Behind every successful business lies a story of grit, sacrifice, and unwavering determination. In this extraordinarily personal episode, I share recordings of conversations with my grandparents Connie and Alejandro  Castellanos that I've been collecting since 2017, capturing memories that I didnt want to get lost to time.

Connie's entrepreneurial journey began at just nine years old, working in her father's grocery store where she mastered everything from inventory to bookkeeping without formal training. When she married my grandfather Alex, they embarked on a remarkable business adventure together. While Alex worked three jobs simultaneously, they took the extraordinary risk of purchasing a 12-unit apartment building for $135,000 in the 1960s – when their weekly income was merely $60.

The story unfolds through acquisitions of liquor stores and additional properties, with Connie painting vacant apartments after hours while raising five children. Their partnership exemplified perfect balance – Alex handling repairs and maintenance while Connie managed finances and operations. Despite financial pressures and long hours, they never let business consume their lives entirely, always making time for family outings and simple pleasures.

What makes their story so powerful isn't just their financial success, but how they achieved it without sacrificing happiness or family bonds. Their approach wasn't driven by wealth accumulation but by creating stability and opportunities for those they loved. As Connie reflects, "Not even in my wildest dreams did I ever think I would have this."

This episode contains wisdom for entrepreneurs at any stage: the importance of partnership, opportunistic thinking, calculated risk-taking, and maintaining perspective about what truly matters. Whether you're building your first business or growing an empire, you'll find inspiration in this intimate glimpse into an extraordinary entrepreneurial legacy.

Ever wondered how some people build extraordinary careers without following conventional paths? In this eye-opening conversation, we meet someone who crafted an impressive career journey—from trading floors to entrepreneurship—without ever formally submitting a job application.

Growing up in tiny Gallup, New Mexico, where opportunities were scarce, our guest developed remarkable resourcefulness from an early age. Rather than seeing limitations, he cultivated a deliberate approach to career building that focused on continuously acquiring new skills. "What is the piece of the puzzle that I'm missing in my own skillset?" became his guiding question when evaluating each potential career move. This methodical strategy—treating professional development like assembling a toolkit—eventually positioned him perfectly for entrepreneurial success.

The conversation reveals powerful insights about mentorship that challenge common assumptions. While many professionals hesitate to reach out to potential mentors, our guest demonstrates how straightforward the process can be: engage genuinely with people whose knowledge you value, ask thoughtful questions, and follow through. "The answer to every unasked question is always no," he reminds us—a simple but profound perspective that has opened countless doors throughout his career. His approach to relationship-building extended to LinkedIn, where he strategically built a following by sharing industry insights, effectively testing business concepts and building a client pipeline before launching his venture.

Whether you're early in your career journey, contemplating a shift to entrepreneurship, or simply looking for a fresh perspective on professional growth, this episode offers practical wisdom you can implement immediately. The message is clear and empowering: with curiosity, deliberate skill-building, and the courage to reach out, you can create extraordinary opportunities regardless of where you start.

What does it truly mean to pursue the American Dream? Sun Kwok's remarkable journey offers a powerful answer to that question.

Moving 31 times before his 18th birthday, Sun's life has been defined by constant adaptation and relentless perseverance. Born in China, he relocated to Hong Kong at age two before immigrating to the United States at seven with parents who spoke no English but carried immense hope for their children's future. His father, having battled cancer at just 28, wasn't seeking opportunity for himself – he was investing everything in his children's potential.

Sun's early American experience wasn't glamorous. His family stayed with relatives in cramped apartments before opening a small restaurant in what he describes as "the worst neighborhood ever" in New Jersey. By 13, Sun was working full-time in the family business while maintaining his studies, routinely skipping school on Fridays to help out. The restaurant connected directly to their apartment through a window Sun would climb through daily – a physical embodiment of how work and home life were inseparably linked.

Despite these demanding circumstances, Sun excelled academically before making a counterintuitive career move. After graduating college and successfully running his own restaurant, he abandoned entrepreneurship for corporate America – the reverse of most career trajectories. Why? As Sun reflects, "I thought about my parents who came to this country with a couple of suitcases and almost no cash, with kids on their backs, into a country where they didn't know the language. Compared to that, was I really exerting myself? Was I really trying?"

