Rasheid Scarlett is the owner of Great Dwellings, a short-term rental property management company that helps property owners maximize their short-term (i.e., Airbnb, VRBO) vacation rentals. Great Dwellings helps busy vacation rental owners through expert marketing, optimized pricing, guest screening, handling key drops, cleaning, guest transportation, maintenance, and more. Rasheid is also the CEO of NetAesthetics, a company that provides a broad, deep spectrum of technology services to help organizations translate their strategic business agendas into IT initiatives and solutions that measurably improve performance. In April 2020, Rasheid furthered his mission of building amazing solutions and experiences by joining the Forbes Business Council.

Rasheid learned a work ethic from watching his entrepreneurial-spirited mother, and used it as a means to escape hunger. After facing uncertainty on where he fit in while attending Wheaton College, Rasheid found his footing and scaled his professional career into something remarkable. Through his companies Great Dwellings and NetAesthetics, Rasheid is able to put food on the table for nearly 40 employees and their families. A family man at heart, Rasheid’s principles allow him to approach his personal and professional life with love at the center of everything he does.


BRYAN WISH: I know Rasheid doesn’t want to brag here but he ordered equipment in D.C. Had to go to New York, buy the equipment again. So kind of him. He could have easily cancelled. I’m thrilled to have you here. 

RASHEID SCARLETT: I’m glad to be here. That’s why I wanted to make sure I didn’t mess up your sound quality.

BRYAN WISH: What’s the One Away moment that you want to share with us today?

RASHEID SCARLETT: I’ve been thinking about this. The titles of all your things are One Away from different things. I feel my One Away is hospitality but my moment was as a teen, my family and I were kind of down on our luck. We were walking through a chow line just to get dinner literally amongst homeless people. We weren’t exactly homeless but walking through that chow line was the only way we were going to eat. Zero food in the fridge. It was about 9th grade. I remember that as being kind of a trigger moment for me to excel. 

BRYAN WISH: Growing up, were you finding yourself in a very similar spot where there was a constant struggle for food or a constant question of where am I going to sleep tonight? 

RASHEID SCARLETT: It wasn’t a constant struggle for food. I’m super proud of my mom. Though we were often on different government programs, she really made an effort to get off before – you age off or you make too much and they kick you off. She’s like, “Look, we’re getting off that program now even though we still qualify.” I was always proud of her. That’s where I saw the vision was in her. “Yes, this system exists but it’s not a crutch I’m going to lean on.” She was really entrepreneurial. A lot of her ventures never manifested but it was the seeing her begin them planted that seed in me that said, “I can start that business.” She started a curtains business, a bedding business, a shorts business,” because she was a seamstress. Each time, I was like, “This is going to work, mom. This is going to work.” I saw it in her. It was that drive. I feel that’s my One Away – seeing my mom’s each idea. They never manifested but that really was inspiring. 

BRYAN WISH: Despite the circumstance of how you grew up, you saw your mom really show anything is possible. It didn’t manifest into a huge business but you saw that desire, that dream to create something of herself to create a better life for you guys.

RASHEID SCARLETT: We could barely afford fabric but she was like, “If we can get enough fabric together, we could make shorts.” It was a need. I couldn’t afford the nice, fancy shorts that other kids would have. She’d go to the fabric store, buy the pattern, buy the material, make the shorts for me, and say, “You know what? That cost us four bucks. Maybe we can make 100 of them.” That’s essentially what happened. 

BRYAN WISH: How did you know the drive was there? Once you felt that, what next steps did you take to plot a better path forward in your life? 

RASHEID SCARLETT: The being hungry moment, I remember it so clearly. I opened the fridge and it was clean. It looked like someone cleaned it spic and span. The only thing in there was the bologna. There was one slice in there. Then I almost felt guilty. Am I going to take the last morsal of food? I can’t blame anybody because my mom was trying hard but I can’t have more moments like this. This is definitely pretty terrible. Legit hungry. My mom worked hard to make sure I always went to a good school. I was in a private school that gave us a scholarship. We didn’t pay a penny which was pretty awesome. I remember thinking, “I’m going to make the most out of this.” I saw families driving in nice cars and I think we had a 1970 something, super long car because it got handed down to us and I won’t say it was greed but it was what I was baselining as my normal. In 9th grade, you’re just kind of figuring out your baselines. I just wanted to hit that normal. That was really my goal. It wasn’t to be a rapper from MTV or even a basketball player. It was, “If that’s normal, I’d like to get to that.” 

