Jimi Tele of Chekmate: Why It Is Essential That We Reform Diversity & Inclusion Policies

Jilea Hemmings
Feb 14 · 9 min read

Never forget your why. It is slightly insane to wake up one day and decide to launch a company; it really is. There are so many easier walks of life and career paths a person can embark on. That’s why purpose has to be embedded in the foundation; otherwise, you will give up because there’s something less demanding that you could do.

I had the distinct pleasure of interviewing Jimi Tele, Founder and CEO of Chekmate.

A high-performing business development executive and rising international entrepreneur with 8+ years experience in business & tech, Jimi has specialized expertise in location data intelligence, global business, cross-culture collaboration, B2B growth, and startups. As a global citizen with British-Nigerian heritage, he has advised top fortune 1000 companies on collaborating with African government conglomerates to explore projects across the science, engineering, tech, agriculture, and construction landscape. He is now the founder and CEO of Chekmate, Inc., a dating marketplace centered on promoting safe real-time communication and human connection. He was a decorated England triple jumper on a full university scholarship for track and field when his Olympic dreams were dashed due to traumatic brain injury. After overcoming adversity in his own life, Jimi is passionate about mental health advocacy and encouraging the next generation to fearlessly fulfill their dreams no matter the circumstances. From starting blocks to startups, catch him if you can!

Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path?

I was a decorated track athlete when my Olympic dreams were abruptly destroyed due to a traumatic brain injury. I thought my future was over for a while, but through faith, support, and finding the strength to persevere, I retrained myself how to think, feel, and focus from scratch. I drew from my resilience and consistent ability to overcome obstacles by making a promise to myself that if I couldn’t become an Olympic champion, I would become a champion entrepreneur.

During my transition to business, I discovered facilitating connections is a passion of mine. I’m a British native with Nigerian heritage that currently resides in the United States. My connection to three different regions of the globe and their diverse cultures have provided me with a unique lived experience. That experience allowed me to begin connecting conglomerates to new countries on a macro-level, which eventually turned into connecting people on a micro-level via Chekmate.

As you can tell, I genuinely thrive and excel in high stake, high-pressure, global arenas. That’s how I ended up finding my lane in the fast-paced entrepreneurial tech scene.

Can you share the most interesting story that happened to you since you began your career?

I was in dire need to expand the development team to meet our product objectives and goals. For months, I had been looking for someone that would be a good fit for our company culture. Unfortunately, through the years, we had issues with developer integrity; hence, I was hypersensitive regarding finding the perfect person. One night after a long day of work in the city, I ordered a Lyft to head home. Usually, I keep to myself, as I like to gather my thoughts, but that day was different. I started talking to the driver. He told me he was driving for personal reasons and that he was actually a software engineer. The languages he codes, ironically, were precisely what we were looking for. I took his resume and excitedly sent it to the team! It was the icing on that cake when two of the team members already knew him and attested to his stellar performance, literally describing him as a “superstar.” Since then, the rest has been history. He has been with us for over a year now, and I’m honored to have the opportunity to work with him. I’m a big believer in everything happening for a reason, both lessons and blessings.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I was abundantly optimistic about materializing my vision for the company. I wanted to ship the product as fast as possible; perhaps, the drive for speed comes from the track star within me. I initially outsourced company development overseas, thinking that all I needed was a V1 product; however, I was grossly mistaken on multiple fronts. All of the comments in the code were in a foreign language. The code also became redundant. At the time, I obviously didn’t find the situation funny, but now I chuckle at how my enthusiasm and passion overshadowed the process. Today, I embrace quality and efficiency while never sacrificing either for speed. I’ve learned not to skip steps and recognize short-term objectives must align with long term goals. Much of my journey has been trial and error, but having a process is imperative. The negative experiences are just as important as the positive ones. I like to believe everything is a learning lesson and contributes to my development as the best possible entrepreneur.

Can you share three reasons with our readers about why it’s really important for a business to have a diverse executive team?

I think it is paramount for a company to be diverse from its inception. Companies can’t afford for diversity to be an afterthought.

  1. Company culture is improved when the leadership team is a reflection of the employees. The leadership’s ability to relate to their employees beyond the company’s goals allows for a deeper level of comradery, ultimately resulting in a healthier work-place environment.
  2. The combination of different cultures and backgrounds should be the bloodline of a company. Having a diverse executive team allows you to have a broader reach and unlock more diverse customers, including customers that you may have overlooked. We live in a diverse world with diverse consumers. Diverse companies can perform better because they can understand a multitude of perspectives, tap into different markets, and make better decisions that accurately reflect the society we live in.
  3. Put simply, diversity is the right thing to do on multiple levels. Diverse companies are 87% better at decision making and 1.4 times more likely to increase revenue. Racially and ethnically diverse companies are proven to perform 35% better.

More broadly can you describe how this can have an effect on our culture?

As society continues to develop into a more racially diverse polity, those that fail to reflect the United States demographic makeup face the possibility of getting left behind. Not only are diverse voices no longer being left behind, they’re beginning to determine whether or not consumers will continue to invest in the brand.

