Gary Tramer’s wild entrepreneurial ride

If there is one word to describe Gary Tramer, founder of companies like LeadChat and PoweredLocal, it is enthusiasm. This business owner is oozing with energy, and his vibe extends to his colourful entrepreneurial journey. His journey is an adventure filled with ups and downs, but Gary finds joy and excitement going through the peaks and troughs of the entire experience.


Gary’s business journey is a wild escapade full of learnings. He has started a business, grown a business and sold a business. There are some failures as well, but in each mistake and win, he picks a valuable lesson every step of the way. It began from his own home, as he ascertained through his family about how he would fare as an entrepreneur.

Although he didn’t have entrepreneurial parents, he still acquired a lot of insights from them. Too bad that he didn’t learn too much from his grandfather, who owned a shoe company, because his granddad passed away before Gary even started with his career in entrepreneurship. However, seeing his dad, a retired dentist, work hard from 6:30 in the morning until 7:30 at night, six days a week, Gary realised something important. What he saw made him decide what he didn’t want to happen to him when he would start working. “I didn't want to have that work ethic. I didn't want to not see my family so much during the week. I didn't want to be stressed out. I didn't want to follow the same path. I wanted to be successful but can enjoy my lifestyle and spend time with the family when I have one,” he opined.

Studying in a Jewish school and growing up in a Jewish community, Gary knew of people and friends whose parents or grandparents owned popular shopping stores and huge brands, such as Chadstone Shopping Centre, Spotlight Fabrics, Anaconda, Peter Alexander pyjamas, and Nando’s. He recalled, “I always remember growing up and going to a school where we recognise success from a very young age. I grew up in an environment where the parents of my friends were employers of very successful companies or doctors or lawyers.“

As a kid, Gary already had the entrepreneurial spirit within him. “In primary school, one of my best friends, his name is Michael, we lived very close to each other, probably three or four streets away. We were on the same school bus. He and I, from probably seven or eight years old, were already starting our entrepreneurial career. We were going around the neighbourhood, stealing pot plants from our neighbour's garden, putting them into yogurt cups, selling them back to the neighbours, and then using the money to buy lollies from the corner store, the milk bar. We were buying those lollies and reselling them on the school bus for a profit as well. I think that was the first real lesson of turning nothing into something,” he enthusiastically narrated.

His friendship with Michael has grown through the years that they have become co-founders in most of the businesses they established. However, his first venture was not with this business partner. When he finished school, Gary decided to take a year off and travel around the world. He went to Israel in the Middle East and around Europe. When he came back, he wasn’t sure what he wanted to do, so he enrolled in a course, called behavioural neuroscience, which is part psychology and part medicine. “During those three years, I came to understand that the academia and the professional world weren’t for me. I like to craft my path. Then, it was during that time that I set up my first business,” the energetic entrepreneur quipped.

While studying for his neuroscience degree, Gary was fascinated with becoming a DJ. He pursued his passion, but things didn’t turn out well. Gary explained, “I always wanted to become a DJ because they had all the adoration of all the fans. So, I bought turntables and spent thousands of hours in the cabana, our pool house, learning how to play music and DJing. But it was quite hard to get booked as a DJ. I couldn't get a gig. My next step was how to get a gig. I thought, ‘maybe I should start my rave company, put on my shows, and then book myself as a DJ at parties I organise.’ It sounded like a good way to start my career.”

To do that, he borrowed about $10,000 from his dad, which was already an insane amount when he was only 18 or 19 years old. His supportive father gave it to him as a loan, not as a gift, so he worked hard to grow the money. While he did it, he also rented sound systems and lights from his friend, Michael, who was running an audio-visual company at that time.

Long story short, Gary lost his dad’s money in that rave business he put up. That was the lowest of lows that he has experienced during his entire journey. But it taught him something. “We lost almost all the money because not that many people turned up. That was the first real lesson about poor marketing and not marketing well enough. So, booking everything in advance, paying for everything in advance, and then not having the performance that we wanted, we ended up losing a lot of money,” he pondered.

The incident caused a lot of stress on Gary. As he was also working in a gaming bar at that time, he started calculating how many hours he needed to work so he could recoup the amount and pay his dad. He realised the real pain of being an entrepreneur is taking risks. “You can take a risk, and you can make it big. But quite often, you can also lose big. We decided that we had two options. One is we shut down and go back to our jobs. Another is we leverage from our previous events, since we had a bit of a name for ourselves, and do another event differently.”

Not giving up, Gary chose the latter. For their next event, he re-negotiated with suppliers, marketed the event strategically, and opted for things that required little or no risks. They didn’t pay upfront, told the suppliers they would pay them a percentage if the event turns out well, asked for discounts from suppliers, and did a secretive promotion. It became a huge success. They put the money straight back to the next event, and it continued for about five to six years. But he also got into another realisation that the kind of business he had was in a very tight industry with no predictable revenue. He then moved on to other ventures.

