Inspirational Black Men In Tech: Jimi Tele of Chekmate On The Five Things You Need To Know In Order To Create A Very Successful Tech Company

An Interview With Jamie Hemmings

Have a WOW mentality! I call it the WOW mentality because it means “with or without” you have to have the discernment to keep going and keep creating. This is critical because, at the beginning of your journey, no one will care about what your building as much as you. There will be a lot of negative people that will project their failures and insecurities on to you. People will tell you what you can and can’t do. Having a WOW mentality will prevent the negativity from corrupting your vision and allow those who truly align with your mission to join you.

As a part of my series about “Lessons From Inspirational Black Men In Tech,” I had the pleasure of interviewing Jimi Tele, a high-performing business development executive and rising international entrepreneur with specialized expertise in location data, global business, cross-culture collaboration, B2B growth, and startups. He is now the founder and CEO of Chekmate, Inc., a dating marketplace centered on promoting safe real-time communication and human connection. The British-Nigerian 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 joining us in this interview series! Before we dive in, our readers would love to learn a bit more about you. Can you tell us a story about what brought you to this specific career path?

I was blessed to obtain a scholarship to Millfield School. The boarding school represented my opportunity to create a better life for myself and, eventually, my family. After years of extensive training while at Millfield, I became a top-ranked triple-jump prospect. In the summer of 2010, I was ranked number one in the United Kingdom for my age group. Upon graduating high school, I received more than twenty-five scholarship offers to various American universities. To fulfill my dreams, I came to the US alone with no family or friends. I would eventually go on to be a six-time conference champion and break the Atlantic 10 Conference Championship record. I looked forward to my moment at the World Championship.

I was a decorated track athlete when my Olympic dreams were abruptly destroyed. During a training session, I was struck on the head with a 25lb medicine ball. I assumed I endured a simple concussion. I persevered through the injury, maintaining top performances and medals for several months. However, the injury’s impact continued to worsen, transitioning from debilitating migraines to five convulsions a day. For almost a year, I was in and out of the hospital. Upon further review, I had sustained a traumatic brain injury that halted my international athletic journey. In a foreign country, I was unfamiliar with the United States healthcare system and had a difficult time navigating through it alone. I experienced severe depression and didn’t know which way to turn. My close friends from England didn’t know why I disappeared from sports, and they were anticipating my return. I was ashamed. It was hard watching my friends, the ones I used to train with, on television at the Olympics, and traveling the world. I wanted to be there. For a while, I thought my future was over, but through faith, support, and finding the strength to persevere, I retrained myself how to think, feel, and focus from scratch. During my recovery, I confronted the need to reset my goals. 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 athlete, I would be an Olympic entrepreneur.

After stabilizing my condition and being seizure-free for months, I felt compelled to transition from my identity as a student-athlete to an entrepreneur. I decided that it was time to put my business management and economics degree to use, while also making a difference in the world by creating a safer dating environment. Every day, I ferociously embody this as I set on a mission to alleviate loneliness across generations. My expertise in location data intelligence, combined with my lived experience of loneliness during my time of hardship, makes me the perfect entrepreneur to bridge the gap between online and offline interactions, the fundamental elements to what we are creating with Chekmate.

Moreover, 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 its diverse cultures have provided me with a unique lived experience. I offer a global perspective and an essential piece of social capital that most founders may not have. I’ve had the opportunity to work as a business consultant advising Fortune 1000 companies on connecting with African government conglomerates to explore projects across the science, engineering, tech, agriculture, and construction landscape. I’ve also worked as a business development advisor for a multibillion-dollar global fund specializing in large project collateralized financing with a focus on the United States and African markets. As you can tell, I genuinely thrive and excel in high stake, high-pressure, global arenas. I love challenges and being able to set the pace; this is what groomed me to find my lane in the fast-paced tech scene.

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

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 tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

I was egregiously exploited when I first started this journey. I was a Black immigrant in a foreign country who had just recovered from a traumatic brain injury. My intellect was snatched, and my time was wasted. Unfortunately, even my money was stolen. I was bullied by mentors and advisors who defrauded me using their executive tenure in fortune 500 companies as credibility. I had a close friend and “mentor” promise me that if I helped grow their company as a mentee, they’d help fund me. Once people saw my work-ethnic, excessive drive for productivity, and dogged tenacity to achieve, I became a target they wanted to extort for their own gain. I probably have about 5,000 hours of stolen labor out in these corporations, and millions of dollars worth of IP contributed. The business world is so savage. It can crush you if you aren’t built to last. I learned the hard way.

