Simon is a serial entrepreneur, a seasoned veteran of the creative agency world, an illustrator, a game designer, and user experience and visual design expert. He began his career at Valiant Comics in 1992 working as a designer and illustrator in comic books. It was there he became one of the first computer letterers in the industry and began creating the first digital paintings ever produced in comics. Much of his early illustration work was for Marvel and DC Comics creating digital paintings for licensed trading cards and covers.
Simon spent the next eight years as a design and creative consultant in New York City for some of the largest companies in the world. While in New York, Simon co-founded Ember Media which introduced the original CD-ROM business card, the “DigiCard,” to America and ran a high-profile interactive agency producing multimedia content.
An Austin native, Simon returned home and over the course of twenty years launched several companies. His most recent, SiteGoals (an interactive agency that merged with Workhorse Marketing in 2018), Quotingly (quote and proposal software), and Argle Bargle The Game Where You Insult Your Friends. Simon’s newest venture is Trooper, a startup that is focused on website updates and maintenance for agencies and small businesses.
Throughout his career, he’s worked with hundreds of clients including American Express, Dow Jones & Company, ESPN, Estée Lauder, Fish & Richardson, HBO, Logitech, Marvel Comics Group, Mastercard, Miller Brewing, Newsweek, Nickelodeon, Polycom, R/GA, Saatchi & Saatchi, Showtime, Sony Online, and the United Nations.
Simon enjoys kayak fishing, rock climbing, live music, art, comics, and games. He’s mentored for SXSW and continues to contribute to the Austin creative agency community. In 2006, Simon was selected by Nintendo Entertainment to be the Austin Ambassador for Nintendo (Yes, that’s a real title). This also confirms he’s a total geek.
Where did the idea for Trooper come from?
The idea for Trooper came from the last few years of helping clients and friends manage and maintain their websites. I realized that most of the work being done didn’t require a full-time developer, but still needed someone at the ready to help support a client’s needs at any time. I realized that there’s an army of people ready to do the work, but there’s a barrier to hiring those individuals. I want to remove that barrier while still providing the comfort and security needed to effectively handle the work.
What does your typical day look like and how do you make it productive?
I don’t know if I’d consider all of my days the most ‘productive’, but I wear a lot of hats. I work in two main shifts. The first starts mid-morning, around 11am and goes until the end of a typical workday, around 5pm. Then I usually take a break and spend time with my family, eat dinner, workout, and enjoy some leisure time. Often, in the later evening, I sit back down at my desk and work until 1am (sometimes later). This helps me communicate with workers that are overseas as well as giving me a time to work where I am uninterrupted by the outside world.
How do you bring ideas to life?
It sounds cliché, but I bring ideas to life with the help of others. I talk to friends and strangers and find my allies, believers, and people to help keep me honest. I push and work hard, and believe that I can accomplish anything that I set my mind to.
What’s one trend that excites you?
Global connectivity. It’s been decades in the making but you can go online and read about someone on the other side of the planet and reach out, communicate, and collaborate with that person. The miles don’t matter. Language rarely matters. The world has truly been made small by technology.
What is one habit of yours that makes you more productive as an entrepreneur?
Don’t stop to think about it, do the thing. Early in my career I was working for a guy in New York City who ran a client services company. There was a moment where we had to deliver bad news to a client, and it was going to be a tough phone call to make. He immediately picked up the phone and dialed the number, not even taking a minute to think about how challenging this conversation would be. After, he said that he made sure that when he was faced with something he doesn’t want to do, he just does it. Throws himself into the task without taking a minute to second guess or procrastinate on something he didn’t want to do. It has been something that I have carried with me throughout my career. I apply this type of thinking to most situations that I don’t want to deal with.
What advice would you give your younger self?
Don’t get distracted doing things that don’t benefit you in the long run. I spent a lot of time in my 30’s going out with friends. I did more than my share of drinking at bars and clubs and spent a lot of time that didn’t ultimately contribute to my future. I had fun, from what I can remember, but at the end of the day it was a lot of lost time – which is our most valuable asset.
Tell us something that’s true that almost nobody agrees with you on.
Ben Affleck was the best Bruce Wayne, and also one of the most accurate portrayals of Batman in the movies. I catch hell from all my geek friends when I say this, but there were moments of pure Batman perfection when Affleck was playing him. Now, don’t get me wrong, the three movies he appeared in were not great, but his Frank Miller-esque Batman hit the mark as far as I’m concerned.
As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?
I wake up every day and remind myself that I am lucky enough to have another day where I get to decide what I want to do to move my life forward. It may be something productive, it may be something frivolous. Either way, it’s my choice.
What is one strategy that has helped you grow your business?
Persistence and determination, there is no substitute. Plan and execute on your vision. Reach out, talk to people. Get out of your comfort zone. Share your ideas and see if you can find other people who believe in the same.
What is one failure you had as an entrepreneur, and how did you overcome it?
In early 2020 I was in the process of merging my application development business with a new partner. On the surface it seemed like a great fit, we both had complementary aspects to our capabilities and both were bringing some existing customers to the new entity. Then the pandemic hit and several of our clients suspended their business through most of 2020. We continued to work to merge our businesses and were at the precipice of launching the new (combined) company, when the new partner pushed broken code and refused to work to resolve it because he didn’t want to work after hours. It turned into a huge confrontation that ultimately made me pull the plug overnight on the entire venture that I had spent the better part of the year building.
It made me realize that there’s no substitute for knowing someone’s core values and that equal partnerships are extremely difficult to maintain without a high level of trust in the individual you’re partnering with.
What is the best $100 you recently spent? What and why?
I’m a big fan of the Larq water bottle. It has a built in bacteria killing UV light in the cap that cleans your bottle and purifies your water. I drink a lot of water but hated how my water bottle would smell after a couple of days. This water bottle keeps my water at a nice cool temperature and smells clean for weeks. I love it. I carry it around with me every day.
What is one piece of software or a web service that helps you be productive?
I use, and have used, many types of project management software but I find that Any.do is very helpful to keep track of my personal daily and weekly tasks. It’s cross-platform and has a nice feature on the mobile app that nudges me to review my list each morning and set a goal of when I plan on tackling it. I don’t always do it, but it continues to remind me until I do.
What is the one book that you recommend our community should read and why?
Disrupt You! by Jay Samit. This book really spoke to me and has continued to inspire me in the way that Jay shifts his perspective when trying to solve problems. It talks both about entrepreneurial journeys as well as personal struggles, and helps break down ways to solve challenges that can cripple your business. Jay’s writing and speaking style are approachable and clear. He doesn’t overcomplicate it while still delivering insightful, actionable advice.
What is your favorite quote?
Press On! Nothing in this world can take the place of persistence. Talent will not; nothing is more common than unsuccessful men with talent. Genius will not; unrewarded genius is almost a proverb. Education will not; the world is full of educated derelicts. Persistence and determination alone are omnipotent.
~ Calvin Coolidge
- The world is small and open, take advantage of that to build your global workforce.
- Jump headlong into tasks you don’t want to do. Don’t give yourself the opportunity to chicken out or procrastinate.
- Persistence and determination, there is no substitute.
- Do, or do not. There is no try.
Mario Schulzke is the Founder of ideamensch, which he started a decade ago to learn from entrepreneurs and give them a platform for their ideas.