Category: Blog

Podcast EP 43 Rewind: Hire for Heart, Train for Skill: Dean Ahmad’s Recipe for Leadership

October 15th, 2025

In this episode of Harder Than It Looks, host Brian Wolff is joined by Dean Ahmad, Vice President of Parking and Transportation at Dallas-Fort Worth Airport (DFW). Dean shares his remarkable journey from entrepreneurial beginnings to leading a team of over 300 employees at one of the busiest airports in the world. Dean offers insights on building organizational culture, driving innovation, and developing employees. His people-first leadership approach has resulted in the highest engagement scores at DFW, fostering an environment of collaboration and achievement.

Podcast EP 42 Rewind: Big Ten School = Big Parking: How Gabe Mendez is Rewriting the Playbook

September 26th, 2025

In this episode of Harder Than It Looks, host Brian Wolff sits down with Gabe Mendez, PTMP – Director of Transportation Operations at the University of Wisconsin Madison. Gabe brings over two decades of experience in the industry, and shares insights from his time in commercial parking operations to leading transportation services at one of America’s largest universities.

Podcast EP 41 Rewind: Disruption Ahead! Bob Murray & James Paden on Parking’s Next Big Shift

August 21st, 2025

In this episode of Harder Than It Looks Parking Uncovered, host Brian Wolff sits down with Bob Murray, CTO at CampusParc, and James Paden, Chief Product Officer at Parker Technology. These tech veterans share their experiences transitioning into the parking industry and offer insights on how outside expertise is driving innovation in parking operations.

Podcast EP 40 Rewind: Service, Struggle, and Strength – The Making of Amano’s CEO, Greg Brewer

August 14th, 2025

In this episode of Harder Than It Looks Parking Uncovered, Brian Wolf sits down with Greg Brewer, the newly appointed President and CEO of Amano McGann, Inc. Greg shares his inspiring journey from humble beginnings to leading one of the parking industry’s top technology providers. He offers insights on authentic leadership, company culture transformation, and balancing technological innovation with essential human interaction in parking operations.

Podcast EP 39 Rewind: Humans Still Win – The AI-Augmented Future of Parking

August 7th, 2025

In this episode of Harder Than It Looks, Brian Wolff is joined by James Paden, Chief Product Officer at Parker Technology. With 25 years of software experience, James shares his insights on the rapidly evolving world of AI in the parking industry. From the challenges of implementing voice AI to the future of customer service, this conversation explores how parking is both leading and adapting to technological change.

Podcast EP 38 Rewind: Live from IPMI – 9 Parking Experts on Tech Trends, Customer Pain Points & Parking’s Future

July 17th, 2025

In this special episode, recorded live on the expo hall floor at IPMI 2025, Brian Wolff, Heidi Barber, Tina Gray, and Courtney Cooper talk to 9 parking leaders about what’s working, what’s not, and what they’d change with a magic wand. From drones and data to broken gates and customer confusion – it’s a rapid-fire tour of the industry’s most pressing challenges.

Podcast EP 37 Rewind: LEDs, Guidance, and Grit

June 25th, 2025

In this episode of Harder Than It Looks, Brian Wolff sits down with Jeff Pinyot – the President of ECO Parking Technologies.

Jeff’s journey started in Pittsburgh and evolved from air conditioning sales to pioneering lighting solutions – and finally to developing the world’s first fully integrated wireless parking guidance system. With multiple patents, a knack for invention (yes, even soda packaging), and a passion for helping others grow, Jeff opens up about the risks, the pivots, and the purpose that drive his work.

Podcast EP 36 Rewind: “You’re Going to Ruin Our City!”

June 5th, 2025

In this episode, host Brian Wolff is joined by Kenzie Coulson, Parking and Mobility Consultant at Walker Consultants, known for leading high-stakes projects like Park City’s paid parking rollout and Salt Lake City’s City Creek parking overhaul.

Kenzie shares behind-the-scenes stories about transforming emotionally charged parking environments, navigating complex municipal politics, and balancing leadership with vulnerability. Listen in to learn why “parking is never just about parking,” and how understanding human dynamics can drive operational success.

Podcast EP 35 Rewind: They Told Sue Malone “No.”

June 5th, 2025

In this episode, host Brian Wolff is joined by the extraordinary Sue Malone – the first woman to operate a parking garage in the U.S., and the nation’s most prolific small business lender.

After being denied a loan for her own business, Sue took matters into her own hands. The result? Over 41,000 SBA loans funded to date – with a mission to reach 100,000. She shares unfiltered stories from her early parking days (car thefts, Bondo, and FBI calls), her journey into small business advocacy, and why she’s built a career on empowering veterans, women, and underrepresented entrepreneurs.

This conversation is a masterclass in grit, civic leadership, and the power of saying “yes” when the world says “no.

Podcast EP 34 Rewind: Tech, Tolls & Takeovers

May 22nd, 2025

In this live episode recorded at PIE25, Brian welcomes Andrew Bess, Managing Director at TrueNorth Capital Partners. With over two decades of experience in strategic advisory and corporate finance, Andrew has advised industry-shaping companies like Icon Parking, The Car Park, Oobeo, Valet Manager, On Air Parking, and CurbTrac.

Category: Blog

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