From Gumballs to Real Estate: A conversation on Lessons in Hustle and Investment with Besa Gordon.

Recently, I had the pleasure of sitting down with Besa Gordon for an in-depth conversation about entrepreneurship, innovation, and investing in oneself. Forget swag, Besa’s dope! this conversation was a meeting of the minds.

Besa is a Seattle born and raised entrepreneur, in 2009 she created Naybesa.com to speak her mind on Hot topics, news, music, pop culture and the PNW.  As of 2016, Besa has been the lead blogger for Seaspot.com, created two radio shows on Go Juice Radio, created Naybesa TV, and now has her own digital marketing company where she excels at helping artist create an online presence and get their music noticed.

We discussed my journey from purchasing a modest 311 square-foot studio to developing a real estate fund and launching multiple business ventures. In this interview, I share insights on financial literacy, the importance of taking risks, and how to turn opportunities into profitable ventures. Join me in a conversation with Besa on my experiences and offer some tips for aspiring entrepreneurs looking to make their mark in today's competitive landscape.

The following is a transcription from our conversation:

Besa: Recently, I had you on my other show, and we did a deep dive into Jaebadiah. One of the things I really love is that you make money in so many ways, all the way down to having a gumball machine right in front of your office. You have different ways of making money and literally funding your life and helping others.

Jaebadiah: Yeah, I appreciate that. You know, I am not about to give away all the gems, but I am a businessman and entrepreneur, and yes, I do sell gumballs. This is true. About 24 years ago, I moved my office and Ali moved out of my apartment. I was right there, and I walked out of my office and said to myself, "Where are people getting this gum?" So, I decided to buy the gumball machine, and it does quite well. It’s really amazing because I’m able to use some of the proceeds from that to support some local folks who are going through transitional housing. They know I’m there, right? So, they’ll come to the alley and ask for a little something, and I’m able to help them out to keep them going. It’s about being an opportunist. I see something and go for it, and that’s just one of the little things I have going for sure.

Besa: Now, I know that you call yourself an opportunist, but let’s talk a little bit about that mindset of finding different ways that are out of the box to make money. 

Jaebadiah: I think that a lot of people are in this position where rent is expensive, gas is expensive—like an Uber for about 2 miles is around $20 right now. I don’t look at it as just being an opportunist. I look at how I can solve a problem. How can I solve an issue? And then the secondary question is, is there a way to monetize it? If you’re not really solving a problem, you’re probably going to struggle with monetizing it. A small example is just selling gumballs. The issue was there was no gum supplier in the alley. For me, it was rocket science—it wasn’t like I racked my brain over this. I saw people needed gum, so I became the person who supplied the gum. 

It’s really cool because it adds to the fabric of the tourist attraction in Seattle. It’s another thing for people to do when they come to Seattle—they get to stop by the gumball machine, take selfies. It makes the city a little bit more interactive. But at the end of the day, it’s not about the money for me. It’s about what issue I can solve, and then how to monetize it. You don’t need to go out and make $100,000 with one hustle. If you have eight $10,000 hustles, that’s $80,000. Then you find ways to be efficient, making sure your system of those different hustles is efficient. You spend less time making more money. You develop processes, build a team, and then suddenly you have some time and cash on your hands to explore another opportunity. It's about solving another issue that can potentially become a monetization model.

I think entrepreneurship is something organic within our people. We’re already adventurers, entrepreneurs, and innovators. It’s just a matter of actually doing it—taking the risk and doing it. Put up a few hundred dollars on yourself, gamble on yourself. You go to Vegas and blow a stack on a Friday, why not invest in yourself instead?

Next time you give your money to the dealer in Vegas, you're not getting it back. You don't learn much other than that you got a crappy hand. Sometimes, you spend $30 or $40, but at one point, I would spend $40 on a drink. When it comes to investing in yourself—putting money down on your LLC or hiring an assistant, many people second-guess those decisions. And rightly so, because it’s a risk. At the end of the day, you have to have faith in your hustle. It’s cliché, but you have to believe in yourself..

Even at my age, I don’t lose track of that. If you believe in yourself enough, other people will too. Often, we short-change ourselves for short-term excitement. Whatever you're looking at online or scrolling through on your phone—that’s not real life. You have to wake up, answer your emails, address phone calls, and get to work. That’s what you should focus on, not just posting things to feel great for the day. If you’re making money off social media, that’s a different conversation. But otherwise, keep that time to yourself to develop your hustles.

Don’t limit yourself to one hustle. Real estate is what people know me for, and I’ve marketed and branded myself as such. I am a real estate developer, but I’m also a businessman with several other ventures. I don’t need to tell everyone everything I have going on. The power is in the silence and the strategic moves you make.

