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Otis D. Gibson of GERTRUDE: 5 Things I Wish Someone Told Me Before I Became a Founder

Dec. 2025 - Authority Magazine

Thank you so much for joining us in this interview series! Can you tell us a story about what brought you to this specific career path?

I stumbled into this business at 19 years-old the old-fashioned way: one of my good friend’s dad worked at an agency. I grew up in New York and was working at clubs. I wasn’t sure what I was going to do after college. A friend’s dad worked in an agency and said, “Hey, you should look at our internship program. I think you’d really love it.” I got a job in a design studio and that started my journey in this business. It turns out that I really did love it, understood it, and was good at it. And I’m still just as passionate about it as I was when I first got in. So I’m very lucky that way.

Can you tell us a story about the hard times that you faced when you first started your journey?

I haven’t faced many hard times. I was given some amazing opportunities to work on some incredibly large brands with some tremendous mentors around me, so I just went for it. The door was open for me and I took advantage of it. I had people that cheered me on and wanted me to win. I guess I faced every young creative’s hard time: I was generally pissed that I couldn’t do what I wanted to do when I was 21 years-old because I didn’t know enough at that time. But I thought I had it figured out and could run the agency at that point.

Where did you get the drive to continue even though things were so hard?

It wasn’t a bad struggle in New York in the early 90s. The economy was good. I had a great apartment. I was getting paid well and I was making ads. So, not a big struggle.

So, how are things going today? How did grit and resilience lead to your eventual success?

Being a person of color in this business is challenging. I spent the first number of years in this business, being one of the only two or one of the only three in very tall buildings. I don’t have a chip on my shoulder about it, but I was very cognizant and aware. If you live in America and if you’re brown, you understand that you need to work a little harder and be a little smarter. Doesn’t mean you’ve necessarily had it hard. By being aware, you can walk through a lot of minefields. I didn’t have anyone trying to keep me down. But I wasn’t going to let that happen anyway because I was conscious that that could happen and I was never going to put myself in a position where I felt trapped. But that also might have ultimately led me to becoming an entrepreneur. At my first job, I thought “I don’t know what this place does, but it feels great and I’m going to own my own shop one day,” without even fully understanding the mechanics of it. From day zero, I never planned on keeping a job. I don’t know that I’ve ever had a boss in my entire life.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I don’t know if mistakes are funny. The biggest mistake I made was quitting my job before Christmas without my portfolio being ready. That was not a good thing to do. But I only did that once.

What do you think makes your company stand out? Can you share a story?

I like to say, we’re better than most, not as good as some. We’re passionate about what we do. I think we understand our craft. We try to make and produce meaningful work versus making landfill. We try not to make internet litter or landfill. The clients that we attract are attracted to our craft and our thinking. Ultimately everyone wants to make something beautiful and smart with people they like. We’re very fortunate to have those things at play all the time, and I think that does make us different.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

I’m trying to practice leaving at five or six o’clock every day.. It’s taken me a long time to figure out how to do that. I’m still working on it.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

Frank Martinez was in the production studio at Interbrand and he’s the one that got me my internship at the Schechter Group, which is now part of Interbrand. Also a gentleman named Young Kim. I worked for him at QVC early in my career in the early 90s. He went on to Wieden+Kennedy and opened its Tokyo office. Young was very instrumental in how I operated independently and with critical thinking and design and taste.

How have you used your success to bring goodness to the world?

I’m personally living my dream, so I try to make sure that I will always hold the door open for the next generation. That’s something that is very important to me. When I have an opportunity to interact with a young person who is just starting out or interested in the field, I really try to give them my full attention. I try to give advice, take a look at their books, or even reach out to colleagues on their behalf. Most of us that are in this position were fortunate, and I think there’s a responsibility to open the door for the next generation or the next two behind you. I like to share information with entrepreneurs because I would have loved it if someone sat down and did the same with me. That way, I could have navigated starting my own business a little smoother. I had to figure it out on the fly. When I meet an entrepreneur, I’m happy to share what I know because it doesn’t cost me anything but experience. If it can save you time, I’m happy to give you that.

What are your “5 things I wish someone told me before I started leading my company” and why. Please share a story or example for each.

There’s so many things to be honest.

  1. Make sure you love what you do.
  2. Start your agency with a client on board.
  3. Try to learn every step of the way.
  4. When things get tough, keep going.
  5. No matter how big you get, make yourself available to your clients.

Can you share a few ideas or stories from your experience about how to successfully ride the emotional highs & lows of being a founder”?

I can give you a quote that is a personal favorite of mine, which may or may not have come from Winston Churchill. “When you’re going through hell, keep going.” The way I’ve always looked at it is you can’t quit. You’re not going to die. Nothing physically bad is going to happen to you. So, you might as well see it through. You may have to close your business or downsize. You may have to move to another space. These are not terrible things. The worst thing that’s gonna happen to you is you’re going to end up in a job you don’t like making a lot of money.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

There are plenty of kids and animals that need our help and a lot of people less fortunate than us, that I would love to see the collective “we” do something more about.

How can our readers further follow your work online?

They can connect with me on LinkedIn.

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