Jonathan B. Fishbeck of EstateSpace: “Keep it simple”

You set the tone (culture) by listening to your team, making hard decisions in the best interest of the business, and applying feedback in a meaningful way. Jonathan B Fishbeck is the founder and CEO of EstateSpace, LLC, a technology platform that enables and simplifies how you handle lifestyle management service and operations to maintain […]

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You set the tone (culture) by listening to your team, making hard decisions in the best interest of the business, and applying feedback in a meaningful way.

Jonathan B Fishbeck is the founder and CEO of EstateSpace, LLC, a technology platform that enables and simplifies how you handle lifestyle management service and operations to maintain real-property assets to help reduce risk and protect wealth succession. EstateSpace is a licensed Managed Security Services Provider (MSSP) in order to support our enterprise clients. Before devoting his work full-time to EstateSpace, Jonathan served as the Founder and CEO at a design-build firm whose focus was advising, designing, constructing, and operationalizing sizable estate properties for ultra-high net worth families and family offices. It’s this experience and expertise combined with Jonathan’s technology background that was the genesis for EstateSpace. The firm is family funded and operates as a modern business model (MBM) consisting of three main components. Packaged offerings with a multi-sided subscription model, a marketplace for all sides to interact, and AI machine learning to personalize each experience.

In addition to being a technology provider, Jonathan serves a number of philanthropic organizations where his passion for helping veterans, children, and cancer research shines through. These positions and organizations include Co-Chairman, Fisher House Foundation, Board Member, Children’s Voice International, and Board Member, There Goes My Hero, respectively.

Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

After founding a design-build firm, serving Ultra High Net Worth families and family offices, we were able to identify a number of issues when it came to life around construction. These countless experiences were everything from minor to major typically resulting from information and communication breakdowns. We believe that we could have a long-term impact through lifestyle management technology. We knew we could help more people across all facets of life, with EstateSpace.

What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

The “aha moment” for us was two-fold: first the idea and then how to build it. The idea came from a unique combination of three things…

1. Experience with clients on the difficulties managing lifestyle, properties, and providers

2. Participation in associations focusing on the private service for our clientele to gain insights

3. Education on the marketplace, finding zero technology that was truly helpful and useful.

We found 2 things that were common among these points, constant breakdowns in communication and information sharing which lead to a myriad of costly issues. Then there was a moment when we figured out how to build it. We were introduced to Barry Libert, an expert in MBMs (Modern Business Models) where we learned how to combine SaaS subscriptions with a marketplace of providers and apply machine learning to the data we gather to expand meaningful connections. This was the moment we knew that EstateSpace could solve real issues and make a positive impact on our clients and partners.

In your opinion, were you a natural born entrepreneur or did you develop that aptitude later on? Can you explain what you mean?

For me, it was a combination of being raised in a family where I watched my father build a business for 25-years and a developed aptitude later on through the experiences as a three-time founder. I believe there is an entrepreneur in all of us and it doesn’t mean you have to become a founder. Regarding aptitude, you will find either through doing or watching if entrepreneurship is right for you but you can apply your experience in a number of ways.

Was there somebody in your life who inspired or helped you to start your journey with your business? Can you share a story with us?

Both of my parents inspired me to start this journey. My father did the work in the office, while my mother did the work behind the scenes, both teaching me what it would take to be successful. Both roles were equally important and carried with them great lessons about determination and constant encouragement. I’m thankful for my family’s support to this day which is what inspires me as much as I may inspire others.

What do you think makes your company stand out? Can you share a story?

The answer lies within what we hear from our clients, partners, and team members. We’re honest, transparent, and fun to work with. Our clients know that we’re always available and here to help protect their interests without waver. We have been blessed with a number of amazing partner relationships. Our team members feel like part of the EstateSpace family and we love the reciprocation of learning from one another. This is a testament to our beliefs and why we exist, to help people. Knowing our “why” has helped us to build amazing professional and personal relationships, as a company and as individuals.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

Three character traits at the heart of my personal success are openness, conscientiousness, and extraversion. First, the openness to listen to those around you and apply it, to be different and special as a company, and the openness to be wrong, admit it, and become better has served me very well. Second, being conscientious has allowed me to remain steadfast in self-discipline and leading by example, staying milestone-driven and deliberate in how we operate and maintaining focus. Third, extraversion in the ability to share my passion in every aspect of business and life. This has allowed me to build relationships that I care about deeply and show it, but also giving me the strength to be assertive at the right times and make hard decisions.

Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?

