In this episode of Keep Hustling, host Aaron Gordon welcomes guest Coleman Flentge, who shares his inspirational journey from a small town in Kentucky to building a career and business centered around music. Coleman Flentge discusses the impact of his mother's unwavering hustle and how her sacrifices shaped his own determination and drive. He recalls overcoming early discouragement and finding his passion for music, eventually moving to Florida to pursue his dreams and earning a master's degree in music education. Together, Aaron Gordon and Coleman Flentge explore the transformative power of music, how it connects people, heals, and helps individuals express themselves, whether alone or in a community. They emphasize that making and enjoying music is a deeply personal, freeing experience not limited by talent. The episode closes with reflections on creativity, mindfulness, and an inspiring Mark Twain quote about living fully. If you're looking for motivation to follow your passion and appreciate the everyday hustle, this episode delivers powerful insights and heartfelt stories.

Get To Know Coleman Flentge Coleman Flentge is a native of Kentucky who moved to Tampa, Florida, in 2014 to attend the University of Tampa (UT). At UT, Coleman studied conducting. He was the assistant conductor for the Men's Glee Club and Chamber Singers. He was recognized by the UT faculty for his academic achievements, becoming the department tutor for Music Theory and History. He graduated with a Bachelor of Arts Degree in Music Education in 2017.

Coleman began his career as a music educator in Plant City, where he was the music teacher at Walden Lake Elementary from 2017 to 2021. While there, Coleman developed an enriching musical experience for his students by supervising an excellent, rigorous general music program and conducting a multi-voice chorus and a ukulele ensemble.

In 2019, Coleman was given the honor of leading the 150 voices of the East Chorus for the Hillsborough County Fine Arts Festival.

In 2020, he received the Ida S. Baker Diversity Educator of the Year Award for bringing his passion for inclusion into all his classes.

Since 2018, Coleman has served as the Associate Director of Music at St. Andrew's Episcopal Church-Tampa under the direction of Dr. Ryan Hebert. At St. Andrew's, Coleman conducts the adult choir, two children's choirs, and a professional handbell ensemble.

A graduate of the Summer Master of Music Education (Choral Conducting) program from Florida State University, Coleman has conducted a variety of choral pieces from all eras of music, which he believes has helped him refine effective rehearsal strategies.

Coleman is the Music Facilitator at Dr. Kiran C. Patel High School in Temple Terrace. Since the inaugural year for a music program at Patel, Coleman has built and cultivated a distinctive program offering options for every learner interested in pursuing the Musical Arts. He is currently teaching two choruses, an orchestra, guitar, and music theory. The program has blossomed into a rich, meaningful music experience for all its participants.

As the Artistic Director for the PCC Chorale, for a third season, Coleman is enthusiastically continuing development of the group's musical excellence. Coleman firmly believes that music performance should be an experience that brings people together, unifying us through the art and genius of music. Coleman is doing his part to nurture the singers' vocal skills and enrich their lives while leading them toward new musical frontiers.

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3 Episode Key Takeaways

1. Hustle Inspired by Upbringing: Coleman Flentge shares how his drive to succeed originates from witnessing his mother's relentless determination to provide for her family against all odds. This highlights how early-life experiences and unsung acts of perseverance from loved ones can deeply shape our motivations and define how we approach our own hustle.

2. The Transformative Power of Music: The episode explores music's unique ability to heal, energize, and connect people—regardless of skill level or background. Both Aaron Gordon and Coleman Flentge discuss how music serves not only those who listen but especially those who create it, illustrating that authentic self-expression through music can bring profound personal fulfillment and communal bonding.

3. Creativity as Presence and Healing: Coleman Flentge emphasizes the importance of reconnecting with creativity as a path to mindfulness, personal growth, and resilience. By leaving his classroom teaching career to pursue a venture centered on fostering creativity and presence, he demonstrates that stepping beyond comfort zones and nurturing one's creative spirit can spark entrepreneurial empowerment and help navigate life's biggest transitions.

