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Social Engineering Beats Your Stack: Fix Identity or Get Breached
A single phone call to a help desk shouldn’t sink a global brand—yet it happens. We dig into how social engineering bypasses expensive tools, why identity verification matters at the exact human moments work gets done, and how to measure cyber risk before it becomes tomorrow’s headline. With Peter Segerstrom of Traceless (https://traceless.com/) —a CTO turned advisor who’s audited stacks for acquisitions and built teams from a spare bedroom to scale—we unpack the messy reality of software in payments and fintech: open‑source dependencies, brittle architectures, migrations that stall, and the quiet warts you inherit when you buy code along with revenue.
Christopher Dryden, Esq., traces with Peter how a simple phone call can topple complex systems and why identity verification sits at the heart of modern security. Peter shares a CTO’s view on auditing tech in payments M&A, grading risk, and building Traceless to protect real transactions in real time.
• social engineering as a primary breach vector
• why tech diligence now drives payments and fintech M&A
• lessons from scaling a startup to operational maturity
• auditing architecture, dependencies and maintainability
• open source as foundation and risk surface
• risk grading frameworks buyers can act on
• what cyber risk means for vendors and SaaS reliance
• real‑time identity verification for help desks and workflows
• AI as force multiplier for attackers and defenders
We walk through the practical M&A playbook: inventory the stack, map data flows, assess maintainability, and grade risks so executives can decide what to fix, mitigate, insure, or avoid. Peter explains how a “technical Carfax” reframes negotiations, saving buyers from hidden liabilities and helping sellers prepare cleanly. We also talk vendor risk and why relying on major SaaS platforms can be safer than running your own server—while still demanding least privilege, strong logging, and incident plans that assume someone will eventually pick the wrong link or trust the wrong voice.
Then we widen the lens to Traceless and the identity problem at the core of modern breaches. Real‑time verification for customers, partners, and employees closes the easiest door attackers use: impersonation. From teenager pranksters to nation‑state zero‑days, the threat spectrum is wide, and AI now powers both sides—faster phishing and reconnaissance for attackers, smarter analysis and stress testing for defenders. The takeaway is clear: build verification into business workflows, treat architecture as a living system, and make risk visible with honest grading.
If this conversation helps you think differently about due diligence and operational resilience, follow the show, share it with a colleague, and leave a quick review so more people can find it.
**Matters discussed are all opinions and do not constitute legal advice. All events or likeness to real people and events is a coincidence.**
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Chapters

1. Social Engineering’s Costly Breaches (00:00:00)

2. Show Opening And Guest Context (00:01:03)

3. Why Tech Diligence Now Drives Payments M&A (00:02:10)

4. Peter’s Path From Hacker To CTO (00:03:48)

5. Scaling A Startup And Ops Lessons (00:06:30)

6. Auditing Tech In Acquisitions (00:09:10)

7. Open Source As Hidden Backbone (00:12:15)

8. Risk, Warts, And Grading Systems (00:14:20)

9. Traceless: Origins And Focus (00:16:32)

10. What Cyber Risk Really Means (00:18:30)

11. Reliance On SaaS And Vendor Security (00:20:30)

12. Identity Verification And Help‑Desk Attacks (00:22:10)

13. Zero‑Days To Prank Calls: The Spectrum (00:24:20)

14. Does AI Help Attackers Or Defenders (00:26:00)

15. Closing Notes And Disclaimers (00:28:30)

82 episodes