I started to kind of see that hard work paid off. Hard work became my MO. Then it became such my norm that things were paying off and it was like, “I can keep working hard. I can do this. I know how.” That’s been kind of an unintended consequence where things have continued to do well. 

BRYAN WISH: You had a significant driver that clearly said, “I just don’t want to have to struggle as much.” The blessing of having the scholarship to private school is you saw the different life that was possible. 

RASHEID SCARLETT: Definitely a true blessing, for sure, and the example of a hard working mom. Yeah, we struggled at times but seeing what hard work looked like. I think she just had a couple of unlucky bouts. It wasn’t that she wasn’t a hard worker. They just didn’t pan out into keeping food on the table regularly for us. Hats off to her regardless.

BRYAN WISH: It sounds like she created an environment with zero limits. You said those molding experiences engrain this sense of hard work in you. Let’s go a little deeper on that. Where you finding your pursuits being channeled and your work ethic being channels after that?

RASHEID SCARLETT: In 9th grade, I remember I was the AV guy. Back in my day, TVs were huge and they were on a cart. You had to literally roll the cart into the classroom and the teacher would kind of request, “Hey, I want a TV in my class tomorrow.” I had an afterschool job to make a few bucks being the AV guy that would go set up the VCR and the TV in each classroom. It didn’t feel hard. It was what I had to do to kind of generate a couple bucks. From there, in college, luckily I got a scholarship there as well. I took a second job there. Yeah, I got a scholarship but it was like, “I’m not going to use my idol time.”

We had a travel agency and I was the guy that worked at the travel agency.” In fact, I screwed up one person’s trip. Huge. I put the wrong weekend. He went to go to the airport and it was literally the wrong dates. He came in so politely and said, “Hey, I didn’t get to go on my trip.” He was so nice about it. I remember that being kind of a trigger mark of, “He could have went ballistic and almost, rightly so.” It helped me almost think – I remember it so clearly. Be a good person no matter what. Someone literally messed up his chance to go home and see his family and he was such a nice guy about it. Yes, hard work was instilled with almost a sense of courtesy. That moment made me think you can be nice no matter what. Someone can mess up. I’m sure they didn’t do it on purpose. Almost in every case. 

BRYAN WISH: You were probably freaking out at that. 

RASHEID SCARLETT: Yes. He should be mad. I’m going to lose my job. Oh, my gosh. He comes in like, “Hey, I didn’t get to see my family. These were the wrong dates. Is there anything we can do.” I was like, “Note to self. Don’t be an A-hole.” 

BRYAN WISH: That’s a good lesson to learn early. Where did you end up going to school?

RASHEID SCARLETT: Wheaton College in Chicago area. 

BRYAN WISH: What led you to the travel agency?

RASHEID SCARLETT: There was literally a list of jobs and that was the next available one. It wasn’t a please hire me as a travel agent. It was the top on the list and I stumbled in it.  That’s funny. I guess that’s where I ended up years later. I didn’t make that connection until just now. 

BRYAN WISH: It’s funny when we do things without realizing and it takes a path that connects all the dots. From high school to college, it seems like you had this drive. You were going to figure it out. It didn’t really matter at what but you were going to find an opportunity to seize the moment and then figure out a way forward. Yeah?

RASHEID SCARLETT: Yeah. I don’t see this as a video patting me on the back. I think it was trying to find a way for it. It wasn’t I had this drive to strive. It was, “How am I not going to be hungry?” It was almost a run away from negative. It wasn’t a drive for excellence as it was a, “I know what I don’t want to experience anymore. Then I think it has now manifested in a drive for excellence 20 years later. 

BRYAN WISH: If you could go back to… You’re in your 40’s?


BRYAN WISH: Audience, he looks like he’s 36. If you could go back to your 20 year old self, what would you tell yourself then from what you know today about yourself? Describe that 20 year old. Who was Rasheid at 20 years old?

RASHEID SCARLETT: I was a computer science major. I’d stay up late writing code for computer science class. I loved every second of that. I was also a mediocre athlete. I made the football team but I barely got any minutes. I was the basketball manager which is definitely not the most talented guy on the team. I was barely on the team. I just traveled with the athletes. Everything in life has a balance. There was a point where I was trying too hard to be the fun kid and have fun. Then there were points where I think I had overdone the study and the library. I should back up. Freshman, it was the study, study, study. I can’t F this up. I don’t want to lose this scholarship. Then I made the football team and I was like, “I’ve got to hang out with these guys. I’ve got to be the cool kid. I see the cool wide receiver. Let me be like him.” Then finding that balance a little bit later which was closer to my senior year with something that I should have done earlier. Right after that, I then overdid the whole work late, work late and I was missing out on friendships and experiences. Finding that balance again. It was a pendulum switch. 

