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Let's Ride w/ Paul Estrada

Let's Ride w/ Paul Estrada

By: Paul Estrada
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About this listen

Who else is trying to figure $hit out?

Welcome to Lets Ride w/ Paul Estrada – the podcast where a dad tackles the big questions of life, career, and everything in between, by talking to interesting people that have the answers!

When I turned 18, I lost sleep at night with questions that Google was not yet sophisticated enough to answer: What career should I pursue? How can I be more than just average? And how do successful people get to where they are (was there a secret handbook I didn't know about)? After 22 years of pondering these existential dilemmas, I’ve finally pieced together some answers – An answer that is sufficient for now, but one always in need of refinement.

Join me each week as my 6 ½ year old son, Adrian, throws out a thought-provoking question or idea, and I invite a guest to help me sufficiently respond to him. From learning about money and investing, to finding a passion in life, and exploring careers that can be meaningful for you, we cover it all with a dose of humor and some soundbites of wisdom.

So, if you’re a parent or a young adult navigating these tricky waters, or if you want confirmation that other people are sometimes just as lost as you, you’ve come to the right place.

© 2025 Let's Ride w/ Paul Estrada
Career Success Economics
Episodes
  • Immigrant to Corporate VP: The American Dream is Alive and Well
    Aug 12 2025

    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.

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    50 mins
  • Solo Episode: DIY Nesting & Getting What You Deserve
    Jul 29 2025

    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.

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    32 mins
  • AI & Automation CEO: What Will or Kids Do when AI Does Everything?
    Jul 15 2025

    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.

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    51 mins
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