Jonathan Weiss on the Process of Becoming a Real Estate Investor and Always Staying Motivated

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 in 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.

Jonathan Weiss 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 become a real estate investor?

It is a way to make a big impact on the world. I like creating spaces for people to live and to work.

I also like the real estate industry because I also have an appetite for risk. As an entrepreneur, I need to be willing to take risks. You are taking your ideas and putting them out there. You are raising money. You have the full conviction that your ideas are good. It is a high risk/high reward perspective. You can put a ton of time and money into something that could just be zero, but you get excited because of the potential for the high reward and outsized returns and success makes it worth it. It is a real driver for me.

What trends in your industry excite you?

I am excited about the transformation of retail. It is not dying, but it is transforming. We need to come up with new creative ways to fill that space. It is exciting to think about what that will eventually turn into.

There has also been a trend in the past 10 years of office space getting smaller and smaller with less square footage per person. Now with COVID I think the trend is going to reverse, and it is going to go back to companies needing more space, more square footage per person, and more separated workspaces.

What is one thing you would change in your industry today if you could?

It has become so bureaucratic to conduct real estate transactions in New York. It can seem impossible to get anything done. Everything is so expensive. It takes a long time to get through to city agencies. It can take six months to get approval just to get a permit. This affects your timeline and makes your costs go up. It almost makes it not worth investing in that area at this point.

If you could change 1 thing you did in the beginning of your career what would it be?

I would have taken more risks early on and not be scared to make a mistake. I would have just dove in and learned from my mistakes instead of being scared to make them.

How do you maintain a work-life balance?

I value the time I have with my friends and family and taking care of my health. To me, these things are more important than work. I take pride in enjoying what I do so then it does not feel like work all the time. I make sure to prioritize my health, my relationships, and having a social life. Life is too short. Your best memories come from your relationships, not from work achievements.

What has been the hardest obstacle you’ve overcome?

The hardest thing I have had to overcome was losing my father. He passed away around the time that I graduated from college. It has been tough for me to not have him around in my adult years.

What is one piece of advice that you have never forgotten?

Don’t settle when you are looking for your partner in life. It is a big decision.

What does success look like for you?

I will be a success if I am remembered as a person that was giving my time and money. I would like to be a mentor for someone. I want to help others that are in a harder place than I am. I want to be as philanthropic as I can. I want to create a legacy for my family.

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