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Jonathan Weiss on Staying Motivated and Always Focusing on Your Goals

Jonathan Weiss was born in New York City, but his family moved to Greenwich, Connecticut when he was about nine years old.  He grew up playing sports.  He chose to play baseball mainly and was recruited heavily by several colleges across the country to play baseball for top baseball programs.  He played baseball for Boston […]

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Jonathan Weiss
Jonathan Weiss

Jonathan Weiss was born in New York City, but his family moved to Greenwich, Connecticut when he was about nine years old.  He grew up playing sports.  He chose to play baseball mainly and was recruited heavily by several colleges across the country to play baseball for top baseball programs.  He played baseball for Boston College his freshman year and Tulane after that for three years, and then he finished his studies at Cornell.  He studied psychology, but of course baseball was a big part of his life for a long time.  He had a bad injury during a game that took him out for a season and then led to more shoulder operations that brought an end to his baseball career. 

After college Jonathan spent some time trying to figure out what he wanted to do.  He thought he wanted to be a doctor.  At one point he worked for a hedge fund and also worked in fitness.  He did a little bit of everything to try to determine his real interest. 

He has been involved in real estate now for the past five years and it is the path he wants to pursue.  He left his last position at Red Sky Capital six months ago and he is nearing completion of a Master’s program in real estate finance.  He is looking for real estate investment opportunities and will be focusing on real estate full time after he completes his Master’s degree.

Why did you decide to create your own business?

My goal is to work for myself and have a more flexibility in my work.  I think it is the best way to have a good work/life balance.  I would enjoy the independence and being able to create my own schedule.  I have learned enough through my work experience, in school, and in doing my own due diligence on real estate markets that I feel it is a good time while I am young and since there will be several financial cycles that I will live through with the times to recover, so I am willing to take the risk for the additional upside of having my own business. 

I am being very opportunistic and looking at a little bit of everything in terms of real estate investments.  I do want to stay local at this time because of COVID and I am not traveling at this time, so I am learning the markets locally and looking at all kinds of different strategies, including full ground up development, a renovation project for a single family or a multifamily, and industrial deals in Connecticut.  My goal is to find some good investments in real estate in the next couple of months. 

The Master’s program at New York University (NYU) is also preparing me to work in real estate.  The whole program has moved online and that has been a challenge.  I cannot do the networking that I was planning to do, but the program is preparing me for what I want to do.  It is one of the best real estate programs in the country.   

What do you love most about the industry you are in?

I decided to focus on real estate because I really love architecture and design.  I like the physical attributes of it and physicality.  I like the fact that real estate is a tangible thing to invest in.  I feel like I have an understanding and control of the investment life cycle.  It is a stable industry.  I think it is an industry that approaches almost 50% of GDP in America, so it is critical to the country’s economy.  Real estate provides a lot of jobs and it not going anywhere.  People are always going to need to place to live and a place to work.  It is a great way to create generational wealth. 

What keeps you motivated?

My father passed away when I was just graduating from college.  I never really got to know him as an adult.  I think about him every day and want to make him proud, so he motivates me. 

My family in general motivates me.  Family is the most important thing to me. 

I am motivated to work towards financial success.  I am motivated by people I look up to.  In the sports world and in the real estate world, to see others that are so driven motivates me.  I have always been surrounded by competition, and competition motivates me for sure.  I have a very competitive drive, which helped me in sports, but now I want to take that competitive drive and put it into my career. 

Where do you get your inspiration from?

I am inspired by people and by seeing new parts of the world.  I enjoy traveling and seeing other cultures. 

Who has been a role model to you and why?

My father was a role model to me.  He was very successful.  He was so generous and so giving, and he treated everyone with such respect.  I do aspire to be the same way.  I like to do things that I think my father would be proud of.  I have some internal pressure about becoming a success.  Hopefully I can be selfless and make a positive impact on people’s lives like my father did. 

What traits do you possess that makes a successful leader?

I have work experience managing people.  I think about people from their perspective.  I have been on the other side of it because I have had the experience of working for a bad manager and there is nothing worse than that. 

I am close friends with Ken Blanchard who wrote The One Minute Manager.  I have read that a few times and it has definitely changed my perspective on management, including how to be a good manager, and how to motivate people, make them feel like they are doing a good job, and getting the most of them without being too hard on them.  You put yourself on their level and make sure they don’t think you are the boss that just tells them what to do and thinks you are better than them. 

What has been the hardest obstacle you’ve overcome?

After having several shoulder operations, I battled an addiction with opiates for a time.  That was definitely the hardest obstacle I have had to overcome, but I have recovered from that. 

I definitely feel there is nothing I cannot handle at this point because I feel like I have been through a lot at a relatively young age, having lost the career in baseball that I wanted and then having lost my father and grandfather within a short timeframe as well.  There have been a lot of difficulties that have made me a stronger person. 

What’s one piece of advice you would give to others?

Be mindful and stay in the moment.  Enjoy the journey.  Life is very fragile.  Through a lot of the experiences that I’ve had, I’ve realized how fragile life is.  I’ve also been guilty of projecting into the future and creating stress and anxiety for myself because I worried about what could happen in the future and anticipating negative things.  I had to really work on mindfulness and some meditation techniques to overcome that.  I am grateful for each day that I have, for being healthy, and for the friends and family that are in my life. 

Outside of work, what defines you as a person?

I am very personable.  I am genuine and down to earth.  I do not like confrontation.  I really enjoy being with friends and family.  I am a bit of a foodie and I really like to travel.  Fitness has always been very important to me.  I can be very competitive and driven about particular things. 

What trends in your industry excite you?

There is a trend towards net migration out of urban areas now, especially the big cities like New York City where it is very dense and there are so many people.  I think people are going to be working from home more, and that is going to change the dynamics of the office market, office leasing, and office rental rates and occupancy rates.  A lot is going to change in terms of how you design and fit out an office space.  There will be more demand for suburban office space that is flexible and creates an office for someone to go to on the days they are not working from home.  Office amenities and common areas have to be changed to comply with new guidelines and to keep everyone safe. 

Where do you see you and your company in 5 years?

In five years, I hope to have a stable portfolio of real estate assets and hopefully a few employees.  I would like to have several deals under my belt by that time and have created a successful track record with strong risk/return metrics.  I would also like the company to be scaled to the point where it is growing, and I will have more buying power.  I would like to be a noted player in the sector by that time with a solid reputation of successful investments. 

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