Calvin Williams Jr. of FreemanCapital: “The fourth thing that is really critical to riding the highs and lows, is a longer horizon of success”

…The fourth thing that is really critical to riding the highs and lows, is a longer horizon of success. We live in micro theme culture where everything is in small bites. But success still takes time. We hear about overnight successes and we can compare ourselves, and that can become very much of a demotivator, […]

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…The fourth thing that is really critical to riding the highs and lows, is a longer horizon of success. We live in micro theme culture where everything is in small bites. But success still takes time. We hear about overnight successes and we can compare ourselves, and that can become very much of a demotivator, but having a vision to what you want to be, and giving yourself time to get there is going to help you stay balanced, knowing that I am okay if my journey takes longer than someone else.

Being a founder, entrepreneur, or business owner can have many exciting and thrilling moments. But it is also punctuated with periods of doubt, slump, and anxiety. So how does one successfully and healthily ride the highs and lows of Entrepreneurship? In this series, called “How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur” we are talking to successful entrepreneurs who can share stories from their experience. I had the pleasure of interviewing Calvin Williams Jr.

Mr. Calvin F. Williams, Jr. is the first African American owner of an automated wealth management platform for retail customers registered with the SEC. As the CEO and Founder of, he aims to close the wealth gap in overlooked communities across the country through increasing access to financial planning, investment management, and financial education.

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?

Answer: My backstory really begins first with my family. My mother was an entrepreneur and went on to become the top 1% of realtors in the nation at Merrill Lynch. My father always had entrepreneurial endeavors as well, so they both exposed me to entrepreneurship at a very young age, whether cutting grass or building websites in middle school for construction firms, churches, small businesses.

I bounced back and forth between private school and public school, which taught me a lot about how to build relationships. I often experienced being one of three black people in the whole school in private school, which was a very unique experience. I went to North Carolina A&T for undergrad, and that’s really where I began to grow and develop. I joined a fraternity in my freshman year, which was a major move, as I was the 12th person to become a member of my chapter within its 70-year history. I later became student body president and launched my own web development firm as well.

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

Answer: When Freeman Capital launched, we provided diverse investments for diverse people as an asset diversification play with forex and futures. But the interesting thing is that our customers did not care, or they were more interested in working with us as a brand than they were about where we put their money.

That really opened up the opportunity of being more holistic, and not just focusing on being a diversification play, but also look into equities and financial wellness to truly solve real customer’s everyday problems. It led us to concept a personalized financial planning platform to account for the income gap, the wealth gap, and the financial literacy gap — gaps that people of color need to overcome to build wealth. This empowered us to create financial planning around mass hyper-personalization, through automation, and a methodology that allows us to reach more people on scale.

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

Answer: I think that I had some natural characteristics, for example, I’m comfortable with risk, setting a vision, and working in environments that are ambiguous. And those are all needed to be an entrepreneur. But I don’t actually think anyone is a natural-born entrepreneur, I think that entrepreneurship is a skill, like everything else in this world. The question is, do you want to work to develop that skill? The exposure of my parents, being an entrepreneur, and me starting my own businesses early on, I learned a lot of lessons. So, entrepreneurship is a way for me to grow and develop into my life’s purpose. But I wasn’t born into it, I had to work every day to develop the skills, mindset, and leadership qualities.

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?

Answer: Of course!. There were several people who inspired me throughout this whole journey.

It starts with my great grandparents and the fact that they were able to get a second property in Washington DC during segregation, and that began to pass down through our families. My mother’s entrepreneurial success was a huge inspiration as well. I also read a book when I was 14, or 15, called Silicon Valley Millionaires, which tells the stories of how startups in Silicon Valley grew and scaled. Lastly, one of the most influential books of my life is Think and Grow Rich, a black choice by Dennis Kimbro. And what that book did is that it showed me that there were black people who were successful and throughout time, their stories have not been told by mainstream media. But reading their stories, as a teenager showed me that if they could do it, with segregation, slavery, and overt oppression, and that I could be drastically successful as well with a much more equal playing field than they ever had. I still lean back on those stories as well, and they still continue to inspire me day by day.

