Jonathan Drew Keller is a financial advisor, entrepreneur, and real estate investment professional. His career focuses on wealth management, tax planning, and alternative investment strategies. For more than 25 years, Jonathan Drew Keller has helped real estate investors transition from active property ownership to passive, income-producing investment strategies. Through his leadership of 1031 Solutions, he has guided clients through tax-efficient investment opportunities involving Delaware Statutory Trusts (DSTs), alternative investments, and diversified real estate portfolios.
Since 2001, Mr. Keller has served as president of 1031 Solutions, a firm specializing in 1031 exchanges and alternative real estate investments. Under his leadership, the company has helped investors transition from actively managed properties into professionally managed, income-producing real estate investments throughout the United States.
Before recommending investment opportunities, Mr. Keller works with independent professionals to evaluate potential risks, market conditions, and property fundamentals. This disciplined approach helps investors make informed decisions while balancing goals such as income generation, capital appreciation, and risk management.
What is your typical day, and how do you make it productive?
My typical day starts with getting myself mentally organized before I get pulled into everyone else’s priorities. I like to take a little time in the morning to think about what really matters that day—not just what is urgent, but what is important. Running a business can easily turn into a day of reacting to phone calls, emails, and other people’s schedules, so I try to make sure I’m intentional about where I put my time and energy.
A big part of my day is communicating with people. I genuinely enjoy people, and I believe that relationships are at the heart of business. Whether I’m speaking with a client, a professional partner, a colleague, or someone I’ve known for years, I try to give that person my full attention. I’ve learned that people can tell when you are truly listening versus simply waiting for your turn to speak.
I also try to identify the two or three things that would make the day successful and focus on those first. I don’t believe productivity means being busy every minute. Some of the most productive moments are conversations, thinking through a problem, helping someone make a difficult decision, or simply taking a step back and looking at the bigger picture.
For me, productivity is ultimately about progress and people. If I can move something important forward while also making someone’s day a little easier or better, I consider that a productive day.
How do you bring ideas to life?
I bring ideas to life by getting them out of my head and into a conversation as quickly as possible. An idea can sound fantastic when you’re thinking about it alone, but once you explain it to another person, you start discovering what is practical, what needs to change, and what could make it even better.
I’m a big believer in starting before everything is perfect. I would rather take a good idea, put it into motion, learn from the experience, and improve it than spend six months trying to make something flawless on paper. Real-world feedback is incredibly valuable.
I also ask myself a simple question: “Who does this help?” If an idea doesn’t genuinely create value for another person, I question whether it is worth pursuing. When the answer is yes, I start looking for the people, resources, and systems that can turn the concept into something real.
The other ingredient is persistence. Most worthwhile ideas don’t move from concept to reality in one giant leap. They develop through a series of conversations, adjustments, mistakes, and small victories. I enjoy that process. There is something incredibly satisfying about seeing an idea that once existed only as a thought become something that actually improves someone’s experience.
What’s one trend that excites you?
One trend that genuinely excites me is the way technology is making highly personalized service possible at scale. We are living through a period where technology, particularly artificial intelligence, can take enormous amounts of information and help people organize it, understand it, and act on it much more efficiently.
What excites me isn’t technology for technology’s sake. It is what technology can allow people to do with their time. If a computer can eliminate some of the repetitive administrative work, that gives a human being more time to have a meaningful conversation, solve a complicated problem, build a relationship, or simply be more present.
I think the winners in the future will be the people and companies that combine technology with humanity rather than choosing one over the other. Technology can process information incredibly quickly, but it can’t replace genuine empathy, trust, judgment, or the feeling a person gets when they know someone actually cares about them.
That combination—better technology and more human connection—is something I find very exciting.
What is one habit that helps you be productive?
One habit that has helped me tremendously is making a point of finishing important conversations rather than allowing them to linger indefinitely. If something needs to be discussed, I try to pick up the phone, have the conversation, make the decision, and move forward.
I’ve found that unfinished conversations and unresolved decisions take up far more mental energy than we realize. Sometimes we spend three days thinking about a five-minute conversation we could have had on Monday.
I also try to begin each day by identifying what absolutely needs my attention. That keeps me from confusing activity with productivity. There will always be another email, another phone call, and another task waiting for me. The challenge is making sure the things that truly matter don’t get pushed aside by the things that merely feel urgent.
For me, productivity is less about doing more and more about being deliberate about what deserves my attention.
What advice would you give your younger self?
