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Harder Than It Looks: Parking Uncovered: Daily Summaries Delivered
by Parker Technology
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.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.
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- 4 days ago1h 4m
EP 61: "Can I Hug You?" Matt Fahlman on the Booth Moment That Changed OffStreet
In this episode of Harder Than It Looks, host Brian Wolff sits down with Matt Fahlman, Co-founder and CEO of OffStreet, the market leader in guest permitting software for universities across North America.Matt takes Brian back to the beginning: a frigid Saskatchewan winter, a pay-by-phone parking line and an early idea that led him and co-founder Kyle Smyth into parking tech. He shares the IPMI booth moment that pointed OffStreet toward universities, the mentor advice that sharpened the company’s focus, and how a core value of “good vibes, high standards” shapes who they hire. Matt and Brian also compare notes on leading a growing team, keeping everyone aligned as the company scales, and OffStreet’s vision to become the industry’s most trusted permitting platform. Key Takeaways1. Pay attention when the market tells you where to go.A university director’s reaction at an IPMI booth was the light bulb moment that showed OffStreet where guest permitting could make the biggest difference. 2. Say yes to get started, then get focused to grow.From zero to $1 million, you take every opportunity. From $1 million to $10 million, focus is what drives growth. 3. Good vibes and high standards go together.OffStreet hires for both, and the result is very low turnover and deep institutional knowledge across the team. 4. As the team grows, the CEO becomes the storyteller.Matt shifted from hands-on, day-to-day work toward sharing a clear long-term vision so every new hire can connect their work to the company’s goals. 5. Trust earns the right to do more.Expansion conversations with campus partners came after years of delivering, which is what drives OffStreet’s goal to be the industry’s most trusted permitting platform. Episode Highlights[00:39] Brian introduces Matt and looks back on OffStreet’s early trade show days.[02:24] Matt’s story, from corporate finance to Googling how to start a tech startup.[03:29] Teaming up with co-founder Kyle Smyth and the first version of the company.[06:41] Minus 40 in Saskatchewan and a pay-by-phone line: why Matt picked parking.[10:59] An early CEO lesson: your team takes your ideas more literally than you expect.[17:24] Building product through COVID and the path to universities.[19:37] The IPMI booth moment: “Can I hug you?”[20:28] Guest permitting, 100+ campuses and 40-45 new universities in 2026.[21:49] Say yes to everything to $1M, then get focused to reach $10M.[25:02] Good vibes, high standards and the advantage of low turnover.[31:05] Keeping a growing team aligned and shifting toward the long-term vision.[39:46] Partnerships, white labeling and owning the customer relationship.[42:43] OffStreet’s vision to become the industry’s most trusted permitting platform.[50:22] The VIP guest who needs parking but won’t share a plate number.[54:52] Lightning round: Matt’s go-to phrase, his magic wand fix for parking and what he’s most proud of. Notable Quotes“This will be okay. It’s a solvable problem.” - Matt Fahlman“One of our core values is good vibes, high standards, and you can’t have one without the other.” - Matt Fahlman“What a privilege to be in this position to be dealing with those problems.” - Matt Fahlman About the GuestMatt Fahlman is the Co-founder & CEO of OffStreet - one of the industry’s fastest growing tech startups. OffStreet is the market leader in guest permitting software and works with over 100 campuses across North America. Matt has built and scaled the company to 40+ employees, and OffStreet processes millions of digital permits annually.
