Meet

Jess Loseke

Founder. Operator. Speaker.

Helping builders in the messy middle modernize boring businesses and scale with clarity, confidence and real strategy.

Now booking for 2026

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Get to know the Barrel Girl

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Signature Talks

Most business advice focuses on the extremes. Broke to billions. Crisis to comeback. Rock bottom to private jets. What almost no one talks about is the long stretch in the middle. The part where most businesses break and most founders feel like they are failing.

Jess lives and leads in this space. She built an eight figure company from fifty bucks and a storage unit and earned four consecutive years on the Inc. 5000 list (2022 - 2025). From the outside it looked like momentum without limits. Most Admired CEO (2024). Inc. Female Founder 500 Award (2025). Featured on 60 Minutes (2025). Behind the scenes it was real work. Hard choices. Pressure that does not make the highlight reels. When her industry swung from record highs to record lows in twelve months, everything shifted at once. It was intense. It was messy.

From fifty dollars and a storage unit to an eight figure company. A real look at how Jess transformed a messy hobby into a national brand inside a legacy industry.
The internal game founders must master. Identity, resilience, confidence and the mental clarity needed to lead when everything is hard.
The part of business no one talks about. How to navigate the seasons where systems break, pressure rises and the old playbook stops working.
How to hire well, build aligned teams and create a culture that people want to be part of in a modern workplace.

The
Neat Idea
Podcast

Coming Soon

Jess has never met a microphone she didn’t like, so it is only a matter of time before she finally launches the podcast everyone has been asking for. The Neat Idea Podcast is where The Barrel Girl breaks down the ideas, strategies and real founder conversations that help operators grow, think bigger and lead better. Consider it your weekly dose of clarity, perspective and practical insight from someone who has actually lived the messy middle. Coming soon.

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Achievements

Pitch Winner

Pipeline Entrepreneurs
Innovator of the Year

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Inc. Female Founders 500

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Most Admired CEO

Louisville Business First

Why Book Jess

Jess is an Enneagram 8, a Culture Index Trailblazer and a Predictive Index Captain. She is a rare mix of visionary and operator, which means she can see the big picture and then actually build it. She has the degrees and the accolades, but that is not what makes her valuable. Her edge comes from time in the trenches. Jess has lived the messy middle, taken every framework and operating system and run them through real people and real problems. She knows what works because she tested it when it mattered. If you want someone who can hand you tools, perspective and the push to keep going when you want to quit, Jess is the one you book.

A Note From Jess

Friends,

I love understanding how people tick. And I love the game of business. But the truth is this. If you do not know your strengths, your weaknesses and the road you are actually on, the odds are not in your favor. I am here to share the wins, but more importantly the failures, the mistakes and the messy parts that taught me the most. If you are a builder, I promise we have a lot to talk about.

Cheers!
Jess