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

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 Takeaways 1. AI 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. 2. Discernment is the new competitive advantage.  AI can generate outputs at scale, but human judgment determines what is useful, accurate, and valuable.  3. Start small with AI by improving your workflow. Your inbox, calendar, and daily processes are the easiest entry points to begin realizing immediate value. 4. 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. 5. 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 Miller About 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.

EP 53: From Chalk to Cloud - Nexity, Towne, and the Future with Shareena Sandbrook

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. Key Takeaways 1.     Solve real problems, and growth follows. 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. 2.     Focus beats everything. 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." 3.     Integration is the future of parking. 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. 4.     Leadership is about shared purpose. 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. Episode Highlights [01:00]  Meet Shareena Sandbrook and the road that led her to Towne [02:10]  Growing up entrepreneurial in New Zealand and selling SaaS before the cloud was a thing [04:20]  The first big city deal: 4,500 spaces, a public-private partnership, and a client still with her 16 years later [05:00]  Pushing into the U.S. and spending half her life on a plane [09:30]  Where the name Frogparking actually came from (hint: a sensor that looked like a frog) [10:40]  Building reputation through relentless focus on the right strategic deals [12:30]  Pivoting during COVID: cashless, ticketless, and patented gates that reset on impact [17:00]  Extending the platform into parking guidance, access control, valet, enforcement, and permitting [19:30]  Why a patchwork of fifty clunky systems is finally on its way out [21:50]  The Towne rebrand and the launch of Nexity by Towne [24:30]  How the team uses AI internally and in product, without making it a buzzword [27:00]  Managing a tight, eclectic developer team (Monster energy and potato chips included) [29:30]  What end-to-end actually looks like at Irvine Spectrum, Laguna Beach, Nike, and USC [33:30]  Six months in: the contrast between scrappy startup life and life inside Towne [35:30]  Leadership philosophy: family first, no titles above the work [39:00]  Lightning round: the hardest things, the magic wand, hunting on horseback, and what she is most proud of About the Guest 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. 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. 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.

EP 52: Karen Mangia - 100 Reviews Can Double Your Business. Here's How to Get Them

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.  Key Takeaways  1. Customer success is the purpose of the business.  Every role contributes to delivering value to the customer, not just a designated team.  2. Negative Feedback is one of your most valuable assets. Unhappy customers reveal gaps in execution and often point to simple fixes with big impact.  3. Reviews are a powerful driver of trust and conversion. More reviews increase credibility, visibility, and ultimately influence purchasing behavior.  4. Action matters more than insight.  Collecting feedback is meaningless unless it leads to consistent, repeatable improvements.  5. Small, intentional changes can shift perception quickly. Simple actions can dramatically improve customer sentiment.  Episode Highlights  [00:18] Introduction to Karen Mangia and her background in customer experience. [02:30] Early career roots in research and understanding human behavior.      [6:30] Transition from sales leadership into customer experience. [08:30] Why customer success is everyone’s responsibility.  [11:30] Inside Bazaarvoice: capturing, verifying, and scaling customer reviews. [18:30] Why negative reviews matter and how responses build trust. [21:30] Unlocking the “stranded value in customer feedback”. [24:00] Practical ways to capture feedback in service-driven environments.  [27:30] The risk of relying on a single metric like NPS. [29:00] Why repeatability is the real measure of success. [31:00] Case study: how fast response times changed customer perception. [34:00] Balancing automation with human connection in customer experience.   [39:00] The future: shifting from volume work to value-driven activities. [41:30] What to expect from Karen’s keynote at FUSION26  Notable Quotes  “Unhappy customers will tell you everything you need to fix it, if you’re willing to hear it” – Karen Mangia  Don’t let your learning lead to knowledge. Let your learning lead to action. – Karen Mangia  Sometimes the best experience is the one the customer doesn’t even notice. It just works”– Karen Mangia  About the Guest  Karen Mangia is the Senior Vice President of Global Customer Success at Bazaarvoice and a recognized leader in customer experience strategy.  With a career spanning more than two decades, Karen has held leadership roles at some of the world’s most influential technology companies, including Cisco, AT&T, and Salesforce, where she built and scaled customer experience and voice-of-the-customer programs at a global level.  In addition to her corporate leadership, Karen is a sought-after keynote speaker and TEDx presenter, recognized for her ability to connect customer experience strategy with real-world execution. She has been named one of the Top 50 Women Leaders of Indiana.  Karen brings a unique blend of research, sales, and operational expertise along with a deep belief that when organizations truly listen to their customers, they unlock powerful opportunities for growth, trust, and long-term success.

