Dana Chiles

  • Greater Boston Area, US
Dana Chiles

CEO and President, Daisher-Chiles Companies

Professional Profile

Work History


Daisher-Chiles Companies, Ltd.

Practicing real estate for nearly two decades.  Successfully built several corporations responsible for Real Estate Development, Redevelopment, Construction, Investment and Management. These include Daisher-Chiles Companies, Synergy Capital, and The Quantum Group, Inc

Professional Experience

Mr. Chiles began his career while attending college in the late 1980s.  At this time the real estate market was met with severe crisis.  Mr. Chiles recognized the opportunity, and began working for a real estate affiliate south of Boston. He gained valuable experience in real estate policy, markets, and law, as well as obtaining his real estate broker’s license. 

At the age of 20, Mr. Chiles purchased his first investment property in Brockton Massachusetts for $50,000, as a distressed asset.  His analysis of the industry brought him clear understanding that real estate markets are cyclical, always recover, and that the greatest opportunity for personal, financial and professional growth is during a market depression.  His strategy of strong management, selective assets, and organized resources along with the ability to sustain and survive in a trouble market, has yielded not only short term, but long term significant gain.  This strategy is cornerstone of Daisher-Chiles’ success.

Over time, Daisher-Chiles troubled asset focus has shifted. After amassing dozens of multi-family assets, focus shifted to purchasing troubled commercial apartment complex assets.  These continued acquisitions prompted the development and launch of full-scale in-house management of the several hundred housing units owned by Mr. Chiles. This portfolio provided Mr. Chiles not only with the short term rental income component, but also long term gain expectations with the value appreciation of the larger (and smaller) housing structures.  Average acquisition cost was less than $20,000 a unit.  This ultimately increased to more than $100,000 per unit when the market recovery was complete.

After this real estate market stabilized, Mr. Chiles began acquiring raw land for development purposes.  He purchased single family lots and successfully built construction companies to perform the management and completion of custom built homes.  This effort continued with the purchase of multi-lot housing developments. Mr. Chiles was responsible for all phases of planning, development, infrastructure, construction, marketing and sales.  Mr. Chiles’ companies have been responsible for the construction of hundreds of residential housing units. 

Today Mr. Chiles has redirected some focus toward his rehabilitation company, which expertly specializes in the acquisition and restoration of troubled assets.  This has been achieved through scientific business models, management and databases he has built over the past 18 years, as well as strategic relationships with important lending resources.  His companies act on only a fraction of the opportunities presented on a daily basis, as buying decisions are made selectively.  As a result, Mr. Chiles has built the most successful and revered trouble asset business in the entire state.

Mr. Chiles built his business model with unwavering focus on market diversity.  His strategy has been to develop companies that performed well in all market cycles, but most importantly compensated for one another during market changes. When development is strong and people are buying, rentals are slower.  When the rental market is strong, due to people finding it difficult to buy, then the development is slow.  During all markets, no matter what the economic environment, Mr. Chiles’ companies are thriving.

Below market acquisitions for his development company, great investment portfolio assets, and most importantly redevelopment of troubled assets and bank portfolios have built Daisher-Chiles strong foundation.

This is the second real estate depression Mr. Chiles’ companies have operated in. With the experience, knowledge, scientific business models and management resources, the opportunities for Daisher-Chiles Companies are unparalleled.