McGuire Alumni Five Questions | John Drachman '03

Nov. 9, 2020

John Drachman is responsible for the Waterford Property Company’s commercial division and capital raising activities. Since starting his predecessor firm, Stillwater Investment Group, in 2014, Drachman has acquired and been a partner in over $650 million of office, retail, and apartment assets in Southern California. To acquire these assets, he has created and developed joint venture partnerships with high net-worth private investors, family offices and institutional equity funds while leveraging his strong relationships within the brokerage community to source opportunities. Prior to founding Waterford, Drachman was a Vice President with Greenlaw Partners in Orange County, where he sourced and managed a portfolio of real estate assets throughout Southern California and Arizona. He began his career as a commercial real estate broker with Grubb & Ellis after earning his Bachelor of Business Administration from the University of Arizona. He went on to earn his MBA degree, as well as his Master in Real Estate Development from the University of Southern California where he is now an adjunct faculty member. He is an active member of NAIOP, and an avid swimmer and golfer. He currently resides in Newport Beach with his wife, Laura, and their two children. 

Five Questions with John Drachman '03

Q. What is most surprising about being an entrepreneur? 

A.  How you have to understand every aspect of a business not just a specific skill set when you work for someone else. Each day you have to be an HR specialist, Marketing specialist, IT specialist, Finance Specialist, etc. When you work for someone else you typically have a specific role you focus on which makes things much easier. When you are an entrepreneur you are constantly putting out fires from a variety of different things and only once you have grown in size can you bring in specialists to handle certain tasks. Even then you are still required to have knowledge of those issues since the buck stops with you. It is a never-ending rollercoaster ride but I would never want to do anything else. 

Q. What was the most important lesson you learned in the Entrepreneurship Program? 

A. Always be selling your vision while course correcting your vision, meaning you have to be a fantastic sales person who can articulate a vision for your company. But you have to be flexible when you get constructive feedback that shows your plans might not be the best or work. It is a hard skill to learn to be confident in your vision but be willing to constantly tweak your plans to meet your vision. I also learned you have to learn to be comfortable being uncomfortable all the time. You are never going to have all the answers and you need to be able to strongly pitch your vision knowing this and knowing you have faith you will figure out how to solve the issues that come up.

Q. What impact has the Entrepreneurship Program had on your career or life? 

A. It allowed me to meet some of my still closest friends who have a shared passion for success as well as allowing me to feel it was possible to successfully run my own company. It gave me the confidence to know that I can create my own vision for my own future. It was a challenging experience that required a lot of hard work and a lot of team work and pushed me beyond the limits I thought I had on my own career.

Fun Fact: “I ran the Boston Marathon in under four hours in 2014.

Q. What do you consider your biggest entrepreneurial success? 

A. The fact the company I started with my business partner six and a half years ago has been profitable every year we have been in business and candidly are still in business six and a half years later! So many companies fail in the first five years and the fact we are still here, I consider a success. We have not accomplished everything we want to accomplish yet but we feel we are in a much more stable position. That feeling of somewhat making it makes me feel successful. The fact I feel like I will never work for someone else again or need to update my personal resume feels like a big success. Regardless of how successful an entrepreneur is financially, if you are working for yourself truly, there is a feeling of success that is difficult to describe.

Q. What advice would you give to aspiring entrepreneurs? 

A. Realize that just because you fail does not make you a failure. You will fail multiple times striving to be an entrepreneur. The more you fail, the better your chances of success are. So many can get wrapped up about presenting perfect images of themselves online or to their friends and family that they are afraid to fail. To be honest, no one really cares if you fail or not, as most people are worrying about themselves. That is one of the great ironies in life. People care a lot less about your successes than you think they do. So work as if failure is simply a learning experience to get better. It's all a part of your journey. Also remember that being an entrepreneur is taking the hard, long road. It is not the easy road. But in the end, it can carry much less risk because if you can make it, you are never going to fire yourself. There is a ton of risk working for other people. If you can make it as an entrepreneur, the risks are significantly less in many ways long-term.