Harder Than It Looks: Parking Uncovered
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<p>We as parking professionals know that parking is hard. However, we make it look easy to those from the outside looking in. The myriad technologies, processes and people that a parking operator has to wrangle on any given day is mind-numbing, and every parking facility is unique. While certain verticals share similar pain points, we know better than many how nuanced every operation can be.</p><p><br></p><p>We created this podcast 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.</p>
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Publishing Since
8/16/2023
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Recent Episodes
June 17, 2026
EP 55: EV Charging Is Harder Than It Looks with David Weber
<p>In this episode of Harder Than It Looks, host Brian Wolff is joined by <strong>David Weber</strong>, Head of National Business Development for Parking at SWTCH Energy. David brings more than two decades of experience across the parking industry, starting as a valet at a Las Vegas casino before moving into operations, digital parking, business development, and now EV charging infrastructure.</p><p>David’s path through parking has taken him across the parking industry. Along the way, he learned how to handle people, solve operational challenges, say yes to new opportunities, and build a career in an industry that has a way of pulling people back in.</p><p>Brian and David dig into what parking operators and asset owners need to understand about EV charging: the misconceptions, the real costs, the role of incentives, load management, uptime, and why chargers should be treated as part of the broader parking ecosystem.</p><p>David also explains why EV charging is less about becoming a major revenue stream and more about serving tenants and customers, and preparing parking assets for the future of mobility, including fleets and autonomous vehicles. </p><p><strong>Key Takeaways</strong></p><ol><li><strong>EV charging is not plug-and-play. </strong><br> Installing chargers requires understanding power availability, building infrastructure, load management, incentives, customer needs, and long-term operational goals.</li><li><strong>EV charging is an amenity and a competitive advantage.</strong><br> For garages, office buildings, multifamily properties, and urban parking assets, EV charging is increasingly becoming something customers expect.</li><li><strong>Operators need to cut through misinformation.</strong><br> David addresses common misconceptions around EV fires, vehicle weight, charger placement, and whether existing garages can support EV adoption.</li><li><strong>The real cost is often infrastructure, not the charger.</strong><br> Chargers themselves have become more affordable, but electrical work, conduit, transformers, and power capacity can drive the true project cost.</li><li><strong>Parking assets are well-positioned for the next wave of mobility </strong> With the growing trend of EV drivers, autonomous vehicles, and electric fleets, parking operators already control valuable real estate that could become essential charging and mobility hubs.</li></ol><p><strong> </strong></p><p><strong> </strong></p><p><strong>Episode Highlights<br>[02:00]</strong> David shares his career story, from growing up near Buffalo to starting as a valet at The Mirage in Las Vegas. <strong>[05:30]</strong> What David learned from working at the ground level of parking operations <strong>[11:00]</strong> Why EV charging is “much harder than it looks” and what parking operators often underestimate. <strong>[13:00]</strong> Brian and David discuss misinformation around EVs, including fires, vehicle weight, and garage placement.<br> <strong>[20:00]</strong> The EV charging checklist: budget, incentives, site walks, electrical capacity, and load management. <strong>[25:00]</strong> The future opportunity around electric fleets, self-driving cars, and overnight charging. <strong>[30:00]</strong> What installing EV chargers really will cost operators.<br><strong>[34:00]</strong> David gives a snapshot of EV adoption in the United States and where he thinks the market is headed.</p><p><strong>Notable Quotes:<br></strong><br></p><p><strong>“If you’re just getting started out in any business and it’s a little over your head, go for it.” </strong>– David Weber</p><p><strong>“EV charging is an amenity that has to be there now. If someone has an EV car, they aren’t even looking at an apartment or a complex that doesn’t have EV charging.” </strong>– David Weber</p><p><strong>“You could put four chargers in for under $10,000 and get them paid off in a couple years no problem.” </strong>– David Weber</p><p><strong>About the Guest<br></strong><br></p><p><strong>David Weber </strong>is the Head of National Business Development for Parking at SWTCH Energy, where he helps parking operators and asset owners integrate EV charging into their facilities and broader parking ecosystems.</p><p>David has spent more than 25 years in the parking industry, beginning his career as a valet before moving into supervisory, district management, operations, and business development roles. He has a practical understanding of how parking operations work on the ground, how technology gets adopted in the field, and what operators need from partners introducing new solutions.</p><p>At SWTCH Energy, David focuses on educating the parking industry about EV charging infrastructure, incentives, uptime, load management, and the future role parking assets can play in EV development and mobility operations. Known for his operational background, direct communication style, and resilience, David brings a practical perspective to one of the industry’s fastest-evolving opportunities.</p>
