Dre Steinberg of Harlem on Life, Lessons & Legacy

We recently had the chance to connect with Dre Steinberg and have shared our conversation below.

Hi Dre, thank you so much for taking time out of your busy day to share your story, experiences and insights with our readers. Let’s jump right in with an interesting one: What do the first 90 minutes of your day look like?
I like to kick things off by giving thanks and making my bed, it’s a simple win that sets the tone. From there, I’ll check in on the stock market, review my calendar, and map out the day. Then it’s gym time for about 30–40 minutes to get my energy right. Once I’m back, showered, and ready, I usually jump straight into a call, a webinar, a project, or scheduling content. Those first 90 minutes are all about setting the rhythm for everything that follows.

Can you briefly introduce yourself and share what makes you or your brand unique?
Of course, I’m Dre Steinberg, Founder and Creative Director of Designed to Conquer, a creative tech company here in Harlem. We help entrepreneurs and service-based businesses level up their online presence with clean, powerful websites, strong branding, and digital tools that actually move the needle.

What makes Designed to Conquer special is the story behind it. I started the company during the pandemic, after losing my job, and the phrase “I am designed to conquer” became my lifeline. It’s now the heartbeat of the business. Today, we’re not just building websites; we’re building confidence and growth paths for entrepreneurs. Outside of client work, I also run The Check In, a men’s mental health group, and No Gatekeeping, a storytelling platform for entrepreneurs. Right now, I’m excited about expanding all three arenas of our work, design, education, and community impact.

Appreciate your sharing that. Let’s talk about your life, growing up and some of topics and learnings around that. What breaks the bonds between people—and what restores them?
I think bonds break when people stop listening and start assuming. Miscommunication, ego, and a lack of vulnerability create distance. But bonds can always be restored when there’s honesty, empathy, and a willingness to meet each other where they are. For me, restoration often starts with a simple conversation where both people feel seen and heard.

What’s something you changed your mind about after failing hard?
For a long time, I thought I had to do everything myself to prove I was capable. That mindset led straight to burnout and missed opportunities. After falling flat a few times, I learned the power of collaboration! Bringing others in doesn’t take away or weaken your vision, it expands and strengthens it. I realized collaboration is the real power play. Failure taught me that success is never a solo project.

I think our readers would appreciate hearing more about your values and what you think matters in life and career, etc. So our next question is along those lines. Is the public version of you the real you?
Yes, but with context. I try to show up as my full self, with creativity, lifestyle, and perspective, because being a creative doesn’t always fit neatly into “corporate professional.” I’m professional nonetheless, but I’m also intentional about showing the layers of who I am. Tech and design aren’t always seen as the sexiest fields; they can feel stale or overly technical. That’s why I make it a point to bring energy and personality into the way I show up. I like people to understand that being a creative has its own rhythm. The public version of me is the real me.

Thank you so much for all of your openness so far. Maybe we can close with a future oriented question. Could you give everything your best, even if no one ever praised you for it?
Hell yea, the real reward is knowing I put the time and energy into a project I ENJOYED. Praise is great, but it’s not the fuel. I’ve learned that in business and in life, external validation comes and goes. What sticks is the discipline of giving your best, even when no one’s clapping. That’s how you build consistency, character, and results. When the recognition eventually comes, it feels good but the work has already spoken for itself.

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