EP 34: Tech, Tolls, and Takeovers - Parking’s Next Big Chapter with Andy Bess

In this special 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. 

He shares why parking is far more complex than most outsiders realize—from its operational intricacies to the data and tech gaps that still challenge operators today. Whether you're a municipal leader, tech innovator, or operator navigating consolidation, this episode delivers deep insights into the evolving world of urban mobility and smart city infrastructure. 

 Key Takeaways 

• The Real Complexity of Parking: Why 80% of the business is accounting—and how that drives tech adoption. 
• From Geology to Deal-Making: Andrew’s fascinating route from mobile labs in Europe to New York boardrooms. 
• Why Tech is Still Catching Up: Parking’s fragmentation is a barrier—but also a massive opportunity. 
• Trends Reshaping the Industry: Curb management, EV charging, AI, and what the next wave of change looks like. 
• Smart Growth Through Consolidation: Why private operators are being scooped up—and what buyers are really looking for. 

 Episode Highlights 

• [00:00:20] Welcome from PIE25 – Brian introduces Andrew and kicks off the live podcast. 
• [00:02:55] Andrew’s career journey: from geology to investment banking to parking tech. 
• [00:05:05] Running cross-border deals, founding firms, and falling in love with negotiation. 
• [00:06:50] Inside the Icon Parking transaction—and how it exposed a massive tech opportunity. 
• [00:09:20] Why most of parking is accounting—and how that complicates software. 
• [00:12:50] Real-world complexity: one person, three parker identities in a day. 
• [00:14:20] Parking tech: where we are now and what the next evolution looks like. 
• [00:17:30] AVs, Waymo, and how autonomous trends intersect with Gateless and LPR. 
• [00:21:30] The curb is calling: congestion pricing, regulations, and infrastructure gaps. 
• [00:24:50] Tech consolidation and the inflection point for small providers. 
• [00:26:20] Why small private operators are ripe for acquisition—and what’s driving the wave. 
• [00:29:20] The role of generational change in ownership transitions. 
• [00:31:20] Parking demand isn’t dying—why trips still require a place to park. 
• [00:32:50] The truth about EV charging: it’s an amenity, not a cash cow. 
• [00:34:35] AI in parking: real innovation or just a fancy label for BI? 
• [00:36:50] Lightning Round: running the Grand Canyon, favorite phrases, and what Andrew’s most proud of. 
• [00:42:20] Audience Q&A: dynamic pricing, RFP bottlenecks, and the power of standardization. 

Subscribe and Stay Connected 

Never miss an episode of Harder Than It Looks: Parking Uncovered. Subscribe on: 

• Apple Podcasts 
• Spotify 
• Amazon Music 
• YouTube 

Learn more at www.parkertechnology.com
Contact: getstarted@parkertechnology.com