In this episode of Keep Hustling, host Aaron Gordon sits down with Ben Barbic, a recording artist, author, and real estate broker out of San Jose, for a conversation that starts with a pile of weight plates. Ben's house burned down in a forest fire when he was five. The plates in the garage were the only thing that survived, so he sandblasted them and lifted with them all through his teens. He still has them. Two years after the family rebuilt, an earthquake took the house again, the day before his tenth birthday. What he pulled out of all that was less toughness than a pattern: build, lose, build back better. It is why a song that does not land is just a reason to write the next one. Aaron and Ben get into finding purpose in pain without pretending to feel good about it, why progress beats goals, and how music became the one place Ben has ever felt fully in control. He closes on the line that has stayed with him for years: the more I practice, the luckier I get.

Get To Know Ben Barbic

Ben Barbic is a recording artist, author, and real estate broker based in San Jose, California. His memoir, Rise & Climb: Finding Purpose Through Pain, is out now. He has closed more than $250 million in real estate through his brokerage, and he has spent decades working across music, fitness, real estate, and personal development.

His music blends reggae and hip-hop. He records and produces out of Where Dreams Sail Studios, where he has worked with reggae legends and with artists nobody has heard of yet, and his songs reach listeners worldwide through streaming playlists. He released an official soundtrack album alongside the memoir, with songs written to match its chapters.

Rise & Climb is written for high performers and for anyone in the middle of rebuilding. Barbic's own rebuilding started early. A forest fire took his family's house when he was five, and the only things that came through it were the weight plates in the garage. He sandblasted them and lifted with them through his teens. Two years after the family rebuilt, an earthquake took the house again, the day before his tenth birthday.

What came out of that was a habit rather than a slogan: build, lose, build back better. He credits a great uncle who was still curious into his nineties with showing him what staying at something actually looks like.

He keeps a daily practice of gym work and mountain climbing, and he has read more than five hundred books. He speaks and mentors people working through hard stretches, and his position is that nobody has to pick one path.

Both of his children are musicians releasing their own work, his son on jazz piano and his daughter as a singer. A song by the three of them has not happened yet, but he says it is in order.

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3 Key Listener Takeaways

1. Harness the discomfort instead of numbing it. Ben's advice for anyone in pain does not start with feeling better about it. The energy inside discontent is usable fuel. The move is to add one small thing you actually want for yourself, a walk, a run, anything, rather than reaching for whatever dulls it. It does not have to be a grand undertaking and you do not have to be happy about it.

2. Progress beats goals. He believes in goals, but he lives on progress, which is why he does not plan on retiring from what he is trying to accomplish. Framed that way, a song that does not land is a reason to make the next one rather than evidence the work was wrong.

3. The more you practice, the luckier you get. His closing quote, and his answer to anyone who calls somebody else's success luck. Keep showing up at the thing and the breaks start arriving. That is not luck. That is volume.

Show Overview

00:00 Meet Ben Barbic

05:55 The moments that shape you before you notice

09:29 Why a setback flips a switch instead of shutting one off

10:27 What to do when you are the one in pain

14:07 Music as the place he goes when life is chaos

18:01 What makes an artist easy to produce

21:37 The emotional spectrum we all share

24:28 The closing quote

In this episode, host Aaron Gordon sits down with entrepreneur and agency founder David V. Kimball to discuss the evolution of curiosity-driven side hustles and how experimentation, failure, and adaptability fuel long-term success. David Kimball shares how his early days building websites and following his interests taught him the value of persistence, even when instant results don't materialize. The conversation covers the importance of automating and outsourcing to free up time for what truly matters, the need for business owners to balance privacy concerns with technological progress, and how "creating more than you consume" can be a powerful catalyst for growth. They touch on the future of AI, responsible automation, and the temptation to over-optimize at the expense of meaningful experiences. David Kimball urges listeners to audit their routines, embrace tools that amplify their potential, and remember that true freedom requires self-discipline. The episode ends with an inspiring quote about moral restraint and an encouragement to always keep hustling.