We live in a resource-rich city, which we are not fully taking advantage of. When you start exploring your hustles and building that faith in yourself, 12 months can go by, and you’ve created a few small businesses. It might not bring in a million dollars immediately, but do the same thing the next year and the year after that. Over time, you build compound interest. I’ve been in the game for 15 years, and that experience compounds over time.

At the end of the day, like we were talking about earlier, you gotta start somewhere. We always talk about buying blocks and helping others do the same, but that's not where you start. You have to start somewhere. I'm a first-generation real estate developer, first-generation real estate investor, first-generation in a lot of things. My first purchase was a 311 square-foot studio in First Hill. That was the first piece of real estate I ever bought in 2006. It was all I could afford at the time.

Just getting started and taking that risk by putting that down payment down is crucial. You start to learn how to take care of what you purchase. I don't even like to use the term buying or purchasing. I prefer the term investing because everything I do involves money going out, and I look at it as an investment—unless I'm going to Vegas. But even then, I'm bringing people I really love and care about, so I'm investing in them, in myself, and in the environment.

Changing my lexicon a bit, I don't see it as buying or purchasing the block—I'm investing in the block. When you start to change your mindset and replace "purchase" or "buy" with "invest," you start treating that investment differently. You take care of it differently because you want to ensure that investment returns something. My goal is to make sure that everything we invest in as a company comes back in more ways than one.

Besa: Alright, so since we’ve been talking about investing, I like the idea of starting a business to invest in yourself because that’s what you’re doing. You’re investing in a block, in the community, but you’re also investing in your future. How can people invest in their future?


Jaebadiah: Investing in oneself happens in a number of ways, and there’s no right way to do it. I don’t have a game plan or a road map—there are no rules to this game, which is absolutely amazing. A couple of tips I would throw out there: 

Number one, we don’t talk about financial literacy, financial competency, or financial responsibility enough. You have to have your money right, and you don’t need a lot of money to have your money right. By that, I mean knowing how to budget. I lived off of $20,000 a year, but it’s about how you budget that $20,000. My dad had an amazing phrase called “Budget Balling.” Know what you can spend and know what you can keep. You don’t have to overextend yourself, and whatever you’re able to set aside for yourself, that’s what you use to invest in yourself. Pay your responsibilities and obligations, even if it’s tough. This country is hard; bills are hard, everything is expensive, but just make sure to put something down for your obligations to keep the train going.

I wouldn’t have been able to close on a $6 million loan for a piece of real estate if my credit score wasn’t right. That starts with paying small bills on time. Make sure your phone bills are paid. That’s an easy way to start. Secondly, don’t be afraid to take a risk on yourself. That’s the best bet you can ever place. Dream as far as you can and then put your own resources behind it. No one is going to put resources into your pocket until they see you doing it first. Invest in yourself, and that will prompt others to do the same.


We have a real estate fund, a small $10 million fund we kicked off a couple of years ago, and I’m learning a lot about how that structure works. One thing I’ve learned is that relationships are key. Make sure you align yourself with the right folks. Choose your audience. In my space of real estate and business, I make sure I’m with people who have resources and high intellect. Surround yourself with people you can learn from. You don’t want to be the biggest fish in the water when you show up to an event. You don’t want to be the smartest person; you want to walk into the room and feel like you don’t exist, so you have the opportunity to learn.


If you have an idea and you’re talking about it with your friends, at some point you’re going to have to do it. Make sure that whatever you tell yourself in the morning, find ways to practice it and engage with it. Surround yourself with people who will call you out and hold you accountable. Constructive criticism from people who love you is going to take you far. This journey is not easy. I might make it look easy, but at the end of the day, I have to believe in myself and put faith in my hustle. I’m telling you all to put faith in your hustle, and nothing will be able to stand in your way.

Besa: I love that. And real quick, let everybody know where they can grab your book.

Jaebadiah: Oh yeah, Believe In Yourself. I’m actually working on a zinger right now. I was very nice in Believe In Yourself. I’m not so nice in this new book. You can find Believe In Yourself on Amazon, Barnes & Noble, and any online retailer. Believe In Yourself is essential for the millennial entrepreneur; it's four years old now, which is kind of wild to think about. I think it’s about time, as a lot of work has been turned out, that the new book is going to be a little bit more robust for folks. 

A lot of the questions people are asking me, I’m going to go into crazy detail about. How did I start a fund? How did I get my first investor? How did I lock down a block on 23rd and Union? How did I buy 3 acres in Skyway? People don’t really know the details, right? There’s always a story behind the success, and that’s where the real gems are. That’s where people usually feel seen because they can resonate with your journey. 

Besa: Thank you so much for stopping by and chatting with us, and giving us some tips on how we can invest in ourselves and our community. Next time, you guys, we still have more coming up. Next, we have a room coming and we’re learning about something new.

Watch the interview

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