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Bankrupt And Dreams In Tatters: How Sheree O’ Brien’s Self-Belief Drove Her To Success

In her teens, Sheree o’Brien worked two jobs to fund her start-up dreams. But then one bad decision left her in massive debt and her dreams in tatters.

Nadine Todd




Vital Stats

  • Player: Sheree O’Brien
  • Company: Splakavellis Management
  • What she does: Music management
  • Launched: 2000
  • Visit:

When Sheree O’Brien launched Splakavellis Management at the age of 19, she couldn’t find anyone willing to give her start-up capital. Instead, she used the money she was earning as an events manager at clubs by night, and from her ‘real’ job by day, to bankroll her dream. It was a time of little to no sleep; of cashing up at the club at 5am before going home for a shower and heading off to her day job.

The hard work and dedication was paying off though, and soon O’Brien was the only artist management and booking agency based in East London. In a scene dominated by ‘big Jozi cats’, she was managing a handful of legendary artists like DJ Mbuso, Soul Candi and Phezulu Records’ stable of DJs.

Related: Naadiya Moosajee’s Overriding Purpose Is Driven By Her Passion

Once she was reasonably established, O’Brien made the first big mistake of her career. One that would almost cost her everything.

Hard lessons

“I invested in a national tour for a then-popular girl group, with two other partners,” she recalls. The tour did not go well. Because all of the venue deals and the contract with the artists’ management company were in O’Brien’s name alone, she knew that pulling out halfway through the tour would just lead to legal action.

“To avoid being sued and possibly ruining my company’s reputation, I decided to go broke instead. I made sure the artists, security providers, drivers, accommodation and meals were settled from the income of the events, but sacrificed my needs to make ends meet. I was sleeping in our combi and not eating. By the time we reached the final city in the tour, I didn’t have R1 to my name. I couldn’t even get home. My friend Lira (who was also still a struggling artist back then) bought me a train ticket back to East London. It was an 18-hour journey, and I couldn’t afford anything to eat. I would smell the food wafting up from the food car and try to sleep to ignore my hunger — but sleep also doesn’t come easily when you’ve just bankrupted yourself.”

Her partners had cut and run, leaving O’Brien to carry the debt alone, but instead of throwing in the towel, she redoubled her entrepreneurial efforts, this time armed with some valuable business lessons and insights under her belt.

“I learnt how fickle our industry is and that I will never know everything. On a practical level, I learnt how important it is to always put a Memorandum of Understanding (MOU) in place when embarking on a joint venture. Your MOU should outline who is contributing, how much, and what the return expectancy is. It can also highlight potential scenarios of loss. If I’d had an MOU in place, I wouldn’t have borne the losses of the tour alone.

“From then on, I stopped investing my own finances into events, at first out of necessity, but later as a general rule. I also started working more closely with my accountant. Today I won’t even buy a new laptop without asking her permission. She helps me to keep things lean. When my six-year-old laptop died on me and I asked her if I could invest in a MacBook, her reply was that I should get some ‘MacCommonSense’ instead.

Related: What The Concept Phase Really Means To Alex Van Tonder

Picking up and carrying on

Taking such a hard knock shook O’Brien’s confidence. Almost everyone she knew was telling her to declare bankruptcy and move on. She refused.

“I’d been working on this dream since I was 14 years old. I’d had a major setback, but that just made me even more determined to succeed. I had to move back in with my parents and start all over again, getting a day job and freelancing after hours, but slowly I paid off my debt and got back on my feet. All it took was patience and determination.”

O’Brien’s decision to bite the bullet and save her reputation paid off. “My brand name stayed strong, and so I didn’t actually lose any clients during that time. If anything I was even more in demand than before. For seven years I sacrificed buying new clothes, eating take-aways, sleep, family time and my sanity in order to pay off all of my debt and start on a clean slate.”

Once again, it was seven years of hard-won lessons though, particularly because O’Brien refused to cut corners or compromise on her morals.

“I learnt three big lessons while I was rebuilding my business from the ground up,” she says.

“First, the only way to learn about risks is to take them. As an entrepreneur, safety should not be your go-to place. You have to be all-in, regardless of how many times you fall.

“Second, there will always be people who want to make a quick buck off you. I can’t tell you how many offers I received from friends of friends of government officials to enter into tender partnerships with them in return for kickbacks. They thought I was absolutely mad to turn away ‘big money’, particularly because I was in debt, but that wasn’t how I wanted to build my business. I’m a firm believer that the best tool in your marketing arsenal is your reputation, so I made sure that throughout my journey, mine stayed intact. Whenever I was offered a deal that I was uncertain about, I asked myself if my parents would be proud of this decision. If the answer was no, I walked away.

“Finally, if you’re passionate about something, and you know you’re making a difference in your industry and impacting the world positively, then it’s okay to take your time to build something great. Not everything has to be a rush. Rather build something well that will last than something quick that has no staying power.”


Finding a balance

Alongside her business hardships were personal ones, and O’Brien has worked as hard on finding a balance between her personal and professional life as she has on building a sustainable foundation for Splakavellis Management.

“Business isn’t only about planning and strategising,” she says. “As an entrepreneur you need to understand that success doesn’t only come from managing your business well, but from managing yourself well too.”

O’Brien knows what she’s talking about. While she was struggling to pay off her business debts and emerge from bankruptcy, she was also trying to put an abusive relationship behind her, leaving East London for Joburg, only to be stalked by her ex-boyfriend in her new city. Family deaths as well as the passing of one of her artists also took their emotional toll.

Related: 27four Investment Managers Aren’t Afraid Of The Big Boys

“In between all of this, I also became a parent. Being a single mother and a business owner really makes you understand how important it is to have a support base, but also that your business and personal lives can’t exist in isolation. They impact and influence each other.

“I’m incredibly blessed to have an amazing family. My business requires me to travel every other weekend, and sometimes for weeks at a time. Without their help this wouldn’t be possible.”

O’Brien is proof that you can have it all, as long as you understand that there are no clear lines between personal and business for an entrepreneur.

“My professionalism has been incredibly important in this regard. I’ve always been known as the hardest working woman in this industry. In 16 years I’ve never missed a deadline because I don’t take anything for granted. I always do more than what I’m hired and paid to do.

“This focus and dedication on going above and beyond has meant that when I’m facing challenges in my personal life, I need to accept them and move on, without wallowing in my own misery. It’s easy to get side-tracked by the personal, but then I would lose my competitive edge professionally. Instead, I’ve found that personal challenges can actually be a strength, because I throw myself into my work.

“There are so many reasons not to be successful if you look for them, but I’ve found that there are just as many reasons to fight for your dreams. It’s all about how you look at a situation, and your attitude. If you want something badly enough, you can always make it happen.”

Remember this

The only way to learn about risks is to take them. As an entrepreneur, safety should not be your go-to place. You have to be all-in, regardless of how many times you fall.

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Lessons Learnt

#Wealthiest List: 8 Self-Made Millionaires On How They Built Their Wealth

These inspirational self-made millionaires built businesses with nothing less than hard work and sheer determination.

Catherine Bristow



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1. Nick D’Aloisio Wrote a Million Dollar App At Age 15


At the age of 15, Nick D’Aloisio wrote an app while sitting in his parent’s bedroom in the UK. At the age of 17, D’Aloisio sold his app Summly – a mobile news summarisation app to Yahoo for a staggering USD 30 million.

As one of the youngest millionaires, D’Aloisio is also the world’s youngest entrepreneur to be backed by venture capitalists – having secured seed funding from Sir Li Ka-Shing, Hong Kong’s billionaire, as well as raising USD 1.23 million from celebrity investors, including Yoko Ono and Ashton Kutcher.

“The number one thing I did that I think was wise was to get, through some of my advisers, was a Chairman; basically someone who was a very experienced business person, an industry veteran — Bart Swanson, who had been at Amazon and then Badoo. Then, myself and Bart really started finding people and growing the team.”

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Lessons Learnt

7 Cannabis Industry Millionaires Making It Big In The Marijuana Business

These entrepreneurs have capitalised on a new market set to continue to grow rapidly as more countries legalise marijuana across the world.

Catherine Bristow



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1. Brendan Kennedy


Brendan Kennedy worked on job sites as a carpenter to pay his way through university, with his eyes set firmly on becoming an architect, until the allure of Silicon Valley changed the course of his direction. While working at technology start-ups Kennedy began thinking about the possibilities that medical marijuana provided.

“I was really sceptical of medical cannabis,” he says. “It took a year of having conversations with patients and physicians and hearing the same story, repackaged but essentially the same, over and over and over again, where my scepticism eroded and I became a believer.”

In 2013, Kennedy and his partners applied for a licence from Health Canada and launched Lafitte Ventures, which was later renamed Tilray. Today, the company is a global leader in medical cannabis research, cultivation, processing and distribution.

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Lessons Learnt

Scaleup Learnings From Our Top Clients – What The Most Successful Entrepreneurs Do Right

So, how do our successful clients move through these constraints to scaling up? We see four key drivers of success, and they are: people, strategy, flawless execution and finance.

Louw Barnardt




You’re out of your start-up boots, staff is increasing, your client base is growing, revenue is up and you’ve proven your case to the market. Now it’s time to scale up. The challenges of this vital growth phase are different and it’s a time that demands different mindsets and different actions. In a world littered with small business failures, it helps to be well-prepared for scaling up using a proven methodology. At Outsourced CFO, we get an inside look at the success factors of our clients who are mastering the transition.

On the one hand, scaling up is a really exciting phase; this is what moves you into real job creation and making an impactful contribution to economic growth. On the other hand, it is really hard to scale up successfully. We see three major constraints that limit companies’ transition from start-up to scale-up:


The business has to have the leadership that can take it to the next level. When you start scaling up, especially rapidly, the founders can no longer do everything themselves. The team must grow and include new leadership talent that can take charge and execute so that the founders are working on the business instead of in the business.


The processes, procedures, networks, systems and workflows of the business all need to be scalable. This is imperative when it comes to your infrastructure for the financial management of your business. You’re only ready for growth when your infrastructure can seamlessly keep pace.

Market access

Scaling up demands more innovative marketing and storytelling so that you can more easily connect and engage with the new employees, clients, network partners, investors and mentors that need to come along with you on your scale-up journey.

Businesses that build a market conversation and a compelling brand narrative during their start-up phase are better positioned to have this kind of market access when they need to scale up.


It is critical to have the right people on your team. Our successful entrepreneurs have what it takes to attract, inspire and retain top talent. A strong team of smart, ambitious and purpose-driven people who love the company and want to see it succeed contribute greatly to a world class company culture. They are adept at communicating a compelling vision and establishing core values that people can take on. These entrepreneurs are tuned into the aspirations of their people and focus on developing leaders in their teams who can in turn develop more leaders.


It is planning that ensures that the right things are happening at the right times. At successful scale-ups strategies and action plans are devised to ensure that the most important thing always remains the most important thing.

Strategy includes input from all team members and setting of good priorities for the short, medium and long term. Goals are clear and everyone always knows what they are working towards. The needle is continuously moved because 90-day action plans are implemented each quarter to achieve targets and goals that are over and above people doing their daily jobs.

Flawless execution

Top entrepreneurs are not just focused on what operations need to achieve, but how the business operates. They have the right procedures, processes and tools in place so that everyone can deliver along the line on the company’s brand promise. Frequent, quick successive meetings ensure the rapid flow of effective communication. Problems are solved without drama. There is no chaos in the office environment. Everyone is empowered to execute flawlessly to an array of consistently happy clients.


Everyone knows that growth burns cash. A rapidly scaling business faces the challenge of needing a scalable financial infrastructure to keep the company healthy. Our successful entrepreneurs pay close attention to finance as the heartbeat of the business, ensuring that everything else functions. They look at the tech they are using for financial management and for the ways that their financial systems can be automated so that they can be brought rapidly to scale. The capital to grow is another vital finance issue.

The best way to finance a business is through paying clients on the shortest possible cash flow cycle. However, when you are scaling up and making heavier investments in the resources you need for growth, it is likely that you will need a workable plan for raising capital. Our scale-up clients know the value of accessing innovative financial management that provides high level services to drive their business growth.

Navigating the scale-up journey of a growing private company is one of the hardest but most rewarding of careers to pursue. Having people in your corner who have been through this journey before helps take a lot of pain out of the process. No growth journey looks the same, but there are tried and tested methods that will – if applied diligently – lead to definite success. Happy scaling!

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