VENTEUR spoke with Jonathan B Fishbeck, the Founder and CEO of EstateSpace, a platform to simplify estate management. EstateSpace helps clients simplify how they manage operations, communicate, and share information. With families, family offices, a network of service providers, and a commitment to transparency and equality in estate management, they are breaking the mold on how estates operate.  

Before devoting his work full-time to EstateSpace, Fishbeck served as the Founder and CEO of a design-build firm whose focus was advising, developing, and operationalizing sizable estate properties for Ultra-High Net Worth families and family offices. This experience and expertise, combined with a background in technology, was the genesis for EstateSpace. In addition, Fishbeck serves several philanthropic organizations where his passion for blood cancer research and helping veterans and children shines through.

Jonathan B Fishbeck

The Journey

The entrepreneurial journey is one of self-discovery. What have you learned about yourself while building your business?

Great question! The most incredible journey for me is life and working to soften myself and my heart. If you are lucky enough to become an entrepreneur, you know that it teaches you more about yourself than anything else. 

Some of the key takeaways from this have been that my passion outweighs everything, I’ve become more resilient and strategic, and failure is a few steps to success. 

My favorite part of life is my family and the amazing people surrounding me.

The entrepreneurial journey is often lonely. Have you experienced loneliness as an entrepreneur?

Yes to feeling lonely at times when it comes to the ultimate burdens. But I am transparent with my mentors and team members because I believe their involvement is key to the business's success and my personal growth. 

I’ve learned that being on a journey alone is not much fun no matter what you’re doing, be it personal or professional. 

If you feel alone all the time as an entrepreneur, you have the power to change that by asking for help and listening to the answer. Getting a good team of advisors who understand your space is essential. Surround yourself with other founders as this can be your best point of education. 

No one part of a business is more complex than the next; it’s all tough. Getting good advice can help avoid the costliest mistakes when you first start.

The Psychological Warfare 

Entrepreneurs generally sleep less, work more, and let their health slip. This combination, combined with loneliness, often results in insecurity, self-esteem issues, and low self-worth. Have you experienced any of these issues as an entrepreneur?

I firmly believe that you must take care of yourself and your family, and then go to work. 

This is the heart of our culture at EstateSpace. 

I have not experienced these things to the extreme for an extended period. Granted I have had my share of moments. Overall, I have a fantastic support system from my wife and kids to my parents, siblings, and mentors. They have all helped me take care of myself physically and mentally.

Newer entrepreneurs often equate their personal success with the success and value of their business. If their business fails, they are a failure. If their business succeeds, they are a success. Have you experienced this warped perception of reality? 

I have seen this with other entrepreneurs and can understand how this can happen. I once felt that way myself. There is a lot of pressure in many cases to improve the investment you’ve taken, and money can feel like a significant driving metric in our world. But through great mentors, I’ve learned that many metrics matter, and while ROI is a big one, it is not the only one. There are ways to get to your goal and succeed; most of the time it’s not how you draw it up but how you make it happen. 

What are your three biggest fears as an entrepreneur, and how do you manage those fears?

1. Not Achieving My Mission for the Business

To help manage this fear, I find it helpful to break everything down into bite-size chunks, and I take it one day at a time.

2. Not Knowing What I Need To

To combat this, surround yourself with mentors who have been there and done it and other founders you can learn from, share learnings, and bounce ideas off.

3. Running Out of Money Before Being Cash Flow Positive

It’s essential to manage a budget and grow within your means. Take chances when necessary. Know it will all work out if you have good people beside you.

The Mistakes

What are three mistakes you made early on as an entrepreneur, what did you learn from them, and how can others avoid these mistakes?

1. Not Having the Right Advisors From the Start

From this mistake I learned that you have to get good advice from day one. Be sure to find an advisor who has done what you’re trying to do and can help you navigate the challenges ahead.

2. Not Being Organized on Product Development

Be sure to strategize by having a clear plan for development that supports your revenue goals. 

3. Not Aligning Our Corporate Structure With Long-Term Goals

Ensure you’re adequately capitalized and have the proper structure for what the company is ultimately trying to achieve. 

What are three things you see that are often overlooked by entrepreneurs you encounter, and how can other entrepreneurs be aware of these things from the beginning? 

1. A Lack of Corporate Structure With Proper Governance

Start from the bottom and work your way up. Company structure and governance are the foundation of your venture, and you don’t need to go into it alone and unaware (get an advisor!). 

2. The Ability To Financially Plan and Model Performance

Be aware that preparing financially is the least expensive thing you can do, so do it well before you start burning capital. 

3. Organizational Growth To Support the Business

Figure out the best way to grow and leverage fraction services for as long as possible to avoid unnecessary overhead.  

The Successes

What are three seemingly insurmountable obstacles you’ve faced as an entrepreneur, and how have you overcome them?

1. Cash Flow Shortfalls

Looking back, I can’t believe how many times I had a shortfall and we figured it out.

2. Product Development Failures

We had to make cuts, revise release plans, and in some cases start over with the technology because we got it wrong the first time.

3. Downsizing the Business

Letting people go is hard, and failing is more complex, but the reward of making it through everything is excellent. I have learned far more in the most challenging times, leading to our success.

What are three ways you have managed to boost your productivity without causing burnout?

1. Getting a Coach

I’ve found that productivity is essential but not the most important. First, you must take care of yourself and ensure your family is supported. Now you’re ready to go to work and be productive without personal burdens weighing you down. Coaching has helped save me through education on self-health and awareness.

2. Time Block

Be honest and present on time, blocking your efforts and taking things one day at a time. 

3. Being Honest With Yourself

Being honest with yourself is challenging as an entrepreneur; we always want to do more and be superman. 

The Advice

How can newer entrepreneurs develop a healthy work-life balance even when it seems like an impossible task?

This is a challenging task and one that requires daily effort. Time blocking is the best place to start. Set boundaries for yourself and your family. Put them first and then go to work. You will find that your employees also love this same balance which can help foster a fantastic culture.

What three key pieces of advice would have made your entrepreneurial journey easier, and why?

1. Slow Down to Speed Up

Don’t try too much; this helps you gain and maintain focus.

2. Everything Will Be Okay

Somehow it will all be okay, and the learning experiences are valuable.

3. You’re Not Alone! 

Find yourself a network of other founders like you and grow together.

What do you think the most significant difference is between how an entrepreneur sees their career path versus how an employee at a company sees their career path, and why?

As an employee, the path is well-defined for you, and certain people need that structure to succeed.

As an entrepreneur, you define your own path, which is not for everyone. The risk level is exponentially greater, but so is the reward.

In both cases, everyone can make a difference in what they do and help leave the world a little better than they found it.

What role has intuition played in your success as an entrepreneur, and why do you think this is the case?

Intuition is significant; it helps guide you along the journey. When you couple that with good advisors and a good plan, you increase your chance for success. 

Doing what you know is right makes things easy and fosters a healthy work environment for those around you. 

Don’t be scared to trust your instincts and follow your gut feelings.


Is there anything else you would like to share?

Startups have helped redefine how the world works and can work. Any one idea can create an impact far beyond one’s imagination. Being an entrepreneur is one of the best experiences in my life. Remember to give back and learn from others; the community of people is what makes being an entrepreneur so outstanding. Best of luck!

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