The men’s fashion boutique Drinkwater’s Cambridge in Porter Square is an artfully curated collection of garments that aren’t just made but engineered, says Gary Drinkwater, who co-founded the company with his wife in 2004. Currently in his 60’s, the company now is hitting its stride as its owner reaches retirement age.

Like many entrepreneurs who have spent their lives building up a brand, there is a question of what will become of the business when the visionary is gone. Businesses throughout Boston have shuttered in recent years for lack of a succession plan. Louis, the store founded by Drinkwater’s mentor Murray Pearlstein, closed down in 2015 after three generations of ownership spanned 85 years. Pearlstein took over the business from his father in 1950 and his daughter, Debi Greenberg, took over in 2003 when Pearlstein was in his 70’s.  Ten years later despite being profitable, Greenberg closed the business “to pursue other things” she said in an interview with Boston.com. For the large majority of Boston’s 40,000 small businesses few of them will change hands to a second generation.  

Drinkwater, however, sees a futrue for his business even beyond his tenure. Looking out of his storefront on Mass Ave, he points out that local university students are dressing better, while older professionals are sporting more casual attire in the workplace. As a result, the product mix in recent years has changed from 70% men’s suits and 30% outdoors dress to sharing that retail space at about 50/50. The store has also benefited from greater demand for American made apparel. Drinkwater says customers are astonished when they learn many of his products are made in the USA. That astonishment has led to “thriving” conditions with his small business etching close to $1 million in annual revenue.

Kevin Mulvaney, professor at Babson College, says "small business with sales less than $1 million are largely dependent on the owner putting in 60 -70 hour work weeks, which may not align with the lifestyle of a new owner." Mulvaney and his colleagues at Babson College have pioneered education on small business issues including mergers and acquisitions, however they focus on companies with $3 – 10 million in sales. "Any less than that, the existing owner is essentially selling a job as opposed to a scaleable company" said Mulvaney. 

In the 20 years while Drinkwater’s Cambridge has been serving the community, other clothing retailers have shut down. A customer post on StyleForum.net calls Mr. Drinkwater’s store a “Jewel”. Several other posts and many positive review on the customer review site, Yelp.com, suggest that Mr. Drinkwater has indeed built a brand that is important to a growing number of people. Drinkwater says he wants to find someone capable of bringing the brand forward. “Whether or not we grow to be a national brand, we absolutely can, but I’ll leave that for the next person to decide”.