That mindset propelled Sun through the corporate ranks to his current position as a vice president in a multi-billion dollar organization. His secret? "When you see something that needs to be done and has value, just do it." Today, as he raises his own children in circumstances vastly different from his upbringing, Sun faces new challenges in imparting the values that shaped his success.

This episode will change how you think about opportunity, work ethic, and what it means to truly push yourself beyond comfort zones. Whether you're building a career, running a business, or raising a family, Sun's perspective offers invaluable wisdom about what's possible when determination meets opportunity.

Ever notice how impending parenthood transforms those long-ignored home projects into urgent missions? That's exactly where I find myself—deep in nesting mode, armed with caulk guns and Allen wrenches, frantically preparing for our newest family member arriving in just eight weeks.

There's something surprisingly satisfying about stepping away from keyboard work to create tangible results with your hands. Though YouTube makes everything look deceptively simple (seriously, those tutorial videos skip all the real-world complications), I've discovered newfound confidence tackling electrical work, AC repairs, and various home improvements. Each completed project brings a unique sense of accomplishment that my regular work rarely provides.

Between drywall cuts and furniture assembly, we managed a meaningful escape to Spain—a country that captured my heart during my college semester abroad. Returning now as a parent, the cultural contrasts became even more striking. While Americans race through life prioritizing productivity, Spaniards embrace a refreshingly different approach—restaurants where meals stretch for hours, children engaging in conversation rather than staring at devices, shops closing midday for rest, and dinner starting when most Americans are preparing for bed. This deliberate slowness creates space for connection and enjoyment that we often sacrifice in our efficiency-obsessed culture.

The trip held special significance because we brought my father-in-law, who at 70 hadn't returned to Madrid since living there briefly at 15 after leaving Cuba. These intergenerational experiences have heightened my awareness of time's passage and mortality—not in a morbid sense, but in recognizing the importance of creating meaningful memories while we can. Seeing my parents' vibrant interactions with their grandchildren reminds me how precious these moments are.

As I reflect on what wisdom I'd share with younger generations, perhaps the most valuable is this: no one will advocate for your advancement like you will. Throughout my career, I've observed too many talented people waiting for recognition that never automatically arrives. Whether in your professional life or personal pursuits, knowing your worth and actively going after what you deserve makes all the difference. The world rarely hands you opportunities—you must create them yourself.

What new skills or hobbies have you developed in your adult years? I'd love to hear how you're challenging yourself and growing, regardless of your age or stage in life. Subscribe to join our ongoing conversation about finding purpose and living intentionally through life's constant transitions.

What happens when machines can do our jobs better than we can? This question is no longer theoretical—it's the reality reshaping our economy right now.

My conversation with Chadd Olesen, CEO of a company building AI systems that are transforming business operations, left me genuinely stunned. Hearing an AI system negotiate over the phone using natural pauses, regional accents, and conversational rhythm completely indistinguishable from a human was a moment that will stick with me forever. This isn't science fiction—it's happening today.

But rather than predicting a jobless future, Chadd offers a refreshingly optimistic perspective: automation isn't eliminating work, it's elevating it. Workers are shifting from repetitive tasks to creative problem-solving, relationship building, and data analysis. The value of human work isn't disappearing—it's evolving.

As a father with a young daughter, Chadd balances his excitement about technological advancement with genuine concerns about the world his child will inherit. "I'm terrified not of AI, but of the economy," he admits, wondering how future generations will navigate a transformed economic landscape. Will housing become increasingly unattainable? Will education systems adapt quickly enough?

We also explore Chadd's journey from corporate America to entrepreneurship, discussing why large organizations often "reward the agreeable, promote the political, and bury the bold." His insights on building an online presence, the acceleration of technology development, and how AI will transform entire industries make this a must-listen conversation for anyone wondering what skills will matter most in the coming decades.

Whether you're a parent wondering how to prepare your children, a professional concerned about your career path, or simply curious about how AI is reshaping our world, this episode offers valuable perspective on navigating the greatest technological transformation of our lifetime.

