A Founder’s Journey Includes Family and Friends With Daniel J. Siegel

A Founder’s Journey Includes Family and Friends With Daniel J. Siegel

VENTEUR spoke with attorney Daniel J. Siegel, a nationally recognized authority on ethics, technology, data protection, and business workflow management, about his entrepreneurial journey. Siegel is the principal of both the Law Offices of Daniel J. Siegel, LLC and Integrated Technology Services, LLC. He provides techno-ethics counsel to solo, small and mid-sized law firms on cybersecurity, technology, and other related issues. His practice includes representing individuals in workers’ compensation and personal injury claims; drafting estate planning documents; representing attorneys in disciplinary matters, providing professional responsibility guidance to attorneys and firms, serving as appellate counsel, and representing individuals in workers’ compensation and personal injury matters. 

Siegel is a speaker and author, and serves as the Chair of the Pennsylvania Bar Association Committee on Legal Ethics and Professional Responsibility, and Secretary of the American Bar Association’s Law Practice Division. The author of 14 books, Dan is a columnist and frequent lecturer on a wide range of topics, including ethics, technology, substantive law, appellate law, and professional responsibility matters.

Daniel J. Siegel / Photos courtesy of Daniel J. Siegel

The Journey

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

Resilience and the ability to adapt are crucial and are at times easier to follow in theory than in practice. 

With that knowledge in hand, I have discovered that I have become less a creature of habit and more willing to go with the flow, and listen. 

I have also learned that I am more willing to seek advice and to confer with others.

The entrepreneurial journey is often lonely. Have you experienced loneliness as an entrepreneur? If yes, what was that experience like, and how did you overcome it? If not, why do you think this is the case? 

At first, sitting alone in my office was the loneliest moment, wondering whether clients would call. 

From there, the most solitary moments were the ones with challenges, whether the issue was financial, personnel, or some other situation. 

In those times, I felt I was the first person to address these questions. Ultimately, I learned that many resources exist, from friends to consultants to family to online resources and that using them helps answer many questions.

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

I have learned that first impressions are not always accurate.

Thus, my gut feeling, while helpful, must be balanced against the need to recognize that clients, customers, employees, and friends are as stretched as I am and that it is best to be patient and develop relationships rather than reach quick conclusions that are ultimately inaccurate.

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 didn’t experience all of these situations, but I have encountered some, such as sleepless nights and the ruminations that lead to stomach agita. 

During those times, I tried to divert my attention to family, friends, and other less pressing matters. 

Then, when I return to the source of my problem, I can think things through. 

That said, one of the reasons I became an entrepreneur was to escape the challenges of a longer commute and bosses whose demands and personalities were not always reasonable. 

In exchange, I was able to be home for dinner almost every evening and savor moments with family that many friends missed. 

These decisions have been crucial to my ability to succeed. 

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. Predicting the Future

As I noted, flexibility has been critical to my success. 

When I opened my law office, I anticipated practicing law in specific areas, only to discover that those areas would be dominated by a few firms that monopolized the airwaves and billboards, causing me and other colleagues to experience a dramatic drop in business. Rather than be defeated, I refocused my practice and developed more “niche” areas where my clients appreciate quality, client-focused service rather than representation based on the loudest ad.

2. Hiring Based on the Need To Fill a Position Rather Than Based on Qualifications

It is easy to hire people because you have a need. That only works if the person meets your needs and is qualified. 

Every time I hired someone to fill a position rather than to fill a position with a qualified person was a mistake. 

Don’t do it. 

Waiting for qualified candidates is far preferable to settling, firing, and rehiring.

3. Failing To See a Broader Picture

Finally, it is easy to believe that your problem is all yours and that the heavens are crashing in. In most cases, it helps to consider the issues I am confronting on a broader scale and recognize how others have addressed them.

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. Value Your Family

They are the people who love you and support you. 

When times are challenging, always be candid with your family and close friends and include them. 

They can help. 

Many of my friends have done the opposite, always with unpleasant results.

2. Stay on Top of Costs

It is easy to ignore the costs your business incurs, and it is crucial to oversee the finances and be a prudent fiscal planner.

3. Get Advice

So many people can help, whether it is your accountant, consultant, coach, or colleague, use them. They want to help. 

The Successes

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

1. Competition That Wants To Put You Out of Business

My law practice initially focused on areas where one firm desired to eliminate competition, and it was impossible to outspend them, nor did I desire to do so. 

Instead, I developed niche areas within my practice where my skills and expertise were more important to clients than puffery. 

This ability to adapt kept me in business.

2. Juggling Schedules

Don’t be afraid to ask clients, and others, to adjust their calendars so that you can meet all of the demands and obligations that often arise when entrepreneurs are solos or in small firms. 

3. Find Good People

The labor market is tough. 

It is easy to settle, and it is a mistake. 

Take the time to be patient and hire the right people. 

Sometimes, the wait can be long, with no end in sight, but if you are patient and outline the qualifications you need judiciously, the right people will come along. 

The Advice

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

Schedule your life. I set time to exercise every day, take a lunch hour, and aim to have a family dinner. But things don’t happen unless you schedule them, so put those events, as necessary, on your calendar, and don’t allow work to overwhelm your life.

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

1. Hug Your Family

They are your rock and are essential to professional and personal success.

2. Have a Budget and Monitor and Follow It

It is easy to build up debt, but budgeting and monitoring finances can avoid many of these problems.

3. Don’t Burn Bridges

This wasn’t my problem, but it was for some of my colleagues, but it is easy to burn bridges, and the people with whom you maintain relationships can sometimes become your best clients, no matter how hard it is to do.

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?


When you succeed, there is a level of satisfaction that cannot be matched when serving as a worker bee. 

When I started my business, my wife reminded me that my father and grandfathers were all entrepreneurs, and they succeeded and were happy. 

You view clients differently when they are your clients, not just customers. 

They are also partners, a role impossible to fill when you are an employee.


Is there anything else you would like to share?

Be open and flexible, and never hire jerks. 

Compatibility and respect are crucial. 

So, too, is openness; my staff knows when things are good and when they are tight, and I respect that. 

If your staff respects you, it is easier to succeed.

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