Get To Know David V. Kimball

David V. Kimball is co-founder and CEO of lilAgents, where he leads strategy, SEO, and content. He is a digital marketer with more than 15 years of experience and a B.A. in Communication from Northwest University. He has led teams across software, staffing, and creative work, with a consistent focus on quality-of-life improvements for non-technical audiences.

Kimball lowers the barrier between people and the tools they need. Sometimes that means showing someone a tool that already exists. Sometimes it means making the tool itself. He is obsessed with process, platform agnosticism, and building new things that people can actually use.

At lilAgents, the agency he co-founded, the team builds AI systems for business owners so their time can go back to running the company and closing deals. Everything the agency builds is owned by the client rather than rented from the firm. The work is designed to compound, becoming more valuable over time instead of more expensive. Kimball describes the model simply: the team are the mechanics, not the landlords.

Part of that work is orchestrating AI agents to build and ship software. Examples of what he has built include award-winning apps that took first place in Netlify's Hot App Summer for shipping 30 open-source tools in 30 days, and first place in the CloudCannon and Astro challenge. He created Vault CMS, which lets writers publish an Astro website from Obsidian and is referenced in Astro's official docs, with 369 stars on GitHub. He also built Astro Modular, a blog theme for people who want a place online that belongs to them without building one from scratch, with 228 stars on GitHub. Across 21 Obsidian community plugins and his other public work, he has 861 GitHub stars. He has presented at Mike Schmitz's Practical PKM community, Hannah Siegertsz's Shipyard, and The Build Exchange, hosted by the AI Institute for Life Improvement in Tacoma.

Before lilAgents, Kimball spent 15 years in tech and marketing, including startup work at Gigster and Virtasant, six years of enterprise work at TrueBlue and Microsoft, and additional agency, indie games, and freelance roles.

He has worked remotely since 2018 from the Pacific Northwest, where he lives with his wife and kids. On his blog he writes about productivity, tech, and whatever he is working on. He builds with AI tools every day.

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3 Key Listener Takeaways

1. Create more than you consume. David drives home the power of shifting from passive consumption to active creation. Build, make, or invent, as a hobby or a new venture, and you unlock unexpected potential and greater fulfillment, regardless of current skill level.

2. Failure is not fatal. Pivot and persist. Aaron and David both stress that setbacks, failed ideas, and experiments are part of progress. The willingness to try, fail, adapt, and keep moving is how personal and professional evolution actually happens. Every misstep can become a stepping stone.

3. Harness curiosity and technology. This episode treats a curious mindset as a competitive advantage. David shows how embracing tools like AI and automation, while understanding their boundaries, helps people and businesses reclaim time for what matters most, keep innovating, and stay ahead in a rapidly changing world.

Show Overview

00:00 Curiosity and the drive to create

06:37 Learning from social media failures

09:37 Challenges of marketing strategies

13:32 Balancing automation and human effort

14:32 Fears and realities of automation

17:39 Privacy and tech solutions

22:59 Internet access and evolving knowledge

27:06 Wrapping up with listener engagement

27:38 Goodbye and encouragement

In this episode of Keep Hustling, host Aaron Gordon sits down with Michael Balarezo to talk through his path from Miami to claims work, Silicon Valley engineering, and a life in Colorado. Michael has seen insurance from both sides of the desk. He started as an all-lines adjuster, then built software for companies that included Google, Amazon, and Disney. In December 2021 the Marshall Fire hit his Boulder home. His family lost nearly everything on the main level and upstairs. The claims and rebuild process that followed felt like a second full-time job for two years.

That experience changed how he treats people in the process and why he co-founded Adjusto, the autopilot for contents claims. He walks through the scramble of evacuation, why the right coverage has to be in place before the smoke reaches the driveway, and how little most consumers are ever taught about their policies. The conversation gets into the hard realities of a claims system built for one house, not a thousand at once, and why the industry needs better tools as disasters arrive every year instead of once a decade. Michael closes with the Galaxy Quest line that became his working rule: Never give up, never surrender.

Get To Know Michael Balarezo Michael Balarezo is co-founder and CEO of Adjusto. An American software developer, futurist, and insurtech entrepreneur based in Boulder, Colorado, he is building recovery infrastructure for the disaster era.

