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

  #LetsActuate, #ColtonCray, #Litquidity, #LitquidityVentures, #VentureCapital, #StartupLife, #DeepTech, #HardTech, #FrontierTech, #FutureOfWork, #Aerospace, #Defensetech, #Entrepreneurship, #Innovation, #FounderStories, #StartupStories, #Authenticity, #RiskTaking, #CustomerObsession, #ProductLedGrowth, #MemeticCulture, #BrandBuilding, #ProblemSolving, #CommunityBuilding, #AI, #ConsumerTech, #TechInvesting, #Investor, #Founders, #BrandStrategy, #BuildingInPublic, #GrowthMindset, #StartupAdvice, #Storytelling, #VC

Venture capital, private equity, and family office models are starting to converge – and the rules are changing.

In this episode, we sit down with Ron Diamond, Chairman & CEO of Diamond Wealth, host of the Family Office World podcast, and trusted advisor to a syndicate of 100+ leading family offices (ranging from $250M to $30B AUM).

Ron unpacks the rise of long-horizon, patient capital, why legacy models in private equity are due for shakeup, and the challenges/opportunities as $84T in wealth transfers to a new, tech-savvy generation.From building trust to the importance of direct investments, the value of educational communities, and the role family offices can play in emerging markets like deep tech and space.This conversation is a can’t-miss for founders, fund managers, and family investors navigating the next wave of private capital!

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Chapters

[00:00] Introduction: Ron’s Journey from Drexel to Diamond Wealth

[03:00] Why Family Offices? Lessons from Wall Street & Hedge Funds

[08:00] Patient Capital: Permanent, Generational Wealth

[11:00] Building Trust: Why Relationships & Reputation Matter

[16:00] Family Office Infrastructure & Minimums

[20:00] Sourcing Deals, Specialization, and VC Lessons

[26:00] Deep Tech, Space, and the Younger Generation's Edge

[34:00] Generational Transition & Embracing Technology

[42:00] The Future: Reviving In-Person Connection, Building Community

[50:00] Personal Goals, Societal Impact & Closing Thoughts

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Connect with Ron Diamond & Diamond Wealth

• Diamond Wealth
• Ron Diamond on LinkedIn
• Family Office World Podcast

• 
  

  –––

  Follow the Let’s Actuate! Podcast

  Subscribe: letsactuate.com

  Youtube: @letsactuate
  

  Connect with Actuate Ventures

  Website: actuateventures.co
  LinkedIn: @actuateventures
  X: @actuateventures

  
  

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  This episode was brought to you by Siemens Software

  To find out more, email: james.gernatt@siemens.com

  Launching a deep-tech startup is not only complex, but also painful to progress through the technical milestones associated with product development. Many companies run out of cash due to lengthy product development cycles and failure to hit technical milestones.

  This is why we’re excited to let our listeners and ecosystem connect with our podcast sponsor, Siemens Industry Software. Specifically, Siemens Xcelerator for Startups software platform (that's Xcelerator with an “X”) helps organizations digitally transform faster.Their startup programs help companies avoid growing pains with access to scalable software. With programs and bundles to support Product Engineering and CAD, Data Management, Simulation, Test, Regulatory and Design Control, these solutions grow with you without eating into your burn rate.

  Mention Actuate Ventures referred you for up to 97% off!

  
  

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  This podcast is for educational purposes only. Nothing in this episode constitutes investment advice.

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  #LetsActuate #FamilyOffice #VentureCapital #PrivateEquity #EmergingTech #LongTermCapital #DeepTech #Podcast #Trust