Trivelle Simpson

Welcome and Cultural Roots

Taryell Simmons: Welcome to another episode of Rise Urban Nation. Your host Taryell is in the building, and I have got Trivelle in the building. T and T, we are dynamite. We are going to make it happen. Tell the people where you are from.

Trivelle Simpson: I was born in Toronto, Canada, but both my parents are from Jamaica. I have been there more times than I can count. The food, the culture, the attitude, and the energy course through my veins. We were just having a conversation about food before we started recording.

Taryell Simmons: My mom just came from Jamaica with real jerk seasoning and Scotch bonnet pepper sauce. I made some jerk oxtail and jerk pork on the grill, and it was incredible.

Trivelle Simpson: Out in San Diego it is warm, so you can smoke jerk pork in a drum over the course of the day and get that hard crust. It is cold up here, so you are getting me excited.

Taryell Simmons: There is a large Caribbean population in Canada from Jamaica, Trinidad, and other islands. How did everyone migrate there?

Trivelle Simpson: It originates from the Commonwealth. People from Jamaica could easily move to England or Canada because they are Commonwealth countries. That is why we have massive celebrations like Caribana here in Toronto. It is deeply ingrained in the culture.

Taryell Simmons: When Toronto hip-hop emerged on the map, Drake really dominated the entire landscape.

Trivelle Simpson: Drake took over completely. I used to be involved in the local music scene, and there was an artist named John River who said that to be the best rapper in Toronto, you had to be the best rapper in the world because the best rapper in the world is from this city. It made it challenging for other talented artists because he commanded all the attention.

The Modern Renaissance Man and Career Beginnings

Taryell Simmons: For the people who do not know who Trivelle is, tell them who you are.

Trivelle Simpson: The simple answer is that I am the president and founder of The Drive Group, which is a venture and real estate development fund. We invest in small and startup businesses, accelerate companies, and develop real estate across North America with plans to scale globally. The deeper answer is that I am a renaissance man acquiring new skills. Growing up, I admired James Bond because he was capable of everything—speaking multiple languages, driving any vehicle, and always looking sharp. A renaissance man is someone highly capable in multiple domains, constantly striving to be better at everything.

Taryell Simmons: How does having such a wide, varied resume help you run a successful business?

Trivelle Simpson: The biggest lesson is cross-disciplinary skills. You learn something in one discipline, and it applies uniquely when you enter another field. I started in politics aiming to be a campaign manager. I majored in political science with a minor in economics and volunteered on a campaign. When our candidate lost, the candidate went back to practicing law, and I was left looking for work. I stayed in banking at Davis + Henderson doing check processing, and later worked at Manulife and Genworth, which taught me risk management and consumer appetite.

Commodities Trading and Tech Operations

Trivelle Simpson: After receiving poor investment advice from an advisor, I took complete control of my finances and taught myself how to trade derivative commodities, starting with my tax return.

Taryell Simmons: Break down what derivative trading actually means.

Trivelle Simpson: In standard stock trading, you buy shares of a company and profit when the price rises. A derivative is a leveraged financial contract that allows you to bet on price movements going either up or down. You use leverage to magnify the bet. If you predict a stock will rise by one dollar, a bank can settle a derivative contract paying out exponentially on that move. However, if the price drops by that dollar, you owe that same leveraged amount. You have to be fast, precise, and highly analytical. That is where I established my financial foundation.

Trivelle Simpson: From my derivative trading success, I was offered an opportunity to become head of operations for a tech company called Shell Service Capital. I spent four years leading operations, learning business management, contract negotiation, and execution in real time. My knowledge base was built on politics, banking, and trading, and I applied those skills to lead a team through daily business challenges.

Trivelle Simpson: Business is about putting out fires every single day. That is why having a renaissance mindset matters—I am never intimidated by what I do not know; I am energized to master it.

Economics, Politics, and Market Mindset

Taryell Simmons: You have an entrepreneurial career trajectory that spans multiple industries. How does your understanding of policy and government influence your approach to market volatility?

Trivelle Simpson: I understand trading because I understand politics, and politics is fundamentally the study of human behavior under scarce resources. If you have one hundred people and ten loaves of bread, politics is how you allocate those resources while keeping society moving forward. In markets, smart money anticipates policy moves. After years of monetary expansion, interest rate hikes are used to tame inflation. Raising rates intentionally creates economic pressure for the broader objective of stability. Life is a game where many participate without studying the underlying rules. Understanding how the system works allows you to position yourself strategically.

Fearlessness, Family, and Overcoming Adversity

Taryell Simmons: As a self-made entrepreneur, how does your perspective on risk and investing compare to individuals with inherited wealth?

Trivelle Simpson: I often reference the Bill Gates story. When he dropped out of Harvard to start Microsoft, his father was a prominent attorney and alumnus who could ensure he returned if needed. People often focus on the safety net, but the real takeaway is fearlessness. Elon Musk once said he would rather face extreme consequences than accept failure. Success demands total fearlessness regardless of your background.

Taryell Simmons: Many immigrant parents push for traditional careers like medicine, law, or engineering rather than entrepreneurship. How do we shift that mindset in our communities?

