Jonny Weiss was born in New York City, and raised in Greenwich, CT. From an early age, he excelled in multiple sports, ultimately focusing his exceptional athletic talents on baseball. In high school he was sought after by several Division I college baseball programs, and initially selected Boston College, before transferring to Tulane after his Freshman year, and eventually finishing his studies at Cornell University. While at Tulane, he was named to the Conference USA Commissioner’s Honor Roll, voted first team All-Conference USA, and was a member of the Tulane 3.0 Club for scholar-athletes.

After graduating with a Bachelor of Arts degree in psychology, Jonny Weiss of Greenwich, CT explored multiple professional fields of interest, including finance, sports management, health and fitness, and medicine. Eventually, his aptitudes and interests led him to the real estate investment field, where he spent five years excelling in various roles at RedSky Capital, LLC.

In 2019, Jonny Weiss elevated his career by earning a Master’s Degree in Real Estate, Finance and Investment from New York University, which is one of the best real estate programs in the country. Currently, he is a licenced real estate salesperson in New York and Connecticut, and is pursuing real estate investment and consulting opportunities across the U.S.

What inspired you to enter the real estate investment field?

To start with, I love design and architecture and enjoy envisioning and creating spaces that are both functional and elegant. In addition, real estate is something tangible, and the industry is structured, stable, and built on solid, proven fundamentals. Unlike some industries that overheat and then crash, the real estate industry drives nearly half of the GDP in the country. It supports millions of jobs directly and indirectly. Regardless of what happens in the economy or which trends dominate, people are always going to need places to live and work. Also, real estate is an excellent and proven way for individuals and families to create long term generational wealth by taking advantage of the various tax benefits and inflation protection the asset class offers. Having a healthy appetite for risk is vital for success in this industry. It is a high risk, high reward proposition, and that is appealing to me at my age. No two deals — or even two days — are ever alike. I find this very energizing and exciting.

What advice on making money do you have for real estate professionals who are just starting their career?

Generally, I would advise those new to the real estate investment world  to start with a relatively small property that has stable in-place cash flow and minimal downside due to leasing or construction risk. In some cases, they will need to invest additional capital to add value and/or increase rental rates. Also, in most commercial real estate investment properties, investors can pass along certain expenses to tenants, such as utilities and property taxes, which helps keep landlord costs down and ultimately boost net operating income.

And the last thing I would say to those new to the industry, or who are thinking about entering, is that they do not have to worry about managing their own property if that is a dealbreaker. This can be quite stressful and costly for those without infrastructure in place to do this in an efficient and cost-effective way. Instead, they can engage a property management company who, for a fee, will take ownership of all landlord responsibilities.

When you were starting out, was there ever a time you doubted it would work? If so, how did you handle that?

I would still consider myself relatively early in my real estate career and will admit that some days are filled with apprehension and uncertainty when contemplating my career goals, but I realize this is the reality in any entrepreneurial endeavor. However, I soon realized that my doubts were not rooted in what was happening in the industry itself — they were based on my fears and anxieties about making mistakes. I came to the conclusion that, ironically, being terrified of making mistakes is in itself an enormous mistake, and that the only way forward is to be bold and be willing to take risks.

What is one marketing strategy (other than referrals) that you’re using that works really well to generate new business?

My website at generates a great deal of traffic. I regularly publish thought leadership articles on various industry topics, such as what the Biden Administration means for real estate investing, the impact of COVID-19 on real estate investing, what to look for in a real estate professional, and more. I also regularly publish videos, which seem to be popular, and I am receiving extremely positive feedback on them.

What are some of the toughest obstacles that you have overcome in your life?

Growing up, my father was my role model. He passed away about 12 years ago, around the time I was graduating with a Bachelor of Arts degree in psychology. It has been difficult not having him around as a mentor, but he is always in my heart and remains my role model. My grandfather also passed away around that time, which made things even more challenging.

However, rather than focusing on these obstacles and wishing things were otherwise, I realize now that they have made me incredibly resilient and strong. This is definitely helping me in my personal and professional life. I feel that I can tackle anything that comes my way. My mindset is very success-oriented and I try to  focus on solutions, rather than dwell on problems.

What do you think it is that makes you successful?

I have very strong interpersonal skills. I am direct, honest and to the point when it comes to business. I don’t like fluff — either on the giving or receiving end. I also have a great deal of empathy, and can reflect on the various ways that people see things. When I want to achieve a goal, I do what is necessary to get it done. I expect to succeed.

What does the future hold for your industry? What are you most excited about?

There are several things that excite me, such as the re-invention of retail on a post COVID-19 landscape. And speaking of COVID-19, for about the last decade office space has been getting smaller as organizations sought to minimize their commercial occupancy costs, which in some markets can be extremely high. However, given that social distancing is going to be part of our world for at least the next year or two — and some experts say it could be four or five years — we are going to see a dramatic reversal of this trend, with more square footage per worker, and more distinct workspaces.

Also, I expect that the work-from-home trend — which started well before COVID-19, but has been vastly accelerated by the pandemic — will continue for the foreseeable future. This will not make office space obsolete, but instead will change design and purpose. For example, instead of conventional workspaces, we are likely to see more open spaces where workers drop-in for an hour or a day, depending on their needs. We are also likely to see multiple organizations establish partnerships for a specific space. For example, organization A’s people have access to it on Mondays, while organization B’s people have access to it on Tuesdays, and so on.

What business books have inspired you?

There are several business books that have inspired me, but the one that stands out above all others is The One Minute Manager. I am close friends with the author Ken Blanchard. I have read Ken’s book several times, and each time I learn something new and insightful about various aspects of being a great manager. One of the most powerful lessons is that great leaders need to be extremely fair-minded. It is not like the old days when leaders were at the top of a hierarchy, and everyone else was lower. These days, leaders need to be on the same level with their team, and empower rather than intimidate them.

What advice would you give to your younger self?

I would tell my younger self to enjoy the journey of life and never take tomorrow — or even the next minute — for granted. Sometimes, we can get so consumed and obsessed by the future that we sacrifice the present. The best way to center and ground oneself in the now is by being grateful. Yes, we all face challenges, but it is essential to be thankful. I believe that an attitude of gratitude is the key to a successful, happy, and well-lived life.

And while I am giving my younger self some advice, I would also say: take more risks! Yes, there will be scenarios when plans are less than successful, and other times they will fail. What matters most is that we learn from our mistakes and we avoid making the same mistake twice.

Are you willing to be a mentor? If so, how should someone contact you?

Yes, absolutely. I can be contacted through my website at or LinkedIn



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