13: Inside Cannabis Private Equity: Scalable Models, Smart Terms, and Investor Strategy

In this episode, Bruce Eckfeldt interviews Jordan Youkilis, founding partner of Key Investment Partners, to explore how cannabis investing offers unique challenges and opportunities for founders. Jordan shares his journey from traditional finance to cannabis private equity, highlighting lessons in capital deployment, deal structuring, and scaling businesses in tightly regulated environments.

Key Takeaways

• Profitable, cash-flow-positive cannabis businesses attract more investor interest than high-growth, unprofitable ones
  
• Capital scarcity in cannabis allows investors to negotiate better terms and lower valuations
  
• Section 280E taxes heavily penalize cannabis businesses, affecting valuation and deal viability
  
• Strong due diligence processes and institutional-grade practices enhance investor confidence
  
• Founders must plan capital raises 12–18 months in advance, especially in tight funding markets
  
• Misjudging market cycles and over-raising can lead to damaging down rounds
  
• Understanding investor fund cycles helps founders better tailor pitches and timing
  
• Warm introductions and strategic networking greatly improve investment access

Links & Resources

• Jordan Youkilis

  • Website: keyinvestmentpartners.com
  • LinkedIn: Jordan Youkilis
    
  • Podcast: Cannabis Unlocked

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