In this episode of Future Secured, Michael Gianarakis, Co-founder of Assetnote and now Chief Product Officer at Searchlight Cyber, unpacks the full startup journey: from bootstrapping a company in Australia to leading enterprise product strategy after a global acquisition.
With over 17 years in offensive security and a regular speaker at DEFCON, BSides, and Hack in the Box, Michael offers a practical view on building cybersecurity products that matter. He explains why Assetnote emerged from real customer demand, why they said no to VC funding, and how long-term success was built through trust, ruthless pragmatism, and outcome-driven execution.
We cover lessons in customer retention, product-market fit, AI in cybersecurity and managing the acquisition process. Michael also reflects on founding team dynamics, documenting processes for scale and staying focused when acquisition interest becomes a distraction.
Whether you’re a cybersecurity leader, founder, or product builder, this episode delivers concrete lessons for building and scaling technology that lasts.
Takeaways
- 17+ years from pen testing and red teaming to product leadership.
- AssetNote was built from customer feedback and real-world demand.
- Bootstrapping preserved control and optionality.
- Retention comes from trust, value, and workflow integration.
- AI is a tool, not a fad; outcomes beat hype.
- Acquisitions are resource-heavy but manageable with preparation.
- Strong, ego-free founding teams win over time.
- Documentation and lean processes smooth operations and diligence.
- Product-market fit = sell it, retain it, scale it.
- Ruthless pragmatism is a core operating principle.
Sound Bites
- “We didn't take any investment.”
- “Don't just blindly take advice.”
- “It's all about ruthless pragmatism.”
Chapters
00:00 — Introduction to Michael Gianarakis and AssetNote
02:40 — The Journey of Bootstrapping a Startup
05:23 — Navigating Investment Decisions and Growth
08:21 — Understanding Market Fit and Customer Validation
11:17 — The Decision to Sell: Timing and Considerations
13:57 — Lessons Learned from the Startup Journey
16:48 — Building Trust and Customer Relationships
19:45 — Creating Value and Retention in Cybersecurity Products
24:18 — Building Competitive Advantage in Security Products
25:10 — The Role of AI in Security
29:02 — Navigating the Acquisition Process
34:45 — The Dynamics of Co-Founders
42:08 — Scaling a Lean Startup
43:25 — Structuring a Successful Acquisition Deal