How two immigrant-family entrepreneurs built lasting businesses from scratch

Executive overview

Most entrepreneurs chase revenue before they've earned the right to it. Gregory Zamfotis built Gregory's Coffee to 36 locations by doing the opposite — learning every job first, refusing to blame external factors, and staying present when it was hardest.

The conversation surfaces a practical philosophy: vertical integration beats outsourcing quality, passion beats strategy for long-term endurance, and collaborations only work when both sides genuinely win.

The core advantage is obsession — knowing your craft so deeply that you see what others miss the moment you walk through the door.

From donut shop to law school dropout

• Father immigrated from Greece, ran serial F&B businesses in New York — donuts, delis, panini shops
• Gregory grew up doing deliveries in lower Manhattan at age seven, absorbing operations without realising it
• Excelled academically through law school; assumed he'd practice law
• First law job felt effortless but joyless — completed assigned work in two hours and had nothing left to care about
• Asked his father for the keys to one sandwich shop across from his law school; ran it better, saw his 10,000 hours add up
• Mother cried when he quit law; grandmother kept calling him "the lawyer" for years after

The founder as last line of defence

• Knows how to fix espresso machines, plunge toilets, drive the delivery truck
• During a 2011 blizzard, baked product at the 24th Street store and carried it through the snow to a hotel block that had no food
• Being able to do every job removes fear — if the whole team walked out, operations could still run
• GaryVee parallel: drove a $3 case of wine to an elderly customer in Bergen County, missing tens of thousands in sales but building company culture
• Blame is a trap; if something fails inside your four walls, you hired the people and set the conditions

Leading without fear

• Has never yelled in 17 years
• Father had staff who stayed for 40 years in an industry with near-zero retention — modelled that respect was the mechanism
• Feedback is delivered as observation, not criticism; team knows he's pointing out what they missed, not catching them doing wrong
• Ran 18 locations with only three corporate employees; micromanagement was a survival mechanism, not a choice
• Delegating now requires consciously unlearning the habit of doing everything himself

Adapting under pressure

• During COVID, stopped blaming the environment when stores were slow — noticed customers who weren't coming in were going somewhere else
• Revamped food program, repackaged bags, restructured the menu around fewer but more complete options
• Pre-COVID: one or two deliveries a day per store; post-COVID: dozens — had to rebuild packaging and delivery standards from scratch
• Delivery ratings improved significantly once the team treated it as a core competency rather than an afterthought

What makes Gregory's tick

• Tagline "see coffee differently" means refusing to copy the standard playbook
• Five non-negotiables for every store: delicious product, fast service, great customer service, hot temperature, clean space — all five at once
• Vertically integrated: coffee roasted in-house, baked goods made from scratch, chai brewed on-site, pumpkin spice made with real pumpkin puree
• Operates as the logo — "Greg from Gregory's" is inseparable from the brand, which creates accountability and connection but no anonymity
• Walks into every store with the same sensors firing: POS speed, cleanliness, staff awareness, foot traffic patterns, storefront visibility

On collaborations

• Collaborations must align in values first; reach and revenue are secondary
• Analogy: the best wines blend multiple grapes because no single one delivers everything — a good collab is the same
• One-day activations with influencers drive a single traffic spike, then nothing; sustained content and product integration create lasting impact
• The VeeFriends Jolly Jack-O pumpkin spice chai latte collab worked because it created a new drink, not just a logo placement
• GaryVee's rule: mentally become the other party and ask what you'd actually say yes to — stop trying to win the deal

Staying passionate at scale

• Passion isn't a feeling; it's what makes you put in hours that aren't directly tied to today's revenue
• Doing something you love increases the probability of success — not a guarantee, but the only reliable edge over time
• Growth happened incrementally: one store, then maybe more, then DC in 2017, then the Northeast corridor
• 36 locations; 37th opening in Darien, Connecticut; expansion targets Rhode Island, Boston, Delaware, Virginia