High Functioning Podcast

How do you go from bankruptcy to selling $1 billion in private aviation? Jay Sapovits (Founder, Ink’d) shares his raw, unfiltered journey from a crippling gambling addiction to high-stakes business success.

Topics:

• The $1B Sales Secret: Specific tactics for closing high-net-worth clients.

• The Ego Trap: Why success is more dangerous than failure for your mindset.

• The Pivot: Leaving a glamorous jet career to sell "swag"—and...

Boston comedian and creator Gary Bolles (@boyfromboston617) joins Jason to talk about growing up in Southie, getting clean, and finally committing to stand up after his sister’s death pushed him to change his life. He explains how therapy, endless open mics and reps turned into paid shows, crowd work and a late-blooming comedy career, and why he is okay living back at home at 44 while he builds something real.

They dig into how club...

In this High Functioning episode, Jason sits down with Eskar President Michael Hunnewell to unpack what “winning as a small operator” really means. Michael explains how group purchasing works in grocery, why license caps matter less than COGS, and how private label and MAP pricing change shelf strategy. They walk through real examples from Massachusetts and talk about what happens to independents when large players drive costs down...

Bobby Nuggz has spent more than a decade inside New England cannabis as a writer, event producer, and community connector. In this High Functioning episode he talks about the festival days, the early medical markets, the shift into legal, and what he has seen brands and media do right and wrong. The conversation touches on concentrates, lab testing, ethics, and why he still chooses community over clicks. It is a grounded look at ho...

Clean Up Your Data gives operators a practical safety playbook. Jeff Rawson, PhD of the Institute of Cannabis Science, explains why measuring work beats tracking inventory, how to design clear recalls, and how to reduce hardware lead risk. Use these steps right away.

You’ll learn• Seed to sale vs real safety• Clear recall lists people can follow• Fast checks for lead in hardware

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Holly Alberti joins Jason to talk about building with community first. She shares early advocacy work in Boston, how education programs set a strong base, and what she learned when a large project collapsed. Holly also explains how past brand work shaped her approach to launches and partnerships.

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Jordan and Mike Whittaker (The Weedaker Group) explain how they help teams launch, train, and operate in a tough market. We cover compliance vs. operations, why inspectors and towns see rules differently, and how to plan events that feel safe and welcoming. They also share lessons from Morocco and how New Dia near Fenway Park became a true community hub with rotating art and a weekly award-winning show recorded on site.

You’ll Learn...

Chris Barnicle, NCAA All-American and Olympic Trials competitor, shares what happens when the pursuit of speed leads to burnout and how he came back from it.

He talks about his years running for Arkansas and New Mexico, training in Kenya, and competing at the national level. Chris explains how injuries and overtraining forced him to rethink his approach and focus on recovery, reflection, and sustainability.

This conversation is for a...

Aidan explains how art-first products and per-sale commissions support creators. We cover store-level discovery, the Homie Pack, collectible booklets with magnets, sourcing new artists, and plans for gallery shows using the original paintings.

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What makes rosin different, and why does it matter? In this episode of the High Functioning Podcast, Ben McCabe, Chief Operating Officer at Sweetgrass Botanicals, explains the truth about solventless rosin.

Ben shares how Sweetgrass built transparency into its model with live demos, how solventless shows the full character of a strain, and why some cultivars shine while others do not. He also talks about why solventless is the natur...

Dan Mondello, CEO of Rank Really High, breaks down why many dispensary websites do not convert and what to change first. We cover simple site fixes, smarter use of menus and POS data, and how ADHD shaped his approach to focus and leadership.

What you’ll learn

• The top reasons sites fail to convert

• What to stop chasing if growth is flat

• Page elements that raise add-to-cart and pickup

• A clear plan for search, content, and ads

Full ...

Rob DiFazio, Navy veteran and CEO of CNA Stores, shares how to grow a purpose-driven retail and cultivation business. From veteran-first hiring and community fundraising to smart inventory planning and extraction expertise, Rob shows what it means to build a company with integrity.

🎙️ In This Episode✔️ Retail growth and inventory sell‑through tactics✔️ Building a flat leadership culture✔️ Fundraising for the Pan‑Mass Challenge✔️ Ex...

From Dorm Hustle to Enterprise
Joe Khoury went from 3D-printing rolling-tray phone cases in his college dorm to architecting data and ERP platforms behind $850 million+ in regulated-tech transactions. Along the way he survived a $10 K customs seizure and co-launched AI compliance agents for multi-state operators.

What You’ll Hear:

• Dorm-room prototype & pre-sell validation

• Customs-seizure lessons in risk management

• Building m...