- 3 weeks ago1h 6m
EP 60: The Power of Moments - How Marc Baumann Designs Experiences People Remember
In this episode of Harder Than It Looks, host Brian Wolff sits down with Marc Baumann, Founder and Principal of South Lane Advisory and former Chairman and CEO of SP+. Their conversation centers on The Power of Moments by Chip and Dan Heath, a book Marc has sent to more people than any other.Marc walks Brian through how SP+ found its purpose, Making Every Moment Matter for a World on the Go, starting with one question: what actually motivates more than 20,000 frontline team members? He shares how co-creating that purpose with hundreds of leaders helped it take hold, why "do the right thing" sometimes meant handing a client a check, and why he made a habit of parking at competitors' garages. Marc and Brian also dig into why the best moments are planned in advance, how small gestures from leaders can stay with someone for years, and where technology can deliver a better experience in the lane than people expect.Key TakeawaysPurpose is what unlocks discretionary effort. Everyone knows the minimum their job requires. A purpose people can relate to is what moves them toward their maximum.Co-create the purpose instead of announcing it. SP+ built its purpose with a cross-section of 20 people, then tested it with 300 leaders, and it was repeated back by frontline teams within months.Doing the right thing pays off over the long run. From owning a costly mistake with a check to recommending another company's technology when it was the better fit, Marc saw integrity keep clients.Plan the moments in advance, including the ones machines deliver. Every customer touchpoint can be anticipated, and designing for the worst-case scenarios is how you cut down on bad moments.Small moments carry real weight. Commenting on someone's name or snapping a photo with a frontline team member can become a moment that person remembers for years.Episode Highlights[00:21] Brian introduces Marc and the FUSION26 conversation that inspired this episode.[04:00] A director's question about frontline motivation, the NASA janitor story, and the idea of discretionary effort.[07:00] "We're just parking cars": how Marc reframed parking around giving people back their time.[11:20] Tell, sell, consult, co-create: how SP+ landed on Making Every Moment Matter for a World on the Go.[16:00] How Marc knew the purpose was taking hold, and the unscripted video SP+ filmed across five cities.[22:00] Core values versus platitudes, and why Marc's phone number and email were available to anyone who asked.[29:00] Recommending another company's technology and owning a $20,000 mistake with a check.[34:40] The biggest lesson from The Power of Moments: plan the moments before they happen.[37:30] Marc's own lost-ticket moment in a lane, and what technology can do differently.[43:10] Why Marc parked at competitors' facilities to see the customer experience firsthand.[48:30] A lost stuffed animal, a wheelchair attendant, and the power of a photo with the CEO.[54:00] Lightning round: Marc's go-to phrase, the hardest thing he's ever done, and what he's most proud of.Notable Quotes"Nothing changes if nothing changes." - Marc Baumann"Sometimes a machine can deliver a better experience than a person. I can't believe I'm actually saying that." - Marc Baumann"A moment doesn't have to be an elaborate thing. It can be a very small thing." - Marc BaumannAbout the GuestMarc Baumann is the Founder and Principal of South Lane Advisory LLC, which provides Board-level and C-suite advice on strategy, organization design, operations and financial management, technology, transformation initiatives, succession planning, corporate governance, and mergers and acquisitions. Marc played key leadership roles in three successful business turnarounds as well as in all facets of public company management, compliance and investor relations.Marc has recently concluded a 23-year career with SP Plus Corporation, (NASDAQ: SP), having negotiated its successful sale in a take-private transaction at a 52% premium to its pre-announcement share price. Marc served as CEO during his final nine years and, for the last three of those years, also as Chairman of the Board of Directors. Prior to his roles as CEO and Chairman, Marc served as the Company's COO and CFO. Marc led a team of over 20,000 employees at nearly 4,000 locations providing an extensive range of services encompassing professional parking management, grou
- Sep 2, 202657 min
EP 59: The Truth about Voice AI – and Our Work to Perfect It
In this episode of Harder Than It Looks, host Brian Wolff welcomes back James Paden, Chief Product Officer at Parker Technology. Brian and James celebrate two years since James joined the company, and they unpack the AI products James and his team launched. Brian and James dig into the actual mechanics of a voice AI call, the five different AI models a single call runs through in about a second, and why building AI for parking is a challenge. James walks through Parker Technology’s newly launched AI agent, Ambassador, which comes in two powerful solutions. Ambassador Live provides AI-powered assistance, with human back-up always available. Ambassador Assist tackles a market Parker has never been able to serve at scale before - the everyday phone calls that flood parking offices. The conversations get into the guardrails behind the technology: the quality that Tammy Baker, COO, and her team had already established for Parker’s CSRs, and how that became the standard AI had to meet before it could go live. Key Takeaways 1. AI is built to augment humans, not replace them. AI can handle the fast, repetitive questions so human agents can focus on