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.

Episode #39 — Bernie Garrah: How to Win With Your Money in 2026

In this episode of Love in the Land, Austin Love sits down with Bernie Garrah, Principal and Wealth Advisor at Tempo Wealth, for a grounded, real-world conversation about money, freedom, and how to think differently about your finances in 2026.

With nearly 30 years in financial planning and wealth management, Bernie shares what he’s learned building a career and a life, around fully integrated financial planning with a family-office mindset. From making just $8,000 a year early on to betting on himself with an “eat what you kill” mentality, Bernie breaks down the realities of entrepreneurship, delayed gratification, and why financial independence often comes at a cost before it becomes a benefit.

This episode explores:

• Why money is one of the most important tools in our lives — yet rarely taught properly

• How to rethink your relationship with money, not just your investments

• Key financial trends and mindset shifts to pay attention to in 2026

• The freedom (and pressure) that comes with being your own boss

• Long-term thinking vs. short-term wins when building real wealth

Whether you’re an entrepreneur, high-earner, or someone who feels successful on paper but uncertain financially, this conversation will help you zoom out, gain perspective, and start positioning your money with more intention.

You can find more information on Bernie and Tempo here: Tempo Wealth - Wealth Management for Modern Professionals

This episode is for educational and informational purposes only and is not intended as personalized investment advice.

Love in the Land — Adam Graves (Nestlé, DiGiorno, Hot Pockets, CPK, Tombstone)

From marketing intern to President of a $2B food empire.

On this episode of the Love in the Land Podcast, Austin Love sits down with Adam Graves, President of Pizza & Snacking at Nestlé USA, the division behind some of the biggest food brands in the world — DiGiorno, California Pizza Kitchen, Tombstone, Jack’s, Hot Pockets, and Stouffer’s Bites.

Adam has spent nearly two decades inside Nestlé, rising from an intern to leading one of the company’s most iconic and innovative portfolios. In this conversation, he takes us inside the machine of global food brands — how new products like DiGiorno’s wood-fired pizza are conceived, engineered, tested, marketed, and scaled across millions of households.

We also go deeper into:

• What it takes to lead inside a Fortune 500 company

• How Nestlé builds and protects billion-dollar brands

• Developing a growth mindset inside a massive organization

• Encouraging entrepreneurship inside corporate America

• And what Adam has learned from international leadership roles around the world

This episode is a must-listen for anyone interested in food, branding, consumer products, leadership, or building a career inside a global company.

Follow Adam Graves on LinkedIn for more insights into leadership and brand building.
And don’t forget to follow and rate Love in the Land for more conversations with the people shaping business, culture, and the future.

🎧 Hosted by Austin Love — @AustinLoveTV

Today on the podcast, Charles Oakley joins the show.
A Cleveland native and former NBA All-Star, Oakley reflects on growing up in Cleveland, his unlikely path to the NBA, his legendary friendship with Michael Jordan, and his complex relationship with the New York Knicks. We also talk about life beyond basketball, including his work as a philanthropist, chef, author, and his new sports prediction app, Predict5.

Follow Charles on social media @therealoak34

Love in the Land Podcast | Episode #36: Matt Kaulig — Betting Big, Building Bigger

On this episode of Love in the Land, we welcome our first BILLIONAIRE guest, Matt Kaulig — an entrepreneur, philanthropist, former college athlete, founder of LeafFilter, minority owner of the Cleveland Guardians, NASCAR team owner, and one of Northeast Ohio’s most dynamic business leaders.

With ownership in more than 70 companies, Matt Kaulig’s story is one of relentless drive, bold decisions, and unwavering self-belief.

In this conversation, Matt opens up about:

• How he broke into the “old boys club” of car racing from sponsor to NASCAR team owner

• The leap of faith that led him to quit his job and launch LeafFilter from his basement

• Why betting on yourself, even during the 2008 financial crisis, can be the key to explosive growth

Matt’s journey is a masterclass in vision, risk, and resilience — a reminder that success favors those who go all in.

