Entrepreneurship often starts with optimism. What sustains it is something deeper.
In this video, Kent Waltman, Chief Administrative Officer and Will Trepp, Co-Founder and COO of Rockport, share reflections on the advice they would give new entrepreneurs after years of building a business. They talk about why money alone is rarely enough motivation, and why understanding your personal reasons for starting a company matters from the beginning.
Will and Kent also discuss what it means to truly own the problem as a founder. They reflect on learning to rely on others, trusting people with different strengths, and carrying responsibility even when outcomes are uncertain. The conversation highlights how experience changes the way entrepreneurs think about risk, leadership, and commitment over time.
Watch to hear their advice on what it really takes to start and sustain a business.
Visit the Rockport Studio to hear more perspectives on entrepreneurship, leadership, and long-term thinking:
https://www.therockportgroup.com/resources/rockport-videos
If you want to start a business, there must be reasons to do it in addition to monetary reasons. I find that entrepreneurs, by definition, tend to be wildly over-optimistic. They always underestimate how hard a problem is. But it's almost a positive attribute. Because if you realize how hard it would be, you wouldn't have started. You would never embark on the journey. If you knew how challenging it was going to be, you would never embark on the journey. And so being an optimist, I think you're exactly right, gets you started.
It's what enables you to get started. The best entrepreneurs own the problem, but they're also able to work with other people. They're able to work with a team of people. I always had to hire people smarter than myself who can solve those problems, and you must allow them to contribute, right? It's beneficial for them. It's rewarding. Include them in the process of solving those problems, but it's still your problem at the end of the day, and you've got to make sure that it gets solved.
There's no question that starting businesses can be financially rewarding but there must be more in it. You must have an interest in the domain, the subject matter. You must be driven by a vision of making an impact in a certain market niche or disrupting a certain process, and that must excite you. There must be another motivating factor other than financial. It must be that you almost need to do it. You know, you're seeing something that's bothering you, and you say, I know how to do it, I know how to fix it.
And the pursuit of that need, that urgency, that inspiration, then will ultimately lead to great outcomes. But as you say, you can't get in it to make money. So that would be my advice is just count the cost before you jump in and be honest with yourself. You shouldn't lie to anyone, but the worst lies you tell are the ones you tell yourself. And so, make sure you understand your own personal motivation and can articulate it understand it and that it seems conducive to the very difficult process and challenging process of getting a business off the ground.