For example, when I first graduated from undergraduate school, I decided to work for a startup in the tech/app industry to obtain capital and experience for my business. I believed that this was a perfect fit to balance alongside my own startup. When I started with the company, I accepted a position as an intern making $600 a month, while still living on my friends’ couch. The company’s office was in an industrial area about an hour away and not easily accessible by public transport, so I used my paycheck to pay for my Uber there and back. It was like Christmas when a coworker would drop me off at the metro or when the office catered lunch. I was often the first person in and the last person out because I was eager to learn, achieve, and make money to fund my startup. I ended up doing over 80 hours a week.

After three months, I had managed to close the biggest deal the company had ever seen. A couple months later, I was promoted directly from intern to senior sales consultant. I identified fractures in their process and built architecture, trained peers, and taught leadership how to scale. Most importantly, the data demonstrated that I not only exceeded my personal sales quota by 700%, but I met the entire sales team quota by myself. I brought in millions of users to their platform. In exchange for my labor-intensive role, the company promised me equity and adequate pay. However, my direct supervisor saw my over-performance as a threat to his position, and he made sure that my new success would not be met with full support. He constantly harassed me with late night calls, regularly used racial epithets to belittle me in front of co-workers, and refused to ensure I received the correct compensation. He even called me the N-word during a meeting and told me, “I deserve to brand my name on your chest.” The incident caused him to leave the organization, however his behavior was encouraged by the company culture. Since the company had already raised its Series A funding with my assistance, coupled with the CEO’s frustration that his best friend could no longer work for the company — they defaulted on their word and never completed my equity shares. They also decided not to renew my auto-renewed contract, despite having never been reprimanded and still holding my position as their top-performing consultant. By this point, I panicked. I had numerous breakdowns when I didn’t know how I would eat or where I was going to sleep. I would walk miles in the cold and rain suffering in silence.

However, I believe every experience, positive and negative, teaches us something. Moreover, when I was at my lowest, I reminded myself of that email sent out in college, where a woman in my alma mater was assaulted via an online dating app. I reminded myself I have a team that believes in me and trusts me to lead the way and build a legacy. I reminded myself of how painful and debilitating it is to feel lonely, and how many people I could help with our solution. My mission is so ingrained and personal that giving up was never a choice. My faith is what gives me the resilience to fall down seven times and stand up eight. I correct people when they say I’m self-made. I’m faith-made. Faith has been so fundamental to any success I have or what I’ve been able to endure. Faith and therapy are essential. They’re the two things that keep me afloat, and I’m not ashamed of that. Mental health, especially for people working in the demanding tech industry, is paramount.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

Mike Labriola of Wilson Sonsini, has made much of my success as an entrepreneur possible. I met him during my time with a start-up program. The program offered a series of presentations from experts in various fields, and Mike happened to be presenting on term sheets. After his presentation, we had a three-minute chat and really “hit it off.” At the time, I had no idea just how influential he would be to my journey. He was generous with his time and network. Not only did he make me feel comfortable, but he would provide hours of advice to me regarding how to navigate the fundraising landscape. He gave me candid feedback, which ultimately gave me the confidence to propel me forward.

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.

Ok super. Thank you for all that. Let’s now shift to the main focus of our interview. The United States is currently facing a very important self-reckoning about race, diversity, equality and inclusion. This is of course a huge topic. But briefly, can you share your view on how this crisis inexorably evolved to the boiling point that it’s at now?

I have experienced an unfathomable amount of racism throughout my life. Whether it was being called the n-word at the office or the earliest days of my childhood when students sang racially charged songs. Those are just two of the explicit examples of individual racism I’ve had to endure. Unfortunately, racism isn’t unique to me. It’s a shared experience for Black people.

Moreover, it’s a much more complex issue than individual acts of malice or discrimination. Racism is a systemic issue that’s developed over several centuries. Black people across the globe have been fighting injustice for an inconceivably long time. What’s interesting about the current moment is seeing a record amount of people protesting nationally and globally. We also see an increase in the number of protests. Typically, protests are quelled by the need for the masses to return to work. The people most vulnerable must go back to earning money in order to survive. However, with record numbers of unemployment, many people are unsure about how they’re going to pay their bills and where their next meal is coming from. Thus, they have no choice but to protest their current conditions.