He has seen personal property loss from every seat. After college he worked claims as an all-lines adjuster, then moved into software engineering in Silicon Valley. He spent eight years in engineering and technical leadership at MightyHive before serving as Global VP of Enterprise Automation at Media.Monks, where he led internal automation and AI strategy.

The Marshall Fire showed him how contents claims break carriers at both ends of the book. Most claims are small, under $5,000, and adjuster time often costs more than the payout. Large losses consume entire teams for months while families wait. When a catastrophe hits, both problems compound. Experienced adjusters get pulled to the fires, and the everyday claims behind them sit and rot in the queue.

That is why Balarezo co-founded Adjusto in 2024 with James Terry and Reid Greer. One platform handles the full severity spectrum. Small claims resolve touchless in hours. Large losses get world-class orchestration backed by the patent-pending FairMatch valuation engine, which pairs adjuster logic with market consumer data, plus TPA-enabled field services. Every claim gets exactly the treatment it needs.

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3 Key Listener Takeaways 1. Preparation meets peace of mind. Michael's calm during the Marshall Fire evacuation came from work done early: documenting possessions and understanding the policy before the crisis arrived. Knowing your coverage and keeping it current is the difference between panic and a plan.

2. Empathy from experience. Moving from adjuster to claimant put him inside the stress and emotional swing policyholders live through. Seeing both sides of the process made empathy nonnegotiable, for people in the industry and for anyone catching one of life's curveballs.

3. Never give up, never surrender. Whether you are fighting through an insurance claim or rebuilding after a total loss, the episode lands on persistence, adaptability, and a refusal to quit as the hustler mindset that gets you through adversity.

Show Overview 00:00 Getting into insurance in Colorado

04:53 The role of insurance adjusters

07:25 Understanding insurance for big purchases

11:41 Escaping the wildfire emergency

15:40 Insurance and peace of mind

16:22 Importance of early preparation

22:45 Being open about past roles

25:58 Addressing industry challenges with empathy

27:30 Recognizing outdated claims processes

In this episode of Keep Hustling, Aaron Gordon welcomes Mark Lewis, author of Give a Damn: The Ticket to Cultural Change. They discuss the importance of serving others, the impact of small positive actions, and how empathy and intentional engagement can transform both professional and personal lives. Mark Lewis shares insights from his experience running CEO roundtables, his book's core principles, and how technology is eroding face-to-face interactions. They highlight the value of fostering meaningful connections whether at work, in families, or through community and religion, and address barriers to cultural change including negativity and ego. The episode closes with Mark Lewis's motivational quote: "Individually, you make a difference. Collectively, we change the world."

Get To Know Mark S. Lewis Mark S. Lewis is CEO of Evolve Media AI, a professional speaker, leadership coach, CEO Roundtable facilitator, and best-selling author of Give A Damn! The Ticket to Cultural Change. He is a senior executive with a proven track record of building, leading, and guiding organizations, teams, and executives through growth, acquisition, and turnaround.

Mark co-founded the first locally owned Internet services company in New Orleans and grew its revenue from zero to nearly $4 million in less than three years. He established three remote branch offices, forged strategic partnerships with local exchange carriers, and helped negotiate the company's sale to a Fortune 1000 firm. He later merged three start-ups into a single entity, driving a 30% revenue increase in just two months, then negotiated the multi-million-dollar sale of that combined company to a wireless Internet provider.

His experience spans leadership coaching, sales and marketing, new business development, strategic planning, finance, and operations across both start-ups and established companies. He has led IBM agent firms in developing sales and marketing plans that improved profitability and designed a successful turnaround strategy that rescued a nonprofit organization from bankruptcy. Since 2014 he has implemented and moderated more than 25 CEO Roundtables.

Mark's contributions have been widely recognized. He was named Technology Leader of the Year in Louisiana by the Governor's Office, selected as the Marshall Klein Entrepreneur of the Year by the Entrepreneurial Organization of Louisiana, and honored as Rising Tide Small Business of the Year in Technology by the New Orleans Chamber of Commerce. In 2023 he was recognized nationally as a Leadership Coach by the Coach Foundation.

