Every fall, we bring our agents together for a weekend focused on personal and professional growth, and this year’s Agent Roundtable might have been our best yet. On September 25 and 26, agents from across the country joined us at the Crossroads Hotel in Kansas City for two packed days of learning from experts and each other. Of course, we topped it all off by cheering on the Royals at their game against Cleveland. And while the game may not have gone our way, we all still walked away from the weekend feeling like winners.
The Roundtable is where newer agents get to learn from veterans with million-dollar books, and where those veterans get pushed to think even bigger. Nobody leaves the room the same way they walked in. Here’s how the weekend played out — and why this professional development experience is unlike anything else in the freight industry.
Friday: Finding Your 10
We kicked things off on Friday with lunch and some vision-casting from Tallgrass President Sean Richardson, who walked agents through what the weekend had in store and how to get the most out of it. Then it was time to get a little uncomfortable.
Ellie Martin, Tallgrass’s Director of Human Resources, led a session she called “Break Your Brain,” and the premise was simple. On a scale of 1 to 10, where’s your business at right now? And what would it take to get it to a 10? Agents mapped what they needed to stop doing, what they needed to start doing, and what life would look like on the other side. Goals ranged from more leads and bigger accounts to less stress, more time with family and growing their teams.
Ellie pushed everyone to get specific by using real numbers and painting a clear picture of where they wanted to be a year from now. As she put it, “Vagueness lives in vagueness — and no one ever desires vagueness.” Ellie also reminded agents that once you hit your 10, it becomes your new 2, and you’ve gotta keep climbing. She added that “everyone has blind spots that get in the way of success,” and learning to spot yours is a big part of what’ll help you grow. From there, agents swapped ideas about what success looks like in practice and how they’ve each built their own vision for their future.
Leaning Into LTL
Next, Bob Brown and Jacob Ward took the floor to talk all things LTL. They worked through the obstacles that keep some agents away from this mode, while agents who love selling LTL shared what has been working for them. Bob and Jacob also dove into the new technology we’re bringing in to support LTL and where the opportunities lie for agents who are ready to lean into this lucrative opportunity.
Staying a Step Ahead of Fraud
We all know freight fraud isn’t going anywhere anytime soon, so we brought in Danielle Spinelli, also known as the Fraud Girl, to help us navigate it. She covered everything from the latest headlines to the industries and states being targeted most, and what law enforcement and legal experts are seeing right now. Agents left the discussion armed with practical ways to protect their business in the current market.
An Open Floor
Friday wrapped with an open discussion, a favorite among our agents and where our Roundtable really shines. Whatever challenge you’re up against, chances are that someone in the room has already figured it out.
Agents shared what’s working in sales and customer development, and got honest about what keeps them up at night. Agents swapped solutions for serving current accounts while still finding time to prospect. After all that brainstorming, agents traded their notepads for a cocktail and headed to happy hour with the Tallgrass team, where the freight talk kept flowing.
Saturday: Money Talk and Lessons From the Pros
Saturday started with breakfast and a financial planning session with Jordan from our friends at Renaissance Financial. Jordan broke down the pros and cons of sole proprietorships, S-Corps, and C-Corps, including the tax implications of each, sharing helpful case studies from agents at various stages of business.
Next, agents rotated between tables of seasoned freight agents for breakout sessions. These smaller conversations make it easy to ask the questions you might not raise in a big group, from setting prospecting goals and motivating employees to staying motivated when the market gets rough.
As always, the agent panel was a highlight. Our panelists opened up about what brought them to Tallgrass, how they’ve built their teams and offices, and how they handle compensation. They swapped a few horror stories (every agent has one) and shared what they wish they’d known earlier in their freight careers. Veteran agents encouraged the group to lean on their fellow agents and never lose sight of your “why.”
Taking It Out to the Ballgame
After two full days of learning, we headed over to Kauffman Stadium to catch the Royals as they took on Cleveland. It gave everyone one more chance to swap stories with friends both old and new. It was the perfect way to close out a jam-packed weekend!
See You at the Next One!
That’s a wrap on another successful Roundtable! Every year, our agents remind us just how much they have to teach one another, and we can’t wait to see what they do with everything they picked up from the weekend. Agents look back on the Roundtable as a turning point: a moment when things changed for the better in their business and they reached new heights of success.
If you want a brokerage that invests in your growth and surrounds you with people who want to see you win, now is the time to reach out. Learn more about becoming an agent with Tallgrass and make sure you’re in the room for our next Roundtable.