Show Overview 00:00 Gratitude for Coleman 03:31 Driven Passion Fuels Musical Journey 08:38 Resilience and Lifelong Inspiration 12:31 Transformative Power of Music 15:00 Music: Innate to Humanity 16:52 Music as Soul's Expression 23:06 Transformative Power of Music 25:40 The Timeless Power of Music 27:23 Fear of Life and Death

On this episode of Keep Hustling, host Aaron Gordon welcomes entrepreneur and author Katie Smetherman Holmes for a deep dive into purpose-driven entrepreneurship. Katie shares how her early search for meaningful work led her to a rewarding career in graphic design, despite doubts from others, and how passion and identity fuel lasting professional success. The conversation explores the connection between personal drive and business identity, and Katie offers advice for anyone struggling to find or act on their purpose, emphasizing the importance of taking small steps and being vulnerable. The episode also highlights the necessity of authentic storytelling in a commoditized marketplace, building genuine connections with clients and teams, and embracing your unique story. Katie closes with inspiration from her late mother: "You can do anything you set your mind to," reminding listeners to persevere and keep hustling through doubts and tough days. Don't miss this candid conversation packed with actionable insights for finding your passion and making it the core of your professional life.

Get To Know Katie Smetherman Holmes Katie is an award-winning designer, brand strategist, and international bestselling author. As Founder and CEO of Brand Studio Creative, she works passionately, efficiently, and strategically on international clients of all sizes, no matter the industry. Katie also provides her clients with exceptional brand coaching while providing brand strategy and design services to ensure each client feels empowered, focused, and consistent within their own marketing.

Katie has experience (but is not limited to) in these industries: Marketing Agencies, Publication Houses, Energy, Oil and Gas, Electrical, Small Boutiques, Business Coaches, Product Entrepreneurs, Legal Services, Data Management Companies, App Development Companies, Event and Conferences, Spiritual Coaches, Construction Companies, AND MANY MORE!

Katie is a master in Brand Management and Communication, with a background in graphic communication, design, and Art History. She utilizes these teachings in her work every day to bring each design piece new life and energy.

In her international bestseller, Ignite Your Wisdom, Katie shared her story of why she started her own business to shed light on entrepreneurship, passion, and dedication to her goals.

Limitless Leadership is her most recent bestselling publication. This anthology is for women ready to stop playing small and rise into their full, God-given potential. This powerful collection brings together visionary women who have shattered self-doubt and redefined success on their own terms.

You can find all her books on the Brand Studio Creative website.

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3 Episode Key Takeaways

1.Define Your Purpose: Katie Smetherman Holmes shares how finding personal meaning was the cornerstone of her success. Her journey from uncertainty about her major to building a thriving six-figure creative business underscores the importance of aligning your career with the passions and values that drive you.

2. Take the Leap—One Step at a Time: Both Aaron Gordon and Katie Smetherman Holmes agree that fear often holds people back from pursuing their true purpose. The episode highlights that even small steps toward your goal matter—whether it's side hustling, planning, or simply voicing your dreams. Progress is fueled by starting, no matter how small.

3.. Authenticity Builds Connection: Katie Smetherman Holmes stresses that genuine storytelling is the key to resonant brands and lasting relationships—even in a commoditized, digital-first world. By being vulnerable and sharing both victories and struggles, individuals and businesses foster trust, loyalty, and community that set them apart from competitors.

Show Overview 00:00 Seeking Purpose in Work

04:32 Choosing Art Over Engineering

07:59 Finding Purpose Through Vulnerability

09:56 Chasing Passion and Purpose

13:41 Authenticity Connects in AI Era

17:05 Prioritizing Human Connection at Work

22:49 Embrace Vulnerability in Hustle

23:41 Perseverance and Determination

In this episode, Aaron Gordon welcomes Monica McKitterick, nurse practitioner and entrepreneur, to share her journey of pivoting from traditional medicine to pioneering membership-based primary care. Starting with dreams of becoming a pediatric oncologist, Monica McKitterick describes how her upbringing instilled resilience and a drive to excel, traits that guided her through major career transitions. Realizing the burnout of conventional healthcare, she launched her own direct primary care practice, prioritizing patient relationships, affordable access, and personal time over profit. Monica discusses the challenges of entrepreneurship, the power of delegation, and her vision for sustainable healthcare outside insurance constraints. She emphasizes the fundamental elements of health, nutrition, physical activity, sleep, and stress management, and advocates for prioritizing well-being as the cornerstone of success. Monica's next chapter centers on educating other providers to adopt direct care models, amplifying positive change. The episode closes with Monica's motivational mantra: "Someone else's opinion of you is none of your business", an inspiring reminder for anyone on their own hustle journey.