Subscribe now and join our community exploring the intersection of technology, business, and human potential. Your future self will thank you.

What happens when the boardroom mindset collides with youth sports sidelines? This episode takes us on a deeply personal journey with a successful CEO whose competitive drive propelled him to the top of his industry—until he found himself struggling with his reactions to his 10-year-old son's club soccer experiences.

The conversation unfolds with remarkable candor as our guest reveals how watching his son play triggered unexpected emotional responses, leading him to question his parenting approach and values. "I'm laying up at night, waking up at 4 AM—I'm not thinking about my business, I'm thinking about this ordeal," he confesses, describing the inner turmoil that prompted his viral LinkedIn post on the topic.

We explore the fascinating psychological territory where high-achievement meets parenting, unpacking the complicated feelings many parents experience but rarely discuss. Our guest articulates the core dilemma perfectly: "Am I helping facilitate giving the opportunities and training I never had? Or am I scarring this little kid by the way I'm reacting?" This question resonates deeply with anyone who has found themselves invested—perhaps too invested—in their child's activities.

The most powerful moments come when our guest recognizes the fundamental difference between his relationship with competition and his son's perspective. While he "loved to compete and hated to lose," his son "loves to compete but doesn't really affect him if he loses"—a healthier outlook that challenges the parent's assumptions. We also hear about a transformative email from a club coach imploring parents to remember that their primary role isn't to be another voice coaching from the sidelines, but simply to be supportive parents.

Whether you're navigating youth sports as a parent, coaching young athletes, or simply interested in the psychology of competition and family dynamics, this conversation offers valuable perspective on finding the balance between supporting excellence and allowing children to develop their own relationship with achievement. Listen in and reflect on how we might all bring more joy and less pressure to the next generation's playing fields.

What if the key to a more fulfilling life isn't doing more, but doing differently?

Alex Payeta's journey begins like many ambitious professionals – climbing the corporate ladder, working relentless hours, and defining success through financial achievement. But something was missing. That realization led her to make a bold decision, walking away from a six-figure consulting career to pursue a more meaningful path. Through world travels, spiritual exploration in jungle retreats, and deeper connection with what truly matters, Alex discovered a different definition of wealth that transcends the material focus of her Orange County upbringing.

In this conversation, Alex shares practical wisdom for anyone feeling overwhelmed by life's demands. She breaks down how to create morning routines that actually work (hint: they don't need to involve cold plunges or two-hour meditation sessions), explaining why starting small with what matters most to you is the secret to sustainable habits. Her approach acknowledges the messy reality of life – early-waking children, unexpected interruptions, and the challenge of balancing work with family responsibilities.

Perhaps most refreshing is Alex's perspective on time management. She draws an important distinction between being efficient and being rushed, noting that rushing is often just a habit that doesn't serve us. Her weekly calendar audit practice offers a concrete way to align your time with your priorities, while her insights on clearly defining family roles prevents the resentment that builds when responsibilities remain ambiguous. As she puts it, "When you both think you're responsible for something, neither one of you is."

Whether you're struggling with morning chaos, feeling overwhelmed by your schedule, or questioning if your definition of success is truly your own, this episode provides both the perspective shift and practical tools to create meaningful change. Learn how running your life "like a business" – complete with structure, boundaries and intentional planning – can paradoxically create more freedom and joy than the reactive approach many of us default to. Ready to redefine what success looks like on your terms? This conversation is your invitation to start.

What happens when calculated risk-taking, unwavering values, and financial discipline converge? Adam Blanchard's remarkable journey from third-generation lawyer to multi-business entrepreneur provides the blueprint.

After realizing that a career in litigation wasn't his passion, Blanchard pivoted dramatically when a casual beer conversation with a friend sparked the idea to start a trucking company. This decision marked the beginning of a entrepreneurial path that would lead to founding multiple successful businesses across trucking, consulting, and real estate sectors. But what makes Blanchard's story particularly compelling isn't just his business acumen—it's the intentional approach that fueled his success.

