Weed Be Crazy Not to Listen – Jesse Redmond

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🎙️🎙️Jesse Redmond is a visionary leader at the crossroads of finance and cannabis, shaping the industry’s future as the Head of Investor Relations and Business Development at LEEF Brands. With a career spanning hedge funds, investment strategy, and cannabis entrepreneurship, Jesse brings a rare fusion of financial acumen and deep industry insight.

Before joining LEEF, Jesse made his mark as a top cannabis analyst and the founder of two hedge funds. He spent over a decade co-managing multiple hedge funds, allocating more than $1 billion across investment strategies and conducting 1,000+ due diligence visits worldwide. His career began at Franklin Templeton, followed by an early role at Fisher Investments, solidifying his expertise in global finance.

In 2016, Jesse pivoted to the cannabis space, founding a Santa Barbara dispensary that quickly became the region’s #1 retailer. Recognizing the growing investment potential in the sector, he launched Higher Calling Consulting in 2020, guiding investors toward the most promising cannabis opportunities. He later served as Head of Cannabis at Water Tower Research, further cementing his reputation as a leading industry strategist.

With a background that spans Wall Street to the dispensary floor, Jesse brings an unparalleled perspective on the cannabis market—one that blends institutional investment experience with hands-on operational success. Today, at LEEF Brands, he continues to bridge the gap between capital and cannabis, shaping the industry’s next chapter.

https://leefbrands.com/

Historical & Prohibition Parallels

1. “Cannabis is following the script of alcohol prohibition, but is the ending the same?” – We’ve seen this movie before with alcohol in the 1920s. The black market thrived, crime surged, and then the government reversed course. Do you see cannabis following the same trajectory, or are we in for a plot twist?

2. “If cannabis is the ‘new alcohol,’ where are we in the timeline?” – Are we in the speakeasy era, the 21st Amendment moment, or still waiting for the federal version of Al Capone to get busted?

3. “During Prohibition, people needed bootleggers. Now, they need financial analysts?” – How does the transition from backroom deals to boardrooms change the investment landscape for cannabis?

4. “If we put cannabis prohibition on trial, what would the closing argument be?” – Imagine you’re defending cannabis against federal restrictions in a high-stakes courtroom drama. What’s your case?

The Future & Epic Potential

5. “What’s the Tesla of weed?” – Is there a cannabis company today that’s poised to do what Tesla did for EVs—disrupt, innovate, and redefine the space?

6. “If cannabis had a stock ticker in 1933, what would it look like today?” – Alcohol stocks exploded post-Prohibition. Should investors look at cannabis the same way, or is there a cautionary tale here?

7. “Cannabis in 2040: Will it be in vending machines, prescribed by AI doctors, or will it still be a ‘gray market’ in some states?”

8. “Will there be cannabis sommeliers?” – Wine has them, whiskey has them—do you foresee a future where cannabis connoisseurs have Michelin-star levels of prestige?

9. “Will cannabis replace coffee?” – With microdosing and functional cannabis, are we heading toward a culture where people start their day with a sativa shot instead of espresso?

Federal Illegality & The Investment Landscape

10. “Wall Street vs. Washington: Who legalizes cannabis first?” – Will financial institutions force legalization before the government catches up?

11. “What’s the real reason cannabis is still federally illegal?” – Follow the money: is it Big Pharma, private prisons, or just political inertia?

12. “If cannabis became federally legal tomorrow, what happens to the market?” – Does it explode overnight, or do we see unexpected turbulence?

13. “How do you manage risk when the rules can change overnight?” – Investing in cannabis is like betting on a game where the referee can change the rules mid-play. How do you navigate that uncertainty?

14. “Does Big Cannabis become the next Big Tobacco?” – As cannabis scales, will we see corporate monopolization, or will craft cannabis hold its ground?

Humorous & Wild Card Questions

15. “If cannabis stocks had a personality, what kind of person would they be?” – Are they the chill surfer, the Wall Street wolf, or the eccentric genius?

16. “What’s your elevator pitch to a 1920s bootlegger about switching to cannabis?” – “Forget gin, my friend. I’ve got something with better margins and less bathtub risk.”

17. “If Snoop Dogg and Warren Buffett started a cannabis hedge fund, what’s the first stock they buy?”

18. “What’s the biggest financial myth about cannabis?” – What’s the misconception that keeps investors from jumping in?

19. “What’s more likely: cannabis being federally legal in all 50 states or the U.S. having its first AI president?”

20. “If the cannabis industry had a soundtrack, what songs would be on it?” – A mix of ‘Smoke on the Water,’ ‘Because I Got High,’ and ‘Money’ by Pink Floyd?

http://linkedin.com/in/jesseredmond

https://x.com/jesseredmond?s=21&t=l-RuYzZ5-PN85Y-SxI7OMw

https://leefbrands.com/

https://x.com/higherexchanges?s=21&t=l-RuYzZ5-PN85Y-SxI7OMw

One on One Video call W/George
https://tidycal.com/georgepmonty/60-minute-meeting

Support the show:
https://www.paypal.me/Truelifepodcast?locale.x=en_US

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Legal Disclaimer / Release of Liability for Podcast:
This content is for educational and informational purposes only. Nothing in this transmission constitutes legal, financial, or professional advice. I am not your lawyer, financial advisor, or telling you what to do.

This podcast documents historical events, analyzes publicly available information, and explores hypothetical scenarios. Any actions discussed are presented as educational examples of how systems work—not as instructions or recommendations.

You are solely responsible for your own decisions and actions. Any application of information p...