Get To Know Monica McKitterick, FNP Monica McKitterick is a dedicated Family Nurse Practitioner and the visionary CEO of Impact Family Wellness, a pioneering provider of Direct Primary Care (DPC) in the Austin area, with locations in Liberty Hill and Cedar Park. Under her leadership, the organization has flourished, serving a growing patient base of 1,800 individuals with a commitment to redefining primary care. Monica's innovative approach emphasizes same-day or next-day access, direct communication with providers, and transparent pricing that significantly benefits both patients and employers.

As the founder of The DPC Formula, Monica empowers healthcare clinicians to successfully launch and scale their own DPC clinics. Her expertise is encapsulated in her book, "DPC: Dream Job or Total Disaster," and complemented by the development of "The DPC Launch Kit" e-course, which provides a straightforward roadmap for aspiring clinic owners.

Monica is passionate about enhancing the landscape of healthcare. She helps employers by offering membership primary care tailored for teams in Central Texas, designing and rolling out onsite and near-site clinics, and implementing cost-control strategies that prioritize primary care and reduce avoidable claims.

For fellow clinicians, she offers a comprehensive startup roadmap that includes guidance on pricing, contracts, Medicare opt-out processes, vendor selection, marketing strategies, employer partnerships, and operational protocols aimed at preserving margins while enhancing the patient experience.

With her expertise, dedication, and innovative mindset, Monica McKitterick-Smith is reshaping the future of primary care, creating a healthier and more sustainable healthcare system for both providers and patients.

3 Episode Key Takeaways 1. Redefine Success on Your Own Terms: Monica McKitterick shares how her family's expectations and early pursuit of an "impressive" career led to burnout and unhappiness. Her evolution from aspiring pediatric oncologist to nurse practitioner to entrepreneur highlights the importance of letting go of external validation and crafting a success story that is true to yourself.

2. Embrace Strategic Delegation: One of the biggest hacks for sane, balanced hustle? Delegation. Monica McKitterick reveals that learning to relinquish control and outsource tasks—both professionally (office work, marketing, cleaning) and personally—is a crucial shift that distinguishes true entrepreneurs from perpetual employees.

3. Choose Time Over Money: In launching a membership-based primary care clinic and letting go of traditional insurance models, Monica described how reclaiming her time was more valuable than chasing a higher income. "I'm motivated by my time. I would much rather be home in time for dinner than take home $400,000 a year."

Show Overview 04:24 The Drive to Pivot

07:06 Seasons, Hustle, and Healthcare Change

12:29 Dream Delegation for Long-Term Vision

15:59 Nurse Practitioners vs. Physicians

18:05 Nurse Practitioner Limits Discussed

20:47 Healthcare Access for the Uninsured

23:00 Promoting Direct Primary Care

26:48 Focus on You, Not Others

In this episode, Aaron Gordon welcomes entrepreneur Jermane Cheathem for a candid discussion about overcoming adversity, building resilience, and simplifying success. Jermane shares his remarkable journey, moving 18 times by age seven, being abandoned twice, and how those challenges shaped his mindset and business approach. Together, they explore why complexity in business and life is often self-imposed, and how focusing on leverage, efficiency, and eliminating busywork leads to more freedom and fulfillment. Jermane offers actionable mindset shifts to break out of the survival grind and emphasizes the power of simplicity, confidence, and iteration. The episode closes with inspiring advice: treat life as an adventure and keep hustling to chase your dreams.

Get To Know Jermane Cheathem Jermane Cheathem empowers entrepreneurs to achieve six-figure success. His remarkable journey from a challenging childhood to generating over $50 million in sales in the finance industry is a testament to resilience and vision. Overcoming early adversity, Jermane discovered the transformative Connector model, which allows individuals to capitalize on their networks for significant financial gain without the need for extensive investment or traditional hustle.

As a mentor, Jermane shares his Insider's Playbook, guiding B2B professionals in building six-figure side businesses in their spare time. He champions the idea of leverage over grind, empowering others to reclaim their narratives and pursue entrepreneurship.

Jermane is a cheat code that can help you unlock your potential and create a profitable, fulfilling business.