Results-oriented and focused on accelerating both growth and fulfillment, Mark continues to help businesses and individuals stay on a clear path to success.

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3 Key Listener Takeaways

1. Serve Others to Serve Yourself Mark Lewis shows that lasting success grows from putting the needs of others first instead of chasing personal gain. A mindset of service and empathy leads to deeper personal fulfillment and stronger internal well-being in both business and life.

2. Small Gestures Create Culture Throughout the conversation Mark demonstrates how simple, thoughtful actions such as saying "please" and "thank you" or holding a door open can lift organizational and personal cultures. These everyday behaviors create a powerful ripple effect that improves relationships, positivity, and even health and happiness.

3. Make Connection a Priority The episode underscores the cost of letting technology crowd out real interaction. Aaron and Mark both stress the importance of protecting time for authentic, in-person communication through family meals, community involvement, or workplace collaboration so people can build deeper connections and a more balanced life.

Show Overview 00:00 Discovering connected family ties of guest and host in Syracuse

04:31 Improving interpersonal skills

09:13 Thoughtful company culture strategies

12:50 Discussing the importance of the Sabbath

14:58 Link between religion and longevity

17:25 Importance of Religious Legacy

20:19 Justifying wrong actions

24:37 Examining obstacles to happiness

27:35 Podcast sign-off and contact info

In this episode of Keep Hustling, host Aaron Gordon sits down with entrepreneur and author Paul Mikel to explore how generosity and relationship-building can become powerful advantages in business and life. Paul shares his journey from waiting tables in Texas to building multimillion-dollar businesses, highlighting moments when simple acts of kindness like tipping well or remembering personal details opened unexpected doors. The conversation digs into the value of giving without expecting anything in return, the "Shut Up and Tip" mindset, and the importance of staying humble and grateful as success arrives. Paul emphasizes that true wealth is measured by the richness of relationships, not just financial rewards. The episode closes with his favorite quote: "Never forget where you came from or you're probably on your way back there," a clear reminder to stay grounded in your roots.

Get To Know Paul Mikel Paul Mikel is an entrepreneur, business strategist, speaker, and the author of Shut Up & Tip, a book that challenges people to rethink what exceptional service, leadership, and human connection really look like.

For more than 35 years, Paul has built businesses, led sales organizations, developed marketing strategies, and trained thousands of people across multiple industries. His career has centered around one simple philosophy: success isn't created by luck. it comes from serving people at a level most are unwilling to reach.

Throughout his career, Paul has worked with startups, Fortune 500 companies, entrepreneurs, and sales professionals, helping them increase revenue, improve customer experience, and build businesses that create lasting impact. His passion for self-development, leadership, communication, and personal growth has made him a sought-after speaker who believes that every interaction is an opportunity to leave someone's day better than you found it.

Today, Paul is involved in multiple ventures spanning technology, media, entrepreneurship, and business development while also producing podcasts and creating content focused on helping people think bigger, serve better, and live with greater purpose.

His latest book, Shut Up & Tip, is much more than a book about tipping. It's a blueprint for building stronger relationships, creating unforgettable experiences, increasing influence, and discovering that generosity is one of the most overlooked competitive advantages in business and in life.

Whether he's discussing entrepreneurship, customer experience, leadership, sales psychology, personal development, or the future of business, Paul's message remains consistent:

Success follows those who make other people's lives better first.

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3 Key Listener Takeaways 1. Generosity as a Hidden Advantage: Practicing genuine generosity builds trust and relationships that often pay unexpected dividends. Paul Mikel shares how consistent acts of kindness, like tipping well or building real connections, opened doors and fueled major business opportunities.

2. Invest in Relationships, Not Just Transactions: Your network grows through authentic interactions. Aaron Gordon and Paul Mikel emphasize that remembering small details about people, from valets to business partners, can pave the way for lasting friendships and crucial business introductions.