June 3, 2026
EP #54: Why Discernment is the New AI Superpower with Jake Miller
<p>In this episode of Harder Than It Looks, host Brian Wolff is joined by <strong>Jake Miller, </strong>Co-Founder and CEO of ZIVIS, to explore what happens when software evolves into intelligence and what it really takes to trust it. With a career spanning large scale platforms, startup innovation, and now AI security, Jake brings a systems level perspective to one of the fastest moving shifts in technology.</p><p>Jake’s journey started in networking and software engineering and expands into linguistics, entrepreneurship, and ultimately AI. He shares how thinking in systems shaped his career and the why the future belongs to those who can navigate and manage intelligent systems rather than just build them. </p><p>Brian and Jake dive into ambient intelligence, the changing nature of work, and why discernment is becoming one of the most valuable skills in the AI era. They also tackle a critical topic for any operator adopting AI: trust. Jake explains why security is no longer a one-time checkbox and must become a continuous discipline.</p><p>The adoption of AI is a direct challenge facing our industry today. As systems grow more complex and data becomes more abundant, the opportunity shifts from managing tools to interacting with intelligence.</p><p><strong>Key Takeaways</strong></p><ol><li><strong>AI is changing how we interact with technology.</strong><br> The shift is moving from structured tools to natural language interaction, where systems respond more like collaborators than software.</li><li><strong>Discernment is the new competitive advantage. </strong><br> AI can generate outputs at scale, but human judgment determines what is useful, accurate, and valuable. </li><li><strong>Start small with AI by improving your workflow.</strong><br> Your inbox, calendar, and daily processes are the easiest entry points to begin realizing immediate value.</li><li><strong>Existing companies have an advantage in AI adoption. </strong><br> Even messy data is valuable. Organizations that already have data can reverse engineer insights and accelerate faster than starting from scratch.</li><li><strong>Trust in AI must be continuous, not static. AI is changing how we interact with technology. </strong>Security, governance, and ethical use require ongoing monitoring, testing, and adaption as AI continues to evolve. </li></ol><p><strong> </strong></p><p><strong>Episode Highlights</strong></p><p><strong>[02:00]</strong> Jake shares his early career in networking and software engineering and his fascination with systems thinking.<br> <strong>[06:30]</strong> How a background in linguistics unexpectedly became foundational in the age of generative AI. <strong>[10:30]</strong> The shift from traditional SaaS tools to conversational, AI driven workflows. <strong>[15:00]</strong> Why discernment and “taste” matter more as AI generates more content. <br> <strong>[20:00]</strong> What ambient intelligence looks like in practice and how it changes data interaction. <strong>[27:00]</strong> Where to start with AI adoption using your inbox and daily operations. <strong>[34:00]</strong> The difference between AI native companies and those adapting existing systems. <br> <strong>[36:30]</strong> Why AI security requires continuous testing and new approaches like threat modeling. <strong>[41:00]</strong> Real world examples of prompt injection and how vulnerabilities can persist across systems.<br> <strong>[45:00]</strong> Practical advice for parking operators looking to adopt AI responsibility. </p><p><strong>Notable Quotes</strong></p><p><strong>“Don’t limit limit yourself and edit yourself while you are working. Let it all out. Then go back and apply judgment. </strong>– Jake Miller</p><p><strong>“Don’t write it. Reverse engineer it. Go to your data and say ‘I need a modern version of this output, how it works today.’”</strong>– Jake Miller</p><p><strong>“If you’re starting out and you’re asking yourself the question ‘What do I do with this AI thing?’ My very first answer would be ‘How do you improve your personal workflow?’” </strong>– Jake Miller</p><p><strong>About the Guest:<br></strong><br></p><p><strong>Jake Miller </strong>is the Co-Founder and CEO of ZIVIS, where he is building the next generation of AI trust and security systems for organizations operating in real world environments.</p><p>Jake has 25+ years of experience in software engineering and product development. He has led teams at ExactTarget Salesforce Marketing Cloud and has helped dozens of startups bring products from ideas to market. </p><p>Known for his systems thinking and deep technical expertise, Jake focuses on helping organizations navigate the complexity of AI while maintaining trust and security.</p>
May 20, 2026
EP 53: From Chalk to Cloud - Nexity, Towne, and the Future with Shareena Sandbrook
