Jennifer’s entrepreneurial story. She didn't go to college. Here’s how she got into the real estate industry.

So I went to community college for a couple of years and frankly, I wasn't finding any real world application. I was just like, wait a second. This has nothing to do with making a living. What am I doing here?

I was working two jobs. I'm from Seattle and we have these things they're called espresso stands, and it's basically this little box where you stand in there and you serve coffee all day long. It's rainy all the time, people buy coffee all day long. It's kind of a thing in Seattle.

I would work from 5:00 AM to 1:00 PM, serving coffee, and then I'd go home, take a little bit of a nap and then either do my college courses. So I do like in person community college, and I worked my night job and my purpose was to gain as much real life experience and skillset and working so that I could do something with it.

But I just didn't know at the time what I wanted to do. I wanted to be an entrepreneur. I was studying international business and trade, I wanted to do something with business.

So I quit college because I realized, hey, I think I can just do this on my own. I can gain some real life experience. I can work for some small businesses, add value to them, become indispensable and then gain some income and kind of figure out just what I wanted to do along the way.

Her first experience with real estate.

I also set a goal that I wanted to own my first house by 21, and so I was saving all my money from my waitressing and saving all my money, my tips from my barista job. And I was able to buy my first property at age 21. It was the cheapest, ugliest property in the not so great town that I lived in, but it was all that I could afford.

And I just started tearing that place apart. It was built in 1901, which for Washington state is super old and I just fell in love with the process. But there were a couple of things that I realized throughout the way.

So one is people were making a killing flipping houses. Like you could buy a house, do a little bit of work to it, sell it and make like a hundred thousand dollars. And then the other thing I noticed was the real estate agent that I was working with had made $7,500 showing me one house. And I'm like, okay, I think I found my thing. I got to figure out this real estate thing. Yeah. So that was kind of the start. That's how I got into real estate.

Jennifer on whether real estate is a tough industry to get into.

2007, it wasn't tough, and then 2008 happened and it got really difficult. So yeah.

I think with anything in life and with business and being an entrepreneur, you get out what you put in.

And so for me, it was about learning the business, but also finding efficiencies and the most profitable part of the business.

I think some people get into real estate and see easy money, but depending on what area of real estate you're doing, it can be a lot of hard work.

The early business challenges that Jennifer faced.

I didn't know what I was doing. My grandfather is 89 years old and he has had many businesses and some were great successes, others were complete utter failures.

He told me when I was young and I was succeeding at a high level, and he would say, you know what, you're just too naive to know any different.

And so I was just moving forward. I think sometimes when you're young and when you're new, you don't know what you don't know, which is good and bad. It's a blessing and a curse.

The blessing is you don't know any better and so you don't have these limiting beliefs. I think that you don't have as many limiting beliefs cause you just don't know any better. Then you have to figure it out and sink or swim.

I'll kind of collapse time and get you into like the next level of the story.

2008 hit and I bought that first house, and then I decided to get a job in real estate. So I worked for a local builder and I realized a couple of things.

Finding opportunities in every situation.

With every job that I had prior to that, I always looked for the opportunity, and then I would take that opportunity into the next opportunity.

So for anyone that's maybe listening that is working and is looking to transition into an online business, they're finding the opportunity in what you're doing right now, and then use that opportunity into your online business.

And so that's a habit that I've used actually with everything in mind. And so anyways, I found a couple of opportunities within that role that I was working at the construction company.

One of those was I got my real estate license. So I could make that $7,500 when I showed a person a house. And then the next opportunity is I learned how to build houses.

When I officially quit my nine to five and started my own business, I started building houses.

The challenge was I had no money, but I had skills in an area of business that required a lot of capital.

So I had to get very creative and I talked to friends and family and said, hey, the first project required about $750,000 in order to do this project. And I talked to friends and family into trusting me to invest in this project. And it went flawlessly.

It was kind of odd because it was during the great recession, which was probably one of the most challenging times to be doing real estate.

However, with anything, if you can kind of hedge the downside, then it makes sense.

So for me, I ran the numbers backwards and forwards and I said, okay, if we can't sell this real estate, we can at least rent it and make double digit returns. If we can't sell it for what I think we can sell it for, we sell it for a little bit less and still make phenomenal returns.

For me, with business, I look at the upside and then also the potential downside almost to the point where I can convince myself that I can't lose.

And I know that that's probably that's a bold statement, but I think that really makes a difference. I think if you can get into opportunities that maybe don't require as much of your own capital, but you can tap into other people. At least that's how it works, within some of these real estate projects, then you can make it work. And so that's what I did.

Going from employed to self-employed to business owner.

