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
-
Subscribe to the Podcast:
-
Find From Angel to Exit on Apple Podcasts, Spotify, Google Podcasts, or wherever you listen. Be sure to hit “Subscribe” so you never miss an episode.
-
-
Newsletter & Exclusive Content:
-
Sign up for the free newsletter at eckfeldt.com/podcast for episode transcripts, bonus insights, frameworks, and community updates.
-
-
Connect with Bruce & the Community:
-
LinkedIn: Bruce Eckfeldt
-
Instagram: @bruce_eckfeldt
-
Email:
-
Popular Podcasts
Stuff You Should Know
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.
My Favorite Murder with Karen Kilgariff and Georgia Hardstark
My Favorite Murder is a true crime comedy podcast hosted by Karen Kilgariff and Georgia Hardstark. Each week, Karen and Georgia share compelling true crimes and hometown stories from friends and listeners. Since MFM launched in January of 2016, Karen and Georgia have shared their lifelong interest in true crime and have covered stories of infamous serial killers like the Night Stalker, mysterious cold cases, captivating cults, incredible survivor stories and important events from history like the Tulsa race massacre of 1921. My Favorite Murder is part of the Exactly Right podcast network that provides a platform for bold, creative voices to bring to life provocative, entertaining and relatable stories for audiences everywhere. The Exactly Right roster of podcasts covers a variety of topics including historic true crime, comedic interviews and news, science, pop culture and more. Podcasts on the network include Buried Bones with Kate Winkler Dawson and Paul Holes, That's Messed Up: An SVU Podcast, This Podcast Will Kill You, Bananas and more.
Dateline NBC
Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com