The Long Game: Paul’s Journey from Agency Kid to Tech Founder

Walk us through your childhood… what moments played a part in you becoming the founder you are today?

Paul’s journey to founding Plein Air began early, thanks to unique experiences in his father’s ad agency. While most kids were chatting about sports, Paul was drawn to the magic of creativity and the inner workings of the advertising world. “I was the kid who’d talk about famous founders like Bill Bernbach instead of football,” he says with a smile. Growing up in that creative whirlwind gave him a love for bold ideas that still drives him. Founding Plein Air felt like the natural next step, following in the footsteps of the visionaries he admired from a young age.

Beyond the office, another life-shaping experience was skydiving, which he took up and completed over 500 jumps. For Paul, skydiving became a kind of active meditation, offering a unique moment of stillness amid the thrill. “When you’re mid-fall, everything else falls away. It’s just you and the moment,” he reflects. While his skydiving is on pause for now since becoming a father, the clarity it brought stays with him—guiding his mindset as a founder, husband, and dad.

Affirmations have been a big part of you life… Can you share a bit about it?

Paul’s relationship with affirmations is rooted in a love of writing, a gift he inherited from his father, who was also a fan of jotting down thoughts and reminders. For him, words are more than a daily boost; they’re a grounding force. “They help me remember what’s important,” he says, adding that affirmations serve as a personal compass, guiding him back to his core goals and values, especially when things get chaotic. This practice has been a quiet yet steadying force, anchoring him in his roles as founder, father, and partner.

What inspired you to start your company?

Starting Plein Air was a dream Paul had for years, and the journey was anything but straightforward. After leading a marketing technology team for some time, he felt his role had run its course and wanted to rediscover purpose in his work. Around that time, Paul went through a series of personal shifts—meeting his wife, losing his father, and supporting his mother through illness—that all nudged him toward reevaluating his path.

From that soul-searching came the inspiration to found Plein Air with a small team of like-minded people. “It was about finally building something authentic and driven by purpose,” he shares. For Paul, Plein Air isn’t just a business; it’s his chance to create something meaningful and transformative for the industry.

What led you to focus on the restaurant industry?

Plein Air’s move to focus on the restaurant industry came about naturally as Paul and his team recognized its unique landscape. Unlike many other sectors, restaurants have a strong regional character, with countless niches and specific needs that offer room for innovation. “You can work with a seafood restaurant and a burger chain without stepping on toes,” Paul explains. This regional diversity meant they could really hone in and make a difference.

As they delved deeper, Plein Air carved out a niche for themselves, creating custom tech solutions that address the challenges modern restaurants face. This focus has given Plein Air a strong identity and direction, aligning perfectly with their expertise.

What’s a common misconception about your industry?

One big misconception about marketing and tech, Paul shares, is that it’s as easy as flipping a switch. In reality, creating a seamless experience requires careful planning and coordination. “People think you can just turn it on, but there’s so much that goes into it,” he explains. At Plein Air, they prioritize building practical solutions that address real needs while ensuring that these platforms are as visually compelling as they are functional. “Our focus has always been on blending functionality with a strong creative touch,” Paul adds, noting that the end goal is a solution that is both reliable and aesthetically engaging, giving clients an experience that’s intuitive and impactful.

What keeps you up at night as a founder?

Paul’s main worry as a founder? His team and the environment he’s creating for them. “It’s about having the right people and making sure they’re in a place where they can thrive,” he says. Plein Air’s culture leans heavily on freedom and accountability, which means finding people who value autonomy is essential. As the company has grown, Paul has kept a close eye on maintaining that balance, always asking how they can stay as nimble and connected as they were when they were just 20 people.

If you had to start over, what would you do differently?

Looking back, Paul would have pursued funding sooner. From the start, Plein Air chose to reinvest everything back into the business, which kept them independent but also meant slower growth. “We’ve poured everything back in,” he reflects, knowing that while this has limited their speed, it also allowed them to build on their terms. He values the control they’ve retained, even if it meant a few sacrifices along the way.

Favorite quote you’re inspired by?

Paul’s go-to phrase, proudly tattooed on his arm, reads: “Play the long game, ask big questions, let it rip.” These words capture his whole approach to life and work, emphasizing patience, curiosity, and bravery. Another tattoo, simply “hustle,” is a nod to his upbringing and work ethic. “You may not always be the smartest, but you can outwork anyone,” he says. For Paul, these reminders go beyond business—they’re about staying grounded in life and keeping focused on the long game.