3. Keep Hustling and Stay Humble: Never forget where you started. Both Aaron Gordon and Paul Mikel stress that ongoing hustle, gratitude, and remembering past struggles keep you grounded while building the resilience to tackle new challenges and seize future wins.

Show Overview 00:00 Growing up with a giving mindset

04:05 Discussing generosity in business

08:50 Discussing tipping and restaurant wages

11:19 Building relationships for business success

14:11 Building connections through introductions

16:46 Son's car accident help

22:49 Reflecting on personal growth and gratitude

25:01 Reflecting on personal growth

29:01 Talking with Post Malone's manager

32:50 Asking for reviews and feedback

In this episode of Keep Hustling, Aaron Gordon welcomes Jessi Hartnett, author of "Honor Your Heart: A Soulful Guide to Quitting Smoking" and host of the You Can Quit Smoking podcast, to discuss the emotional and spiritual aspects of overcoming smoking addiction. Jessi Hartnett shares insights about how most people start smoking out of a desire for belonging or as a way to cope with grief and emotional pain, emphasizing that addiction often fills a void created by self-worth issues or unmet emotional needs. The conversation explores the importance of understanding these underlying motivations and replacing the habit with healthier ways to meet those needs, highlighting that long-term change relies on personal transformation, self-compassion, and reconnecting with one's intuition. Both speakers agree that quitting is often rooted in emotion rather than logic, and that unlocking a sense of self-worth and personal growth is crucial to overcoming addiction. Jessi Hartnett encourages people to focus on themselves, fill their own cups, and find peace within, quoting Rumi's "A wound is the place where the light enters you" as a reminder that healing and transformation often come from our deepest struggles.

Get To Know Jessi Hartnett Jessi Hartnett is the author of Honor Your Heart: A Soulful Guide to Quitting Smoking and host of the You Can Quit Smoking podcast. A former heavy smoker who struggled with addiction for 15 years, she now helps others break free by addressing the emotional and spiritual roots of the habit rather than relying on willpower alone.

Jessi teaches that smoking often fills voids created by a need for belonging, grief, low self-worth, or unmet emotional needs. Her approach centers on self-compassion, reconnecting with intuition, and replacing the habit with healthier ways to meet those deeper needs. She believes lasting change comes from personal transformation and learning to "fill your own cup."

Through her book, podcast, and coaching, she shares a heart-centered path to quitting that prioritizes healing and growth over shame or rigid formulas.

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3 Key Listener Takeaways 1. Understand the Emotional Roots of Addiction: The conversation focused on how addiction, particularly smoking, often stems from emotional needs such as belonging, initiation, or coping with grief. Recognizing that addiction is not purely about chemical dependency, but often about addressing deeper emotional voids, can be the first step towards meaningful change. 2. Replace Habits by Meeting Core Needs: One concept discussed was the importance of identifying the true needs that a habit like smoking fulfills—whether it's comfort, self-care, or a sense of rebellion. Approaching transformation means finding healthier ways to meet those needs, using creativity and persistence, rather than simply relying on willpower or logic. 3.Self-Worth Fuels Sustainable Growth: A key theme that emerged was how issues of self-worth and authenticity can act as barriers to breaking unhealthy patterns. The discussion explored how prioritizing self-care and fostering a genuine connection with oneself can empower individuals to achieve peace, drive personal change, and ultimately "keep hustling" towards a more fulfilling life.

Show Overview 00:00 Guest sourcing and discovery challenges

04:57 Cultural reasons behind smoking

08:42 Struggling with smoking addiction

10:52 Teenage rebellion and smoking

15:03 Understanding needs and addiction

18:02 Finding personal motivation

21:50 Starting conversations with curiosity

24:21 Breaking free from harmful habits

27:47 Podcast reviews and social media

In this episode of Keep Hustling, host Aaron Gordon sits down with J Reed Durand, a highly accomplished Army veteran and leadership expert. Drawing on 40 years of military and professional experience, they dig into the realities of leadership, personal growth, and change management. J Reed shares hard-won lessons from his journey, including the shift from being led to leading, the power of owning your own development, and his practical Three C's framework: confidence, capabilities, and capacity. The conversation explores the challenges and rewards of adapting to change, the role of discipline, and the courage it takes to step into leadership. Through stories of multiple relocations and varied career assignments, he offers clear, usable advice for anyone who wants to grow and help others grow. Lasting change, he stresses, starts with ownership and consistent training. The episode closes with a favorite motivational line that captures the heart of the discussion: "We don't rise to the level of our aspirations, we fall to the level of our training." Listeners walk away with actionable insights on leadership, self-improvement, and preparing for change, all in the spirit of Keep Hustling

