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5 Things I Learned During My First Year of Entrepreneurship

We recently celebrated the first anniversary of Counterweight Private Wealth. Launching a new firm has been amazing but, candidly, it has also had its share of challenges.

This important milestone has encouraged me to spend significant time reflecting on what went well, what didn’t, and some things that I never expected. Here are the 4 most significant observations I’ve had in my first year of entrepreneurship.


Observation #1: Entrepreneurship Is Much More Glamourous from The Outside

The word entrepreneur sounds so glamorous to many (myself included). The thought of building a business, developing a team, being your own boss, and forging your own path are enticing and exciting.

In my former job, I thought I was an entrepreneur and genuinely believed it. In retrospect, I wasn’t. At best, I had some flexibility in my income potential based on how I wanted to conduct business. But that’s not true entrepreneurship.

What I have realized is the “glamorous” aspects of being an entrepreneur take a backseat to the daily grind. In my experience, an entrepreneur is mostly a bricklayer, building the vision one small brick at a time.

No accolades, no fanfare. . . Just putting in the daily work, often when nobody is there to see it, with a forward vision that one day it will grow into something special.

It has made me appreciate how difficult it must be for high-growth startups to execute well.  It’s also helped me realize why so many high-growth startups who grow too fast are a mess internally.

Entrepreneurship takes:

  • Fortitude
  • Consistency
  • Humility
  • Patience
  • Tenacity
  • Vision
  • Grit

I’m still learning that I need A LOT more of each.


Observation #2: Relationships Thrive on Authenticity

Business is all about relationships, and true relationships can only thrive when all parties are genuine and authentic. But can I let you in on a HUGE pet peeve of mine?

Unfortunately (in my opinion) my industry is peppered with people who are more focused on the IMAGE they present rather than authentically being themselves. I’ve had people go as far as to say that I would not have any success unless I:

  • Drove a BMW or Mercedes
  • Dressed differently
  • Was clean shaven
  • Acted and spoke a certain way

I’ve also heard TERRIBLE advice that I should never show any weakness or lack of knowledge. Essentially, I should pretend to know everything or else a client won’t see me as a professional. I could tell story after story of how this garbage has been propagandized throughout my career.

I find that people simply want authenticity, in fact, I believe we humans crave it. I enjoy surrounding myself with other AUTHENTIC people.  I love the fact that we all have differences, we have flaws and insecurities, we don’t know everything, and we can be open about who we are.

Strong relationships have a high degree of authenticity. And guess what authenticity breeds? TRUST.

I have found that our clients don’t care that I drive a pickup truck or that I don’t wear ties. They appreciate that I’m a genuine person who isn’t trying to portray a certain image. I don’t pretend to be someone I am not.

They are much more interested in whether I am wholeheartedly dedicated to them rather than the image I try to present.


Observation #3: Surround Yourself with the Right People

It’s well documented that a great team can accomplish more than the sum of its individual parts. I’ve also found that having a team with a unified vision and selfless mindset is unstoppable! Candidly, I’m not the best leader and there are still many ways I need to grow. But, being surrounded by an incredible team is empowering.

The individuals on our team are selfless, genuine, empathetic, and driven. They each feel comfortable voicing candid feedback while having immense respect for each other. They have an unwavering commitment to enhance how we serve our clients and their families.

There are no egos. Each member willingly defers to the other’s strengths. They realize that each of us are gifted differently and by allowing others to use their gifts, we can deliver on goal of creating a fantastic experience to each of our clients.

I’m humbled because I simply don’t deserve to be supported by such a remarkable group. Be INTENTIONAL about who you surround yourself with.


Observation #4: Patience in Business is Hard . . . Like Really Hard!

Oddly, this is one my most challenging traits in business. By nature, I’m generally a patient person (though my wife may disagree). If you were to observe my personal relationships and my parenting style, I believe you would come to the same conclusion.

But in business? Wow, that’s a different story. I find myself extremely impatient when things don’t happen on a timeline I feel they should.

It’s somewhat like a long road trip. There’s a breathtaking destination at the end, but it will take some time to navigate the journey (though I’d rather run every red light and bulldoze through every detour).

At Counterweight Private Wealth, our long-term vision is exciting, so I want to get there as quickly as possible. It’s incredibly tempting for me to shortcut the process. Having the patience to not skip ahead of important foundational steps is one of the most challenging aspects I’ve faced.

While it may seem like an oxymoron, I find that having both patience and speed of execution is key to building any entrepreneurial endeavor. Finding the right balance of each has been difficult.


Observation #5: Trials Produce Endurance

“Count it all joy, my brothers, when you meet trials of various kinds, for you know that the testing of your faith produces steadfastness.” – James 1:2-3

We have all faced trials at different points in our lives.  I found in my younger years that it was hard to appreciate them. The lessons they taught were often dwarfed by their discomfort.

However, as I’ve matured (and some may argue this), I’ve grown to appreciate adversity.

I now realize how valuable trials are.  They build character.  They produce steadfastness.  They build endurance.

Endurance is an amazing trait, particularly within the human body. In 2010 I ran a marathon (my first and only by the way).  Before I started training, the thought of running 26 miles seemed unfathomable. But an amazing phenomenon happened throughout the process. The daily discomfort and adversity I subjected myself to in training had an incredible effect . . . It built endurance.

My entrepreneurial journey has been remarkably similar. While the launch of Counterweight a year ago has been a wonderful success and we exceeded my expectations, it came with its fair share of trials.

The adversity brought by trials is hard and uncomfortable. Yet, I’m overwhelmingly thankful for them. I don’t know what trials are in my future.  But I plan to embrace the lessons they teach, the character they build, and the steadfastness needed to endure them.

Counterweight Private Wealth is a Registered Investment Advisor (RIA) with the Securities and Exchange Commission (SEC) with its principal offices in Raleigh, NC and Wilmington, NC. Registration of an investment adviser does not imply any specific level of skill or training and does not constitute an endorsement of the firm by the Commission. Counterweight Private Wealth only transacts business in states in which it is properly registered or is excluded or exempted from registration. A copy of Counterweight Private Wealth’s current written disclosure brochure filed with the SEC which discusses among other things, its business practices, services, and fees, is available through the SEC’s website at:

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