Local Legends with Jess: Arizona Edition

Jessica Benevento
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Local Legends: Arizona Edition is a podcast that shines a spotlight on the incredible individuals making waves across the Grand Canyon State. Hosted by a passionate local connector and community advocate, each episode features candid, heartfelt, and often humorous conversations with Arizona’s most inspiring entrepreneurs, nonprofit leaders, creatives, and community changemakers. From real estate rockstars to nonprofit heroes, magicians to mentors—we’re bringing you the stories that make Arizona legendary. Tune in to be inspired, entertained, and reminded of the power of local connection.

  1. Love Doesn’t End: Understanding Grief with a Death Doula

    6D AGO

    Love Doesn’t End: Understanding Grief with a Death Doula

    This week Jess sits down with a guest whose story leaves a lasting impression. Margaret Anderson shares the deeply personal journey that led her to the work she does today—helping others through grief, loss, and the emotional process surrounding death. Margaret’s story begins with unimaginable loss after the passing of her son. In the midst of her own grief, she began to see how powerful meaningful support can be during life’s most difficult moments. That realization led her to begin working in hospital transportation services, where she spent nearly ten years helping patients and families during vulnerable times. Through that work, she witnessed firsthand how important compassion, presence, and understanding can be when people are facing the unknown. Eventually Margaret felt called to support others in a deeper way. She enrolled in a course that would change her life and became a death doula, someone who helps individuals and families emotionally and spiritually prepare for the end-of-life journey. Today she also works as a grief educator, guiding caregivers and families through the complicated emotions that come with loss. During the conversation, Margaret explains that grief is not something to “fix,” but something to move through. Her work focuses on helping people process emotions, find closure, and create space for the conversations that often go unspoken. She shares stories of clients learning to say the things that matter most—expressing love, forgiveness, gratitude, and goodbyes that bring peace to both sides. Margaret also reminds listeners that while death is something many people avoid talking about, it is a natural part of life. By acknowledging it openly, families can reduce fear, strengthen connections, and allow healing to begin. Her message is simple but powerful: grief work helps people realize that love does not disappear with loss—it simply changes form. This moving episode invites listeners to look at grief through a different lens and offers a compassionate reminder that even in life’s hardest moments, support, understanding, and connection can make all the difference. These are the local legends shaping our communities. Real stories, real talk, and powerful conversations. Local Legends with Jess — where Arizona’s stories connect.

    18 min
  2. Jaclyn Tromo — From Makeup Artist to Personal Branding Powerhouse

    MAR 12

    Jaclyn Tromo — From Makeup Artist to Personal Branding Powerhouse

    The inspiration level jumps fast in this episode featuring entrepreneur Jaclyn Tromo. From the moment Jess discovered Jaclyn on social media, she was captivated. One connection quickly turned into a yes to the opportunity Jaclyn was promoting — proving that sometimes success simply starts with taking action. Jaclyn’s entrepreneurial spirit started young. At just five years old she wanted a cash register because she knew she wanted to work and run a business. After moving to Arizona at age ten, her creative path eventually led her to esthetician school and into the beauty industry. She assisted as a makeup artist at Arizona Fashion Week and soon began working with models and brides, building real experience behind the scenes. With a bigger vision in mind, Jaclyn took a bold risk and moved to Los Angeles to grow a makeup brand. Without a steady job, she took on odd work while building her dream. At one point she found herself staring at a $100,000 production bill while developing her cosmetics line — a moment that could have stopped everything. Instead, it became part of the story that pushed her forward. What started as a beauty career eventually evolved into something even bigger than she imagined. Jaclyn discovered her true superpower — helping entrepreneurs launch fast. Today she runs a thriving personal branding agency, coaches business owners, and is teaching industry leaders how to build authority-driven digital personal brands.  Her journey is proof that when you keep showing up, take risks, and stay open to new opportunities, the path can grow into something far greater than you ever expected. This episode will leave you inspired to act on your vision and see what can change in a blink of an eye.   These are the local legends shaping our communities. Real stories, real talk, and powerful conversations. Local Legends with Jess — where Arizona’s stories connect.

    30 min
  3. From Fairways to Film to Finance and More: The Evolution of Craig Matthew

    MAR 5

    From Fairways to Film to Finance and More: The Evolution of Craig Matthew

    In this episode of Local Legends with Jess, meet Craig Matthew — a dynamic leader whose journey spans elite athletics, music, entrepreneurship, film, and now finance. Craig made history at The Ohio State University as the first golfer to earn both Athletic All-American and Academic All-American honors in consecutive years. He went on to compete professionally, becoming a champion on the PGA Tour’s Mackenzie Tour and winning the Canadian Amateur Championship. Jess dives into what it truly means to be an All-American — the discipline, emotional control, daily routines, and mindset that separate good from great, on and off the course. But Craig’s story doesn’t stop with golf. Music has always been woven into his life. A self-taught guitarist inspired by his father and close friends, early jam sessions planted the seed for something bigger. After stepping away from professional golf at 37, a key connection led to recording original music and music videos.  Craig has owned and operated several coffee shops, expanded into creative projects, and stepped into acting in multiple independent films. He also serves on the Board of Directors for Movies Making A Difference, a nonprofit producing feature films that raise awareness and funds to combat human trafficking and support survivors. From championship golf to creative arts, business ownership, philanthropy, and now finance, Craig’s path reflects adaptability, courage, reinvention, and the willingness to evolve without losing his core identity. Golf. Music. Coffee. Film. Charity. Finance. What’s next for Craig Matthew? Tune in to hear how passion, discipline, and purpose continue to shape every chapter of his journey. These are the local legends shaping our communities. Real stories, real talk, and powerful conversations. Local Legends with Jess — where Arizona’s stories connect.

    24 min
  4. The Original Legend Herself: Jess The Mortgage Matchmaker - Buying a Home is Easier Than You Think

    FEB 26

    The Original Legend Herself: Jess The Mortgage Matchmaker - Buying a Home is Easier Than You Think

    In this special episode of Local Legends with Jess, the spotlight turns to the original legend herself — Jess, the Mortgage Matchmaker. From start to finish, this conversation centers around one powerful message: buying a home doesn’t have to be overwhelming, confusing, or out of reach. Jess breaks down common misconceptions about the mortgage process — especially the belief that you need more money, perfect timing, or flawless circumstances before starting. She explains why waiting often creates more uncertainty than clarity and how getting informed is the real first step toward homeownership. With years of experience helping individuals and families navigate the lending world, Jess shares how strategy, preparation, and the right guidance can make all the difference. Behind every mortgage is a real story — a family, a fresh start, an investment in the future — and her mission is to make that process feel clear and achievable. If you’ve ever wondered whether now is the right time, this episode will challenge you to rethink the narrative. The path may be more accessible than you realize — and the first move might simply be starting the conversation. These are the local legends shaping our communities. Real stories, real talk, and powerful conversations. Local Legends with Jess — where Arizona’s stories connect.

    4 min
  5. From Service to Sold — Building a Real Estate Legacy Together

    FEB 19

    From Service to Sold — Building a Real Estate Legacy Together

    Ryan & Whitney Cole officially join the Local Legends lineup, and their story is one built on grit, heart, and lived experience. This husband-and-wife real estate team didn’t start in property — they started in people. Whitney’s background in social work and as a correctional officer gave her a front-row seat to the realities families face during their hardest seasons. Supporting others through instability and crisis shaped her compassion, resilience, and deep understanding of what “home” truly means. Once she became a mom, her priorities shifted — and real estate became the natural next chapter where she could continue serving families, just in a different way. Ryan’s journey began in the banking world, originally from Texas, bringing with him a strong work ethic and undeniable go-get-it attitude. Along the way, he experienced professional wins and hard lessons — including losses that tested him. But instead of backing down, Ryan leaned in. After experiencing burnout, he made a bold move: diving headfirst into a crash course in real estate. That decision changed everything — and he never looked back. At the foundation of Ryan & Whitney’s business is one core value: relationship first. They understand that buying or selling a home isn’t just a transaction — it’s emotional, personal, and sometimes overwhelming. Because they’ve navigated challenges themselves, they lead with empathy, strategy, and calm confidence. They believe every situation has a solution, and they show up determined to make the process not only successful, but supportive. In this episode of Local Legends with Jess, get to know the real story behind this dynamic duo — the lessons that shaped them, the risks they took, and why their clients feel more like family. Ryan & Whiney don’t just sell homes. They build trust, create stability, and stand beside their clients every step of the way. This is what legendary looks like. These are the local legends shaping our communities. Real stories, real talk, and powerful conversations. Local Legends with Jess — where Arizona’s stories connect.

    21 min
  6. Flipping the Script: Jess is in the Hot Seat the OG Local Legend Mortgage Matchmaker and Husband Jason

    FEB 12

    Flipping the Script: Jess is in the Hot Seat the OG Local Legend Mortgage Matchmaker and Husband Jason

    In this episode of Local Legends with Jess, the roles reverse—and Jess takes the hot seat. Jason, a seasoned mortgage professional with over 25 years in the industry, steps in as interviewer to have a candid, thoughtful conversation with the original Local Legend herself. Known as a true connector and rainmaker, Jess opens up about what it really took to grow into the industry—admitting it took nearly two years to fully find her rhythm in a competitive space. Jason brings forward four powerful questions for Jess —from what you’re truly comfortable paying, to what it means to offer the best deal while staying dedicated to the client’s long-term best interest. Together, they unpack authenticity in business, client-first decision making, and why caring about the long-term investment matters more than chasing quick wins. This episode is honest, insightful, and refreshingly real—perfect for anyone navigating the mortgage world, considering homeownership, or wanting a behind-the-scenes look at how integrity and trust shape lasting success. Pull up a seat—this is one conversation worth listening to. These are the local legends shaping our communities. Real stories, real talk, and powerful conversations. Local Legends with Jess — where Arizona’s stories connect.

    23 min
  7. Jess and Jason Living the Dream While Showing Up for Family

    FEB 5

    Jess and Jason Living the Dream While Showing Up for Family

    In this special and personal episode, Jess sits down with her husband, Jason—her favorite human, the love of her life, and the one person she can love hard and challenge hard all within minutes. What starts as a conversation about dreams quickly unfolds into a real, unfiltered discussion about marriage, purpose, responsibility, and the unexpected turns life brings. Together, they explore what it really means to live the dream. Sharing your talents with the world matters—but so does providing for your family, staying grounded, and navigating the tension between passion and responsibility. This episode dives into that balance, offering honest insight, laughter, and perspective that many couples quietly wrestle with. If you’ve ever wondered how to pursue your calling without losing sight of the people who matter most, this conversation will resonate deeply. In this episode, you’ll hear about: Loving hard, challenging each other, and growing togetherTurning dreams into reality while staying responsibleWhy sharing your talents is essential—but not the whole pictureFinding balance between passion, purpose, and providingThe real conversations couples don’t always have out loudThis episode is a reminder that living the dream doesn’t have to be all or nothing—and the solution might be closer than you think. These are the local legends shaping our communities. Real stories, real talk, and powerful conversations. Local Legends with Jess — where Arizona’s stories connect.

    24 min
  8. Local Legends with Jessica Benevento Episode: Pop — AKA Truman, AKA Poppy Chuloo (Yes… THAT Pop)

    JAN 29

    Local Legends with Jessica Benevento Episode: Pop — AKA Truman, AKA Poppy Chuloo (Yes… THAT Pop)

    Meet Pop, also known as Truman and lovingly referred to as Poppy Chuloo—a retired college football coach, self-proclaimed True National Legend, and full-time Arizona snowbird who has officially mastered the art of saying whatever he wants… because he can. Pop lives by one very simple rule:  👉 If you’re a 7 or lower, you’re not worth his time. Dead serious. Zero apologies. In this episode, Jessica Benevento (Arizona’s Mortgage Matchmaker) sits down with Pop for a conversation that’s equal parts legendary, unfiltered, and laugh-out-loud entertaining. From old-school coaching wisdom to life lessons only earned through decades of wins, losses, and locker room talks—Pop brings stories you won’t hear anywhere else. And just when you think it can’t get better…  Pop shows up to the studio convinced he’s being arrested—only to realize he’s actually there to record a podcast. Classic Pop. This episode is packed with:  🏈 Coaching stories from a true football lifer  😂 Unfiltered opinions you may or may not agree with  🌵 Snowbird life in Arizona  🔥 Legendary confidence (borderline unbelievable)  🎧 A guest you’ll never forget Whether you love him, question him, or laugh the entire way through—Pop is a Local Legend in every sense of the word. 👉 Hit play and decide for yourself…  Are you a 7 or higher? These are the local legends shaping our communities. Real stories, real talk, and powerful conversations. Local Legends with Jess — where Arizona’s stories connect.

    25 min
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About

Local Legends: Arizona Edition is a podcast that shines a spotlight on the incredible individuals making waves across the Grand Canyon State. Hosted by a passionate local connector and community advocate, each episode features candid, heartfelt, and often humorous conversations with Arizona’s most inspiring entrepreneurs, nonprofit leaders, creatives, and community changemakers. From real estate rockstars to nonprofit heroes, magicians to mentors—we’re bringing you the stories that make Arizona legendary. Tune in to be inspired, entertained, and reminded of the power of local connection.

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