Episode #9:

Work While Doing What You Love

Do you dream of going out on your own and working from wherever and whenever you want? If so, what’s your why? So you can enjoy a more flexible lifestyle? Travel whenever you please or pursue side projects? Or maybe it’s to spend more time with family and friends. I’ve got two special guests to talk about the freedom they’ve experienced working for themselves and pursuing their dreams.


Show Notes


Robert and Alyssa SimmonsRobert and Alyssa Simmons are the founders of Hatmen Marketing, an SEO and digital marketing agency that specializes in helping small businesses with their website and SEO. Robert and Alyssa travel the country while continuing to run their business and have had many adventures doing so. They work to inspire others to find the freedom to work in your own way on your own terms while still enjoying life to its fullest. Alyssa is also the owner of a patent for a one-of-a-kind rain boot that is specially designed for their reversible, removable wraps. After having this idea, Alyssa created her company, Aly’s Boots, and has now had her first run of boots and wraps manufactured.


Colleen Gratzer: Welcome to the podcast, Robert and Alyssa. So, we’ve known each other for about two years now. You guys have done so much and at such a young age. I find your story to be so inspirational to others—especially those who want to go out on their own and do what they love and work from anywhere. So how long has it been since you both left your jobs?

Robert Simmons: It’s been almost two years now.

Colleen: And how did you decide that that was the right time to quit your job and go out on your own?

Robert: Well, we were … It’s kind of a funny story. We were talking about it, we’d been putting processes in place in our business that we knew would be what we needed to do to go full-time. We hadn’t yet really made the decision of whether or not we wanted to go full-time. Some changes in the workplace where I was at led us to the decision that it is time for us to move on. Instead of me looking for another job, we just decided that we would go full-time with our own business instead.

Colleen: And how about you, Alyssa? What kind of point were you at with your job?

Alyssa Simmons: My job was extremely stressful, and not what I went to school for anyway. So I quit my job when we got married. I stayed at home and did some writing, I did some substitute teaching at various schools, because I enjoy teaching. And then, about the time Robert quit his job, my grandma came to live with us so that was my other full-time job while also trying to get our business up and running.

Colleen: It took me several years to get the confidence in order to leave my job and go on my own full time. Did you guys have any fears or hesitations before jumping out and going full-time on your own, to work for yourselves?

Robert: Yeah, absolutely. It was probably the single most terrifying thing we’ve done to date.

Colleen: What was the most terrifying part about it?

Robert: The uncertainty. Not having … you know, I was coming from a salaried job and I knew exactly what my paycheck was going to be and when it was going to hit the bank and it was coming one way or another. But once I quit the job it was kind of like, oh, um, I guess I need to find something … some income. And of course there was … we had some recurring revenue to kind of hedge against that. But when we first started out it definitely was not fully supporting us at that point.

Colleen: What kinds of things did you do to prepare before leaving your jobs?

Robert: Well, one of the first things we did was we started from the very beginning trying to build up our recurring revenue. That was and has been our focus ever since we started and that is what has kept us in business this far. It’s definitely not easy to build recurring revenue sometimes, but it is well worth the effort, because that, as a business owner, as a freelancer individual, agency owner … whatever you want to call yourself, that is what gives you that stability and that peace that you have. When you have a job working for someone else you know the next paycheck is coming and you don’t have to worry about it. When you have that recurring revenue, that’s when you get that same feeling as an individual, agency owner or business owner.

So that was the first thing we did, and then the second that we did was we focused on getting all of our processes in place, and our systems in place, trying to make sure that we had everything as well planned and documented and repeatable as we could, so that we didn’t have to make everything up as we went along. Even though we do make a lot of things up as we go along.

Colleen: And did you have any clients already on board with you before you left your full-time job?

Robert: I had a few clients. We had a couple website jobs that had come in, and some projects that we were working on. As far as recurring clients, I believe when I quit my job in September of ’16, I believe we were at $400 a month in recurring revenue, if I remember correctly. So, I mean not quite enough to live comfortably in the United States.

Colleen: So what was the main motivating force behind leaving your job? Because like you said, you were getting a steady paycheck, you knew where your money was coming from. What was the big force that really drove you to go work for yourself and take that risk?

Robert: Well, I’m a rebel. So I guess that’s part of it. I don’t enjoy working for other people. Not necessarily because I hate authority or anything like that. I just look at everything that they’re doing and go, “Man, I could do that so much better. I could do this so much more efficiently. I could make so much more money doing this.” And knowing that I could do it better, and I could do it at least as good as they are, but I could make three times as much money on my own, it was kind of always in the back of my mind as I had a job.