the complex, high-empathy situations that require more thought.2. Building Voice AI in parking is a harder problem than most voice AI. Outdoor speakers, background noise, and real-time facility data (broken equipment, special event pricing) make the acoustic challenges far tougher than a cell phone call.3. Ambassador’s guardrails were built by the Parker Standard. Tammy Baker, COO of Parker Technology, and her team have set existing quality standards for CSR’s. Ambassador was built with the same high standards, with a hard rule that any uncertainty routes straight to a human.4. AI opens markets Parker couldn’t serve before. Ambassador Assist is built for high-volume, unpredictable call environments that were too complex to staff profitably in the past. Episode Highlights [01:00] James reflects on two years at Parker and how his outside perspective sharpened once he started paying attention to parking as a technology problem. [06:00] Why James and Brian believe capital and attention are flowing into the parking industry. [10:00] How Ambassador Assist opens a market Parker hasn’t been able to serve at scale – starting with university parking offices. [14:00] James walks through what happens during a Voice AI call: audio cleanup, voice activity detection, speech-to-text, the language model, and text-to-speech, all in about a second. [18:00] The hardest parts of building voice AI for parking: the noisy outdoor acoustic environment and the deep facility-specific knowledge required to answer correctly. [21:00] How every AI interaction gets tested, graded by other AI systems, and run through the same quality assurance process as human agents. [23:00] Why Parker is investing in AI even with two strong call centers already in place: speed multilingual support, and staffing flexibility. [29:00] The philosophy behind Ambassador: making it easy to reach a human and treating AI as expansion. [35:00] How Tammy Baker’s existing quality standard became the bar Ambassador had to meet, including the rule that any uncertainty transfers straight to a human. [44:00] Parker’s pricing approach for Ambassador Live and Ambassador Assist, and why alignment drives both models. [54:00] James previews his NPA Las Vegas session on the four levels of AI for building a parking roadmap, and where to find the Parker team at Booth 400. Notable Quotes “AI’s not there to replace. It’s there to augment, to expand, to make the environment faster.” – James Paden “Ambassador Assist meets our customers in an area where we haven’t been able to meet them before.” – James Paden “When I joined Parker, there was already an established bar that the AI had to meet.” – James Paden About the Guest James Paden is the Chief Product Officer at Parker Technology, where, for the past two years, he leads the product and engineering teams behind the company’s parking support platform, including its new AI agent, Ambassador. James brings more than 25 years of software and product development exp
- Aug 26, 202645 min
EP 58: A House Fire, a 2AM Call, and a Career in Parking with Melissa Jones
In this episode of Harder Than It Looks, host Brian Wolff sits down with Melissa Jones, PTMP, Director of Customer Experience at TEZ Technology.Melissa’s road into parking wound began with a career in counseling and crisis work with at-risk kids and families. That work taught her how to sit with people in the middle of a crisis, big or small, and help them work through it. These skills ended up translating directly into leading teams and supporting customers who call in with their own version of an emergency. Counseling and parking kept pulling her back and forth until it finally stuck for good, taking her through managing parking at Class A office buildings, a stint at Parking Soft that turned into a decade at T2, and now her role at TEZ. Melissa and Brian dig into how that unlikely combination of backgrounds quietly built the leader she is today. The conversation covers building trust quickly in high-pressure environments, creating health conflict without ill will, what it takes to lead technically strong but low-EQ team members, and how the industry’s growing number of strong woman leaders are changing the game. Key Takeaways1. Your background is never wasted. Melissa’s years in counseling and crisis management, and her work as a fitness coach, translate directly into how she leads teams and supports customers today.2. Bedrock leadership is about openness, not skill. Melissa can teach anyone the software or the job. What she can’t teach is flexibility, empathy, and a willingness to learn. Those traits must come from the person.3. Healthy conflict starts with relevance. Melissa’s approach to hard conversations is simple: make it relevant to the person in front of you and ask how you’d want someone you love to be treated. 4. Trust is built by walking the walk. Having answered the phones and taken the heated calls herself, Melissa leads by showing up in the lane, owning it when things go sideways, and never throwing her team to the wolves.5. The industry has changed – and so have the leaders. As From hauling a coin canister through snowy parking lots to today’s technology and customer experience standards, Melissa has watched the industry raise its bar, along with a growing wave of strong women leaders shaping its future. Episode Highlights[02:00] Melissa shares how she got started in counseling and how a friend first talked her into taking a parking manager job at a community college. [04:00] The career pull between parking and counseling, with a journey through both.[06:00] A move to a Class A office building in downtown Atlanta reintroduces Melissa to parking, this time falling in love with the managerial and people side of the work.