I would tell my younger self to slow down, enjoy the journey, and understand that not everything has to happen immediately. When you’re younger, it is easy to believe that you have to constantly be moving toward the next accomplishment—the next deal, the next goal, the next level of success. With experience, you realize that life isn’t a race.
I would also tell myself to put relationships ahead of accomplishments. Business matters. Financial success matters. Career goals matter. But at the end of the day, the people you have helped, the friendships you’ve developed, the family you’ve spent time with, and the way you treated people are what give those accomplishments meaning.
I would tell myself not to be afraid of making mistakes. Some of the lessons that stay with us the longest come from things that didn’t work out the way we expected. You don’t have to have everything figured out. You just need to keep learning.
And perhaps most importantly, I would tell my younger self to be exactly who I am. Don’t spend too much time worrying about whether everyone likes you. Treat people well, work hard, keep your word, stay curious, and bring positive energy wherever you go. The right people will appreciate you for it.
Tell us something you believe almost nobody agrees with you on?
I don’t know if I would say that almost nobody agrees with me, but one belief I have that sometimes runs contrary to conventional thinking is that being a genuinely nice person is not a weakness in business—it can actually be one of your greatest strengths.
There is sometimes an assumption that business is about being tougher, more aggressive, or always trying to get the better end of the deal. I have found that long-term success is often built differently. It comes from being someone people trust, someone who returns the phone call, someone who keeps their word, and someone who genuinely wants the other person to do well.
I believe you can be competitive without being adversarial. You can be successful without making someone else feel unsuccessful. You can negotiate firmly while still treating people with respect.
I’ve always believed that the energy you bring into a room matters. People remember how you made them feel. They remember whether you listened, whether you cared, whether you helped them, and whether you were there when they needed you.
I also believe strongly in treating other people the way you would want to be treated. I believe in what many people would call good karma—not as something you do because you expect a reward, but because kindness has a way of making the world better for both the person giving it and the person receiving it.
What is the one thing you repeatedly do and recommend everyone else do?
I repeatedly reach out to people just to stay connected. Not because I need something from them, not because I’m trying to sell them something, and not because there is necessarily a business opportunity involved. Sometimes it is simply a phone call or a message saying, “I was thinking about you. How are you doing?”
I think we underestimate how meaningful that can be. Everyone is busy. Everyone has responsibilities. Sometimes people can go months or even years without hearing from someone they care about.
I’ve learned that relationships require maintenance just like anything else of value. If you want a strong relationship with your family, your friends, your clients, or your professional network, you can’t only show up when you need something.
My recommendation is simple: reach out. Call someone. Take someone to lunch. Send a handwritten note. Congratulate someone on a success. Check on someone who is going through a difficult time. Celebrate someone else’s good news.
It doesn’t cost much, but it can mean a tremendous amount. And I’ve found that the more generosity you put into your relationships, the richer your life becomes.
Sometimes the smallest gesture can have an enormous impact on someone else’s day. And, interestingly, I’ve found that doing something kind for another person often has an equally positive effect on the person giving the kindness.
When you feel overwhelmed or unfocused, what do you do?
When I feel overwhelmed or unfocused, I try to stop adding more noise to the situation. My first instinct is to step back and simplify everything. I ask myself, “What actually needs to happen right now?”
Usually, the answer is much smaller than the problem initially feels. Instead of thinking about everything that needs to be done, I identify the next meaningful step. Once I take that step, the next one generally becomes clearer.
I also find that getting away from the desk can be surprisingly productive. A walk, a quiet conversation, or simply a little time away from screens can completely change my perspective. Sometimes the answer doesn’t come from staring harder at the problem; it comes from giving your mind enough space to see it differently.
And I remind myself that feeling overwhelmed doesn’t mean you’re incapable. It usually means you have a lot on your plate and you’re trying to care about all of it at once.
I’ve also learned this lesson from my own experience. When I became involved in a business outside of my core business, I allowed too many things to compete for my attention. Once I recognized that the situation wasn’t right for me and I removed myself from it, I immediately felt a tremendous difference.
The goal isn’t to eliminate every challenge. The goal is to stay calm enough to deal with the challenge in front of you and have the clarity to recognize when something is creating unnecessary stress in your life.
What is one strategy that has helped you grow your business or advance in your career?
The strategy that has probably helped me most is investing in relationships for the long term rather than viewing every interaction as a transaction.
In a relationship-based business, people have choices. They can work with you, refer you, return to you, or introduce you to someone else. But none of that happens simply because you asked them to. It happens because they trust you.
I’ve tried to build my career by being the person people know they can call. Sometimes that means answering a question that doesn’t immediately generate revenue. Sometimes it means making an introduction, sharing information, or helping someone think through a situation even when there is nothing directly in it for me.
