40 years in the business. Nearly 2,400 properties sold. Over $24 billion in transactions.

Bob Knakal is a legend in commercial real estate.

But at 63 years old—when most are slowing down—Bob is operating with more energy and drive than ever.

In just the past three years, he’s written multiple books, built a massive presence as a social media business influencer, launched a podcast, started his own brokerage, and even appeared on the Netflix series Owning Manhattan.

So where does that drive come from?

According to Bob—it’s simple: he loves the work.

From his early days as a small-town kid shoveling sidewalks to buy baseball cards (more interested in the stats on the back than the picture on the front), to becoming one of the most data-driven minds in the industry, Bob has always believed that commercial real estate is a business of information.

That mindset helped build his iconic “Knakal Map Room”—a true Mecca of market data that has fueled decades of success.

On this episode of Love in the Land, Austin sits down with Bob to break down the mindset, habits, and philosophy behind a career that continues to evolve. They dive into:

• Why putting clients first is still the ultimate competitive advantage
• How social media has transformed Bob’s business (and how you can use it too)
• Lessons learned from getting fired—and starting over
• What continues to motivate him after $24B in deals

You can follow Bob on LinkedIn, Instagram, and X, and learn more about his work at BobKnakal.com.

If you enjoyed the episode, be sure to like, subscribe, and follow Love in the Land with Austin Love for more conversations with top performers, creators, and business leaders.

Episode #41 – Matt Buder Shapiro

How many “no’s” does it take before you finally hear yes?

For Matt Buder Shapiro, the answer was hundreds.

Matt is the founder of MedPilot, a healthcare technology startup that was eventually acquired by Vytalize Health. Today he serves as Senior Advisor of Marketing & Policy at Vytalize, a company that supports more than 3,000 primary care providers and manages over $3 billion in medical spending. In addition to his work in healthcare, Matt is an active startup investor, backing companies such as Headway, Goodles, and Olipop, along with dozens of other emerging businesses.

But before the growth, the acquisition, and the success… there were constant rejections from investors.

In this episode of Love in the Land, Matt sits down with Austin Love to talk about what it really takes to build a company from scratch, the brutal reality of raising startup capital, and why rejection might be one of the most valuable tools an entrepreneur can have.

Matt also reflects on growing up in Cleveland and his years in Shaker Heights and shares what Machine Gun Kelly was really like in high school.

Topics we explore in this episode include:

• The reality of raising venture capital
• Why most founders hear “no” hundreds of times before a “yes”
• How rejection can become fuel for entrepreneurs
• Lessons from scaling one of the fastest-growing healthcare companies in America
• What Matt looks for when investing in startups
• The future of startups and innovation in Cleveland

Follow Matt on Instagram: @mbudershapiro

If you enjoyed this episode, be sure to like, share, and follow the Love in the Land podcast for more conversations with entrepreneurs, creators, and leaders shaping Cleveland and beyond.

Follow Austin on Instagram: @austinlovetv.

“Cleveland is a world-class city without world-class egos.”

That idea sits at the core of how the Cleveland Cavaliers and Rock Entertainment Group are reshaping Downtown Cleveland with intention, urgency, and alignment.

On this episode of Love in the Land, host Austin Love sits down with Nic Barlage, CEO of the Cleveland Cavaliers and Rock Entertainment Group, and one of the most influential leaders shaping the future of sports, entertainment, and downtown Cleveland.

Nic shares what it means to lead at scale when decisions ripple across an entire city, and why the Cavaliers and Rock Entertainment have made a long-term commitment to investing downtown. From sports and entertainment to real estate and immersive experiences, Nic explains how these platforms are being used not just to host events, but to create daily energy, economic momentum, and lasting impact.

Nic’s path to leadership was anything but linear.

He entered college on a pre-med track, struggled academically, and at one point carried a 1.7 GPA. That moment forced a reset. He took an honest look at what he wanted and realized he could turn his passion for sports into a career.

What followed was rejection.

After applying to more than 170 jobs in sports, Nic finally received his first yes with the Alexandria Beetles of the Northwoods League. The work was unglamorous and behind the scenes, but it shaped the work ethic, humility, and resilience that define his leadership today. That same mindset carried into pivotal moments alongside Dan Gilbert and the Cavaliers, including stepping into difficult roles others avoided, and now guides how Rock Entertainment executes at scale.

In this episode, we explore:

• Rock Entertainment Group and Bedrock’s strategy for accelerating Downtown Cleveland’s evolution

• The Cavaliers’ long-term role as a sports and entertainment anchor downtown

• The competitive, multi-year process behind bringing a WNBA franchise to Cleveland

• How hearing no hundreds of times shaped Nic’s leadership mindset

• Why landing COSM downtown reflects a broader push toward immersive, experience-driven destinations

• What leadership looks like when urgency, alignment, and accountability matter more than ego

This conversation is about more than sports. It is about responsibility, long-term thinking, and what it actually takes to help build a city the right way.

If you enjoyed the episode, be sure to like, follow, and subscribe to Love in the Land on Spotify and Apple Podcasts.