[9:00] Melissa’s journey from Mardi Gras parking to T2.[12:00] Melissa lands at TEZ Technology as Director of Customer Experience, overseeing implementation and customer experience.[14:00] Brian and Melissa discuss leading technically strong but low-EQ team members, and the importance of meeting people where they are.[24:00] The story of a tough property manager in Atlanta who became Melissa’s best friend, and the servant leadership lesson she taught Melissa.[32:00] Melissa’s 20-year parking journey, and the lessons she’s learned by being a woman in parking leadership.[38:00] Lightning round: Melissa’s go-to phrase, the hardest thing she’s ever done, and what she’s most proud of. Notable Quotes“I can teach anybody the software. I can teach anybody the job. What I can’t teach you is to be flexible and empathetic and open to learning. – Melissa Jones“If I rise because of you, then that means somebody else can rise because of me.” – Melissa Jones“We’re never going to be alone and trying to figure out things. That’s work or personal. I’m right there… you can’t get rid of me.” – Melissa JonesAbout the GuestMelissa Jones, PTMP, is the Director of Customer Experience at TEZ Technology, where she leads the implementation and support teams. She is a PTMP member and an active contributor to multiple IPMI communities. Melissa’s career spans more than 20 years across account services, and customer support, including roles on community college campuses, in Class A office buildings, at events, and in valet services. She joined Parking Soft’s training department before its acqui
- Aug 12, 202654 min
EP 57: 850 Square Miles: How Peter Sherwill Runs Parking for the Biggest City in America
In this episode of Harder Than It Looks, host Brian Wolff is joined by Peter Sherwill, Chief Public Parking Officer for the City of Jacksonville, the largest city by land area in the contiguous United States. Peter brings more than two decades of parking and mobility experience spanning valet, event parking, municipal operations, and private sector contracts, and now oversees a system of garages, surface lots, on-street parking, and enforcement across 850 square miles.Peter walks Brian through his winding path into parking, starting as a high school valet attendant and working his way through event parking at venues like Red Rocks Ampitheatre, municipal operations in Denver, and a private sector stop in Fort Myers before landing in Jacksonville. Brian and Peter dig into how Peter keeps a lean 40-person team motivated without a formal appreciation budget, how the department earned a seat at the table for major city projects, and how Jacksonville is modernizing decades-old technology while preserving the ambassador-like role of enforcement staff. They close with a look at the next big challenges facing curb management as downtown Jacksonville grows.Key Takeaways1. Motivation doesn't require a big budget. Without funds for employee perks, small gestures, such as dedicated a employee break room, new uniforms, "Win Wednesday" recognition meetings, have transformed a once-fragmented enforcement team into one that has each other's backs.2. If you want a seat at the table, you have to take initiative. Parking teams are often the last to know about city projects that affect the curb. Peter changed that in Jacksonville by proactively reaching out to other departments and showing up as a problem solver, not an afterthought.3. Modern technology should remove friction, not remove people. Jacksonville is rolling out multi-space meters, online permitting, and updated LPR systems, while intentionally keeping staff visible and approachable so automation doesn't replace the human side of the customer experience. 4. The Curb is everchanging. As downtown Jacksonville adds housing, a rebuilt stadium, and more nightlife, the parking team expects to expand enforcement hours, add residential permit programs, and manage rising demand from rideshare and delivery traffic. Episode Highlights[02:00] Introducing Peter Sherwill and his origin story.[04:00] Learning municipal parking in Denver and expanding paid parking in Fort Myers, Florida.[06:00] The surprise twist that turned a different job interview into an offer for Chief Public Parking Officer.[12:00] Keeping a lean team motivated without an appreciation budget - break rooms, new uniforms, and "Win Wednesday".[17:00] A technology rundown: multi-space meters, online permitting, new LPR systems, and upgraded garage equipment.[19:00] Stakeholder stories: booting a city council member's car and creative curb solutions for a century-old downtown business.[30:00] Cross-departmental collaboration on downtown revitalization, the new Jaguars stadium, and micro-mobility expansion.[36:00] How Peter earned parking a seat at the table early in major city projects.[38:00] Balancing automation with a human touch by turning enforcement staff into downtown ambassadors.[43:00] Looking ahead: curb demand from deliveries and rideshare, micro mobility, and expanding enforcement hours.[48:00] Lightning round: Peter's go-to phrase, hardest career challenge, and what he's most proud of.Notable Quotes"It's just parking, it's not rocket science. We can figure anything out." - Peter Sherwill"I will carry the baton for whatever project it is as far as I must, to hand it off to the next person. I don't just wait for that baton to come back - I take the next one." - Peter Sherwill"If you need something to be successful at your job, let us know what it is. As long as it's reasonable, we're going to get it for you. I don't think I've said no once." - Peter SherwillAbout the GuestPeter Sherwill is the Chief Public Parking Officer for the City of Jacksonville, overseeing a comprehensive system of parking garages, surface lots, on-street parking, and enforcement across 850 square miles - the largest city by land area in the contiguous United States.Peter has more than 20 years of experience in municipal and private sector parking operations, including event parking for sports and entertainment venues, short-term garage and valet operations at Denver International Airport, and municipal parking leadership in Denver and Fort Myers. He is
