In this episode of Harder Than It Looks, host Brian Wolff sits down with Kevin Uhlenhaker, CEO & Publisher of Parking Today Media.

Kevin shares insight from his first year as the CEO & Publisher of Parking Today Media, including the innovations made to PIE 2026. PIE 2026 is held in Dallas, Texas, from March 30th- April 2nd. Kevin and Brian discuss the challenges associated with taking over an established media publication, and how Kevin’s idea of honoring legends of the parking industry will create a legacy for years to come.

Kevin isn’t afraid to admit that his journey with Parking Today Media has been an uphill battle. However, his grit and determination have fueled the many successes Parking Today Media has enjoyed over the past two years. Tune in to learn more about the Kevin’s leadership mindset, and the can’t miss action that will take place at PIE 2026.

Additionally, listeners of Harder Than It Looks can use the code HTIL100 to get 100% off a standard registration for PIE 2026.

Key Takeaways

1. Success takes time
   Although Kevin is experienced in the industry, Parking Today Media still experienced challenges and growing pains.
2. A notable shift in a legendary tradeshow
   PIE 2026 will be held in Dallas, Texas, this year. It will feature many new characteristics while still honoring the legacy that PIE has.
3. Staying impartial as a media company
   Parking Today Media works hard to be purely informative in its copy and deliverables, focusing on giving parking professionals a reliable source of news.
4. Trusting team members
   Kevin acknowledges the hard and diligent work of his team and how bringing on key personnel has improved team dynamics and Parking Today Media output.

Episode Highlights

[00:00:00] Brian introduces Kevin Uhlenhaker and reflects on his first full year leading Parking Today during its 30th anniversary milestone.

[00:01:31] Kevin admits, “It really has been harder than it looks,” describing the steep learning curve of running a media company.

[00:04:00] The surprising reach and personal impact of Parking Today across industry careers.

[00:05:00] Reframing parking for outsiders: worst parking experience vs. best parking experience.

[00:09:00] The weight of visibility: why leading Parking Today carries higher stakes than past ventures.

[00:10:00] Responsibility of independence—tackling hard industry conversations.

[00:18:00] Leadership lessons: making hard decisions, evolving skill sets, and understanding industry nuance.

[00:21:00] Modernizing Parking Today while honoring its legacy—new editor, tech stack overhaul, and integration of ParkNews.

[00:27:00] Why Dallas? Accessibility, neutrality, affordability, and thoughtful event design.

[00:31:00] New PI content structure—segment-focused tracks and curated industry-wide topics.

[00:37:00] What success looks like for PI 2026: feeling welcome, connected, and among “parking family.”

[00:41:00] How Hall of Fame inductees are selected—rubric, independence, and impact.

[00:49:00] Startup mode: why there’s little spare time during this reinvention phase.

[00:52:00] What Kevin is most proud of—his family’s support and shared sacrifice behind Parking Today.

[00:54:00] Special offer: PI 2026 promo code (HTIL100) for Harder Than It Looks listeners.

Notable Quotes

“Some of the strengths that allow you to lead at one stage become the weaknesses at the next”– Kevin Uhlenhaker

“We’re not on anyone’s side. We’re on everyone’s side – Kevin Uhlenhaker

“We want PIE to be something you experience because you’re there – Kevin Uhlenhaker

About the Guest

Kevin Uhlenhaker is the CEO & Publisher of Parking Today Media. He brings 25+ years experience in the parking industry to the table. An accomplished entrepreneur, Kevin has co-founded and led multiple parking technology companies through inception to acquisition. He has been the CEO & Publisher of Parking Today Media for two years, taking the company, and the Parking Industry Expo (PIE) to new levels.