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3 Episode Key Takeaways 1. Simplify for Success: Jermane Cheathem's journey illustrates that both life and business are fundamentally simple—even if they're not always easy. By identifying and focusing relentlessly on the single most impactful activity (his lead domino), Jermane demonstrates how cutting out unnecessary complexity leads to greater productivity, profitability, and personal freedom.

2. Leverage Relationships: Instead of chasing individual sales, Jermane found exponential growth by partnering with strategic referrers—those already trusted by his target clients. His approach highlights the power of building networks and leveraging third-party trust to scale efficiently, showing that real leverage comes from aligning yourself with the right people and channels rather than trying to do everything solo.

3. Mindset Over Grind: Jermane's story proves that escaping the survival grind requires a deep mindset shift. By zooming out and reframing daily challenges in the grand scheme of life, he advocates for focusing on fulfillment and freedom over endless busyness. His perspective urges listeners to eliminate unnecessary tasks, let go of fear-driven busyness, and prioritize what truly matters—ultimately leading to more joy and less stress.

Show Overview

00:00 Embracing Change Fuels Growth 03:21 Resilience Shapes Life's Success 07:03 Success Demands Relentless Effort 10:44 Leveraging Efficiency for Happiness 13:53 Confidence Fuels Productivity16:59 Optimize Time, Minimize Waste 23:04 Persistence Over Perfection 24:30 Simplicity Fuels Happiness and Success

On this episode of Keep Hustling, host Aaron Gordon sits down with Jevon Gondwe, a three-time NCAA soccer champion and leadership development expert. Jevon discusses how a love for competition and the power of mentorship propelled him to athletic and professional success. He shares lessons on the importance of team culture, personal growth, and how leaders can inspire buy-in and engagement. Jevon also unpacks his "Culture of Champions" framework, explaining why developing personal growth habits is crucial for effective leadership. The episode wraps with Jevon's motivational advice: set bold dreams that push you to become your best self. If you're looking for fundamental strategies to elevate your hustle and leadership, this conversation is a must-listen.

Get To Know Jevon Gondwe Jevon Gondwe, a distinguished Leadership Transformation Architect, is the founder of a transformative movement dedicated to Building a Culture of Champions. As a 3x NCAA National Champion and an Inc. Magazine contributor, Jevon leverages his extensive expertise to empower leaders to foster high-performing, psychologically safe teams that thrive in the dynamic landscape of the new economy. His proprietary framework, Building a Culture of Champions, equips people leaders with a strategic edge to transform disengagement and conflict into catalysts for growth. By harnessing the mindset and leadership principles of elite athletic teams, he enables organizations to cultivate environments where teams consistently excel, driving sustainable success in today's fast-evolving business world. Jevon recognizes the critical need for organizations to adapt to the rapid pace of technological advancements. He warns that without fostering continuous learning and growth, businesses risk losing top talent to disengagement or turnover. Drawing from his extensive experience, Jevon has witnessed the hidden costs of a disengaged workforce, the uncertainty fueled by technological change, and the urgent need to rebuild culture in the post-pandemic era. His insights provide a wake-up call for leaders to create the future they envision. As a sought-after thought leader, Jevon's insights resonate across prominent platforms such as Inc. Magazine and Training Industry. With partnerships spanning universities, state governments, and both private and public organizations, he brings a wealth of practical knowledge earned through over 10,000 hours of mastery. Having delivered more than 500 dynamic presentations and trained over 30,000 professionals across seven industries, Jevon's expertise is grounded in real-world impact. His most requested speaking topics include Building a Culture of Champions, Maximizing Leadership through Personal Growth, Influential Communication Skills for the New Economy, and Transferring Leadership Skills from Elite Sports Teams to Business. Jevon Gondwe is a catalyst for transformation, empowering leaders to unlock their potential and build thriving, resilient organizations ready for the challenges of tomorrow.

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3 Episode Key Takeaways 1. The Power of Belief and Teamwork: Jevon Gondwe highlights how crucial it is to have someone who believes in you, whether it's a coach or a teammate. His NCAA soccer journey showcases that true achievement is unlocked not just through personal drive, but when you're surrounded by people who support, challenge, and push you to be your best. Success becomes possible when your growth is tied to the collective vision of a team.

