Jesse Prince of HappyNest: 5 Things You Need to Create a Highly Successful Career in the Commercial Real Estate Industry Today

Yitzi Weiner
Authority Magazine
Published in
13 min readOct 27, 2023


Grit and Determination: Success in commercial real estate is all about perseverance. While instant wins can be thrilling, the essence of the game is in playing the long-term strategy. Continuously showcasing your expertise, even if it means offering pro bono services initially, can pave the way for bigger opportunities and referrals. For instance, in my early days, I would run numbers for clients for free, which eventually led to listings and investment opportunities. Remember, every interaction is an opportunity to showcase your worth.

The commercial real estate industry is a dynamic and challenging landscape that offers enormous potential for success. However, it requires a unique blend of skills, knowledge, and aptitude to truly excel. How does one establish themselves in such a competitive field? What does it take to consistently rise to the top in commercial real estate? How does one rise above the headwinds that are challenging the commercial real estate industry today?

In this interview series, we’re seeking to learn from the experiences of those who’ve successfully navigated these challenges. We’re interested in interviewing commercial real estate professionals, brokers, investors, leaders of Real Estate Firms and Real Estate Investment Trusts (REITs), as well as anyone who’s found significant success in this industry.

As part of this series, we had the pleasure of interviewing Jesse Prince.

Jesse Prince is the founder and CEO of the commercial real estate investing platform, HappyNest. He is a West Point Military Academy graduate and combat veteran who is passionate about upholding the American dream to make real estate investing accessible for everyone. He launched HappyNest in 2017 to empower investors of any budget level to do what he does: make money by investing in real estate.

Thank you so much for joining us in this interview series! Before we dive in, our readers would like to learn a bit about your origin story. Can you share with us a bit about your childhood and how you grew up?

I had a pretty vibrant childhood — I was born in New York and grew up with three brothers. I was heavily involved in sports and was always exposed to new experiences — for which I am thankful to my parents.

Our family has two main principles: “Never live outside of your means” and “Always do good things.” The last principle in particular made a lasting impression on me as a child. I was always eager to help people around me.

My oldest brother Todd, with whom I was especially close, passed away in a car accident when I was 13. I was divested. The person that I looked up to was suddenly gone. I wanted to honor his legacy and follow his steps, so I set out to complete what he had started. He was a freshman at the United States Military Academy, West Point and so I dedicated myself to joining the academy and serving the military. I graduated in 2004 and had two tours of active duty in Iraq. I became a Captain and had 120 soldiers under my command. I’m proud to say that I brought all of them back.

Can you share with us the ‘backstory” of how you decided to pursue a career in commercial real estate?

I learned valuable lessons in the military but after transitioning back to civilian life, I realized I had no idea how to manage my money, grow wealth and save for retirement. I struggled to land a job and slowly depleted all my savings in search of a new purpose outside of the military.

After leaving the Army, I tried for a job at a big financial company as a wealth manager. They had me take a personality test, and afterward, they told me I “wasn’t a self-starter” and didn’t give me a second interview. This was funny to me because just a few months before, I was in command of 120 soldiers and handling millions of dollars of equipment on my own patrol base in the middle of nowhere in Iraq. That moment really lit a fire in me to prove them wrong.

Since the traditional bank job didn’t work out, I began to look elsewhere. I witnessed first-hand, friends of mine who had experienced significant success professionally and financially in the industry, but more importantly, I found real estate finance fascinating. My first step was to get a master’s degree in real estate finance while also working in the sector. From there, I was lucky to meet many incredible people who guided me and helped me envision and ideate HappyNest.

Can you tell our readers about the most interesting projects you are working on now?

Currently, our primary focus is on democratizing access to alternative investments. We’re on a mission to help our customers build a diversified portfolio in this sector, offering them exposure to assets typically reserved for the wealthiest investors. By diversifying within alternative investments, we aim to maximize potential returns while distributing risk across various industries.

Another initiative close to my heart is our outreach to the military community, encompassing active-duty personnel, veterans, and their families. Recognizing the financial and emotional challenges of transitioning from military to civilian life, we’re driven by a commitment to service and financial well-being. I’ve personally faced these challenges after my time in the Army, and it’s my goal to ease this journey for others. Financial stability plays a pivotal role in overall well-being, and we’re dedicated to providing the tools and resources to ensure a smoother transition for our servicemen and women.

In line with this, we’re excited to offer a $25 incentive for every military member, veteran, or their immediate family member who joins HappyNest. It’s our way of appreciating their service and helping them embark on a promising financial journey.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful for who helped get you to where you are? Can you share a story about that?

While I’m deeply thankful to my family, friends, and especially my wife, Jackie, for their unwavering support in my endeavors, one person stands out from my time in the Army. Command Sergeant Major Michael Williams (Ret.) may have technically reported to me, but in reality, he was my mentor. He was pivotal in shaping my character and work ethic. Mike taught me the value of self-discipline, fostering team spirit, and the importance of taking ownership of my actions. He believed that while certain things are beyond our control, self-reflection and accountability can pave the way for personal growth. Instead of placing blame elsewhere, he taught me to see failure as a chance to learn and grow. I’m forever grateful to Mike for these invaluable life lessons.

As with any career path, the commercial real estate industry comes with its own set of challenges. Could you elaborate on some of the significant challenges you faced in your career and how you managed to overcome them?

The commercial real estate industry is a mixed game of who you know and what you know. Getting a foot in the door is all about who you know, so networking is super important. But getting ahead is about what you know, so educating yourself is critical to success. My number one piece of advice comes from my days in the Army — speak the language of your profession. Words mean things, and it’s important that you get smart on how to view investments from both a macro and micro viewpoint. There is a treasure trove of free and paid information out there to help you get where you need to be. Read, listen, attend conferences, and be open to learning and you will ultimately set yourself apart from the crowd.

When I first started in the industry, I wasted my sales time communicating with the wrong type of leads. Focusing your sales strategy and becoming an expert in one unique aspect of the industry will set you apart from your peers and keep your name top of mind when a specific scenario arises that requires your expertise. For example, specializing in sale-leasebacks or zero-cashflow properties makes you a valuable player on any team and will help build the network of people who’ll refer clients in need.

Ok, let’s now move to the main part of our interview about commercial real estate. What are the 3 things that most excite you about the industry now? Why?

Real estate is known to deliver value to investors as a non-correlated asset, especially during periods of heightened inflation. In the past seven inflationary periods, CRE outperformed six of those. Moreover, this asset class outperformed bonds during six of those periods making CRE investing exceptionally useful during times like these. While right now the macroeconomic conditions are uniquely different there are actions that many can take to create value.

While high interest rates and office vacancies should be worrying, those can lead to exciting opportunities for individuals seeking to invest in CRE. These elevated interest rates could potentially lead to properties across the states becoming available at significant discounts. For example, a number of companies are considering relocating their headquarters to smaller states to reduce costs. This unique “migration” could drive up property values in smaller cities while simultaneously creating newer opportunities in the locations that were left behind.

Keeping the above in mind, real estate investment trusts (REITs) can be a great diversifier for investors looking to explore undervalued commercial properties. These focus on long-term wealth building, and everyone can tap into REITs without directly being responsible for property management.

What are the 3 things that concern you about it? Why? What should be done to address and alleviate those concerns?

The current landscape of CRE is indeed unparalleled. While the sector presents numerous opportunities, it’s not without its challenges. My top three concerns are:

  1. Office Vacancy Rates: The surge in vacant office spaces, especially in cities like New York, is alarming. A significant drop in office visitation rates in the first quarter of this year emphasizes the need for action.
  2. High Interest Rates and Loan Distress: The Federal Reserve’s current hawkish stance, combined with economic uncertainties, could lead to landlords facing difficulties in debt servicing. Notably, J.P. Morgan has forecasted a potential default on nearly $39 billion in CMBS office loans.
  3. Potential Economic Impact: The cumulative effect of these issues could not only shake the CRE industry but also ripple through the US economy, possibly leading to financial instability reminiscent of the 2008 recession.

To address these concerns:

  • Consider Loan Extensions and Favorable Work-Outs: Banks could consider extending loans in a manner similar to student loan accommodations. This could help mitigate fears in secondary markets. It’s crucial to note that another financial crisis akin to 2007–2008 would be detrimental for all stakeholders, especially banks
  • Government Initiatives: Implementing programs to boost economic activity in central business districts could invigorate our major cities. Encouraging a return to office environments can rejuvenate our cultural hubs.
  • Streamlining Development: Cutting down on bureaucratic delays for developments, especially those aimed at housing solutions or repurposing underutilized spaces, can instill a renewed sense of community pride.

I believe that by addressing these concerns collectively we can pave the way for a more resilient and vibrant CRE sector.

If you had the power to put in place 3 changes to improve or reform the industry, what would you suggest? Please share stories or examples, if possible.

There are solutions we can implement to heal the sector and maintain the balance between remote and in-office work. Firstly, we should begin implementing tax penalties on large companies to mitigate the risk of default in the commercial real estate industry. This would encompass companies with more than 15,000 employees that exceed a 20% remote workforce threshold. This penalty would be calculated based on the average annual cost of office rent for a Fortune 5000 company and the cost savings from reduced office footprints due to remote/hybrid workforces. This would motivate companies to focus more on hiring local talent, in turn, incentivizing businesses to lease more office space.

We could also consider implementing tax incentives aimed at creating a balance between remote and in-office work by prioritizing individual workers and communities. In essence, this would encourage individuals to work in person without punishing those who need to work remotely. There are many ways that we can approach this, including tax deductions for individuals’ commuting expenses or tax credits for work attire, which would motivate more people to return to the office and in turn would reignite the market.

For a young person who would like to eventually make a career in commercial real estate, which skills and subjects do they need to learn?