The challenge with real estate activity is it's not typically scalable. For years, I was flipping houses or working with investors to buy properties and I was able to make a good amount of money doing it.

But the challenge was, I was still trading time for money. I've moved from two employees into self employment and had less freedom but more money, but that's not really what I was going for.

So I got to stage two. I am moving through Robert Kiyosaki's cashflow quadrant, but I need to somehow figure out how to spend time on the right side.

So I moved from employee to self-employed. Great. That's like the hardest first step for most of people, but getting from self employed to business owner - that is the next level. Really tough because what got you successful in self employment, typically is you and your activities and your material participation.

When you move from self-employment to business owner, it's about other people. You have to master working with other people and having a team and figuring out how to somehow duplicate your genius and then delivering it in a scalable way.

That was really, really challenging, especially with what I was doing. I can't build houses and not be there and not materially participate.

So I started to listen to my audience. Throughout this, one thing I wish I would've done is I wish I would've posted more on social media about what I was doing within my business. Documenting the journey.

I think as entrepreneurs, we like to wait until we feel like we've had some level of success and then we talk about it. But that journey is where like all the magic happens and there's so much to be learned from other people.

The difference between self employment and owning a business is if you can step away for at least four weeks, ideally eight weeks, not participate in the business at all and it runs and potentially grows without you.

My self-employment friends, they would say absolutely no way. I was on a call earlier today and I was challenging a self-employed friend of mine to take three days off. She was like, oh, I don't think I can.

So if three days or a week is a challenge, then you are self employed. You've created job security for yourself within your own business. I've stress tested 10 weeks gone, and it was a humbling moment to check in and realize that the business had grown.

That's I realized that's like a whole other level, but that's the difference - is if you can truly step away and the revenue can still come in and the business doesn't implode, I mean, stuff is still gonna break. You gotta fix stuff when you come back. But yeah, that's the difference.

So for a lot of my self employed friends, start making strides towards online businesses because we can be remote independent. We can work remote. We can be location independent, but still, if we have to show up on a day to day basis, we're self-employed, you don't have a business.

Building a team to support her business.

When I started building the team, this was in 2015 and it was our biggest year yet. I had nine people reporting to me, nine direct reports, and I had created this wonderful role called Manager. And I wasn't able to move the business forward.

I wasn't able to be the visionary. I wasn't working in my area of expertise, my genius.

I was frankly just like a manager and it was not good. It was not sustainable. I was burned out. We were in Hawaii for my daughter's first year, her first birthday. And I remember this moment when my husband said, are you gonna come and hang out with us on the beach? And I was just stuck in this beautiful condo on the beach, in Hawaii, working the whole time.

That was my epiphany moment when I'm like, wait a second, I'm doing this all wrong. I've got to break this all down. And literally I kid you not, I broke it all down. Every single ounce of the nine people, some of them quit because I was a bad manager, I shouldn't be in a manager role.

And then the other ones, they just weren't a good fit. So I completely broke the business down and then rebuilt it with an online business model, scalability, where I could live anywhere in the world and have the business operate and run and do great things.

So I ran some experiments. And first, oddly, I put real estate aside and I decided that I wanted to do drop shipping. I started an eCommerce drop shipping business so that I could learn how online businesses work.

I took a course by Anton and it's dropship lifestyle, and it's really funny because that business was a complete failure.

I knew nothing about Google PLF. When I heard that, I'm like, oh, this is a thing. I had no idea that you could like pay Google to have your ads. You don't know what you don't know. I knew nothing about running an eCommerce business, especially with drop shipping.

And so, I think I lost maybe $12,000 with that little venture, but that experience led me to realize, oh, okay, I see, I should just stay in my area of expertise in real estate, but take what I learned from this opportunity and apply that towards real estate.

On what Jennifer is doing now to recession-proof her business.

I think dig into your area of expertise. I am doubling down on the content that our audience needs in order to get results. So for us, obviously we're in the real estate business, but it doesn't really matter.

I think for any business person, at the end of the day, you need to get results because that's where the value comes in. So if you can help people get results in whatever it is you're offering, then you have a valuable business.

It might just be like... for right now, I'm seeing opportunities where you know, online learning is so much more popular now than it was in the past. It's actually easier for us in some ways to do business online, to do events online because that's really our only option.

Prior to COVID-19 happening and prior to March, most of our events were in person, and so we do weekend investor trips where people would fly in and we'd spend the weekend together and have these trips. Then we do a once a month in person meetup, and then we do like workshops and things, and that was all out the window.

That is not on the business plan anymore. So we took that opportunity and said, all right, so people really want our content, right? So they're asking for our content. How can we deliver it in an online space and an online way that's also scalable? So we launched our membership group, actually we launched that in May, so that's super new to us.

