Episode 7 now available!

Ep 07 - Nick Myers, Director of AI Innovation, Recovery.com

Previously Cofounder & CEO, RedFox AI

​Healthcare AI Exit: RedFox AI Success Story​

Nick Myers discusses selling RedFox AI to recovery.com, building constrained AI for healthcare, his approach for finding success and support as a founder in Madison, and the future of work with the acceleration of AI.

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Key learnings

Build to Be Rich or King?​
Nick's mentor asked him early on whether he wanted to be "rich or king" - a question that shaped his entire exit strategy. Choosing to be rich means knowing when to get out of your own way and prioritizing the company's success over personal control. This mindset prepared him for acquisition opportunities rather than clinging to founder status.

Constrained AI Prevents Healthcare Disasters​
RedFox AI's "constrained RAG" system only pulled information from verified medical documents, preventing the hallucinations that plague general AI models. In healthcare, you can't afford AI making up statistics or procedures - patients' lives depend on accurate information. This technical approach became their key differentiator and acquisition value.

Proximity Creates Unexpected Opportunities​
Nick's decision to work at StartingBlock coworking space directly led to his acquisition by recovery.com, who worked just 20 feet away. Being physically present in startup ecosystems creates serendipitous conversations and relationships that remote work can't replicate. Sometimes the best opportunities come from casual hallway conversations, not formal networking events.

Accessibility Requires Intentional Design​
RedFox built web-based AI to avoid app download barriers, supported 90 languages with real-time dialect detection, and accommodated ambient noise. True accessibility means removing every possible friction point for users, especially in healthcare where stress and urgency are high. Don't assume users will adapt to your technology - your technology must adapt to them.

Genuine Networking Beats Transactional Relationships​
Nick's networking philosophy centers on asking "what can I do for you?" rather than focusing on what others can provide. This genuine approach to relationship-building created a network of people who wanted to help him succeed. Authentic interest in others' work and challenges builds stronger professional relationships than purely self-interested networking.

AI Job Displacement Needs Policy Preparation​
Nick warns that AI will eliminate entry-level positions within 3-5 years, creating massive unemployment that current institutions aren't prepared to handle. Unlike previous technological shifts, AI's exponential improvement curve means faster, more dramatic workforce changes. Policymakers need to start preparing safety nets and retraining programs now, not after the displacement begins.

Free Resources Exist But Require Navigation​
Wisconsin offers numerous free startup resources like Merlin Mentors, UW's Small Business Development Clinic, and the Law and Entrepreneurship Clinic. However, founders often struggle to find these resources without insider knowledge of the ecosystem. The challenge isn't lack of support - it's creating better pathways for new entrepreneurs to discover what's available.

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What is the Startup Wisconsin Podcast?

A new show where you can learn about Wisconsin's growing tech scene. Hear the stories of startups, founders, investors, and the incredibly generous people making it happen every single day.

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Upcoming episodes 👀

• Lonni Kieffer (Building and Growing SmartCert)
• Christina Henderson (Launching Reliable Residence)
• Jillian Bichanich (Growing Cubbi and Launching a 2nd Startup)
• Shantanu Singh (AI Tools for Legal with Obviate.ai)
• Laura Strong (Starting Valency Fund)
• Jessica Silvaggi (UW Milwaukee Research Foundation)

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Have questions?
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