How This Real Estate Entrepreneur Achieves Lifestyle Freedom

I’ve been given the opportunity to speak with Ali Boone. For those of you who don’t know who Ali is, she’s become a major player in the Real Estate game by starting her own company, Hipster Investments, writing OVER 180 articles for Bigger Pockets, and being featured on over 30 podcasts. I’m excited to share with you the interview I had with her! You’ll learn everything from how to run a successful business to how to achieve the perfect work-life balance while traveling the world.

Q: Ali, I’m just dying to dive into how you’ve structured your business. But first, can you tell us a bit about yourself and how you got to where you are today?

A: For sure! So my background is actually in Aerospace Engineering. When I was still in college, I got my pilot’s license and helped pay my way through grad school by flight instructing. So I was very much the left-brained engineer math geek type—flying airplanes and doing engineering. I’ll never forget walking into my new cubicle, though, at my first engineering job. The minute I set foot in it, it felt like my soul had sunk to my toes. While I was used to having the wide open blue sky as my “office”, now I was staring at nothing but gray cubicle walls after having walked down about a mile-long underground tunnel. Then I looked down at what I was wearing, which was a hideous business casual outfit, and I knew something wasn’t going to work. Despite being the engineering geek-type, I had also always been very much a rugged individualist and was not a fan of structure or being told what to do…in any form.

I knew I had to find a way out of that cubicle. I spent the next 5 years studying and exploring everything I could find in order to find a way out. Eventually, some opportunities presented themselves to me, and I followed them—having no idea at the time they would be what got me out of corporate—and next thing I knew, I was starting my own company. I hung on to my corporate job as long as I could while trying to build my business, and then I took the plunge! Now I’ve been on my own and doing the entrepreneur thing for almost six years.

Q: Wow. I can’t wait to hear more details on all of this. First, tell us what your life looks like now and how is that compared to how it was when you had your corporate engineering job.

A: Oh geez, it’s like a 180 difference in lifestyles. Back when I was an engineer, I had to do the usual 9-to-5 bit—report to work on a Monday morning, leave later in the day, have minimal time to get anything else done, use the weekends to recoup, and always ask permission to take a vacation…or be sick! It was especially limiting later in my engineering career when I started working as a Flight Test Engineer and had to live in a Top Secret location Monday-Friday with minimal access to the outside world. Needless to say, what time in my life I wasn’t spending working was really controlled by when I needed to be back to work. Even where I lived was determined by work—I had to live within commuting range of my job.

The minute I quit that job, though, I immediately moved to Venice Beach, where I had wanted to live for years but couldn’t because the commute would have been impossible, and started living in my pajamas and making my own hours. I travel whenever I want to, I schedule any events I want to, and I get to pick and choose every single thing I’m involved with in life. I love having the freedom to work late at night and sleep in in the morning rather than having to wake up long before my body wants to wake up. I take random breaks during the day to watch my soap opera or play with the dog. Some days, I don’t even work. My schedule is 100% flexible. I’ve been able to go back to flight instructing because I love doing it. I’ve gotten highly involved in service too, specifically in California prisons working with inmates, and having the opportunity to be of service and help others is a whole new level I hadn’t even anticipated. Just generally, I feel like my soul is 100% intact. And I’m grateful almost every single Sunday night that I don’t have to wake up in the morning and go into a job that I don’t resonate with.

Q: This is so interesting to hear how the entire structure of your life is different now since you have your own business versus when you had a 9-to-5 job. But with having your own business, isn’t that a ton of work? How are you able to have so much flexibility and so much free time? Isn’t that the opposite of how it normally works when someone runs their own company?

A: Well, for most, yes. But I was fortunate that during the time I was doing all of that exploring in trying to figure out how to get out of corporate that I was able to learn a lot about the difference between working IN your business and working ON your business. The two places I really learned about this concept were from Robert Kiyosaki, the author of Rich Dad Poor Dad and the founder of the Rich Dad series books, and in The E-Myth Revisited by Michael Gerber. Reading the teachings of these two authors really helped me understand the difference between owning an empire where everyone else does the work for you and doing all of the work yourself to make money and keep your business afloat.

After those seeds of curiosity had been planted, I stumbled across a guy—who is still to this day my primary mentor—who owned a location-independent business and was making his own hours and developing his own lifestyle design by way of that company. I sat there and stared at him in his flip-flops and khaki shorts, and no briefcase in sight, and eventually just started asking him how all of this was possible. How had he had the time to travel internationally? How was he able to make his own hours? And why didn’t he have a briefcase at a business meeting? This was the first time I was introduced to the idea of “location-independent” businesses.

They are businesses solely operated online, so literally all you need to work is an internet connection. You can do that from anywhere. I certainly wasn’t going to copy his exact business, but I was absolutely going to pick his brain for advice on this whole “lifestyle design” concept, which very often starts with creating location-independent businesses. And then, once you have the location-independent business, it’s a matter of structuring it in a way that allows you the freedom to make your own hours. That’s where the freedom begins. I was of course then turned on to Tim Ferriss’ The 4-Hour Work Week and really read up on lifestyle design and what is possible with it.

