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Jump in to Real Estate Investing: Advice from Experts on How to Succeed

It’s hard to believe that 2021 is coming to a close in just a few days. We’ve had an amazing year here on The Executive REI Show talking about building generational wealth through real estate investing. We’ve had a huge range of industry experts as guests on the show, bringing their years of experience and wisdom to help show us the way.

Guests have ranged from coaches to sponsors to influencers to business owners—each with their unique perspective to share. Just some of the amazing guests we’ve had include doctor and investor Vikram Raya, multifamily syndicator Josh Ferrari, serial networker Esther Reizes-Lowenbein, and coach Jerome Myers. You can catch up with all the podcast episodes from this past year over on our website at

At the end of every podcast episode, we like to ask our guests two questions: “What’s the best business advice you’ve ever been given?” and “What is your advice for new investors?” Their responses are gold. Seriously, if you put this advice into action, you are saving years of trial and error to figure it all out yourself.

A lot of the advice is centered around three main themes: don’t go at this alone (find a coach!), get yourself in the game ASAP, and keep learning as you grow. Let’s look at each one a bit further.

Get Some Help and Learn from Others

So many of our expert guests shared the advice to work with a coach or a mentor. There’s the old adage, “you don’t know what you don’t know,” and working with someone who has already been there can be invaluable to learning the knowledge you need to find success.

Working with a coach or mentor is also tied to the importance of relationships in real estate investing. The whole industry is built on relationships and forming key partnerships. This should be done through consistently focusing on the basics of doing what you say you will, communicating well, and working together for success.

Whether you are working specifically with a coach or just building strong working relationships for real estate, here are some tips from our guests to keep in mind:

  • Find a mentor with the same values and goals as you.
  • Make sure you are also adding value for your mentor so that it is mutually beneficial.
  • Take time to build partnerships and develop a foundation of trust.
  • Do your due diligence on people you will be working with to ensure they are honest and a good partner to work with.
  • Be transparent by telling the truth and providing all relevant information, even when it may be bad news.
  • Educate yourself and learn from people who have gotten to where you want to go; their advice can shave off years of learning through trial and error.

Real estate is about relationships. It can be a kind of “old-school” industry that still relies on handshakes, phone calls, and coffee meetings to build relationships and trust. This is so important because you are dealing with large amounts of money and you absolutely want to trust the people you are doing business with.

So don’t go at it alone, but find other people who will help you, show you the ropes, and mentor you towards the right opportunities in real estate.

Don’t Be Afraid and Jump Right In

A second major theme that emerged from all the advice of our expert guests can be summed up in Nike’s famous slogan, “Just do it.” Some of our guests literally said just that! You’ve got to get off the sidelines and get in the game.

Many people are afraid to jump into real estate investing because it is the fear of the unknown. But through some learning and working with others, you can establish a baseline knowledge that will empower you to jump right in.

There are a few questions that you can ask yourself to help with motivation to jump in. Consider asking:

  • What is the worst-case scenario if I don’t do this? This could look like getting stuck in a dead-end job, living paycheck to paycheck, or not being able to pay for your retirement. If this is acceptable to you, maybe real estate is not for you… but if you’re reading this, you’re ready to change your life!
  • What is the best, worst, and most-likely case scenario? Think through each one and ask if you are willing and able to live with it. If so, jump right in and get involved.

Once you’ve made the decision to jump-in, it’s likely you’ll still have nerves. Or, you might not know exactly where to start. If this is the case, consider these tips:

  • Be persistent through challenges as that will lead to growth and knowledge.
  • Try different options. You may fail at your first multi-house family unit, but succeed in self-storage. The world of real estate is broad and there is so much room to try new things and see what works for you.
  • Do your due diligence and learn as much as you can so you are equipped with knowledge.
  • Use the power of the internet to grow your network! LinkedIn, in particular, is a powerful tool to surround yourself with people who you want to connect with or emulate.

Fear and excuses often hold us back from doing the things we know we are meant to do. We understand that real estate feels big and scary, but it’s actually a very well-established path to financial growth and wealth. Remember that others have gone before you and there are so many resources (like The Executive REI Show!) to help you learn and grow. So, educate yourself, learn, and then jump in.

Keeping Learning and Growing

We’ve already mentioned that part of real estate is about jumping in and learning from your mistakes. And the experts agree: you have to be patient and willing to learn and grow, expecting that opportunities and success will come to you.

Often, we are sold a lie in society that success happens overnight. If you get into real estate, you need to make a lot on your first deal or you’ve failed. Sometimes we expect so much from ourselves, and it’s really just unrealistic. One of our guests put it this way: you don’t need to catch Moby Dick on your first fishing expedition! It’s okay to start small and bring in bigger and bigger “catches” over time.

Here is some other advice from our guests:

  • Appreciate your failures and allow them to help you grow. There is always something to learn from a failure, even if it is just about your own resilience and ability to stick something through.
  • Know your “why.” What is driving you to get involved in real estate? Is it financial? Or lifestyle related? When you know your “why,” it is easier to stay motivated during the challenges and failures to keep going after your own goal.
  • Dream big! Your future is as bright as your faith. Dream big and believe that you can do this. Then, you’ll be more willing to take risks, work hard, and go for it.
  • Keep your options open. Remember that there are a million ways to get to the same destination. Maybe not a million, but there are certainly a lot of avenues in real estate investing! So, keep your plans open and adjust as needed—you will get to where you want to go.

Success doesn’t happen overnight, or at least for most of us it doesn’t! Instead, focus on learning from your mistakes, remembering your “why,” and following your dreams. Real estate investing takes patience, determination, and a willingness to learn as you go.


There you have it—the roundup of advice from some of our amazing guests on The Executive REI Show over the last year. The expert guests on our show provided some solid, actionable advice for those who want to get started in real estate investing. Key takeaways include: don’t try and do it yourself, but work with a mentor; jump in and don’t be afraid to fail; and always keep learning, growing, and working towards your goals.

2021 may be drawing to a close, but that doesn’t mean we are done creating content and helping you get started in real estate investing. 2022 is sure to bring more sage advice and wisdom, encouraging and motivating you to build generational wealth through real estate investing. Go back and listen to some of these amazing podcasts from 2021 and stay up to date with us at

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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