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Meet a Member: Rudy Dajie

Updated: Apr 7, 2021

TiE Boston

Oct 21, 2020·5 min read

Continuing with our feature series on the members of TiE Boston, we spoke with TiE Boston Charter Member, Rudy Dajie, Founder & Managing Member at Grey Holdings and former CEO & Partner at Apothecare Pharmacy, about his journey and what led him to TiE.

Tell me about yourself.

I was born in Quincy, Massachusetts, and lived there until I was 9. From there I moved to a small town called Princeton, located outside Worcester, Massachusetts. In 2003 I graduated from Massachusetts College of Pharmacy and Health Sciences (MCPHS University) in Boston as a pharmacist. After graduating, I participated in a fellowship program with Rutgers University in Marketing Research for Ortho-McNeil for a year. The program really helped hone my entrepreneurial aspirations and encouraged me to do more than fill scripts on a bench. Through the program, I successfully brought the Leva-Pak to market, which is similar to Z-Pak but with the drug Levaquin as opposed to Azithromycin.

After graduation, I worked in pharmaceutical sales for Ortho-McNeil for about a year — until an opportunity came up to be a district manager for CVS Pharmacy in the Worcester area and oversee twenty-four stores. During my two years with CVS, I learned a lot about corporate structure and how to run a business. However, it was very limiting in what you could do as an individual since everything was corporate-run. Another opportunity came up to leave the Worcester area and work for a very large independent long-term and retail pharmacy in Connecticut. While working there for a number of years, I learned a lot about how to do things without a large corporate budget, such as creating new systems and developing purchasing functions. In 2012, I decided it was time to do this for myself. I went to a broker and I found a long term care pharmacy in Brockton for sale. At age thirty-three, I navigated getting a Small Business Administration loan and purchased the pharmacy. I worked seven days a week to get the pharmacy on the path it needed to be. After six or seven years of hard work, I built it into one of the largest independent pharmacies in New England by focusing on serving behavioral health providers. We were working with about $50 million in revenue when I sold the business to a private equity firm.

How did you get involved with TiE Boston?

I decided that TiE Boston would be a good fit because I’m a serial entrepreneur, I’ve exited my business, and acquired substantial net worth. I’m not engaged in working anywhere else. I want to take the bumps on the head and the things I’ve learned throughout my journey to be able to help other entrepreneurs accelerate and get where they need to go. I also want to invest in businesses that seem interesting to me.

I am seeking roles as an engaged investor, where I may act as a board observer or strategic advisor. Being able to sit at the table to see what’s going on and how we can build something innovative and exciting really interests me. The structure in which TiE presents companies is great. I’ve already invested in three companies and I’m acting as an advisor to two of them. TiE Boston is a great organization that brings quality companies that are in need of investment and assistance to its members. I’m looking forward to growing my engagement with the organization.

What obstacles have you faced in becoming an entrepreneur?

My first challenge was during the New England Compounding Center (NECC) crisis. I just bought my own pharmacy for $5 million, and because of concerns with compounding caused by the NECC, the Massachusetts Board of Pharmacy shut down many compounding labs, including Apothecary's. We brought in a consultant to re-tool our operation and regain the confidence of the board, which recognized our commitment to safety and allowed us to resume operations. Another challenge involved reporting mandates that made us look like we had a higher level of dispensing errors. Once again, we had to engage a consultant to demonstrate how we went above and beyond to mitigate dispensing errors and that the errors were very minimal considering the volume of business we were doing. You will encounter many obstacles in trying to build your business. You can either shy away and not figure out how to move past them or you can push forward. It’s always about thinking outside the box, working within the parameters that exist, and being creative.

What advice would you give to entrepreneurs who want to follow in your steps?

Be an expert in your field and be unique in what you’re trying to accomplish. When focusing on behavioral health, I logistically did things differently than large companies and our strategies led to greater profitability. Understand your market dynamic and establish a niche that makes sense to you, and one that you can prosper in without fighting with everybody. Be tenacious in what you want to accomplish. Set goals and make sure that you actually achieve them and that they are top of mind. You can’t have fifteen different smaller goals. You must have one or two overarching goals that are the goals you need to accomplish no matter what. Even if the wheels are falling off, you need to have your mind set on the things that you are going to accomplish. I always wanted to be the biggest and best at everything. To do that, you can’t make the business about something that’s convenient for you. You have to decide and understand that to be successful or to grow, you have to make sacrifices.

What are you currently working on?

In 2018, I sold my business to a private equity firm. I continued to serve as the CEO but later made the decision to exit the company. I’m very engaged in commercial real estate and I’m constantly expanding my portfolio in Massachusetts. I have a number of office buildings in Brockton, a building in Foxboro, and residential spaces in Milford and Boston. I’m currently looking to acquire an office/commercial space in Hanson, Massachusetts.

What are you looking forward to for the future?

I plan to stay engaged in the pharmacy space and I will continue to grow my real estate portfolio. I’m exploring my options, and if the right opportunity comes up in the near future, I may once again take an executive-level role, including as a CEO of a large organization or pharmacy company. I am also interested in pharmacy automation and the different robotics that pharmacies use to dispense products. I look forward to keeping my hand in the pharmacy sector.

Thank you to Rudy for sharing his story. To learn more about TiE Boston and how to get involved, check out or reach out to

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