Introduction and the Origins of Whayle
Taryell Simmons: Welcome, ladies and gentlemen, to another episode of Rise Urban Nation, the podcast where we share stories to help you unite, uplift, and ignite. Today I have special guests in the building as we dive into the mindset of entrepreneurship and wealth building with my brothers Shalimar Jackson and Leon Oloya. Shalimar is the co-founder of Whayle Mentality, and he brought his partner Leon with him today. Shalimar, Leon, it is an absolute pleasure to have you both on the show.
Shalimar Jackson: Thank you, Taryell. It is great to be here with you.
Taryell Simmons: Some of our audience knows that I went through RISE San Diego Cohort Three. Third time is always a charm, but what cohort did you come from, Shalimar?
Shalimar Jackson: I came out of Cohort Seven—the Magical Seven. We had to bring the magic back for the second time around.
Taryell Simmons: They brought the magic back! They might think they are the best, but that RISE family is deep. You told me earlier that RISE really helped you revamp this project. Leon, before we dive into the details of Whayle Mentality, share with us the background that led you both to venture into entrepreneurship together.
Leon Oloya: To Shalimar's point, he and I have been discussing entrepreneurial concepts for quite a while now. Shalimar has been part of a real estate investment group called SIG for several years. I historically came out of oil and gas corporate America with ExxonMobil—a Fortune 1 corporation at the time. Coming from that corporate structure is almost the opposite end of the spectrum from entrepreneurship, but there is plenty of gray space in between. Much of the success I had within ExxonMobil was driven by applying an entrepreneurial mindset within corporate initiatives.
Leon Oloya: When Shalimar and I sat down to think about what we could build next, we looked at what we were already doing in real estate and asked ourselves what we were truly good at. We realized we could master anything if we were willing to put in the hours. Both of us played Division 1 sports at New Mexico State coming out of San Diego, and we brought that athlete mindset to our professional careers. We did not want to just be average; we wanted to operate at an elite level. We did not just want to be the supervisor or the boss—we wanted to be a "whale" in our craft. That is how Whayle Mentality entered our vocabulary and became our core curriculum.
The Three E's of Whayle Mentality
Taryell Simmons: Break down that curriculum for us. What does having a Whayle Mentality actually mean in practice?
Leon Oloya: We live by the Three E's: education, experience, and engagement. First comes education. In order to become a whale in your craft, you have to build a foundational knowledge base. Once you have that education, you move into experience. Experience is the battle testing—putting ideas into practice, seeing what works, making adjustments, and learning from failure. Finally, once you have both education and experience, you must stay engaged. You stay locked in, consistent, and committed. That continuous cycle of education, experience, and engagement produces the excellence we pursue.
Shalimar Jackson: Exactly. Going through the RISE leadership cohort gave me tools that helped shape our perspective. We took those leadership insights, combined them with our athletic and corporate backgrounds, and adapted the program based on direct feedback from the community. We looked at what everyday entrepreneurs and young people were facing and asked how we could help each individual excel. Through our athletics and careers, we developed extensive relationships with agents, lawyers, accountants, tax experts, and real estate professionals. Whayle Mentality combines mental conditioning with tangible access to those professional networks.
Digital Access, Web3, and Building Community Equity
Taryell Simmons: You also incorporated digital assets into this model. Many people talk about NFTs and Web3 without understanding how to build real community value. How did you integrate digital access points into Whayle?
Leon Oloya: When we launched our digital access token, it was priced around 0.045 Ethereum. For us, it was never about telling people to buy a speculative asset and wait for the price to rise. Our focus was on creating a verifiable digital key that unlocks access to curriculum, mentorship, and educational resources. Everyone needs financial literacy and personal development, but an organization has to manage capacity. A digital membership provides an access point where community members also hold equity. If the community thrives and the resources grow in value, members participate in that upside. Even if someone only views it as a digital serial number, the knowledge and community they gain are well worth the investment.
Taryell Simmons: That reminds me of fractional ownership platforms like Masterworks, but you are bringing that model directly to our community for education and wealth building. Let us dial back for a second. When you talk about community, how do you define community, and why did you choose wealth building as your primary focus?