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

Answer: I think that one of the biggest things that make our company stand out is our focus on building wealth for black people. We are cognizant of the major challenges that systemically exist in our country. And we see the silver lining of the opportunities that are thereby giving people the access to education and tools that they need to grow and build their wealth. And we have seen it with several people who have been teachers, doctors, policemen, entrepreneurs, or whatever their walk in life. They’ve been able to take our advice and platform and improve their financial wellbeing. There was one gentleman who was doing what he thought he should do. He saved up 10K for his house downpayment and wanted to invest it in the stock market to grow it more. And this is right before the COVID-19 hit. Given his objective, it was less about market timing, but about being strategic with your investments. By working with one of our CFPs, we helped him learn and figure out the right place to invest. He ended up moving the 10k house down payment into a conservative investment, and reposition his portfolio. The market did ultimately crash, and he was able to protect his downpayment, and add more. Now, he’s in his house, which is one of the biggest ways to build generational wealth. We also have helped folk who are trying to figure out what is their path and build wealth, give them the specific steps to help them double, sometimes even triple their net worth in a year.

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?

Answer: The first characteristic is being a servant leader. Understanding that to create a climate for people to be their best, I have to balance setting a firm direction with being inclusive. The second is being aggressively patient, meaning that there are times when I have to be patient, because it’s for our best interest, and others when I have to be aggressive and to reach our goals. The third trait is around discernment. Because there’s so much data that you get as a business leader, and you have to be able to process and understand how to consume feedback from your teams, investors, and advisors to know what products to roll out, what markets and what business metrics will ultimately determine success.

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?

Answer: As an entrepreneur, you have to think forward and I can’t spend time thinking about the advice that I wish I never followed. I take responsibility for my actions, it doesn’t matter if it was my idea or someone else’s idea. I did the action. So, I focus on what lessons I have to learn and I literally can’t remember the advice that I wish I never followed. I learn from everything. Either I win or I learn.

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?

Answer: One thing we believe, and still work towards daily is creating a culture that has a strategic objective, that everyone can align their work towards. This is especially hard when you’re doing a startup because you will want to tackle every opportunity quickly to grow faster. So as CEO, I have to look out a month in advance and then give my team their objectives so they don’t feel overwhelmed.

What would you advise other business leaders to do in order to build trust, credibility, and Authority in their industry?

Answer: In our present culture, everyone wants to be a celebrity, coach, influencer, guru, etc. And we are seeing so many people who have a following, and appear to be very successful. But to build credibility and trust, there needs to be something there beyond the following. The best way to do that is to build something that is real, with real value to people. By doing that, you will have trust, credibility, and authority.

Can you help articulate why doing that is essential today?

Answer: Authenticity is what stands out more than anything in this tech and digital world. In order to build trust, credibility, and authority, your product and essence must be rooted in the core DNA of your company and the real people’s problems you are trying to solve.

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?

Answer: Speaking for myself, there were times when I was too aggressive, creating artificial deadlines vs spending the time to get things done right, which created burnout and people get overwhelmed. I have chased too many projects at one time, which ultimately lead to fatigue and lack of focus across the organization. Also, a common mistake is not being focused on key performance metrics and growth. If a business is not growing, it’s dying. Lastly, is not providing clarity around team roles and company rules can lead to confusion and overlap of resources.

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”?

Answer: As a CEO or an entrepreneur, it is extremely critical to know that you will experience extreme highs and lows because the high moments happen when your vision is starting to become realized. The lows come when your vision breaks or doesn’t happen. It could be a deal falls through, you run out of money, the customer cancels, etc. This is very different from a regular job because even though you may have highs and lows, there is a balance within the company that will most likely keep the company from failing. So, to succeed as an entrepreneur, you have to learn to be more consistent. I trained myself as an entrepreneur that when those high moments come, I should enjoy them. It’s validation that I’m headed in the right direction. But I also must stay level, because the business exists off the emotional maturity and development of its leader. So, if I don’t stay emotionally balanced, there will be bad mood swings, which my team will feel. That doesn’t happen in a regular job, which is one of the biggest differences.

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.

Answer: Sure!. The first time we got a customer that was not a friend, family member or referral, was a really big win for me. Even more, they were happy with our service which took me to an emotional high. This person found our service on their own, signed up, met with a planner, got their financial wellness plan, and saw results. It confirmed to me that our product and service were working and we had an opportunity to reach and help people. I tried to stay as level as I could as I know, like in any business, there would be more challenges. But, I did enjoy that moment and celebrate that win.

