TheBucket

I had the benefit of humble beginnings, growing up in the town of Wagga Wagga in a working-class family with both of my parents being public school teachers.

As the oldest of four children, my three brothers and I attended the local public schools for both primary and secondary education. While my parents didn’t have a lot of cash, they always managed to provide enough to keep clothes on our backs and food on the table. We wore a lot of hand-me-downs, drove 30-year-old cars, and went on one family holiday a year to visit relatives on the Central Coast. Unlike my own children, who go on multiple overseas holidays every year, our annual holidays were at the local caravan park and I didn’t experience international travel until I was 19.

I definitely inherited my entrepreneurial spirit from my father, who always had a few income-generating side hustles outside of his teaching job. These ventures ranged from ongoing share trading, a hobby farm business (which provided great tax breaks), a venison farm, a lawn mowing business, and even a weekend paintball business.

Not only did these businesses provide additional income for the family, but they were also prime opportunities for my brothers and me to work in. Between school and sports commitments, we would spend countless hours each week helping our father, allowing us to earn an uncapped weekly allowance while spending quality time with him.

My father was always a contrarian thinker, making investments that most people would never consider he would “zig why everyone else zags”. One of his most profitable moves was purchasing a 50-acre block of land on a hill overlooking Wagga in the early 1980s. The land was landlocked by surrounding farms, requiring him to build a causeway over a gully, construct a 1km road, and pay to have utilities extended to the property. Friends and family thought he was crazy, but he was focused on long-term potential. He knew the largest property developer in Wagga owned the land around it but was struggling to come up with the $30,000 needed to buy the block. My father, “seeing the forest through the trees” seized the opportunity, and 25 years later, sold the land to that same developer for nearly $2.5 million—allowing him to retire 10 years earlier than most school teachers.

When I obtained my driver’s licence at 17, my father partnered with me in the lawn mowing business, which allowed me to save money for university. This was my first business, which I operated until I started my university studies. It felt exhilarating driving around in my 1967 HR, being in control of the work I did, effortlessly meeting my clients’ expectations, and earning hard cash in return… a feeling I would never forget.

University

I completed a double degree in Actuarial Studies and Commerce at ANU in Canberra. Within a month, I knew I wouldn’t pursue a career as an actuary because I found the classes mind-numbing. However, I’m not someone who quits, so I continued with both degrees and completed them over four years.

The real value of university was that it got me out of Wagga Wagga and exposed me to people from across Australia and the world. I was introduced to new experiences—travel, food, entertainment, and financial opportunities. I attended the compulsory tutorials and any class scheduled before a uni bar session. Most of my time was spent hanging with mates, chasing girls and working multiple jobs, including an early morning daily delivery bread run I’d share with mates, tutoring at my colleague, and working at the colleague as a handyman’s assistant. I also took advantage of government grants, which helped cover my accommodation and fund adventures in holidays across Asia.

A lot of trips ended up in Bali which is where I learnt a valuable lesson about Capitalism “It is called capitalism because wealth comes from putting capital to work not labour.”

We were picking up necklaces and bracelets in Bali for around 5 to 15 cents each and bringing a few hundred back to Canberra. On Thursdays, we’d spread out a hammock sheet at the uni markets and sell them for $10 to $20 each, easily making $150 to $300 per week. Our success depended largely on the weather and how long we could stay before getting kicked out for not paying the weekly stall fee!

Although I didn’t take my studies too seriously—often cramming a semester’s worth of material into two weeks before exams and forgetting it all afterward—I had an incredible time at university. I picked up valuable life skills, and even took up snowboarding, as Canberra was just a few hours from the snowfields. It was definitely one of the highlights of my 20s. I met some amazing people, many of whom remain some of my closest friends today.

Post-University

After graduating, one of my closest friends at university was due to return to Bogota, Colombia after Xmas. After a long night out, he suggested that kebabs would be a hit in Colombia, as none existed there. I thought it sounded like a wild adventure, so after Christmas, we embarked on a trip to South America, with stops in Asia and Europe. Typically, friends and family thought I was crazy about moving to Bogota, but I didn’t care these were just their conservative opinions – as we know………. opinions are similar to a$#hol** in that everyone has one”.

Our time in Europe was tough on a tight budget, but it fueled my determination to return one day as a millionaire and do it in style.

When we arrived in Bogota, we set out to create a kebab shop. Despite language barriers and a general lack of resources, we managed to have a rotisserie custom-made and sourced ingredients locally. The business was breaking even, but after six months, I had racked up $20,000 in credit card debt and decided to return to Australia. While a few years later I eventually recouped my capital when the business sold, I learned a valuable lesson: the restaurant business is capital-intensive with long hours and tight margins. From that point, I decided to avoid hospitality and retail ventures in the future.