Over time, those small acts compound. A client becomes a repeat client. A professional contact becomes a friend. A friend introduces you to someone else. Someone you helped years ago remembers you when an opportunity arises.
That’s been one of the biggest lessons of my career: you don’t build a great business one transaction at a time; you build it one relationship at a time.
When people know that you genuinely care about their success, business becomes a natural extension of the relationship rather than the entire purpose of it.
What is one failure in your career, how did you overcome it, and what lessons did you take away from it?
One of the biggest learning experiences in my career came from getting involved in a business outside of my core business, 1031 Solutions. At the time, I thought it could be an interesting opportunity and something I could successfully add to everything else I was doing. What I didn’t fully appreciate was how much of my time, attention, and mental energy it would require.
What started as an opportunity gradually became a distraction. Instead of putting my full focus into the business I had built and was passionate about, I found myself dividing my attention between two very different things. I became increasingly stressed, and I could feel that it was affecting me personally. I wasn’t enjoying things the way I normally do, and I was experiencing anxiety that simply wasn’t consistent with who I am or how I like to live my life.
Eventually, I had to be honest with myself. I realized that just because something looks like a good opportunity doesn’t mean it’s the right opportunity for me. I made the decision to immediately terminate my involvement and put my energy back where it belonged—with 1031 Solutions and the clients and relationships that I genuinely care about.
The change was remarkable. Almost immediately, I felt a tremendous sense of relief. My life became better, my stress decreased, and I found myself enjoying my work and my day-to-day life again. It was a powerful reminder that sometimes the best business decision you can make is knowing what not to do.
The lesson I took away is one I will carry with me for the rest of my career: stay in your lane when your lane is where your passion lives. I don’t believe every opportunity is meant for every person. I’ve learned to ask myself not only, “Can I do this?” but also, “Do I really want to do this, and does it belong in my life?”
I’m passionate about 1031 exchanges, I love helping people navigate what can sometimes be a complicated process, and I genuinely enjoy the relationships I’ve built through this business. When I returned my full attention to that, everything felt right again.
So, while I wouldn’t call the experience a failure in the traditional sense, it was certainly a mistake—and one that I’m actually grateful I made. It taught me something about myself that I might not have learned otherwise. I learned that success isn’t necessarily about pursuing every opportunity that comes your way. Sometimes success is having the clarity and courage to walk away from something that isn’t right for you.
What is one business idea you’re willing to give away to our readers?
One business idea I would give away is a “Life Administration Concierge”—a service designed to help busy individuals and families manage all of the complicated administrative tasks that come with major life events.
Think about what happens when someone buys or sells a home, gets married, has a child, moves to another state, inherits property, starts a business, retires, or settles an estate. The actual event may be exciting, but the administrative checklist surrounding it can be overwhelming: documents, professionals, deadlines, insurance, financial institutions, utilities, records, appointments, and dozens of small details.
The business would provide clients with one central person who helps coordinate all of those moving pieces. It wouldn’t necessarily replace the attorney, accountant, financial advisor, realtor, insurance professional, or other specialists. Instead, it would act as the quarterback who helps the client keep everything organized and makes sure important tasks don’t fall through the cracks.
The service could operate on a monthly membership or project-based fee. Technology could handle reminders, document organization, and checklists, while the human concierge handles communication, coordination, and the situations that require judgment and empathy.
I like the idea because it solves a very real problem: people don’t necessarily need more information—they need someone they trust to help them navigate everything that has to happen.
In many businesses, the opportunity isn’t creating something people have never seen before. Sometimes it is simply taking an existing problem and solving it in a more thoughtful, convenient, and human way.
What is one piece of software that helps you be productive? How do you use it?
Without question, one of the pieces of software that has become incredibly valuable to me is ChatGPT.
What I appreciate most about it is that I can use it as a thinking partner. I can have an idea, a question, a business challenge, or even something I’m trying to communicate, and I can work through it conversationally. Sometimes I know exactly what I want to say but haven’t figured out the best way to say it. Other times, I know there is a better way to approach something but haven’t quite found it yet. ChatGPT helps me explore those possibilities.
I use it to brainstorm ideas, organize my thoughts, improve communications, research concepts, simplify complicated information, and look at a situation from different perspectives. It can help me get from a blank page to a workable starting point much faster.
But there’s something important about the way I use it: I don’t see it as a replacement for my judgment or my relationships with people. I see it as a tool that makes me more effective. The technology can help me think through an issue, but ultimately I make the decision. And when it comes to clients, relationships, empathy, and understanding what a person actually needs, I believe there is no substitute for human connection.
