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5 Things I Wish Someone Told Me Before I Became CEO of AdQuick, with Matt O’Connor

Go bigger than you think you can earlier: At the beginning of the start-up, I think the team lacked the confidence to approach the largest buyers or media owners in the space for fear that our product wasn’t good enough or based on an assumption that they would have a great solution. As we’ve grown […]

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Go bigger than you think you can earlier: At the beginning of the start-up, I think the team lacked the confidence to approach the largest buyers or media owners in the space for fear that our product wasn’t good enough or based on an assumption that they would have a great solution. As we’ve grown and simply become better at our business, we’ve realized our solution would have been a good fit for both. Worst case scenario, you learn what you’re lacking and then you can prioritize. If you don’t push the conversations, you stay in the cave of ignorance, which is the worst place to be.


I had the pleasure to interview Matt O’Connor. Matt is the CEO and co-founder of AdQuick, the first platform to allow marketers and agencies to complete the entire process of planning; buying, executing and measuring out of home (OOH) advertising campaigns anywhere in the U.S. Prior to AdQuick, Matt worked as a Senior Program Manager with Amazon.com and held various executive positions within Instacart. His entrepreneurial spirit began as the founder of Footprint Free a company that helps businesses go green and connect with their consumers and then again as Founder of Bike to the Beach, a community of people who combine biking, purpose, and fun to inspire individuals to overcome obstacles through personal challenge. Matt earned his B.A. from the University of Notre Dame and MBA from the University of Virginia’s Darden Graduate School of Business Administration.


Thank you so much for joining us Matt! Can you tell us the story about what brought you to this specific career path?

Back in January of 2017 I set out with a few amazing co-founders (Fahim Ferdous, Stephen Wegner and Connor Burden) on a journey to modernize the outdoor advertising industry. The company (called AdQuick) has been in the works so to speak for over seven years. AdQuick makes buying outdoor advertising faster, more targeted, and more measurable than ever before. By doing so, we also hope to make selling it easier as well.

Rewind a bit to 2010. I was bootstrapping a start-up called Footprint Free. We brought on our first customer and wanted to promote the win. What better way than with some outdoor advertising. All I wanted was to see — which options were available at what price for what timeframe. Simple, right?

Weeks after submitting requests through multiple company websites, I finally heard back from one company. Instead of sending me options with pricing and details, I had to go through a consultation call where I relayed the same details I sent in my initial outreach. After our unnecessary phone call, the sales rep sent me an email with dozens of attachments called ‘photo sheets’ and separate attachments with pricing information. It was a tedious process to say the least.

It turned out the $200 bucks I was looking to spend was too low for any of the available options. Instead, I “bribed” some friends who lived in a high-visibility location with six-pack and some pizza. In return, they displayed our ad. After that experience, the seed was planted.

Fast forward a few years to 2014–15. I joined Instacart and was part of the expansion team. We were a team of six that swooped into markets, got Instacart up and running, spread the word as loudly as possible, then moved onto the next market. Time was always of the essence.

Entering a new market, our main goals were to delight customers with an amazing new service and make sure as many people as possible knew that Instacart arrived — and do it fast. We expanded from three to 12 markets in eight months.

When our team looked into purchasing outdoor advertising, the launches came and went before we could get quotes for available inventory in our launch markets. We would deploy our budgets in faster-to-execute channels, like digital marketing. Seemingly nothing had changed in 5 years.

When I left Instacart to go to Amazon, the idea continued to gnaw at me. While driving one afternoon from Houston to New Orleans the highways were littered with ‘Your Ad Here’ billboards. The lost value from the locations I saw first-hand was in the millions of dollars annually. After doing some more diligence on the industry, I learned that at any given time, 30–40% of outdoor advertising is vacant.

I couldn’t stop thinking about it. And while the idea at the time was nascent, there was no fundamental reason that the idea for AdQuick wouldn’t work — and fast forward — and here we are today!

Can you share one of the major challenges you encountered when first leading the company? What lesson did you learn from that?

I wasn’t intimately familiar with one side of the business, so learning about the nuances of media owners, their needs and the opportunities that technology could present to them. There was a lot of learning and listening from this side of the marketplace.

What are some of the factors that you believe led to your eventual success?

I’ve worked in a number of scenarios in which I wasn’t experienced, so I’ve gotten pretty adept at listening and translating problems into technology solutions.

What are your “5 Things I Wish Someone Told Me Before I Became CEO”? Please share a story or example for each.

  • Go bigger than you think you can earlier: At the beginning of the start-up, I think the team lacked the confidence to approach the largest buyers or media owners in the space for fear that our product wasn’t good enough or based on an assumption that they would have a great solution. As we’ve grown and simply become better at our business, we’ve realized our solution would have been a good fit for both. Worst case scenario, you learn what you’re lacking and then you can prioritize. If you don’t push the conversations, you stay in the cave of ignorance, which is the worst place to be.
  • The rollercoaster is real — You’re truly never as bad as you think or as good as you may feel. Remember this in particular during any down times.
  • “Do the hard things first” — Continuously assess your company’s biggest risk and work to figure that part out.
  • Remember you’re building something for the long term — It’s very unlikely that any occurrence on a single day or hour will make or break your company. Staying consistent over time is the key
  • Don’t be a hero — If you’re building a company of material size, extended periods of “doing it all” or touching every part of the company are shortsighted. Hire great people and then clear the lane for them to do their best work.

What advice would you give to your colleagues to help them to thrive and not “burn out”? 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?

We’ve been fortunate enough to receive help from dozens and dozens of people throughout the process, so it’s hard to just single out one person. One of the most surprising things about the journey has been how some people, without any close tie or affinity for me or the company, have been incredibly helpful with no ulterior motive. Remember to ask for help — often times it’s simply a question away.

The best advice I can give would be to find a hobby, skill, or pursuit that you can do outside of work that requires consistent progress. Start-ups are notoriously difficult and volatile, so developing a skill or hobby that can maintain your spirits during tough times really helps a lot.

Also, don’t forget to call your mom!

What are some of the goals you still have and are working to accomplish, both personally and professionally?

On a personal level I’d like to “pay it forward” by mentoring other entrepreneurs and share insights, challenges, successes and even some of the tough lessons learned along the way

Professionally I feel that the company (AdQuick) has just scratched the surface of what we can accomplish in the industry. We still have a lot of progress to make but in doing so I believe that we are building a world class company culture where our people will also grow personally and professionally when they join our team.

What do you hope to leave as your lasting legacy?

A person that left things better than he found them and was a “friend to man” (A favorite quote of mine from The House by the Side of the Road)

You are a person of great influence. If you could start a movement that would enhance people’s lives in some way, what would it be? You never know what your idea can trigger!

Short and sweet — zoom out from your personal lens and realize that you may not know all of the context.

How can our readers follow you on social media?

Best way to find me on social media is via Twitter @morrisonoc

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