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.

Answer: There was a moment where we had to pivot our business and product, and the funding got very low. I had to call each team member and tell them that I was not going to be able to pay them and that I had to put them on break. And afterward, I felt like such a failure. I knew that these people were depending on Freeman to help provide the cash flow, and my lack of management and preparation caught them all by surprise. The day I missed payroll is when they first found out, which was horrible for so many reasons. It decreased their trust in me as a leader, and it decreased my own trust in myself. I vowed to never let that happen again.

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

Answer: I spent 3–4 months putting a system and financial controls in place. I firmly believe that when you do the right things behind closed doors you will manifest positive outcomes without missing a mark. And in times where we have to prepare to cut back, we’ve generally always gotten more funding that has kept us going.

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.

Answer: The number one thing that you need to ride the emotions is a great supporting team. I was going through some personal problems that were weighing on me, I was not bringing my best self to work. When you work with small teams you begin to develop a close bond, and they can notice differences in you that you may not see yourself. They were instantly there for me and made sure we kept on track with our projects.

The second thing that you need to have when you’re writing these highs and lows, is clarity of your own vision. As a startup, there may be times where the funding will dry up, or conversely, you’ll get more funding and more opportunities. Potential investors, stakeholders, peers, etc., will come to you and share what they think you should be doing. But having a really clear vision can help us keep the main thing the main thing, and chart the path forward.

The third thing that you need is an accountability partner or coach. As CEO, you are taking in so much data, and have to be intentional about how you communicate and advise others. You have to balance being a leader for your team, as well as being vulnerable to a degree, with your team and investors. You have to create a safe space to share what’s going on in your business without unloading and burdening the people around you with what’s going on in your head. So having a coach or a therapist who has taken other people through this journey multiple times, is a great way to successfully ride the highs and lows.

The fourth thing that is really critical to riding the highs and lows, is a longer horizon of success. We live in micro theme culture where everything is in small bites. But success still takes time. We hear about overnight successes and we can compare ourselves, and that can become very much of a demotivator, but having a vision to what you want to be, and giving yourself time to get there is going to help you stay balanced, knowing that I am okay if my journey takes longer than someone else.

The fifth thing is supportive home life. Being an entrepreneur is very challenging, it’s a totally different walk of life than what isn’t normal to the majority of the country. So having friends and family and a community around you that can make you feel safe, loved, and supported is going to help you to celebrate those highs and help you to bounce back from those lows

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?

Answer: Resilience is the ability to take complete and utter rejection, and find a way to take one more step forward. And I think that the characteristics of resilient people are people that have a firm belief in either themself, their purpose, or what they’re working on. When you have that, it gives you the ability to deal with the worst parts of this journey, and bounce back with measurable steps.

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

Answer: I had a somewhat bad speech impediment when I was growing up and had to continue to learn how to communicate in a way so that I could be understood. In school, kids made fun of me, which made me feel like I couldn’t talk or read in classrooms. I dealt with all that emotional burden and still decided that I was going to be successful. I became Homecoming King in high school, gave my high school graduation speech, as well as the introduction to the keynote speaker. I also became student body president at North Carolina A&T, and now speak all of the time in public and in media outlets. So my resiliency led me to first believe that I can do it, and then conquer it.

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

Answer: I focus less on positive, but more on being realistic with optimism. What keeps me optimistic in these times is defining and focusing on the vision.

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.

Answer: It is motivating and inspiring when I get confirmation of the vision realized, is the continued support and encouragement from customers, investors, employees, partners, and press. We consistently have high customer feedback scores, media that want to hear our story, and passionate team members and investors that want to take us further. I can only attribute that to our optimistic outlook and alignment on the vision. I also keep in mind the fact that, in our community, we have had highly successful black people, even in the face of systemic overt racism and prejudice. If they can be successful in their time, then I believe that I can be successful in mind and I’m not even dealing with those same types of challenges. That gives me the hope and purpose that I use to guide my team.

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?

Answer: Fortune favors the bold.

I love that quote, and it’s something that I always leaned into when I first started the business when I became the first black-owned wealth management platform that was automated and registered by the SEC or achieving other stretch goals. It just is a really simple quote that helps me to keep moving forward.

How can our readers further follow you online?





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

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