Today's episode explores three ideas that caught my attention:

1. The courage to admit ignorance can be a competitive advantage - Trey's willingness to ask "dumb" questions in healthcare settings was one of the key distinctives that allowed him to learn and grow so quickly.
2. Personal pain often drives conviction in healthcare entrepreneurship - Trey noted healthcare found often lost loved ones or had bad experiences, resulting in higher-than-average grit.
3. Relationships are everything healthcare adoption - Despite compelling ROI data, an innovation’s success often hinged on finding internal champions willing to take personal risks on new solutions.

I explore these ideas and more with Trey Bowles, Founder and Managing Partner of the Bowles Investment Group and co-founder of 1845 Venture Studio. After spending three years as Managing Director at Techstars, where he overcame his initial healthcare investment reluctance to build expertise in digital health and med devices, Trey now champions a venture studio model that sits between bootstrapping and traditional VC. His unique perspective comes from building multiple organizations while simultaneously serving as co-chair of the North Texas Angel Network, giving him rare insight into both the founder and investor experience across Texas's rapidly growing entrepreneurial ecosystem.

During our conversation, Trey shares:

• The healthcare sales discovery framework that actually works - moving from "here's my solution, where would you put it?" to "what are your biggest problems?" followed by systematic needs mapping before any product presentation.
• The relationship-first healthcare market entry strategy - identifying that success requires finding specific individuals within health systems who are willing to try something new, not just institutional buy-in.
• How to leverage angel networks as subject matter expert resources - transforming group investing from capital aggregation into knowledge-sharing platforms that reduce individual due diligence blind spots.

Connect with Trey

LinkedIn

Stuff We Reference

• Dallas Entrepreneurship Center
• DFW Startup Week
• Eagle Venture Lab
• Ryan

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All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice.