Omar de Silva first ventured into the business world by selling exotic lollies at school. Now, he has invented a new business school for entrepreneurs in the digital economy, which is turning the philosophy of learning upside down. He discusses his raw emotional journey through life’s ups and downs that gave rise to a very purposeful educational enterprise – The Plato Project.
John: Today I’m in Melbourne, in downtown Fitzroy. I’m joined by Omar De Silva. Omar is the co-founder and Executive Director of the Plato Project, a new business school driven to foster entrepreneurship and business leadership. The school here has the feel of a Japanese ski lodge, but I know this is not actually the school itself. It’s definitely a creative space, Omar.
Omar: John, it is good to see you. Thanks for the chat. It is definitely a creative space. It does have the feel of a Japanese ski lodge. This was not by design but by inheritance, though it’s a talking point if nothing else.
John: I’m still looking for the sushi and sake, but I hope that comes later.
Omar: I ordered it through Uber Eats; it is on the way.
John: After numerous business attempts growing up—some successful, some not—and working across the education, property, and professional services sectors, Omar now finds himself at the forefront of his industry. He is inspiring the development of the entrepreneurial ecosystem in Australia through his work. We’re going to discuss the Plato Project and all that it entails, but before we do that, you finished school and set your sights on being a professional golfer. Tell us about that.
Omar: The story goes that the first response I ever gave as a child to the question “What would you like to be when you grow up?” was apparently “God.” I was quickly told that wouldn’t happen. I then moved to Australian cricket captain and chased that dream quite hard. I played baseball and cricket, but golf was always there. It was for relaxation; it was something you could do all year. I fell into it by accident. My parents were divorced, and my dad would play golf on the weekends. I used to sit on his buggy while he pulled me around. I eventually got bored of that and started having a hit every now and again. I had some natural talent. As cricket and baseball competed for my focus, golf remained a constant, and it happened to be the sport I chose to pursue as hard as I could. I was good; I had the potential to be very good.
John: How long did you pursue golf, and how did that spark your passion for business?
Omar: I started golf at eight and began taking it seriously at fourteen or fifteen. I held onto the dream until I was about twenty. There were ups and downs during that time. When I finished school, I wanted to do some work to earn pocket money. I had some of my own businesses running in the background. They were intense and related to golf and other areas, but I wanted something more stable and consistent. I took a job at a golf shop and found myself in a Second-in-Charge (2IC) position quickly because the previous 2IC moved on. I had to run the business.
John: I’m going to back you up for a moment because there are a couple of things you said that need to be explored. First, you were running businesses in the background, and second, you were promoted at a young age. When did you start running businesses, and how old were you when you took over the 2IC role?
Omar: We will use the term “business” loosely regarding school. One of the first things I did was in Year 7 or 8. My dad, a hard worker, inspired me and taught me a lot. In the morning, while he was in the shower getting ready for work, I would take ten or twenty dollars from his wallet. I’m not proud of that, but I would take that money on the way to school, go to the milk bar, and buy lollies. Originally, they were meant to get the bullies off my back. However, I learned on the go that it was an effective “loss leader” into a business, which became selling lollies that you couldn’t get at school. Eventually, people became expectant of the lollies. I wielded power as the “lolly guy” who always had money to buy them. I started to charge twenty cents or a dollar and reinvested the money the next day. We went from there to selling cans of Coke from the supermarket and a broader range of exotic sweets. I ended up in a class called the Gifted and Talented Programme, which was actually just all the disruptive kids in one room to minimize disruption. We were taught how to trade shares on the ASX trading game, so I started putting real dollars into that. Given my interest in golf, I started running golf days for cricket clubs and businesses. I had connections with local celebrity golfers and good contacts at golf courses, so I secured a low cost base and charged what a club would ordinarily pay, allowing me to make a margin.
John: This was all while you were still at school?
Omar: It was during school, on weekends, and during holidays. I wasn’t a child prodigy working twelve-hour days; they were just side things. But it got to a point where I finished school, got my license, and had money coming in. At that stage, banks would lend you more money.
John: When was this?
Omar: This was roughly between 2004 and 2006, pre-GFC. Banks would lend me cash. I had money coming from various income streams. I would get a credit card and max it out, then get a personal loan to pay off the credit card. I’d pay off the card but not cancel it, so I would re-max the card and start all over again. I got myself into a nasty spiral. Part of the reason for the golf shop job was that I could see this happening and knew I needed to make as much money as I could, but I also loved being around golf.
John: It sounds like an accident waiting to happen, but you were also gaining an understanding of business. You were funding a lifestyle that was not sustainable, but in the meantime, you mentioned getting involved in a golf business and an online business connected to golf.
Omar: There were a few things going on. One of my greatest strengths and challenges is seeing opportunities and acting on them. Within the golf world, one of my mates was a pro playing in the US. He was personable and a great storyteller. At the time, lifestyle businesses weren’t common in every industry. We set up a business called Talking Golf, which was a hub for all things golf. He told the tales of a professional golfer in a fantastically Australian way, and it gained a lot of readership. That became the platform through which I started importing golf products under our own label and others. I eventually sold them to wholesalers and retailers. I sold through the golf club and golf days; wherever I could make a dollar, I tried to.
John: Was that happening in parallel with the golf shop job? You had gone “omni-channel,” as we might think of it now?
Omar: I had gone omni-channel. There was money coming in, which felt like a lot for a teenager, though in the scheme of things, it wasn’t. I was trying to maximize however I could. I would run golf days, sell the equipment for them, and connect people overseas with local golf trips, all while fulfilling my role in the golf shop.
John: You mentioned it was an accident waiting to happen. What occurred?
Omar: It absolutely was not sustainable. My dad grew up in poverty in Sri Lanka. He always instilled the values of budgeting in me. Throughout this time, I would budget, but only for the fortnight ahead. We discussed a family trip to Sri Lanka when I was about to turn twenty-one. As my birthday approached, the feeling of burden was strong. I decided it was time to take stock of where everything was. I had accounts with ANZ, NAB, Commonwealth, and Westpac. I tallied it all up. It was a very large red number staring at me. It was incredibly confronting because my dad had worked so hard to raise me, often on his own, and I had been an idiot. I owed a massive amount of money. I spoke to mentors, one of whom suggested I go bankrupt since I was young. We started that process, but as you may know, bankruptcy makes traveling difficult. Before executing anything, I decided to go on the trip to Sri Lanka. I saw all the places my dad had told me about as a child, and it was a huge perspective changer. Thankfully, the accident didn’t turn into something catastrophic. The perspective I gained made me decide to dig my way out of the hole slowly and steadily instead of declaring bankruptcy.
John: How did you do that? How large was the hole, and what did it involve emotionally?
Omar: It was very hard, particularly because I knew how much it would hurt my dad. I remember being out for a coffee with mates and realizing the three dollars and fifty cents was all I could afford to spend on anything other than food. It got to the point where I was eating cup noodles. I was going to Cash Converters to sell the Xbox and the screen from my car just to get by.
John: Did you refinance the loans and pay them off over time? How did you practically escape that hole?
Omar: There was a ridiculous number of accounts. We consolidated them. My dad gave me a hand, though not with a huge amount because I was only brave enough to tell him about a small portion of it. I made arrangements with various authorities and got to work.
John: It sounds like this is where your career truly began, as opposed to just funding a lifestyle.
Omar: That is right. I still need to work hard on being disciplined, but that perspective change was necessary. When I returned from Sri Lanka, I was still well-connected. I met someone who would become my business partner. He had a promotional merchandise and apparel business that was sitting dormant. One of the easiest things for me to do was take what I knew about business and sell it as a consulting service. I was helping people with their businesses because I enjoyed it and was good at it. I saw his business and realized it had a low barrier to entry. Rather than having him pay me, we went into business together to restart it. That business became quite successful; we ended up with clients like Disney, a big bank, and other large multinational companies. We both had an interest in property, so we pursued that as well. This sparked other interests, including a small travel product business where we experimented with identification items. It went okay, though it didn’t make a stack of cash. I started investing in property and did some small developments. I understood businesses and tried to do them well. The absolute majority of every dollar I made went toward paying off debts.
John: You are a serial entrepreneur by accident. At some point, you retired your debts and ended up in an interesting space involving purposeful thinking and mindfulness. You were a serial entrepreneur digging your way out of a hole, using life lessons constructively, but it wasn’t fulfilling. When did you realize your future lay elsewhere?
Omar: By 2012, I was out of the red and into the black. Everything I was doing served the purpose of making cash. In 2013, I had a difficult year personally; I lost a couple of friends to suicide. Luckily, I got married during that period, but I suffered from the cliché of being unable to get out of bed in the morning. That led me to ask questions of myself and my family, and I learned that several of my uncles had dealt with mental illness and had been hospitalized and medicated as a result.
John: That was only five years ago. What has happened between then and now?
Omar: I fell into education by accident during that period. A friend was asked to set up Uber when it first came to Melbourne, around 2011. At the time, he was teaching business at RMIT. In order for him to take the Uber role, he needed a replacement. I ended up teaching business at RMIT, specifically at the School of Fashion and Textiles.
John: So he could focus on Uber?
Omar: That’s right. It was last minute, so I had to jump in two weeks later.
John: Had you completed a tertiary degree yourself by this point?
Omar: I had studied, but I hated the system.
John: So you learned by doing. It is quite significant to be invited to teach in a tertiary institution. What happened next?
Omar: I found teaching incredibly rewarding. Some of my students started their own businesses and sent lovely emails saying how much they gained from the class. Instead of lecturing, I would open my laptop and we would go through real emails regarding customer complaints, suppliers, or purchases. That provided insight into applied learning, and the students loved the results. Later, the same friend who got me into education was working at another education startup specializing in diplomas. They wanted to move into higher education and needed someone to build that business. I decided that if I was going to do anything, I would be one hundred percent committed, or I would be out. This opportunity ticked a lot of boxes; I believed in education, entrepreneurship, and the chance to do something good. I set up that business and worked with the university to establish four Bachelor Degrees in Applied Entrepreneurship, Applied Social Entrepreneurship, Applied Management, and Applied Marketing. The word “Applied” was important because everything was driven by the application of theory. In the entrepreneurship degrees, you actually started a business as part of your degree. Every assignment was a building block for your own business.
John: Which university accredited this?
Omar: That was through the University of Canberra; the programme still runs.
John: What happened after that?
Omar: As I mentioned, I promised myself I’d leave if I wasn’t one hundred percent in. That started around 2014. About eighteen months later, the formal education system became too much to keep up with. We wanted education that was relevant, meaningful, and focused on outcomes. Unfortunately, the university system made making curriculum changes very difficult. I couldn’t honestly say those were the best degrees for starting a business anymore. My engagement started to wane, so I decided to leave. That was the catalyst for the Plato Project.
John: Let’s discuss the Plato Project. You mentioned purposefulness. What is the philosophy behind it?
Omar: First, that business education could be done better. Second, that social outcomes are as important as financial outcomes in the future of business. Third, the idea of mindfulness and not sacrificing your health and well-being for professional success. That conversation happened at the Merricks General Store in the Mornington Peninsula, and that was the start of Plato.
John: The Plato Project was founded in early 2016. What has happened since then? What does the organization do?
Omar: We position ourselves as the “new business school.” We are referring to “new” in terms of content, outcomes, and philosophy. We start with the idea that self-awareness, resilience, emotional intelligence, empathy, and mindfulness are the starting points for everything you do. Our programmes focus on personal leadership and being your best self to drive outcomes. We believe financial success shouldn’t come at the expense of social outcomes. We are happy to see that if you lead a purpose-driven business with an aspirational reason for being, you actually make more money these days. In a nutshell, we provide business education through “open programmes,” which are set curriculums for individuals or small groups. We also run these in-house for larger organizations, customizing the material to their needs. We sit at the midpoint of hard skills and soft skills. We don’t just teach how to build a product; we teach how to do it while bringing people on the journey, understanding the customer, and remaining empathetic.
John: Operating in the “new economy,” it seems there is a gap in the marketplace. Businesses like General Assembly have filled that gap because old education models have been flat-footed. What do you see for the future of the business?
Omar: General Assembly is a great reference point. When James and I first spoke, we admired them as a business. They specialize in hard technical skills like data science and coding, and we will likely never play in that space. However, we would like to have the same scale, impact, and influence they have, but from a business and leadership perspective. We have gone through iterations of growth and retraction. We are currently on a growth curve. We are constantly learning and making mistakes. Our vision is to be a global network of entrepreneurs and business leaders. That network piece is vital—learning from each other and tapping into the wisdom of the crowd. We want to be a global connector of fantastic educators and subject matter experts.
John: In concrete terms, what does that mean for the business? How many people do you employ, and what services do you deliver?
Omar: Everything we do has the customer in mind. If we don’t create educational offerings that provide real capability, we don’t have a business. To get the products right, we need to know our customers better than they know themselves so we can offer development that ensures future success. Practically, it looks like a university offering various learning programmes, but we are less focused on the “gold stamp” at the end and more interested in the capabilities developed throughout. I don’t think staff size is a relevant metric for our business, or perhaps any business anymore. I don’t mind how big the team gets as long as everyone is adding value and having rewarding careers. Our biggest challenge will always be scale. I believe the best educational outcomes come from direct interaction, preferably face-to-face, which presents challenges for scaling. We won’t sacrifice the outcome or the need for meaningful interaction, but we need to figure out how to use technology to do that on a global scale. Education has a leveraged impact model; if you successfully influence one person, and they influence five others, you have impacted six people and beyond.
John: Businesses increasingly have globally distributed workforces, and the traditional idea of employee and employer is changing. How does your business model stitch together and scale with the right tech platform?
Omar: We run courses that start on certain dates and run for six to eight weeks. We also deploy those programmes in-house at organizations anytime. As long as there is a great person to deliver the material anywhere in the world, the business can operate. Recently, our team was on a retreat, and we realized we don’t need to be in an office; we only need to deliver outcomes to our students. We don’t know exactly what the future looks like. One of our partners, Who Gives A Crap, is a social enterprise that is entirely remote with a team of about thirty. Shopify is also entirely remote. I don’t think there is any reason we need to be in front of each other every day. That said, face-to-face interaction is powerful for learning and collaboration. I would like to think we end up with half a dozen flagship campuses around the world that serve as landing pads for global entrepreneurs and students. Combined with powerful online learning experiences using holographic projections, we can create the same experience traditionally found on campus. Somewhere in the middle is where our business will live.
John: Omar, it is a very interesting journey. I look forward to checking in on it in a couple of years. Thanks for being part of Customers Matter today.
Omar: Thanks for the chat, John. I appreciate it.