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Exclusive Interview with Serial Entrepreneur Tiwalola Olanubi Jnr

Today we’d like to introduce you to Tiwalola Olanubi Jnr.

It’s an honor to speak with you today. Why don’t you give us some details about you and your story. How did you get to where you are today?

Firstly, I am proudly Nigerian and then a serial entrepreneur creating employment in the media, food, tech and real estate industries. I have an honorary doctorate degree in Arts, for my contributions to digital marketing and entrepreneurship in Africa.

I have the privilege of leading teams at DottsMediaHouse, where we co-create media magic with global brands and TrendUpp Africa, a startup that leverages technology to connect and support content creators across Africa. At Trendupp, We organise the nationally recognised annual TrendUpp Awards that honors the work of content creators on the continent. In the last decade, My work has been recognised by a number of prominent organisations including the Guardian, the World Alliance Group, European American University, the London Business Academy, Microsoft, The Future Awards Africa to name a few.

My entrepreneurship journey spans over 15 years and has been defined by four principles; finding my purpose early, mentorship, consistency and God’s grace. As an undergraduate in the University of Lagos, I realised that my true passion was media and communications, not Quantity surveying which I was admitted to study. With this realisation, I began to pursue opportunities in media and in 2010 eventually became the first Blackberry ambassador in Nigeria, chosen from 3,000+ shortlisted candidates. That relationship lasted four years and helped me establish the network that could become my lifeline when I eventually launched my media company – DottsMediaHouse in my final year of university, pivoting away from my course of study into my true purpose.

I’m sure your success has not come easily. What challenges have you had to overcome along the way?

Success in entrepreneurship requires a balance of hard work, grit, innovation and consistency. Being Nigerian and running a business out of Africa raises the stakes for any entrepreneur and that is why my personal and professional life are even more remarkable.

I am very proud to be Nigerian and across the world Nigerians are renowned for our tenacity and our exemplary business acumen, but it is important to discuss the many uniquely Nigerian challenges I have had to overcome in my ten years in business.

Nigeria as a nation lacks the adequate corporate structures and legal frameworks, our physical infrastructure is archaic, majority of the workforce are undereducated and tech-illiterate, year-on-year inflation that affects the prices of goods and services, the effect of which is worsened by epileptic power and persistent fuel scarcity. These factors compound to make it almost impossible for most businesses to thrive in Nigeria.

A peculiar challenge I had early in the business was convincing international clients to take a chance and trust us with their campaigns. These campaigns require an extensive advertising and media budgets to execute and international practice often expect the bidding company to execute first and receive payment later. As a startup, we didn’t have the luxury of collateral for loans or liquid capital to direct towards execution, so we had to starve our needs, divert profits from other projects as capital for these executions. The solutions we devised are the reason why we are thriving today.

Let’s talk about the work you do. What do you specialize in and why should someone work with you over the competition?

I am a serial entrepreneur who works across diverse industries. While my primary industry is media and communications, I am actively pursuing my interests in the real estate, tech and food industries. Media & Comms remain my most passionate, profitable and impactful business venture.

DottsMediaHouse is the flagship company in our media group – Dotts Group and Africa’s foremost media and communication firms. Our three pillars; content, consulting and strategy, defines how we create campaigns that tell stories and inspire movements across Africa for corporate, tech and institutional clients. We are collaborative and always excited to invite our partner brands to be a part of creating the ROI-driven campaigns that help them reach and exceed their marketing goals.

Our workforce is composed almost exclusively of young African professionals and we are very discerning about the brands we take on for DottsMedia. We want brands who share our vision for storytelling and are flexible about how those stories need to be adapted to resonate with African audiences and we have been opportune to work with global brands like Pepsi, HP, Intel, ChipperCash, Pizza Hut, the Dutch Embassy among others. We specialise in media buying, content production, social media management, influencer marketing, digital advisory and activations.

One of the advantages we offer clients over competitors is our workforce which is youthful and innovative. We also have the advantage of industry specific data, from which we draw insights that help us streamline our campaigns and maximise results fo

What’s your best piece of advice for readers who desire to find success in their life?

I would advise anyone desiring success to do just one thing – start. Start building around that idea you have as early as possible, even before you have a complete or comprehensive plan or the resources or manpower to execute it at scale. Use the resources you presently have to commit to the idea, even if it is something as small as reserving a domain name or marketing your idea to a potential customer/client/partner.

In my experience, corroborated by many of the successful entrepreneurs I’ve studied and respect, procrastination and self doubt cause people to delay for fear of public humiliation or personal failure. Failure is inevitable if we never begin. The earlier we test out an idea, the sooner we know if it is worth our time and attention. So again, I’d advise anyone who has a lofty startup idea or a fancy dream for a business to pick up their tools and just start.

Speaking of success, what does the word mean to you?

Success is a subjective idea, and the metrics can only truly be defined by each person for themselves, so I can only speak for myself as informed by my personal experience when I talk about success, hoping that it will provide a relatable perspective for your readers.

Over the last 15 years, I have started and grown 4 businesses across different sectors, all successful in different levels, some growing into million dollar businesses (without any debt, loans or investment received). I have been recognised nationally and internationally with awards for my work, and been honoured with a doctorate in the Arts. Experiencing this much success in an environment that seems so antithetical to growth has allowed me to come to a more holistic understanding of what success means to me – which is being able to integrate personal ambition with one’s sense of self or identity. I have come to this place of personal fulfilment and as such, my self worth is no longer tied to my successes. I protect my peace of mind by ensuring there is a clear separation between ambition and purpose and honouring both equally.

What’s next for you?

I have been very privileged to have built a successful Pan-African media business, an innovative tech company, a relatively new but growing real estate business, all these granting me a mature set of perspectives. But now I am prepared to take on bigger challenges personally and professionally.

My immediate goal is to make my impact felt outside of Africa across several sectors, through personal exploits and my businesses. Philanthropy and social engagement are avenues I wish to explore on the personal front and expansion is the focus for our many businesses.

Dotts, our media business is the main vehicle through which this expansion will happen, and my team and I are working diligently to expand into new markets and open physical offices in Europe and the Middle East.

Finally, how can people connect with you if they want to learn more?

Social media has really transformed how we all do business so despite my busy schedule, I make time to maintain an active presence on select social media platforms. LinkedIn is my primary social media platform for all professional interactions, inquiries or collaboration requests. Connect using my name – Tiwalola Olanubi Jnr.

I am also active and verified on Instagram, on there I am more flexible with the kind of content I share, and the way I interact. So if you want to get a sense of my family and everyday life, see the places I travel for work and the projects I am currently involved in, or you just want to connect with me on a creative social platform, Instagram is the place. My handle there is @TjDotts.

As a millennial, I’m still very much attached to email, and I refresh my inbox religiously, so the quickest way to reach me for urgent matters is via email at

Social mentioned is
@tjdotts IG / Tiwalola Olanubi Jnr – LinkedIn

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