TrueLife

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One on One Video Call W/George

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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 presented here is at your own risk. I assume no liability for consequences of actions you choose to take.

By continuing to listen, you acknowledge that this content is educational commentary, that you’re responsible for researching applicable laws in your jurisdiction, and that you’ll consult appropriate professionals before taking any action that could affect your legal, financial, or personal situation.


Creators and Guests

Host
George Monty
GEORGE MONTY George Monty is a podcaster, interviewer, cultural provocateur, and professional trespasser into forbidden questions. He is the creator and host of TrueLife, an ongoing experiment in conversation conducted somewhere between a philosophical laboratory, a psychedelic séance, and the moment at 3:17 in the morning when you suddenly realize the universe has been fucking with you. The premise is beautifully inconvenient: What if reality is stranger than the story we’ve been given about it? Monty has spent years following that question into the wilderness. Not the wilderness of mountains and rivers, but the stranger wilderness behind the eyes: consciousness, psychedelics, artificial intelligence, mysticism, neuroscience, trauma, addiction, technology, language, mythology, power, culture, death, transformation, and the great unresolved mystery of what the hell a human being actually is. His guests come from wildly different worlds: scientists and mystics, philosophers and psychonauts, artists and technologists, researchers and rebels, therapists and troublemakers, people who have spent decades studying reality and people who have simply stared at it long enough to realize something is wrong with the instruction manual. Monty does not interview people to collect answers. He interviews them to find the questions hiding underneath the answers. That is the rabbit hole. He is interested in the moment certainty begins to fracture. The instant a scientist discovers something their textbook did not prepare them for. The moment a mystic realizes language has become too small. The moment a psychedelic experience rearranges the furniture of the self. The moment artificial intelligence forces us to reconsider what intelligence was in the first place. He is suspicious of finished maps. Suspicious of institutions that confuse authority with truth. Suspicious of anyone who claims to have the universe completely figured out. Especially himself. Monty’s intellectual lineage runs through the beautiful troublemakers: Alan Watts, Terence McKenna, William Blake, Carl Jung, Philip K. Dick, Marshall McLuhan, Rumi, the Upanishads, Joseph Campbell, and the long subterranean tradition of people who looked at consensus reality, raised one eyebrow, and asked: “Is that all you’ve got?” But George Monty is not an academic, guru, therapist, prophet, or self-appointed master of consciousness. He is something considerably more useful: a curious bastard with a microphone. A lifelong student of the strange. A collector of impossible questions. A cartographer of the territory that begins where certainty ends. TrueLife is his laboratory, but the laboratory has no walls. Every conversation becomes another experiment. Every guest another doorway. Every strange idea another match struck in the dark. Sometimes the result is philosophy. Sometimes it is comedy. Sometimes it is terror. Sometimes it is revelation. And sometimes, if you’re lucky, the whole fucking architecture starts to wobble. Because beneath all the conversations, all the books, all the theories, all the psychedelics, all the technology, all the arguments about consciousness and civilization and the future, Monty keeps returning to one primitive human impulse: to look at the mystery without immediately trying to kill it with an explanation. That may be the real rebellion. Not believing everything. Not rejecting everything. But remaining curious enough to walk through the door. TrueLife is the experiment. Conversation is the psychedelic. Curiosity is the contraband. Reality is the rabbit hole. And George Monty is still climbing down.

What is TrueLife?

TRUE LIFE is a long-form descent into the questions that become impossible to ignore once the surface of reality starts to crack.

Hosted by George Monty, TrueLife explores consciousness, psychedelics, neuroscience, artificial intelligence, language, technology, power, culture, philosophy, spirituality, trauma, addiction, human transformation, and the strange future of being human.

For more than six years, George Monty has built TrueLife as an independent media platform, bringing hundreds of long-form conversations to a growing global audience. The podcast has produced 850+ episodes, reached 22M+ YouTube views, built an audience of 40K+ subscribers and followers, and accumulated 160K+ podcast downloads. TrueLife has also been recognized by Listen Notes among the top 5% of podcasts globally.

These are not simply interviews. They are encounters with people who have gone far enough into a subject to discover that the subject changes them. Scientists meet mystics. Artists meet technologists. Researchers meet rebels. The personal collides with the planetary.

The central question: What happens when we stop treating reality as fixed?

Across hundreds of conversations, TrueLife follows recurring territories — consciousness → perception → language → technology → power → transformation → the future of humanity.

For seekers, rebels, researchers, creators, entrepreneurs, and anyone who suspects the official story is incomplete.