Get To Know J Reed Durand J. Reed Durand rose from Private to Chief Information Officer through four decades of frontline leadership in one of the world's largest and most complex institutions, the U.S. Army. Across dual military and civilian careers he guided personal, team, and enterprise level transformations while refining practical, field tested approaches to change in high stakes environments.

After retiring twice he stepped back to examine the patterns behind successful continuous change. From that reflection came the Train to Change series, which blends leadership, psychology, philosophy, and organizational behavior into grounded, immediately usable strategies for personal and professional growth. His first book, Train to Change Phase One Self Mastery, is available worldwide. The follow on eBook, Train to Change Realism, advances the series into Phase Two.

Reed's work bridges theory and lived experience. It offers audiences a disciplined yet deeply human approach to self mastery. His core belief is straightforward: lasting transformation begins with taking ownership of your own development. He helps others understand change, prepare for it, and turn it into a catalyst for growth in an increasingly complex world.

As a change practitioner, years spent in varied roles and locations around the globe, paired with related education and training, gave him a practical understanding of self improvement, goal setting and achievement, continuous process improvement, and leadership. Along the way he developed and refined a repeatable methodology that he consistently applied to his own growth and career. He also used this hybrid approach to initiate, plan, organize, direct, and sustain large scale organizational changes that affected hundreds of thousands of Soldiers, employees, and leaders across the Army.

After his second retirement he distilled those lessons into a self improvement series published with the freedom of an independent author. The insights apply to anyone managing change, regardless of background, location, or destination. In short, this approach works.

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3 Key Listener Takeaways

1. Stepping Into Leadership: The conversation centers on the pivotal moment when someone moves from being led to leading others. Drawing from military experience, J Reed explains that real leadership means accepting accountability, embracing influence, and owning team outcomes. Even small leadership opportunities can open the door to growth and new possibilities. 2. The Three C's of Sustainable Growth: One of the strongest ideas shared is the framework of confidence, capabilities, and capacity. Building self-awareness, pursuing deliberate training, and developing the ability to perform consistently form a practical blueprint for effective leadership and continuous improvement in any environment. 3. Adaptability Over Comfort: A recurring theme is the necessity of change and the danger of getting too comfortable. Embracing constant learning and adaptation, whether driven by technology or life shifts, keeps you relevant and successful. Accepting the flow of life and training for change becomes a clear roadmap for maintaining momentum and thriving in uncertainty.

Show Overview 00:00 Gratitude to a veteran

03:44 Promotion to Sergeant

07:58 Reflecting on a 40-year Army career

11:36 Balancing Confidence, Capability, and Capacity

14:30 Building Confidence for New Routines

17:10 Adapting to tech changes

22:05 Inspiring next-gen leadership

23:32 Assessing Your Current Situation

26:48 Training for Personal Change

Travel writer Whitney O'Halek joins Aaron Gordon on Keep Hustling to share her inspiring journey from growing up in rural Tennessee to exploring the world and overcoming unimaginable tragedy. Whitney recounts how her passion for travel, sparked early by a desire to experience global cultures, became the foundation of her life and marriage. The episode turns deeply personal when Whitney describes losing her husband to choking on a flight home from Egypt, and how that moment catalyzed her mission to help single parents travel. She discusses resilience, the power of purposeful action amid grief, and her decision to continue traveling solo with her young daughter. Whitney delivers practical travel tips, reflects on adaptability, and advocates for anti-choking devices on flights. The episode is packed with motivation on facing adversity, redefining hustle, and finding fulfillment even when life feels half empty.