We're getting ready to host a virtual summit here in a couple of months and all of these things would not be on our business plan had COVID-19 not happened.

I do think it's very important to note that business owners need to maintain liquidity just in general. We don't know what's going to happen. Consumer behavior is kind of all across the board right now.

I have a friend of mine who did have an eCommerce business, was doing millions of dollars a year. February hit and he was out of business and frankly, he said it was a liquidity issue. He didn't have the liquid capital to sustain a few months of drop in revenue, and so he was out of business and now he's starting a new business.

I think that that's really important is to make sure that you're taking profits, setting some aside for a rainy day event or a global pandemic.

And then also looking to reinvest in the business, to grow it, and then finding opportunities with what's happening, paying attention. I kinda like to play this game of what will be the new normal?

And so I'm thinking, okay, VR space, that'll be interesting. Imagine if we watched sporting events from VR headsets. Obviously we're seeing companies now make masks. So I think that there's going to be endless opportunities that come from this. It's just a matter of, are you paying attention? Do you have the capital? And then frankly, do you have the courage to just go for it?

On whether Covid-19 has affected her membership sales and if people are signing up for it.

It's really interesting because I had the expectation that people would put a pause on investing in real estate, like who wants to buy properties in a global pandemic with a eviction ban.

In the US, we have an eviction ban, so if a tenant is in our property not paying rent, we cannot legally kick them out. That's a big limitation.

I have my real estate business and then I have my real estate investment, my personal real estate investment. I like having multiple income streams, they just all happen to be in real estate, which I don't know if it's a good idea or not.

On the importance of having courage to make decisions right now.

I made so much money and took advantage of so many opportunities in the last recession that I'm approaching this global pandemic and this new recession that's to come in the same way.

Whoever has the courage to take advantage of the opportunities. People still need a place to live. There's still people who have a lot of money in savings that if we see inflation get out of control, anyone that has money saved in the bank is going to suck. That's not a good thing for savings in the bank.

You have to pick a lane as far as where you're going to put your capital, either, invest it back into your business or invest it into other things. Our community understands that.

And it's really interesting because a lot of them miss out on the last recession, so they see this as an opportunity to get into this next recession that's to come, which sounds so bizarre.

Even looking back, think of how many businesses came out of the great recession of 2008. For online businesses, put your stake in the ground and really add value to people, and then you're going to grow your business exponentially throughout this.

How to identify business opportunities in your space.

First and foremost, I like to listen to our customers. We operate our business on what are people asking for, and then what would it look like? How could we deliver that to them?

Then we just create offerings and products and services based on what people are asking for, if it's scalable. My new thing is I don't want to go back into self employment contract, I want to stay on the investor and business owner.

So we just take feedback from our customers. And I learned this from building new construction is we find the opportunity when you're building something to fill a gap or fill a hole that doesn't exist. I would decide what to build based on what didn't exist that I knew would be desirable.

I think the same thing applies for online businesses. What are you seeing? Obviously, you guys are more sophisticated. I imagine you know Google keyword searches and things like that. You can pay attention to consumer behavior and then figure out, do you have expertise in that area? Can you create a product or a service based on what people are searching for if there's no one else doing that?

That's what gets me excited is how can we be the only one in town offering this thing? How can we get results? How can we add value? Are our customers asking for it?

I just feel like there's so many opportunities right now, especially in the online space. I look at the online space like digital real estate.

So I own physical real estate, but we also have this potential to create digital real estate for ourselves. Our digital real estate can be out there, but we can be wherever. So that's a beautiful thing. I think it's fantastic.

On the shift in her business and marketing activities since Covid-19.

The in-person events are out, so we were getting a lot of business from in-person events and can't do that anymore, which creates an additional opportunity because now we're forced to reach an audience that is a global audience. We get this opportunity to reach other people.

The other thing, it's interesting. We had done some online courses and we stopped doing that to launch this membership because we realized that so many things were happening so quickly, that if we were to do an online course, it might not be the same info two months from now.

The only other downside with online courses that I found was that you put so much time in the creation. Obviously you can presale them and things like that, but I just wanted to get right into our audience, give them real time info.

So that's been a big change is we had done well in the online courses, but with things changing so quickly, I just kind of felt like that was a little bit obsolete with what we were doing.

So I found the membershipguys.com, I joined that and then I took the pieces of it that I thought would be applicable to our business.

Her launch process for the Addicted To ROI membership.

We basically just sold to our existing email list and we have a very small email list. We haven't done a ton of marketing.

