About Podcast
In a world where AI touches everything from the way we drive to the way we shop why hasn’t it truly transformed the way we manage our money? That’s the question Alexander Harmsen, co-founder and CEO of PortfolioPilot.com, set out to answer. What followed was a bold leap from aerospace and autonomous systems into the deeply personal world of financial advice building a platform that now helps over 30,000 users manage $30 billion in assets. In this episode, Alex takes us behind the scenes of PortfolioPilot’s rapid rise from writing the first lines of code himself to becoming an SEC-registered RIA offering real, personalized, AI-powered financial coaching. He shares how his frustration with generic robo-advisors led to a bigger vision: creating an always-on optimization engine for the everyday investor. With candid insights into startup risk, early product failures, hiring through uncertainty, and building trust in a compliance-heavy industry, Alex proves that sometimes the best ideas come when you’re trying to solve your own problems. Here’s what you’ll take away:
- How to turn a “clunky prototype” into a category-defining fintech product.
- The power of simplification in a world of financial complexity.
- Why real innovation starts with listening not scaling.
- What it means to lead a team through ambiguity (and limited payroll).
- How focusing on user trust, not features, became their biggest differentiator.
Join us for a conversation that’s equal parts technical, tactical, and deeply human perfect for founders, PMs, and curious minds who believe in building not just smarter products, but more empowered users.
- Validating Value Through Real Commitments : Use bare‑bones prototypes and real payments from early adopters to prove true demand.
- Aligning Innovation with Compliance : Embed key legal milestones (e.g., SEC RIA registration) early to unlock features and build trust.
- Inspiring Lean Teams with Vision and Feedback : Drive motivation under tight budgets through rapid pivots, weekly insights, and a shared mission.
- Embedding Continuous Feedback and Agile Pivots : Turn regular beta‑user conversations into data‑driven product adjustments.
- Differentiating with Advanced Modeling and AI : Combine sophisticated recommendation engines with simple, low‑risk UX to stand out.
Special Guest: Alexander Harmsen – Founder & CEO
Location: San Francisco, California, United States
Air Date: July 20 ,2025
Websites:
- PortfolioPilot.com: Take control of your finances with AI-powered insights, tax optimization, portfolio tracking, and more.
- Google Keep: Google Keep is a free note-taking and organization app developed by Google. It’s designed for capturing quick thoughts, to-do lists, reminders, and more.
- Diversification.com: Diversification.com is now the hub for PortfolioPilot’s new initiative focused on improving portfolio diversity and long-term investing discipline.
- Securities and Exchange Commission (SEC): The SEC company verification system allows users to check whether or not a company is registered with the SEC either as a corporation or as a partnership.
- Iris Automation: Our culture revolves around the core values that drive work at Iris every day. A focus on collaboration, growth, hard work, and keeping active and healthy.
Books:
- Blue Ocean Strategy: How to Create Uncontested Market Space and Make the Competition Irrelevant.
- Purple Cow by Seth Godin: Transform Your Business by Being Remarkable.
Producer & Host: Alicia Butler Pierre
Producer & Voiceover Artist: Clarence Levy III
Audio Editors: Olanrewaju Adeyemo and Sabor! Music Enterprises
Sound Design: Sabor! Music Enterprises
Video Editor: Gladys Jimenez
Show Notes: Hashim Tale
Sponsor: Equilibria, Inc.More About Guest, Alexander Harmsen:
Alexander Harmsen is an accomplished entrepreneur and AI-driven finance pioneer with a keen expertise in complex systems modeling and personal wealth optimization. After selling his autonomous‑vehicle software startup in early 2021, Alex leveraged his engineering, physics, and economics background to found PortfolioPilot.com an AI‑powered personal financial advisor that now manages $30 billion across 30,000+ users.
Alex’s journey began at NASA, where he built computer‑vision systems for robotics and ISS experiments, then led Iris Automation from garage‑prototype to a $25 million‑funded, three‑office operation securing regulatory approvals in nine countries before its successful 2021 acquisition. With no formal finance pedigree, he taught himself portfolio theory and regulatory compliance running initial models on his own finances that took hours to compute but delivered game‑changing insights.
A pivotal moment came in late 2021 when he realized that users wouldn’t pay for raw data or calculators they would pay for actionable, personalized advice. That insight drove Alex to secure SEC registration as a fiduciary advisor, turning a prototype “duct‑taped” engine into a fully compliant, subscription‑based product by September 2023. Since then, PortfolioPilot has grown organically through user referrals, strategic media acquisition (Diversification.com), and relentless UX refinement quadrupling advice accuracy and reliability without adding new features.
Leading a multidisciplinary team of data scientists, engineers, and financial experts, Alex emphasizes rapid iteration, psychological insights, and a “purple‑cow” approach to differentiation. His vision blends cutting‑edge AI with user‑centric design to guide self‑directed investors through 401(k)s, Roth IRAs, crypto wallets, and beyond empowering every American to optimize their finances monthly and retire with confidence. Alex’s story underscores the power of resilience, market intuition, and mission‑driven leadership in scaling complex technology into a mass‑market financial coach.
More About Sponsor, Equilibria:
Equilibria, Inc. is a 20-year-old boutique operations management firm. We build the business infrastructure necessary for fast-growing businesses to scale with less pain. With a range of services and products, entrepreneurs can get the operational support and resources they need on demand. 