2. Personal Growth Fuels Leadership: Jevon stresses that effective team leaders must first focus on their own personal development. The episode reveals that habits like reading, reflection, and intentional learning aren't selfish—they're the foundation of authentic leadership. By continuously growing themselves, leaders create a culture that uplifts and inspires everyone around them. 3. Build Buy-In Through Vision and Listening: One major insight from Jevon's "Culture of Champions" framework is the importance of listening and understanding each team member's unique role and ambition. Leaders can spark engagement and genuine buy-in when they prioritize open conversations, value each person's vision, and help individuals see where they fit within the bigger picture. Teams thrive when everyone feels seen and their purpose is clear.

Show Overview 00:00 Know Your Why to Succeed

03:19 Mentorship and Soccer Success

08:30 Teamwork Drives Collective Success

10:10 Choosing the Right Mentor

14:45 From Expertise to Leadership

17:08 Closing the Growth Gap

22:06 Backup Hero Stops 3 Penalties

22:37 Embracing Iron Sharpens Iron

In this episode of Keep Hustling, host Aaron Gordon sits down with Chelsea Fournier, a former business lawyer turned coach for solo-led founders. Chelsea shares her journey from law to entrepreneurship, emphasizing the importance of redefining your hustle, recognizing personal health needs, and listening to intuition. She breaks down concepts like "nervous system safe strategy" and how to invite intuition into the business world without sacrificing structure. Chelsea also offers practical advice for fostering self-trust and creating accommodations that empower individuals and teams to succeed. The episode closes with Chelsea's favorite Eleanor Roosevelt quote, inspiring listeners to own their future.

Get To Know Chelsea Fournier Chelsea Fournier is the founder of Intuitive Business By Design™. She empowers soul-led founders, coaches, healers, and creatives to build sustainable businesses without experiencing burnout or resorting to aggressive marketing tactics. A former business attorney turned intuitive strategist, Chelsea combines over 15 years of business expertise with grounded energy work to guide her clients toward clarity, alignment, and meaningful impact.

Through her signature ROOTED Roadmap Method™, Chelsea assists sensitive service providers in designing 90-day action plans that respect their energetic capacity and prioritize strategic goals. Her approach melds intuitive channeling with practical business strategies, empowering clients to align their offers, messaging, and visibility with their authentic vision.

Chelsea specializes in supporting soul-led entrepreneurs who are ready to evolve their business models, step into greater visibility, or establish systems that feel comfortable and authentic. She focuses on helping these individuals grow sustainably, with clarity, self-trust, and aligned action. Through her signature ROOTED Roadmap Method™, Chelsea helps sensitive service providers design 90-day game plans that honor their energetic capacity and strategic priorities. Her approach combines intuitive channeling with practical business strategy, enabling clients to align their offers, messaging, and visibility with their authentic vision.

Chelsea specializes in supporting soul-led entrepreneurs who are ready to evolve their business models, step onto a bigger stage, or create systems that feel like home. She does this without requiring them to sacrifice their energy or depth. Her mission is to help rooted leaders grow sustainably, with clarity, self-trust, and aligned action.

LinkedIn Intuitive Business By Design Youtube Instagram 3 Episode Key Takeaways

1. Redefine Your Hustle: Chelsea Fournier's journey from business lawyer to intuitive business coach demonstrates that hustle is not about intensity, but alignment. By stepping away from the "shoulds" and external expectations, Chelsea found greater fulfillment and flexibility, proving that success can be redefined to suit personal values and evolving life stages.

2. Prioritize Nervous System Safety: Chelsea introduces the concept of "nervous system safe strategy," encouraging listeners to build a business or career around what feels authentic and sustainable. Her story shows that pushing through discomfort for the sake of productivity can be detrimental to health and happiness. Instead, accommodating personal needs leads to more effective and enjoyable work.

3. Cultivate and Trust Intuition: Throughout the episode, Chelsea highlights the importance of self-trust and intuition in decision-making. She debunks the myth that intuition is impractical by blending it with structured thinking, inviting listeners to experiment with slowing down, tuning into bodily cues, and balancing logic with inner wisdom for better professional and personal outcomes.

