About This Episode
Jason Lee sits down with Brian Herr, founder of Startup Starting Blocks and a longtime security and industry advisor, on what actually separates a cyber program that is being managed from one that just looks busy. Brian runs and advises security across a portfolio of companies and sits on boards as an advisor, so he sees the funding conversation from both chairs.
They get into the five levers that show up in every board meeting, why he starts a new program by interviewing the CEO, CFO, and technology leader separately and mapping business processes instead of technology, the two-to-three slide board pack with the receipts kept in the appendix, why the rush to AI is repeating the rush to the cloud, how rebuilding a stack around integration cut one company's spend nearly in half, and what a security career looks like when AI has absorbed the entry-level work.
“Cybersecurity doesn't have to be expensive. But if it's not going to be expensive, it has to be well thought out.”
Brian Herr, Startup Starting Blocks Inc.
In This Episode
- 01Five levers decide funding: protecting existing revenue and contracts, protecting new revenue, protecting people and community, protecting operations and efficiency, and handling regulatory and contractual risk. Which one ranks first depends entirely on the industry.
- 02Start with the business, not the stack. Interview the CEO, CFO, and technology leader separately about the most critical processes, and expect the answers not to line up. Then run a recovery workshop as if the whole place is gone and build the dependency tree back.
- 03Two to three slides for the board, with the technical receipts in an appendix. Boards do not want bits, bytes, and wires. They want confidence that the business is understood and the path from detection to recovery has already been walked.
- 04Cybersecurity does not have to be expensive, but cheap has to be designed. Most stacks run at roughly ten percent utilization with heavy overlap. Rebuilding one around tools that natively integrate cut spend nearly in half and dropped time to response to minutes.
- 05The rush to AI is repeating the rush to the cloud, and the entry-level rungs are disappearing. New talent has to arrive closer to tier two, and adaptability plus genuine human communication now decide who stays on a shrinking team.
About the Guest
Founder · Startup Starting Blocks Inc.
Brian Herr is the founder of Startup Starting Blocks Inc. and a security and industry advisor who runs and advises cybersecurity programs across a portfolio of companies. He presents to boards in some organizations and sits on the board as an advisor in others, and his work spans program design, board reporting, cyber insurance, and rebuilding tool stacks around integration rather than best-of-breed sprawl. He is also a longtime mentor to Blind Spot host Jason Lee.
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