*]:pointer-events-auto R6Vx5W_threadScrollVars scroll-mb-[calc(var(--scroll-root-safe-area-inset-bottom,0px)+var(--thread-response-height))] scroll-mt-[calc(var(--header-height)+min(200px,max(70px,20svh)))]" dir="auto" data-turn-id= "request-6a7495ae-8138-83e8-af4d-0964d8c65345-9" data-turn-id-container= "request-6a7495ae-8138-83e8-af4d-0964d8c65345-9" data-testid= "conversation-turn-16" data-turn="assistant"> Wayne Hillier Before Real Estate: Debt, Gambling & Rock Bottom Before the rental properties, businesses, coaching and real estate investing success, Wayne Hillier was living a very different life. He was working at a gas station for roughly $14–$16 an hour, carrying credit-card debt, gambling, trying to keep up with friends who were progressing in their careers, and feeling increasingly stuck. Then one weekend, Wayne bought a sports lottery ticket. For several hours, he believed he may have won approximately $340,000. What happened next became one of the pivotal moments that eventually pushed him to leave Ontario, move across the country to Alberta, meet Gabby and ultimately discover real estate investing. It is a chapter of Wayne's story he says he had almost completely forgotten — and had never shared on the podcast before. The lesson that came from it would eventually shape much of what happened next: No one is coming to save you. 🧠 What You'll Learn What Wayne's life looked like before real estate investing Why his original plan to become an accountant fell apart What it felt like watching friends move ahead while he remained stuck How debt and trying to keep up with others affected his decisions Why gambling became part of that period of his life The Proline Pools ticket that made Wayne think he had won approximately $340,000 Why the result turned into only about $350 How Wayne lost that money shortly afterward playing online poker Why that experience became part of his rock-bottom moment The late-night conversation that convinced him to move to Alberta How one decision led to another and eventually led Wayne to Gabby Why small decisions can completely change the trajectory of your life Why money alone would not have fixed Wayne's problems at that stage Why education eventually became more valuable than luck How Wayne went from making bad decisions to deliberately making better ones Why knowledge changes what you are capable of doing with money Why action matters more than waiting for something to rescue you Before Real Estate, Wayne Was Stuck Wayne says he has told the story of how he got into real estate investing hundreds of times. Usually, the story starts with him leaving Ontario and moving to Alberta. But today he realized there was an important part missing. Around 20 years ago, Wayne was in his early twenties and had effectively abandoned his original plan to go to school and become an accountant. He had paid for school and had a plan, but the path did not feel right. He talked to people already working in accounting and realized that the life he was building toward was not the life he wanted. The problem was that once he walked away from that plan, he had no replacement. He was working at a gas station, making close to minimum wage, while many of his friends were progressing through the trades, earning more money, buying cars and moving forward. Wayne felt like everyone else's life was moving while his was standing still. Debt, Gambling and Keeping Up Instead of solving the bigger problem, Wayne started trying to keep up. His friends were earning substantially more than he was. They could afford the bar. They could afford the casino. They could afford nicer cars. Wayne could not. That led to increasing credit-card limits and spending money he did not really have. The casino became part of the routine. Online poker became another outlet. Wayne says he was actually a decent poker player, but a terrible gambler. He could win repeatedly and then lose everything by increasing the stakes. That was the pattern. Win. Get confident. Bet bigger. Lose it. The $340,000 Ticket One of the gambling activities Wayne and his friends regularly participated in was Proline Pools. They would select the winners of a group of NHL games, and everyone who correctly picked every game would split the prize pool. Most weeks, Wayne remembers there being only one, two or maybe three winners. That meant the payouts could become very large. One weekend, Wayne got almost everything right. By the final night, only a few games remained. One by one, his picks won. Eventually it came down to the final game. The team Wayne had selected fell behind badly. He basically gave up on it. Later, the game became close again. With very little time remaining, the team he picked scored and won. Wayne had selected every game correctly. The prize pool was approximately: $340,000. For a Few Hours, Wayne Thought His Life Had Changed At the time, Wayne