Leon Oloya: Community consists of the circles we inhabit on a regular basis—whether that is corporate offices, schools, athletic fields, or even correctional facilities. More broadly, community is anyone you have the ability to reach. Your messaging and delivery might shift depending on who you are speaking with, but the core principles apply across demographics. When it comes to wealth, we intentionally avoid defining wealth strictly as money. Currency and cash are obviously parts of wealth, but wealth is also time freedom, spending days with your family, peace of mind, and goodwill. Wealth is whatever utility you deeply desire. Our mission is helping people become a whale in whatever area of wealth matters most to them.
Navigating the School of Hard Knocks in Early Business
Taryell Simmons: Why did you choose the specific spelling W-H-A-Y-L-E?
Leon Oloya: We chose W-H-A-Y-L-E because we wanted to treat it as a proper noun representing a distinct mindset rather than just referring to the mammal. At the same time, we love the imagery of the whale—you see the whale tail in our logo preparing for a deep dive after taking in a massive breath of air. It symbolizes taking a breath, diving deep into your craft, and maximizing your value in your community.
Taryell Simmons: Starting any venture comes with challenges. What were some of the significant hurdles you faced early on, and how did you navigate through them?
Leon Oloya: Starting a company puts you directly into the school of hard knocks. Even foundational tasks like establishing an LLC across multiple states, opening business bank accounts, and coordinating legal documentation take weeks of effort. Beyond administrative tasks, creating artwork, building a website, and mastering social media marketing were areas where we were not initially experts. We had to apply our own Whayle Mentality to our learning curves. How do you build an audience of twenty thousand followers when your product is still in development? How do you navigate emerging digital spaces? We approached it like athletes: take the shot, see how the ball bounces, evaluate the outcome, make adjustments, and repeat the process. Each month we reviewed our progress, confirmed we were moving forward, and kept pushing.
Shalimar Jackson: You have to embrace the philosophy of being better today than you were yesterday. When you maintain that discipline, you do not quit prematurely before you uncover the diamond in your work.
Mentorship, Authentic Connection, and Lifelong Impact
Taryell Simmons: Looking back on your journey, what are the most important lessons you have learned about entrepreneurship and community uplift?
Leon Oloya: The journey reinforced principles we always believed in: hard work truly matters, and relationships are everything. Treating people with respect and genuine care pays dividends in ways you can never predict. You might show up to an informal lunch session with a simple brown-bag lunch, and that small gesture changes someone's entire trajectory. Two months down the road, people wonder why someone trusted you enough to make a major life change, but they did not see you taking that person out to a taco shop on a Saturday just to check in on them.
Leon Oloya: The hardest question we ever get asked is to explain Whayle Mentality in a neat sentence. But the people who experience it firsthand never struggle with that question. They understand it immediately because they received the support they needed. We get messages late on Saturday nights from individuals who cannot reach their sports coach, who feel overwhelmed, or who do not have a single family member able to help them understand a legal contract. These are fundamental life skills. When you meet people where they are, you witness immediate transformation. In athletics, it takes months in the gym before you see physical strength increase, but when you shift someone's mindset, you can see them perform better that very same afternoon.
Taryell Simmons: That connection is critical. When young men grow up without father figures or positive mentors, their world narrows. In my youth, I only had the streets, and I thought that circle was supporting me, but it was actually a cage. Those environments convince you that your dreams are foolish and you should just chase quick money. Men end up carrying that baggage into adulthood, never learning how to have vulnerable, honest conversations with other men because they fear being labeled weak. Society calls prisons correctional facilities, yet they completely sever individuals from community. We have to create authentic spaces where brothers can connect, learn, and heal.
Moving Forward and Connecting with Whayle
Taryell Simmons: This conversation has been powerful. Before we conclude, tell our listeners how they can connect with Whayle and access your upcoming initiatives.
Leon Oloya: You can visit our website at https://whayle.io to find our full schedule of events, programs, and partner resources. We collaborate with community partners, including RISE San Diego, to distribute opportunities across our network. Whether you are an athlete, entrepreneur, or community leader, our platform exists to help you reach that next level.
Taryell Simmons: Can I get an access pass too? Because I am definitely trying to win alongside you brothers!
Leon Oloya: Absolutely, Taryell. You already have access—you are locked in with us.
Taryell Simmons: You heard it here first! Listeners, make sure to check out the show notes and links to connect with Shalimar Jackson and Leon Oloya. Thank you both for sharing your wisdom and building such an impactful platform. Subscribe to Rise Urban Nation, share this episode, and stay tuned for our next inspiring guest. Peace!
