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Institutions Evaluate Cannabis While Trulieve CEO Sells Shares

By Shadd Dales On Jun 26, 2026

Shadd Dales and Anthony Varrell hosted a special Friday morning edition of Trade to Black, presented by Flowhub. We begin with Terry Mendez, CEO of Safe Harbor Financial (NASDAQ: SHFS) and his thoughts of the IgniteIt conference. Then Andrew O’Connell, author of the Pristine Capital Substack and a past participant in the U.S. Investing Championship, breaks down new data on Trulieve (NYSE: TRLV) and recent insider activity involving CEO Kim Rivers.

The hosts opened by noting that the DEA had signaled its intention to highlight testimony on marijuana’s medical benefits during the hearing, framing the scientific and medical record as front and center — which both hosts read as the government building a clean, defensible foundation for comprehensive rescheduling to Schedule III.

In the first segment, Terry Mendez, CEO of Safe Harbor Financial (NASDAQ: SHFS), joined fresh off the IgniteIt Conference in Chicago to discuss what he is seeing from institutional banks as they quietly begin preparing for future cannabis exposure. He described a financial sector that is increasingly curious but still cautious, with banks seeking education on how to evaluate the space, what compliance infrastructure cannabis banking requires, and how consolidation among operators will affect deposit relationships and loan demand.

In the second segment, Andrew O’Connell, author of the Pristine Capital Substack and a past participant in the U.S. Investing Championship, returned to break down new data on Trulieve (NYSE: TRLV) and recent insider activity involving CEO Kim Rivers. He explained that her share sales are part of a standard 10b5-1 program announced in March — well ahead of the NYSE uplisting — giving investors a 90-day window before any transactions occurred, with an independent executing broker carrying out the trades and removing Rivers from any discretionary involvement.

He walked through the volume data showing her sales represented five to seven percent of daily trading on several sessions, noted that approximately 91 percent of the first tranche of 1.7 million shares had been completed, and emphasized that Rivers retains roughly a nine percent ownership stake worth an estimated $150 million. Hear the whole interview when you tune in.

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Shadd Dales

Shadd Dales is the Founder and President of The Dales Report and has an extensive background in the business media industry.

His work translates into over 15 years in mainstream media that included roles with BNN Bloomberg, CTV Properties and the iHeart Radio Network.

Shadd is considered one of the leading on air talents in both the cannabis and psychedelic space and has interviewed some of the most notable CEO names in the industry.

Shadd’s vision is to establish a content platform that is equivalent to a mainstream broadcast produced in a format that is relevant for today’s investor.