We caught up with the brilliant and insightful Harry DiOrio a few weeks ago and have shared our conversation below.
Harry, looking forward to hearing all of your stories today. We’ve love to hear an interesting investment story – what was one of the best or worst investments you’ve made? (Note, these responses are only intended as entertainment and shouldn’t be construed as investment advice)
The best AND worst investment I ever made was the first multifamily home I purchased in 1989 up in Syracuse. I was living in Syracuse and was going for full custody of my 5-year-old son. I bought this two family home for $75,000 with about a 5% down payment. It worked out great for a place for us to live and the income from the rental unit and the depreciation of the asset made it very affordable.
I subsequently bought and moved into another two family in a better school district and rented both units the Syracuse house and it produced a positive cash flow. When I moved to NYC in 2003, I sold my investment properties in upstate NY and after 14 years of ownership, the Syracuse home sold for only $79,000.
I remember when I purchased the home in 1989 a friend of mine was buying a 1BR apartment in NYC also for $75,000. I thought: Who would pay $75k for a 1BR? But when he sold the place in the early 2000’s, it went for $500,000! Lesson learned: Location, Location, Location!

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers
I was living in Syracuse and working as at a newspaper as a Director of Photography and Assistant Managing Editor. I reconnected with an old girlfriend, who is now my wife, and she was living in NYC. My son was finishing up high school and I decided to move to Manhattan. I applied for jobs in media and found that I would make about the same amount of money as I was making in Syracuse, but the cost of living was much higher in NYC.
So, I decided to explore other opportunities. I figured I had an MBA and I could do something else. I made what I called a “selfish list” of the things I liked – cars, boats, planes, food, wine, real estate, and a few others – and then I went through the old-school NY Times classified section on Sundays. The real estate opportunities sounded exciting and would allow me to continue to shoot photos while I built by residential real estate business. As time went on, the more properties I sold, the fewer assignments I photographed until I switched 100% to real estate in 2009.
My photo skills helped me differentiate myself from other agents back before shooting interiors became much easier and everybody could get good quality images for a reasonable price. Also, the social skills I developed while photographing celebrities, musicians, politicians, and successful business people made it easy for me to interact with the buyers and sellers of luxury real estate in New York City.
Moving to the city also helped me reconnect with my old friends from high school and college and my passion for sailing after we purchased a summer home on Shelter Island and became members of the Shelter Island Yacht club where I grew up racing sailboats. My wife and I sail together on two different boats that we race throughout the season.
I feel lucky to have made the switch to real estate and proud of the business I’ve built. I’ve met some great people and have developed lifelong friendships with many of my clients. I’ve got a great team in NYC and have recently purchased a home in St Petersburg and expanded my business to the Tampa Bay area in Florida.

What’s worked well for you in terms of a source for new clients?
Most of my clients come from referrals. I provide a high level of service and my previous clients send me their friends and family. There are some families where I’ve represented the parents, and then their children and other family members when they’ve grown up and moved into their own homes.
Some of my clients have been with me through six or seven deals as their lives have changed. I’ve worked with clients to achieve their real estate needs through new jobs, relocation, marriage, childbirth, divorce, death of a spouse and their other ever changing personal situations.
A lot of people think that when they buy a home that they are going to keep it forever, and some do, but most people will sell that property in 5-10 years when something in their lives creates a need to move.

Any insights you can share with us about how you built up your social media presence?
I don’t consider myself a social media star, but recently I’ve begun to focus more on growing my brand online. I’ve found that people on social media are less interested in pure business posts and would rather see posts where they get a feeling for your passions and personality.
Each platform has a different audience and you need to tailor what you post accordingly. People on LinkedIn don’t want to see you playing with your dog, and people on Instagram and Facebook are less interested in business related posts. If you can find a way to blend your lifestyle with your business online, that’s the best formula for success.
I’ve had a lot of success with posting fun reels on Instagram and sharing them to Facebook.
Contact Info:
- Website: www.harrydiorio.com
- Instagram: harry.diorio
- Facebook: https://www.facebook.com/Harry.DiOrio/
- Linkedin: https://www.linkedin.com/in/harry-diorio-062b169/
- Youtube: @harrydiorio6334

