Skip to main content
“Harder Than It Looks: Parking Uncovered” is our podcast that we use to facilitate connections and illuminate solutions to common problems within the parking and mobility industry.
We aim to do so by highlighting the voices of experts in the space, discussing trends and forward-looking technological innovations, and providing professional food for thought. All in an effort to help one another get better at what we know is harder than it looks…parking a car.
Today, we’re rewinding and recapping Episode 34: Tech, Tolls & Takeovers: Parking’s Next Big Chapter with Andy Bess.
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.
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.
Meet Our Guests:
Andrew Bess
Managing Director at TrueNorth Capital Partners
Andrew Bess is a Managing Director at TrueNorth Capital Partners and has worked on a broad array of strategic advisory and corporate finance transactions over the past 20 years. Andrew has a particular interest in Smart Cities and urban mobility transactions, having advised companies including Icon Parking, The Car Park, Oobeo, Inc., Valet Manager, On Air Parking, CurbTrac and others. He previously established Palmer Capital Advisors, a FINRA-registered broker-dealer, on behalf of a New York-based private equity firm. Prior to Palmer, he was a founder and managing director at Daroth Capital Advisors, a boutique investment bank. Andrew previously worked as an investment banker with both Wasserstein Perella & Co. and Ernst & Young. He holds a BA from Colby College and an MBA from Columbia University.
Andrew is the membership chairperson for the New Jersey chapter of Exit Planning Exchange, a community of professional advisors who help owners build valuable businesses and assist them in preparing and executing a successful transition. He holds Series 7, 24, 63 and 79 securities licenses.
You Won’t Want to Miss These Clips:
Episode Highlights:
- Welcome from PIE25 – Brian introduces Andrew and kicks off the live podcast (00:20)
- Andrew’s career journey: from geology to investment banking to parking tech (02:55)
- Running cross-border deals, founding firms, and falling in love with negotiation (05:05)
- Inside the Icon Parking transaction – and how it exposed a massive tech opportunity (06:50)
- Why most of parking is accounting—and how that complicates software (09:20)
- Real-world complexity: one person, three parker identities in a day (12:50)
- Parking tech: where we are now and what the next evolution looks like (14:20)
- AVs, Waymo, and how autonomous trends intersect with Gateless and LPR (17:30)
- The curb is calling: congestion pricing, regulations, and infrastructure gaps (21:30)
- Tech consolidation and the inflection point for small providers (24:50)
- Why small private operators are ripe for acquisition – and what’s driving the wave (26:20)
- The role of generational change in ownership transitions (29:20)
- Parking demand isn’t dying – why trips still require a place to park (31:20)
- The truth about EV charging: it’s an amenity, not a cash cow (32:50)
- AI in parking: real innovation or just a fancy label for BI? (34:35)
- Lightning Round: running the Grand Canyon, favorite phrases, and what Andrew’s most proud of (36:50)
- Audience Q&A: dynamic pricing, RFP bottlenecks, and the power of standardization (42:20)
Want to be notified when new episodes come out? Subscribe below!
Click Here to Subscribe via Apple Podcasts
Click Here to Subscribe via Spotify
Click Here to Subscribe via Amazon Music
If you have a chance, please leave an honest rating and review on Apple Podcasts by clicking here. It will help the show and its ranking on Apple Podcasts incredibly! Thank you so much!
Want to help the show?
Tell us about you! Please visit parkertechnology.com/podcastsurvey and fill out our short survey to help us deliver more great episodes like this one.
Thank you for listening! Find all our previous podcast episodes here.
Katelyn Perman
Content Marketing Manager
Katelyn Perman has 4+ years of experience in marketing, specializing in social media strategy, email campaigns, graphic design and copywriting. She holds a B.S. in Strategic Communication and Human Communication Studies from Indiana Wesleyan University.