Jeff Herter in Rye, New Hampshire, has built a career around asking questions, staying curious, and taking a long-term view of the work in front of him. Based in Rye, New Hampshire, he is the Principal of Providence Real Properties, LLC, where he works with multifamily properties across the United States.
Herter grew up in Naperville, Illinois, and later attended Boston University’s Questrom School of Business. After graduating cum laude with a degree in accounting, he began his career in financial markets. The experience taught him to stay disciplined under pressure and to recognize that confidence is most useful when it is paired with careful judgment.
His career eventually expanded into entrepreneurship and real estate. Over more than 15 years in multifamily housing, Herter has learned to look beyond buildings and consider the communities around them. He often spends time walking neighborhoods, visiting local businesses, and talking with people who know an area firsthand.
“You learn a lot when you stop assuming you already have the answer,” Herter says. “Some of the best information comes from simply paying attention and listening to people.”
That approach also shapes his work as a volunteer SCORE mentor. Herter enjoys helping small business owners work through challenges, consider different possibilities, and develop their own answers rather than simply telling them what to do.
For Herter, experience has made curiosity more important, not less. Whether he is working with a property, exploring a neighborhood, or mentoring an entrepreneur, he continues to value patience, thoughtful questions, and the small decisions that create meaningful progress over time.
What has inspired you most throughout your career?
I have always been inspired by people who build something useful and stick with it. It does not necessarily have to become a huge company or receive a lot of attention. I find it interesting when someone sees a problem, believes there is a better way to approach it, and keeps working until the idea becomes real. I see that in real estate, but I also see it in the small business owners I meet through SCORE. Some of them are building businesses from very modest beginnings, and their persistence is a good reminder that progress usually happens one decision at a time.
How did your early career shape the way you think about confidence?
Working in financial markets taught me pretty quickly that confidence and certainty are not the same thing. When I was trading derivatives, there were situations where I had to make decisions with incomplete information. You could prepare carefully and still have something unexpected happen.
I think that experience made me comfortable saying, “I don’t know yet.” Confidence does not require pretending you have every answer. Sometimes it means trusting yourself enough to keep asking questions until you understand the situation better.
What gave you the confidence to move into entrepreneurship and real estate?
I would not describe it as one moment where I suddenly felt completely ready. It was more gradual than that. I had developed skills around analysis, risk, and decision-making, and I began seeing ways those skills could apply outside financial markets.
There were doubts. Anytime you move into something new, you wonder whether your experience will translate. I eventually realized that waiting until I felt completely certain would probably mean waiting forever. I focused on what I understood, identified what I still needed to learn, and went from there.
How do you know when an idea is worth pursuing?
My first reaction is usually curiosity rather than excitement. I want to understand why the idea should work. I also spend a fair amount of time trying to prove myself wrong.
That is something I have carried with me throughout my career. If I like an idea, I deliberately ask what I might be missing. What would have to happen for this not to work? Is there a simpler explanation? Am I excited because the opportunity is actually good, or because it is new?
If an idea still makes sense after those questions, I usually have much more confidence in it.
How do you inspire confidence in other people’s ideas?
I try not to tell people that an idea is great just because they are excited about it. I don’t think that helps anyone. Through my work as a SCORE mentor, I have found that people often gain more confidence when they can defend their own thinking.
I might ask someone why their customer would choose them, what problem they are actually solving, or what they would do if their first plan did not work. Sometimes you can see their confidence grow as they answer because they realize they have thought about the business more deeply than they gave themselves credit for.
My job in those conversations is not to provide all the answers. It is often to ask the question that helps someone find their own answer.
Has your definition of taking risks changed?
Absolutely. When I was younger, I probably associated risk with being willing to make a bold move. Today, I think much more about understanding what I am accepting before I move forward.
Taking a risk does not mean ignoring what could go wrong. In my experience, it is almost the opposite. I want to spend time thinking about the downside because that tells me whether I can live with it.
Sometimes the courageous decision is moving forward. Other times it is walking away from something everyone else seems excited about.
Where do you find inspiration outside of work?
I find a surprising amount of it by simply getting out and observing. When I visit different communities, I like walking around rather than seeing everything from a car. I’ll notice an old building being brought back to life, a local restaurant that’s packed on a weekday, or a business owner who seems to know every customer who walks through the door.
Those things interest me because they show what steady effort looks like in real life. A strong neighborhood is rarely created by one enormous decision. It is usually hundreds of people making smaller decisions because they believe the place is worth their effort.
What has getting to this point in your career taught you about success?
Probably that it takes longer than you think and rarely follows the route you planned. My career has moved through financial markets, entrepreneurship, real estate, and mentoring. I could not have mapped all of that out when I graduated from Boston University.
What connects those experiences is curiosity. I have tried to keep learning, stay open to changing my mind, and avoid assuming that experience means I have everything figured out.
The older I get, the more I think success has less to do with having the perfect plan and more to do with developing enough confidence to adapt when the plan inevitably changes.
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