This is a great question. I would have to say that “we needed to emulate a larger business if we wanted to be a larger business.” This led us down a costly path of poor investments into physical infrastructure which ultimately became sunk costs. It’s all about digital infrastructure and having limited liabilities. The truth is you can be much bigger than you think and bigger is not usually better in the case of start-ups. One of the great things about EstateSpace is that we are reaching a point now where we’re able to use the platform to run our business, which has been a goal from day one.

Which tips would you recommend to your colleagues in your industry to help them create a work culture in which employees thrive and do not “burn out” or get overwhelmed?

Slow down to speed up. There is a lot of work ahead, I believe in three key rules: 1. Take care of yourself (you are most important) 2. Take care of your family and home life (second most important) 3. Then come to work and be ready to work hard (work is the least important of these 3 things). The results are remarkable — increased productivity, a positive team impact, and fostering an amazing culture of care. This is easier said than done but the reward is well worth the effort. I attest our culture at EstateSpace to this discipline.

What would you advise other business leaders to do in order to build trust, credibility, and Authority in their industry? Can you help articulate why doing that is essential today?

As a business leader, you must have the right core values personally and professionally to get to any of these three achievements. So, let’s assume you’re honest, you have integrity and you truly care; now you can build trust on multiple dimensions with your employees, partners, providers, and clients. You can think of trust as your relationship capital and the most valuable thing in your business. Trust is the most important because it allows you to get more out of your team and starts building your credibility. Show up every day and do what you say you are going to do, that will influence your culture. That influence will transcend into your people, products, and services. Don’t be fooled here, just because something “works”, it doesn’t equal credibility. With these pieces in place, you can gain authority and traction. This is where businesses feel like “they made it” and rightfully so. But don’t become complacent with early success no matter how big, this is where a lot of companies fail. Don’t lose sight of why you exist, how you got here, and what you believe in. It’s these core things that will keep you focused and earning more of all the above over time in the right manner.

What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

I believe the #1 mistake made is not having good mentorship and a process in which to construct a business. Now how do you avoid this…

  1. Find a mentor in your space that has been there and done that
  2. Define what you believe in and “why” you exist
  3. Keep it simple

What I’ve learned is that there is a process that can be applied to any business and the skills you’ve built up professionally are highly applicable. The process just allows you to apply them in a simpler, more effective way because it makes us slow down and focus on only what is important.

Ok fantastic. Thank you for those excellent insights, Let’s now shift to the main focus of our interview about How to Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur. The journey of an entrepreneur is never easy, and is filled with challenges, failures, setbacks, as well as joys, thrills and celebrations. This might be intuitive, but I think it will be very useful to specifically articulate it. Can you describe to our readers why no matter how successful you are as an entrepreneur, you will always have fairly dramatic highs and lows? Particularly, can you help explain why this is different from someone with a “regular job”?

There is a saying that you can only control what you can control, which is true. This is why you will have highs and lows no matter what. An employee does something good or bad, it affects you. The company has a success or failure, it affects you. Everything has an impact on you as an owner and it’s important that you find your ability to take everything and leverage it for good. That much you can control. As an employee with a “regular job,” you’re greatly insulated from the constant highs and lows that an entrepreneur is forced to go through.

Do you feel comfortable sharing a story from your own experience about how you felt unusually high and excited as a result of your business? We would love to hear it.

That’s easy, the excitement of launching our commercial product here at EstateSpace was number one in my book. Seeing people use our application in ways we intend and other ways in which we might not have seen possible. This is why I believe clients become the greatest idea generator and you must listen to what they’re saying. Then closing larger clients that can see your vision and want to share in it, that’s amazing. Share your vision to truly achieve it.

Do you feel comfortable sharing a story from your own experience about how you felt unusually low, and vulnerable as a result of your business? We would love to hear it.

That’s also easy, downsizing. Taking the advice to grow big forced us to a point where we had to downsize. These are those hard decisions that you must make. Putting the success of the business before your own helps you deal with the lows. Looking back on the lows that make for the biggest highs. Stay humble, stay focused and you will optimize your own successes throughout the journey.

Based on your experience can you tell us what you did to bounce back?

I found mentorship at the right time and in the right way. Like so many, my journey is unique yet the same. As entrepreneurs, we all have a story where we do almost this and almost that. In the end, you must believe that it will work out and have faith in the process. Today, I try to remain thankful for all the highs and lows in my journey here at EstateSpace.

Ok super. Here is the main question of our interview. What are your “Five Things You Need To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur”? Please share a story or an example for each.