Then secondly, I always kind of had that entrepreneurial bug. My grandfather started a restaurant when I was 17 and I helped him do it. In recent years my mom has bought him out and now she is running that restaurant. And several other people in my family own businesses and have their own thing going on. So it’s kind of in my blood a little bit to be an entrepreneur to some extent. But that was one of the biggest motivating factors. I wanted to have my own piece of business that I was responsible for, and it all came down on us.

But the second thing was freedom. That was … probably the biggest factor is freedom. We’ve always been big fans of traveling and doing whatever we want on our schedule. And we’re not exactly your typical late 20s couple.

Colleen: No, you’re not.

Robert: We knew that the life that we wanted would never be achievable by working for someone else. And if it was at all possible to achieve that working for someone else, it was going to take 20 or 30 years of working for someone else to get to that point. I am personally of the opinion that you should live your life now and not defer it until later because you never know how long you’re going to actually live.

Alyssa: I think the other thing too is, we’re also really big on family. Spending time together, being there for family, no matter what. And with his family being in North Carolina and having such young siblings, we were missing out on things because we couldn’t travel. We couldn’t go see them. Missing those moments, especially when you have siblings so young, you don’t get those back. They grow up so quickly. So we really wanted to be able to come visit, and they love us just showing up now whenever we can and visiting. So yeah, I think that was another part of it.

Robert: And there is no way I would have had the courage to even approach Alyssa with the idea of, “Hey, I’m going to no longer have a job. Why don’t I just not get another one?” if a few things hadn’t happened first. And the biggest thing that happened that made that possible was, I found this course … and this is actually how we met, Colleen. I found this course about three years ago, about a year before I quit my job. And I was just getting started freelancing. I’d been freelancing off and on [website design and development], but I had just started picking up and getting a few more clients and referrals, things like that. And this course popped up in my Facebook ads, and I was like oh this looks interesting, but it’s a lot of money. And it was WP Elevation, and their Facebook ad they hit me with gave me this template for a proposal for a website. And I was like okay, this is cool.

So I watched the webinar that went with it, and I got the template. And it just so happened that I had a lead that had come in at that point for a restaurant in downtown Chicago. So I used what I learned on the webinar in the proposal template to send a proposal to the restaurant for well, almost—or just over, I guess—three times what my typical website rate had been up to that point.

Colleen: Wow.

Robert: And they accepted it.

Colleen: Wow.

Robert: So at that point, I kind of went to Alyssa and said, “Hey, so this guy sent me a Facebook ad and I watched the webinar and this is what happened, and they signed the proposal, which is awesome. But now I don’t know what to do. So, what do you think about buying the course with some of the money that we got from this project?” And of course she was all for it, because we had just proven the value of it right off the bat. So we joined the course, and WP Elevation has been just an unbelievable force in our life. Because not only is it training, it gave us the tools and some of the processes and things that we needed to run a better agency, and just in general, just to make sure our agency was going to be profitable and sustainable in the long run. But more than that, it gave us a community of like-minded people, who were trying to do the same thing that we were trying to do. And that constant encouragement and seeing other people succeeding and wanting to do what they were doing… It just put us in the right frame of mind to be ready to go out on our own and not have that safety net of having a full-time job anymore.

Colleen: Right.

Alyssa: I will say, for anyone listening who is a spouse, he makes it sound like I said yes right way. There was some convincing there.

Robert: Yeah, it may have taken a few days.

Alyssa: I will say, it was valuable. But yes, being a spouse of someone who likes to spend money on education and learning. You have to choose which ones you think will be helpful. So, yes, there was a little bit, still, convincing there.

Robert: I might be a little bit of an online course junkie.

Colleen: Yeah, you might. So I know you guys travel all the time, that’s one of your motivating factors for going out on your own. So how do you handle that with working remotely, and what do you tell your clients? Do they even know you’re gone? Do they care? How do you get all that to work so you can run your business?

Robert: Well, most of my clients have no idea that we travel. Occasionally, if we’re actually taking time off, I’ll setup an autoresponder in the email, and let them know we’re out of office. And if there’s something going on I’ll preempt that by sending an email to the clients that have active projects, saying “Hey, just so you know, we’re out of office next week” or whatever. But, for the most part, as long as I know I’m going to have a solid internet connection, we don’t really bother telling our clients because it doesn’t really affect them that we’re working from Branson, Missouri, versus working from our home outside Chicago. They don’t ever come and meet me in person anyway, with rare exception, so it’s not like they’re not able to come meet with me when they need to. We can always do video calls and things like that. So, for the most part, I’d say 90% of our clients have no idea that we travel as much as we do.

