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Find Your Path: How to Succeed Through Trial and Error in Real Estate Investments

Like many things in life, getting started in real estate investing can be a wild ride. There are sure to be some twists and turns throughout the process, as you pivot and change courses to figure out a path that really works for you. The guest on episode 20 of The Executive Real Estate Investing Show, Josh Ferrari, shows us exactly that.

Josh is a multifamily syndicator who has raised over $7 million in private equity and has over 230 units in his portfolio. But he didn’t get there overnight. Josh’s first real estate venture lost him $5,000. The second lost him even more. It took time, mistakes, and a relentless commitment to learning and growth to get to where he is today.

The executive tip for this episode is to focus on the most important thing. Throw everything else out the window if you need to and really focus your attention on what is most important to you, both personally and professionally. For Josh, it’s creating a lifestyle that he wants, with flexibility, purpose, and time. This motivates him to keep working on his real estate goals and “vivid vision,” which we’ll discuss further below.

Let’s take a look at some of the takeaways from our conversation with Josh and how you can apply them to your own goals, whether in real estate investments or elsewhere.

Real Estate Investing is a Windy Road

Josh’s story is one of twists and turns. Part of his impressive bio is that he was able to go from zero to 239 units in six months. This is a major feat, especially for someone still working a full-time job—yes, Josh still works a 9-5 as an aircraft technician!

Josh was quick to point out that, while technically true, that one-liner does not capture the full story. There were three years of hard work and challenges that laid the groundwork for his six-month, 0-239 success story. Josh’s career has taken so many turns. He started out thinking he would end up in the navy, but pivoted towards becoming a pilot. After realizing the hours that would take away from a future family, he became an aircraft technician. Despite still working as a technician, Josh really was interested in real estate investing and saw the potential benefits of it to build a passive income lifestyle.

Josh’s first real estate venture was in wholesale. He ended up losing $5,000 doing so. Next, him and his wife tried house hacking—they lost even more money. Eventually, he learned about multifamily syndication and was able to really build something from it.

The point of sharing Josh’s story is that twists and turns are to be expected. There are so many people that start on the expected path of undergraduate degree > masters degree > corporate job, only to realize that it’s not for them.

So, if you are starting out in your real estate investment journey, remember that it’s okay to make changes, to pivot, and to try new things. Each step is a learning experience to help you learn, grow, and find success.

Further to the twists and turns of a career, it’s important to remember that all good things take time. There is no such thing as overnight success. Josh discussed the three-year time period before his business really took off and described it as “chaos.” There were challenges and mistakes, but through it all, he learned a lot. Josh shares that “we found out what we didn’t want and propelled us towards what we did.”

Find Your Motivation for Real Estate Investing

It’s easy to read that last section and wonder why Josh continued in real estate. What was the motivation? After experiencing so many challenges, and even failures, what led him to press on? Josh shared a number of motivators, including:

  • A sense of wanting to prove himself. Josh describes himself as persistent and wanting to learn and follow through on things. He shared that proving both to himself and his wife that real estate investments could work was a motivating factor and allowed him to stay persistent through the challenges and set backs. Each person needs to find their own motivation, whether that be their own internal drive, or to support their loved ones and build a better life.
  • Other people’s success stories. Josh shared just how important it was to hear other people’s stories of success. And not the stories of people who come from money and inherit a company or something like that. Instead, these are stories of people who started with nothing and were able to learn, grow, and build something successful. Stories of real people making it work. Seeking out success stories can be very motivating because it helps you remember—if they can do it, so can you!
  • Building a network and staying connected. The last motivator for Josh was his network of friends, colleagues, and others who were working in real estate. Instead of isolating himself, Josh leaned into the networks of other people in real estate investing who were trying to do the same thing. Surround yourself by like-minded people who can help you along the way.

All entrepreneurs view failure a little differently than the average person. Instead of it being a signal to give up, it’s just a prompt to pivot, adapt, and change directions. Finding your own personal motivations, like Josh did, will help build resilience and perseverance during the inevitable challenges.

Expand Strategically with Your Real Estate “Vivid Vision”

There comes a time for most entrepreneurs and business owners that they need to start thinking about expansion and growth. It’s an exciting time, as it means you are finding success, but comes with its own challenges, too.

Josh discusses the quick growth of his company. In just over half a year, they started closing on hundreds of deals and raising huge amounts of equity from investors. It took off fast, and Josh and his business partners had to address new challenges as they come up. At the beginning, it was all about acquisition of new units. But as they acquired more and more, it became about managing all the units.

Strategic expansion is important. You need to carefully analyze where you’re at and what kind of help you need. One way to expand and grow strategically is to have a “vivid vision.” This is a concept that was introduced to Josh via a book of the same title by Cameron Herold. A vivid vision has the following aspects that can help guide your company or business venture through growth and expansion:

  • A vivid vision is very, very specific. Josh tried to write his vivid vision in a quick, bullet-point format, but found it did not give him enough traction to move the needle. So, he spent more time writing a detailed, in-depth vision for his company and life. In it, he has clear goals about what he wants things to look like in 2023 and how to get there. It is detailed and specific so that there is no guesswork involved.
  • A vivid vision is collaborative and meant to be shared: Josh shared the vivid vision with his partners, who loved it and were bought-in to the vision. Since they are all on the same page, they can move together to ensure that they are making the right decisions to meet the goals.
  • A vivid vision can be reverse-engineered to help with decision-making: After getting the whole vision down on paper, you can begin to work backwards and plan your steps and decisions—what am I going to do today—to get there.

Real Estate Investment Talk: Why Multifamily Syndication?

A lot of this advice can be applied to different business ventures. But this is the Executive REI Show, so we want to talk a bit more about real estate. We asked Josh why he chose multifamily syndication, and he had some great insights to share.

Ultimately, he found this path through trial-and-error. And while the other types of real estate he tried—wholesale and house-hacking—didn’t work for him, they may for others. Ultimately, you need to try a few things to figure out what works and what doesn’t.

Josh was drawn to multi-family investments because he liked the concept of different revenue streams under one roof. At first, he thought that he would have to make all the investments himself, which is a massive financial stretch for most people. So, after discovering syndication and learning that he could raise capital, it was the obvious path to go. Josh sees multifamily housing as a way to achieve a passive-income lifestyle, where he can work as much or as little as he wants while creating revenue to keep working towards his “vivid vision” life and career goals.


This conversation with Josh Ferrari had so much value for entrepreneurs, real estate investors, or anyone trying to take that first step off of the prescribed career path we often feel stuck on. Josh’s last piece of advice was from a life lesson he learned from a mentor: keep learning. You might think you know a lot, but there is always more to learn. So, be open-minded, learn what you can, and just jump in and start going.

If you want to know more about Josh or connect with him, you can do so at From there, follow him on social media—Facebook, Instagram, LinkedIn, and YouTube—and check out his podcast, “Creative Capital,” available on all podcasting platforms.

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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