Business
Damon Woodward Reveals His Strategy for Scaling Real Estate Business Successfully

Damon Woodward is a high-profile real estate investor and the CEO of Leadway Holdings Ltd. and Blackcard University. Damon’s most recent deal speaks of his success. In October 2020, Damon purchased three apartment buildings with a total of 81 units, closing the greatest real estate deal in the history of Remax in Manitoba.
It took Damon a few years to achieve this great deal and expand his business. Now, he is more than happy to share his strategy for scaling a real estate business successfully.
The first thing that Damon wants to point out is that, “People and systems are what allow you to scale your business.” Damon strongly believes that one has to carefully choose who they surround themselves with, especially when it comes to their employees.
Damon chooses every single person who works with him, as he believes this is crucial for success. Damon makes sure to assess every member of his team carefully to determine their strengths and weaknesses. By doing so, Damon ensures that every team member is in the right position, can complete their tasks without any difficulties, and can build a successful career in Damon’s company.
“At this point, I’m quite aware of what I am good at and what I am not as good at, as well as what I enjoy doing and what I don’t enjoy doing. I have been able to find people I can rely on and trust in so that I don’t have to know everything,” Damon explains.
What is perhaps even more important than investing time and money in one’s team is perhaps investing in oneself. “The major difference between doing one deal and doing 12 deals is the mindset that is required. Mindset is not something that people learn by themselves; it has to be taught to them by hiring people who have already been there. These people can walk us through the process and expand our minds.”
Damon prefers working one-on-one with coaches and he hasn’t shied away from paying for the best. “I have spent over $100,000 on my personal development over the last few years, and every time I put a dollar in, I get to pull several dollars out. Hiring a coach to work with one-on-one is very important if you want to succeed,” Damon explains.
Damon also completed two programs at Blackcard University, the country’s number one real estate training company. Blackcard offers numerous programs to its students, ranging from one-on-one coaching sessions to programs such as ‘MI5’ or ‘Millionaire in 5 Years,’ which guides aspiring entrepreneurs to making a million dollars over five years.
Damon claims that the secret to his success is education and being surrounded by a world-class team he handpicked. He works with numerous coaches and consultants who teach him how to scale his business very quickly. In addition, Damon surrounds himself with the right people who can create adequate business plans and then execute those plans.
For more great tips and advice on real estate, make sure to follow Damon on Instagram (@damonwoodward3). Don’t forget to check out his YouTube channel, where he posts educational and daily-life videos regularly.
Business
Scaling Success: Why Smart Habits Beat Growth Hacks in Modern eCommerce

There’s a romanticized image of the eCommerce founder: a daring risk-taker chasing the next big idea, fueled by late-night caffeine and last-minute inspiration. But the reality behind scaled, sustainable brands tells a different story. Success in digital commerce doesn’t come from chaos or clever hacks. It comes from habits. Repetitive, structured, often unglamorous habits.
Change, a digital platform created by eCommerce strategist Ryan, builds its entire philosophy around this truth. Through education, mentorship, and infrastructure, Change helps founders shift from scrambling for quick wins to building strong systems that grow with them. The company doesn’t just offer software. It provides the foundation for digital trade, particularly for those in the B2B space.
The Habits That Build Momentum
At the heart of Change’s philosophy are five core habits Ryan considers non-negotiable. These aren’t buzzwords; they’re the foundation of sustainable growth.
First, obsess over data. Successful founders replace guesswork with metrics. They don’t rely on gut feelings. They measure performance and iterate.
Second, know your customer deeply. Not just what they buy, but why they buy. The most resilient brands build emotional loyalty, not just transactional volume.
Third, test fast. Algorithms shift. Consumer behavior changes. High-performing teams don’t resist this; they test weekly, sometimes daily, and adapt.
Fourth, manage time like a CEO. Every decision has a cost. Prioritizing high-impact actions isn’t optional; it’s survival.
Fifth, stay connected to mentorship and learning. The digital market moves quickly. The remaining founders are the ones who keep learning, never assuming they know it all.
Turning Habits into Infrastructure
What begins as personal discipline must eventually evolve into a team structure. Change teaches founders how to scale their systems, not just their sales.
Tools are essential for starting, think Notion for documentation, Asana for project management, Mixpanel or PostHog for analytics, and Loom for async communication. But tools alone don’t create momentum.
Teams need Monday metric check-ins, weekly test cycles, customer insight reviews, just to name a few. Founders set the tone by modeling behavior. It’s the rituals that matter, then, they turn it into company culture.
Ryan puts it simply: “We’re not just building tools; we’re building infrastructure for digital trade.”
Avoiding the Common Traps
Even with structure, the path isn’t always smooth. Some founders over-focus on short-term results, chasing vanity metrics or shiny tactics that feel productive but don’t move the needle.
Others fall into micromanagement, drowning in dashboards instead of building intuition. Discipline should sharpen clarity, not create rigidity. Flexibility is part of the process. Knowing when to pivot is just as important as knowing when to persist.
Scaling Through Self-Replication
In the end, eCommerce scale isn’t just about growing a business. It’s about repeating successful systems at every level. When founders internalize high-performance habits, they turn them into processes, then culture, then legacy.
Growth doesn’t require more motivation. It requires more precision. More consistency. Your calendar, not your to-do list, is your business plan.
In a space dominated by noise and novelty, Change and its founder are quietly reshaping the conversation. They aren’t chasing trends but building resilience, one habit at a time.
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