Colleen: In a given month, how much travel time do you think average?

Robert: Well last year, 2017, we were away from our home for just over 16 weeks out of the year.

Colleen: Wow.

Robert: And that’s overnight stays. We have a few day trips here and there. Mostly it was … mostly when we traveled it was overnight stays, and there were just over 16 weeks last year. So, yeah, we do travel a little bit. We’ve cut back a little bit this year as we’re preparing for some other projects we’re working on. But it’s definitely something we enjoy doing. The biggest thing is we like to travel and see people, and friends of ours. You know we’ve made all these connections with people across the country and even around the world. I like traveling to Washington, D.C., to see all the different museums and monuments, things like that. We like going to Branson, Missouri, and seeing all the attractions and shows and stuff there. Or going to Dollywood in Tennessee. But as we go to all those places, I also love going to meet up with these people that I’ve known for sometimes years online and never actually met in person. And so we’ll go and we’ll have dinner, our organize a Meetup with several of them if there’s a bunch in the area, that kind of thing. So that’s been a really awesome perk of traveling, is getting to meet all these people on person. You forge a different type of relationship with people once you meet them in person versus just online and Facebook and whatever else.

Colleen: Like technologywise, are there any other considerations that you need to have when you’re traveling so much?

Robert: The only thing that we found to be really helpful, is we made sure we got a cell phone plan that allows us to tether with our phone, or use a hotspot with our phone. So if we happen to be somewhere that the internet is just terrible, we can turn on the hotspot on our phones and still be able to work. For the most part we’ve tried to build our business to the point that we don’t have to be in there every single day doing something. It’s not mission critical for us to be online every single day working, other than answering a few emails, which we can do from our phones. We don’t have to do anything. We tried to build it that way, but if we do absolutely have to be online and working on something and we don’t have good internet, a cellphone hotspot has been a lifesaver on more than one occasion.

Colleen: And you know, some people are fine being freelancers, and they don’t necessarily want to have a team or anything like that. But you guys now have a team, and you guys started out just working for yourselves and then you added people. So what has that done for your business?

Robert: Well, I will say technically from the beginning, we’ve always had a team. Because I’ve done some things and Alyssa’s done the others. I know there’s a lot of people out there that their spouse is not a part of their business or maybe they’re not married or whatever, or their significant other doesn’t have any skills that are applicable to a creative business or marketing, or whatever. But we’ve both been blessed to have each other to help kind of compliment … complimentary skills. But bringing on a team has absolutely opened up our eyes to what it’s like to be a business owner, and not just a job owner. Because most of the time when you start your own business, you’re really not starting a business, you’re getting yourself a job.

Colleen: Right!

Robert: Every single day, you’ve still got to get up, you still got to the office, which is down the hall or across the room or whatever. You’ve got to open up the computer, you got to do your work, and you probably aren’t going to work 9 to 5. You’re going to work longer hours than that. You’re going to work on weekends. And that is fine but if you’re going to do all of that, it’s better to do that with an end goal in mind. And our end purpose was to eventually get the point that we’re no longer doing that. Because we own a business where other people are doing nine to five work and we’re just overseeing and managing and running the business side of things. Setting up the strategy for the business and the marketing and the direction and kind of guiding as the business grows. So hiring a team has been an interesting process. And we’ve learned a lot of things as we’ve gone through it, but it has been one of the biggest stress relievers for sure. When you remove that burden of, okay I’ve got to get these 12 things on my to-do list done, and you change it to, alright, well I really need to do these two things If I get around to it. It makes life a lot easier.

Colleen: Having your own business has also allowed you guys to have your side projects as well. Those are really exciting.

Alyssa: A few years ago now, I came up with an idea to make rain boots that have wraps on the outside. So you just have one pair of rain boots and you can switch out the pattern on the outside. Well, we did not know the journey that that would take us on, trying to get a patent for that. We had many struggles, many setbacks trying to get the patent, trying to get manufacturing, all that going on. About a year and a half ago now, I got a call from my patent lawyer and I assumed it was another call explaining why something did not work, or why we were denied, and what we’d have to do to fix it, which each time costs more money. He told me that we were approved, and so we officially have a patent for the idea of rain boots with wraps on the outside of them. That was super exciting. And that was a just a huge, huge win for everything we’d been through. Currently, that business has kind of been put on the back burner just because we had to build up the business that was making money.

