All Episodes

Most Recent Episode

Podcast EP 58 Rewind: 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 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.

Check out our most recent episode >

Podcast EP 57 Rewind: 850 Square Miles: How Peter Sherwill Runs Parking for the Biggest City in America

September 3rd, 2026 | Blake Richmond

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 roughly 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.

Podcast EP 56 Rewind: The Curb: Transportation’s Toughest Puzzle with Benito Pèrez

August 4th, 2026 | Blake Richmond

In this episode of Harder Than It Looks, host Brian Wolff is joined by Benito O. Pèrez, 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 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 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.

Podcast EP 54 Rewind: Why Discernment is the New AI Superpower with Jake Miller

June 17th, 2026 | Blake Richmond

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 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.

Podcast EP 53 Rewind: “From Chalk to Cloud” – Nexity, Towne, and The Future

May 21st, 2026 | Blake Richmond

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.
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.

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.

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.

Podcast EP 52 Rewind: Karen Mangia: 100 Reviews Can Double Your Business. Here’s How to Get Them.

May 21st, 2026 | Blake Richmond

In this episode of Harder Than It Looks, host Brian Wolff is joined by Karen Mangia, SVP of Global Customer Success at Bazaarvoice. Karen is a Wall Street Journal bestselling author and a proven customer experience expert.

Karen’s career spans leadership roles at Salesforce, Cisco, and now Bazaarvoice, where she helps brands harness the authentic voice of their customers to drive loyalty and growth. From her early days as a research assistant to leading global customer success teams, Karen shares how listening – really listening – can transform business.

The conversation dives into where companies fall short in customer feedback, how reviews influence behavior more than ever, and what service-based industries (including parking) can learn from world-class customer experience programs.

Karen also shares what attendees of FUSION26 can look forward to in her keynote presentation, including strategies to take control of reviews with proactive growth tools, leverage user-generated content to build trust and visibility, and how to convert it all into measurable revenue and business impact.

Podcast EP 51 Rewind: “You Can’t Fall Out of a Basement” with Neil Hart

May 6th, 2026 | Blake Richmond

In this episode of Harder Than It Looks, host Brian Wolff sits down with Neil Hart, Vice President of University Operations at Reimagined Parking. With more than 30 years of experience spanning private parking, healthcare, and higher education, Neil brings a rare, full spectrum perspective on leading in a service industry.

People don’t often plan on starting out in our industry, but once they get in, it’s hard to get out. Neil planned on being a sportswriter, but an assistant manager job at a valet parking operation in college introduced Neil to the parking industry. Now, after 30 years, Neil shares the lessons learned from saying “yes” to the right opportunities.

Neil and Brian discuss the intricacies of managing massive auxiliary operations – including parking, food service, housing, and transportation. Through all his experiences and all his teams, Neil explains why success ultimately comes down to people, process, and technology.

Neil brings calm leadership under pressure, a servant’s heart, and commitment to success in every opportunity faced over his career.

Podcast EP 50 Rewind: Today, Tomorrow, and Tomorrowland

April 15th, 2026 | Blake Richmond

In this episode of Harder Than It Looks, host Brian Wolff sits down with Keith B. Jones, Chairman and Owner of ACE Parking – the largest family-owned parking and mobility company in North America.

Founded in 1950 by Keith’s grandparents in San Diego, ACE Parking began as a dirt lot charging 25 cents for a parking spot. Today, the company operates across the country and stands as one of the most respected organizations in the industry.

Keith shares his journey, beginning with an early interest in customer experience. From directing traffic in stadium parking lots at 10 years old to leading ACE for more than two decades, Keith has a lifelong fascination with parking. The conversation shifts to servant leadership, defining an living by true integrity, nevigating technological disruption, and balancing innovation with the long-term responsibility of a family-operated company.

Keith leads ACE Parking by effectively balancing future ambition with current realities, while enduring ACE Parking remains a strong pillar of the San Diego and other communities.

Podcast EP 49 Rewind: Meet Dr. Tanara Teal-Tate: 200 Pages, 18,000 Spaces, and a $24M Empire

April 2nd, 2026 | Blake Richmond

In this episode of Harder Than It Looks, guest host Heidi Barber sits down with Dr. Tanara Teal-Tate, Executive Director of Parking & Transportation at the University of Tennessee, Knoxville – a leader overseeing a $24M+ auxiliary enterprise serving more than 50,000 campus community members.

With responsibility for 18,000+ parking spaces, 10 garages, 34 bus transit systems and a 60+ person team, Dr. Teal-Tate understands firsthand that parking and transportation is mission-critical infrastructure. Dr. Teal-Tate brings a 25-year journey shaped by grit, data-driven leadership, cross-campus collaboration, and a commitment to student success.

From earning three degrees to leading a dynamic team, rolling out transformational parking changes, and defining mobility at a flagship university, Dr. Teal-Tate shares what it takes to lead a complex operation in higher education.

Podcast EP 48 Rewind: How Kevin Uhlenhaker is Building an Independent Voice for Parking

March 19th, 2026 | Blake Richmond

In this episode of Harder Than It Looks, host Brian Wolff sits down with Kevin Uhlenhaker, CEO & Publisher of Parking Today Media.

Kevin shares insight from his first year as the CEO & Publisher of Parking Today Media, including the innovations made to PIE 2026. PIE 2026 is held in Dallas, Texas, from March 30th-April 2nd. Kevin and Brian discuss the challenges associated with taking over an established media publication, and how Kevin’s idea of honoring legends of the parking industry will create a legacy for years to come.

Podcast EP 47 Rewind: Collaboration Is Not Optional: What 30 Years in Parking Taught Maggie Vercoe

February 25th, 2026 | Blake Richmond

In this episode of Harder Than It Looks, host Brian Wolff sits down with Maggie Vercoe, COO of TEZ Technology and a 30-year veteran of the parking industry.

From starting in a parking booth at the University of Wisconsin-Milwaukee to helping build T2 Systems during its high-growth years – and now leading professional services, support, account management, and marketing at TEZ – Maggie shares the leadership lessons that shaped her journey.

This conversation dives deep into adaptive leadership, managing complex implementations, staying calm in conflict, and why collaboration isn’t just a buzzword – it’s a survival skill in parking.

All Episodes

Most Recent Episode

Podcast EP 58 Rewind: A House Fire, A 2AM Call, and a Career in Parking with Melissa Jones

Interested in being on the podcast?