Working as an Employee

Upon returning to Australia, I moved to Sydney and needed a job fast to pay off my debts. I always had an interest in derivatives trading but ended up landing a role as an assistant accountant for a PR company. Over four years, I completed my CPA, paid off my debts, and built a comfortable life in Bondi with my partner, Morgan. However, I started to feel trapped by the 9-to-5 grind, wearing a suit every day and being accountable to someone else.

At that time, tech startups were booming, and I knew I wanted to start my own venture. So, I opened up the Yellow Pages (after I found it being used as a pot-plant stand) and began scanning through different industries and sectors. I kept noticing businesses in the real estate space and realised that real estate, as an asset class, affects everyone and would always benefit from strong, consistent demand “it would have ongoing tailwinds supporting it”. That made it seem like the perfect opportunity to pursue.

Pivoting into Tech

Renting a property in Sydney’s Eastern Suburbs wasn’t an ideal experience. You’d go to the first open home only to find 30 or more other couples all vying for the same shabby 1940s-style two-bedroom apartment. You’d then submit your application, only to learn the property had already been snapped up immediately after the inspection. The process felt broken, and I thought, “Surely, there has to be a better way.” That’s when the idea for “RentalBids” came to me—a platform where prospective tenants could input their ideal rental terms, including the rent amount, term, pets, and other criteria, to help secure a property. 

To validate the idea, I interviewed property managers, who had mixed reactions. Some saw potential in the service, but others felt it might overcomplicate things. Still, I was determined to pursue the concept.

I didn’t know anyone in the tech space, so I began researching who the key players were in real estate technology. As luck would have it, I found someone in South Bondi, literally around the corner from where I lived. We agreed on a price, and he began building the platform. I had saved $20,000 and my parents had gifted me $25,000 to pay off my HECS. I viewed HECS as a cheap government loan so didn’t pay it off and embarked on my new startup life with $45,000.

However, after a few months, the project was dragging, and I had already resigned from my accounting job. My developer, Peter, asked me what I planned to do with my time. I told him, “Hang out and surf.” He suggested I join him at his company, Agentpoint, as a project manager. I had no prior experience in tech or digital, but Peter reassured me that he would teach me everything I needed to know. 

Peter wasn’t a coder, nor a particularly strong businessperson, but he was an excellent salesman. I decided to join him, and within a few weeks, I was managing project briefs, meeting with new clients, and overseeing project management for existing ones. What I learned early on was that it doesn’t matter if you don’t know everything, as long as you know more than the clients you’re dealing with. Most of our clients were small businesses, and tech was still relatively new to them. This allowed me “to fake it until I could make it”, and soon I gained enough experience to understand more than they did.

As I started taking on more responsibility at Agentpoint, moving from working one day a week to five, Peter approached me with a new business idea. We would set up a digital agency that would list private sellers’ properties on Realestate.com.au and Domain.com.au, routing inquiries back to the sellers. Peter provided the tech, and I ran the business. I became the face of Vode Property and quickly realised I needed a real estate licence to list properties on Realestate.com.au. 

I completed an online course in a few weeks (which felt absurdly easy) and was now a licensed real estate agent. My job was to scour private-selling websites, cold-calling owners to convince them to list with our service. Cold calling was tough and this is where I learnt a valuable lesson around resilience “If you avoid failure, you also avoid success” which is a core attribute for any startup or business founder. I ended up having some success and managed to grow the business, generating $60,000 to $70,000 in revenue within a year. I learned the importance of overcoming objections as private sellers really dislike real estate agents, so you have to be persistent. I also learned the immense value of excellent customer service and how referrals can drive new business.

While I was running this business, I was still working for Peter at Agentpoint. Unfortunately, my “RentalBids” business stalled when Peter expressed doubts about its viability, citing new legislation that would likely ban rental auctions. That was a blow, especially since I had invested $30,000 into development, and all I had to show for it was a shell of a product. However, I was too busy with Agentpoint and Vode Property to care much at the time.

I was enjoying working at Agentpoint and could see how I could make a new career in the tech space, so I approached Peter around buying into his business. He was open to this and greed on a $75,000 investment, i $30,000 I had already spent on the RentalBids project, plus an additional $45,000 in cash. We sold Vode Property to a client for $40,000, knocking another $20,000 off the bill. For the remaining $25,000, I agreed to work for free for five months.

