Meet Jonathan Hessing

We had the good fortune of connecting with Jonathan Hessing and we’ve shared our conversation below.

Hi Jonathan, we’d love to hear more about how you thought about starting your own business?
You know, it really started with noticing how often smart people were building around problems instead of through them. My first company came from pure curiosity. We were sitting in a bar during the Alabama-Auburn game, watching everyone go nuts, and I thought, if this is what it’s like here in Kennesaw, imagine Tuscaloosa. We wanted to capture that energy —real, raw, user-generated moments — not the filtered version between friends.

Then Snapchat launched something similar, and we had to pivot. That’s when it clicked for me: ideas don’t matter as much as how fast you can adapt. The real skill is treating problems like puzzles and finding a way through.

ShooflyAI came from that same mindset, just more evolved. I kept seeing companies spend a fortune on “AI tools” that didn’t actually do anything. Everything felt disconnected, rented, temporary. So we built something different — a way for businesses to actually own their AI, not just subscribe to someone else’s version of it.

That’s what ShooflyAI is about. Making AI work like infrastructure, not hype. Helping businesses get real ROI, not just cool tech. At the end of the day, it’s about ownership and leverage. You should own the intelligence that runs your business. That’s why I started this business.

Can you give our readers an introduction to your business? Maybe you can share a bit about what you do and what sets you apart from others?
I’m a three-time founder who’s learned that success comes from solving real problems, not chasing trends. Every venture has taught me something different — from building consumer apps in college to leading enterprise tech teams and now shaping how companies use AI.

Early on, I made all the classic mistakes. I’d walk into meetings talking about blockchain and machine learning and lose the room. The turning point was realizing that great founders don’t sell technology — they sell outcomes. Time saved. Margin protected. Better decisions. That shift changed everything for me.

Today, with ShooflyAI, I’m applying that same mindset at scale — helping businesses own their AI infrastructure instead of renting it. I’m proud that we’ve delivered measurable ROI for clients: accounting firms saving 10+ hours a week, law firms automating intake, and restaurant groups improving margins.

The biggest lessons? Lead with clarity. Keep it simple. Prove ROI fast — weeks, not quarters.

What I want people to know about me: I’m not interested in hype. I care about building systems that actually work — for real people, in real businesses.

If you had a friend visiting you, what are some of the local spots you’d want to take them around to?
I’d want them to see the real Atlanta — and metro Atlanta — not the tourist version, but the eclectic, cultural mix that makes this place special.

We’d start slow. Breakfast at Hen Mother in Alpharetta, then drive down to the BeltLine and grab dinner at Hawkers.

Midweek, we’d hit Del Bar or Lapeer in Alpharetta. If the Braves, Falcons, or Hawks are playing, we’re catching a game. If not, a show at The Eastern — or both if the timing lines up.

One morning a hike up Kennesaw Mountain, then head into the city for drinks at the Ponce City Market rooftop, watching the skyline and just taking it all in.

And if we’ve still got energy, maybe we’d wander up to Buford for some underrated food spots.

That’s Atlanta to me — a mix of energy, culture, and good food everywhere you turn.

The Shoutout series is all about recognizing that our success and where we are in life is at least somewhat thanks to the efforts, support, mentorship, love and encouragement of others. So is there someone that you want to dedicate your shoutout to?
There are a lot of people who’ve shaped my journey, and I don’t take that lightly.

My co-founders across all ventures — Zunair, Austin, and Richard from Shii (now Streaming Global); Chris Lowe at Keyspace; Clint Crowe, my podcast co-host at HSTL UP; and Diego Herrera-Rios at ShooflyAI. Each one brought something I didn’t have, and that made the journey possible.

I would also say all of my investors, advisors, and mentors. When you have ambition, finding answers is the easy part; it’s asking the right questions that only experience can guide. Good mentors and advisors have always been a pivotal focus of mine.

One book every founder should read was recommended to me by one of my investor-mentors: *Focus on the Problem, Not the Solution* by the founder of Waze, with a foreword by Steve Wozniak. It’s pragmatic and no fluff — just what it actually takes to build something that lasts. I’ve read it twice and bought it for a bunch of people.

And last but not least, none of this would be possible without my wife and my parents. They’ve supported every crazy idea and late night. Having that kind of grounding makes everything else possible.

Website: https://shooflyai.com

Instagram: jonathanhessing

Linkedin: https://www.linkedin.com/in/jonathanhessing/

Twitter: https://x.com/JonathanHessing