Robert: Right, so Aly’s Boots was an idea that Alyssa had before we were actually working full-time on our agency. So this is something that’s been going for probably three or four years now. While we’ve been working on that and putting money and time into it, we got to the point that I wound up quitting my job and we went full-time with the agency. We quickly found that selling digital marketing services has a much lower overhead with a much higher rate of return then retailing women’s fashion rain boots. So we put our focus on that to get us to the point where our income is stable and we have a salary coming out of the business, and we’re to a point that we’re comfortable with the agency work. Then we’re going to pick back up, trying to market Aly’s Boots and things. I will say the patent attorney told us we’d have about another year and a half until we got the patent. So we had intentionally planned that we’ll just put this on hold until we get the patent. Then we got the patent about six months after he said that.

Alyssa: So it was very, very unexpected.

Robert: Yeah, it was out of nowhere. So we’ve still got it on hold but that actually is part of our plan to kind of pick that up once we get a little further down the road.

Colleen: And I know you guys love Disney, so what else has having a remote business allowed you do to that feeds into that love of Disney?

Robert: Well, obviously with our traveling, we get to go to Disney World. We’ve been more than a few times in the last year. I think in the last year we’ve probably been … I don’t know, six or seven—

Alyssa: I was going to say six.

Robert: Yeah, probably six times to Disney World.

Colleen: Wow.

Robert: And I should preface that by saying, I grew up in North Carolina and it’s about a 10-hour drive for my family to go to Disney World, and my family went there twice a year. My dad got two weeks vacation, we would go one week in the spring, or in the early winter in January, February. And then we’d go again in the fall, or right before Christmas. And that was our family vacations every year, because it had something for kids of all ages. I’m the oldest of 11, so there were kids of all ages in our household at all times. So we had to go somewhere that I could enjoy things as a 16-year-old, but then my 4-year-old brother could also enjoy it at the same time. So we would go to Disney World a couple times a year and that went on all the way until I went to college. Even in college, I hopped on a plane and went down there to join my family at Disney World a couple times throughout my college career.

Alyssa’s family went a few times when she was a child also. But then once we got married, again, we were working our jobs and kind of tied down and didn’t have much vacation time. You know how it is when you first start out, and you’re kind of the low man on the totem pole. So we didn’t go to Disney World … or actually we didn’t take any vacation at all for the first two years we were married. And as soon as we were able to take a vacation, we went to Disney World, and we were like, yeah, we need to do this more often. And that kind of led into … once we quit our jobs, it was like, okay, let’s go back to Disney World more often and do this.

So it’s enabled us to do that, which, if you didn’t know, Disney has wifi in all the resorts, which is all I need to do my job. So, that was kind of a …  Yes, we do go to Disney Word. Yes, we also work while we’re there. Generally, I get up in the mornings around 6 or so while we’re there and I’ll work until 8 or 9 o’clock and then we’ll go to the parks. And then after we come back from the parks, I’ll work for an hour or two before bed, and repeat the next day. So it is not as much of a vacation as other people, but I always say, I’d rather work from Disney World than work from anywhere else.

Colleen: Yeah, most people don’t get to say that. But you guys are now turning that passion into a business.

Robert: That is what we’re doing, yes.

Alyssa: Yes, we are.

Robert: We are in the middle of planning a huge new project that is now becoming the most terrifying thing we’ve ever done. Because quitting my job was crazy and it was scary, but this is making that look like child’s play sometimes. Because what we’re doing is, we are selling our home, and most of everything that we own, and we’re actually moving to Walt Disney World for the year of 2019. So beginning on January 1st all the way through the end of the year, we’ll be living at Walt Disney World for the entire year—not living in Orlando or whatever, we’re actually going to live out of the 32 different resorts that are on Walt Disney World property.

Colleen: Amazing.

Robert: Yeah, it’s kind of crazy, it really is.

Alyssa: It is crazy and we’re aware of it.

Robert: That’s right. But, you know, embrace the crazy. Our plan is to turn that into a business down the road by monetizing the traffic that we’re getting and monetizing the list that we’re building and things like that. But ultimately our goal with it, is to help people plan a better Disney vacation. Because when you go to Disney World now in 2018, it’s very different than it used to be. You don’t just book a hotel, buy some tickets and show up and then do everything. If you really want to take advantage of everything there is there … if you want to ride the best rides, if you want to eat at the better restaurants, you have to plan your trip at least six months in advance. And you have to make your dining reservations six months in advance and then you have to plan which rides you want to ride with the Fast Pass system 60 days in advance.