Running Agentpoint

A few months after our deal, Peter began talking about expanding Agentpoint into the U.S. His brother lived there, and Peter had always wanted to move there. He proposed that he handle the U.S. expansion while I stayed in Australia to run the local operations. I wasn’t opposed to this, so we agreed on a three-month transition plan. After that, Peter would be based in the U.S., and I would take full control of Agentpoint in Australia.

During this transition, I started to dig into the business’s cash flow. That’s when I discovered that our three contractors (designers and developers) were between two and four months behind on their wages. I also uncovered a number of maxed out credit cards and realised his Jeep Wrangler had been purchased on credit in the company’s name.

Peter’s vision for the future of the business was quite different from mine. I had a “never give up” mentality, especially after investing $75k into it. Peter, on the other hand, was ready to move on and even suggested we consider shutting down the company if we couldn’t cover the bills. He left for USA, seemingly unfazed by the chaos he was leaving behind.

I was left thinking, “What do I do now?” I calculated that Peter and Agentpoint had around $140k in credit card and outstanding staff wages. I hadn’t drawn a wage in four months, and fortunately, Morgan’s government job covered our rent and groceries. Things were so dire that I applied for a data administration role at DiJones, a local real estate agency. Thankfully, they declined me because I had no experience with real estate CRM systems—what a loss for them!

I decided to soldier on with Agentpoint instead. I negotiated a payment plan with the staff, sold Peter’s Jeep, and eventually paid down the Agentpoint credit card debt over nine months.

In the process, I analysed our cost base. We had no office, and the main expenses were servers and Australian-based contractors. I thought, “I’ve never met these contractors—they all work from home. Why not look for cheaper contractors in developing countries?” That’s when I turned to Odesk (now Upwork) and began experimenting with developers in other countries:

• Serbia/Croatia: Reasonable pricing, good engineers but terrible time zone.
• India: Expensive, ok engineers and terrible time zone.
• Philippines: Good English and time zone, but poor skills.
• Vietnam: Reasonably priced with decent skills, but not great English.
• China: Hard to communicate with and mid-priced and ok skills.
• Indonesia: Good time zone, super cheap, and decent communication.

I eventually landed on Indonesia, where I found an incredible supplier named Yulianto. I remember receiving a quote from him for $1,050 to build a website that would generate $11,000 for Agentpoint. I almost fell over when reading the quote and had to confirm we were talking about the same website. He assured me that everything was included, with a warranty. This experience brought back memories of my Bali arbitrage days, but this time it involved labour and time, which was even more valuable. This moment was a turning point for Agentpoint, and I replaced the onshore team with an offshore team. From that point forward, Agentpoint was profitable for the next 10+ years until its sale.

Agentpoint Path to Exit

While Agentpoint became profitable, it required long hours— often 12 to 15-hour days. This took a toll on my health, my relationship with Morgan, and my friendships. Despite the challenges, we built Agentpoint into Australia’s leading provider of real estate websites. We also successfully launched the first Facebook real estate products in Australia and developed ProposalPoint, the first-to-market digital proposal software for real estate agents. We became a pioneer in real estate tech and a go-to expert in Australia’s proptech space.

In 2016, I renegotiated my equity stake with Peter, and we merged with another business, Boatdeck, which provided a similar service for the marine industry. By this time, although we had a team of around 10 in Australia and 30 staff offshore I was exhausted from being a solo operator and wanted to step back from the business. The merger allowed me to share the workload with two other founders of Boatdeck. Additionally, a slick-talking investment banker had convinced us that rolling up small tech businesses could lead to an ASX exit. Well that didn’t happen and that is where I learned “You can’t make a deal with a bad person”.

In March of 2021 we eventually closed on the sale of Agentpoint to a private equity-backed (AKKR) CRM organisation from the UK, and 12 months later, we sold Boatdeck to Yatco, a Miami-based marine CRM system.

These exits were a long time coming and brought much-needed relief after years of hard work and frustration. Along the way, I learned many valuable lessons. If I had my time again, I would do some things differently, but I hope that sharing my failures and lessons learned can help others on their journey to success.

At that time, Morgan and I had built some wealth through investments in crypto, private companies, and real estate. However, the sale of these two businesses significantly amplified our financial position and set us on the path toward transforming it into multi-generational wealth for our children and future generations.

Without Morgan’s unwavering financial and emotional support over the years, there’s no doubt we wouldn’t be where we are today. When the demands of the business consumed so much of my time, Morgan made the significant sacrifice of stepping away from her career to focus on raising our two boys, Asher and Ezra, while also supporting me in Agentpoint and our private investments.

She’s the ultra-conservative voice that perfectly balances my optimistic, risk-taking, all-in approach to business and investing—a perspective I’ve come to appreciate and refine over time. Together, we’ve been a successful and dependable team.