Most of our leads are warm leads that come via word of mouth, which is fantastic. I will take word of mouth, small list, over a list of a hundred thousand that is just dead beats.

So we sent an email on May 4th and we said, all right, guys, we're gonna open up with 50 spots. I think we gave it two weeks or whenever the 50 spots were billed.

We sent one email and we said, okay, you guys have been asking for more connectivity, more access to us and our team, we have this new membership, we're opening it up for the first 50 people or this date.

We sold out in 36 hours and we had people that were kind of angry with us because they didn't get a spot, so we ended up launching with 61 people.

So basically it was one email. We only got to do one social media post. That was pretty much it, I guess actually, we did one more email.

So two emails on the last day. It was like, oh, we only have eight spots left. And then that's when so many people kind of flooded us.

Creating the Addicted To ROI membership.

So we had forum software with envision community. We had put some of our content that we had pre recorded previously into the backend.

We ended up taking some of our free YouTube videos down and then we put it in. This is like phenomenal, great content, but we took that down and then put it into the backend of our website that they would get access to.

So we just had a forum, we had some videos in the backend, and then of course we had events scheduled out. We have live events every month within our membership.

Jennifer’s advice on content creation in her membership.

Now the majority of our content comes from our members in our community. It's a value exchange.

A lot of them that have had success within our company are willing to share case studies and are willing to share what they've learned.

I used to think that I had to be the one to create all the content. Again, another humbling moment. I realized people don't always want to hear from me. They want to hear from each other and learn from each other.

Jennifer who has been investing for 13 years isn't as cool as Pete who's been investing for 18 months but has done 12 deals.

We kind of see ourselves almost as like the host. Obviously we do participate in the events as well, but our members, they do case studies, they do masterclasses. They love sharing their successes as well.

Don't think you have to be almost like a content unicorn. I think it's like you feel like you're a show pony that has to always go out and put on the show. That's not true. You've got other people that will gladly put content out there for you, as long as it's adding value to the community, then it's fantastic.

On her big ‘Why’ as an entrepreneur.

I love that question because we always tell people to figure that out before they invest as well.

I have a couple, so first and foremost, I just like freedom and I don't like to feel I have to be stuck or that I have to do something.

I like that I can wake up whenever I want. I like that I can show up whenever I want. I like that my family and I can decide on a whim to buy a travel trailer and randomly decide to travel across the US. Freedom is very, very high on my priority list.

The next thing is I look at business as the greatest sport in the world, and the interesting thing though is that you're not necessarily competing against other people. You're competing against your own potential.

So for me, I will likely, never reach my own potential, but I'm going to show up every day and see what I've got. This is like I'm playing the most competitive, the best game in the world and I'm playing against myself. I don't know if that's a why or if that's just like a motivating factor.

I love taking risks. I love taking leaps. Just like that ecomm... I have other business examples that are complete failures.

You don't always have a winner, but it's really fun to kind of go through that experience and somewhat painful at the time, but then take the lessons and I guarantee you, whatever lessons you'll learn from those failures, you'll create a winner on the next one.

On what Jennifer does on a regular basis to try to reach and grow her potential.

So I kind of go through these phases. It used to be that I had a fairly rigid schedule. I'd wake up and I do journaling and meditation, and then I do yoga and it was always kind of like a miracle morning type thing.

But then I realized that when you get so used to, at least for me, when I was getting so used to a schedule, I wasn't sure if I was doing it cause I wanted to, or if I was doing it just because it was habitual and a schedule.

So I actually stopped living based on a schedule and following basically what's interesting to me.

As far as growth goes, I talked about the ability to take risks because I feel like growth happens the more that you're willing to put yourself out there.

As we had talked about, I've owned a primary residence for 13 years, we were getting ready to sell our primary residence and we have no plans to buy another one.

So for me, that's growth because I know that there's going to be some challenges there. I think that the more you're willing to put yourself in uncomfortable situations is where you grow.

I do that all the time, I do it to my poor five year old daughter, I do it to my husband. We purposely seek out ways that we can get uncomfortable knowing that we're going to grow through that experience. We do this in a lot of different ways. Sometimes just doing these random, we're going to leave and sell our house, or, hey, I'm going to invest in this thing or I'm going to try this business idea or I'm going to put myself out there.

Last year was a big year for growth. I'm an introvert. I love speaking, but I love speaking one-on-one. And last year I was invited to speak and it was a group of about 600 people.

I was thinking the night before, okay, how can I get out of this? Maybe I can call in sick. Can you call in sick when you're a speaker? I don't know. So I found that if you are willing to say yes to things that are incredibly uncomfortable, you almost break into a sweat thinking about doing that, that's how you grow.