VENTEUR spoke with Bernard Williams, Managing Partner of Company Counsel LLC, about his entrepreneurial journey. Williams focuses his legal practice on helping small business owners beat the odds, make better decisions, and grow companies that impact the world. According to Williams, every big corporation relies on in-house legal counsel to support its operations, risk management, and growth. Company Counsel provides the same type of general counsel legal services to small companies, scaled in a way that makes sense for them.

Before forming Company Counsel, Williams worked in Big Law (Cravath, Dickstein Shapiro, and Drinker Biddle) and was a partner in the Philadelphia business law firm Legis Group LLC, where hd led the litigation practice. Before joining the Legis Group, Williams founded an education company specializing in academic tutoring and test preparation, where he was the owner-operator and general counsel. 

Williams earned a law degree from New York University School of Law, where he served as an editor for the NYU Law Review.

Managing Partner of Company Counsel LLC Bernard Williams / Photo courtesy of Bernard Williams

The Journey

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

I’ve discovered that I have always been an entrepreneur. It just took me a long time to realize it. I get bored quickly with routine tasks. 

I crave variety, love to innovate, and have never responded well to micro-management. 

My instinct is to take the lead and to try to find a way to trailblaze. I feel a lot freer to be myself as an entrepreneur than I ever did as a corporate employee. 

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

It can feel a bit isolating when you are the sole company owner because it can feel like no one understands what you go through or think about. 

When you’re the owner, you don’t have any peers. You have to be a source of strength and confidence for your employees because the last thing you want is employees who are worried about the health of the company or their job security. 

I’ve noticed that employees can be too quick to defer to me and too reluctant to disagree with me, even though I encourage their feedback. For better or worse, in the back of everyone’s mind, the business owner will always be viewed as the boss and treated differently. 

I overcome these feelings of isolation by developing peer relationships outside the company. Family members and friends may genuinely want to help, but they don’t understand what it is like to be a business owner unless they own one themselves. I’ve found mastermind groups to be a great way to meet like-minded entrepreneurs who need an outlet to talk openly about the business, vent, and get honest feedback from people who can relate. 

It is so cathartic when you can let your guard down and talk freely about what is stressing you out about your business without needing to act like you have to have everything figured out. 

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 think my physical health may have improved as an entrepreneur. When I worked in Big Law, I’d stop and get a breakfast sandwich on the way to work, go out to eat at lunch, and sometimes meet people after work for drinks. I ate out all day, almost every day. 

As an entrepreneur, I was motivated to get a lot done, and I noticed that I kept getting a sugar crash after I ate. It would take me hours to regain enough energy to return to work, which wouldn’t do. So, I decided to push back my first meal until later in the day. I delayed the sugar crash, and I got a lot more done. 

I also started to lose weight. Turns out I had stumbled onto what everybody now knows as “intermittent fasting.” I lost 70 pounds and became physically healthier as a result. 

I have often dealt with feelings of insecurity and low self-esteem. 

My profession is at the crossroads of law and entrepreneurship. My peers who stayed in Big Law earn much more money than I do now. Had I stayed on the same track earlier in my career, I would be wealthier now. Sometimes I compare my income to what I used to earn or what I could be earning, and I can’t help but wonder where I went wrong. 

I’ve found to overcome those negative feelings to remind myself that I am on a unique journey and that it doesn’t make sense to compare my path to someone else’s. 

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’m struggling with the concept of personal success that does not correlate to professional success because I think “success” is something that should be measurable or quantifiable. I don’t see how you would measure or quantify personal success without tying it to professional goals. 

I also think it is natural for high performers to equate personal success with professional success. We live in a society that places a high value on professional success. People brag about being busy. We sacrifice personal time and rest in the name of being productive. I don’t think that is unique to entrepreneurs. 

When I ran my first business 14 years ago, I eventually had to close the doors and declare bankruptcy. It was demoralizing because I had so much of my pride and self-worth tied into the idea that my bold career choice to leave Big Law and start a business was the right decision. 

It took me years to be able to talk about that experience because I viewed it as a failure, and I was embarrassed. I now view it as an essential learning experience that is just one part of a long career journey. I don’t think I could do what I do now if my first attempt at business ownership had not humbled me. But if I’m being honest, even though I have come to terms with my early business failure, I still feel that my professional and personal success are the same.  

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

1. My Biggest Fear Is Losing Key Employees

We’re building something unique and special, but it has taken a lot of time and energy to get to this point. If they wanted to, the people on my team could get double what I could pay them. I fear they will get tired of waiting for our company to reach its potential and decide to go elsewhere. 

2. I Fear the Company Will Never Reach a Level of Success That Will Satisfy Me

I have always been an ambitious person. I expect greatness for my company. We have grown our team, increased revenue, refined our processes, and improved our company exponentially over the last six years, but it still feels like a work in progress. There is so much more to do. I fear running out of time before creating the company I believe we can be.

3. Going Out of Business

I know what it’s like to run a company into the ground. To not be able to pay bills. To liquidate my retirement account so that I can make payroll. I remember the guilt, shame, and embarrassment of having to admit to clients, friends, and employees that I just couldn’t make it work. I never want to feel that again. 

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. Believing I Needed To Be All Things to All People

I made this mistake more than once. My first business was a tutoring and a test prep company. We should have been targeting college-bound high school students and their parents. Instead, we offered services as broad as LSAT and GRE prep for (college graduates), adult literacy, and elementary school tutoring for students with special needs. Our messaging was so vague, and we spread ourselves so thin chasing every opportunity that we never really became known as experts in anything. 

