Tiwa Ogunlesi is a confidence coach and the Founder of Confident and Killing It. In her own words, the company is a purpose-driven media organization that is all about waking people up to their worth, helping them master their minds, believe in themselves, and show up in the world. In this interview for Follow the Founder, Tiwa talks about her journey into entrepreneurship, with all the benefits, hurdles, and surprises it has presented her over the past four years.
Uncovering The Roots of Her Mission
The biggest factors in shaping our values and beliefs are your family, peer group, and environment. So to fully understand Tiwa’s journey, we start with her upbringing.
“I was born and raised in Nigeria. I come from a family of very strong women: my mother and both of my grandmothers were trailblazing women. I was surrounded by women doing incredible things. Growing up, there were no limits in my mind to what I thought women could do. I think that truly shaped how I showed up in the world, who I thought I could be, and what I thought I was capable of doing.”
Despite being surrounded by such strong female models, Tiwa struggled with low self-esteem as a child, in her teens, and even into her young adult life much like the rest of us. Working through this challenge was the first spark to kindle the fire that later fueled the inception of Confident and Killing It.
“There’s a statistic that says 61% of teenage girls feel insecure about themselves based on the media they consume. That was me exactly. I would compare myself often to people around me. I didn’t think I was smart enough, I didn’t think I was pretty enough. I didn’t look like any of the models I saw on TV. It was the full narrative of not being good enough. And even though I had a lot of love around me, mentally, my mind was just high on self-sabotage. It wasn’t until I started my confidence journey that I realized I learned how to master my mind, believe in myself, and take action on my dreams and my goals. That completely changed my life and gave birth to Confident and Killing It.”
Despite this journey of confidence and self-love, it wasn’t until years later that Tiwa truly started thinking about entrepreneurship. The first push was the support she received when sharing some of her experiences online.
“When I started to talk about confidence on social media back in 2016, I got a huge response from women and girls, thanking me for what I was saying. This deeply inspired me. I needed to hear it. So I asked myself, ‘How can we change the media landscape where messages of love, positivity, and power are the norm rather than the exception?’”
Jumping into Entrepreneurship
Sometimes, even if we’re ready to go on a new journey, our subconscious fear and self-doubt may cloud our judgment and hold us back. In those situations, what helps the most is someone we trust or someone who has done it before to give us that initial push. Reassuring us that the path we’re on and dreaming of taking is the right one.
“I always referenced the time Annalee and I had lunch in Soho, London as one of those pivotal moments for me to start the business. I was contemplating quitting my job, but I didn’t have any clients lined up. I had started Confident and Killing It as a side hustle. I had proof of concept, people wanted to hear from me. I had been going around speaking at different universities, but they weren’t paying me. But Annalee said to me when I was hesitating that once you took the leap of faith and gave your passion project your full attention, plenty of opportunities would begin to open up for you.
“So I quit my job without any paid gigs lined up and just three months’ worth of savings. I didn’t have a business plan either.”
It is rare that the person you are now will understand when it is the right time to take a leap. We can spend our whole lives waiting for the “right” moment. Sometimes we need an extra push. No matter how self-aware we are, we don’t always recognize our potential, our readiness to jump out of our comfort zone.
“When I gave the business my full attention and capacity, the universe opened an abundance of opportunities. When you don’t have the capacity for something, there are only so many blessings that can flow into your life.
“So, my brain completely rewired after I quit. I wrote the business plan in a day! When I was 100% focused on what truly gave me life and on what my purpose was, I also got into a state of flow. And the flow state is when you enter genius mode. Is when you lose track of time, and you’re just creating at a speed that is so profound, no distractions, optimum flow of creativity.
“When I became a full-time entrepreneur, I unlocked this power inside me that made me ready. I wasn’t ready before I quit. I wasn’t ready before I had the capacity to focus on this one thing that brought me purpose.”
Creativity, Self-Belief, and Resilience in Overcoming Hurdles
When a mission is deeply personal to us, we have a crazy drive to push and to build. We enter that beautiful flow state and things align. But sometimes even when we work for ourselves and fulfill our mission, it’s not all rainbows and flowers, we have tough days, we have days when we want to give up, and when we are over it. In those times, it’s important to have an anchor to go back to, to remember WHY we started and WHY it matters. This will give us the energy, strength, and resilience to keep going. And even then, sometimes the universe will serve up a challenge we didn’t expect that makes us recalibrate.
“As I said, I quit with only three months’ worth of savings. In March 2020, they were running low. The pandemic hit, and all my potential leads went out the window. The whole business plan I had created was about in-person events and meetings. Everything was canceled. I was getting rejections from everywhere. Some people even ghosted me. I had only £100 left in my account. So I was in this difficult dark place. Luckily, I had family to support me. I was living at home, so it wasn’t like I didn’t have a roof over my head or anything like that. Nevertheless, I felt like a complete failure.
“I asked myself: ‘Is this the story you want for yourself?’ Clearly, the answer was ‘No’. A lot of the time, we know what we don’t want to happen. But we never stop to reflect on what we do want for ourselves. I wrote down that I wanted my story to be that I was building a household brand that reaches people all over the world. I wanted to work with some of the biggest organizations in the world.
“And then I said, ‘Whatever goes down must come back up because I am unstoppable’. And so every day in the pandemic, when my inbox was dry as hell and no one was checking for me, I read that out every single time. Whatever goes down must come back up. I am unstoppable.”
When we know what we want for ourselves and are willing to go to all lengths to get it, we get creative with the resources we are given, no matter how limited. Tiwa started an online webinar series called “Killing it As An Entrepreneur” where she invited women to talk about their experiences. Even though she was not even in the same space as them. Ultimately, being surrounded by people she admired gave her the inspiration to turn her situation around.
“Suddenly, I had around 500 women joining “Killing It As An Entrepreneur” every single time. I was learning from them, and I was also positioning myself in the same realm of entrepreneurship. Before I knew it, I was getting opportunities to work with Google, Meta, Deloitte, Morgan Stanley… All these women who were joining my sessions had started recommending me across their networks.
“If people didn’t want to book me for talks, I booked myself, I put on my own talks, and that led to so many incredible opportunities. I would say that was definitely a pivotal moment in my entrepreneurship journey, realizing that at the end of the day, you have to use what you have in your hands and create your own opportunities. Don’t wait for people to bet on you or to give you a chance, you have to give yourself a chance.”
Tiwa’s journey from struggling with self-esteem to becoming a global advocate for self-confidence is not just inspiring—it’s a testament to the transformative power of self-belief.
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