This may be obvious to you, but it will be helpful to spell this out. Can you articulate to our readers a few reasons why it is so important for a business or organization 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. 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 to better serve or unlock more diverse customers that you may have overlooked. Diverse companies can perform better because they can understand different perspectives, tap into different markets, and make better decisions that accurately reflect the society we live in. Racially and ethnically diverse companies are proven to perform 35% better.

What’s more, diverse companies are 87% better at decision making and 1.4 times more likely to increase revenue. Put simply; diversity is the right thing to do. It’s important because we live in a diverse world with diverse consumers. Not to mention, diverse companies generate more revenue.

Let’s zoom out a bit and talk in more broad terms. It’s hard to be satisfied with the status quo regarding Black Men In Tech in Tech leadership. What specific changes do you think are needed to change the status quo?

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 dark-skinned immigrant Black man, to exist here. Most people I interact with resolve their racism and cognitive dissonance by attributing my success to pure luck. Hence, my personal mantra, “Do it twice, so they don’t call you lucky.” During my earliest moments, I’ve run into many young VC 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 get there via their own merit or expertise, but inherited a legacy or raised money via their intimate circle. As Black people, due to the fact that we’ve been private property longer than we’ve been able to own it, we suffer from an exponentially large wealth gap. Hence, very few of us can ask mom and dad for large lump sums of money to get started or help out when things get rough. For us, we have to fight for everything we earn. Unfortunately, adding random spurts of Black leadership to your C suite is for the optics; real change is black ownership — now let’s run the data on that Cap Table!

We’d now love to learn a bit about your company. What is the pain point that your company is helping to address?

I’m a data guy so let’s talk statistics! Fifty-three percent of Americans fabricate their dating profiles, twenty-eight of online daters have felt harassed or uncomfortable, only sixty-six percent of people on dating sites actually go on dates, and thirty-four percent of people have been deceived or catfished. The dating industry is saturated, but it’s also fragmented and unfinished. There’s a myriad of fake users and disingenuous behavior. Now more than ever, due to COVID19, people are craving a safe space to connect authentically. So we set out on a mission to alleviate loneliness across generations and enhance life’s experiences through dating both virtually and in real life. Chekmate built a catfish proof community using tech to solve the inefficiencies in the market.

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

Technology is further disconnecting people by keeping them in little bubbles online. What’s different about Chekmate is that we’re going against the grain and bridging the game between on and offline. The two should work together. I also believe our ability to be catfish proof is unique and important. We want our users to be seen and heard through voice and video interaction, so it breaks the anonymity that allows people to be malicious, harass others, and hide behind a screen. Our company encourages people to be themselves without judgment. As of right now, the industry is gamified and promotes addictive behaviors. They fail to actually benefit the lives of the users they claim to serve. Whereas, at Chekmate we believe meeting is just the beginning.

Are you working on any exciting new projects now? How do you think that will help people?

We are working on launching our Chivalry Isn’t Dead campaign. This is essentially focused on shifting the misogynistic mentality around dating while simultaneously promoting courtship. Although I love tech, I think it’s imperative that we’re using it to connect deeply. Unfortunately, many of us use technology as an escape, and eventually, it contributes to a lack of interpersonal connection and distance. As a community, we need to create a new normal, grounded in bringing people together and spreading positivity via tech.

What would you advise to another tech leader who initially went through years of successive growth, but has now reached a standstill. From your experience do you have any general advice about how to boost growth or sales and “restart their engines”?

Always audit your process and identity fractures. If you take the time to build a framework tailored to your company’s specific needs, it will be easier to audit and identify deficits later in the process. For example, integrating your KPI monitoring system into a data centric CRM will allow you to know where you are falling short. This way, you can pinpoint precisely where in the sales cycle the issue is and come up with a strategy to fix it. It’s always better to be proactive instead of reactive so you can limit the number of critical issues that could be fatal in the long run. You can’t scale anything with fractures. You’ll be spinning your wheels for months with no movement, it’s like trying to fill a gallon jug with a hole in it. Fix the engine before you add fuel.

Do you have any advice about how companies can create very high performing sales teams?

A team can only be as good as the process and framework put into place; the company foundation is crucial. Leadership needs to build a framework based on key goals and objectives, and then implement a company-wide process to achieve those goals. Having a framework and methodology will ensure that all potential fractures are identified, allowing the sales team to have a precise focus with little disruption. It is also vital for the sales team to have autonomy; autonomy sparks creativity because then they are inspired to growth hack your process and make it more efficient. Sales is an art, not a science. Give your team the tools, provide them with the formula, and empower them to paint the picture and sell.