BRYAN WISH: Was it a struggle for balance or a struggle for belonging?

RASHEID SCARLETT: That’s a great question. I think there’s some truth there. I wanted to belong on the football team. I wanted to show the school that they didn’t mess up by accepting me and giving me a scholarship. I didn’t fit in the computer science crowd. There were some nice guys and they were definitely nice to me but I didn’t really fit in there. I didn’t quite fit in on the football team because my mom didn’t let me play football in high school. I made the team for athleticism but I didn’t make it for my football know-how. I didn’t have it. That’s half the reason I didn’t get a lot of playing time. Afterwards, I got out and I was trying to find myself as a young adult. Where do I belong? What’s the crowd, the demographic I belong in? Am I yuppy? Am I a what? Just working hard to not fail was important for me. I think you asked a really good question. It is a little bit of both. 

When I got out of college, I was one of the few college graduates in my family. That came with a lot of socioeconomic things. My family grew up in the 90s and the 80s was really tough for a lot of people. As I’m learning now, kind of inner city, black people kind of had this struggle that set them in a weird trajectory. Then my mom found an escape. Got us to Syracuse and got me out of that life. Then me, being the first college graduate, I was the one person with a recurring income. I made $49,000. At the time, I thought that was a ton of money until I sent some to my grandmother every month, my mom every month, pay my bills in New York. I had to have a roommate. I actually didn’t make as much as I thought. Splitting that money up a lot of different ways ended up making me realize I do have to work a bit harder to earn more to survive and for my family to survive. It wasn’t just about me.

BRYAN WISH: You graduated. You worked hard. You did a good job after school and you had to start sending money home to support your family. It probably gave you a deep appreciation for work ethic even more so. 

RASHEID SCARLETT: Yeah, it felt good to be able to send it. Mom needs it. I can do it. My mom had a lot of ups and downs and there’d be times where things would be well and then rent would fall behind and then me being able to help her stay in her place, that’s a great feeling to be able to help someone who has helped me so much. My grandmother, just being able to make sure that she can smile. When you can hear the smile on her, that was enough. That was a great feeling. 

BRYAN WISH: It feels good to give whether it’s money or act of service. It feels good to meet someone in a deep way. Good for you. What a mature, responsible act at a young age. I’m reading a book right now called Braving the Wilderness. The subtitle is In Quest For True Belonging. It actually made me really shift my whole view on what it means to belong. When in your life did you start to feel you could really start standing fully in your own shoes and have this sense of confidence in that person you were. Do you have any moments that stand out to you?

RASHEID SCARLETT: There is a moment. A friend of mine, Phil Edwards, a great guy, mentioned something to me about how he admired me. I was blown away. So much that I thought he was joking. Admired me? I’m still figuring this out. He started listing a few things. I say this humbly. All this may not sound humble but I really truly mean it. I was, “Oh, I guess things are okay.” I kept moving my own finish line. “Man, if I only made $100,000. If I only had a home. Oh, people are real estate investors? Maybe I need an investment property.” I kept pushing my own finish line and I was never satisfied. He kind of took a moment back and said something about either he admired me or I was admirable. I truly thought he was joking. When he said it, I was like, “Wow.” I took me a moment to say, “I could stop this whole moving my own finish line and pause and take a breath. Stop and smell the roses a little bit.” 

BRYAN WISH: How old were you?

RASHEID SCARLETT: I think it was about 10 years ago. Mid-30s. It didn’t stop my drive. It was like an obsession, to a point, that was almost unhealthy. It let me wake up to say maybe chill on the obsession. That balance. 

BRYAN WISH: You had some pretty hard, subconscious drivers behind the work ethic. 