EP 51: "You Can't Fall Out of a Basement" with Neil Hart

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.  Key Takeaways  1. Careers aren’t linear – lean into opportunity.  Neil’s path in and out of parking shows that diverse experiences often create the strongest leaders.  2. People, process, and technology are the foundation of great operations. No matter the scale, these three pillars keep everything running.  3. You don’t get thanked in this business – and that’s okay. Success in parking and auxiliary services requires internal motivation, not external validation.  4. Short-term clarity beats long-term guessing.   Neil emphasizes focusing on 2–3-year planning cycles rather than overly rigid 10–15-year forecasts.  5. Leadership is about positioning, not controlling everything. Understanding priorities from both above and below determines where leaders should focus their energy.        Episode Highlights  [02:18] Neil shares how he accidentally entered the parking industry through valet operations. [03:48] Neil leaves the parking industry – and gets pulled back in (twice).        [6:18] The transition to MD Anderson and the stark differences between entertainment parking and healthcare.  [07:48] Expanding into auxiliary services: food, housing, transportation, and more. [10:18] Neil’s return to parking leadership at the University of Houston.                                [18:48] How Neil manages large teams (200+ employees) and complex operations.                [22:18] Neil’s leadership philosophy: listening, prioritizing, and aligning with organizational goals  [29:18] Why long-term planning often fails – and what to do instead.  [31:48] The importance of hybrid operating models in parking and auxiliary services. [36:48] Retirement, reinvention, and joining Reimagined Parking.  [36:48] Neil’s new role and his approach to learning the industry from a national perspective.  Notable Quotes  “Every decision you make today affects years down the road.” – Neil Hart  “I never want to be the smartest person in the room. I want to be surrounded by people who challenge.” – Neil Hart  “You can’t fall out of a basement.”  – Neil Hart   About the Guest  Neil Hart is the Vice President of University Operations at Reimagined Parking, bringing over three decades of leadership experience in parking, healthcare, and higher education.   He has held senior roles at MD Anderson Cancer Center, the University of Texas Medical Branch, and the University of Houston, here he oversaw large-scale parking and auxiliary operations including transportation, food service, housing, and recreation.  Known for his operational expertise and people-first leadership style, Neil is passionate about building strong teams, improving processes, and helping organizations navigate the evolving landscape of parking and mobility.

EP 50: Today, Tomorrow, and Tomorrowland - Keith B. Jones on Integrity, Technology, and the Future of Parking

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 and living by true integrity, navigating 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 ensuring ACE Parking remains a strong pillar of the San Diego and other communities.  Key Takeaways  1. Family businesses are built on responsibility.  Keith reflects on ACE Parking’s origins and the responsibility of leading a business so ingrained in a city’s fabric for generations.  2. Innovation must balance vision with reality. Keith's “Today, Tomorrow, and Tomorrow Land” framework highlights the challenge of deploying technology with benefits today while still preparing for what may come.  3. Technology is only as good as the people behind it. AI may automate operations, but trained humans remain essential to making technology work effectively.  4. Integrity creates long-term stability.Keith emphasizes structural soundness to build organizations that can withstand disruption and continue serving clients.  5. Culture and leadership shape the future of organizations.  Companies must remain nimble, adaptable, and grounded to thrive in the coming future.    Episode Highlights  [02:45] ACE Parking’s origins beginning with a dirt lot to a national mobility company. [06:30] Keith’s first job in parking: directing traffic at an NFL stadium as a child. [10:30] Learning servant leadership while navigating the challenges of joining a family business.[15:00] How ACE evaluates technology partners and the importance of long-term commitment. [18:00] The importance of building a “long road play” organization focused on stability and integrity. [21:00] Early innovations that transformed operations down the road                    [36:00] The “Today, Tomorrow, Tomorrowland” framework [41:00] AI’s impact on parking and how technology must enhance, not replace, the human experience [46:30] What separates companies that will survive the next decade and those that won’t. [53:00] The story behind ACE Parking’s “Park for Pink” program and the personal journey that inspired it.  Notable Quotes  “Integrity to me means structural soundness.” – Keith Jones  “We need to solve the world of tomorrow while pointing toward Tomorrowland.” – Keith Jones  “We’re not in the customer service business – we’re often in the customer service recovery business.” – Keith Jones