Show Overview 00:00 Overachieving Path to Law School

04:16 Career Overhaul for Wellbeing

07:03 Healing Journey and Growth Reflection

12:36 Finding Alignment in Growth Strategies

14:59 Personalized Paths to Success

18:45 Trusting Intuition in Decisions

23:00 Intuition and Empowering Leadership

27:05 Intentional Decision-Making Takes Time

27:58 Pause to Clarify Success

In this episode of Keep Hustling, host Aaron Gordon sits down with Jay Sapovits, a driven entrepreneur whose story is all about reinvention, resilience, and the real work behind success. Jay shares how witnessing his father's unhappiness at work inspired him to never settle for a job he hated, fueling his journey through various industries. He reveals the true foundation of entrepreneurship—courage, a problem-solving mindset, and the ability to take action, even when it means making hard choices or facing failure. Jay discusses how fear holds many back and emphasizes the power of starting imperfectly instead of waiting for the perfect plan. He also busts the myth that you need an elite education or a world-changing idea to succeed, stressing that execution and perseverance matter most. The conversation is packed with honest insights on failure, resilience, and finding happiness by chasing what matters to you—not what the unicorns of the world achieve. Jay closes by sharing his favorite quote, "We rise by lifting others," highlighting the power of humility and generosity in any hustle.

Get To Know Jay Sapovits

Jay Sapovits is a dynamic entrepreneur and visionary leader, renowned for his ability to transform challenges into opportunities through creativity, resilience, and an unparalleled knack for building relationships. As the founder and CEO of Ink'd Stores, Jay has carved a unique path in the business world, shaped by a diverse array of experiences that reflect his relentless drive and adaptability.

Originally from across the country, Jay made a bold move at 18 to attend the University of Nevada, Las Vegas (UNLV), where his entrepreneurial spirit began to take root. Starting behind the counter of a Las Vegas dry cleaner, he gleaned invaluable life lessons that fueled his journey through eclectic roles, radio engineer, sports talk host, and golf course cart manager. Each experience honed his ability to connect with people and seize opportunities, ultimately leading him to travel with the UNLV basketball team and launch his business career with a pivotal one-day event alongside golf legend Sergio Garcia.

Jay's philosophy centers on betting on relationships over chance, a mindset that has guided his remarkable career. He has mastered the art of balancing personal identity with professional ambition, avoiding the trap of being defined solely by his work while using it as a powerful motivator. Today, Jay Sapovits continues to inspire as a trailblazer who thrives on reinvention, leading Ink'd Stores with the same passion and ingenuity that have defined his journey from the dry cleaner's counter to the forefront of entrepreneurship.

LinkedIn Instagram 3 Episode Key Takeaways 1. Courage Over Comfort: Jay Sapovits shares that true progress comes not from fearing the leap, but from fearing stagnation. He emphasizes that for many entrepreneurs, the real risk isn't in stepping out, but in staying put in unfulfilling roles. His journey illustrates that courage—rather than a perfect plan—is the first step toward meaningful entrepreneurship.

2. Execution Trumps the Big Idea: Jay dismantles the myth that only world-changing ideas guarantee success. Using relatable examples like local pizza shops, he explains that business growth is fueled by relentless execution and incremental innovation in already existing markets, rather than waiting for a once-in-a-lifetime inspiration.

3. Resilience and Reinvention After Failure: Jay openly discusses a public business failure, revealing that perceived setbacks are often not viewed as harshly by others as by oneself. His story underscores the importance of taking imperfect action, rebounding quickly, and redefining personal success by staying humble and adaptable in the face of adversity.

Show Overview 00:00 Discovering Entrepreneurship Through Problem Solving

03:45 Entrepreneurship: Solve Problems with Courage

08:35 Desperation as Motivation

11:00 Rebuilding After Setbacks

16:23 "Start the Right Business."

16:59 Execution Over Ideas

21:35 Alternative Education for Struggling Students

25:27 Embracing Reality Over Dreams

In this episode of Keep Hustling, host Aaron Gordon sits down with Zach Griff (aka The Points Guy) to dive into his journey from a South Florida kid obsessed with credit card points to becoming a top travel and loyalty expert. Zach shares how he turned his passion for maximizing miles and loyalty programs into a thriving career, the realities of life on the road (and in the skies), and the hustle required to stay ahead in a constantly changing industry. He offers practical travel hacks for beginners, reveals his favorite airline experience, and discusses the importance of using your points instead of hoarding them. Additionally, Zach reflects on balancing family life with nonstop travel and leaves listeners with an inspiring message about being a person others respect and look up to, no matter what industry they're in.