2. Unrealistic Forecasts

When I wrote the business plan I submitted to support my loan application, I painted an optimistic picture of a start-up business poised for overnight success. The problem was that I believed my propaganda and legitimately thought we would be profitable in no time. I should have been a lot more conservative with my spending. 

3. Misplaced Trust

In my first six months of business, I said yes to everything. My mentality was that I was not sure what would work, and I did not want to miss out on a great idea. I believed salespeople who told me their product or service was just what my business needed to get in front of the right clients. I agreed to branded merchandise, TV commercials, magazine ads, program sponsorships, and ill-conceived ideas that never generated revenue. 

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. There Will Always Be Challenges and Problems To Solve

You cannot solve all of them in advance and should accept that there will always be more you can do. About three months before I launched my law firm, I created a list of action items I needed to finish to ensure a successful launch. 

I wanted to have processes, services, and pricing clearly defined and branding figured out. When I showed my list of action items to a business owner friend, he laughed at me. Then he explained that the company would never be perfect and that there would always be something to fix or improve. 

2. Culture Is Important

When I ran my first business, the tutoring company, I spent a lot of time the first few months thinking about operations, marketing, and training. However, although I had good personal relationships with my staff, I had neglected to create a culture in the office where they felt like they were part of a team. 

When one of the more senior staff members pointed out that I could have done something as simple as an employee newsletter, I realized that I had completely overlooked the importance of culture for people working at the company. 

3. I Work With Small Business Owners Every Day Who Have Overlooked Legal Issues

They make deals, enter partnerships, and form businesses without putting good contracts in place. Or, potentially worse, they sign contracts without understanding what they are signing. 

The best way to spot legal issues and adequately address them is to work with an attorney you trust. The investment is minimal compared to what you will spend later if there is a problem and you don’t have good contracts.

The Successes

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

1. The Vortex

I founded the company, hired everyone, and personally trained most of our staff. Even as I tried to scale by elevating and empowering other people at the firm, it seemed that employees were running every decision past me and copying me on every correspondence. 

I was drowning in details I did not need to know. We started to overcome this issue by implementing a management structure with a written accountability chart. For each function of the company, the chart identifies 3-5 key responsibilities and the person held accountable for that “seat” in the organization. 

Now, whenever people try to saddle me with issues someone else could handle, I refer to the accountability chart and redirect them. That small change in process has saved me hours every week.

2. Competing With Big Law for Talent

My company is a small law firm. We compete for talent against Big Law firms, but they can pay substantially more compensation and benefits. Their resources dwarf ours. Although we couldn’t compete with their financial compensation, I tried to create an environment where they could have an excellent work-life balance and still thrive and grow as professionals. Junior lawyers can earn more money at other firms but will not have a better experience.

3. Getting My Name Out

I had zero clients when I started my tutoring business and zero when I started my law firm. Things would have been much easier had I started either endeavor with paying clients. Instead, I had to build a client base from scratch quickly. 

I joined a BNI group and did as many coffee meetings as I could fit into my day. I could never have built the business I have today without the network I began building in those early days. 

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

1. Implemented an Entrepreneurial Operating System

I wanted to reduce my stress levels while continuing to grow and scale my company. With the new operating system, people on the team feel more empowered to take risks, be more productive, and have more clarity about where to go when they need help. This change in dynamics has freed up a lot of time for me to either rest or to focus on more important activities. 

2. Travel

As an attorney licensed in PA, NY, and NJ, one of my favorite things to do is to leave PA, NY, and NJ. I have to force myself to do fun activities like traveling because my instinct is to be productive. 

I plan vacations and travel excursions well in advance so that the trip is already paid for and the dates are already blocked on my calendar. Those vacations are always time well spent. 

Every time I take time off, do some sightseeing, try new cuisines, etc., I emerge lighter, more energetic, and more ready to be productive.

3. Having a Team

I’ve learned that I can’t do everything myself. There are too many moving parts, I’m not an expert in everything, and I only have so many hours a day. To boost the company’s productivity, I have hired employees who can help me carry the load. Management comes with challenges, but it just makes sense that the company is more productive when there are more producers.

The Advice

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

Maintain friendships, not just colleagues. Socialize instead of networking. Pursue a hobby just for the fun of it. Do the things that bring you joy. Take time off to do something unproductive that has no bearing on your professional career. Don’t do it just to be more productive when you return to work. Take time off to remind yourself that you are more than what you do. 

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

1. Being Entrepreneurial Doesn’t Necessarily Mean Reinventing the Wheel

I’ve come to realize that there are some aspects of the Big Law business model that work well. Those firms stay in business for a long time and pay their employees top dollar. It would have been easier to start with a model that works rather than creating a model from scratch and figuring out how to make it work.

2. Watch Your Spending

Be conservative with your spending initially, even if you are convinced your business will be successful. I bought many things in the first year that I did not need, and I could have used that money in year two when my revenue was not as high as I had projected.

3. Know Who Your Ideal Client Is

Tailor everything you do – from where you advertise, to pricing decisions, to the services you provide – to that specific persona, even if it means losing out on business in the short term. In the long run, narrowing your focus will create a more successful company and save time, money, and energy. 

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