• Startup Veteran™
  • Posts
  • How This Naval Aviator Soared To Business Success And Built A Multi-Million Dollar Investment Empire

How This Naval Aviator Soared To Business Success And Built A Multi-Million Dollar Investment Empire

John Rubino, Navy Veteran & Founder of JID Investments

Tell us about you and your military background:

My name is John Rubino and together with my wife Stacie and four children (Lauren 19, Jack 17, Andrew 15, Charles 13) live in Burke, Virginia, about 25 minutes outside of Washington DC.

I am originally from Brooklyn, New York and attended college at the New York Maritime College in the Bronx, New York where I received a Bachelor of Science in Business Administration, a 3rd-Mates License in the Merchant Marine, and a direct commission to the United States Navy. I honorably served for 20 years as a naval officer and aviator, retiring in June 2017 from active-duty service. My operational aircraft was the mighty P-3 Orion, and I retired as a Lieutenant Commander (O4). I also received a Master of Science in Aviation/Aeronautical Science from Embry Riddle Aeronautical University in 2008.

I spent most of my time in the service on the East Coast with tours to Jacksonville FL, Patuxent River MD, and Northern Virginia. I deployed twice to Puerto Rico/Keflavik, Iceland and Sigonella, Italy, respectively. I also served a three-year tour overseas in Naples Italy on the Commander Naval Forces Europe/Commander 6th Fleet staff as a Senior Operational Analysis, Deputy Director and a three-year tour as an instructor pilot and department head at Training Squadron-Twenty-Seven in Corpus Christi, Texas. My family and I arrived at Burke back in 2011 when I was stationed at the Navy headquarters staff (OPNAV N1) in Arlington, Virginia where I served two tours and finished my career.

My 20 years of service was a truly rewarding experience as I had the opportunity to lead, work with, and be responsible for some of the most amazing and dedicated people in our nation. I learned how to be a leader and what it meant to work together as a team. Some of the greatest skills I attained during my time in the service included communication, leadership, integrity, and personal responsibility. I was also blessed to have several mentors who pushed me to be my best through both personal and professional development.

Tell us about your business:

I started investing in real estate back in mid-2005. I purchased land on two separate opportunities and had new construction single family homes built on the lots. After deciding to continue with my Navy career, my family and I moved overseas to Naples, Italy but I continued to invest passively with some close friends. During this time, I was earning a strong return on my capital as well as learning a great amount of information on the passive real estate investment model. After my tour to Corpus Christi TX, I moved back to Northern Virginia in 2011 where I was stationed with the Navy headquarters staff.

In 2012, I decided I wanted to stand up my business and center it around investing passively in real estate, with my friends, colleagues, and other active investors who needed private equity capital. Together with my CPA at the time, who is now my business partner and our Company CFO, we formed JID investments LLC (JIDI) in April 2013. Our Company has offices in Hilton Head SC and Fairfax Virginia.

JIDI is a passive real estate investment and private equity firm that secures high yield returns by providing investment capital to residential, mixed-use, and commercial real estate sponsors, developers and businesses having viable real estate, business, and/or investment opportunities. Our mission is to form long-lasting business relationships with both developing and established companies. By doing so we ensure strong partnerships and become an integral part of their financial success. We do this by funding sponsors, developers and business ventures while earning our desired returns; continuously growing and developing our business relationships and expanding our investor base (currently 250 accredited investors) and capital for future projects.

JIDI focuses on the Mid-Atlantic region, Washington DC markets, and southeast regions for our investments offering housing to luxury, market-rate, and affordable residents. We look to partner with active investors for project investment and high net worth/high income earning accredited investors.

Describe how you got the business started:

The idea of the Company started in 2011 and we spent a year between 2012 and 2013 to formulate the business into full operations. Our costs were small (less than $2,000) to start up the Company and focused primarily on LLC formation, business emails, website, business cards, etc. Our first set of investments ranged from $25,000 – $50,000 per investor, per project and we started with four total investors in the business.

