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The Five Things Holding You Back from Real Estate Success

What are your biggest passions? What gets you excited each day? For our guest on episode 22 of The Executive Real Estate Investing Show, Trevor McGregor, it’s all about real estate and coaching people. He loves the diversity, challenge, and excitement of real estate investing, and equally loves helping others experience the same thing and go after their dreams and goals.

Trevor is a high-performance master platinum coach and real estate investor. This work allows him to follow those two passions: people and real estate. He is a believer in diversification, and so has real estate ventures in everything between single and multifamily homes to storage units, agricultural farms, and international investments.

After helping thousands of clients get into real estate and grow their businesses, Trevor has some valuable insight and tips for us. In this episode, he shared the five things that hold people back from success in real estate. We’ll look a bit at Trevor’s background and history and then jump right into those roadblocks and how you can overcome them.

Trevor’s story: From real estate to coaching

Trevor McGregor
Trevor McGregor

Trevor’s work as a coach is all about walking alongside people and helping them get to where they want to go. Coaching is about co-creating a life that the client wants to achieve—you can’t do it for them, but, instead, show them the path forward. Trevor says there are two parts to being a coach: one is helping with the mindset and motivation aspect, overcoming limiting beliefs and doubts. The second piece is about strategic planning and working through the details of specific real estate investing moves.

As far as coaching credentials go, Trevor’s are pretty impressive. He became a certified Tony Robbins master platinum coach, completing his training in Florida. He then went on to work with the man, the myth, and the legend, Tony Robbins himself, for half a decade. Afterwards, he branched out and started his own company, successfully coaching thousands of clients from all over the world.

Alongside his coaching business, Trevor is involved in a variety of real estate ventures. He’s currently involved in single-family homes in Vancouver, Canada and multifamily homes in Austin, Texas. Besides that, he’s invested in a 1900-acre hemp farm in Colorado, self-storage units in Florida, and other investments in Costa Rica and Australia. Talk about diversification! Trevor believes that diversification is key, both from a financial perspective, but also in that you can expand your network and continue to grow a business.

His hands-on experience with a variety of real-estate investments has allowed him to grow his network and interact with a wide variety of clients. This, in turn, gives him the expertise to really help people who need an extra push in their real estate investing and entrepreneurial journey.

Five things holding you back from success in real estate investing

This depth and breadth of experience has allowed Trevor to collect some pretty valuable insight on what can make or break someone’s journey into real estate. He has worked with thousands of clients, identifying the top five reasons fail in real estate: limiting beliefs, lack of a strategic plan, lack of systems for support, poor time management, and a lack of execution and accountability.

These mistakes can hold anyone back. It doesn’t matter where you are on your journey, there’s always another level. And, if you want to scale, you need to look at these things that are potentially holding you back. Let’s look at each one a bit further in-depth.

1.     Limiting Beliefs

Limiting beliefs are probably the top roadblock that holds people back from success. So many people are afraid to make a move because they don’t want to make a mistake, they don’t want to lose money, and they don’t want to mess it all up. That fear, doubt, anxiety, and worry can prevent someone from even tipping their toes in and trying something.

If you are starting from a place of, “I can’t do this,” or “Something will go wrong,” it will become really difficult to wade through rea-life challenges that come up. Instead, if you can work through those limiting beliefs, you will develop strength, resiliency, confidence to tackle challenges head-on.

A common theme with successful real-estate investors is that they were able to shed their limiting beliefs earlier in their career. For example, someone who starts in a sales job might work hard to become an expert and develop a mindset of success within the relative “safety” of a job. Then, they have that confidence to step out and get into real estate investing or another entrepreneurial endeavor. So, wherever you are, start working on eliminating those limiting beliefs that are holding you back.

2.     Lack of a Strategic Plan

The truth is that a lot of people spend more time planning a holiday than they do planning their business. Now, obviously, planning a holiday is a good thing. But what if you could devote that time and energy into your business and real estate investments? What would it look like to get really clear on your strategy and direction?

The best way to develop a strategic plan is to start with the end in mind. Focus on things like asset class you want to buy, what markets interest you, and if you want to be a passive or active real estate investor. Then, you can reverse-engineer the steps you need to take to get to that destination.

To get clear on your direction, focus on the three modalities:

  • Short-term goals: Where do you want to be in the next three to six months, or even up to one year?
  • Long-term goals: Then, if you are successful in the short-term phase, where do you want to go next? This is considering the next 1-5 years of your business.
  • Vision: Consider what you want things to be like 5+ years from now. This is shaping the business for both your business and your life.

It’s okay to dream big when focusing on these modalities, especially in the vision section. The key is to then reverse engineer back to what you need to do today to make that happen and start taking slow, practical, and realistic steps to get to where you want to go.

3.     Lack of Systems for Support

Finding people to support you is important on a personal level, but it is also an integral part of achieving business success. Creating and maintaining systems of support will allow you to execute on your strategic plan. It’s important to start by defining roles and responsibilities. Consider, who is going to look for deals? Who underwrites deals? Who will raise capital? By defining those roles and responsibilities, you can create an efficient system to get things done.

Building a system of support is also about documenting what works and what doesn’t. Instead of trying a shotgun approach of trying something once and switching, slow down and take some time to collect data and use it as feedback for what worked. Then, make an informed decision about what you should do next.

4.     Poor Time Management

Most people can resonate with poor time management. In a world of distractions and things competing for our time and attention, time management is challenging. Consider the 168 Rule: we all have 168 hours in our week—it’s up to you to spend them wisely. Are you doing busy work, or are you focusing on high-impact, high-income activities?

A lot of people don’t understand the difference between busy work and work that moves the needle. So, take some time to evaluate how you are spending your 168 hours. When you start honing in on the most important activities, you actually free up time to pursue other things that you love, like spending time with family or traveling. But, if you are stuck in the nitty-gritty details and busywork, you will forever feel like there is not enough time.

Trevor describes distractions as “shiny object syndrome”—just focusing on the here and now, what’s currently trying to monopolize your attention. Instead of getting sucked in to that, remember that real estate is a relationship business. You need to be focusing on creating new relationships, increasing your knowledge, and growing your network.

5.     Lack of Execution, Measurement, and Accountability

While all related, Trevor broke this last one into three parts:

  • Lack or execution: You can get rid of limiting beliefs, create a system for success, and optimize your work flow. But, at the end of the day, you need to be taking action to actually get somewhere. So, avoid a lack of execution problem by taking intelligent and inspired action.
  • Lack of your ability to measure progress: How do you know you are on track? Measuring progress is so important to success. You need to know what you are measuring, how to measure it, and why that matters.
  • Lack of accountability: Accountability is what prevents us from taking the path of least resistance. We’re all humans, quick to succumb to Netflix, the fridge, or social media. But those are not things that will grow your real estate empire. Building in accountability helps you stay on track with the things that are most important to you, both in your business and personal life.

Being able to identify and remove these five potential roadblocks will help you move from someone who is interested in success to someone how is committed to success. The difference is that someone who is committed will do whatever it takes to achieve their goals.

Someone who is committed to success also knows their “why” and can identify why they are taking action to achieve certain goals. Knowing your “why” keeps you grounded and focused on overcoming these five roadblocks to success.

If you are interested in learning more about Trevor and his work, head over to his website at You can also personally connect with him on LinkedIn or check out his newly-launched private podcast, Rich Beyond Belief.

Michael Holman

Michael Holman

Michael has extensive financial and operational experience. He is a licensed Certified Public Accountant and has a Masters of Accountancy from Brigham Young University. Before working at Overland Group, Michael worked at Ernst & Young on some of the largest real estate and technology companies in Utah.
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