Follow Matt Kaulig and Kaulig Companies on social media to keep up with their growing impact.
And if you enjoyed this episode, don’t forget to like, share, and subscribe to Love in the Land for more stories celebrating bold moves and big hearts right here in Cleveland.

Love in the Land with Austin Love – Featuring Bridget Linton

On this episode of Love in the Land, Austin Love welcomes Bridget Linton, a familiar face and voice to Cleveland sports fans. Bridget is best known as the in-game host for the Cleveland Browns, but her story goes far beyond the sidelines. She’s a seasoned media personality, accomplished Irish dancer, former Miss Ohio Teen USA, spokesperson, influencer, and all-around champion of all things Cleveland.

Bridget sits down with Austin to share her journey through the media world, from TV to radio and ultimately to becoming the high-energy presence inside Huntington Bank Stadium on game day. She pulls back the curtain on what it takes to deliver a world-class fan experience on Sundays, why she’s proud to call Cleveland home, and even bonds with Austin over their shared love of local dive bars.

It’s a fun, insightful conversation you won’t want to miss.

Follow Bridget online at @bridget_linton8, and don’t forget to like, follow, and subscribe for more Love in the Land!

On this episode of the Love in the Land Podcast with Austin Love we’re thrilled to welcome TV executive Adam Miller.  Adam is currently the Vice President of On‑Air Talent Strategy at TEGNA and a former Senior Producer for TODAY. A seasoned veteran of the news industry, Adam’s career began right here in Northeast Ohio, where he knew from an early age that television news production was his calling. Adam is a proud alumnus of the Medill School of Journalism at Northwestern University .

After sharpening his skills in journalism, he started at TODAY at the ground level and rose through the ranks to become a senior producer. From there, he took on leadership as News Director at WKYC in Cleveland and then advanced to his current role overseeing on‑air talent strategy across TEGNA’s nationwide stations.

In this episode, Austin sits down with Adam to explore his journey, his vision for the future of television journalism, and how he now shapes the industry by recruiting the next generation of on-air talent. Adam shares what he looks for in journalists—and reveals what he believes gives a personality that elusive “it” factor. He also recounts his entertaining and unforgettable 2016 World Series adventure with the legendary Al Roker. And as a fun bonus, the two team up to build their very own “Mount Rushmore” of favorite TV journalists.

Enjoy this fun and insightful conversation on Love in the Land. Don’t forget to connect with Adam on LinkedIn or follow him on Instagram at @AmintheAm—and be sure to like, subscribe, and share for more!

On this week’s episode of Love in the Land with Austin Love — Michael Allio!

You may know Michael as “Michael A.” from The Bachelorette Season 17 and Bachelor in Paradise Season 8. But beyond reality TV, Michael is a devoted father, entrepreneur, philanthropist, influencer, and proud Akron native.

In this episode, Michael sits down with Austin to open up about life, new love, his growing medical venture, Saint James Therapeutics, and what it’s like living the dad life in Akron. He also shares how he found himself on national TV searching for love — and how he’s now working to reclaim his last name!

Plus, you’ll hear how Austin and Michael bonded over The Notorious B.I.G. and the B-52s at a wedding — and so much more.

We hope you enjoy this candid, hour-long conversation with Michael Allio. To keep up with Michael, follow him on Instagram at @michael_alliol4. And as always, don’t forget to like, follow, and share The Love in the Land Podcast. You can follow Austin at @austinlovetv. Cheers!

Today on The Love in the Land Podcast with Austin Love: singer, songwriter, and smooth crooner Hayden Grove!

Fresh off his appearance on NBC’s The Voice as a member of Team Adam, Hayden is no stranger to the spotlight. Before hitting the national stage, he was a familiar face in Cleveland—both as a sports reporter for Cleveland.com and as a regular on the local music scene.

In this episode, Austin sits down with Hayden to talk about his bold leap from a steady job in media to fully pursuing his passion for music. Hayden opens up about his experience on The Voice, shares behind-the-scenes moments from the show, and reflects on a time he walked away from singing altogether—only to rediscover his love for it.

Huge thanks to Hayden for joining the show. Stay connected with everything he’s doing (or even book him for your next event!) at haydenfrankgrove.com. Enjoy the episode!