Following our third project we started raising larger sums of investment capital and began a concerted effort to invite more accredited investors to participate with us on our projects. Friends and family were our core set of investors but as we grew and were investing in more projects, we started focusing on public accredited investors who found us on our website, social media sites, and through in-person networking opportunities. We also began to consult with real estate and private placement attorneys to ensure we were following compliance laws with raising funds through private placement.

Our concept was unique as we raised/raise a select amount of money for investments with our active sponsor partners. This ranged/ranges from $1,000,000 - $5,000,000 a project on a deal-by-deal basis (also known as a Single-Purpose Vehicle or SPV). Our research on these parameters revealed we were perfectly suited since larger, institutional companies were raising over $10,000,000 on placement of their funds, and smaller individuals were raising between $50,000 - $250,000 for individual investment. We also discovered our sponsor partners were highly receptive to working with one group who could raise that targeted level of capital from individual investors, so they didn’t have to manage the communications or administrative necessities of each individual investor.

Tell us why you wanted to become an entrepreneur:

My family had several business owners who really enjoyed the interactions with their customers as well as leading their Company. My dad owned his own construction business in New York and always had great stories about his Company. These were some of the key contributors to why I decided to start my own business.

As I got closer to retirement, I spent a good amount of time considering whether I would operate JIDI part-time and go to work for the government as a civil servant or contractor. I also explored corporate, non-profit, and private industry careers as well. However, I knew if I gave my business 100% of my time and effort that I could grow it into something special. I had already had the Company operating for about four years at this point, working part-time and had decided to focus solely on the business as my second career. Not collecting a paycheck every two weeks did take a little getting used to, but having the freedom to choose my tasks, meetings, and schedule on a daily basis is extremely satisfying. I also enjoy meeting in person with clients, investors, and colleagues to discuss business. I learn a ton during each engagement which continues to grow my personal and professional development

One of my closest friends and fellow Navy veteran is one of our closest and largest partners. He’s owned and operated his Company for twelve years now and has completed over $400M in development across forty real estate projects. I also have several other veteran friends and colleagues who are entrepreneurs and business owners who love what they are doing.

Describe how your military background prepared you for entrepreneurship:

Being in the military for 20 years was also an amazing experience as I learned about leadership, teamwork, communication skills, and personal accountability. These efforts all drove me to want to be a business owner and entrepreneur. I also learned about real estate investing at the midpoint of my Navy career which allowed me to leverage my education, experience, and investment diversification in an industry that I now truly love.

As a leader in several positions inside the Navy, I learned how to best lead and manage from my senior enlisted, peers, and superiors. Mentors were key, especially when starting at a new duty station or job. Having mentors is key to success in business and in life. It also allows us to practice humility and acknowledge we always have more to learn from our experiences, lessons learned, and those who are willing to teach us. During my military career I was also able to acquire skills as a financial, budgetary, and research analyst which has helped me immensely as both a business owner and real estate investor.

My biggest obstacles and challenges focused mainly on whether I had the right expertise and skill sets around me to start a business. I knew I had to have trusted people as part of the team to get the Company up and running, share my vision, have support with suggestions and ideas to build a foundation and grow, and be contributing and valued team members for the long-term. I also had to be sure I wasn’t creating a situation where I would be overwhelmed with my Navy job, this new business, being a dedicated husband and father for my family, and those other things I enjoyed doing in my free time.

I spoke to and met with several friends, mentors, family, and close associates to go through my business plan including, how I would go about putting the business together, defining the problem we would solve, and how we would bring value to those we serviced. These folks provided fantastic insights and reassured me that I would be highly successful given my values, skill sets, and passions. Many of them are also investors in our Company which speaks to their confidence, trust, and support for our business.

One major move was bringing in my accountant at the time who is now my business partner, our Company CFO, and best friend. He brings 30+ years of business experience and as a federally licensed enrolled agent handles all of the finances for our Company to include taxes for the Company and our investors. This has made our Company hugely successful and allows me to focus on the duties and responsibilities of the Company that I am best at addressing.

Our business services several markets and locations. We primarily invest in the Mid-Atlantic, Washington DC metropolitan and surrounding markets, and Southeast. We know these markets really well and have several active sponsor partners developing, building, managing, and operating a wide variety of real estate projects.

As a business owner and entrepreneur having a business degree is important, but my experiences gained through military service were a key component to my success.

