What if your financial advisor had no ego, no sales pitch, and no fear of a market crash? Just data, logic, and objective guidance designed around your life?

In this episode, Shubho sits down with Alexander Harmsen, CEO of PortfolioPilot.com, a personal AI financial advisor that’s helping over 30,000 users manage $30B+ in assets—and quietly revolutionizing how everyday investors make decisions.

We go deep into the psychology of money, how AI can help you stay rational when markets get volatile, and why financial tools need to feel more human to actually be effective.

Alexander also shares the origin story of PortfolioPilot, what he learned scaling Iris Automation, his time building with NASA, and how he thinks AI will reshape the future of personal decision-making in everything from investing to health.

What We Cover:

• Why Alexander originally built PortfolioPilot just for himself and why thousands now rely on it
• How PortfolioPilot uses AI to eliminate financial bias and offer tailored, transparent recommendations
• The emotional traps people fall into with investing and how AI helps you navigate them
• Real stories of user psychology (including the guy with 40% of his net worth in Tesla)
• Lessons from building regulated AI systems (and why explainability matters more than hype)
• Startup wisdom: what Alex learned building Iris Automation and raising $30M+
• Why personalization, not general intelligence, is AI’s most underrated superpower
• The power and misunderstanding of tax-loss harvesting
• The future of AI-powered financial tools (and why “gamification” isn’t always the right goal)

🔥 Special Offer for Listeners:

Try PortfolioPilot Gold FREE for 1 month

→ Use promo code PODCAST at checkout

Resources & Links:

• 💼 PortfolioPilot.com
• 🧠 Alexander on X/Twitter: @alexharm
• 📺 PortfolioPilot on YouTube
• 🧑‍💼 Alexander on LinkedIn
• 📚 Books Mentioned:
• Spin Selling by Neil Rackham
• Crucial Conversations by Patterson, Grenny, McMillan & Switzler

Connect with the Show:

• 💬 Instagram: @deartechpodcast
• 💼 LinkedIn: Dear Tech Podcast
• 🌐 All links: linktr.ee/thedeartechpodcast

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