RASHEID SCARLETT: Yeah. This is not a feel sorry for me story but I was trying to figure out how to start a business. I was an employee and what I saw as next level was business ownership. I started a little LLC with an EIN. I tried to apply for a small business administration thing and it said, “Do you have multiple clients and do you earn X amount?” I was like, “No, it’s just an EIN.” Then I went and I got a client which was a company that contracted to Fannie Mae or whatever but it wasn’t enough to cover my bills. I literally worked there after my day job. I literally would drive to my day job to this site that wanted me to work night shift. I’d sleep under the desk because they thought I was working night shift but I was also working day shift. I literally had two 40-hour a week jobs. That second one didn’t make enough but I thought this will meet the SBA requirement. I’ll be a real business. It actually worked out great. Now that night job is a company I own that’s legit and real. It was a little excessive too. Was it really necessary? It worked out. Maybe it was. It was a little much.

BRYAN WISH: What did that night shift turn into?

RASHEID SCARLETT: As much as I am into hospitality, I own a company called Great Dwellings. We have a small hotel in Mexico and we manage 100 properties across the U.S. I also own an IT company that does really well. We won a multi-million dollar contract to sub to the federal government and we have a bunch of small businesses. It manifested into that. That exact same LLC and EIN number that I was trying to make legit for the SBA was a little gig that is now a company that helps me employ a few people. That company is called NetAesthetics. 

I have to backup really quick. I read a book by Obama’s wife, Michelle called Becoming. Early in the book, she said one thing that bothered her is when her teachers or grownups would say, “What do you want to be when you grow up?” As if it was a singular thing. I always think of it as, “Well, little kid, what do you want to be when you grow up?” Well, I’ve been able to have a successful IT company and a successful hospitality company and some people are like, “What are you going to put on your LinkedIn page?” It’s like, “Both. It is what it is and I’m not really embarrassed. You don’t have to be one thing.” I’m no Bo Jackson but he was a great baseball player and a great football player. I’m no Deon Sanders. It’s doable. Kids need to learn that. I’ve been trying to teach my kids you can be more than one thing. 

BRYAN WISH: You’re multi-faceted. Your jobs not your only identity too. Who you bring into fatherhood, marriage, all the parts of you. Your job clearly is what’s making it possible but I’m sure you show up in the areas similarly. 

RASHEID SCARLETT: I love being a dad. I love it. That is exciting.

BRYAN WISH: Tell me more about that.

RASHEID SCARLETT: I’ve got four kids and one on the way. I’ve got a 23 year old who was conceived while I was in college. Amazing kid. He lives in Chicago. I actually look up to him. He’s more balanced than I am. I’ve got 13 year old twins. One is a great soccer player and got invited to Barcelona to play in Barcelona. We went and that went really well. My daughter is the best artist in the world. I have a three year old who is in the other room. If this microphone is as good as it said on the box, you may not be able to hear him. He has definitely called my name throughout this podcast. Amazing. Just a fun, three year old. Then my wife is pregnant. Actually in the hospital at the moment but they won’t let kids in. It’s not like I’m skirting my responsibility as a husband. I spent all day with her. Now I have to do daddy duty at home because they won’t let him come visit her which is a little sad because of COVID. 

BRYAN WISH: I bet you wish you were there.

RASHEID SCARLETT: I do. I wish she could get a hug from the three year old. He gives the best hugs. I think she’s on day five now. I’m sure she could use more than just my hugs. 

BRYAN WISH: What a special time for you and your family. That’s great. 

RASHEID SCARLETT: Yeah, I’m excited. We’re up in New York. My wife has a job up here. It’s a temporary assignment. Luckily, being an entrepreneur, I can kind of support her from wherever she is. 

BRYAN WISH: Nice flexibility, for sure. I’m stoked for you and your family. Boy or girl?

RASHEID SCARLETT: Girl on the way. That will be three boys, two girls. 

BRYAN WISH: You’ve built a couple of businesses. You have family. You’re doing things for yourself in a way you never have. When you think about legacy or what you want to leave behind, what does that look like to you?

RASHEID SCARLETT: What I want to leave behind is mindset. Not necessarily assets per se. I definitely would love to have a couple pieces of revenue generating things for my kids to fall on but I want them to have the mindset of… The Mexico hotel is called DEWL (Do Everything With Love). It’s that mindset that I want them to – I want my daughter to draw with love. I want her to pour her heart into that. I want my son, if he’s going to stick with soccer, to do it with love. Not just half way, “At practice, I’ll practice.” I want him to do it with love. If he grows out of that, if he takes over one of my businesses, to do it with love and if my daughter does. It’s almost that drive you’re talking about but less of a greed and more of a love. 