<p>In this episode of Harder Than It Looks, host Brian Wolff sits down with Shareena Sandbrook, Chief Commercial Development Officer at Towne. Shareena was the Co-Founder and CEO of Frogparking, a global parking technology company she co-founded with her father, Don Sandbrook, in 2009.</p><p>How do you build a global parking company from a small town in New Zealand? For Shareena, the answer involved a lot of plane rides, a lot of late nights, and a willingness to back herself. She left her young daughters at the airport more times than she can count, installed sensors herself in downtown LA in heels and a suitcase, and closed her first city deal (4,500 spaces) before her team really knew what they were doing. Sixteen years later, that first client is still with her.</p><p>Shareena grew up entrepreneurial. Her father is a self-described "crazy inventor" who pulled her into the workshop early and taught her to chase ideas no one else was working on. Before Frogparking, she sold satellite tracking software to aviation customers back when prospects would squint at the sky and ask, "Where is the cloud?" When she and her dad turned their attention to parking, the industry was still chalking tires. They saw an opening.</p><p>In 2025, Frogparking was acquired by Towne, where it became the foundation of Nexity by Towne, the industry’s first fully integrated parking and mobility platform delivered by a single provider. Shareena now leads design and development, integration, and ongoing growth, with her sights set on what she calls "world domination" and a billion-dollar company.</p><p>Key Takeaways</p><p>1. <strong>Solve real problems, and growth follows. </strong>Frogparking grew because it spotted clear gaps: wardens chalking tires, clunky access control, vendor stacks duct-taped together. The team built technology that answered customer pain directly.</p><p>2. <strong>Focus beats everything. </strong>Shareena’s playbook is relentless focus on the right strategic deals, the right customers, and a reputation worth protecting. Reputation, she says, is "absolutely critical."</p><p>3. <strong>Integration is the future of parking. </strong>A patchwork of disconnected systems is holding the industry back. One end-to-end platform from a single provider wins day in and day out: faster operations, less revenue leakage, better user experience.</p><p>4. <strong>Leadership is about shared purpose. </strong>Treat your team like family, bring them into the goal, and connect their work to a bigger mission. Nobody is above the job, including the CEO with a suitcase in downtown LA at midnight.</p><p>Episode Highlights</p><p><strong>[01:00] </strong>Meet Shareena Sandbrook and the road that led her to Towne</p><p><strong>[02:10] </strong>Growing up entrepreneurial in New Zealand and selling SaaS before the cloud was a thing</p><p><strong>[04:20] </strong>The first big city deal: 4,500 spaces, a public-private partnership, and a client still with her 16 years later</p><p><strong>[05:00] </strong>Pushing into the U.S. and spending half her life on a plane</p><p><strong>[09:30] </strong>Where the name Frogparking actually came from (hint: a sensor that looked like a frog)</p><p><strong>[10:40] </strong>Building reputation through relentless focus on the right strategic deals</p><p><strong>[12:30] </strong>Pivoting during COVID: cashless, ticketless, and patented gates that reset on impact</p><p><strong>[17:00] </strong>Extending the platform into parking guidance, access control, valet, enforcement, and permitting</p><p><strong>[19:30] </strong>Why a patchwork of fifty clunky systems is finally on its way out</p><p><strong>[21:50] </strong>The Towne rebrand and the launch of Nexity by Towne</p><p><strong>[24:30] </strong>How the team uses AI internally and in product, without making it a buzzword</p><p><strong>[27:00] </strong>Managing a tight, eclectic developer team (Monster energy and potato chips included)</p><p><strong>[29:30] </strong>What end-to-end actually looks like at Irvine Spectrum, Laguna Beach, Nike, and USC</p><p><strong>[33:30] </strong>Six months in: the contrast between scrappy startup life and life inside Towne</p><p><strong>[35:30] </strong>Leadership philosophy: family first, no titles above the work</p><p><strong>[39:00] </strong>Lightning round: the hardest things, the magic wand, hunting on horseback, and what she is most proud of</p><p>About the Guest</p><p>Shareena Sandbrook is the Chief Commercial Development Officer of Towne. Formerly, Sandbrook was the Co-Founder and CEO of Frogparking, a global parking technology company she co-founded with her father, Don Sandbrook, in 2009.</p><p>Under her leadership, Frogparking expanded into the U.S. and grew into one of the industry’s most advanced parking platforms, with a portfolio of over 30 patented technologies serving cities, airports, universities, and private operators across North America and Australasia.</p><p>In 2025, Frogparking was acquired by Towne, where it became the foundation of Nexity by Towne, Towne’s next-generation, end-to-end parking technology platform. Sandbrook continues to lead design and development, integration, and ongoing growth.</p>
70 total episodes available
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- What is Harder Than It Looks: Parking Uncovered?
<p>We as parking professionals know that parking is hard. However, we make it look easy to those from the outside looking in. The myriad technologies, processes and people that a parking operator has to wrangle on any given day is mind-numbing, and every parking facility is unique. While certain verticals share similar pain points, we know better than many how nuanced every operation can be.</p><p><br></p><p>We created this podcast 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.</p> - How often does this podcast release new episodes?
This podcast updates weekly.
- Where can I listen to this podcast?
This podcast is available on 9 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
- Does this podcast accept guests?
Information about guest appearances is not available.
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