Lessons in Entrepreneurship

Many young people are interested in entrepreneurship but are not quite sure how to choose a problem to work on, what skills they need, or what tools to use. I’ve recently had the chance to interview Jesse Clain and Massi Genta, 2 entrepreneurs who started their careers fairly early. In this interview, they share their stories, their struggles, as well as their advice for those considering this path.

Interviewer: Can you briefly share your story?

Massi: Sure. My journey as an entrepreneur started pretty early. I consider myself a serial entrepreneur as I started 3 main companies. As a younger student, I shared the small projects I was working on. This is definitely my passion, I try to be a problem solver, it’s just the kind of thing that I enjoy doing, to work on projects and try to build things.

My first company was an influencer marketing company which allowed micro-influencers to monetize from their influence on social media. That experience taught me a lot: I learned how to talk to investors, how to manage a team, which was pretty difficult in the beginning.

After a few other experiences in private equity, I started another company in a completely different field and I got to work with researchers from the University of Texas at Arlington. We were licensing technology from the university, we were building hardware products, there was manufacturing involved. That was an opportunity for me to learn how to work with a hardware company, with researchers, how to deal with patents, with Proprietary IP. This was a sensor company founded to commercialize low-cost pH sensors. The sensors had various applications, from medical, agriculture, or cosmetics. With this company I also participated in a Global Startup Accelerator named ActnerLab and I moved to South Korea for a while to raise money.

My newer experience is with Clyste, which is an open-source tool. We created a governance system that allows users to monetize from the value they created on a social media platform.

Lastly, I created Metabob together with NEC.

Every company has given me a different perspective and shaped me as an entrepreneur.

I: What motivated you to become an entrepreneur initially?

Massi: I always wanted to become an entrepreneur. I’ve always wanted to be in control of my future and to have the ability to pursue my dreams and not rely on others for that. I always looked for ways to improve my life and to solve problems, to build projects and have fun building products. So it all started as a passion. As an entrepreneur, I’ve found it interesting to identify and overcome challenges.

I: What is the biggest thing you struggled with as an entrepreneur?

Massi: As an entrepreneur, there are many things you need to deal with: not just making sure the product is good, but there is the legal side, the HR, securing funding and others. I am not a very structured person and it was rather difficult to keep everything in order and to focus on all these different areas when all I wanted to do in the beginning was to build the product. Other areas may not be as fun but they are just as important.

I: Looking back, what is one thing you would do differently?

Massi: I think I would ask for help earlier, I would give up more equity in the beginning. As an entrepreneur, you don’t want to give up equity to anyone because you are the one building it.

If I were to go back, I would ask more people for mentorship. I did ask some people, but I am also pretty stubborn and I wasn’t listening much to what many people were suggesting.

Jesse: There were a lot of things I could have done better as a first-time founder. Without a doubt, my biggest mistake is the problem I chose to work on and my motivation for choosing that problem. I built my company purely around what I identified as a market opportunity. “Hey, here’s an opportunity to make money. Let’s do that.” That might work for some people, but it didn’t work for me. Money wasn’t a strong enough motivator for me — I wasn’t willing to go above and beyond for my company because we didn’t have a mission I considered worthwhile. So when I saw a chance to work on something that mattered to me, I took that chance and sold my company. If I could do it differently, I’d have built my company around a mission that mattered to me.

I: What is one thing you wish you understood about entrepreneurship before you got started?

Massi: I wish I knew what the role of a CEO in a company is after the first phase, when you identify a problem, validate it, and start building a solution for it and get some traction. After this phase, the CEO’s role includes many tasks such as securing the funding, managing the team, thinking about the direction the company is taking, all the legal aspects, talking to the Board. There is a lot more work than just building the product and I wasn’t aware of that in the very beginning. If I had known, I would have made fewer mistakes.

I: What do you consider to be your greatest achievement as an entrepreneur?

Jesse: What I’m most proud of is the work I did at Abaarso School in Somaliland. I started an entrepreneurship program with a class of 18. Everyone in my class made money and built value for the community. But my favorite part is that the spirit of entrepreneurship permeated the whole campus. After the last class of the week, I’d walk back to my dorm and 5 different kids, none of whom were in my entrepreneurship class, would try to sell me something. It was cool to see a market pop up out of nowhere. And I know the things these kids learned as entrepreneurs will help them build up their country over the next 20–30 years.

I: How have your entrepreneurial motivations changed since you first started?

Jesse: That’s easy. At first I cared about making money — or I thought I did. Now, for me, entrepreneurship is about making a positive impact in the world, not about capturing value. Next time I start an organization, it’ll probably be a non-profit.

I: If you could offer a first-time entrepreneur only one piece of advice, what would it be?

Massi: First-time entrepreneurs should be ready to work very hard and to master the skills they need for building something they are truly passionate about. Many people want to become entrepreneurs so they can be their own boss and to make their own schedule. In reality, if you need to make a living out of it, you need to be willing to work very hard. The world is full of talented entrepreneurs and if you want to compete with them you need to work more than everybody and to know everything about your product and your customers. Finding the right co-founder and making sure that the people you are hiring are irreplaceable and that they bring skills you don’t have is also important. It’s tough, but you need to put in the work.

Jesse: I’m gonna cheat and offer two answers.

The first: Only work on something you love. If you’re allowing yourself to take the risk of creating something new, allow yourself to create something you care about! Yes, life’s too short to work on something that doesn’t matter to you. Yes, you should be the change you want to see in the world. But also for professional reasons, you’ll almost always get a better result when you do something you love instead of something that you think other people might like.

The second: Starting something new is sometimes like being a stonecutter. You take 500 swings at the rock and you think nothing’s happened. You have no way of knowing that the 501st swing will finally cleave it in two. In the early days, you need to have some faith that if you’re doing something that makes sense, it will eventually work. Don’t give up when you have no idea how close you are to success.