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The journey to becoming an entrepreneur and overcoming its challenges along the way

by wrich

By Kola Tytler, CEO, dropout and HypeAnalyzer

Growing up

Kola Tytler, CEO, dropout and HypeAnalyzer

The second child of four siblings, I was born in London to Nigerian parents in1994. We moved to Italy (where my parents and older sister were previously living), in the same year, and I grew up in fascist-built Latina, a young town near Rome where immigrants were few and far apart. I was the only foreigner in the school I attended, and my fellow pupils were very aware of this fact, never failing to ensure I realised that I “stood out”.

My childhood was characterized by a curiosity and passion for learning. Since a young age, I consistently held anearly flawless academic record along with a strong interest in football, basketball, and sports videogames.

In 2010, I had a very bad accident where I passed out in a swimming pool. I drowned and suffered from ARDS, requiring non-invasive ventilation (CPAP) and a long hospital admission. My very-near-death experience somehow strengthened my drive to be successful. I just never looked back. Between the ages of 16 and 19, due to a lack of paid employment, I began volunteering on a weekly basis, to help to build my CV. The experience I gained in these years, working in foodbank and charity shops, proved invaluable into shaping the person that I am today.

Moving to the United Kingdom and those all-important first connections

After graduating from High School with top grades, in 2013 I moved to London to attend university with just two suitcases and a few hundred pounds to my name. I worked in jobs throughout my entire time at university to help fund my studies, while I was training to become a doctor. This led to a significant burnout, and I was forced to resit several exams throughout medical school. Never the less, I believe the time-management, resilience, and emotional strength I developed because of failing for the first time in my life, has continued to fuel my drive to succeed.

I always had a huge passion for sneakers and after fulfilling my dream of buying a pair of Nike Jordan’s, I became aware and fascinated with the underground sneaker resale market. I knew I had to be a part of it, so I taught myself how to code and wrote a sneaker bot (2015). Shortly after this, I met Yiannis, who had launched YEEZY Mafia, an online platform where users would exchange information and the latest news pertaining to Kanye West’s sneaker line. At the time the site had a mere 20 members, but together, Yiannis and I expanded Yeezy Mafia into a reliable news outlet, and today it remains the worldwide unofficial source for information relating to Kanye’s sneakers. Kanye has knowledge of the site and is a follower, which is a true testament to its credibility. My involvement in Yeezy Mafia has gradually reduced since 2018, as I started to focus on different projects. 

A few months after meeting Yiannis, I met Stefano who became my right-hand man, before going on to launch ‘Outpump’, an Italian streetwear magazine, which is now the highest ranked magazine in the country, due to the sheer volume of monthly visitors.

My key to success: failing again and again 

After yet another failed university exam, in 2018 I was diagnosed with dyslexia and dyspraxia. However, rather than allowing this information to deter me, it inspired me to work even harder. I later took two monitored IQ testsscoring in the top 1% of the population in both the Cattell II and the Culture fair tests, indicating an IQ of >155 and >132, (depending on the scale used). I remain a Mensa member, to this date (membership number 962112, UK Mensa), although I am yet to find a useful purpose to this.

Between 2016 and 2018, Stefano and I decided to implement our coding competencies (both being self-taught) to create something new. Together, we wrote a software programme, which would track available sales and price data for several limited-edition sneakers. We observed a few recurring trends and structured a system where we would determine the likelihood of an item increasing in price over the following months. The idea was based on automation allowing us to transform a physical commodity, sneaker, into a solid appreciating asset. Thus, HypeAnalyzer was born, and we used this software to make investments in sneakers. Within months we realised the software was surprisingly efficient and this provided us with a reference to follow in the vastly unregulated industry, which the secondary streetwear market represents.

Combining different passions

In 2018, I decided it was the right time to take a further leap of faith and open my very own sneakers store, focusing on limited edition pieces and making use of the data we had acquired from HypeAnalyzer. Within 6 months, after creating a strong team consisting of my closest friends, and with no external funding, under my strategic guidance, the venture was ready to go. The plan – a first retail location in the centre of Milan, an online website to launch later, and utilising online communities and social platforms, to help build up momentum. 

My contemporaneous frustration with university led to the business name “dropout”, which is also a shoutout to Kanye West’s “College Dropout”, the album I was listening to at the time.

With a highly trafficked flagship store located in the centre of Milan, dropout proved a huge success right from the very start: more than 1000 people attended the opening weekend and to this date, its doors have opened to more than 50000 visitors from all over the world. 

Despite the name of the flag ship store, I did continue with my studies at university and am now qualified as a medical doctor. I am running a 7 figure multi-million-pound business, while working on the NHS front line during a pandemic and juggling clinical commitments. There is also the continued desire to keep the business afloat despite its main retail location being based in Milan, right by the European epicentre of the pandemic’s first wave.

In October 2021, three years after its inception, dropout launched its first funding round, raising €750k via equity crowdfunding in a lightning time of 6 days. This was following the board approval of an extension of the initial €500k goal (which was reached in just 4 days of the original 62-day campaign). The move will see dropout open a new retail location, as well the opening of several temporary locations throughout Italy; improve its e-commerce site and the further development of HypeAnalyzer.

Moving on: the future of sneakers resale

As part of dropout’s expansion: we are currently studying the creation of a portal for investment in sneakers as alternative assets. We believe the secondary sneaker market is firmly here to stay (and get bigger and bigger, in fact), and stores such as dropout are already becoming more and more common across Europe. We aim to make dropout one of the most trusted names in the wider fashion-sphere while shining lights into the interesting world of investments in alternative assets.

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