When you drop contracts, strategy docs, or source code into ChatGPT, who actually sees your prompts?

In this episode of Inside the Silicon Mind, Firas sits down with Jonathan Mortensen, founder and CEO of Confident Security, to unpack the hidden cost of using AI at work: the fact that what you send to AI tools is not end‑to‑end encrypted and may be retained or even used to train models. Jonathan, a two‑time founder with exits to a cybersecurity firm and Databricks, is now building “you bring the AI, we bring the privacy” – private inference modelled on Apple’s Private Cloud Compute, where even the server cannot see your data.

You’ll hear how today’s AI workflows expose legal documents, trade secrets, and customer data, and how cryptography, anonymisation, and remote attestation can lock that back down. You’ll also hear Jonathan’s lessons from previous startups, why “you’re in the business your customers think you are,” and how AI risks like deepfakes, prompt injection, and cognitive atrophy are reshaping how we think about security and trust.

In this episode:

- AI tools introduce serious privacy risks for sensitive business data.

- Confident Security aims to make AI inference private, modelled on Apple’s cryptographic approach.

- Anonymising traffic and proving what code is running are key to protecting user information.

- The founder mindset behind Confident Security is driven by a desire to create real value and “do things the hard way.”

- Learning from customers – including “you’re in the business your customers think you are” – is essential for product development.

- AI technology raises new authenticity concerns for consumers, from deepfakes to AI‑generated “slop.”

- Agentic browsing, prompt injection, and AI‑generated code present emerging security challenges.

- Iteration and fast feedback loops are vital, whether you’re building AI infra or the fastest plane in history.

- Understanding the market requires constant learning, adaptation, and asking for feedback.

Chapters:

00:00 The privacy dilemma in AI usage

02:46 Confident Security: Apple‑style privacy for AI prompts

05:58 The founder mindset: independence, grit, and doing things the hard way

09:12 “You’re in the business your customers think you are”

12:11 Deepfakes, prompt injection, and consumer AI risks

14:47 Overusing AI and cognitive atrophy

18:20 Skunk Works, iteration, and engineering mindset

Book recommendation:
Skunkworks by Ben Rich

About Jonathan Mortensen

Jonathan Mortensen is the founder and CEO of Confident Security, a company building private inference for AI workloads. Before Confident Security, he founded Gyroscope, a reinforcement learning startup acquired by a cybersecurity firm, and a serverless Postgres company acquired by Databricks.

About the show

Inside the Silicon Mind takes you behind the scenes with the founders, CEOs, and VCs building the future of technology. Every week, Firas Sozan sits down with the operators and investors rewriting the rules – from deep‑tech startups to the security challenges created by AI.

Hosted by Firas Sozan.
Powered by Harrison Clarke.

🔔 Subscribe for more deep dives on:

• AI and the future of software

• Venture capital and company building

• Developer tools, infrastructure, and engineering careers

YouTube: https://www.youtube.com/@InsideTheSiliconMind

Apple Podcasts: https://bit.ly/apple-itsm

Spotify: https://bit.ly/spotify-itsm

Follow the host on LinkedIn:

https://www.linkedin.com/in/firassozan/

Website links:

https://www.harrisonclarke.com/

https://www.harrisonclarkeventures.com/

https://thepmfplaybook.com/

#AIsecurity #AIprivacy #ChatGPT #Cybersecurity #DataPrivacy