How Demi Oloyede’s Early Ventures Shaped the Vision Behind Leansite

Demi Oloyede has been building businesses since childhood.

Today, she leads optimization platform Leansite—but her entrepreneurial streak started with a delivery service, a cleaning company, and an on-campus resale hustle in college. Spotting opportunities and filling gaps are her superpowers.

Here’s how those instincts inspired her to become Leansite’s founder.

Did you always know that you wanted to be an entrepreneur?

Yes! I started my first business at eleven years old. As the youngest of twelve siblings, I was constantly sent on errands, and since I had a bike, I was the default delivery service. One day, I noticed something interesting: whenever I returned from an errand, there was always change left from the original payment. It occurred to me that if there was leftover money, they could afford to pay me, so I started charging by destination. I was a logistics company of one! When I moved to the U.S., I kept the same energy, building a small cleaning company from scratch. I also sold Amazon return goods to students using Facebook Marketplace and other platforms. 

I've always looked at inefficiencies and found the margin. The only thing that held me back was access. Immigration and citizenship limited what I could legally do and how far I could scale. The moment that was resolved, I went all in. 

What have you learned about building a team and a support network around yourself?

Clarity and accountability are non-negotiable. Early on, I made the mistake of tolerating underperformance for too long, thinking I could coach through it or that potential mattered more than execution. It doesn't. When someone consistently misses the bar, keeping them on the team hurts everyone. The rest of the team picks up slack, standards erode, and momentum stalls. 

I've also learned that culture isn't what you say, but what you tolerate. I had to let go of team members who were technically capable but created dysfunction because of their unprofessionalism or unrealistic demands. Protecting the culture means making hard calls quickly. 

On the flip side, I've learned to hire for operational excellence and judgment, not just credentials. My COO, for example, has been transformational—not because he has the fanciest resume, but because he executes with precision and thinks like an owner. The best team members are the ones who see what needs to happen and make it happen without needing their hand held. 

In terms of support networks, other founders are invaluable—not for advice, but for perspective. They understand the specific loneliness of being responsible for payroll, difficult personnel decisions, and existential pivots in ways that advisors and investors just don't. Finding your founder peer group is as important as finding investors. 

The biggest lesson? Hire slow, fire fast. I got the second part right eventually, but I'm still learning to be more patient and rigorous on the front end.

Have you ever felt like you're "different"? If yes, in what ways has this contributed to your journey as an entrepreneur?

I've always felt different. I grew up in Nigeria as the youngest of twelve children, moved across countries, then came to the U.S. as an immigrant with very limited resources. I learned early how to adapt to new environments, new expectations, and new systems. I was constantly observing how things worked, who held power, and where inefficiencies existed. Being different meant I didn't fully fit into any one box. I wasn't just technical, but I wasn't just operational. I wasn't just mission-driven, but I wasn't purely profit-driven, either. I saw systems from both the inside and outside. That outsider perspective became an advantage. 

When you've had to decode environments your whole life, you get good at pattern recognition. You see structural gaps. You question assumptions other people take for granted. You're less afraid to challenge the way things have always been done. Entrepreneurship rewards that. It also builds resilience. Immigration challenges, resource constraints, and navigating spaces where you're underrepresented forces you to build emotional stamina, which is critical when you're raising capital, managing teams, or pushing through uncertainty. 

What's the biggest misconception others have around entrepreneurship?

That it's all about the idea. People romanticize the "aha moment" or the single brilliant insight, but entrepreneurship is almost entirely about execution. I've met dozens of people with versions of what my company does. The idea itself isn't unique. What's rare is the willingness to do the unglamorous work: cold calling property managers, debugging vendor payment flows at midnight, personally onboarding every early customer to understand their workflows. 

The second misconception is that you need permission or perfect conditions to start. I see people waiting for funding, waiting for the right co-founder, waiting to quit their job, waiting until the product is perfect. You don't need venture capital to validate your idea; you need customers willing to pay you money. 

Thirdly, people think that entrepreneurship is about freedom. It's actually about accountability. You're accountable to your team, your customers, your investors, and yourself in ways that employment never demands. There's no one to blame and no structure to hide behind.

What would you tell your younger self if you were to start your entrepreneurial journey all over again?

Start sooner and stop waiting for permission. I spent years building skills at other companies, learning product management, understanding enterprise sales, and studying how great companies operate. All of that was valuable, but I also used it as a safety net. I told myself I needed more experience, more credibility, and more preparation before I could build my own thing, but I was ready earlier than I thought. 

Trust your instincts about people faster. I've wasted time trying to coach people into roles they weren't suited for or tolerating behavior that I knew was wrong because I second-guessed myself. 

The chip on your shoulder is fuel, but don't let it become a cage. Being an immigrant, being a woman in tech, being a Black founder—all of that drives me to prove people wrong. But I'd remind myself that the goal isn't just to prove doubters wrong; it's to build something that matters. The best revenge is building a great company, not just surviving to spite the odds. 

Oh, and one more thing: buy Bitcoin in 2013.