Colton Cray: Winning in Venture Today – Respecting Risk, Founder Mindsets, Real Traction, and the Flight to Authenticity

What do Wild West stunt shows, M&A deal rooms, and meme-driven syndicates have in common? Colton Cray, now General Partner at Litquidity Ventures, joins Let’s Actuate to share his journey from the Pistoleros stage at Traildust Town to the frontlines of frontier investing.

Colton explores what it means to practice “risk respect,” which separates great founders from the merely bold. He explains why deep expertise in problem spaces and customer relationships – not engineering in stealth – create real traction, especially in tough fields like aerospace, defense, and applied sciences.

You’ll hear how he thinks about technical risk versus market risk, why successful investing means understanding the story behind the numbers, and how “flight to authenticity” is changing both consumer and investor appetites across tech. The group discusses the value of community, learning from hype cycles, and the signals that matter most for building companies that last.

Takeaways

• Practicing “risk respect” is essential for both founders and investors

• Real traction comes from problem obsession and engaging with customers, not from stealth or pitch decks

• Great companies require systems for decision making and a commitment to learning from failure

• The next tech and investment cycle is driven by a flight to authenticity – community, honesty, and experiences that ring true
• Success in tough markets requires understanding compliance, relationships, and how to drive adoption

Sound bites

• “The stunt man to VC pipeline remains strong.”
• “The biggest risk of all is not taking a risk.”

• “Flight to authenticity is what I'm calling it, and that's my story and I'm sticking to it.”

Chapters

00:00 - Introduction

08:21 - From Live Stunt Actor to Venture Partner

15:06 - Choosing a Corporate Law Career as a Stepping Stone

21:57 - Superpowers: Risk-Taking and Failure Tolerance

29:15 - Investment Focus: Consumer, Retail, E-commerce, and Frontier Technologies

38:41 - Building Authentic Solutions

40:54 - The Potential of Deep Tech

43:22 - The Importance of Knowing Your Customer

46:39 - The Role of Product-Led Growth

48:34 - Timing and Strategy in Entrepreneurship

50:09 - The Shift Towards Transparency and Collaboration

53:06 - Understanding Deep Tech

57:04 - The "Flight to Authenticity"

01:00:30 - Excitement in Aerospace and Defense

01:01:34 - The Theme of Authenticity

Guest Profile:
Colton Cray is General Partner at Litquidity Ventures and a former M&A attorney with a quadruple major from the University of Arizona and Rothman Scholar at USC Law. He brings startup, digital media, and fintech experience to his role leading deals in frontier tech, built world, and enhanced digital services.

Colton is an advocate for founder-market fit and “risk respect,” and is an advocate of taking the unconventional path forward.

Colton on LinkedIn
Litquidity Ventures

References:

• ⁠Litquidity Store⁠

• ⁠Pistoleros Wild West Stunt Show⁠
• ⁠Traildust Town⁠

Tags

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