- Jul 29, 20261h 3m
EP 56: The Curb: Transportation's Toughest Puzzle with Benito Pèrez
In this episode of Harder Than It Looks, host Brian Wolff sits down with Benito O. Pérez, AICP, CTP, CPM, PTMP, Section Chief for Transit Capital Statewide at the Illinois Department of Transportation.Benito’s career has moved through urban planning, civil engineering, transportation policy, curbside management, accessibility, and transit capital planning. But the common thread through all of it is connection: connecting planners and engineers, connecting agencies and advocates, connecting infrastructure decisions to real human experience, and connecting today’s transportation choices to the communities we want in the future.The conversation also gets into the curb: why it is one of the most contested and misunderstood spaces in transportation, how accessibility has to go beyond the parking space, and why public agencies need to think more intentionally about every user who interacts with streets, sidewalks, transit, bike lanes, parking, and the curb.Benito also shares what he’s working on now at IDOT, helping transit agencies across downstate Illinois access capital funding for buses, maintenance facilities, transfer centers, and long-term infrastructure needs. His advice is simple but important: don’t just plan for what you need today. Think about what your system needs to become.Key TakeawaysTransportation problems are rarely siloed. Parking, transit, biking, walking, land use, accessibility, and curbside management all intersect. The best solutions come when agencies and stakeholders stop treating them as separate conversations. The curb is where everything comes together. Benito describes the curb as a friction point where transportation systems meet land use, access, mobility, policy, and real-world user needs. Accessibility has to be built into the whole journey. Accessible parking matters, but the experience does not stop once someone gets out of the vehicle. Streetscapes, crossings, bike lanes, transit access, and signal timing all shape whether a place is truly accessible. Long-term planning requires more than today’s need. Benito encourages agencies to think about their 20-year buildout, especially when funding is available, so they do not solve today’s problem only to create tomorrow’s constraint. Public agencies and advocates need each other. Benito makes the case that advocates and practitioners are often working toward the same goals, but they need better communication, transparency, and trust to move things forward. Episode Highlights[02:00] Benito shares how growing up in a Navy family exposed him to transportation systems in Europe and shaped the way he thought about cities.[03:00] Why Benito first thought he wanted to be an architect, and how an advisor helped him realize he was more interested in the “architecture of space.”[06:00] A pivotal meeting with planners and engineers helped Benito realize he wanted to become a translator between disciplines.[09:00] Brian and Benito discuss why transportation, housing, land use, and parking have historically been siloed.[11:00] Benito explains how the rise of the car shaped zoning, street design, transportation policy, and the way communities developed.[20:00] Benito explains his current role at IDOT, overseeing transit capital funding outside of metro Chicago.[22:00] Why rural transit is often lifeline transportation for seniors, people with disabilities, and people accessing healthcare, food, and other essential services.[24:00] Benito explains why agencies should plan for their 20-year buildout, not just what they need right now.[30:00] Benito discusses the challenge of integrating ADA and accessibility into long-range transportation planning.[36:00] A powerful example of how flashing traffic signals can unintentionally create barriers for people with cognitive disabilities.[39:00] Where public sector leaders and operators should start if they want to do better around accessibility.[43:00] Why curbside management needs to be treated as a regional issue, not just a local one.[49:00] Lightning round: Benito’s go-to phrases, including “Curbside management is not a sprint, it’s a marathon.”Notable Quotes“Curbside management is not a sprint, it’s a marathon.” – Benito Pérez“It’s not a war on cars, it’s a war on the idea that car is the only option.” – Benito Pérez“We need to take a step back and think about both
- Jun 17, 202644 min
EP 55: EV Charging Is Harder Than It Looks with David Weber
In this episode of Harder Than It Looks, host Brian Wolff is joined by David Weber, 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.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.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.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. Key TakeawaysEV charging is not plug-and-play. Installing chargers requires understanding power availability, building infrastructure, load management, incentives, customer needs, and long-term operational goals.EV charging is an amenity and a competitive advantage. For garages, office buildings, multifamily properties, and urban parking assets, EV charging is increasingly becoming something customers expect.Operators need to cut through misinformation. David addresses common misconceptions around EV fires, vehicle weight, charger placement, and whether existing garages can support EV adoption.The real cost is often infrastructure, not the charger. Chargers themselves have become more affordable, but electrical work, conduit, transformers, and power capacity can drive the true project cost.Parking assets are well-positioned for the next wave of mobility 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. Episode Highlights[02:00] David shares his career story, from growing up near Buffalo to starting as a valet at The Mirage in Las Vegas. [05:30] What David learned from working at the ground level of parking operations [11:00] Why EV charging is “much harder than it looks” and what parking operators often underestimate. [13:00] Brian and David discuss misinformation around EVs, including fires, vehicle weight, and garage placement. [20:00] The EV charging checklist: budget, incentives, site walks, electrical capacity, and load management. [25:00] The future opportunity around electric fleets, self-driving cars, and overnight charging. [30:00] What installing EV chargers really will cost operators.[34:00] David gives a snapshot of EV adoption in the United States and where he thinks the market is headed.Notable Quotes:“If you’re just getting started out in any business and it’s a little over your head, go for it.” – David Weber“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.” – David Weber“You could put four chargers in for under $10,000 and get them paid off in a couple years no problem.” – David WeberAbout the GuestDavid Weber 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.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.At SWTCH Energ
- Jun 3, 202657 min
EP #54: Why Discernment is the New AI Superpower with Jake Miller
In this episode of Harder Than It Looks, host Brian Wolff is joined by Jake Miller, 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.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. 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.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.Key TakeawaysAI is changing how we interact with technology. The shift is moving from structured tools to natural language interaction, where systems respond more like collaborators than software.Discernment is the new competitive advantage. AI can generate outputs at scale, but human judgment determines what is useful, accurate, and valuable. Start small with AI by improving your workflow. Your inbox, calendar, and daily processes are the easiest entry points to begin realizing immediate value.Existing companies have an advantage in AI adoption. Even messy data is valuable. Organizations that already have data can reverse engineer insights and accelerate faster than starting from scratch.Trust in AI must be continuous, not static. AI is changing how we interact with technology. Security, governance, and ethical use require ongoing monitoring, testing, and adaption as AI continues to evolve. Episode Highlights[02:00] Jake shares his early career in networking and software engineering and his fascination with systems thinking. [06:30] How a background in linguistics unexpectedly became foundational in the age of generative AI. [10:30] The shift from traditional SaaS tools to conversational, AI driven workflows. [15:00] Why discernment and “taste” matter more as AI generates more content. [20:00] What ambient intelligence looks like in practice and how it changes data interaction. [27:00] Where to start with AI adoption using your inbox and daily operations. [34:00] The difference between AI native companies and those adapting existing systems. [36:30] Why AI security requires continuous testing and new approaches like threat modeling. [41:00] Real world examples of prompt injection and how vulnerabilities can persist across systems. [45:00] Practical advice for parking operators looking to adopt AI responsibility. Notable Quotes“Don’t limit limit yourself and edit yourself while you are working. Let it all out. Then go back and apply judgment. – Jake Miller“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.’”– Jake Miller“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?’” – Jake MillerAbout the Guest:Jake Miller 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.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. Known for his systems thinking and deep technical expertise, Jake focuses on helping organizations navigate the complexity of AI while maintaining trust and security.
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About Harder Than It Looks: Parking Uncovered
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.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.
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Frequently Asked Questions
What is Podzilla's Harder Than It Looks: Parking Uncovered daily summary?
It's a free AI-powered email that summarizes new episodes of Harder Than It Looks: Parking Uncovered as soon as they're published. You get the key takeaways, notable quotes, and links & mentions — all in a quick read.
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How often does Harder Than It Looks: Parking Uncovered release new episodes?
Harder Than It Looks: Parking Uncovered publishes biweekly. Our AI generates a summary within hours of each new episode.
What topics does Harder Than It Looks: Parking Uncovered cover?
Harder Than It Looks: Parking Uncovered covers topics including Technology, Business. Our AI identifies the specific themes in each episode and highlights what matters most to you.
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