Get To Know Zack Griff

Zach Griff is a seasoned travel and aviation expert, award-winning content creator, public speaker, and startup advisor. As a senior reporter at The Points Guy (TPG) since 2019, he delivers insightful coverage of the airline industry, travel and product reviews, and in-depth analyses of loyalty programs. Concurrently, Zach is pursuing an MBA at the prestigious Wharton School at the University of Pennsylvania, further honing his expertise in business and strategy.

A sought-after voice in the industry, Zach's work has been featured in prominent outlets such as The New York Times, The Washington Post, HuffPost, CNN, Fox News, BBC, and the Axios Today podcast, among others. His ability to break down complex travel trends and loyalty programs has earned him recognition as a trusted authority in the field.

An avid traveler since 2012, Zach's passion for exploration began with a last-minute, business-class ticket to the Middle East redeemed through miles. Having visited 57 countries, he continues to share his global experiences through engaging storytelling and expert insights, inspiring others to navigate the world of travel with confidence.

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3 Episode Key Takeaways 1. Turn Passion Into a Career: Zach's story proves that obsessively pursuing what excites you, no matter how niche, can evolve into a rewarding profession. His childhood curiosity about credit cards and points became the foundation for his leadership at The Points Guy.

2. Maximize, Don't Hoard: Don't sit on opportunities waiting for the "perfect" moment. Zach encourages listeners to use their points (and by extension, their resources) boldly and wisely, emphasizing that doing is better than endlessly optimizing.

3. Adapt and Evolve Relentlessly: The changing landscape of travel, credit cards, and content platforms means constant reinvention is the key to long-term success. Zach's career reflects the importance of embracing change, learning new tools, and staying ahead in any industry.

Show Overview

00:00 Unexpected Journey into Travel Hacking

05:53 Lifelong Passion and Evolution

07:24 Passion Drives Content Creation

12:31 Airline Loyalty Program Changes

15:51 Points Redemption: Finding Your Baseline

18:44 JetBlue Travel Challenge Enthusiasm

21:15 Beginner-Friendly Chase Points Strategy

24:05 "The Points Guy Needed for Travel"

27:26 "Luxury Travel Preference: Flights Over Hotels"

32:27 Embracing Integrity and Hustle

In this milestone 100th episode of the Keep Hustling Podcast, host Aaron Gordon celebrates the journey of the show and expresses deep gratitude to listeners, guests, and the behind-the-scenes team who make it all possible. The episode features highlights from memorable interviews with a diverse group of hustlers—entrepreneurs, athletes, creatives, and industry leaders—each sharing the unique roots of their personal and professional drive. From stories of overcoming adversity and family influences to pivotal career moments and culture-shaping experiences, listeners gain inspiring perspectives on what it means to truly hustle. Aaron reflects on the common thread connecting every guest: a relentless pursuit of their own definition of success. The episode also acknowledges the importance of community, authenticity, and the lessons learned through consistent effort. As Aaron looks forward to more episodes, he reminds listeners to stay curious, hungry, and committed to doing well by doing good—concluding, as always, with the rallying cry: keep hustling.

Keep Hustling Guests Featured:

1. Adam Schefter 2. Bradley Flowers 3. Mario the Monk Trotta 4. Ciara Gravier 5. Zoli Hoenig 6. Shlomo Levinger 7. Jacob Birn 8. Brett Young 9. Dave Levinger 10. Josh York 11. Ryan Hanley 12. David Abrams 13. Bob Nackel 14. Dan Luxembourg 15. Yaakov Langer 16. Scott Howell

These guests represent a diverse range of backgrounds, including entrepreneurs, athletes, creatives, salespeople, mental health survivors, coaches, and industry leaders, all sharing their unique stories of hustle and perseverance.

3 Key Episode Takeaways

1. Define Your Own Hustle: Throughout episode 100, Aaron Gordon and his guests emphasize that there's no single path to success. Whether you're an entrepreneur, athlete, or creative, true hustle is about discovering what drives you, setting your unique goals, and relentlessly pursuing your own version of achievement—not someone else's definition. 2. Leverage Your Background — No Matter Where You Start: The diverse stories shared, from Bradley Flowers' upbringing surrounded by business owners to Ciara Gravier's "rule-follower" mentality, remind us that both privilege and adversity can fuel hustle. Your roots—whether humble or fortunate—are a toolkit, not a limitation. Harness your upbringing as a source of motivation, learning, and strength. 3. Resilience Transforms Setbacks into Success: Guests like Josh York and Brett Young share experiences of overcoming difficult childhoods and professional downturns. The common thread is resilience: viewing struggle as a catalyst, not a stop sign. Their journeys illustrate that embracing setbacks and pushing through hard times are essential in building lasting success and personal growth.

