About BitterSweet Marketing – Evansville Social Media and Video Content Agency

Our Story

BitterSweet started in 2020 with a camera, a lot of trial and error, and the simple idea that real people make the best stories. Back then, that meant music videos for local artists—long nights, big ideas, and way too much time spent chasing the “perfect” shot. The work was fun and meaningful, but eventually a hard truth set in: views are great, but if they don’t lead anywhere, they’re just numbers.

That realization changed the direction—fast.

When BitterSweet began working with local businesses, the focus shifted from polish to purpose. The goal became simple: make content that actually does something. That shift paid off in a big way while building the social presence for local auto shops—from zero to over 100 million organic views in six months. No gimmicks. No trends. Just real people, real work, and stories worth watching.

That’s when it clicked.

Most businesses aren’t struggling because they’re bad at what they do. They’re excellent. What holds them back is everything around it—visibility, connection, and telling their story in a way people actually care about. Social media, when done right, is powerful because it’s personal. It lives in people’s pockets, shows up in quiet moments, and builds familiarity that no billboard ever could.

Today, BitterSweet creates organic, story-driven social media that feels human because it is. We don’t do cookie-cutter content or play it safe. We lean into personality, humor, honesty, and the occasional imperfect moment—because that’s what people remember. Life is bittersweet. Business is too. We just help make the good parts louder and the hard parts worth something.

The Bitter in BitterSweet

Jessie Bitter is an Evansville native, lifelong artist, and—according to his wife’s 9-year-old sister—a professional skateboarder.

From a young age, Jessie has always been pulled toward drawing and anything creative. As he likes to say, “the whole world changes when you pick up a skateboard.” Stairs stop being just stairs—they become something to kickflip over. A massive curved church roof isn’t just architecture anymore; it’s “wouldn’t it be wild if someone could drop in on that?”

Skateboarding may be nothing more than a piece of wood, two trucks, and four wheels—but it completely reshaped how Jessie sees the world. It changed how he approaches creativity, business, marketing, and people. Every obstacle is different. Every person has their own story, goals, and way of moving through life.

Jessie never stopped skating, and he never stopped creating. Whether he’s drawing his favorite musicians, learning a new trick, or chasing a better idea, he’s always pushing himself to improve—just a little more than the day before.

Over the years, that mindset has led him from working with non-profits, to filming music videos for local artists, and helping local businesses build authentic, lasting social media presence that actually works. The focus has always been the same: real people, real stories, and the ones who make it all happen.