Describe how you’re doing today and what the future looks like:

Since our inception we have invested in 30 real estate projects and raised close to $40M from 250 private investors. We have completed 18 of the 30 projects earning our investors a 12-20% per year return on those completed projects. Our current portfolio of 12 active projects includes development and new construction of multifamily housing, existing and new construction mixed-use residential housing and commercial retail, Opportunity Zone investment, and land development. In total we have over $27.6M invested and are projecting over $33M in profits.

JIDI has a small team of two full-time employees with outsourced consultants that assist us with both investor and project relations.

Our top goals for the remainder of 2023 and into 2024 is to focus on our existing portfolio of projects, working with both our existing investors and welcoming on new investors who are interested in participating on our projects, identifying new active sponsors for partnership, and growing our team with people who love what we do, add value and grow, and make a difference.

About two years ago JIDI brought on the Juniper Square investor portal. This resource has been quite a gamechanger for our Company. It has simplified several tasks and processes to make us a more efficient and effective Company. Juniper Square has a built-in Customer Relations Management (CRM) tool which allows for seamless communication and information sharing. The information management tool allows us to securely retain and store key documents (i.e., tax paperwork, project specific documents, and sensitive information). Investors can login with their discrete username and password to view their currently executing investments as well as completed investments. Juniper Square also allows us to deliver investor reports and statements with the click of a few buttons.

Our website provides fantastic information on the Company, team, current and completed projects, funding and investor services, and media releases/blogs. JIDI is also active on social media. We have close to 1200 members on our LinkedIn page and over 400 on Facebook. JIDI has also been featured on over 40 podcasts and is a frequent guest on webinars and mastermind groups.

My vision for JIDI is the same now as it was over 10 years ago; provide family, friends, and colleagues solid real estate investment opportunities that make sense, offer strong returns, and doing so through hard work, dedication, and having fun. I wake up each day with this as my top priority and always go to work (if you want to call it that) with a smile on my face. To me, the relationships I grow, friendships I make, and people I meet, learn from, and work with is the ultimate blessing.

Share some advice with your fellow veteran entrepreneurs:

We always tell ourselves, “If I only knew 20 years ago what I know now…” My take on this is I would have worked harder to get the education sooner, read more topic related books, listen to more webinars and podcasts, buy 5-10 active properties for long-term hold, and capitalize on cash flow with appreciation sooner in my career. Easier said than done. My plan on this is to teach my kids so they can leverage their greatest resource, time.

Regarding education, there are many fantastic books, news outlets, podcasts, webinars, and even templates/checklists to help you start your real estate investing career and/or owning your own business. If you were to serve 20-30 years in the military, have a government pension, and maybe work part-time, you can easily be a passive real estate investor or even take the plunge to buy, rent, or flip.

If you know the location where you’ll be when you leave the military, and better yet can serve your twilight tour at that location, start networking right away. Meet industry professionals and leaders as soon as possible. Get your name out there and look for networking groups and community events where you can socialize and talk with those who can help advance your vision.

Planning is very important when starting out as a new business owner and/or entrepreneur. Lots of moving parts. As I said earlier, having the right people and resources as employees, consultants, and/or outsourced support is key. Looking at your startup costs and how to raise those funds is also very important. Finally, you have to be able to define the problem and how your business offers the solution. Simon Sinek calls it your “why.” It’s what makes you, you. If you’re not sure or are having trouble getting started, talk to family members who are business owners, and you can also reach out to me.

My last point of advice is to have a strong foundation, whether it’s prayer and faith, your family, exercise, or something that drives you. Start each day focusing on and growing that foundation. I spend every morning in prayer before I start my day. That sets the pace and priorities of my day. At 5PM, my workday is over, and it is time to spend time with my family. Always be willing to learn more. Humility is extremely important and remember that this is a team sport. My favorite books to share are Rich Dad, Poor Dad, How to Win Friends and Influence People, and the Millionaire Next Door. I am currently reading The Intelligent Investor (by Benjamin Graham), I Will Teach You to Be Rich (by Ramit Sethi), and the good book, the Bible (written by God).

Where can we go to learn more: