A Founder’s Journey Requires Understanding How To Scale With Rashida Gayle

A Founder’s Journey Requires Understanding How To Scale With Rashida Gayle

VENTEUR spoke with Rashida Gayle, founder of several businesses focusing on marketing, talent representation, content, digital media, and business strategy, about her entrepreneurial journey. Gayle has secured her clients' multi-million dollar deals with behemoths such as Pepsi, Reebok, and Marriott. 

Gayle recently founded Twenty Six Entertainment, a sports and entertainment agency. Since its inception, she has diversified and nearly doubled her portfolio, catapulting into the entertainment, influencer, and brand space. Before launching Twenty Six Entertainment, she was Vice President of Talent Marketing at GSE Worldwide. While there, she became the first black and only woman to independently represent NFL and MLS players, according to NFLPA data.

Gayle is the co-founder of Bloom, an organization that caters to the new femme archetype: C-suite women, earning more than their counterparts and becoming firsts and influencers in their fields. She is also a board member of the Sports Academy Advisory Council and serves as a mentor to young women who aim to achieve in their respective fields. 

The Journey

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

I've learned that I'm human and, like everyone else–everyone has fears and voices in their heads that hold them back; for better or worse, no one is immune to that. 

But to succeed, particularly as an entrepreneur, you must overcome that fear and cycle of negative thoughts. 

You have to do the work and do it every day. 

That day-to-day mindset and practice allow me to be a better leader that's not only productive but empathetic at the same time. 

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

Yes, it can get lonely at times – not because you're alone, but because you have many decisions to make on your own. 

I have a business partner, so I have support–but at the end of the day, the pressure falls on me to make the right decisions and further the company's success. And, particularly at the beginning of an entrepreneurial journey, everything is trial and error. 

Something that worked for one entrepreneur may not work for another. 

But you must remember that you are the best executor of your vision. You have to embrace that and use it to your advantage.

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

I'm a woman and I think we're all born with intuition. But morality and integrity usually go hand-in-hand with your intuitive feelings, and staying true to who I am is where intuition plays a part in my life and business. I've found a balance between trusting my gut and getting various perspectives to weigh in on important decisions; combining the two is more important than either side of that coin.

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? 

For a while, my professional life was the only portion of my life that I was actively working on. I was doing what I could daily, ensuring my business was front and center 100% of the time. But before I turned 30, I realized I didn't feel fulfilled regardless of that hyper focus. 

So when I turned 30, I started to incorporate lifestyle habits that aligned with the person I wanted to be holistically and the life I wanted to live. I started daily and nightly routines, exercising more regularly, prioritizing time with family and friends, and more. 

Ultimately, it's a domino effect and has made me feel better and more fulfilled.

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

Every day, the employees build the business. Everyone contributes and gets to contribute at a high level. When the pressure gets hot, you're who it falls on.

Rashida Gayle

The Mistakes

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

Well, in my opinion, I haven't made any mistakes, All of the choices that didn't turn out the way I planned were just opportunities to learn a lesson. 

In most of those scenarios, they were lessons that have led me to be a better leader and opened my mind to new things. The more you operate as an entrepreneur, the more you learn that the only mistake you can make is not being open-minded and going after your dreams.

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?

This is a great question! My three things are: 

1. Appreciating Who They Hire

Ultimately, it's not what they can give us but what we can provide them. So, therefore, I try my best to give my employees as much as they give me, if not more. 

2. Overlooking the Necessity of Patience

We want things now, and we want that bottom line to move, but that's unrealistic. So instead, we should slow down and enjoy, appreciate and learn from every moment. 

3. Reminding Themselves of the Value of Others

We always focus on networking but sometimes forget that we're a network. It's essential to add value to others. This can be hard at the beginning of an entrepreneurial journey, but it shouldn't be overlooked. 

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

Three obstacles I've faced include:

1. Barriers of Entry  Access to Capital

Getting access to capital, especially as a black woman is tough. It's a lot more available today, but still tricky in its own right. Further, something I've gotten better at over the years is understanding how to use that capital and those resources when I get them. Getting it is half the battle, using it wisely is the other half.

2. The Hiring and Firing Process

Finding, hiring, and retaining stellar employees, particularly during the great resignation, was tough. That said, regardless of the economy and the industry, I still find it extremely hard to find quality talent willing to put in work and come in with a positive, can-do attitude.

3. Scalability

Understanding how to scale, particularly in a relationship-based business. This is still something I'm learning to do effectively.

The Advice

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

I recommend looking within yourself and prioritizing the person you want to be daily. If you do that, you will become that person. 

For example, if you're working 60 hours a week and realize 40 hours is better for you, you're accountable for that. In that scenario, you're prioritizing money over health, and that's your choice. We all get to make choices, and making those choices starts from within.

What three critical pieces of advice would have made your entrepreneurial journey more manageable, and why?

It'll never be easy! 

But, if I could go back and tell myself these things, I think I would've been better prepared: 

1. Acknowledge the Good and the Bad

Highlight how difficult it is to be an entrepreneur and the daily ups and downs when you're living it. I'm not alone. It's a part of the journey, so don't give up. 

2. Recognize People Who Are Only Interested in Taking, and Who Aren’t Giving

Understanding that people need to work for credibility and that you may need to sift through some who want to take more than they give. But ultimately, you need to be smart about how much you contribute to others if they need to be aligned with your business and its objectives. 

3. Secure Payment From Clients

What to do if your clients don't pay on time? 

You could have a contract and a great relationship, but what happens when they don't pay you? It would help if you put parameters and soft cushions around your cash flow and ensure you have the right third-party relationships to position yourself for success (I have a fantastic accountant and use Xero daily to ensure I'm set from a financial perspective).

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