The five things you need to successfully ride the waves of being an entrepreneur are patience, passion, resourcefulness, willingness to improvise and listen to others, and strong determination to succeed. In the beginning, you must be patient through the excitement of starting a business. This balances the passion you have to be an agent of change with aspirations to make an impact. Resourcefulness is best realized when you find yourself wearing many hats, remember it’s your business and that is something only you have. No one will work as hard as you in your business, so don’t expect it and don’t let it happen. You set the tone (culture) by listening to your team, making hard decisions in the best interest of the business, and applying feedback in a meaningful way. Now you have buy-in and your determination will become infectious. It will be these things all working together that will help you get through the peaks and valleys. This is what you have to keep in mind if you want to be a successful entrepreneur yourself.

We are living during challenging times and resilience is critical during times like these. How would you define resilience? What do you believe are the characteristics or traits of resilient people?

Resilience is something my good friend and colleague, Kris Coleman has taught me a lot about over the years. His firm, Red 5 Security, specializes in preparing their clients for unique situations through their R.E.A.L. program. The number one thing I’ve learned about resiliency is while it is very much a physical skill set, it is equally a mental skill and you must keep both active. Kris recommends building resiliency into the way you operate, which provides continuous improvement and is where you can find sustained success.

To me, resiliency is being aware and prepared. Your ability to handle high-pressure situations by preparing mentally, emotionally, and strategically will impact those on your team. Whether expected and unexpected situations arise, managing feelings starts with understanding what causes them and why they occur. These traits are no different than the ones required to become a successful entrepreneur. Your personal resiliency enables you to build it into your business operations. By remaining aware, resilient people can maintain control of a situation and think of new ways to tackle problems.

Did you have any experiences growing up that have contributed to building your resiliency? Would you mind sharing a story?

Thinking back, I cannot attribute a single story to my own personal resiliency. It is something that has come with my experiences in business and life. If I had to choose, sports were a major contributor in my life — specifically winning and losing football championships. I recall losing in our first attempt to win a championship and wanting nothing more than to work harder to get another chance. Luckily, I was able to be a part of many teams that shared that desire and we won a number of championships.

Growing up I was a big kid, so I ended up playing offensive and defensive line. On either side of the ball, you counted on the person next to you to do their job and they counted on you. Success was only achieved when all 11 guys were working together and doing their part. This taught me the meaning of team and roles. I was not the person that scored a touchdown but I helped score the touchdown with a key block of a forced fumble. The same holds true for business especially as an entrepreneur, you must remember that alone being resilient may not be enough and it takes a team effort in many cases of success. Stay resilient by teaching your team to be prepared to learn from the one you taught.

In your opinion, do you tend to keep a positive attitude during difficult situations? What helps you to do so?

Keep it simple and remember everything is an opportunity. That’s how you stay positive during difficult situations and maintain an effective approach to problem-solving. Bit of advice I have to remind myself of…you think your team is always counting on you to have a plan. If you’re stuck, be honest and you’ll find your team will be there with ideas on approach and strategy because the traits and best practices you follow daily prepare them for these moments. Now your vision is our vision, you’re business is a force to be reckoned with.

Can you help articulate why a leader’s positive attitude can have a positive impact both on their clients and their team? Please share a story or example if you can.

Your attitude and effort are apparent to those around you. No one is strong at everything, so know your strengths and know your weaknesses. Find those who compliment you and then let them do their jobs. This showcases your confidence both in you and others around you, your team and clients will see this. This fosters a culture of positivity that far outweighs an individual and helps you remember what is most important. To have a positive impact is one thing, it’s living by your core values and how you get there that matters.

Ok. Super. We are nearly done. What is your favorite inspirational quote that motivates you to pursue greatness? Can you share a story about how it was relevant to you in your own life?

Very few people or companies can clearly articulate WHY they do WHAT they do. By WHY I mean your purpose, cause, or belief — WHY does your company exist? WHY do you get out of bed every morning? And WHY should anyone care? People don’t buy WHAT you do, they buy WHY you do it!” -Simon Sinek

This is relevant in my personal life because the why is the same, I only have one WHY… I exist to help people. So, both in business and in life I wake every day with a single purpose. Once you find your purpose things get easier, they get better. Like my mentor did to me, I challenge every entrepreneur I meet to find their WHY because in most cases their business depends on it.

How can our readers further follow you online?

We make it easy to get in touch with us. We built the company on the relationships forged over decades of doing business and our dedication to service keeps us focused on continuing to build strong client and partner relationships today.

Anyone interested in EstateSpace can get in touch with us by going to or going to one of our many social channels (LinkedIn, Facebook, Twitter) and reaching out directly. We welcome the opportunity to help in any way we possibly can.

This was very inspiring. Thank you so much for the time you spent with this. We wish you continued success and good health!

Thank you!

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