber insurance claims data
7:32 Why insurable loss is a floor, not a ceiling
11:14 Medians over averages, and why the average is meaningless
15:13 Business interruption vs contingent business interruption
19:49 Does an $83K median send the wrong message?
22:44 The SMB paradox and the cybersecurity poverty line
26:05 Where AI shows up, offense vs defense
34:48 The CVE explosion and marketing hype
36:59 Third-party risk and coverage limits
41:34 Wrap-up

Guest links
Alex Pinto on LinkedIn: https://www.linkedin.com/in/alexcpsec/
Alex Pinto on X: https://x.com/alexcpsec
Verizon DBIR and Breach Impact Study: https://www.verizon.com/business/resources/reports/dbir/

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#cyberrisk #databreach #cyberinsurance #ransomware #aisecurity #dbir

What happens to security investing when vulnerability discovery becomes continuous and exploitation windows shrink from weeks to hours? I sit down with Chenxi Wang of Rain Capital to dig into it.
Chenxi is the Founder and Managing General Partner at Rain Capital, a venture fund focused on early-stage cybersecurity companies. She's been a Carnegie Mellon professor, a Forrester VP, and a strategy leader at Intel Security and Twistlock, and her portfolio includes companies like Claroty, ProjectDiscovery, Ox Security, runZero, and Straiker. She closes out my July run of conversations with security investors.
In this episode:
The AI Exploit Age and why vulnerability discovery is becoming continuous
Guardian Agents and the case that it takes an AI to govern an AI
Separating AI agent identity from traditional machine identity
The signals that predict enterprise adoption for early-stage security startups
The barbell funding market and the squeeze on Series B and C
What security leaders should do differently over the next twelve months
Connect with Chenxi:
 LinkedIn: https://www.linkedin.com/in/chenxiwang88/
Rain Capital: https://raincap.vc/
Rain Capital Insights: https://raincapital.substack.com
Subscribe to Resilient Cyber for more conversations with security practitioners and leaders: https://www.resilientcyber.io

Bugcrowd founder Casey Ellis joins me to dig into what AI is actually doing to bug bounties, vulnerability discovery, and open source security. We get into his "slopdemic" framing, the curl bug bounty saga, VDP readiness, the pentest market correction, and where security research policy heads next.
Casey Ellis is the founder of Bugcrowd, co-founder of disclose.io, and a board member of the Security Research Legal Defense Fund. These days he advises and invests through Tall Poppy Group and works at the intersection of security, AI, and policy. His argument is that the vulnpocalypse was already here, and AI has made the cost of both finding and reporting vulnerabilities collapse at the same time.
In this episode:
Casey's path from building Bugcrowd to advising, investing, and policy work
Why more practitioners need to get involved in policy, and why law is just code
The slopdemic vs. the vulnpocalypse, and what actually changed in submissions
AI lowering the bar for a broader, less predictable pool of threat actors
Daniel Stenberg, curl, and maintainers below the security poverty line
The lightning rod vs. rockets distinction between VDPs and bug bounties
The pentest market correction underway from AI pricing pressure
Collapsing OODA loops, hack-back, CFAA reform, SRLDF, and disclose.io
Chapters:
0:00 Intro and Casey's background
 2:56 Why practitioners belong in policy
 6:22 The slopdemic vs. the vulnpocalypse
 9:40 AI lowering the bar for threat actors
 11:47 Open source, curl, and the security poverty line
 15:37 VDP vs. bug bounty readiness
 19:20 The pentest market correction
 24:20 What breaks first in vulnerability management
 27:20 Hack-back and non-cooperative defense
 28:43 A near-term playbook for security leaders
 31:40 CFAA, SRLDF, and disclose.io
Connect with Casey:
 LinkedIn: https://www.linkedin.com/in/caseyjohnellis
Blog: https://cje.io
disclose.io: https://disclose.io
Bugcrowd: https://www.bugcrowd.com
Resilient Cyber: https://www.resilientcyber.io
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Jon Sakoda of Decibel joins me to break down AI's impact on cybersecurity startups, venture funding, and why endpoint is the Super Bowl of cyber.
Jon is the Founding Partner at Decibel, an early-stage firm backing technical founders in security and infrastructure. He started his career founding IMlogic, an IM security company acquired by Symantec, then spent over a decade at NEA working with companies like Cloudflare, MongoDB, and HackerOne before launching Decibel. We got into why he thinks AI is only magical if you have a magic power, why Decibel led a $100M seed into Ent, and where the firm is placing its next bets.
In this episode:
Why Decibel operates like the Navy SEALs next to the big platform funds
The founder community model and finding the early believers among CISOs
What separates the founders who finish now that AI lets everyone start
Ent's $100M seed and the self-driving moment for endpoint security
Telling genuinely AI-native companies apart from AI washing
AI eating venture capital and why cyber's best years are ahead
Open models, frontier labs, and why the cat is out of the bag
The agentic SOC, Dropzone AI, and driver assistance vs. self-driving
Startup consolidation cycles and being an N of one
How buyers and job seekers should evaluate early-stage vendors
Decibel's next bets, from novel AI models to resilience and cyber insurance
Chapters:
0:00 Intro
 0:32 Jon's background and founding Decibel
 2:25 Big platform funds vs. specialized firms
 3:56 Founders helping founders and early believers
 6:22 Scaling beyond the early adopters
 7:40 Who finishes the marathon in the AI era
 10:19 Founders from outside cyber
 12:21 Ent's $100M seed and the endpoint bet
 14:53 AI-native vs. AI washing
 17:04 AI is eating venture capital
 18:55 Open models vs. frontier labs
 22:41 The agentic SOC and Dropzone AI
 26:03 Consolidation and the startup cycle
 29:22 How buyers should evaluate young vendors
 31:43 Decibel's next bets and cyber resilience
 34:11 Game Day at Black Hat
Connect with Jon:
 LinkedIn: https://www.linkedin.com/in/jonsakoda/
Decibel: https://www.decibel.vc
Subscribe for more conversations with security practitioners and leaders, and find my writing at https://www.resilientcyber.io