Get To Know Whitney O'Halek

Whitney O'Halek is a travel writer and storyteller who has spent two decades exploring the world and writing about it. Her journeys began solo, grew with her husband, and later continued as a family. Travel has always been how she processes life, builds connections, and tells honest stories.

In January 2025 her healthy husband passed away mid-flight. In that moment she became a solo parent traveler with an infant, stepping into a life she never planned. Grief changed everything, yet it did not erase her pull toward the world or her determination to show their daughter the places they had dreamed of seeing together.

Today she channels that resolve into Half Full Passport, a resource for single parents, the grieving, and travelers everywhere. She chooses to see the passport as half full rather than life as half empty. Her writing blends practical travel insight with candid storytelling, capturing destinations, everyday moments, and the quiet resilience that surfaces when plans unravel.

With nearly twenty years of experience across blogs, books, and media, Whitney is the author of the Lost and Found series of travel novellas. She has partnered with tourism boards and brands and appeared on podcasts including The RV Destinations Podcast, The Israel Travel Podcast, and The Egypt Travel Podcast. Through it all she continues documenting the reality of moving through the world after loss, inviting others to keep going with open eyes and a full heart.

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Show Overview 00:00 Introduction to Keep Hustling Podcast

04:56 Small town vs. big city perspectives

08:54 Travel mishaps and lost car seat

12:12 Focusing on solo parent travel

15:03 Balancing family with travel goals

17:57 Special time with my daughter

22:27 Finding positivity in challenges

25:15 Finding fulfillment in purpose

28:13 Missing a flight with young kids

30:55 Promoting LifeVac in public spaces

In this episode of Keep Hustling, Aaron Gordon sits down with insurance entrepreneur Tyler Woodall to explore how unconventional hustle and genuine connections can shake up even the most traditional industries. Tyler shares his journey from fresh college graduate to successful agency owner. He explains how doubling down on effort, personalizing client relationships, and embracing technology, such as virtual assistants and AI, fueled his growth. The conversation covers breaking industry stereotypes, the power of deep product knowledge, balancing risk, and finding opportunity in adversity. Tyler closes with a powerful quote: "Don't tiptoe through life to arrive safely at death." It is a challenge to listeners to take calculated risks and carve their own path. This episode offers strong motivation for anyone looking to innovate and redefine hustle in any field.

Get To Know Tyler Woodall

Tyler Woodall, CLCS, is the founder of ScaleOps and AgencyAid. He helps independent insurance agency owners break through operational ceilings and scale profitably without adding in house staff or burning out. Tyler knows the challenges of running an insurance agency firsthand. He built The WIN Agency from the ground up, navigating every pain point: hiring struggles, backend chaos, piles of quotes, delayed service requests, missed renewals, and nonstop ringing phones. After growing

and successfully exiting that agency, he refined the systems and strategies that worked and created solutions to help others overcome the same obstacles.

Through AgencyAid, Tyler provides fully trained, insurance specific virtual assistants who integrate seamlessly into agency workflows. These professionals handle quoting and service support, billing follow up, renewals, client communication, and essential admin work. This gives owners reliable bandwidth without the overhead of traditional hiring.

Through ScaleOps, he deploys smart AI solutions such as Ava, a 24/7 virtual receptionist that answers calls, captures leads, and routes them instantly. The combination of real people and intelligent automation eliminates missed calls, speeds up response times, lowers operating costs, and elevates the client experience.

The results speak for themselves. Agency owners reclaim more than 20 hours per week, reduce overhead, and accelerate growth. Tyler and his teams have helped over 500 agencies across the country streamline operations, boost revenue, and reclaim their time. His approach is simple yet powerful: real people plus smart AI equals unstoppable growth.

A designated Commercial Lines Coverage Specialist (CLCS), Tyler brings deep industry expertise to every engagement. His mission is clear: fix the broken backends that hold agencies back by providing the people, processes, and tools they need to escape the daily grind and focus on what matters most, building thriving, sustainable businesses.