For any young individual aspiring to build a career in commercial real estate, it’s crucial to master real estate finance, ensuring a solid grasp of the numbers. Understand that at its core, commercial real estate is driven by data and analytics. Familiarizing oneself with industry jargon and terms is essential, as effective communication plays a pivotal role in the industry. Dive deep into the basics of real estate, as this foundational knowledge will set the tone for your career. Always remember that commercial real estate decisions are not driven by emotions but by facts, figures, and feasibility. It’s vital to approach underwriting conservatively, ensuring projections are realistic. Lastly, always strive to provide value. The more you can offer to your team or clients, the more opportunities will present themselves as your career progresses.

Ok, here is the main question of our interview. Can you please share the “Five Things You Need To Create A Highly Successful Career In The Commercial Real Estate Industry”?

Here are the five things I believe you need to keep in mind to create a highly successful career in the commercial real estate industry:

1. Grit and Determination: Success in commercial real estate is all about perseverance. While instant wins can be thrilling, the essence of the game is in playing the long-term strategy. Continuously showcasing your expertise, even if it means offering pro bono services initially, can pave the way for bigger opportunities and referrals. For instance, in my early days, I would run numbers for clients for free, which eventually led to listings and investment opportunities. Remember, every interaction is an opportunity to showcase your worth.

2. Resilience: Not everyone you meet will be as nice and understanding as you wish they were. Rejection is part of the journey. Surround yourself with individuals who believe in you and understand your journey. In the commercial real estate world, there are experienced professionals who were born into the game, and those who once started from scratch. There are great people in both of those groups who value the essence of giving someone a chance. Seek them out, learn from them, and let them mentor you.

3. Foresight and Vision: Success isn’t found in chasing after every trend but in understanding the underlying patterns of the market. Rather than trying to predict short-term market behaviors, focus on the big picture and identify patterns that indicate where the market is headed in the next decade or two. Remember, true vision often lies in sticking to fundamentals and not getting swayed by temporary fads.

4. Creativity: The ability to see potential where others see gloom and doom can set you apart. Take, for example, the decline of the mall industry. While many declared it dead, some visionary minds saw an opportunity in these vast spaces. They transformed these malls by introducing unique experiential attractions, driving foot traffic, supporting tenants, and ultimately creating value. See past what is and create value where none seemingly exists. An open mind to change and an avoidance of noise will make you invaluable.

5. Disciplined Work Ethic: Speaking the language of your profession and consistent work effort are non-negotiable. While many in the industry might take shortcuts or overstate their achievements, it’s imperative to remain authentic. Dedicating yourself to getting better every day, even in seemingly insignificant tasks, will compound over time. Whether it’s reading up on industry trends while others are watching TV or consistently showing up when others don’t, these efforts will make all the difference. Success is built brick by brick, day by day. It might not always feel like you’re making progress, but over time, those small efforts accumulate and result in big wins.

What do you believe makes your commercial real estate company distinctive? Could you share an anecdote about that?

Before founding HappyNest, I noticed that real estate investing platforms catered primarily to institutional investors and wealthy individuals, often leaving out many who aren’t able to meet significant initial investments.

I thought the sector seemed very unfriendly to newcomers, who want to build wealth and learn about the industry. There needs to be a platform that doesn’t alienate so many people. That’s when I decided to create a platform that provides an opportunity for everyday Americans to improve their financial literacy around real estate investing while also granting access to exciting commercial real estate properties to build wealth regardless of their financial backgrounds.

To democratize access to investing in this asset class traditionally reserved for the wealthy, one of HappyNest’s features is a $10 entry-level minimum.

In addition, the unique “Loose-Change round-up” feature allows automatic investment of spare change enabling users to gradually increase their savings and grow their real estate portfolios.

What is your favorite “Life Lesson Quote”? Can you share a story of how that had relevance to your own life?

“Why do we fall sir? So that we can learn to pick ourselves up.” -Alfred Pennywise, Batman Begins

I think my personal story of trials and tribulations speaks exactly to this quote. Failure is a stepping stone to success and if you don’t treat it as such you are bound to stay exactly where you are.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

Commercial real estate is the third largest asset class after fixed income and equities and a great portfolio diversifier. As I delved deeper into the sector, I was surprised to learn that it isn’t as accessible to everyone as it should be. Opportunities were purely available to the wealthiest class, alienating regular individuals.

My goal was (and still is) to democratize commercial real estate investing and close the wealth gap. Essentially making real estate investing as accessible as investing in stocks. Although at that time I may have lacked that “great influence” in commercial real estate, I was driven by the desire to “do something great.” I created a mobile platform to help everyone build their financial future — regardless of their financial status — by enabling easy access to high-quality commercial real estate assets while also improving their financial knowledge of the sector. And that’s how HappyNest came to life and I’m happy to say that every year we’re helping more people achieve their financial goals. As a fun fact, when I envisioned HappyNest, I had only $10 in my bank account, which I made sure would be the minimum required deposit on our app. This feature alone encouraged a lot of people to begin crafting their financial future and building wealth.

How can our readers further follow your work online?

This was very inspiring. Thank you so much for joining us!



Yitzi Weiner
Authority Magazine

A “Positive” Influencer, Founder & Editor of Authority Magazine, CEO of Thought Leader Incubator