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Conversations with Abraham Robertson

Today we’d like to introduce you to Abraham Robertson

Hi Abraham, it’s an honor to have you on the platform. Thanks for taking the time to share your story with us – to start maybe you can share some of your backstory with our readers?
I’ve always been drawn to entrepreneurship, even before I fully understood what the word meant. Growing up in Jamaica, I discovered my knack for finding opportunities early on. In high school, I started throwing events, and my first one drew over a thousand people in Kingston when I was just 15. I’ll never forget the look on my mother’s face when she saw how much money I made at the gate that night.

That spirit led me to Howard University on a full athletic scholarship, where I studied Banking and Finance. There, I refined my knack for valuation—learning how to assess companies’ true worth, whether listed publicly or trading privately. Pairing classroom theory with self-taught technical analysis, I grew $15,000 (a combination of $10,000 my mother gave me for four years of college and $5,000 from my events) to $60,000 by graduation.

While many of my peers headed to Wall Street, I saw potential in striking out on my own. It wasn’t long until a friend invited me to invest in a real estate project, leading to the purchase of a $45,000 parcel of land that was eventually developed and sold for a $100,000 profit. That early deal propelled a series of residential and commercial ventures in Atlanta and Baltimore, attracting upwards of $1 million in outside capital from fellow Howard alumni and other investors.

Despite these U.S.-based pursuits, I also remained committed to opportunities in my home country. I have taken stakes in Jamaican agriculture ventures and plan to broaden investments across other industries on the island, leveraging a network of local partners. Now overseeing both private capital allocations and my own personal portfolio of businesses, I continue to balance a growing real estate pipeline with strategic equity positions—an entrepreneurial path that began with a single event in Kingston and has expanded into a multifaceted investment enterprise.

I’m sure it wasn’t obstacle-free, but would you say the journey has been fairly smooth so far?
I’ve also faced my share of challenges along this journey. One of the biggest has been the sense of isolation that can arise when you choose entrepreneurship over a more traditional path. Early on, it felt like I was moving in a completely different direction than everyone around me, most of whom were headed into corporate roles. At the time, entrepreneurship wasn’t nearly as mainstream as it is now, so finding peers and mentors to exchange ideas and strategies was difficult.

This experience ultimately led me to start a community dedicated to helping aspiring entrepreneurs and investors. I wanted to create a space where people could learn from shared experiences and avoid common pitfalls. That support system can make all the difference, especially when it comes to grappling with failure. Sometimes an idea doesn’t find its moment in the market, or the timing simply isn’t right. It took me a while to accept that reality, but I’ve learned to pivot more quickly and move on to the next project. Embracing that process has not only helped me grow personally but also shaped my approach to every new opportunity.

Alright, so let’s switch gears a bit and talk business. What should we know about your work?
I’m primarily an investor and entrepreneur, with a focus on real estate development and private equity in small-to-mid-sized businesses. While real estate projects in cities like Atlanta and Baltimore form a major part of my work, I’m also committed to investing in my home country of Jamaica—particularly in agriculture and other emerging sectors.

What I’m most proud of is creating a community that helps new entrepreneurs and investors learn the ropes and avoid common pitfalls. Early in my career, I often felt isolated—many of my peers were heading into corporate roles while I was forging my own path. That experience inspired me to offer resources, mentorship, and support to people who want to explore entrepreneurship or invest their capital wisely.

I believe what sets me apart is my willingness to combine traditional financial methods—like valuation and market research—with a hands-on, almost grassroots approach. I’ve learned from real-world experience since I was a teenager, throwing events in Jamaica and then translating that drive into ventures abroad. Whether I’m investing in real estate, small businesses, or agriculture, I focus on building genuine partnerships and growing together with the people I work with. That collaborative spirit, paired with a track record of scaling projects across multiple markets, shapes who I am and how I operate.

We’d be interested to hear your thoughts on luck and what role, if any, you feel it’s played for you?
Luck has definitely played a significant role in my life and business. I’ve been blessed in ways I can’t always explain, and from a young age, my parents told me I had a “golden thumb.” Over time, I started to see exactly what they meant: I often find myself in the right place, at the right time, with the right people around me. Beyond that, I’ve always had this deep-seated feeling that good fortune would come my way and, more often than not, it does.

That said, luck only takes you so far. You still need the skills, knowledge, and resources to act on the opportunities that appear. I’ve spent years learning how to manage finances, analyze markets, and build networks, so when those lucky moments happen, I’m ready to capitalize on them. It’s that combination of faith, preparation, and the willingness to seize the moment that has shaped my journey.

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