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3 Key Listener Takeaways 1. Differentiate by Being Yourself: Tyler shows that bringing your unique personality and authentic approach to a traditional industry can be a game changer. By connecting with clients through shared interests, creative interactions, and genuine relationship building, he stands out in a field often known for suits and ties. His energy and individuality prove that being yourself can drive real business success.

2. Outwork and Outlearn the Competition: Success is not just about hustle; it is about technical mastery. Tyler dove deep into industry manuals and policies, doubling down on training and preparation. His story makes it clear that mastering your craft and being willing to do twice what others are willing to do is often the winning formula for building trust and outperforming competitors.

3. Take Calculated Risks and Pivot: Both Aaron and Tyler highlight the importance of chasing new opportunities, whether launching a scratch agency or building a VA staffing business. By hedging downside, preparing for worst case scenarios, and viewing setbacks as catalysts, they demonstrate how calculated risk taking and smart pivots can open exponential avenues for growth and reinvention.

Show Overview 00:00 Catching up with insurance industry friends

06:14 Starting out in insurance sales

08:34 Building relationships with contractors

09:56 Fashion shift in medical industry

13:42 Building rapport in service business

17:30 Building relationships with small gestures

22:11 Personal challenges and life changes

24:35 Exploring new revenue streams

27:51 Encouraging listener engagement

In this episode of Keep Hustling, Aaron Gordon sits down with Joe Infante, former member of the US Army's 82nd Airborne Division and a seasoned business consultant. Joe shares how his early struggles and military service transformed his work ethic and outlook. He went from underachiever to Dean's List student and successful entrepreneur. The conversation explores lessons about resilience, the importance of serving others, and how any experience, no matter how tough, can teach valuable skills. Joe discusses leadership, team building, and why hiring complementary strengths is crucial for scaling businesses. He also highlights the evolving work ethic in younger generations and the value of outside mentorship. The episode wraps up with Joe Infante's favorite motivational quote: "The best thing you could do is the right thing. The next best thing you could do is the wrong thing. The worst thing you could do is nothing."

Get To Know Joe Infante

Joe Infante, CEO of Compass Left, is a strategic visionary and transformative business executive who aligns technology, people, processes, budgets, and timelines to drive growth and operational excellence. With a proven ability to identify and resolve organizational deficiencies, Joe builds high-performing teams, streamlines operations, and forges seamless alignment between IT and business units.

A skilled leader with superior analytical, communication, and consensus-building talents, he excels at talent acquisition, strategic implementation, and fostering collaboration across cultures. His military foundation as a US Army 82nd Airborne Division Combat Engineer and Senior Drill Instructor in the 78th Infantry Division (R) reinforces his disciplined approach to leadership and execution.

Joe delivers impact across key areas including M&A and acquisition integration, IT roadmaps, governance, vendor and risk management, business process optimization, strategic partnerships, and cloud/ERP initiatives. He helps organizations accelerate performance and achieve sustainable success.

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3 Key Listener Takeaways 1. The Power of Work Ethic: Joe Infante stresses that a strong work ethic and continual forward momentum are foundational to long-term success. Even when starting in hard, unenviable jobs or feeling lost, his story shows that perseverance and not letting others down ultimately build confidence, open doors, and develop a sense of purpose.

2. Embrace and Learn from Every Experience: Joe Infante illustrates how every job, no matter how menial, can teach patience, discipline, and valuable life lessons. By sharing his path from making cinder blocks to military service and business leadership, he encourages listeners to recognize and extract value from each life chapter. Growth often comes from unexpected places.

3. Build Teams for Strength, Not Similarity: Joe Infante highlights the danger of hiring in your own image and the importance of complementary partnerships. Drawing on examples from his businesses, he advocates for identifying your integrator or visionary counterpart to balance strengths, scale effectively, and sustain growth without creating dysfunction.

Show Overview 00:00 Guest introduction and welcome

04:20 Joining the 82nd Airborne

06:35 Discussing the pressure of film sets

09:48 Volunteering with high school entrepreneurs

13:58 Young talent in consulting projects

16:05 Understanding business growth and leadership

22:14 Finding the right business partner

23:21 Learning to Step Back