The next enterprise was on selling. It turned out that Gary did well in door-to-door sales that he ended up owning and running a company that was selling credit cards. While earning on a commission can bring predictable revenue, it didn’t produce repetitive returns. “It was a great cash flow business because you get paid on commission for every sale that you did. But one of the lessons I learned there was that you are only making as much money as your last sale. You have to keep selling to pay for the bills. However, I learned a lot about recruiting, managing, training, motivating and retaining sales staff. By 2009, I was so burnt out. We lost a couple of key clients. I decided that I didn't want to do it anymore. In the end, we shut the business down. It took about a year for me to find what I wanted to do with my next thing,” he disclosed.

There were other ventures after that where he was able to start, build and sell a business. He also consulted for Michael’s business until they decided to join forces and got involved in technology start-ups. Gary admitted that not all businesses they established flew. There were some that failed, while there were side projects that became a huge success. One thing led to another until they both founded LeachChat and later PoweredLocal.

Based on his experience with the rave company, what scared Gary the most was the idea of cash constraints. That is why they now try to mitigate putting money in any venture they start. They endeavour to engineer their businesses to be cash flow positive with recurring revenue, such as subscription businesses. But for Gary, the biggest challenge to an entrepreneur or business owner is not being able to understand the important parts of the business while starting out. What he meant by that is to learn the various aspects of running the business like HR, marketing, online processes, sales or product development. Even if one hires an expert, it is still necessary that the business owner has an idea of the deliverables. He found that it is difficult for a business owner if he does not know anything about any of these business features as it will bring gaps to managing the entire enterprise.

After learning the different facets of entrepreneurship, Gary has applied best practices that enabled his current businesses to last this long. “We have a build-first-sell-second mentality. What we mean by that is that we don't invest time and effort into a product before we can prove that customers are willing to buy. Often, we are selling something that doesn't yet exist. So, you imagine, how do you do that? It's picking up the phone. It's walking into a business with maybe a brochure and a website that you've created, even though the product doesn't even exist in the world, yet. We never hire staff before we've got a model that can make money proven. So, Michael is with the product, while I'm involved in sales,” he detailed.

Furthermore, Gary is thankful he found EO Melbourne because it also helped him in improving his business and himself as an entrepreneur. Not only did he pick tools and tips in managing an enterprise, he also learned things that helped in his self-development. Gary expounded, “The first thing is the realisation that everybody has problems. And often, everybody's problems are worse than your problem. The other big lesson is understanding all the other business models that are out there, all the things that you learn about other people with businesses, and how they work. When you think about a business or what makes a good business, forget the product or the service, there's a lot of criteria to consider. I find it interesting because we have a very specific way in which we like to build businesses, and EO Melbourne has been a good validation for that. I think the other thing that's been amazing from EO is the personal lessons more so than the business. These are learning lessons about how entrepreneurs get the most out of their lives. And I've taken a lot out of those as well.”

Still, the struggle of entrepreneurship never ends, especially that business owners never switch off. According to Gary, they never really go home from work. Although they physically leave their offices, they still carry the responsibility of looking after the business wherever they go. There is the flexibility to work on hours that suit their regime or go on holidays on days they choose, but they have to deal with problems whenever something comes up because the buck stops with them.

On the other hand, Gary finds the entrepreneurial route extremely satisfying. “I think the biggest reward for running your own business is you get a lot of freedom once you master the work-life balance. When my kids are sick, I can be home without having to ask anybody. If I want to go on a holiday for a month or be in another country, I don't have to ask permission. But I consult with my business partner Michael before I go. Once the business goes well, there is a sense of financial freedom, although making money is certainly not the reward. I think the reward is the choices that you get to make, once the businesses are performing at a certain level,” he pointed out.

With a goal of retiring financially by the age of 40, Gary hopes to bring his businesses to greater success in the years to come. He is also looking at teaching, whether teaching kids or mentoring entrepreneurs. He also wants to support his wife, who had spent the best part of seven years bringing up their kids and sacrificing her career, in whatever she wants to do.

Indeed, Gary has learned so much from his colourful entrepreneurial adventure that he can pass on a lot of insights to those who are still starting out in their journey. For him, the two key skills that people who want to be successful entrepreneurs should master are selling in the real world and selling online. “When I say master, it means invest all your time and effort into these two things. If you can do that, you can start any business,” stated the passionate business owner.

Since many resources are now available at the tip of one’s fingers, Gary believes that anyone can have the capability to become an entrepreneur. There are risks and sacrifices, but with determination and passion, a business owner will enjoy the experience as Gary did. Because he loves what he is doing, he sees his business journey as a wild ride that is full of challenges and learnings. There may be mistakes and failures along the way, but Gary showed that success comes when one never gives up and continues to forge ahead towards the goal.

Know more about Gary Tramer through his LinkedIn profile. More on LeadChat at  and PoweredLocal at