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Let's Ride w/ Paul Estrada
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.
Episodes
35 episodes
Supply Chain Expert: Choosing Uncertainty Over Comfort
You can do everything “right” and still feel stuck. That’s the tension at the heart of my conversation with Niraj Jha, a guy whose life is basically a case study in reinvention. He grows up in India in a culture where the default success path i...
DC Lobbyist: Raise Your Hand When Opportunity Calls
Most people don’t miss opportunities because they’re lazy. They miss them because they don’t recognize the moment for what it is, then they never follow up. That’s why this conversation with Sean Todd hit so hard for us: it’s a real, messy, fun...
Solo #3: The Business Card That Changed My Life
I’m recording solo at 9:18 p.m. in a quiet house with a sleeping seven-month-old upstairs, and a baby monitor to my right. It starts as a simple reset, then I clean out my garage and stumble into a time capsule that stops me cold: an old busine...
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Movie Producer: How To Keep Moving When Life Knocks You Down
Dawn Krantz built a career by walking into rooms with no credentials and leaving with results. We dig into her first big swing in Austin real estate—pre-Google, pre-YouTube—where she fought through no after no, learned to face a city council wi...
Podcaster: Discipline, Sobriety, & Building a Brand
What if your goals are fine, but your foundation is weak? That’s the uncomfortable question we sit with as Chris Jolly, the Freight Coach, walks us through bootstrapping a media-first logistics brand, quitting alcohol, and building the kind of ...
Movie Screenwriter: From Capitol Hill to Hollywood, The Journey of Reinvention
A life can change direction without warning, but the real shift often starts with a quiet tug that refuses to go away. That’s the throughline of our conversation with Chris Plochin, who went from Senate mailrooms and House back rooms to writing...
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Athlete Advisor: Faith, Purpose, and Raising Kids with Character
What makes a goal worth chasing if no one is handing you a trophy? We open with that simple, disarming question and follow it into a rich conversation about character, faith, and the kind of grit that lasts longer than applause. Our guest, lead...
Motivational Speaker: Stop Chasing Titles, Start Becoming Your Best Self
A simple moment—a kid feeling overwhelmed by second-grade responsibilities—opens the door to a bigger truth: life keeps asking more of us, and the way we answer shapes who we become. That set the stage for our conversation with Scharrell Jackso...
Survivorman Les Stroud: The Difference Between Surviving & Living
The cold is honest. That’s one of the first lessons Les Stroud shares as we dig into what real survival feels like when there’s no crew, no scripts, and no second takes. Beyond the legends of Survivorman, Les opens up about pain, boredom, and t...
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Sales Entrepreneur: Building, Losing, And Choosing Contentment
What does it really take to walk away from a cushy six-figure job, sell your house, and bet on yourself? Marty joins me to share the unfiltered story of building a product company from scratch, finding his edge in trust-based sales, and staying...
Philanthropist: How Small Acts Can Lead To Big Change
What if the most reliable path to impact isn’t a grand gesture, but a habit? We sit down with Ann Canela to unpack how a childhood marked by strict rules and food insecurity forged an uncommon lens on giving, volunteering, and community. At 17,...
NICU Doctor: Navigating Our Daughter's First Fight
A quiet dinner turned into alarms, an emergency C-section, and a crash course in the NICU. When our daughter arrived five weeks early with her cord tightly wrapped and knotted, we met a calm, clear voice in the chaos: Dr. John Tran, a board-cer...
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Content Creator: From Memes on the Couch to Industry Influencer
Paul Bernard-Jaroslawski's journey from freight broker to influential content creator begins with a unique international upbringing that shaped his worldview. Born in Chicago to Polish immigrants who fled communist Poland just before its fall, ...
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Hard Work and Happiness: How My Grandparents Built Their American Dream
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 ...
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Startup Founder: The Art of Deliberate Career Building
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 form...
Immigrant to Corporate VP: The American Dream is Alive and Well
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 pe...
Solo Episode: DIY Nesting & Getting What You Deserve
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 famil...
AI & Automation CEO: What Will Our Kids Do when AI Does Everything?
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 tran...
Travel Ball Dad & CEO: Sideline to Boardroom Balancing Act
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 strug...
Time Management Expert: Design a Life that Works for You
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 fin...
Serial Entrepreneur: Building a Business Empire from Scratch
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 ...
Sales Representative: Grinding to the Top
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 bala...
Solo Episode: The Two-Day Hangover
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 mot...
Logistics Expert: Balancing Professional Ambition & Personal Fulfillment
What happens when you prioritize both career success and family fulfillment? Alyssa Coriel's journey offers a masterclass in modern work-life integration that defies conventional wisdom. Rising from an entry-level position to Vice ...
Harvard Trained Physician: Mind-Body Healing
Dr. Mauro Zappaterra Harvard-trained physician specializing in physical medicine and rehabilitation, reveals how our understanding of pain needs a revolutionary update.Most doctors treat pain as a purely physical problem, reaching for p...