So there’s a lot of planning that goes into it. And for someone who’s never been or has only been once maybe five, 10 years ago, it’s incredibly overwhelming. And there’s a lot of bad information or misinformation out there on the internet when you try to plan. So what we’re going to do is, give people a resource to help them plan the trip better. That is not just saying, okay here’s all the restaurants and this is what we think of them. But we’re going to take a little bit different approach, and we’re going to review them based on how good this restaurant is for people who have allergies. What is this restaurant rated for people with children? Is this somewhere you’d want to take picky eaters? Is this the place that you want to go for a romantic evening out? That type of thing on the restaurant side and then, of course, the rides. We’re going to review which are good for small children, teenagers … whatever. And then the resorts, we’re going to do the same thing. Trying to help people understand, okay, these are your options. You have 32 different resorts with over 140 different room types that you can choose from. How on earth do you narrow that down and pick one?

So we want to give people a starting point. So instead of saying okay, I’ve got to look at all 32 resorts, we can say okay, here is … you’re a family of five, you have three young children. These are the top three resorts that we would recommend and then you can go and look at those three resorts, and see which one you like the best. And from there, then we’ll say, this is how we would recommend you choose a room category. And they can pick their room category that way. Just kind of give a little more of a guided process to choosing and planning your Disney vacation.

Colleen: That’s great, because it’s just like you took … you saw a need in that market, and then you took that and combined it with your interest in it and developed this whole idea for this business.

Robert: All these things that we’ll be doing in 2019, we’ll be doing on our website, Here With the Ears, our brand, because we’re going to be there at Disney World with Mickey Mouse and friends.

Colleen: So if anybody is thinking about leaving their full-time job, and going out on their own, are there any things that you would do differently? Or are there any things that you would highly recommend that somebody do before they do that, and then try to pursue their dreams?

Robert: So before someone quits their job, I would highly recommend making sure that you have your personal life in order to some extent. If you have $800 a month in student loans, and a $1,200-a-month mortgage, and your utility bills are $300 or $400 a month, plus you have credit card bills that are $300 or $400 a month. If you have those type of burdens on you, it’s not to say that you couldn’t succeed by quitting your job and starting your own business. But it’s going to make it 10 times as stressful for you when you quit your job. The guaranteed income … as guaranteed as it can be when you have a job that you have gives you a little bit of stability.

Because you can budget and you can plan. And say okay, well I do have a $1,200 a month mortgage, but I know that this paycheck pays for the mortgage and the next paycheck pays the rest of the bills. When you have your own business, it’s so much easier to sleep well at night knowing that all I have to do is come up with $1,500 this month, and my bills are paid, or $1,800 and my bills are paid. Instead of saying, “I’ve got to find some way to come up with $2,800 before this month is over, and then I’ve got to do it again next month, and the next month, and the next month.”

And then the second thing I would recommend, above anything else, is find a way to build recurring revenue in your business. I don’t care what your business is, or what you’re doing, or how you’re doing it. Figure out a way to get people paying you money on a monthly basis. Because that is how you can bring some of that stability into your life as a business owner. And that’s how you have that peace of mind of, okay, if I’ve got say, $1,000 a month in recurring revenue, and I need to bring in $2,500 a month in revenue, it’s a lot easier knowing that first $1,000 on the first of the month is already taken care of.

So all you’ve got to do is come up with another $1,500 throughout the rest of the next 30 days. Besides that, getting some training along the lines of what you’re trying to do and joining some communities of like-minded people will be super crucial in trying to make that jump. And when you get to the point of being ready to, because it can be lonely as a small business owner, freelancer, whatever you want to call yourself—especially if you don’t have your spouse working in the business with you, like I’ve been fortunate enough to have.

So it’s really, really helpful to have a group of people that you can go to and say, “Hey look guys, I’m going nuts right now. I hate my life, I feel like a failure. I need some help.” And having that community to come behind you and say, “Oh it’s okay, you got this. Like what can we do to help?” That right there is how you can get through it once you finally pull the trigger, because there will be days that you feel like that. Having that community can be the difference between success and failure.

Colleen: Definitely. I totally agree with that. Okay great well, thanks so much for being on the podcast. I can’t wait to hear what happens with all your other side projects too.

Alyssa: Thank you for having us.

Robert: Yeah, we appreciate it. We’re definitely big fans of yours.

Colleen: Thank you.

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