I love that Great Dwellings, we indirectly employ 38 people. Some are contractors. Some are employees. Some are vendors. Knowing that I can help 38 families put food on their table, how cool is that? That’s it. That’s winning right there. It’s a small business. I know there’s companies that do 38,000 but if I can do my part. We do it with love. I want to make sure each place is furnished and decorated with love. We’re putting together Ikea furniture, do it with love. You can see that bookshelf when it’s not put together with love. You can tell. When you’re cooking, you can taste when someone cooked with love. Did they leave the room and they were also watching Netflix or were they really putting their heart into it? That’s the legacy I want to leave is do it with love.

If you’re going to build a business that has surplus revenue, can it also do good? And not do good for the sake of branding, “I want everyone to buy my stuff because I say I also give to charity.” Great Dwellings has given to charity and it’s written nowhere on our website. It’s actually because I just don’t want to flaunt it. It might end up on there. That’s not why we do it. That’s the legacy. Whatever you do, do it with love. I think it will turn out great almost. I can’t even think of an example. If you do it with love, either you’re just going to enjoy doing it. Let’s say it doesn’t end up being big but you came away feeling fulfilled doing it. More times than not, it actually will manifest into something successful. I’m not spiritual enough but I’m sure there’s some supernatural thing that’s happening when you do something with love. The completeness of it embraces that love. 

BRYAN WISH: You have to bring your whole self to the table. That’s beautiful. I’m envisioning 20 years down the road, a book called DEWL. It’s inspiring. It’s also subliminally thinking about when you don’t do something with love. It’s kind of a guardrail. It’s kind of a sign that you’re not doing something aligned to your core. It’s a nice, simple way of checking in with yourself. 

RASHEID SCARLETT: Going into the lack of spiritual vocabulary for this, I used to dabble in digital design when I was building the IT business. There would be times where hours would pass away where I would just make something and I’m loving it. I’ve got my favorite tunes playing. You’re just so in the zone that nothing else matters. Almost like Michael Jordan when he’s playing. You could tell he was in the zone. That zone is a version of the love. I’m literally nudging one pixel over because it doesn’t feel just quite right yet. Then I feel you can kind of step back like an artist when they’ve done that last little droplet because they did it with love. 

BRYAN WISH: I think that’s bold. I think it’s powerful. It should be a family motto. I might have to take that for myself. If you have any artwork for me, send it over. 

RASHEID SCARLETT: Let’s just make it a thing. Do it with love. Do everything with love. I even tell my wife – I was teaching her how to drive. She learned how to drive while we were dating. I was like, this is a community thing. We’re all on this road together. We all have a shared goal of getting to our own destination. If someone swerves over two lanes, you know what? Hey, you probably missed your turn. I don’t think you were being an a-hole. You were maybe a little self-absorbed in the fact that you heard your Waze direction a little too late but do it with love. Let’s drive. Let’s get to our destination. We’re all trying to get to our destination. It’s not just me. We can all win. 

BRYAN WISH: I love it. Such beautiful simplicity to that statement. This has been amazing. Let’s go rapid fire.

RASHEID SCARLETT: I’m not good at that but I’ll try. 

BRYAN WISH: Favorite book and why.

RASHEID SCARLETT: The 4-Hour Hour Workweek taught me a new mentality on working. 

BRYAN WISH: If you could cook a meal for your wife and do it with love, what would it be?

RASHEID SCARLETT: Yesterday I made this amazing ravioli with red sauce and parmesan. It came out so good. I grilled it a little bit so it was sauteed. It was awesome.

BRYAN WISH: If you could travel anywhere in the world and spend a week there fully immersed in a place?

RASHEID SCARLETT: I have visions of seashells where it’s tropical. There’s little technology. Just embrace yourself in the water, in the trees, and kind of get away from everything. Less tall buildings. Less fast cars. That sounds like a destination for me. 

BRYAN WISH: Your one wish for your newborn coming into the world.

RASHEID SCARLETT: She finds her destiny and she’s able to do it with love. Whatever it is. If it’s philanthropy. If it’s art. If she’s a soccer player. That she feels that joy when she does what she does. She’s won. I won. Everyone wins. 

BRYAN WISH: This has been a blast. I so appreciate you showing up and bringing yourself to the table. This was a great way to end a Friday. Where can people find you and reach out?

RASHEID SCARLETT: The easiest place is LinkedIn. Rasheid Scarlett. It also pops under Karl Scarlett. My middle name is Carl. I go by both. I dabble on the other social media but sometimes I’m off for weeks at a time. 
BRYAN WISH: Thanks so much. I hope you have a great weekend.