Jon DiPietra is a commercial real estate valuation executive whose career has been shaped by curiosity, discipline, and a willingness to take on complex challenges.
Born in New York City in 1975, Jon spent his early years in suburban New Jersey before moving to upstate New York. Those early moves taught him how to adapt and observe. He graduated from Shaker High School and later moved to Burlington, Vermont, where he studied accounting and finance while pursuing a brief but meaningful career in music. That mix of structure and creativity would stay with him.
In 1999, Jon returned to New York City to work as an equity trader. The experience gave him firsthand insight into markets and risk. Two years later, he made a pivotal shift into real estate valuation. Starting as a residential appraiser in 2001, he quickly found satisfaction in the problem-solving nature of the work.
By 2004, Jon moved into commercial appraisal, valuing apartment buildings, mixed-use properties, and increasingly complex assets. In 2007, he joined a major New York City firm and went on to appraise some of the city’s most recognizable properties, including the New York Times Building and multiple World Trade Center towers.
In 2018, Jon became a senior leader, managing a 40-person team producing thousands of appraisals each year. In 2024, he cofounded H&T Appraisal, where he now serves as Executive Vice President, helping build a growing national practice grounded in local expertise.
Outside of work, Jon values fitness, learning, and family. He believes discipline and curiosity are lifelong companions.
What is your typical day, and how do you make it productive?
My day starts early. I am up before most people and try to protect the first hour. I read industry news, review emails that matter, and think through the hardest problem I need to solve that day. I do not start with meetings. Productivity comes from deciding what actually deserves attention. Once the day fills up, that gets harder.
How do you bring ideas to life?
I write them down and quickly stress-test them. Most ideas sound good in your head. Fewer survive contact with real constraints like staffing, timelines, and clients. When we launched H&T Appraisal, the idea was simple. Build a national practice without losing local expertise. The execution was hard. We started with process maps and hiring profiles before we chased growth.
What’s one trend that excites you?
The renewed focus on quality over volume in professional services. After years of speed and scale, clients are asking deeper questions again. They want judgment, not just output. That plays to experience.
What is one habit that helps you be productive?
I review my work the next morning with fresh eyes. Even after twenty years, distance improves judgment. It catches mistakes and sharpens thinking.
What advice would you give your younger self?
Do not confuse intensity with effectiveness. Early in my career, especially when I was trading equities in NYC, I thought being busy meant being valuable. It does not. Clear thinking matters more.
Tell us something you believe almost nobody agrees with you on?
More data does not always lead to better decisions. In appraisal and in business, too much information can delay action. Good judgment comes from knowing what to ignore.
What is the one thing you repeatedly do and recommend everyone else do?
Walk the asset or the problem. I still walk properties, even flagship ones. You learn things you cannot see in a report.
When you feel overwhelmed or unfocused, what do you do?
I do something physical. Skiing, lifting, or even a hard walk. Motion resets my thinking. Sitting longer rarely helps.
What is one strategy that has helped you grow your business or advance in your career?
I said yes to complexity early. I took harder assignments before I felt fully ready. Mixed-use. Special-use. Flagship assets. That built trust and accelerated learning.
What is one failure in your career, how did you overcome it, and what lessons did you take away from it?
One failure in my career was assuming that staying in a role because I was succeeding at it was the same as growing. I led a large appraisal practice, managed a team of 40 professionals, and delivered strong results. On the surface, everything was working. Internally, I was not challenging myself in the ways that first drew me to the industry.
When that role ended, it was a hard moment, but it created space to reflect rather than react. I took time to evaluate what I actually enjoyed about the work. Building teams. Solving complex valuation problems. Creating systems that scale without sacrificing quality. That reflection led directly to cofounding H&T Appraisal.
The lesson was that failure does not always come from poor performance. Sometimes it comes from outgrowing a situation. Learning to recognize that earlier would have saved time, but recognizing it at all made the next chapter possible.
What is one business idea you’re willing to give away to our readers?
Build a niche review service for complex appraisals. Not full production. Just second looks. There is real demand for independent judgment.
What is one piece of software that helps you be productive? How do you use it?
Excel. Still. I build my own models. It forces me to understand assumptions rather than hide behind software outputs.
Do you have a favorite book or podcast you’ve gotten a ton of value from and why?
I return often to The Checklist Manifesto. It reinforced that discipline and simplicity scale better than talent alone.
What’s a movie or series you recently enjoyed and why?
The Bear. It captures pressure, standards, and leadership under stress better than most business shows.
Key learnings
- Depth of judgment often matters more than speed or volume.
- Complexity can be a career accelerant when approached with discipline.
- Local knowledge and firsthand observation remain critical in data-driven fields.
- Career setbacks can become inflection points when identity is not tied to title.