So as I started my company I kept all of these ideas in mind, knowing this was exactly what I wanted. I wanted ultimate freedom to work when I wanted or travel when I wanted, and I even wanted the ability to go back to flight instructing without being reliant on the pay. At a minimum, I wanted to be able to say yes to a friend asking me to lunch on a random day during the week!

Going back to the technical side of this, freedom comes from having passive income. Passive income is income you receive with minimal to no effort. Yes, some effort is required on the front-end in order to jump-start the income, but after that, you basically continue to make money in your sleep. There are some primary ways you can get passive income, but in terms of running a business and being able to be as passive as possible, you have to focus on 1) hiring employees and 2) creating systems and processes. With those two things, your physical (and sometimes mental) presence is no longer required in order for your business to make money. Sure, you have to oversee things and keep your vision alive and ensure everything continues to run as expected, but you can also very easily dip out of range on vacation for a week or two with minimal impact to your sales! That’s where I’m at now—I have people working for me that can handle things for me if I want to disappear for a bit. We all work whatever hours we want to, from wherever we want to, and if any of us are going on vacation, the others can hold up whatever tasks are needed. I really can’t say enough about the importance of outsourcing/hiring employees. It’s imperative if you want freedom within your business, but it also can elevate the success of your business as a whole when you have several people all working to their strengths.

Q: Okay, this is getting good. I want to dive more into this idea of passive income in a business and how this pertains to the difference of working IN your business versus working ON your business, like you mentioned. Can you give us a snapshot of your involvement with your company so we can get a clearer picture on how all of this might work?

A: Absolutely. Before I do though, let me give a perspective of this based on the ideas in The E-Myth. If you are phenomenal at making cookies and you currently make cookies for a particular bakery, you are working as an employee making those cookies. Let’s say you decide to open a cookie shop so you can have your own business making cookies, rather than work for someone else. Now you open up your own cookie shop, and alas, you are still making cookies! In fact, you might be making more cookies than you were before. And in addition to making extra cookies, now you have to run the business side of things as well. But, you started your own business so you’re good, right? Ummm… well I guess that’s up for interpretation but in my mind, now you’re working longer hours in the day and you’ve also added a significant number of crucial tasks to your job description that you may not even like doing. To me, that may not necessarily be a win. But let’s say you open a cookie shop and you hire three of the best cookie-makers in town who make the cookies for your shop. Now, your time is freed up while they make the cookies. Now you only need to focus on the business tasks, and even a lot of those you might be able to outsource. Eventually, you own a successful cookie shop that still makes money even if you aren’t in the shop! See the difference in the two setups?

With that concept in mind… With my company, I started out doing everything on my own. I think you have to start this way because how else would you eventually know a) what jobs you need to hire out (and can be hired out) and b) what systems and/or processes to create for employees? But as soon as practical, I slowly started outsourcing the everyday tasks I was doing. For me, the first thing I needed help on was email control—because all of my clients and prospective clients reach out via email and I was so swamped answering emails 24/7 that I couldn’t get anything else done—and help with building the website. I had gotten the website far enough to be functional, but after that it was just out of my wheelhouse to make it any fancier. And I very quickly learned that what I could sit and struggle with for ten hours could take a web pro just a couple minutes to fix. I eventually brought in a few different marketing positions, a user interface expert at one point, a graphic artist for a couple projects, and some other random positions I’ve needed for various projects over the years.

Right now, I have three main tasks that I personally do in my company that I don’t hire out:

  1. Continue to expand new marketing and content efforts, and the general vision of the company
  2. Be available to help  my employees with any non-standard situations, or new situations they aren’t familiar with, that might arise
  3. Write the bi-weekly blog articles that draw the majority of our clients to us and participate in daily real estate forums as a way to get more exposure. These are the two primary job tasks I can’t outsource because they are based on me talking, and so far I haven’t found a way to outsource me specifically. None of the rest of my company’s tasks specifically requires my exact language or personality.

What’s key with these tasks is that I can disappear for a week and not do any of them and the company will go on business-as-usual. I wouldn’t be able to not do any of these things for the long-term, but I could even pull off being gone a month if I wanted to be and not do any of these and still be okay. And with those tasks being fairly straight-forward (other than the abstractness of coming up with a creative vision for where to lead the company and how to get us there), I can do those tasks at any time of the day. I very often wake up slowly, decide to watch my soap opera before I work, get distracted on the phone, eat some dinner, and then eventually get around to doing my tasks. I have no deadlines.

All of that is where the freedom lies. I’m definitely not financially-free, as I need my company to bring in income in order for me to sustain my lifestyle, but I truly have the ultimate flexibility in how and when I work in order to keep that income flowing. For me, that’s the next best thing to actual financial freedom, but really what financial freedom offers is the ability to create your dream life because you aren’t tied to the schedule and constraints of a job. I’m doing that now, even with having a “job”.

