We caught up with the brilliant and insightful Caleb Thompson a few weeks ago and have shared our conversation below.

Caleb, appreciate you joining us today. Alright, so one thing we think people don’t talk about nearly enough is investments – either time or money. What’s one of the best or worst investments you’ve made and what did you learned from the experience?

The greatest investment I have ever made is in myself—specifically in my personal development. I have dedicated years to building emotional intelligence, mastering core areas of business such as marketing, sales, and finance, and cultivating the discipline needed to consistently create value. Equally important, I’ve learned to develop resilience from failures, refusing to let setbacks define or deter me.

Coming from a family of 14 and growing up in poverty, I often asked myself why no one in my family had ever pursued the creation of generational wealth. That question sparked a mindset shift: “Why not me?” I chose to be the one who breaks the cycle, who invests in growth, and who builds not only for myself but also for the generations to come.

Caleb, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

My name is Caleb L. Thompson, and I like to describe myself as a serial entrepreneur, creative visionary, and builder of opportunities. I grew up in a family of 14 children, bathed in poverty, but with a burning realization early on that I could be the one to shift the narrative—someone who could create generational wealth and open doors where none existed before. That belief, along with years of resilience, discipline, and a commitment to personal development in emotional intelligence, business, and leadership, shaped my journey.

I’ve built a diverse portfolio of businesses because I don’t see entrepreneurship as a single lane—I see it as a way to transform communities, empower families, and create value in multiple industries. My ventures include:

Food & Hospitality: Thompson Square Gardens Restaurant Company, known for gourmet catering, corporate meal plans, and unique dining experiences. We solve the problem of “boring food service” by bringing creativity, health, and memorable flavors to both everyday meals and large-scale contracts.

Retail, Lifestyle & Fitness: Thompson Shoe & Clothing Unit, Inc., Thompson Square Gardens Emporium, Paradise Gardens Home & Garden Co., and Gotham Fitness Supply Co. These ventures bring culture, convenience, wellness, and style to communities, serving families with everything from clothing and footwear to home and garden essentials to elite-level fitness equipment.

Coffee & Culture: Thompson Square Gardens Coffee Company, where I merge international coffee flavors, gourmet food, and youth-focused bookshop spaces—creating gathering places that blend culture, conversation, and commerce.

Real Estate & Investment: Paradise Gardens International Realty Co. and TSG Global Resource Management Group. Here, I not only invest in properties and businesses but also provide guaranteed returns and consulting that helps others grow sustainable streams of income.

Creative & Branding: Thompson Heritage Branding Co. (photography and creative services) and Coeur Ardent (an elite art studio/gallery for artists and fashion). These companies give me a space to highlight creativity, storytelling, and brand elevation for businesses and individuals.

Education & Mentorship: Manhattan Entrepreneur Academy, where I’m building out complete courses like Cultivating a Business Mindset—empowering the next generation of entrepreneurs with the tools, knowledge, and mindset to build something lasting.

What sets me apart is not just the variety of industries I work in but the heart and intentionality behind every venture. Every business I build is rooted in community impact—whether that’s providing jobs, giving young people spaces to dream and work, supporting veterans through relief programs, or offering financial literacy and entrepreneurial guidance to those who never thought they had a chance.

I’m most proud of the fact that I’ve taken what many would see as disadvantages—poverty, a large family, limited resources—and used them as the foundation for resilience, creativity, and vision. My journey proves that failure is never final and that discipline and persistence can carve pathways where none seem to exist.

For potential clients, followers, and supporters, I want you to know this: I don’t just build businesses—I build ecosystems. My work is about legacy, about creating opportunities that extend far beyond myself, and about helping others see that they too can step into ownership, creativity, and impact.

At the core of it all, my brand and my life’s work are about turning vision into reality and helping others do the same.

Have you ever had to pivot?

When I first launched my very first business, Thompson Square Gardens Restaurant Company, in my hometown in Oklahoma, I believed the people who knew me best would celebrate this step forward. Instead, I quickly discovered the harsh reality of the “crabs in the bucket” mentality. What should have been a season of growth and encouragement became a season of opposition.

My business faced countless sabotage—not just from competitors, but from people I had known my whole life. Family, former friends, and others from my past resented the fact that I wanted to break out of the cycles of poverty, toxicity, and purposelessness that had gripped our community for generations. They felt I had betrayed them by choosing a different path, and instead of cheering me on, they found ways to tear me down. Doors to new clients were deliberately closed, opportunities were blocked, and attacks came both physically and spiritually.

It became clear that if I stayed in that environment, I would either be crushed under the weight of small-mindedness or dragged back into the very cycles I was determined to escape. So I made one of the most difficult yet pivotal decisions of my life: I walked away.

I left everything behind and moved to New York City with nothing but a set of clothes and a few snacks. Entering the homeless system was humbling, but it was also the reset I needed. Stripped down to nothing, I was forced to focus, rebuild, and lean completely on the grace, mercy, and empowering power of God through the Holy Spirit.

That pivot turned out to be the best decision I ever made. What many thought would break me became the very foundation of my testimony. In just eight months of starting over, I went from being sabotaged in my first business to owning and operating 32 companies.

That experience taught me that what looks like a setback can actually be a divine setup. It proved that resilience, discipline, and faith can turn any trial into triumph. Today, every venture I lead is about more than profit—it’s about purpose, community impact, and legacy.

How did you build your audience on social media?

When people ask me how I built my audience on social media, my answer is simple: Authenticity.

I didn’t try to adopt a personality, mimic my role models, or play into trends just to get attention. Instead, I did something a lot of people skip over—I sat with myself. I asked hard questions: Who am I really? What are my core values? What do I like? What do I truly want out of life? What is my purpose? And most importantly, I spent time with God to align my life with His plan.

After that time of reflection, I made myself a promise: I would always show up as me—even if no one understood me, liked me, or agreed with me. I realized the essence I carry is one that terrifies societal norms and refuses to be controlled. That essence is authenticity, and that’s exactly what drew people to me.

See, people aren’t looking for another copy of someone else—they’re looking for someone real. And when you choose to walk in your truth, your light, and your God-given identity, you attract the right people who are meant to connect with your journey.

My advice for anyone just starting out: don’t build a brand around who you think people want you to be—build it around who you really are. Spend time getting to know yourself. Spend time with God. Once you understand your values, your voice, and your purpose, your presence—online and offline—will have an authenticity that people can’t ignore.

That’s how I built my audience. Not by following, but by leading with who I truly am.

Contact Info:

• Website: www.thompsonsquaregardenscoffeecompany.bigcartel.com
• Instagram: https://www.instagram.com/ceo_caleb_thompson?igsh=MWphaDBkNHRvMmRneA==
• Facebook: https://www.facebook.com/share/17E3hU6v9N/
• Linkedin: https://www.linkedin.com/in/caleb-l-thompson-3080b120b?utm_source=share&utm_campaign=share_via&utm_content=profile&utm_medium=android_app
• Youtube: https://youtube.com/@houseofbusinesspodcast2.0?si=4eatmUD5pwCeKKge
• Other: •Words Of Edification With Caleb(YouTube): https://youtube.com/@wordsofedificationwithcaleb?si=MXaGn2zwFx9NZtoM

  •The Morning Roasted Podcast(Dailymotion): https://www.dailymotion.com/user/themorningroastedpodcast