I have nothing but respect for anyone who decides to leave a full-time job to start a business; it’s a bold move that comes with significant risks. According to a study by the Small Enterprise Development Agency, 60% of new businesses in South Africa fail within their first three years. A sobering statistic. Being self-employed is often more stressful than working for someone else, and it’s widely recognised as one of the most demanding careers. If you’ve been running your own business for five years, you deserve a pat on the back.
In this week’s entrepreneur stories, we’ve invited business owners from various walks of life to share their journeys and insights.
Lebohang Hadiyo Mokolokolo
A self-taught and passionate florist, Lebohang founded Blooms at Trails, which grew out of the successful events company, Trails Events and Projects, based in Katlehong. The brand has since expanded to include beautiful florist kiosks at Rosebank Mall and The Glen Shopping Centre, bringing a touch of elegance and joy to customers in these bustling hubs. With a keen eye for detail and a love for nature’s beauty, Lebohang creates stunning arrangements that captivate and inspire.
Masixole David Magqabi

A seasoned professional and Director with over 15 years of experience in the entertainment industry. As the founder and Creative Director of Timeline Entertainment, Masixole has spearheaded numerous successful projects across both corporate and television sectors. His expertise extends beyond creativity, encompassing technical skills that ensure the highest quality productions.
Diana Victor

Diana is the owner of Bold Events (Pty) Ltd. Her goal was to build strategies that make her a dedicated partner to agencies and brands alike, tackling daily challenges in planning, executing, and driving marketing campaigns and events nationwide. Diana is a strong leader, adept at training and mentoring team members for success. Honest business ethics, integrity, and dedicated work principles are core to her values.
Seipati Malinga

The founder of Tshemaseka Clothing, a primary cooperative clothing brand that started in 2014 and was officially registered in 2022 with five members. Tshemaseka aims to design clothes for all types of people.
Host:
Lebohang, welcome. Please tell us a bit about your business and how it all started.
Lebohang:
I am a self-taught florist. This business actually grew out of a company called Trails Events and Projects. It all started as an events business. While working in events, I noticed that I was spending a lot of money hiring florists to help with the flowers. So, since 2015, Trails has been in existence, but the florist side only began in 2019. I’ve been working with flowers since then, mostly from home. Ironically, I never really liked flowers because I have a slight allergy to them. Every time I have pollen on my hands, I tend to sneeze.
Host:
I see that Diana is here. How are you? Let’s move over to you.
Diana:
Thank you very much for the opportunity and for inviting me to your show. I want to start by saying that I am the owner of Bold Events. Events are very specific, but we’ve been doing all kinds of below-the-line marketing since our inception. However, our major contributor has been corporate events and brand activations. We work with a lot of big brands, setting up events and building assets, which is something we’ve been particularly proud of over the last two years.
Host:
I see that we also have Seipati. Can you please introduce yourself?
Seipati:
I am a designer based in Qwaqwa in the Free State. The name of my business is Tshemaseka, and we primarily design clothes based on the customer’s needs and preferences.
Host:
Masixole, let’s move over to you. Can you introduce yourself and your business?
Masixole:
Thank you so much for the invite; I really appreciate spaces like this. I am the founder and director of a company called Timeline Entertainment. We are a TV and film production company, and we also operate in the corporate space. Whether it’s corporate visual content or television, we’re there. We do a lot of corporate work, but TV is where we excel the most. I started the business full-time around 2013, transitioning from a 9-to-5 job, where it had initially been a side hustle. By 2014 or 2015, the company was fully operational and has grown into what it is today.
Host:
Lebohang, I’m curious to know more about your business. Can you give us a clear picture of its size? How many people are involved, and how many branches do you have?
Lebohang:
We have a kiosk in Rosebank, which was the first one we opened in April. I have three ladies working for me there. We also have a kiosk at The Glen Shopping Centre, which opened last month, at the end of July, where three more young ladies work.
Host: I’m curious about your upbringing. Can you take us through your childhood? Were there certain people who inspired you to become the entrepreneur you are today?
Lebogang: I’m not entirely sure if there were specific people, but what I’ve always known about myself is that I’m a very creative person. When I started Trails, it was something I had been doing for quite some time—whenever someone had an event, I would show up and put things together. Growing up, I was always the colourful one, the friendly one, and definitely the loudest.
Host: What was the tipping point, that moment when you decided, “I’m starting today”?
Lebogang: I was going through some mental health challenges. I wasn’t coping at work; waking up every day felt like a chore. I knew I had to let go of my job. But when I sat down to reflect, I wanted to do something that didn’t feel like a chore—something that truly resonated with me.
Host: What does it take for someone to have a kiosk at a mall? Did you have to negotiate with the mall management?
Lebogang: It’s not an easy journey, let me tell you. When I started at Rosebank, I met this young gentleman who was very willing to assist. His support made a big difference in getting things off the ground. I had to put together a proposal and a rendition. Then, they review and approve your proposal before you can move forward.
Host: Masixole, you are involved in creative spaces, and I know that can be a challenging industry.
Masixole: It certainly is a challenge. As fun and exciting as it is, there are definitely obstacles. What drew me to it was a deep passion—my love for storytelling and creativity, and the joy of seeing people enjoy what you’ve created. The driving factor behind everything has been that passion. In the filming industry, funding can be a major hurdle. To navigate this, we take on corporate work, using those funds to support the storytelling side of the business.
Host: Could you paint a picture of your business? Tell us about the size and type of projects you have been involved in.
Masixole: At the moment, we primarily focus on reality shows. One of our notable projects for SABC 1 is called IkasLam. This show follows prominent business people and sports figures, taking them back to the townships where they grew up. In a nutshell, that’s the essence of what we do!
Host: Diana, you’ve been involved in the events space for years. At what age did you decide to become an entrepreneur?
Diana: I wasn’t quite sure what I wanted to do with my life after high school. I began studying law, but quickly realised it wasn’t for me. After spending some time abroad, I returned to Johannesburg and started working in various jobs. I found myself in corporate gifting and the clothing sector, and from there, my career took off in many different directions. Although I made money, I was never truly satisfied. I always felt there was more I could achieve, and the truth is, if you don’t own a company, your ideas can remain just that—ideas.
Host: Seipati, let’s turn to you. Could you describe your cooperative business and tell us how many people are involved?
Seipati: I’m someone with a pear-shaped figure, so I often find that clothes fit well around the waist but are too small around the hips. That’s what inspired me to design my own clothes. I attended design school with the intention of creating pieces just for myself, but soon, others were drawn to what I was making and started asking for their own designs. As a teacher by profession, I usually work on my designs after school. Realising that my workload was growing, I reached out to some ladies, and together, we formed the cooperative Tshamaseka. We take orders from anyone looking for custom clothing, with a focus on traditional wear. We’ve noticed a resurgence in celebrating tradition, which is reflected in our designs.
Final Thoughts:
The stories shared by these remarkable entrepreneurs reveal the bold steps, personal sacrifices, and passionate pursuits that define their journeys. From overcoming personal challenges to seizing opportunities, each of them has demonstrated the resilience and creativity required to transform ideas into thriving businesses. Their experiences underscore the reality that while entrepreneurship is fraught with risks and demands, it also offers profound rewards and personal fulfillment. As we celebrate their achievements, we are reminded that with determination and vision, turning dreams into reality is indeed possible.