Mass Hole Donuts co-founder Peter Gladstone

Crazy Money with Paul Ollinger

This episode is about working for fun, love, and legacy. Peter Gladstone is the Co-founder of Mass Hole Donuts, bakers of gourmet donut holes that celebrate the people, traditions, and spirit of Boston and Massachusetts. After 20 years in consumer marketing with companies like Gillette, P&G, and the Boston Beer Company (aka, Sam Adams), Peter retired and is now building Mass Holes because, he says, it’s fun, and he wants to contribute to the culture of his hometown. When he’s not establishing his Boston institutions, he is a Senior Advisor at the Harvard Innovation Labs where he advises consumer-facing ventures. Peter and I (Paul, host of show and writer of notes) were classmates at Dartmouth’s Tuck School of Business. That is where I developed my appreciation for his creative mind and wacky and wicked good sense of humor. We talk about the difference between working to pay your bills and working on a passion project, the role of humor in the corporate world, how he and his team survived pandemic, and how he defines success now that he has “enough.”

✍🏽 Read Paul’s Substack here. ✍🏽

🎤 See Paul’s upcoming comedy shows here. 🎤

🍩Visit Mass Hole Donuts website here. 🍩

🍪 See Mass Hole’s Instagram here. 🍪