was making roughly $14 an hour, working limited hours and carrying debt. Suddenly he believed he might be about to receive life-changing money. He started imagining what that money could mean. He thought he had bought himself years of freedom. He did not have a real investment plan. He did not know anything about real estate investing yet. He simply thought: I finally have options. But the official results did not appear. Wayne kept refreshing the website. Nothing. He eventually went to sleep. He woke up early. Still nothing. Then he had to go to work. This was before smartphones were common, so Wayne spent most of the day wondering whether he had just won hundreds of thousands of dollars. From $340,000 to $350 When Wayne finally checked the results, he understood why they had taken so long to process. There were not one or two winners. There were more than: 800 winners. His portion of the approximately $340,000 prize pool was roughly: $350. The emotional swing was enormous. For hours, Wayne believed life had finally handed him an escape. Instead, he received a few hundred dollars. The Spiral Got Worse That was not quite the bottom. Wayne then took the money and entered an expensive online poker tournament. For someone making roughly $14 an hour, spending hundreds of dollars on a single poker tournament was a major risk. He played for hours. He finished just outside the payout positions. The money was gone. The imagined $340,000 was gone. The $350 was gone. Wayne says he nearly threw his computer monitor through the wall. That week forced him to face something he had been avoiding: His life was not going to change because he got lucky. "No One Is Coming to Save Me" Wayne describes this as one of the moments when he realized: The world was not going to take care of him. The lottery was not coming. Nobody was going to arrive and fix his life. If something was going to change, he had to change it himself. That realization led to another decision. Late at night, Wayne drove to the gas station where another employee was working. That employee had previously moved to Alberta and had done well financially before eventually returning to Ontario. Wayne stayed there for hours asking questions. What was Alberta like? Could he find work? How much money could he make? Where would he live? How would he get there? What would he need? Less than a week later, Wayne loaded up a U-Haul and drove across the country. One Decision Led to Another That move changed everything. Moving to Alberta eventually put Wayne in a townhouse complex across the walkway from Gabby. Then another small decision changed his life again. Wayne happened to work overtime one day. Instead of arriving home at his usual time, he got home later while Gabby was celebrating her birthday. Someone invited him over. Wayne said yes. He met Gabby. They have been together ever since. None of those decisions looked life-changing in the moment. Taking overtime. Talking to a coworker. Moving provinces. Choosing one rental property. Accepting an invitation. But each decision moved Wayne in a different direction. Together, they completely changed his life. What If Wayne Had Actually Won the Money? During the episode, Wayne asks an interesting question. What if he really had won the $340,000? His conclusion is that the money probably would not have saved him. At that point in his life, he did not have the knowledge, discipline or experience to use it properly. He believes he probably would have spent it. He may have gambled more. He may have bought expensive things. And eventually he may have ended up in exactly the same position — just later. That is the important distinction. Money alone does not create wealth. You need to know what to do with it. Knowledge Changed Everything Today, Wayne says if someone handed him $340,000 and asked what to do with it, the situation would be completely different. Now he understands: Cash flow Return on investment Risk Financing Property selection Market fundamentals Asset management How to deploy capital intelligently That knowledge came from years of reading, coaching, education, experience and actually investing. Wayne's biggest asset was not getting lucky. It was becoming the person who knew what to do when opportunities appeared. The Main Lesson If you are in a difficult place right now, the message from today's episode is not that everything changes overnight. It usually does not. Start with one decision. Ask a question. Learn something. Talk to somebody who has already done what you want to do. Stop waiting for the perfect opportunity. Stop waiting for luck. Stop waiting for somebody to rescue you. Wayne went from making bad decisions to making better ones. Those better decisions eventually led him across the country. They led him to Gabby. They led him to real estate investing. They led to businesses, investments and opportunities h
