An Interview with Roger Underwood

When Roger and I started the interview, he was relaxed, wearing sweatpants and a sweatshirt, listening to a podcast discussing business. He took his headset off and we began with introductory questions meant to make him feel as relaxed as possible. As we began, he was taken back believing we had already started getting into the Q&A session. 

Pamela: How long have you been interested in business?

Roger: Since I was 12. You don’t understand it that way, you just want to get money in your pocket. At school selling candy and being conscious of it. We didn’t look for business classes, but we were concerned with getting caught with the candy and maybe getting suspended.

Pamela: You went to primary school in the late 80’s and 90’s, academics were focused differently. Did you feel business ownership was encouraged within the academic setting?

Roger: No, you were trained to get a job as opposed to working for yourself. Even within the trades, certain things were not broken down for you, about what you can make. I think I learned a lot on my own. I don’t remember being walked through the process- entry level, journeyman level, master level and owning a company. Taking a course for 4 years, you should be an apprentice and exit a journeyman, knowing how to do estimates.

Pamela: Tell me about your experience in a startup.

Roger: Startups are going to be rough. There are a lot of decisions to be made and you have to be confident in making decisions. It’s tough to do with a lot of partners and the mixture as far as where people are in their lives. It offers good and bad experiences. There are a lot of influences, but we have to make sure everyone is okay with this one thing and sometimes that is hard to do.

Pamela: Any regrets? A learning curve not expected?

Roger: The approach with how things got started was flawed. Operationally, we now know there is a better way. The brainstorming, a singular vision being on the table and we have to dissect it. Everyone believes, everyone also thinks another way can be better. It turns into too many voices, and you can end up where you started because it takes so long to get things accomplished. 

Pamela: Why would you feel we haven’t accomplished enough? 

Roger: Because we didn’t for as much as we know about business. 

Pamela: What did you hope to have accomplished by now?

Roger: The company could have been an overnight success.

Pamela: Where were you looking to be?

Roger: We should have multiple properties by now. We should be on our fourth clothing line season. Everything we are trying to do we could have had in place and done already. It takes two weeks to get a real meeting for decision making and voting. Those things can lengthen the time to achieve. When we have multiple members making financial contributions you are not able to do what you want with other people’s money and that can play a part in making progress.

Pamela: How did EVOS become a multi member LLC?

Roger: There was an understanding we were going to take everyone rather financially or creatively. One thing that’s different is it’s tiered. If everyone had the same equity, it’s possible everyone would be different. We are all family, so it made sense we do this together. 

Pamela: Do you consider yourself a venture capitalist?

Roger: Sort of, as it’s not always your own vision to be successful. If you have the opportunity to invest in something you like, you see the importance, so I am a venture capitalist, technically.

Pamela: Do you feel successful in the startup realm?

Roger: I always feel successful. Is the business actually successful, meaning is it making a lot of money today? No, because we need to constantly have stuff to offer to make a lot of money.

Pamela: Is EVOS headed towards always having things to offer?

Roger: Yes, I believe so.

Pamela: What’s the most important decision to get you where you are today?

Roger: Learning how to trust God. Things may not look the way you want, but not allowing that to get you down. Continue to do what you have to do and trust God to make a way.

Pamela: How many startups have you been involved in?

Roger: Technically, 1. This is the first one I put more effort into with no regrets.

Pamela: What would you do differently?

Roger: Nothing.

Pamela: Where do you see the business in 5 years? The business has not had the most robust start, tell me about the business in 5 years. There’s a lot of industries and it seems to be an exciting time to be a member of EVOS.

Roger: I will say this, without us willing to put a personal guarantee on some things we will not be able to get everything done as quickly as we would like. I’m not putting a limit on it, but in 5 years, at least if we are discussing Pittsburgh, we should be household names. We should be generating a significant amount of money, our properties should be worth at least $1 million dollars and our hospitality and media should be producing a lot of resources as well.

Pamela: How do you want to be known?

Roger: I want to be defined as a devoted family man who did the best he could do to uplift his family, community and people.

Pamela: Are you living the life you wanted?

Roger: Depends, right now I’m living the life I want, taking care of family and making progress towards the life I would like to have.

Pamela: Can you describe your worst decision and your recovery?

Roger: Not valuing everything life offers during my younger years. Not making the best decisions to keep dreams alive. My recovery is focused on trusting God. That has made the difference, today.

Pamela: That was such a great way to end an interview, by understanding God has made the difference. Thank you for your time today, Roger. Your interview provided a lot of great information and insight into the direction EVOS is going and the slogan “a company on the move” is fitting. As a fellow Founder (and Roger’s wife), I am so excited to take this journey. We have many things coming, and your experience will be appreciated in the process.

Roger: Thank you.

This concluded the first interview of the Founder’s Corner series with the current Vice President, Roger Underwood, of EVOS Investment Company. While Roger gave enough information, I enjoyed the process of gaining perspective about what he wanted to do and why. These interviews have offered great moments of the who, why and direction. Please check back for additional interviews to be held, including with the current President, Anthony McBride and the youngest founder, King Underwood.