Trivelle Simpson: When I told my parents I was leaving my job to start a company—even though my mother is an entrepreneur running a salon—they both advised against it. During difficult stretches, they told me to get a stable job. They did not fully believe in the venture until they no longer had to work. Parents naturally desire the path of least resistance for their children because they want to protect them. However, greatness requires enduring great resistance. You need total self-belief and at least one trusted sounding board who reminds you of your mission when things get difficult.

Trivelle Simpson: In many communities, when a venture struggles, extended networks rally financial and professional support. In our community, founders often bear losses in isolation because collective backing is less common. We need to actively invest in and bet on our own entrepreneurs.

The Value of Intrapreneurship

Trivelle Simpson: Entrepreneurship is valuable, but intrapreneurship is equally powerful. An intrapreneur is someone who treats another person's company with total ownership and commitment without having put up the founding capital.

Trivelle Simpson: Steve Ballmer joined Microsoft as employee number thirty and managed operations diligently for decades. When Bill Gates stepped down, Ballmer became CEO and generated immense wealth through sheer commitment. Similarly, Susan Wojcicki rented her garage to Google's founders, joined as an early employee, spearheaded the acquisition and growth of YouTube, and served as its CEO. We need more individuals willing to commit to long-term operational excellence, because dedication produces compounding results.

Work-Life Flow and Leadership Sacrifices

Taryell Simmons: What are your thoughts on work-life balance for entrepreneurs?

Trivelle Simpson: To me, traditional balance does not exist when you are building something extraordinary. In his documentary Muse, Kobe Bryant spoke about sacrificing personal comfort to achieve basketball greatness. You must be obsessed with your vision because what is built lasts longer than what is born. If you believe in paying your dues and putting in the ten thousand hours, you should want to invest those hours as aggressively as possible.

Taryell Simmons: I view it as work-life flow and integration. You stay locked into your ultimate mission while integrating your personal life and partnerships into that journey.

Trivelle Simpson: Exactly. If your partner is aligned with the vision and willing to make shared sacrifices, it empowers the mission. Behind every successful leader is a strong partner who supports the journey.

Taryell Simmons: Do you miss anything about being a traditional employee?

Trivelle Simpson: I miss the ability to completely unplug at the end of the day. As a founder, my phone is always on, and leadership responsibilities are constant.

Taryell Simmons: What tools or resources are indispensable for your daily workflow?

Trivelle Simpson: My phone is essential, particularly market news applications like CNBC. Real-time information builds confidence, and confidence drives effective business execution.

Taryell Simmons: What has been the toughest leadership challenge you have faced?

Trivelle Simpson: Having to say no to close friends and executive partners during difficult financial quarters. When an executive requested an advance during a tight cash-flow period, I had to prioritize fiscal responsibility over personal sentiment. As a leader, you must make hard choices for the long-term health of the organization.

Founding The Drive Group and Accumulating Favor

Taryell Simmons: How did you create The Drive Group?

Trivelle Simpson: I envisioned a collective think tank of ambitious individuals driven to tackle complex business challenges. When prospective partners were not ready to commit financially, I kept the vision alive individually. We began by refining trading strategies and transitioned into small business and real estate investments under the banner of being relentlessly driven.

Taryell Simmons: What advice do you give on turning ideas into profitable ventures?

Trivelle Simpson: When starting out, do not focus solely on raising capital; focus on accumulating favor. Provide excess value, barter services, and help partners achieve their goals. Financial capital is finite, but goodwill and relational favor are boundless. When people trust your character and work ethic, high-value opportunities and funding follow naturally.

Starting Over and Building Resilience

Taryell Simmons: What was your first job, and how did early struggle shape your work ethic?

Trivelle Simpson: My first job was working as a receptionist at my mother's hair salon. My second job was packing juice containers in a manufacturing warehouse and moving heavy pallets. Later in life, after launching my first business venture, I depleted my funds and had to return to a lower-paying temp job to settle debts. A close friend told me, "I told you so." That setback fueled my determination. I worked diligently, paid off my liabilities, and rebuilt my business stronger than before.

Trivelle Simpson: My greatest asset is high social intelligence. Knowing how to respect people, show genuine appreciation, and cultivate strong relationships has driven my success across every venture.

Advice for Aspiring Entrepreneurs and Market Outlook

Taryell Simmons: What advice would you give to someone looking to enter trading, venture capital, or real estate?

Trivelle Simpson: First, develop a healthy obsession with your chosen field. When market conditions or circumstances make no logical sense, your passion is what keeps you moving forward. Second, be adaptable. What an industry produces may differ from your initial expectations, so remain open to unexpected opportunities while controlling what you can.

Trivelle Simpson: Looking ahead across our three sectors: in trading, algorithmic systems and retail participation will increase market velocity and volatility. In real estate, tightening credit and price adjustments will create opportunities for disciplined buyers with strong credit. In venture capital, economic downturns weed out poorly run businesses, allowing agile founders to acquire elite talent and build resilient enterprises.

Current Projects and Where to Connect

Taryell Simmons: What projects are you currently working on, and where can people connect with you?

Trivelle Simpson: We are running our Drive 250 initiative through our website, offering up to two hundred and fifty thousand dollars in venture investment for high-potential startup founders. Applications are open through April. You can learn more at https://www.thedrivegroup.ca and follow our team on Instagram at thedrivegroupinc.

Taryell Simmons: Thank you for sharing your journey and dropping so much value today.

Trivelle Simpson: Thank you for having me. Much love and blessings.