One of the things I enjoy most is that it encourages curiosity. I can ask a question, get an answer, challenge the answer, ask another question, and keep going. That process can lead somewhere completely different from where I started.
For me, that’s what makes ChatGPT so useful. It doesn’t just save time; it can help me think better. And when you can combine better thinking with experience, good judgment, and genuine care for people, that’s a pretty powerful combination.
What is the best $100 you recently spent? What and why?
The best $100 I recently spent didn’t really feel like spending money at all. I was standing in line when I noticed an elderly woman who didn’t have enough money to pay for her prescriptions. I simply gave her $100 so she could get what she needed.
There wasn’t a business reason behind it, and I certainly wasn’t expecting anything in return. It was just one of those moments when you see someone who needs a little help and you have the ability to help them.
I believe strongly in treating other people the way you want to be treated. I also believe in good karma—not in the sense that you should do something kind because you’re expecting something good to come back to you, but because doing the right thing feels right.
What made that $100 so valuable to me wasn’t the money itself. It was knowing that, in that particular moment, I was able to make someone’s life a little easier. She needed her prescriptions, and I had the ability to help. It was really that simple.
And the interesting thing is that although the act was completely selfless, it made me feel amazing. There is something incredibly rewarding about helping another person without expecting anything in return. It reminds you that we all have opportunities to make a difference in someone’s day, even in very small ways.
I’ve learned that generosity isn’t always about writing a big check or doing something extraordinary. Sometimes it’s simply paying attention. You notice someone who needs help, you have the ability to help, and you do it.
To me, that was the best $100 I could have spent because it wasn’t really an expense. It was an opportunity to be kind.
Do you have a favorite book or podcast you’ve gotten a ton of value from and why?
One book that has had a lasting impact on me is How to Win Friends and Influence People by Dale Carnegie.
What I appreciate about the book is that, despite its age, so much of its message remains relevant because human nature hasn’t changed nearly as much as technology has. People want to feel heard. They want to feel appreciated. They want to be treated with respect. They want to know that they matter.
One of the things I’ve learned over the years is that you can know an enormous amount about business and still miss the most important part if you don’t understand people. Every transaction, every negotiation, every partnership, and every organization ultimately comes down to people interacting with other people.
The book reinforced something I already believed: genuine interest in other people is powerful. Ask questions. Listen. Remember things about people. Give credit. Be generous with compliments when they’re deserved. And don’t make every conversation about yourself.
I think those principles have value far beyond business. They can make you a better colleague, friend, spouse, parent, leader, and human being.
What’s a movie or series you recently enjoyed and why?
A movie I recently enjoyed was The Secret Life of Walter Mitty. I don’t actually watch a tremendous number of movies, so when I do watch one, I want it to give me something to think about after it’s over.
What I enjoyed about this movie is that, underneath the humor and adventure, it really is a story about living your life rather than simply thinking about living it. Walter spends much of his life imagining experiences rather than having them, and eventually he begins taking chances, experiencing the world, and becoming more present in his own life.
That resonated with me.
I’m a very driven person and I love what I do, but I’ve also learned that life is about more than business and accomplishments. It’s about the people you love, the experiences you have, the places you go, and the memories you create along the way.
It also made me think about how easy it is for successful, busy people to become so focused on responsibilities that they forget to enjoy the journey. I think there’s tremendous value in having ambition, but there is equally tremendous power in living in the moment. I particularly liked the reminder that sometimes you have to put the phone down, stop thinking about the next thing, and actually experience the moment you’re in.
The movie left me with a simple thought: don’t spend so much time planning your life that you forget to live it.
And honestly, that’s probably why I enjoyed it. It was entertaining, but it also gave me something I could take with me after the movie ended.
Key learnings
- Long-term professional success is often built through genuine relationships, trust, consistency, and a willingness to help others without expecting an immediate return.
- Productivity is not simply about being busy; it comes from identifying what truly matters, protecting time for meaningful work, and giving important people and priorities proper attention.
- Technology can make business more efficient, but the greatest opportunities come from combining technology with human qualities such as empathy, judgment, communication, and personal connection.
- Setbacks can become valuable sources of growth when they are approached with honesty, accountability, reflection, and a willingness to learn rather than simply being viewed as failures.
- A meaningful and successful career does not have to come at the expense of kindness. Treating people well, bringing positive energy into interactions, and creating value for others can be powerful foundations for both professional and personal success.