In the era of incredible social unrest, a company’s stance on social issues has a tremendous impact on consumer engagement and brand loyalty. Those who are silent are being boycotted. It is no longer acceptable to be a bystander. People want companies to use their influence to speak up and actively work to create a more equitable world.

Can you recommend three things the community/society/the industry can do help address the root of the diversity issues in executive leadership?

When you’re Black in tech, the level of scrutiny is amplified because of your skin color. I’ve walked into numerous rooms where my expertise is questioned. It’s almost as though it’s incomprehensible for me, a Black, dark-skinned, immigrant man, to exist here.

  1. Diversify the capitalization table
  2. Address paternalism in the industry.
  3. Fund more minority-owned companies.

How do you define “Leadership”? Can you explain what you mean or give an example?

There’s a difference between being a boss and a leader. A boss commands with little support, whereas a leader leads by example. You have to get your hands dirty. I’ve always said I’m not too good to take out the trash. When people describe their best/favorite boss and their worst/least favorite, they seldom describe competency but instead interpersonal skills and interactions. You have to treat people with respect and meet them halfway. Excellent leadership encompasses honor, compassion, and empathy. I believe it’s important to treat the janitor with the same respect as the executives; integrity is doing the right thing when nobody’s looking. My goal as a leader is to uplift and empower every person I interact with by assisting them to be the best possible version of themself in order to reach their fullest potential.

What are your “5 things I wish someone told me when I first started” and why. Please share a story or example for each.

  1. Fall in love with the process, so you never let a destination or thing solely define your success and happiness. I used to believe that I would hit the pinnacle of my success within a relatively short period of time. When I hit a certain age and wasn’t where I wanted to be, I started to believe I had failed. In reality, as a “type A” individual or someone with a go-getter mentality, you’ll almost always be chasing some new form of success. Thus, it’s important to remember that success is the journey and determination, not the destination.
  2. Your productivity doesn’t define you or your self worth. There is always something that needs to be done. There is always something you could have, should have, or would have done if you had more time. Rest is just as important to success as productivity.
  3. Minorities have to work twice as hard. Naively, as a triple minority, I used to think it was an equal playing field, and doors would open if you just worked hard. Unfortunately, once I was in the space, I ran into many executives that treated me with paternalism, offering the bare minimum or treating me as if I’m looking for a handout. Ironically, some of the people occupying the space didn’t necessarily get there via their own merit or expertise but inherited a legacy that minorities historically haven’t had access to.
  4. Never forget your why. It is slightly insane to wake up one day and decide to launch a company; it really is. There are so many easier walks of life and career paths a person can embark on. That’s why purpose has to be embedded in the foundation; otherwise, you will give up because there’s something less demanding that you could do.
  5. Learn to harmonize your grind with your grace. The grind is glorified in society. However, it’s essential to acknowledge how far you have come and embrace the progress you’ve made along the way. I’m a high performer by design due to my athletic background, but giving yourself and the team grace when things don’t go right is critical to prevent burn out.

You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

I would love to create a movement grounded in individuals finding their life purpose. I think it’s important to know your purpose and define yourself for yourself; before the world defines you. You are your own Utopia, and you can bring your universe with you everywhere you go. Productivity and money shouldn’t be the sole premise of your identity; it’s not sustainable, and I speak from experience.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“What if you fall? Oh, but my darling what if you fly?” is a quote by Erin Hanson. It helps me make it through my worst days. It reminds me that I may be faced with hardships and challenges, but I must continue to follow my dreams for one day, it will all be worth it. My focus and faith propels me to keep persevering through even the most tumultuous conditions. If you’ve been blessed with a vision, I feel it’s your fiduciary responsibility to share it with the world.

Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might just see this, especially if we tag them. :-)

Rihanna, I admire her unwavering integrity. She is always giving back and doing the right thing, even when it may not benefit her. She is inspirational, as a fellow Black immigrant who has been able to navigate and pioneer her own path not only an artist, but a thought leader, business executive, and philanthropist. I have an enormous amount of respect for dynamic individuals who have overcome adversity, yet remain abundantly humble and rooted in their values.

How can our readers follow you on social media?

Instagram: @Jimitele

Twitter: @Jimitele

Linkedin: Jimi Tele

This was very meaningful, thank you so much!

About the Interviewer: Jilea Hemmings is a staunch believer in the power of entrepreneurship. A successful career revamping Fortune 500 companies was not enough for her entrepreneurial spirit, so Jilea began focusing her passion in startups. She has successfully built 6 startups to date. Her passion for entrepreneurship continues to flourish with the development of Stretchy Hair Care, focusing on relieving the pain associated with detangling and styling natural black hair. For far too long, people with tender heads have suffered in pain. Until now.

Authority Magazine

Leadership Lessons from Authorities in Business, Pop Culture, Wellness, Social Impact, and Tech. We use interviews to draw out stories that are both empowering and actionable.

Jilea Hemmings

Written by

Founder Nourish + Bloom Market | Stretchy Hair Care I Author I Speaker I Eshe Consulting I Advocate For Diversity In Beauty

Authority Magazine

Leadership Lessons from Authorities in Business, Pop Culture, Wellness, Social Impact, and Tech. We use interviews to draw out stories that are both empowering and actionable.

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