Living with his grandmother to aggressively pay off student loans, Blanchard demonstrates how early financial discipline creates the foundation for entrepreneurial freedom. "The more frugal you are earlier on, the more the success is meaningful down the road," he shares, offering a refreshing counterpoint to the instant-gratification narrative often associated with entrepreneurship. His partnership philosophy—preferring to share ownership with people whose strengths complement his weaknesses—reveals how effective team-building has enabled him to scale multiple ventures simultaneously.

Beyond business, Blanchard's story includes unexpected chapters, from running for the Texas State Legislature to giving congressional testimony before U.S. Senators. Throughout these experiences, his commitment to core values remains unwavering, whether instilling financial responsibility in his four sons despite family success, or refusing to compromise his principles during his political campaign.

His parting wisdom resonates with aspiring entrepreneurs and executives alike: "If you can dream it, you can do it. Don't be sitting on your deathbed one day saying 'what if?' Just do it." Discover how Blanchard's journey demonstrates that entrepreneurial success comes not from avoiding risks, but taking calculated ones while staying grounded in solid financial principles and personal values.

Subscribe now to hear more conversations with business leaders who are charting unconventional paths to success.

Have you ever wondered what it takes to thrive in a career that's both financially rewarding and personally fulfilling while maintaining your most important priorities? Mark Maggio's journey offers a masterclass in navigating this delicate balance.

As a self-proclaimed "maniac," Mark built an exceptional 15-year career as a carrier sales representative before advancing to the C-suite of a multimillion-dollar logistics company. What makes his story particularly compelling is how he describes the genuine joy he gets from his work—using words like "adrenaline" to describe the high-stakes environment of freight brokerage where split-second decisions can mean significant financial rewards or missed opportunities.

Mark pulls back the curtain on what it's like to operate in the fast-paced world of logistics, where brokers match shippers with transportation providers against a literal "shot clock." He reveals that the secret to becoming a top 1% performer isn't about talking more—it's about listening deeply and solving problems effectively. For young professionals considering this path, he offers a tantalizing glimpse at the uncapped earning potential and entrepreneurial freedom of creating "your own business within a business."

But the heart of Mark's story lies in his family journey. When his son was diagnosed with autism and later lost his vision, Mark made the difficult decision to leave Chicago—the epicenter of the logistics industry—for Arizona to find better support services and improve his family's quality of life. This pivotal choice illustrates his core philosophy: "You don't live your life to work, you work to live your life."

Throughout our conversation, Mark shares wisdom on balancing professional ambition with family priorities, finding true satisfaction in your work, and supporting children's authentic interests rather than projecting your own definitions of success onto them. His ongoing efforts to trust his team, build effective processes, and be fully present for his family offer valuable insights for anyone struggling with similar challenges.

Whether you're considering a career in logistics, searching for strategies to achieve greater work-life balance, or simply seeking inspiration from someone who's successfully navigated these waters, this episode delivers powerful perspectives that will stay with you long after you've finished listening. Subscribe now to ensure you never miss conversations like these that blend practical career advice with profound life wisdom.

Ever wonder what drives someone to start a podcast? In this revealing solo episode, I pull back the curtain on my journey as a podcaster, father, and professional navigating life's unexpected turns.

As I approach 40, I share the real motivation behind creating Let's Ride—capturing those precious, curious conversations with my kids and providing a forum where we can all learn something valuable along the way. Growing up with entrepreneurial influences but unsure of my own path, I recount my sometimes comical attempts to unlock the "secrets" of successful people, including dropping letters in wealthy neighborhoods asking homeowners how they afforded their houses!

Through honest reflection, I tackle universal questions we all face: Is the corporate climb worth the sacrifice? Why does energy seem to vanish as we age? What does it mean to have a midlife crisis in today's world? I dive into the power of compound interest (my favorite party trick involves showing young people calculations on my phone) and share how my perspective on aging has completely transformed from my punk rock teenage years to corporate leadership.

This episode offers a window into the balancing act between ambition and contentment, youth and experience. Whether you're in your twenties wondering about your future path, or navigating midlife contemplating your choices, there's something here that will resonate with your own journey.

Join me for this candid conversation about life's forks in the road, the silent challenges of aging, and finding your path when there's no clear roadmap. Then let me know your thoughts—what questions would you like me to answer in future solo episodes?