In your specific industry what methods have you found to be most effective in order to find and attract the right customers? Can you share any stories or examples?

Since my company operates as a marketplace, our industry has an array of verticals, each with its own unique charm for attracting the right customer or client. The commonality, though, is having a robust understanding of your customer archetype. Once you know who your customer is, you can build systems that allow you to learn their values, interests, and communities on and offline. This helps formulate the best messaging and approach to reach them authentically. Combining qualitative & quantitative data into understanding the customer will allow the company not only to reach them but also to know their “why,” which humanizes the engagement.

Based on your experience, can you share 3 or 4 strategies to give your customers the best possible user experience and customer service?

I’ll answer this from an enterprise perspective by using a B2B funnel. After signing a contract, there’s a fiduciary responsibility to do what you said you would do. Even after the sale, you still have to sell, thus the acronym for a client success model I built.

S is for Success

Client success should mean using our products and services to ensure your clients achieve their desired results. Client success is relationship-based client management that places client and vendor goals at the forefront to produce a mutually beneficial goal. The best client success strategy usually results in decreased client churn. The essential purpose of client success is to make the client very successful and enhance customer lifetime value (CLTV) for your organization.

E is for Exceed Expectation

Always try to finish a project before the due date; that way, your client will entrust you with more because they are confident in your ability to deliver. Ensure that the quality of the job delivered is stellar. When you consistently exceed expectations, you gain the trust of a business partner and eventually a friend!

L is for Listen

Ask for feedback, and listen for both positive and negative criticisms. Follow up with a call after each project, listen to the feedback and corrections. Take notes so that you can improve on your products and services in the future; strengthen yourself and allow yourself to learn, unlearn, and relearn.

L is for Learn & Return

Every quarter, make it a habit to learn something new from all the information available in the feedback, note the faults, activate the correcting mechanisms, and return even more robust!

As you likely know, this HBR article demonstrates that studies have shown that retaining customers can be far more lucrative than finding new ones. Do you use any specific initiatives to limit customer attrition or customer churn? Can you share some of your advice from your experience about how to limit customer churn?

It costs nothing to do the right thing. It is vital to have the humility to know that without your customers, you don’t exist. Everything matters, understanding the intricate details about your clients will allow you to serve your community better. It’s all about being better than the day before, and if there is churn, you’re responsible for addressing the problem. For example, we have weekly user story sessions where we walk through various scenarios to build everything with the user in mind. In general, we frequently talk to customers so we can best serve them. Business is all about service; treat your customer with respect and care. They will reward you will promotion and loyalty. Also, the churn can be monitored with various data solutions, so your feedback loop can locate any problem so that it can quickly be resolved.

Here is the main question of our discussion. Based on your experience and success, what are the five most important things one should know in order to create a very successful tech company? Please share a story or an example for each.

1. Have a WOW mentality! I call it the WOW mentality because it means “with or without” you have to have the discernment to keep going and keep creating. This is critical because, at the beginning of your journey, no one will care about what your building as much as you. There will be a lot of negative people that will project their failures and insecurities on to you. People will tell you what you can and can’t do. Having a WOW mentality will prevent the negativity from corrupting your vision and allow those who truly align with your mission to join you.
2. Build value-based teams. I love my team, emphatically. I value each and every one of their opinions and work. We are a close-knit tribe who all share the same values. I consistently audit teams and partners and look for integrity deficits. I am incredibly cautious; if I spot an integrity deficit, I won’t move forward. It’s not worth it in the long term. I used to get excited by resumes and titles while overlooking the importance of character. When in reality, character is the most important thing. That is probably one of the most expensive lessons I had to learn.
3. Recognize that purpose is a fundamental pillar of a successful company. It is slightly insane to wake up one day and decide to launch a tech 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. Having your purpose helps ground you in your “why” and define your mission.
4. 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. A wise man once said, “every day can’t be Christmas.”
5. Endurance is key, so plan on pacing yourself. Remember, it’s a marathon, not a sprint. It will always take way longer than you think it will. You may even struggle with imposter syndrome along the way. As entrepreneurs, we’re always launching, always building, always growing, and always learning. It is such an iterative process; thus, it requires excessive endurance to have the fortitude to keep going. Rationalizing the reality that creating something novel isn’t easy, understanding that will increase your mental stamina and prepare you for the rollercoaster.

Wonderful. We are nearly done. Here are the final “meaty” questions of our discussion. 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.

We are very blessed that very prominent leaders read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this 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.

Thank you so much for this. This was very inspirational, and we wish you only continued success!