Q: I think you are shedding a profound light on entrepreneurship and really breaking down this idea that you have to work 17 hours a day for 10 years in order to be successful.

A: Yes, well don’t get me wrong. I busted my ass to build what I have built today. I definitely had 17-hour work days in the beginning. But what was awesome about those long days was that I LOVED what I was doing. It didn’t feel like 17 hours at all. I would be so excited to work I often forgot to shower! I went to bed anxious to wake up the next day to get back to what I was working on. And before that, I spent hundreds of hours over the course of a few years diving in and trying (and failing at) different things before I got to the place where my company started forming.

You don’t just wake up and all of this is just created by any means. But if you understand your intentions and what it is you really want as you start into it, you can more quickly and efficiently make that happen. I was only two years into my business when I decided it would be a bright idea to go back to school and fortunately I had already set my company structure up so that I had a substantial amount of free time because I ended up needing that hardcore for school! Despite my focus being on school for a couple of years following that, my company continued to grow exponentially.

Q: You went back to school? After having been in graduate school for Aerospace Engineering? What in the world did you get another degree in?

A: [laughs] Wellll… I got a Master’s degree in Spiritual Psychology.

Q: Holy crap. Wait, so you have a Master’s degree in Aerospace Engineering AND a Master’s degree in Spiritual Psychology?

A: I do. I admit that the only reason I started into the Spiritual Psychology degree was that I thought it’d be hilarious to tell people I had both of those degrees. It turned out though that I loved the work and it changed my life, and now I use it all the time just in everyday life and various projects I’m working on.

Q: Well I barely know which way to go with my questions now. There are so many possible directions. Man. Okay, well I foresee more interviews with you in the future so we can dive into more of this, for sure. So for now, let’s wrap up with some takeaways you would offer people on the entrepreneurship side of things. Can you share just some general tips or thoughts that might help people who are either thinking of starting a business or maybe have started one but are still in the structuring phase of things?

A: Of course. I know I’m going to leave some out, though. I’ll probably think of more at like 3am in the middle of the night and be mad I forgot to include them! [laughs]

Okay, just a couple of tidbits. Well, my favorite quote is “Don’t take advice from someone you wouldn’t trade shoes with.” That quote has been so important for me over the years. There is so much chatter these days and so many naysayers; it can really get debilitating listening to everyone telling you what you “should” do. What I’ve really focused on is finding people who are actively living the type of life I want to live or actively doing what it is I want to be doing, and I seek their advice. I don’t just trash any advice I get from other people, but I consider the source and really weigh if what they are saying is a fit for me or not.

Take the time to start finding out what comes naturally for you. Following the things that come most natural for you and most organically are truly, I believe, the things that will offer you the most ability for success. Do the work, set your intentions, pursue everything you can, but then really pay attention and follow what is laid in front of you. I know I couldn’t have created or dreamed up what my company has become if you had paid me. Instead, I just followed the opportunities that came to me (after doing all the work) and that allowed the company to create itself.

Be really clear on what you want to achieve. For me, my goal is no longer to become a gajillionaire. If I pursued that route, I believe I would have to sacrifice time and sanity (two things I believe to be actual currencies in addition to money) and that is not what I want. I’ve never wanted to create another job for myself. I’ve wanted to create freedom for myself. When you know your true goals (and don’t be shy about them), you can better tailor everything you do in order to support those and choose the opportunities that fit those.

Q: You know, I just get this sense of magic in the words that you are sharing. It feels like you are offering people advice on how to achieve a level of magic for themselves!

A: I really have never thought of that word in relation to all of this, but since you say it… it really does feel like magic to me. I am grateful all the time for even the small things—waking up whenever I want to, being able to stop working to make a nice lunch, and of course the bigger things like traveling whenever I want. It does all feel like magic to me. I love that you used that word—now I can think of it all as magic more often! It’s such a powerful word, I feel like it could help me manifest even more of it.

Q: Well, Ali, this had been amazing. I would really love to do more interviews with you as I feel like you have a whole arsenal of helpful information and advice for everyone. In the meantime, where can people find you and get in touch with you?

A: Everyone is always welcome to email me directly- If even just to say hi! I love meeting people. My company’s website is if you want to check that out or if you have been wondering about real estate investing and how you might be able to do it. My business consulting site is (it’s a fairly anti-climactic site, sorry). And you can find me on Instagram and Twitter at @aliboonedotcom. Ironically, I don’t have a Facebook page, so don’t try to find me there

Q: No Facebook page??

A: [laughs] I’ve never had one before.

Q: Well, that is certainly going to be the first thing we address in a future interview! Ali, thank you so much for taking time to talk with me. It’s been a great pleasure and I look forward to hearing more about what you are getting into!

A: Absolutely, and thanks so much for having me!

I highly recommend checking out Ali’s company and site! Don’t hesitate to reach out to her; she will definitely answer your questions. If you follow her advice given above, it’s only a matter of time before you, too, become successful!

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