Show Overview

00:00 Keep Hustling Podcast's 100th Episode Intro04:25 Bradley Flowers' Entrepreneurial Roots 06:51 From Mario to the Monk 09:45 Fatburn: Startup Success Story 15:08 Self-Taught Through Music Piracy 16:37 Watch Now: Top American Hosts 20:59 Innovative Ad Strategy on WhatsApp 25:36 Career Transition and Resilience 27:05 Finding Identity Amidst Chaos 32:48 Defining Personal Hustle 38:51 Childhood TV Obsession Reflections 40:16 Scott Howell's Media Journey

On this episode of Keep Hustling, host Aaron Gordon sits down with Matt Krayton to unpack his unconventional journey from aspiring teacher to seasoned political consultant and leadership coach. Matt discusses how early setbacks in education led him into politics, the importance of authentic leadership, and why Curiosity triumphs over judgment.

Together, they reflect on the complexities of historical figures, the myths and realities of leadership, and how difficult conversations pave the way for growth—both in professional teams and personal development. Matt also shares his favorite motivational quote, encouraging listeners to stay curious and open-minded. This insightful episode is a must-listen for anyone looking to lead with impact and resilience.

Get To Know Matt Krayton

Matt is co-founder M2Aspire. He founded a national public affairs, strategic communications and political consulting firm, Publitics, 14 years ago. He has provided counsel to campaigns, candidates, elected officials, executives, founders, organizations, and brands for over a decade. He worked with Biden for President in 2020 on special projects including creating collateral for celebrity and influencer endorsements including NBA star Ben Simmons. His work on the campaign was recognized with a Campaigns and Elections Magazine Stanley F. Reed Award.

Matt is an innovator focused on keeping clients on the cutting edge. In 2022, under his leadership, Publitics launched InfluenceIQ™, a suite of tools for identifying and reaching nodes of influence with key messages, testing creative, modeling and building audiences and developing effective messaging. In 2024, he launched InfluenceIQ Labs™, a strategic investment arm of Publitics with a focus on supporting startups in communications, media, and AI, while providing clients with access to the latest technologies.

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3 Episode Key Takeaways

1. Redefine Leadership Beyond Charisma:

Matt Krayton unpacks the common misconception that leadership is all about charisma and strength. Instead, he emphasizes the importance of developing true leadership skills, such as effective communication, self-awareness, and the ability to unite people around a shared purpose. His experience coaching political and corporate leaders illustrates that substance, not just style, is what separates good leaders from great ones.

2. Leverage Curiosity Over Judgment:

Drawing inspiration from the motto "curiosity, not judgment," Matt encourages listeners to approach challenges, feedback, and self-reflection with an open and inquisitive mindset. By choosing Curiosity instead of criticism, individuals and leaders can better understand themselves and others, improve relationships, and find more creative solutions to problems—fueling both personal growth and organizational progress.

3. Transform Setbacks into Opportunities:

Matt's millennial career journey—from aspiring teacher to political consultant and leadership coach—highlights the power of adaptability and persistence. Facing industry downturns, layoffs, and unexpected career pivots, Matt turned obstacles into stepping stones by staying open to new paths and betting on emerging trends like social media in politics. His story underscores that every setback can become a launchpad for a new chapter if you remain resourceful and proactive.

Show Overview

00:00 Passion for Politics and Education

04:40 Teaching Joys and Drawbacks

07:37 Youthful Advantage in Social Media

12:21 Everyone Is Complicated

14:28 Inspiration, Politics, and Human Flaws

18:13 Future Views on Polarizing Presidents

19:37 Rethinking Charismatic Leadership

24:14 Unsung Heroes of Leadership

28:30 Redefining Effective Leadership Traits

29:27 Rethinking Leadership Beyond Influence

33:16 Mastering Difficult Conversations

37:02 Curiosity as a Superpower